Archive of Our Own ^beta

Chapter Text

Living in New York is not how you imagined it would be.

For almost four years, you had fantasised about what your life in a big city would look like. The only thing that kept you motivated (especially when you began to question why you were putting yourself through the misery of a business degree) was thinking about your future in Manhattan. Obviously it was where all the best job opportunities were, but you also wanted the adventure of living in the most cinematic city on earth. You imagined yourself with a big group of friends, a fashionable apartment, and weekends spent sipping lattes while window shopping in SoHo. Every movie and TV show set in New York seemed to promise a romantic lifestyle, and that’s exactly what you wanted for yourself.

So far though, you were coming up short. You had moved into a tiny studio apartment a few days ago, and since then, a vast majority of your time had been spent searching for secondhand furniture to fill up the minuscule amount of space you had. Aside from a neighbour who had given you a dirty look when you accidentally bumped into them in the stairwell, you’d had pretty much zero social contact with any Manhattan locals. So, unable to wait until starting your new job on Monday to meet people, you decide to drag yourself to the dive bar down the street from your building.

It’s Friday night, and the bar is buzzing with patrons. As you shuffle through the crowd, your eyes scan the dingy booths, taking note of the bar’s demographic. Laughing loudly in the corner over pints of beer is a group of frat boys, their phones out on the table as they research which nightclub promises to have the hottest girls. In the booth next to them is a more mellow gathering, a trio of young people with an abundance of tattoos and piercings, all leaning toward the centre of the table as they discuss something in depth. Sitting alone in the booth next to them is a man who looks to be in his late 30s or early 40s. He’s dressed in business attire, but unlike a rowdy group of finance bros seated a few tables away, he doesn’t seem to be letting loose or having any fun. A glass full of some clear alcohol sits untouched on the table in front of him.

“How diverse,” you think to yourself, hoping that out of all the many different types of patrons, there is at least one person in here that you can connect with.

You order a drink from the bar and then grab the last empty table at the very back of the space. The booth is pretty dark and hidden from view, but that doesn’t matter; you just need a spot where you can give yourself an internal pep talk and gain some liquid courage before you force yourself to approach someone, literally anyone, here.

It seems that someone else had a similar idea though. You’ve just taken the first sip of your drink when a large stranger slides into the booth across from you. He’s blonde and broad shouldered with a wide grin on his face, and he quickly eyes you up and down.

“This spot taken?” he slurs, and you don’t respond. If his sloppy speech wasn’t a dead giveaway, the cloud of alcohol fumes surrounding him sure is - the guy is hammered.

Your eyes begin to frantically search the room, wondering how you’re going to get out of this social interaction.

“No need to look around baby,” he grins menacingly. “Everything you need is sittin’ right here.”

You feel your heart begin to race with anxiety. “No thanks, I have a boyfriend,” you say, but you hear a stutter in your voice and you know that your lie is not convincing.

“I don’t see him anywhere,” the man laughs, and suddenly he’s rising from his seat. For a split second, you wonder if he’s going to leave to get another drink or go to the bathroom, giving you a chance to make an escape.

Your heart sinks into your stomach when he takes a few uncoordinated steps over to your side of the booth and slides in beside you.

“Must be my lucky day,” he continues. “It’s not often that you see a woman as sexy as yourself out all alone.”

His last word hits you like a slap in the face. “Alone.” It was never a scary word to you before this moment - you enjoy your own company and aren’t afraid to do things independently - but you’re suddenly very aware that you really are alone with this creep. You might be surrounded by people, but none of them seem to notice the way that this total stranger is beginning to rub his hand up your thigh and lean into you.

————————————

Kendall stares at the glass of vodka in front of him. He’s over 2 months sober but he isn’t sure he’ll be able to make it through tonight without breaking that streak.

Since the… “incident” at his sister’s wedding a few months ago, his life has been in complete shambles. With his father holding that horrific secret over his head, Kendall has been forced to follow Logan’s strict instructions on everything he does and says. He’s nothing more than a puppet. A powerless, pathetic little puppet who will forever live in the shadow of his dictatorial father. Nothing brings him joy, nothing gives him any hope for the future, and nothing makes him feel like he has any control in his own life. The only thing that might make him forget all that for awhile is this glass of top shelf vodka sitting on the table in front of him.

Kendall wraps his hand around the thick tumbler and breathes in the alcoholic fumes. “Fuck it,” he thinks to himself.

He’s about to lift the drink to his lips when something catches his eye. A large man sitting opposite a cute 20-something girl at a table in the corner has just risen from his seat and is walking over to her side of the booth. He stumbles over his feet as he slides into the spot next to her. Kendall catches a glimpse of the girl’s expression before the wide shoulders of the man block her from view, and she looks terrified.

Kendall slowly sets his glass down and continues to watch the scene. He can barely see the girl behind the man’s hulking shape, but he can see the man’s hands reach toward her as he leans in closely, much closer than he would need to if the girl wasn’t leaning away from him.

Without thinking, Kendall abandons his plans to break sobriety and quickly rises from his table. He strides across the room to the booth and, when he reaches the pair, says the first thing that comes to mind.

————————————

“You ready to go sweetheart?”

A deep voice cuts through the loud buzz of the bar, causing the hands of your harasser to fly off you as he turns to see where the sound came from. You look up as well, and your eyes meet deep brown ones. The solo business man you noticed upon your arrival is standing at the edge of your booth, his face showing obvious concern for your well-being. He’s offering you an escape.

“Yes,” you breathe, relief flooding through you as you give him a smile of gratitude.

The drunk creep next to you awkwardly shuffles out of the booth, mumbling a half-hearted “sorry man” as he stumbles away, but your saviour doesn’t acknowledge him. His eyes are locked on you as he reaches out a hand to help you up, holding it gently before he guides you through the crowd, to the bar’s exit, and out onto the street.

Cool autumn air hits your face when you’re outside, and you feel like you can finally take a deep breath. The kind stranger turns to make sure that you weren’t followed out by your harasser before he drops your hand, and you immediately throw your arms around his neck.

“Oh my god, thank you so much,” you exclaim as you hug him. He seems taken aback by the gesture at first before he gives you a gentle squeeze in return.

“Seriously, you have no idea how much I appreciate you stepping in,” you say, pulling away. You look up into your saviour’s face and are met by that deep brown gaze again. He has somewhat dark circles under his eyes, a clear indicator that he works in the Manhattan corporate world, but you also notice the way his eyes crinkle at the sides as he smiles at you. Despite your guess that he’s at least 10 years your senior, this little detail is so endearing. It gives him a youthful, charming look, and you find yourself genuinely smiling back before you extend your hand to him and introduce yourself.

“Kendall,” he responds as he takes your hand, his eyes still crinkled from his smile. “So, uh, tell me,” he asks in his baritone voice, “which fuckin’ TikTok influencer told you it was a good idea to go to the sketchiest bar in Manhattan by yourself?” He gives you a good natured grin as you laugh.

“Hmm, yeah, unfortunately that genius idea was all my own,” you admit. “I just moved to town, I thought it might be a good place to make some friends but I don’t seem to have attracted the right kind of people.” You suddenly realise what you’ve said and scramble to correct yourself. “Not including you of course! You seem like a great guy.”

Kendall smirks in response, clearly entertained by your fear that you’ve offended him. “Really? ‘Cause uh, I’m actually a huge asshole,” he jokes.

You laugh again and feel the tension and anxiety from earlier completely leave your body. Standing out here on the sidewalk with Kendall is the most at ease you’ve been since moving to the city.
“Well you had me fooled,” you smile.

Kendall smiles back and holds your gaze for a moment before he raises his arm from his side to quickly check his watch. It snaps you back to reality and you realise that while you may not have anywhere else to be, that might not be the same for Kendall.

“Oh sorry, I should let you get on with your night. But really, thank you so much for your help Kendall. I seriously owe you one.”

————————————

Kendall’s heart sinks slightly when you say this. His subtle attempt to impress you with his extraordinary wealth did not go as planned. Instead of noticing the absurdly expensive Rolex watch on his wrist, you incorrectly took it as a sign that he was done with you. No, he’s not even close to being done with you. He only has two options on how he will spend tonight - either he distracts himself from his miserable life by getting to know the pretty girl standing in front of him, or he walks back into that bar and finishes the first of what will become many glasses of straight vodka, likely followed by a mass amount of cocaine. Without question, he knows which option he should pursue.

“Well at least let me get a cab to take you home. Or, uh, if you want, we could get a drink at a much better spot down the street...” He eyes you intently, trying not to pressure you into joining him, but desperately hoping that you want to continue the night.

To Kendall’s relief, you smile and don’t hesitate in answering “Yeah, okay. Let’s go.” He gives you another genuine smile that reaches his eyes and leads the way.

“So, uh, where’d you move from?” he asks as you walk side by side. You give him a quick summary of your hometown and where you got your degree, and he watches you as you answer, noticing the way that you keep your eyes forward but take quick glances up at him through your eyelashes. He smiles a little bit every time your gentle gaze meets his.

“What about you?” you ask in return. “How’d you make your way here?”

Your second question, as simple and sincere as it is, sends Kendall’s mind into high gear because it confirms something for him - that you have no idea who he actually is. Whether you know anything about Waystar or the Roy family, he isn’t sure, but you clearly aren’t aware that you’re walking beside one of the most influential men in New York City. Kendall’s heart beats a little faster as he realises that he doesn’t need to play the role of Logan Roy’s puppet tonight, and that, for the first time maybe ever, he can get to know a woman without wondering whether she’s only interested in his money or status. Tonight, he’s not a Roy.

“Actually New York born and raised,” he responds, and does his best not to react when he sees your head turn toward him in surprise. “So a business degree huh?” he quickly asks before you get the opportunity to probe into his immensely privileged upbringing. “Coming to join the rat race?”

“Unfortunately,” you sigh. “I start my first big girl job in the corporate world on Monday,” you say before turning to him with a somewhat cheeky smile. “Which I’m assuming is also your stomping ground?”

“Uh yeah, pretty much,” he says, giving you a half-hearted smile. “Although I wouldn’t necessarily describe it as a stomping ground, more like a uh… fuckin’ battlefield.” He laughs lightly before suddenly eyeing you up, his smile growing a little wider. “You, uh, you definitely don’t strike me as the corporate type though.”

The two of you reach the bar and Kendall holds the door open for you, allowing you to step inside first. You raise an eyebrow slightly as you pass by him and enter a much quieter and much swankier bar than the one the two of you just left. He leads you to a table in the corner and a server promptly comes over to take your drink orders. After you order your regular, Kendall orders a bitters and soda and desperately hopes that you don’t question his choice to not order an alcoholic drink. To his relief, you don’t. You have a different question in mind.

“Sorry, I wanna get back to what you said before” you say, leaning forward on the table. “About me not being the corporate type. You don’t think I’m capable of being a ruthless shark?” You prop your elbows up on the wooden surface and rest your chin in your hands, narrowing your eyes in challenge as you await his answer.

Kendall smiles again, happy with the new direction his night has taken. The glass of vodka he left sitting on the table at the last bar is the furthest thing from his mind right now.

“I mean, you tell me,” he challenges in return. “You just don’t seem like the cutthroat type. But uh, who knows,” he says as he leans slightly forward. “Maybe you’ve got some cruelty under your, uh, sweet exterior.”

Kendall gives you an expectant look and is pleased to see you avert your eyes from his gaze for a moment and smile sheepishly. You’re clearly trying to hold your own against him but just can’t stop your shy side from coming through. The fact that he can so easily break down the cheeky-front you’re trying to put up makes him feel in control of something for the first time in awhile.

“I mean, are you the competitive type?” he presses. “Or do you tend to play nice with others?”

You look down and your timid smile grows, confirming his theory. “Yeah you got me,” you laugh lightly. “I’m definitely a play-nice, let’s-all-get-along, rainbows and butterflies kind of girl.” You laugh again, slightly embarrassed. “I don’t know, maybe you’ll have to take me under your wing and give me some lessons in being an asshole.”

Kendall chuckles, trying to remain casual, but your phrasing has his mind immediately wandering to thoughts of you under him. It’s been so long since he’s felt this excited about flirting with a woman. When he’s ‘Kendall: son of Logan Roy,' there’s no chase. 99% of the time, his money and name will get him any girl he wants. But as ‘Kendall: the random stranger from the bar,’ there’s a chance he might actually strike out and go home alone tonight. The anticipation of whether or not that happens is exciting as hell.

Your server drops off your drinks just as Kendall feels his face warming.

“I don’t know, I think my asshole ways are probably a bit too extreme for you,” he says coolly as he wraps his hand around the thick glass.

“Oh c’mon, I can be a bitch!” you exclaim, but you say it in such a peppy way that Kendall can’t help from breaking into a huge smile.

“Oh yeah, you’re very convincing,” he grins as he takes a sip of his drink.

You grin back. “Seriously though, you seem to be able to balance your nice and asshole sides pretty well. I don’t want to be destroyed on Monday, how’d you learn to hold your own?”

Kendall swirls his glass in his hand. “Well I, uh, I was raised by a father who rules with an iron fist, so it’s kind of ingrained in me to be ruthless...”

He regrets his words the minute they’ve left his mouth. This is supposed to be a fun night with a cute girl, it’s supposed to be a moment of freedom from his father, but here he is, immediately bringing him up when given the chance.

You raise an eyebrow slightly. “No offence, but I really doubt it’s from your daddy issues Kendall. If it was, I’m pretty sure a majority of the population would be ruthless.”

Kendall gives a low chuckle and instantly feels the tension that had begun to build in his shoulders dissipate. He’s grateful (but also impressed) that you so easily sidestepped his impulsive answer.

“Ok, well, where do you think my cutthroat tendencies come from?” he challenges.

You cock your head to the side and squint your eyes, inspecting him before you nod to yourself. “I have a theory,” you say, but you don’t give up your answer immediately. You take a sip from your glass, and Kendall watches, amused, as you try to build tension before you reveal your thoughts.

“Alter-ego,” you finally say. “Like Sasha Fierce. An asshole that comes to life when you walk into the office. But I feel like your alter-ego is named Emperor K or Big Ken Doll or something.”

Kendall smirks at your theory, knowing it’s wrong and that ruthlessness is a core part of who he is, but he’s entertained nonetheless. “Oh yeah? And where’d you get those names from?”

You take another sip of your drink. “You strike me as someone who’d be into cheesy 90’s hip-hop and would pick that kind of name for yourself.”

Kendall laughs this time. “Damn, you’re uh, you’re not far off. Are you telling me you don’t like 90’s hip-hop?”

“God no,” you scoff. “I came of age when trap was the big thing. I can’t take that cringey 90s stuff seriously, I’m far too gangster for that.” You flash a cheeky smile at him.

Thus begins the next few hours of your night. You and Kendall begin discussing music, which evolves into films, then books, and then a myriad of other topics. The conversation flows naturally, and Kendall finds himself feeling what he thinks must be happiness for the first time in ages. He can’t be sure, it’s been so long since he’s felt anything close to that word, but talking to you feels easy and right. The only stress he’s currently feeling is from his fear that he’ll slip up and reveal to you that he’s a Roy. While he does openly share his thoughts and experiences, he has to keep his stories vague enough to ensure that he doesn’t out himself as the heir to a media empire.

Eventually you move onto the topic of university and are telling him about the time you slept through one of your final exams but somehow convinced the professor to still let you take it. Kendall laughs as you end your story by saying that you failed the exam anyway.

“Still impressive. If you can talk your way out of that shit, you’ll be fine on Monday. Corporate speak is mostly just being persuasive as fuck.”

You lean back in your chair and give him a defeated look. “Yeah I can be persuasive when I really want something, but not when the other person wants something else more. I back down so fast when someone else makes it’s clear that they’re not gonna budge.”

Kendall frowns slightly and shakes his head. “I uh, I won’t lie to you… you’re gonna have a shitty time if you can’t stand your ground. Anyone who senses any weakness in you will fuck you over in a heartbeat.”

“Yeah I know, and it terrifies me.” You look away from the table and sigh, crossing your arms. “I wanna do well but I’m just not good at playing mind games. And I’m such a people pleaser that I’m willing to make myself miserable to make life easier for someone else.”

Your eyes are still staring off to your left, but Kendall’s are on you. He notices the little crease that’s developed between your eyebrows as you likely think about what Monday holds for you. At Waystar, he feels no pity for those who can’t keep up with the requirements of the job. But in this moment, with you… he sees a girl who really wants to succeed in her chosen field, but has too good of a heart to act viciously when necessary.

“Who knows… maybe you’ll surprise yourself. I don’t know, you could, uh, be capable of more than you think,” Kendall offers, not exactly sure if he’s being comforting but wanting to try. He pauses for a second, debating if he should add the next part. “It’s, uh… refreshing, to meet someone as real as you. Someone who isn’t afraid to say exactly how they feel.”

————————————

You turn to face forward, your eyes meeting Kendall’s again. He seems unsure of what he just said, his face watching yours for your reaction. You smile softly.

“You must not meet a lot of very real people if me saying I’m a people pleaser is refreshing.”

Kendall gives a small chuckle as he looks down at his drink, swirling it in his hand. “Uh yeah, I don’t. Doubt there are very many real people in the crowds I run with.”

“Or maybe you’re too intimidating and people don’t feel comfortable opening up to you,” you say as you lift your glass to your lips. You know it’s a ballsy comment to make, but you’re about 3 drinks deep at this point and your politeness filter is beginning to fade.

Kendall looks at you, eyebrows slightly raised and the hint of a smile creeping onto his face. “…Are you intimidated by me?”

“… Yes.”

The smile on Kendall’s face grows a little bigger. “Hmm, okay. Tell me why.” He takes a drink from his glass but keeps his gaze on locked on you. You see something flash behind his eyes - Interest? Power? Attraction? You’re not sure, but it’s clear that you have his undivided attention.

You look at Kendall and think, trying to verbalise what it is about him that’s so intimidating to you. “I think it’s a mix of things… I mean, hearing how aggressive you’re willing to be in your career kind of solidified you as someone I should maybe be a little scared of, but it’s also the way you carry yourself. It feels like you belong in any room you walk into. And how deep your voice is.” You can feel your face flush slightly as you say this last part and hope it’s not noticeable.

If it is, Kendall doesn’t say anything. He waits for you to continue. “I think it’s something about your eyes too… they’re intense… and wise,” you say thoughtfully, slightly cocking your head to the side as you let yourself get dragged into the gravity of his deep brown gaze. You suddenly realise how intently you’ve been staring at him and quickly look away. “And I swear that’s not me calling you old,” you joke, breaking the tension of the moment.

Kendall gives a light laugh and leans back in his chair. “So uh, basically what you’re saying is I’m a hot older guy with loads of charisma.” He gives you a mischievous grin.

You take a sip of your drink as you smile and roll your eyes. “I mean, I definitely didn’t say that, but I won’t disagree.”

Kendall leans forward again, resting his forearms on the surface of the table. Over the last few hours, his professional attire has slowly become more casual. His blazer hangs over the back of his chair, his tie is slightly loosened, and the sleeves of his dress shirt have been rolled up. You watch as he flexes his hands, protruding veins weaving across the surface of his skin.

“If we’re being honest with each other,” he says, eyes somewhat glazed over and settled on a spot in the middle of the table, “I don’t usually hang out with women like you.” He looks up at you. “But I’m uh, I’m kind of digging it.”

You lift your drink to your lips again and give him a somewhat skeptical look. Pausing before setting your glass down on the table, you lean in as well. “Okay. I’ll bite. What’s so different about me from the girls you usually hang with?”

“Well, you’re not afraid to be yourself or say what you’re thinking. There’s a uh… an innocence and… positivity to you that I don’t come across often.” He pauses for a moment. “I don’t want to be a dick, but most of the women I meet are pretty vain and materialistic. And you can tell that they want you think they’re sophisticated.” He sits a little taller. “I’m not saying that’s bad, just… you’re a breath of fresh air.”

You watch Kendall as he speaks, the smile on your face growing a little wider with every cliché he uses until you can no longer hold it in. The “you’re different” move is typical, but this? You let out a laugh and hide your face in your hands.

“You realise you just called me unsophisticated? To my face?” You laugh again and lean back in your chair. “Damn Kendall, you really know how to flatter a girl.”

Kendall bows his head and lets out a low chuckle. “Uh, yeah, okay, I guess I deserve that… I’m just being fuckin’ honest though, you’re uh, you’re new for me… in a good way.”

You smile and lean forward again. “I’m just fucking with you Kendall, it’s fine.” You make the sudden decision to place your hands on top of his, halting the way he had started to fiddle with them. It’s the first time you’ve touched each other since he pretended to be your boyfriend and led you out of the other bar hours earlier. It feels like a lifetime ago.

Kendall looks from his hands up to you. His expression is impossible to read, but it’s clear a moment later what he might’ve been thinking. He gently removes his right hand from under yours and reaches up to tuck a strand of your hair behind your ear. Your breath catches in your throat as his touch lingers there for a moment, convinced he’s about to kiss you, and utterly disappointed when he pulls away. Your disappointment doesn’t last long though.

“Hey, did you uh, maybe want to find somewhere else to continue our conversation? Looks like they’re closing up here.” Kendall glances around, prompting you to do the same. Somehow you’re only just now noticing that the two of you are the last customers in the bar. The only people left are the bartender and your server, both of whom seem to be distracting themselves with menial tasks and small talk as they wait for you and Kendall to leave.

“Umm…” you pull your phone out of your bag and check the time. 2:48am. Jesus Christ, you had no idea it was that late. You should probably just say goodnight and go home, but you can’t bring yourself to. Not after you look up and lock eyes with Kendall. His face isn’t conveying any strong emotion, but his eyes… maybe you’re imagining it or just seeing what you want to see, but it’s almost like they’re pleading with you, begging you to say yes and stay with him, and fucking hell, you actually want to. After days of being alone in an unfamiliar city, connecting with Kendall tonight has felt so good. You’re not ready to give up that feeling yet, so you make a stupidly impulsive decision that you’re sure you’ll regret in the morning, but feels right in this moment.

“Could you walk me home?” you ask innocently.

Kendall takes a second to absorb what you’ve asked of him before answering “Uh, yeah, of course,” though he seems slightly confused as to what this request actually means.

He stands up and walks over to your side of the table, offering you his hand to help you out of your chair. You smile and accept the gesture, expecting him to drop your hand once you’ve stood up, but he doesn’t. He grasps it firmly and leads you out of the bar, only slowing down for a moment to mumble something to the bartender about charging the bill to his account. The bartender nods in acknowledgment before turning his attention back to the glass he’s polishing.

Kendall drops your hand to hold the door open for you, but quickly reaches for it again once you’re out on the street.

“So where do you live?” he asks lightly as he looks over at you, but he breaks into a smile as your eyes meet. You’re looking up at him and making no attempt to hide the confusion you’re feeling from appearing on your face.

“What?” he asks with a chuckle.

You give a slight shake of your head as you begin to lead him in the direction of your apartment.

“You,” you answer. “I meet you at the shittiest bar in the city, but you have an account with a bar that’s ten times nicer right down the street?” You scoff slightly, keeping your eyes forward but feeling his on you. “You are an enigma Kendall.”

He laughs softly. “I, uh, I promise it’s not that complicated. It’s just good to have a nice place to bring someone you want to impress.” You feel a gentle squeeze of your hand and your stomach fills with butterflies. “But sometimes it’s uh… sometimes I don’t wanna be in that world, you know? It’s nice to disappear into a crowd.”

“I don’t mean to burst your bubble,” you say, glancing over at him, “but you were one of the first people I noticed when I walked in that bar.”

Kendall’s eyes quickly flash in your direction. “Oh really?” You feel his arm tense up beside you. “And uh… what did you notice?”

“I was mostly just wondering what the old guy was doing in there.” You grin over at him and he scoffs, shaking his head with a smile. “No, just kidding. I guess I mostly noticed that you seemed… stressed. I don’t know, that your vibe was just on a different wavelength than everyone else in there.”

Kendall sighs before answering. “Well… yeah, I uh, I wasn’t having the best night earlier.” You see him glance over at you in your peripheral vision. “It’s a little better now though.”

You turn to look at him, mock offence on your face. “Just a little bit?!”

“No, you’re right, much better,” he says, and he flashes you his crinkly eyed smile again.

The walk to your place is short. Kendall points out a bar he and some friends tried their first fake ID’s at when they were in the 9th grade, but seems reluctant to give specific details when you ask more about what it was like growing up in Manhattan. Before you know it, you’ve reached your street and are slowing to a stop in front of your building.

“This is me,” you say as you turn to Kendall.

————————————

Kendall looks at you smiling sweetly up at him, and his heart both swells and sinks at the same time. He’s not ready for tonight to be over. What began as a mere distraction from his shitty life has turned into… something he wasn’t expecting. It’s rare that sober-Kendall socialises without thinking “this would be more fun with coke,” but that thought didn’t occur to him even once tonight.

“I, uh…” He tries to think of something to say, something that might keep him here with you for a few moments longer, but nothing comes to mind. His eyes flicker between yours and he feels his composure slipping. Then, in an instant, he loses himself. Giving in to his impulses for the first time all night, his right hand finds your cheek, his left your waist, and he leans in, gently brushing his lips against yours.

The kiss is over before it’s even begun. Kendall pulls back almost immediately because for a split second, he felt like he had broken sobriety. Letting his urges take control and kissing you felt eerily similar to the feeling he gets when he does a line for the first time after months of being in recovery. Something that feels this good is usually not good for him, and he’s learned to associate that kind of pleasure with guilt.

Kendall looks down at you, his mind spiralling as you stare back at him, your lips slightly parted. For a split second, he wonders if he misread the moment and fucked everything up, but you put those fears to ease when you reach up to wrap your arms around his neck and pull him back in.

Your kiss is not hesitant or soft like Kendall’s was. Your lips move purposefully against his, almost urgently, and he feels your arms tighten slightly around his neck as he reciprocates your enthusiasm. Almost immediately, he loses himself in the moment. He lets his hunger for you take over and begins to feel his hands move of their own volition. His right hand, which had been placed gently on the side of your face, migrates to the nape of your neck where it begins to tangle itself in your hair, and he can’t stop his left hand from exploring the rest of you. It had previously been resting lightly on your waist, but he feels it begin to run up and down your back, desperate to feel the skin beneath your light jacket. This isn’t good enough, there’s still too much space between the two of you, but he’ll take whatever he can get in this moment. His grip on your neck tightens slightly, and his palm presses firmly against you to push you further into his body.

You react exactly how Kendall hoped you would. He feels you lean into him, and your arms loosen around his neck so that your hands can run through the short hair at the back of his head. Excitement begins to stir deep in his stomach, and he’s suddenly very aware that the two of you are standing out on the street, unable to get any closer. It’s probably a good thing that a moment later, you begin to gently pull away.

Both of you are breathless as you break apart, neither of you removing your hands from the other. You drop your head sheepishly and Kendall looks down at you, waiting for your eyes to meet his. His heart races in anticipation as he awaits your reaction to what just happened. Fuck, he really wants to keep kissing you.

Finally, you look up at him again and he holds his breath, waiting for you to say something. The next thing he knows, he’s watching the most beautiful smile spread across your your face as you roll your eyes. He feels your arms retreat from around his neck, and your hand entwines itself with his. You utter a soft “c’mon” as you lead him into your building.

Kendall feels a jolt of electricity run through his body. Jesus fucking Christ, it’s happening. There was no need for name dropping, wining-and-dining, or surface level small talk. No sleazy clubs or hardcore drugs or excessive amounts of alcohol. He likes you, you like him, the end.

He’s vaguely aware that you’re leading him up your building’s stairwell, down a tired looking hallway, and to a white door adorned with the number 201, but he’s mostly focused on the buzzing anticipation building in his chest. You drop his hand to pull your keys out of your bag and unlock the door, pushing it open and dragging him inside with you.

Your urgency to get him inside tells him that he doesn’t need to waste time with awkward pleasantries or forced compliments about your apartment. You quickly shut the door behind him and not a moment later, he’s got your back pressed up against it. The two of you pick up exactly where you left off on the street.

————————————

Your hands find their way to the back of Kendall’s head again, fingers running through his short hair as he rushes to press his mouth to yours. The Kendall who initiated the soft brushing of lips outside is long gone and has been replaced by a starved man who can only be satiated by you.

You feel the solid wall of your apartment door press into your back as Kendall leans further into you, mouth practically devouring yours as his hands grip your waist, your hips, your ass. One of his hands travels further down the back of your thigh so that he can hike it up and place it around his hip. You gasp at the new position, feeling the hardness of Kendall’s groin push into your core.

Kendall groans into your open mouth as he begins to rut his hips against you. The bulge protruding from his pants hits the sweet spot between your legs and the excitement that’s been building deep in your stomach multiplies. You hear a moan escape from your lips, and it sends Kendall into a frenzy.

“Fuckkk,” he growls, his voice somehow sounding even deeper than before. His hands travel up to your face and he kisses you harder. Anywhere his body can be pressed into you, it is. His enthusiasm is intoxicating, but he seems intent on taking his time with you here at second base. He’s made no attempt to take anything further, not even a hand sneaking up under your shirt.

You, on the other hand, are impatient for more. Your inner thighs are growing increasingly wet and you’re growing increasingly frustrated. Why the fuck do you both still have clothes on? You usually like to take your time with foreplay, but the urge you have for Kendall right now is building too quickly and you want nothing more than to feel his hands on your bare skin.

You remove your hands from Kendall’s hair and lower them to his waistband where you begin to pull up the dress shirt tucked into his pants. Grazing over the rock hard erection pushing against the cloth of his trousers, you feel his length twitch against your fumbling hands. His breath hitches in his throat, only for a moment, before his lips are suddenly on your neck, leaving kisses and licks and bites up and down the side.

“God you’re so fucking hot,” he breathes against your skin as you frantically work to undo the small buttons until his shirt falls open. Your hands rush to push the fabric off his shoulders and finally feel his warm skin on yours, exploring the toned muscles of his upper arms and back as you do. His mouth latches onto yours while he pulls his arms out of the sleeves and throws the shirt behind him, hands quickly racing to the bottom hem of your own top as soon as they’re free. He helps you pull it over your head until it drops to the floor beside you, and you feel his hands run up and down your back, his touch exploring every inch of your skin that he can access.

The ache building between your thighs is becoming unbearable at this point. The inside of your underwear is a mess of slick, and Kendall’s hardened groin pressed against you isn’t enough anymore. Your hands retreat from his back and fall to your own waist, where you hook your fingers into your waistband and pull your pants off your hips, stepping out of them quickly. Kendall has no time to react before you grab one of his hands and guide it to your core, placing it outside your underwear where he can feel how wet you are.

A deep groan sounds through your apartment the moment Kendall feels the damp fabric clinging to your centre. “Fucking hell,” he husks as he begins to rub, and you echo him with a moan. Relief rushes through your body as two of his finger circle your clit, but now you’re feeling your entrance begin to clench around nothing and you ache for Kendall to satisfy that need too. Your hands fly to to his belt buckle.

“I want you so fucking bad,” you breathe as you attempt to unbuckle it, but your hands are shaky from anticipation and you can’t get it undone quickly enough. Kendall suddenly grabs your wrist, halting your fumbling fingers. “Bed,” is all he says before he’s kissing you again, leading you backwards toward your mess of blankets and pillows in the corner while he expertly undoes his belt with one hand, the other hand tangling itself in the hair at the back of your head.

His belt is undone by the time you reach the bed, as well as his pant’s button and zipper, and soon he’s pushing his trousers down his hips and kicking them off. Seeing Kendall like this, his erection fighting against the thin cotton of his boxers to spring free, increases your sense of urgency. You’re done with foreplay; you’re not even fully naked yet, but you have the hazy vision and tight knot in your lower stomach that always precedes your climaxes. You need him - now.

You remove your bra and underwear in a frenzy and pull Kendall onto the bed with you, plush duvet and collection of pillows cradling your naked body as he rests his weight on top of you.

“You’re so gorgeous,” he groans into your neck, his hands running over your breasts, waist, hips, and down to your core. He slides one finger between your folds and feels the pool of arousal that’s developed there. “Holy fuck,” he moans deeply, his hand rushing to palm his groin over his underwear while the other continues to spread your slick around your crease. “Fucking please let me feel you,” he husks, inserting one finger into your slit and eliciting a loud moan from you.

“Oh my god, yes,” you breathe as he continues to pump his finger in and out. It feels incredible to finally have something for your inner walls to clench around, but you’re ready for the main event. You reach down and grab his wrist, feeling his finger slip out of you as you bring it up to your lips and place it on your tongue before closing your mouth and sucking your arousal off him. Kendall emits a primitive sound, something between a moan and growl, as he feels your tongue swirl around his finger, his eyes fixated on your mouth.

“God I have to fuck you right fucking now,” he groans, pulling his finger from between your lips and racing to place his mouth on your neck. His hand falls back to your core and he rubs your clit, causing you to whimper as you reach over to your bedside table and pull a condom out of the drawer. Kendall takes it from you, rips the wrapper open with his teeth, and rushes to roll it onto himself. He’s frantic to line himself up at your entrance, but takes his time as he pushes in. You moan in unison as he buries himself fully inside you, the feeling of you stretched around him bringing the sweetest relief to the aching arousal you were experiencing before. He pulls out halfway and then fills you again, slowly building up a rhythm until he’s furiously thrusting into you.

“Fuck you feel incredible,” he says, his breathing becoming more ragged and heavy. His gaze is locked on where he’s entering you, watching his cock disappear into your hole and then feeling your inner walls squeezing him tightly. “I don’t know how long I can last.” He looks into your eyes, his pupils blown out with lust and you’re sure that he’s seeing the same thing in yours.

You moan again at his words, eyebrows creased and lips parted, and you feel the elastic in your core begin to tighten with his steady rhythm. This has never happened so quickly before. You’ve never approached a climax with any previous partner this fast, but you’re already so close to your release that it feels like he’s been edging you since your kiss on the street. “Please keep going,” you plead. “Please, I’m gonna cum.”

You can feel yourself getting tighter around him, and you know Kendall can feel it too because he emits a husky groan as you begin to approach your peak. His rhythm is becoming more erratic as he gets close to his own climax, his hips thrusting at an uneven pace and heavy breathing interrupted by deep groans. His hand reaches down to your clit, where he begins to rub quick circles. The elastic snaps immediately.

Heat rushes through your body as you moan out an “oh my god” and grip Kendall’s toned back, holding yourself close to him. You feel an internal pulsating and rush of wet in your core, your mind spinning as Kendall continues to fuck you through your orgasm. This doesn’t last long though, as the sensation of your climax around him sends him over the edge too.

He pushes himself deep inside you and his entire body tenses up as he lets out a long, drawn out moan, holding you tightly against him. The pleasure of your own orgasm washes over you as you feel his heart beating frantically in his chest and his erection twitching against your inner walls. The only sound in the room is both of you breathing heavily. Soon though, he’s relaxing his bodyweight on top of you, and you’re wrapping your arms around him as he catches his breath.

One of your hands reaches up to run your fingers through his hair and he sighs contentedly, his head dropping beside yours and resting on your shoulder. “Fuck,” he mumbles into your skin. “That was… fuck,” is all he can manage to say, and you aren’t capable of too many words either. The most you can think to add is a light laugh and a “yeah… fuck,” as your fingers continue to run through his short hair. He sighs again, his breathing beginning to slow and his erection beginning to soften, and you enjoy what you assume will be the last bit of physical touch you’ll experience tonight. No one ever sleeps over after the first hook-up.

Eventually he turns his head to kiss your cheek and then lifts himself off your body. Groaning, he slides out from inside you and you feel the remnants of your arousal seep out as well. Kendall pulls the condom off and throws it into the garbage bin near the foot of your bed before collapsing next to you. You’re surprised when he immediately pulls you into his arms, but you settle in right away, overjoyed that he's keen to cuddle too.

“God you’re incredible,” he breathes as he buries his face into your neck, leaving a soft kiss where your jawline begins.

“Right back atcha,” you murmur, nuzzling into his chest, and you feel his arms wrap around you a little tighter. It surprises you how comfortable you already feel with him.

The night has caught up with you though and you suddenly feel how exhausted you are. It’s almost 4am at this point, and the combination of being post-orgasm, nestled in your cozy bed, and wrapped up in Kendall’s arms has you feeling extremely relaxed. You can’t help but let a little yawn escape.

“Is it time for me to go?” Kendall asks softly. Despite his low volume, you can feel his deep voice rumbling in his chest.

“You don’t have to go,” you mumble sleepily. “It’s so late, you should stay.”

The offer slips out of your mouth without any forethought, but you don’t regret it. Somewhere in the back of your mind you can feel that what you’ve done tonight with someone you met only hours ago is probably too-much-too-soon, but you can’t bring yourself to care just yet. You’ll deal with the consequences tomorrow, but you’re happy to give yourself what feels good right now, and Kendall feels good.

Kendall leans his head down to leave a soft kiss at the top of your head. “Okay,” he responds, “I’ll stay.” You nuzzle into his chest again, taking a deep breath and relaxing fully. You fall asleep to the feeling of his arms around you and the soft rhythm of him stroking your hair.

***

You’re awoken by the sound of a phone ringing. Somehow, in your half-asleep daze, you’re able to recognise that this is not your own ringtone sounding off. You’re momentarily confused until you feel the warm body pressed against your back gently pull away, and last night’s memories come flooding back to you. Smiling to yourself, you roll over just in time to watch Kendall sleepily walk over to the other side of the room where his pants lay crumpled on the floor. He pulls a cellphone out of the side pocket and you notice that his shoulders immediately tense up as he reads the name on the screen.

“Dad?” he says in a low voice as he picks up the phone, and you slowly sit up in bed behind him. Kendall spins around to the sound of your movement and you’re surprised to see he looks slightly embarrassed. He clears his throat before pointing to the bathroom to ask if he can take his call in there while he says “Uh yeah, just a second,” into the phone. You nod an ‘of course’ and he strides over to it, quickly closing the door behind him.

You grab your phone from the nightstand and attempt to not eavesdrop, but it’s difficult. Kendall sounds nothing like he did last night and it’s throwing you off. He’s still speaking in the same deep tone, but the confidence and banter is gone. The voice on the other side of the bathroom door sounds serious and slightly anxious, like Kendall isn’t fully sure of himself or anything he’s saying. You think you hear him say the word “cruises,” but you aren’t sure. You can’t imagine that planning a family vacation would make him sound this stressed out, but he did mention a ruthless father…

You attempt to turn your attention back to your own phone. Kendall obviously wanted to hide this call from you for a reason, and you barely know each other; you have no right to be theorising about his family life or listening in on his personal conversations. You open the message app on your phone and see a few texts that your best friend from back home sent you last night. You respond to her messages before adding a “btw… I met someone last night” text. You have a scheduled phone call with her later today, but you’re too excited about meeting Kendall to wait until 3pm to tell her. Wondering how long you have until your call with her, you check the time and see that it’s only 7:57am. Why the hell is Kendall’s dad calling him this early on a Saturday morning?

The bathroom door opens a moment later and Kendall steps out, looking even more exhausted than he did when he had just woken up. You lock your phone and set it down beside you on the bed.

“Everything okay?” you ask, pulling your knees up and hugging them to your chest. Despite being in your own apartment, hearing the tone of his call has you feeling a bit like you’re intruding in his space rather than the other way around.

Kendall scoffs lightly and walks over to the bed, sitting on the edge of it. “Uh, great, can’t you tell?” He looks over at you with a playful smile but you can tell that his heart’s not in it.

“I’m sorry,” you say sympathetically. “That’s not a fun way to start your day.” You’re tempted to reach out for him and hold his hand or pull him back into bed with you, but Kendall doesn’t seem to be in an affectionate mood. His body is tense and he’s seated as if he’s preparing to stand up at any moment. “Do… do you need to leave?”

You know the answer before the question has even left your mouth, but Kendall confirms your suspicions when he sighs and looks down.

“Uh, yeah. I have some uh, some stuff I need to take care of.” He hesitates for a moment before standing up and quickly grabbing his clothes from their various spots around the room. You watch him get dressed, your knees still hugged to your chest. “I’m really sorry I have to rush out so soon,” he says as he buttons up the front of his shirt.

You smile at him gently. You don’t doubt that he actually does have stuff to take care of, but the way this is ending feels more like a one-night-stand than you’d like it to. You do your best to hide your disappointment. “It’s okay Kendall, I understand. Go take care of business.”

He gives you a small but grateful smile as he quickly pulls on his shoes, and then walks over to the bed. “I had a lot of fun last night,” he says as he places his hand under your chin to tilt your head back. He leans in slowly and brushes his lips softly against yours, causing the little group of butterflies in your stomach to stir. The gesture is surprisingly sweet, and your fear that this was turning into a one time thing is momentarily put to rest. He pulls away, brown eyes locked on you as he reluctantly drops his hand from your face. “I’ll see you soon,” he adds, and then he’s gone.

You stare at the closed door for a few seconds before flopping backward on your bed. Your eyes fixate on your ceiling and gradually glaze over as you try to commit his face to memory. You run over every detail you can remember from last night, looking for signs that he only wants something casual, or worse, is going to disappear now that he’s gotten what he wanted from you. He did say he’ll see you soon… you wonder if he’ll reach out later today once he’s handled his personal business.

It’s when this thought appears in your mind that you come to the awful realisation that you and Kendall never exchanged numbers.

————————————

Kendall shuts your front door behind him and pulls out his phone as he strides down the hallway toward the stairwell. He quickly orders an Uber to pick him up outside your building (he prefers to use his personal driver for transportation, but Uber Black does the trick when he needs a last minute ride) and sees that the driving time to get to his Dad’s place from yours is over 20 minutes. Fuck. He can already hear the condescending comments that Logan will undoubtedly make about him taking so long to arrive. The news he received on the phone this morning, that New York Magazine is preparing to publish an article about the Waystar cruise line misdeeds, has put his father in the worst mood imaginable. When the company could be under investigation and the stock could plummet in a matter of hours, 20 minutes will not go unnoticed.

Kendall exits the stairwell and steps out onto the street, immediately lighting a cigarette; it’s the only vice he has to keep him sane these days. Last night was the perfect escape from the depressing reality of his life, but this morning has been the most aggressive push back into it. What he wouldn’t give to have been able to spend a few more hours with you.

He takes a puff of his cigarette and stares up at your building, wondering which window belongs to you. Maybe, if he’s able to bury the article about cruises, he’ll be able to see you again soon. He should probably text you though to let you know that he’s going to be busy for awhile.

His heart sinks into his stomach. He can’t text you because he doesn’t have your number. He never asked for it.

He looks down at his phone screen, sees that his Uber is 2 minutes away, and then up to your building. 2 minutes is definitely enough time to run back upstairs and ask you for your number, and he’s sure you’ll want him to have it.

He takes a step toward the front door, but stops himself suddenly. His mind is already in critical thinking mode as he prepares to find a solution to the cruises scandal, but now it’s beginning to consider what the outcome of him going back upstairs will be. If he gets your number… what’s next? A normal relationship with you isn’t possible. You’ll eventually learn who he really is, and he doesn’t see any way that ever ends well.

By your own admission, you’re already intimidated by him. Learning that he’s a billionaire with more power than 99.99% of the world population won’t make you feel any more comfortable around him. And what about the people in his life? How could you, being as authentic and sweet as you are, ever hold your own around his family? If you stuck around with him long enough, would his money corrupt you the same way it corrupts everyone else in his world? Would everything start to feel as meaningless for you as it does for him?

He can’t do that to you. He won’t. You’re still young and impressionable, and he would never forgive himself if he pulled you into hell with him when you still had your entire life ahead of you. It’s best that he leaves last night as a memory. A really fucking good memory.

Kendall glances at his phone and sees that his Uber is right down the street, only a minute away. He look up at your building once more before taking another puff of his cigarette and then stomping it into the ground just as his car rolls up. He gets in silently and begins to prepare himself for a full day of Waystar chaos. What a fucking start to the weekend.

Chapter Text

Your Saturday morning crawls by.

You do any and everything to distract yourself; you clean your apartment, you run out for a latté and pastry, you reread your favourite book, but nothing can stop the aching disappointment you feel in your chest. The realisation that Kendall doesn’t have your number, and you don’t have his, is beyond upsetting for you. Yes he’s the only person you’ve connected with in the city, but you also really (really) like him, and now you aren’t sure if you’ll ever see him again. You don’t know his last name, what he does, where he works… there’s nothing for you to go off of. Finding one specific man in a city of millions when the only piece of information you have is his (very common) first name is more or less an impossible task.

The only hope you have that you’ll see Kendall again is if he goes out of his way to get in contact with you. He knows where you live, so it’s entirely on him to make the next move. He could leave a post-it note downstairs, send a letter, hell, he could even show up at your front door. You really don’t care how he reaches out, you just hope he does. You’re not optimistic though - your dating history has left you with very little faith in men, and the possibility of him disappearing completely seems to be the most likely outcome. You sit in your anxiety all day until it’s time for your phone call with your best friend from back home. She does her best to alleviate your worries.

“Okay, so there’s nothing you can do,” she offers. You’ve recounted your entire night with Kendall to her, and after a lot of laughter over the gritty details, she’s gone into reassurance mode. “It’s out of your hands so just let whatever happens, happen. If he really likes you, he’ll make the effort to see you again. And if he doesn’t, then that’s not someone you want to waste your time with.” You sigh. Of course she’s right, but it doesn’t stop you from still wanting Kendall to want you too.

She hears your sigh and changes her approach. “You’re in New York dude! The dating possibilities are endless. I can guarantee there’s a thousand other finance bros out there who would jump at the opportunity to get in your pants.”

You laugh before putting on your brattiest voice. “But I wanted this finance bro,” you whine, and the two of you giggle together.

“Whatever,” she chuckles. “I just don’t think you should set your sights on the first guy you meet anyway. Explore your options. And didn’t you say he was in his 40s or something?”

You roll your eyes. “I don’t know exactly how old he is but yeah, somewhere around that probably.”

“Okay, so like… what if he’s secretly married or something? What if he’s been divorced like 10 times and has dozens of children with multiple women? A crush is just a lack of information, don’t build him up in your head.”

You have to admit that she has a point there. You don’t really know anything about Kendall when it comes to his personal life. He could be a sexist, racist, homophobic douchebag for all you know, and the idea of him saving you from having to learn that yourself is actually somewhat comforting.

“Yeah, okay, fine,” you concur. “I won’t get my hopes up.”

“Good,” she responds. “Just have a relaxing weekend before you start work. I have a feeling you’re about to be so busy that you won’t even have time to think about him anyway.”

You sigh again. “Yeah, unfortunately I think that’s probably gonna be the case.”

“Yay corporate grind!” she responds sarcastically, and you laugh again. “Anyway, I have to go now, but keep me updated. And good luck on Monday, you’re gonna kill it!” The two of you say your goodbyes and hang up, leaving you alone in your apartment again.

You allow yourself Saturday night to wallow in self pity - you’re too exhausted from last night to leave your bed anyway. You light some candles and crawl under the covers, listening to your saddest playlist as you watch the shadows cast by the tea lights dance across the ceiling. You take a few deep breaths and try to bring yourself to accept that your night with Kendall, as memorable as it was for you, will not be developing into anything more. You will likely never see him again, but there will probably be other fun nights with other fun men. It’s a shame that you’re not very good at convincing yourself.

Sunday comes and you force yourself to get out and enjoy the day. You take a long walk through Central Park, listening to music, taking photos, and sipping on the warm drink you picked up on your way over. You hate yourself for being upset when you return home in the afternoon to find no post-it note, letter, or Kendall waiting there for you. ‘Stop being so fucking delusional,’ you think to yourself. You’re going to be working with some of the harshest, no-nonsense people in the city starting tomorrow, you need to grow up and leave the teenage fantasies behind. You make a resolution to throw yourself into your work from day one. Time to get serious.

You wake up early Monday morning, wanting to look your best for the day, but also unable to sleep in when you’re feeling this anxious. You get ready and make your way to work completely on autopilot; you’re not really sure how you got there, but somehow you find yourself in the building lobby of the Waystar office at 8:30am.

You check in with the security guard and then stand around awkwardly as he calls upstairs to have someone come greet you. A few minutes later, you hear your name being called and turn to see Jess Jordan, the woman you had interviewed for the job with, approaching you from the other end of the lobby.

“Welcome to Waystar,” she smiles as she shakes your hand. “We’re really excited to bring you on board.”

“Excited to start,” you smile back. You had only spoken to Jess on the phone and are surprised to see how young she is - close to your age and if not, only a bit older.

“Let’s get you upstairs then,” she says as she leads you over to the elevators. “I have to say,” she adds, turning to you after pressing the call button, “I’ve been so eager to actually meet you ever since I read your letter of recommendation.”

You look at her, confusion clear on your face. As far as you know, your letter of recommendation was nothing special. It written by your college economics professor, who had suggested you apply for the role when he heard about the opening through business connections. You weren’t sure you were qualified, but he convinced you to go for it after informing you that working at Waystar would open you up to endless job opportunities for the rest of your career. So, you applied, and he had sent your letter of recommendation over separately. He wasn’t exactly the warmest man though, so you really doubted that he would gush about you in his letter or anything.

She laughs lightly. “Sorry, that must sound weird,” she says, before explaining that she graduated from the same college as you and also had the same economics professor. “I did everything I could to get on that man’s good side, but nothing worked. It seemed like he hated everyone. When I read your recommendation letter and saw it had been written by him… I knew we had to hire you. It takes a special kind of person to get a man that bitter and miserable to say such good things about them.”

You shake your head in disbelief. “Oh… I mean, I never read the letter so I didn’t know what he said but… wow yeah, I wasn’t even sure if he actually liked me. I just thought he’d say I was acceptably competent or something.”

Jess smiles. “Well he seems to think you’re much more than competent. He said we’d be stupid not to hire you.” The elevator door opens and the two of you step inside. Jess pushes the button for the 67th floor.

“So I know the job description was vague,” she says as the elevator begins its ascent, “but I appreciate you signing the NDA before hearing the concrete details of the role.”

You nod. You figured all corporate jobs were as nondescript as the one you were offered, but now you guessed that this one might come with a little more classified information than most.

“We’ll start the basic training today, but first I need to warn you… You’ve come at a, um, an interesting time.” She pauses, watching the floor levels increase rapidly as the elevator swiftly rises. “There’s been a bit of… bad press this past weekend, and managing it is going to be our main focus for the foreseeable future.” You can tell that Jess is choosing her words very carefully. Whether that’s to protect you or the company, you aren’t sure.

The elevator doors open and you enter an open and light but depressingly grey office space. The place is filled with glass and large windows, but it feels like the colour scheme was chosen to remind you that this is a place of work. The extraordinary view of Manhattan is not to be enjoyed.

Jess walks you past reception to a desk situated outside a large, glass walled office, and informs you that this will be your workspace. You briefly acknowledge it before returning to the previous subject.

“Is it alright if I ask what kind of bad press?” you inquire hesitantly. You’re not sure if you’re privy to that kind of information on your first day, but if it’s already in the news and you’re going to be directly working with people handling the issue, you’ll find out all the dirty details eventually; may as well know now.

She sighs. “Yeah, just…” she looks around to check that no one is listening, and then pulls up a chair to sit down at your desk with you. “I don’t want this to completely turn you off the job before you’ve even started,” she says in a low voice. “It’s a good place to work, there’s just been some… slightly depraved individuals who have sat in high positions.”

“Okay,” you say as nonchalantly as you can manage. You don’t like where this is going.

She continues. “New York Magazine published an article this weekend, alleging that some Waystar executives have committed some… um… pretty horrendous acts, and others worked to cover them up.”

Fuck, you really don’t like where this is going. “And those incidents were…?” you ask, trying to approach the topic as tactfully as Jess is presenting it.

Jess looks at you and hesitates before sighing. “Um… theft… sexual assault… some deaths…”

You stare at her blankly. What kind of fucking company are you working for? Why would your professor recommend you for this?!

She sees the look on your face and you know she can tell exactly what you’re thinking. “I know I know, it’s… really awful stuff. This was back in the 90s though, and it was only a few individuals in one section of the company who fostered that kind of environment. I promise, you’re not going to experience or witness any of that here.”

You nod. You believe her, but learning that the company you work for turns a blind eye to the vile acts of its executives isn’t exactly what you were hoping to hear on your first day.

“We haven’t lost you already, have we?” Jess looks at you questionably.

You shake your head no, reminding yourself of the salary you desperately need, as well as what your professor said about this job having to power to present you with endless opportunities.

“Nope, I’m still here,” you assure her.

Jess breathes a sigh of relief. “Okay, great. Let’s get started with training then. First off, do you know anything about the Roys?”

“Oh — um,” you stutter. Fuck, you didn’t think there’d be a test on the first day. You vaguely remember your professor mentioning the Roy name, but all that’s coming to mind right now is that one of them started and still runs the company. “I mean, uh, not real—“

“Don’t worry,” Jess cuts you off. “I wasn’t expecting you to. Honestly, I’d probably think it was a little weird if you did know a lot about them.” She smiles at you and you laugh lightly in response. You’re starting to really like her.

“Just so you have the basics,” she continues, “the founder and CEO of the company is Logan Roy. He has 3 kids— well technically 4, but really it’s 3— who all work at Waystar, though their roles tend to change frequently, so make sure you’re staying updated on who is doing what.”

You nod in acknowledgment, burning into your brain the image of some billionaire nepo-baby yelling at you because you forgot which job they were working that week. You definitely don’t want to go through that so ‘stay updated on the Roy kids’ roles’ is added to your mental checklist.

“Some of the top level executives you’ll come across pretty often are Gerri Kellman, she’s the general counsel for Waystar, Frank Vernon, who’s the chairman of the board, and Karl Muller, the CFO. You’ll meet Karolina and Hugo this week too, they’re in charge of PR and Communications so… we’re gonna be seeing them a lot.” You do your best to commit each name and title to memory.

“Those are the basics of who you need to be scared of,” she jokes, and you smile in return. It’s a relief to know that you’ll be working for someone who can acknowledge how intimidating this environment is. “So let’s talk about your actual role now. As you know, your official title is administrative assistant, so your core responsibilities are going to be assisting me in my more basic tasks so I can focus on the more complicated stuff with our boss.”

You look at her questioningly. You were under the impression that Jess was some type of executive and you would be her assistant. “Oh… so wait, who’s our boss?”

She sees your surprise and a look of realisation flashes across her face. “Oh, I’m sorry, I guess I never explained what my role was. I’m the executive assistant for one of the Roys. He’s the Waystar COO, so while you report to me, I also report to him, so you’ll technically be working for him as well.”

You nod but don’t say anything. After your experience with the handsy creep at the dive bar on Friday night, you really don’t feel great about working closely with an upper level executive at a company where sexual assault runs rampant. The fact that he’s the CEO’s son makes you even more nervous that any misdeeds of his will be easily forgiven.

Jess must sense your hesitation, because she reassures you immediately.

“Oh he’s not like that, I promise, and those issues were pretty much contained to the Waystar cruise line. Kendall can be demanding and… erratic at times, but he’s generally a good guy, you don’t have to worry about him doing anything like that.”

Your ears perk up at the name. Kendall? That’s a weird coinciden—

“Yeah, fine Frank, if we’re really fucking backed into a corner I can make it work, but I don’t see why we’re adding me to the fuckfest when this might be the one thing Rome could actually handle alone.”

Your heart stops cold. His deep voice cuts through the stagnant office air like a knife, and for a moment, you wonder if you’re imagining it. There’s no fucking way this is actually happening, right? This isn’t real, this can’t be fucking real.

But you aren’t imagining it, and it is real. Kendall turns the corner a moment later, flanked by two older executives, and upon seeing him, your heart jumpstarts back to life. You feel it beating so fast that you wouldn’t be surprised if it burst out of your chest and flopped out onto the office’s grey carpeted floors.

“Oh here he is now.” Jess stands up from the desk and you do the same, watching him as if in slow motion. He hasn’t seen you yet and you’re dreading the moment he does. God, what you wouldn’t give to be able to crawl inside of your own skin and hide right now.

“Morning Kendall,” Jess greets him as he approaches, and he responds with a simple “Hey Jess,” before his eyes fall to you.

It’s quick; if you weren’t looking for it you probably wouldn’t have caught it, but for a millisecond, a look of pure horror crosses Kendall’s face. The speed in which he neutralises his expression is extremely impressive.

You’re vaguely aware that Jess is introducing you to Kendall and the other two executives, but you can’t bring your eyes to leave his face, and his don’t leave yours. He says something along the lines of “Nice to meet you, we’re excited to have you join the team,” as he shakes your hand, but it feels like he must be speaking in another language, the sentence sounds so foreign and unnatural to you. You wonder if he can hear you repeating the word “fuck” over and over in your head as you stare at him and absorb the situation. Kendall is here. He’s your boss. He’s Kendall Roy of Waystar Royco. The entire thing feels ridiculously surreal. You feel nauseous.

Your attention is brought back to the group when the older woman who had been walking with Kendall offers her hand for you to shake. You hear her say the words “legal jargon,” and you come to the conclusion that this must be Gerri. The balding man on the other side of Kendall extends his hand to you next and gives you a warm smile while repeating his name (“So nice to meet you, I’m Frank”). He must think you look very overwhelmed, considering how kind he’s being to you, and he’s right, you are overwhelmed, just probably not for the reason he assumes. Gerri and Frank end the conversation by welcoming you to Waystar. Kendall just nods in agreement.

Jess turns back to you as the group walks away, Kendall giving you one last intense look before he turns another corner with Gerri and Frank.

“Okay, why don’t we get started with the scheduling system?” she says as she sits back down, and you sit down beside her. Jess logs into your computer for you while you silently plead with your heart, begging it to stop beating at the uncomfortably rapid pace it’s adopted.

‘Oh my god, what do I do?’ you think. ‘Should I just get up and leave? I can’t work here!’ You feel yourself spiralling, the panic of the moment really beginning to set in. You force yourself to take a few deep breaths before you start having an anxiety attack in the middle of the Waystar offices and try to focus on the scheduling system Jess is pulling up on your computer. The way she has the calendar organised, for some reason, helps you calm down slightly. The neat rows and coordinated colours brings you some sense of balance, and you feel your heartbeat finally start to slow down.

You soon begin to actually absorb her teachings as well and realise how ridiculously simple your tasks are. It’s pretty much just organising Kendall’s calendar and scheduling his appointments and meetings. Jess will be the one assisting him with all the more complicated tasks, you just need to lay the groundwork so he has a general layout for each week. Are you actually going to be making almost $100k a year to do THIS? Suddenly working with the guy who ghosted you seems more like a complication as opposed to an outright dealbreaker.

This feeling lasts less than an hour. As Jess is going over how to use the office phone line with you, Kendall suddenly reappears in front of your desk. You and Jess both look up, and he wastes no time introducing a way to get you alone.

“Jess, have you shown her the photocopy room yet?”

Jess shakes her head no. “We’re just going over the extension codes now, and then I was going to—”

Kendall cuts her off. “I’m heading down there so I can show her.” He begins to walk away and Jess nods at you, indicating that you should follow him. Your heart rate immediately picks up again. Time to get this over with.

Kendall walks through the busy office to the elevator, and you rush to catch up. It opens just as you arrive at his side and the two of you enter. No one else takes the long ride down to the basement with you, but you don’t move or speak or look at each other the entire time. It’s the most painfully silent and uncomfortable minute of your entire life, but eventually the doors open and Kendall is striding down a concrete hallway to an inconspicuous door. He opens it and lets you enter first before shutting it quickly behind him.

“Jesus Christ…” he mutters as he crosses his arms and looks over to you. You’re standing in the centre of the room, arms crossed as well. It’s taking all the self control you have to not start pacing back and forth between the copiers to keep the anxiety building in your throat at bay. You stare at each other, neither of you speaking until you can’t play it cool anymore. You say what you’ve been wanting to say to him since Saturday. It holds much more weight now though.

“What the fuck, Kendall.”

You know it’s ridiculously unprofessional that those are your first words to your new boss, but as far as you know, there’s no workplace rulebook that applies here. You’d be shocked if HR had established guidelines on what to do if a boss and subordinate have a one night stand only days before beginning to work together.

“I, uh…” Kendall hesitates as he bows his head, his shoulders tensing up. “Yeah, I’m sorry, I should’ve asked for your number before I left.”

You can’t help from emitting a sharp laugh. “What?!” you ask, absolutely bewildered that this is what he’s choosing to start the conversation with. Is he joking? “Do you actually think that’s anywhere close to being the most important thing we need to discuss right now?”

He looks down again and shakes his head. “No, you’re right,” he sighs, exasperated. You watch him start to pace until he suddenly crosses his arms tighter across his chest and lifts his head, beginning to stammer. “I uh - I just - I don’t know what the fuck I’m supposed to say! I wasn’t expecting to see you again, and definitely not in this fucking situation.” His tone is harsh now, and the shock of it has you taking a step back. This is not the funny, charismatic guy you met on Friday night.

He turns away from you as his hand reaches to rub the back of his neck. When he turns back to face you, the stress of the situation is evident in his expression. He takes a deep breath. “Sorry, fuck, I just… this isn’t happening at a great time.”

You don’t say anything. No words are coming to mind, but you’re also not sure you really need to speak. You’re not the one who withheld a huge portion of your identity from him.

“Look,” he sighs, and he leans his shoulder against the wall. “It’s… it’s rare that I get to detach myself from the Roy name. I saw an opportunity to do that with you, and I took it. I… I wasn’t thinking about what would happen after.”

You nod, partly in response to his explanation, but mostly because he just confirmed what you had been worried about all weekend. He really did just see you as a one time thing. If you hadn’t been standing there as his new employee when he came to work this morning, you would’ve never seen each other again, and that would’ve been fine with him. Ouch.

“Cool,” you mumble, eyes dropping to the floor as you nod again. “Cool, so hanging out with me was just a like… little social experiment for you, yeah? See what it’s like to be a commoner for a bit?” You hate how bitter you sound, but you’re hurt and you feel stupid. You saw your time together as a moment of real connection, but he saw it is a fun opportunity to play make believe. You were just a toy in his little game of normality, and he was content to discard you once playtime was over.

“No, no,” he uses his shoulder to push him off the wall. “I just uh, I just wanted to have a normal fucking conversation for once. I didn’t plan for our night to go…” he trails off, taking a deep breath before continuing. “For it to go where it did. I, I wasn’t expecting to like you as much as I d-“

“Don’t,” you interrupt. You don’t want to hear it, it’s just another thing that will make this entire situation messier and more confusing than it already is. “Let’s not go there, there’s no point.”

He looks at you for a moment, his mouth slightly open, still wrapped around the sentence you stopped him from finishing. He closes it after a second but continues to look at you, his eyes sad.

“I really am sorry,” he adds. “You have to understand, there were no good options for me after I left yours on Saturday.” His hand reaches to rub the back of his neck again. “I was uh, I was pretty sure you'd hate my fucking guts no matter what… whether I ghosted you or told you who I was.”

You scoff a little. He’s right in some sense, you would’ve been upset either way. “Yeah, that’s probably true. But maybe we could’ve avoided this morning’s fun little run-in if you had been honest with me from the get go.”

He scoffs too. “Yeah… fuckin’ hindsight I guess…”

You both stand there silently for a moment, arms crossed, eyes on the floor. At least you now have some sense of closure regarding his disappearance, but you still have to address the bigger issue.

“So… what now?”

Kendall shakes his head and stuffs his hands in his trouser pockets as he thinks. “Uh… I guess we uh, come up with something for you to tell Jess regarding why you can’t fulfil the duties of the role.”

“Wait, what?” you ask. You were expecting him to say something along the lines of “let’s forget it happened, fresh start, etc.,” not nonchalantly instruct you to quit on your first day.

“Well this already isn’t a professional relationship,” he says coolly, gesturing between the two of you. “I can’t have more pers— I can’t have any personal stress here, and you’re a uh… distraction.” He averts his eyes from you as he gives an apathetic shrug.

A mix of anger and panic begins to build in your chest; your entire world has fallen apart around you in a matter of minutes. Your one night stand ghosts you, reappears as your new billionaire boss, and now tells you that the job you worked your ass off in college to get, the job you literally uprooted your life for, is no longer yours. Your fight or flight instincts kick in, and you’re surprised to learn that your body is choosing to fight.

“No.”

He looks up at you, an eyebrow raised as he crosses his arms again. “What?”

“I said no, Kendall. I moved to the city for this job. I worked fucking hard to earn this job. And I’m not like you, I have bills to pay and I can’t afford to spend months finding a new job.” Kendall looks away from you as you say this last comment. You feel bad pulling the ‘you have money and clearly forget that others don’t’ card, but it’s true. The rent for your little studio is so ridiculously high that you’ll be homeless by the end of the month if you don’t have a steady income.

“If you want me gone, you’ll have to fire me,” you continue, “and I know you definitely don’t want to do that, because then Waystar will need to pay me a fuck load of hush money to ensure that I don’t shout from the rooftops that the boss’ son fucks and then fires his assistants.” Kendall’s eyes flash back to you and his eyebrows knit together. “And I'm sure that would look really good coming out right after a massive scandal.”

Internally, you can’t believe that these words are coming outof your own mouth. Are you blackmailing him? No, you don’t think so… you’re pretty sure that you’re just defending your right to keep the job you earned. Whether you’re justified in threatening him or not, you’re proud of yourself for standing your ground. Maybe it’s just easier to not be a pushover when your livelihood actually depends on it. But either way, considering what you told Kendall about being a people pleaser a few days ago, you’re sure that he wasn’t expecting this kind of pushback.

Kendall stares you down. You feel like his eyes are boring holes into yours, his gaze is that intense. It takes everything you have to stop yourself from giving in and breaking eye contact. You don’t though, you look into his brown eyes and search for the connection you felt to them on Friday. For a moment, you think you see it; a hint of something resembling warmth flashes across his gaze. Just as suddenly as you saw that flash of emotion, he drops his eyes from yours.

“Fucking hell,” he mumbles. He bows his head again, shaking it slightly in disbelief. “You really want to work for someone you’ve slept with? You’re 100% okay with that?” He looks at you quizzically.

“I’m not a child, I’m capable of separating personal emotions from work.”

You’re not actually sure if this is true - you’ve never had such a complicated relationship with someone you’ve worked with before, but at this point, you’ll say anything to keep your job. “I can be professional if you can.” You eye him intently.

Kendall looks taken aback that you’re turning this around on him now. He casually shrugs but begins to stammer again. “Uh, yeah, I uh, it’s fine with me if it is with you. Just… you know, let’s keep it professional.”

You nod. He gives you another intense look, as if he’s offering you one last chance to back out, before he sighs. “Okay well, uh, welcome to Waystar I guess.” He clears his throat before extending his hand to you.

You scoff slightly; the moment is such a weird redo of you two meeting each other on Friday night and again this morning, but you quickly push your deja vu to the side and accept the gesture.

“Thank you,” you say civilly, returning his firm handshake. You do your best to not focus on the feeling of his hand wrapped around yours again, but you aren’t successful.

Kendall drops your hand and stuffs his own back in his trouser pockets, stammering again awkwardly. “I uh, we should uh, get you back up to Jess,” he suggests. “There’s a, yeah, there’s a lot you need to learn.”

You stand up straight. “Yes sir, Mr Roy,” you say, giving him a salute as you head toward the copier room door.

You immediately kick yourself internally for being so weirdly cringe. What the fuck was that? You tend to act awkwardly when you’re feeling awkward, and as this is one of the most awkward situations you’ve ever been in, you seem to have set a new record for embarrassing yourself.

It isn’t all bad though. It seems that your bizarre behaviour has helped break the tension, because Kendall smirks and places his hand on the door to stop you from leaving. “Jesus Christ” he chuckles. “Don’t ever do that again, we don’t let fucking losers work here.”

Relief washes through you. He’s reappeared. The man you had so much fun with on Friday night is, to some degree, back. You immediately start to feel more optimistic about having a career at Waystar - this is a version of Kendall that you think you’d enjoy working for.

“Are you sure? Your taste in music tells me otherwise,” you say sincerely, and you give his shoulder a condescending pat.

Kendall breaks into a full smile, clearly loving the banter, before he catches himself. You both know you can’t continue acting like this once you go back upstairs. He clears his throat. “Let’s keep the chumminess to a minimum, yeah? I’m still your fucking boss,” he says sternly, but you can see the warmth in his eyes and know that the warning isn’t 100% serious.

You nod silently and smile, showing him exactly how agreeable you can be, before gesturing toward the door he still has his hand on to stop you from opening it. “Are we going?” you ask. Any longer here and it’ll be obvious that Kendall was not just showing you the copier room.

“Oh, uh, yeah, let’s go,” he responds, quickly removing his hand from the door before opening it for you. The elevator ride back up to the 67th floor is silent again, but not nearly as uncomfortable. ‘Okay,’ you think. ‘This is manageable. It’ll be weird for a little, but eventually, how we met is just going to be a funny memory. You can do this.’ You actually believe your internal pep talk this time.

————————————

Kendall tries to get back into the regular swing of his work day, but everything feels disjointed. He and his siblings released a statement about the cruises scandal this past weekend, and it seems to be keeping things somewhat under control, but the shareholders are now getting spooked by the bad press. Waystar is in damage control mode and he’s been instructed to head to England so he can convince his mother to keep her company share, which might help prevent a company takeover. He really doesn’t want to go back to England; the thought of returning to the scene of the (literal) crime has caused a knot to form in the pit of his stomach, and you sitting at your new desk right outside his office isn’t helping him feel any steadier.

Eventually the sun starts to set, and the office starts to empty. Kendall looks up from his computer at some point and sees that you’re no longer sitting across from Jess. He calls her into his office and once she’s shut the door behind her, he doesn’t hesitate to ask if you’ve left for the day. Jess checks her watch.

“Yeah, I mean it was well after 5 when she left. She did show up early and we’ve done a lot today, so I sent her home…” she looks at him quizzically. "Is that… okay?”

He scrambles to hide his disappointment. He was hoping to get another moment alone with you before he leaves for England tomorrow. He’s not sure why, it’s not like you two have anything else you need to discuss, but he’s disappointed that it’s not even an option anymore. “Yeah yeah, that’s fine. So, uh… how’s she doing so far?” He presents the question as a boss wanting to know if his new employee is worthy of the job, rather than as someone who knows how nervous you were for today and is curious to see how you held up.

“Oh fantastic,” Jess nods, answering without hesitation. “She’s a really fast learner, we’re like, way ahead of schedule.”

“Oh, good,” Kendall says nonchalantly. He’s surprised. Pleasantly surprised, but surprised nonetheless. “Uh… yeah, good. So you think she’ll be ready to fully take over your duties by the time I’m back on Friday?”

“Yeah, I mean she might even be ready by tomorrow. We don’t have much left to cover, but I’ll shadow her until you’re back.”

He nods. A feeling resembling pride washes over him as he listens to Jess recount your competency. He quickly tries to brush the feeling away. It's not like he’s ever felt ‘proud’ of Jess for just doing her job. “Okay, thanks. I’ll uh, I’ll keep you updated while I’m over there,” he says, dismissing her.

She nods and starts to head for his office door before he stops her. “Oh, hang on… just while I’m remembering, could you uh, forward her contact info to me?” This isn’t an abnormal request — executives are usually contacting their assistants when they’re out of the office — but he still feels awkward asking.

Jess doesn’t seem to notice though, she just says ‘okay’ and heads back to her desk. A minute later, his phone buzzes beside him as Jess’ message containing your number, email, and address is delivered to him. He ignores the text until Jess has left for the day, and then he picks up the phone.

He quickly crafts and sends a text to you, trying not to overthink it. Standard employee-employer messages shouldn’t be anxiety inducing, and he pretends that sending this text to you isn’t. He sets his phone down and turns his attention back to his computer.

————————————

Back at your apartment, you’re in your tiny kitchen making your favourite comfort meal - you really need something soothing after the rollercoaster of emotions you experienced today. Your phone lays face down on the kitchen counter beside you. You hear it buzz gently under the sound of your music playing in the background, and you turn it over, glancing at it while you stir your food on the stove. It’s from an unknown number, but your heart flutters as you read it.

“Hey, it’s Kendall. Good job today. Really looking forward to working with you.”

Chapter Text

“Hey, looking forward to working with you as well. Enjoy England!”

Kendall sits alone at the back of the Roy jet, baseball cap pulled low over his forehead as he stares at your text. He’s looked at it so many times over the last few days that he thinks there may be a permanent imprint of it etched behind his eyes.

He rereads it again, wishing your exclamation point had been assigned to the first sentence rather than the second. That’s what you should be more excited about - working in close proximity with him every day, not him having a horrific few days on the other side of an ocean.

Obviously he knows you aren’t aware of what this trip was for him. No one would guess that a few days in England with his family would make for one of the most miserable weeks of his life, or that he would board this plane feeling more alone and hopeless than he ever has before. The trip coming to an end is alleviating, but only partly. The shame he carries with him about the night of his sister’s wedding, the heaving guilt that is constantly sitting in the middle of his chest, has grown exponentially since he left New York. Seeing the dead kid’s house, meeting his family, being unable to confide in anyone, not even his own mother, about it… it’s bleak. It’s so fucking bleak and he’s now convinced that he will be living with this level of anguish for the rest of his life. It’s the loneliest feeling in the world.

The pilot announces that they’ve begun their descent into New York. Kendall locks his phone, the bright light from your text disappearing to black. It’s still there though, right behind his eyes.

————————————

Your week goes relatively smoothly, considering how it began. You and Jess finish your training by Tuesday afternoon, and the rest of the week is spent mostly just preparing you to fully enter the Waystar world. You meet a few other important executives, as well as their assistants, and you’re pleased to find out that you are definitely not the least qualified in the bunch. One assistant, Greg, who Jess tells you is actually a Roy cousin, stumbles awkwardly through your short interaction with him, using words he clearly doesn’t know the meanings of multiple times. He reminds you a bit of a newborn giraffe in terms of physical build, grace, and intelligence. If he can survive in this world, then you definitely can.

When Friday rolls around, you’re surprised to realize that you actually feel pretty good about your future at Waystar. You understand your tasks, are getting used to the routine, and no longer feel overly intimidated by the workplace. All that’s left to do now is learn how to maintain a professional working relationship with a man who has seen, touched, and been inside your naked body.

Ugh. You have until Monday to deal with that though, a full two days to relax and reset before the real work begins. No need to stress yourself out about it too much yet.

It’s almost 7pm when Jess tells you you’re good to head out for the weekend. “9-5 isn’t really a thing at Waystar, especially when you’re an assistant,” she explained on Monday, so she’s been dismissing you later and later every night this week to prepare you for what’s to come. For now, you don’t mind too much. It’s not like you have any friends to make plans with or any money to do anything exciting with. The extra one or two hours are usually just spent at your desk while you and Jess exchange life stories, so you enjoy the opportunity to socialize. You can definitely see it becoming a frustrating expectation in the future, but you’ll cross that bridge when you get to it.

You grab your jacket and bag from your desk as you prepare to head home, the knowledge that you won’t be back here tomorrow giving you a lightweight, relaxed feeling. After saying goodnight to Jess, you head toward reception and push the call button for the elevator. The office is quiet, but not as quiet as you would expect it to be at 7pm on a Friday night.

‘This is part of why the Roys are billionaires,’ you think to yourself. ‘Running themselves and everyone around them into the ground.’

As if conjured by your insubordinate thoughts, the elevator doors open, and you’re suddenly face to face with Kendall and a man you’ve only seen in the many Waystar training videos you’ve watched this week - Logan Roy.

You take an automatic step back to give them space to exit the elevator, clutching your jacket close to your chest as if to protect your core from an enemy attack. You and Kendall stare at each other for a second, both of you looking like deer in headlights. He was clearly not expecting you to be at the office this late, and you were not expecting him to be back in New York this early. The surprise appearances the two of you keep making are never ending.

Kendall clears his throat as his dad exits the elevator first. Logan doesn’t even look your way until Kendall speaks and gestures to you.

“Uh, Dad, this is one of our new hires. She’s just started working under Jess as an administrative assistant.”

Logan stops and gives an uninterested “oh” as he turns to you and extends his hand for you to shake. You return the gesture and introduce yourself, telling him what a pleasure it is to meet him and work for Waystar.

“Good to have you aboard,” he nods.

You’re not sure where it comes from, maybe your lifelong need to be liked, but the urge to say nice things that you don’t actually believe suddenly takes over.

“Thank you. Really, it’s an honour to work for such a longstanding company. I’ve always admired Waystar’s consistency; how you’ve been able to maintain such a steady brand presence and image for decades is beyond impressive.”

Your praise has piqued Logan’s interest ever so slightly. “Glad you see it that way,” he remarks approvingly. “Consistency is what keeps our customers loyal, it’s crucial to our success.”

You nod. “I completely agree, and your track record in earning the consumers’ trust and then keeping them loyal… it’s very admirable.”

“Well, thank you,” Logan responds. “Hopefully you'll contribute to maintaining that consistency during your time here.”

“Absolutely, any way I can. Maybe I’ll have to adopt my own Waystar uniform or something so I can get into the right mindset.” You give him a sweet smile with your joke, internally hating yourself for being such a kiss-ass.

To your surprise, Logan emits a light chuckle and gives your arm a grandfatherly pat. “Good attitude,” he smiles, “that’s what we need around here.”

Your smile grows at his reaction. You may be a kiss-ass, but this feeling of relief, knowing you managed to not completely fuck up this interaction, makes it worth it. You suddenly remember that Kendall is also present and your eyes quickly flash to him, hoping you’ll be able to see what he thinks of your conversation with his dad.

Though you may have forgotten he was there for a moment, but you’re painfully aware of it now. His gaze is fixated on you, and he doesn’t look impressed. He looks… you’re not sure there’s an exact word for it, but the closest one that comes to mind is mystified. Not like he’s fascinated by you, but more like he’s looking at a math problem that he can’t seem to figure out. Intense concentration mixed with deep confusion and a sprinkle of frustration.

You’re suddenly desperate to end the conversation. “Well I won’t take up any more of your time Mr. Roy, but it was a pleasure to meet you.”

He gives you a nod and another pat on the arm. “You too,” he says, and then he begins to walk away. Your gaze flashes back to Kendall, whose expression hasn’t changed from the last time you looked at him. He stands there for a second, watching you as you press the elevator call button again and not saying anything when you finally look up and hold his eye contact. His brows are slightly furrowed and you think he’s bound to make some type of comment, but he doesn’t. He just walks away, following his dad deeper into the office and leaving you to stare after him.

The elevator dings behind you as it arrives, snapping you back to attention. You stumble inside, fidgeting anxiously with the buttons of your jacket as the doors close and you begin your speedy descent to the ground. You no longer feel like you have all weekend to relax, you know you’re going to spend the next two days doing nothing but replaying that short conversation over and over again in your head. What did you do to warrant that kind of reaction from Kendall?

Your commute is always cramped and tedious, but it feels 10x busier and longer today. You spend the entire subway ride with your headphones in your ears but nothing playing, which you don’t even notice until you get off at your stop - your mind has been making enough noise on its own. Eventually you reach your street and start to feel like you might be able to relax; you just need some food and TV to distract your brain. Just as you’re approaching your building’s front door though, your phone buzzes in your pocket. You pull it out and your heart stops.

Kendall Roy
2 Text Messages

You freeze in your tracks, your fingers rushing to unlock your phone. You don’t want to give yourself time to theorize what his messages might be about so you open them immediately.

“Have to say, that was both impressive and unsettling to watch.
You didn’t fuck him too, did you?”

A shocked laugh escapes your mouth. Definitely not what you were expecting to read. You begin typing a response as you push the front door of your building open with your shoulder.

“Lol no, but you should still be worried. Clearly I’m naturally gifted at winning over members of the Roy family.”

You hit send before you can overthink it. His second text was the furthest thing from professional, so there should be no issue with you playing into the banter that he started.

Your phone buzzes again before you’ve even entered your apartment.

“Oh I am, anyone who can tame a Roy needs to be taken seriously.
Gotta keep an eye on you before you charm your way into my job next.”

You pull your jacket off and then toss your bag onto the couch, flopping down beside it as you smile at your phone.

“I was thinking of just taking your company shares actually. I’ll let you keep the COO title and office, it’s the least I can do.”

You know that texting like this is dangerous. It gives you and Kendall the opportunity to continue developing a personal relationship when you should be solely focused on your professional relationship. But… fuck, you really like him. You two click so seamlessly; talking to him, joking around with him, being intimate with him… it all comes naturally. If you’re going to be in each other’s lives and can’t do the physical intimacy part, you should at least get to have a little bit of emotional intimacy. It wouldn’t make sense to completely deprive yourselves of your connection, right?

That’s what you tell yourself when your Friday night texts to Kendall turn into Saturday morning ones, and then into a conversation that continues until the end of the weekend. The banter is still present, but your messages to each other also take on a more sincere tone. Kendall is almost always working in some capacity so his texts arrive irregularly, but when he does respond, he surprises you by actually seeming interested in how you’re spending your weekend. You give him little updates of your adventures around the different Manhattan neighbourhoods, and he makes jokes about you being a lame tourist, but he also wants to know your opinion of his city and what you’ve been most interested in seeing. The urge to make a “you should show me around” comment feels impossible to resist, but you manage to hold your tongue. It would be hard to pretend that your text conversations have been completely innocent after making a suggestion like that.

When Monday arrives, you actually find yourself excited to be fully working with Kendall rather than nervous. Continuing to flirtatiously tease each other at work is obviously out of the question (especially when everyone thinks you’ve only interacted once for less than 10 minutes), but you’re just happy you get to be around him. Your text conversations this weekend have fully cemented your fondness for him. His wit, his intelligence, his perceptiveness, you love it all, and the more you learn about him, the more you want to continue learning. It’s a dangerous realization to come to, but you tell yourself that it’s not a big deal. As long as Kendall stays professional, you can too.

You get to the office early, and Jess is, of course, already there (you’ve learned that you can show up as early as you want, but Jess will still be there first). You begin the day by reviewing Kendall’s general schedule for the week together, and you’re surprised to learn that he’s going to be crossing the pond again, but this time to go to Scotland for an event being held in his Dad’s honour. God, is he ever actually here?

Today, he is. He shows up a little after 9, wearing the stern expression that you’re still getting used to. The confident smile that crinkles his eyes, the smile that initially attracted you to him, is hard to picture when you watch him in his natural habitat. He gives you and Jess a neutral greeting as he strides into his office, and you begin to understand why one of your first impressions of him was that he belonged in any room he entered. It’s probably hard to not feel that way when you’re the prince of an empire and can see the effect your presence has on others. Everyone in the room sits up straighter when Kendall walks by, and you notice yourself do it too. The last thing you want him to think is that you aren’t taking this job seriously, so you remind yourself to always look like you’re hard at work.

Kendall has a meeting with some of the other top executives shortly after arriving, but it’s not long until he’s back in his office and calling you and Jess in.

“So let’s uh, go over the week,” he says, looking down at the paperwork on his desk as you and Jess sit down opposite him. “And then Jess, I want to make some changes to the script for that… recording studio bullshit I have to do for the uh, Dundee thing.” He looks up at her at this point, but his eyes haven’t travelled in your direction even once.

“For sure,” Jess nods before turning to you. “Why don’t you take it away with the main points for the week.”

“Oh yeah, um, sure,” you say as you shuffle through your documents and then begin to summarise the central tasks Kendall has this week. Board meetings, lunches with shareholders, calls with Scottish reporters about Logan’s upcoming Dundee celebration, his expected attendance at the preview for a play that his brother Connor is financing, etc. Once you get through all the boring stuff, Jess fills him in on the more nuanced and personal information he needs to know, which includes mentioning the ridiculously long email that Connor sent about Kendall’s ‘enthusiastic presence at the preview being of the utmost importance in order to set the tone for the play’s run.’ Kendall sighs.

“Jesus fuckin’ Christ,” he mutters, shaking his head slightly. He looks up at Jess - he hasn’t made eye contact with you even once yet. “Could you get him off my back somehow, like, I don’t fuckin’ know…” he trails off, thinking of what it’ll take to get Connor to shut up.

You jump in. “We already arranged for the playwright - Willa?” You look over at Jess to confirm the name, and she nods. “To receive a bouquet from you the night before the preview, but we could include the entire cast if you’d like? Make it a bigger gesture?”

Kendall finally locks eyes with you. “Oh, yeah, that’s, uh… that’s good, go ahead with that. Please,” he adds before looking back the pile of documents on his desk. “Is that everything?” he asks as he looks up at Jess, his eyes briefly flashing in your direction.

“Yep,” she nods. “Do you want to start making those changes to your script now?”

With your role in the meeting being complete, you gather your things and leave Kendall’s office, settling back in at your desk on the other side of the glass wall.

————————————

Jess pulls out a physical copy of the script she’s workshopped for Kendall. Her draft is good, but Kendall knows it needs to be more explicitly complimentary toward his father. Gotta do whatever it takes to keep him happy.

“So, what were you thinking of adjusting?” she asks as she scans the page, placing it on his desk between them.

“Oh um, something about him always being there for me, or…” he trails off, his mind elsewhere. “Uh, was it your idea to send flowers to Willa?” He can’t concentrate until he’s confirmed something for himself.

Jess looks up from the page and shakes her head, explaining that you had taken the initiative to write a response to Connor saying how excited Kendall was to attend the preview, and then arranged for a bouquet to be sent to Willa. All Jess had done was given you the go-ahead to send the already-written email, and her permission to order the flowers.

“Right,” he responds, “right, okay, thanks,” and then he directs his attention back to the script in front of him. He can feel Jess looking at him questioningly for a moment, and he knows that what he just did was suspicious as fuck. At Waystar, it really doesn’t matter who had an idea first, it only matters that bad ideas are rejected and good ideas are implemented. Confirming who suggested the (pretty basic) plan to quiet Connor’s cry for attention is not even remotely important, and Jess knows that. Kendall just couldn’t stop himself from hearing more about how you operate. How you took control of the Connor situation, the way you sweet-talked his dad, the fact that, so far, you’ve been more than capable of acting like you and Kendall never spent a night together… it’s bizarre.

“Let’s uh, fuck it, let’s put in something about my dad being there for my, uh… many ups and downs or whatever,” Kendall suggests, hoping to distract Jess from his unusual behaviour. She nods and searches the page for a suitable place to make the addition, and Kendall allows himself a second to look over at your desk. Unfortunately, Jess looks up at him before his gaze leaves you.

————————————

Your week speeds by. Kendall isn’t always in the Waystar building, but the quality of your day multiplies when he is - not just because you like being around him, but also because when you are, you can see that he’s just as aware of your presence as you are of his. You sometimes catch him sneaking glances at you from his office, and he comes out to your desks semi-regularly to make requests of Jess that definitely could’ve been done over the intercom. One day, when you’re settling back in at your desk after making a cup of tea in the kitchen, Kendall gets back to his office from a meeting and notices your drink.

“Those aren’t cheap, you know,” he comments as he walks by your desk. “Teabags are, what, like 3 fuckin’ dollars now? If you’re gonna have multiple every day, we’re gonna have to start taking that out of your pay cheque.” He smirks at you, and you can’t believe he’s actually doing this while Jess is sitting directly across from you. You haven’t seen him ever joke around with her, is this not noticeably out of character for him?

You try to react like a new assistant would with a boss she doesn’t want to disrespect - politely engaged. You laugh lightly (very lightly, can’t have Jess thinking you’re flirting) and smile. “I think it’s more like 20 cents, but okay, I understand. Gotta do what you gotta do to keep this place running.” You shrug good-naturedly (“Nothing to see here Jess! Just being agreeable with the boss!”) and turn back to your work. You think you’ve hidden your connection with Kendall pretty well until Friday night rolls around. You’re just about to head out when Jess calls you over.

“Hey, sorry, can you hang back for a minute?” she asks.

“Uh yeah, of course. What’s up?” You settle back into your chair opposite her, resting your jacket and bag on your lap.

Jess leans forward on her desk and glances around. The office is relatively empty, and no one is seated near the two of you. Deciding that it’s safe to talk, she turns back to face you.

“Well, you’ve been here for 2 weeks, I just wanted to see how you’re feeling about everything so far.”

“Oh, um…” The way she asks the question catches you slightly off guard; this is definitely not a formal performance review, it feels much more like a personal check in. “Really good, actually. Everyone is pretty nice, I think I’m handling my tasks well… yeah, I’m feeling good about it all.” You nod to indicate that you’re done speaking, but she looks skeptical.

“… So everything’s totally okay?” she asks. Again, this doesn’t feel like official Waystar business, and she isn’t presenting the question in an accusatory manner, she seems… concerned.

Your eyebrows knit together in confusion. “Yes, everything’s totally okay,” you nod. “Why?”

She leans forward a little further. “I’ve just… I’ve noticed that Kendall’s been paying… extra attention to you.”

Your heart drops. Fuck. Does she know? Fuck fuck fuck fuck fuck.

“Like I said on your first day, he’s a good guy but he can be a bit, um, unsteady at times, and you know, he’s been a billionaire pretty much his entire life so he isn’t always conscious of the kind of power he holds…” She raises her eyebrows at you as if to hint at what she’s trying to say, but you don’t want to give any indication that you know exactly what she’s been noticing. You give her your best confused expression instead. “I just mean… you can tell me if you ever feel uncomfortable. Sometimes he just isn’t aware that he’s crossed a line that normal people wouldn’t.”

You pretend to finally realize what she’s suggesting. “Oh! Oh no, I haven’t felt uncomfortable at all.” Thinking on your feet, you come up with a valid reason for Kendall’s heightened attention around you. “I just mentioned to him, when he was showing me the copier room on my first day, that I was a little nervous to work here, which was probably a stupid thing to mention to my new boss during our first conversation, but I think after hearing that he’s just been more conscious about me, like, fitting in and being comfortable at the company, so he’s been paying closer attention.” You realize that you’re rambling and hope she assumes it’s because you feel bad that Kendall’s being wrongly accused of harassment. “So no, I haven’t felt uncomfortable at all, but I really appreciate you looking out for me.” You give her a smile of gratitude and she smiles back, seemingly satisfied with your explanation. You breathe an internal sigh of relief.

“Oh, okay good. You’re doing really well so far, I just wanted to make sure that everything else was okay too.” She smiles again and emits a breathy “whew” sound. “Cool, I feel better now. Sorry to keep you behind longer, please, go have a good weekend.”

“Thanks Jess, you too. I’ll see you on Monday.” You give her a little wave and try to stay composed as you make your way to reception while your mind screams at you. Having to act like you’re not freaking out in the elevator as it stops at multiple floors on its way to the ground is a cruel test of self-control, but you eventually make it out. The fresh air that hits your face when you finally exit the Waystar building helps you settle down a little, but not enough to completely erase your sense of urgency. You don’t hesitate in pulling your phone out to message Kendall.

Though you haven’t been texting each other as consistently as you did this past weekend, you haven’t exactly been ignoring each other either. Your conversations are generally innocent, usually just teasing jokes that you can’t make in the office without seeming too friendly (comments a little more intimate than pointing out your excessive tea consumption), but it’s now clear that you weren’t hiding your friendship as well as you thought. You rush to compose a warning text for him.

“Jess commented on you paying “extra attention” to me. We need to tone it down.”

You quickly hit send before re-reading the text. It’s not until it’s already been delivered that you realize that you didn’t mention anything about covering for him, or that she doesn’t seem to be suspicious anymore. It’s no surprise when you receive an incoming call from Kendall not even 20 seconds later.

“It’s okay, I handled it,” you say the second you pick up. You explain your lie about ‘confessing your nerves’ to him in the copy room on your first day, and that what Jess has noticed is just him keeping an eye on you. “She seemed to believe it, so if she asks, just pretend like you’ve become an empathetic person overnight.” You can’t stop yourself from adding in that little dig at the end, it comes too naturally with Kendall.

“Hey, I’ve got the empathy of fuckin’ Gandhi,” he quips. “I let you keep your job, didn’t I?”

You scoff. “For your ego’s sake, I’m gonna let you pretend that I didn’t have you backed into a corner. But seriously,” you add, your voice taking on a more serious tone. “Maybe we need to… take a step back from talking for a bit? Just until we can be friendly with each other less noticeably?”

Your heart aches for itself. Talking to Kendall, joking with Kendall, flirting with Kendall… You’re ashamed to admit that your interactions with him, whether by text or in person, have been the clear highlights of the week. Your conversation with Jess is a rude awakening though, and you think it’s maybe time for you to focus your attention on someone other than your boss.

Kendall is silent on the other end for a few seconds. “Uh, yeah. Yeah, okay. I’ll, fuckin’, uh, I’ll just see you when I get back from Scotland then.”

You want to take it back, you want him to resist, but unfortunately, neither of you does what you want.

“Okay, yeah, I’ll see you next week. Have a good trip and uh, enjoy the play tonight.” Kendall just responds with ‘yeah, thanks,’ and hangs up. You stare at the black screen for a moment, angry with yourself for getting into such a stupidly risky situation in the first place. You allow yourself a few seconds of self pity before you unlock your phone, open the app store, and download Hinge.

————————————

Kendall hangs up and stares out the window of his chauffeured car’s backseat. He’s a few minutes away from the theatre where Willa is holding her play’s preview, and if he didn’t want to go before, he definitely doesn’t want to go now.

The disappointment he feels is frustrating. You aren’t dating, you aren’t fucking, he can’t even really say you’re friends because you don’t hang out with each other outside of work. He’s not really losing much by not being able to text you anymore, so why is this so disappointing? He chalks it up to you being the one to suggest taking a step back. His marriage to Rava aside, it’s very rare that he’s not the one to end things (not that this was even a relationship to begin with, he reminds himself again). He’s just frustrated because his assistant was the one to say that they shouldn’t text anymore, that’s it. He just needs to find a new person to focus on, someone who he can feel a bit more in control with.

The car pulls up to the theatre. He opens the door and steps out, ready to be Kendall Roy.

***

Willa’s play is shit of course, but one aspect of it manages to hold his attention. An actress - this pretty woman with short brown hair - catches his eye and keeps it for the entire show. He practically beelines his way to her at the after party and doesn’t hesitate to turn the cockiness and charm up to 1000%. She’s cute and bubbly, he’s definitely attracted to her, and she seems to be attracted to him (or his money, name, whatever), so he takes her home that night. The sex is really good, but for some reason the entire thing feels… off. Something about her isn’t clicking for him, but being alone isn’t really an option for him right now; he can’t just not have someone else to focus on after his call with you. He throws himself completely into this fling in hopes that eventually, he’ll start to like her more.

He does it all. He love-bombs her, he invites her to Dundee, he holes up with her in their lavish hotel room, he shows her off to his family, but none of it works. What is he missing? He’s back in the swing of things, getting his ego stroked and his dick wet, she’s hot, and he gets to play the role of the swaggering billionaire who exists in a perpetual state of unshakable confidence; it’s all the things he usually finds some semblance of pleasure in, but not this time - this feels so much more vacant than usual. It’s infuriating, why is this being taken from him as well?

He finds himself growing increasingly frustrated with her for not properly fulfilling her purpose of being an easy distraction, but he knows that his anger is misplaced. It’s not her that’s ruined this for him, it’s you.

Her interaction with his dad is the nail in the coffin. Having his father’s approval is the single most important thing to him, and with her on his arm, he can kiss whatever respect Logan may still have for him goodbye. Even if, like you, she had aced her conversation with his father, he doubts it would’ve mattered. He knows why it feels empty; he hasn’t actually earned her affections like he did yours, and he doesn’t really care to. Whether she knows the real him or not doesn’t matter, because this thing with her doesn’t fucking matter. She's not you. He sends her back home early and wonders how much more depressing his life can get.

————————————

Your Monday morning starts the same way it normally does. You get to work early and Jess is already there, ready to review the day ahead with you. Her behaviour this morning is a little more serious than you’ve seen before though.

“So there’s been some developments with the Brightstar incident…” she starts, and you can tell she’s already exhausted. “A whistleblower came forward, and he’s provided concrete details about what happened in cruises, and how it was all covered up. There’s going to be a federal hearing and Kendall will be testifying, so we…” she sighs. “We’re gonna have our work cut out for us this week.”

As you two get down to business, it becomes clear that it’s really just Jess who has her work cut out for her. She’ll be joining Kendall in Washington and working with him and the rest of the executive team to form a strategic plan for his testimony. Your week won’t be much different from the last two. You’ll be staying in New York, holding down the fort, and rescheduling every single one of Kendall’s obligations for the near future.

For you, this couldn’t have worked out any better. You’re only in your third week, so not having to learn anything new or dive into the dirty side of the corporate world is ideal when you’re still getting comfortable in the role. It also means that Kendall will be gone for at least a few days, which will make this transition of not speaking to him slightly easier. Out of sight, out of mind, right?

For Kendall, you’re concerned. Why exactly is he being called to testify? Because he’s the son of the CEO? Or because he played some part in this? Jess doesn’t give you many details about what this means for him, and you don’t press her for any. You’re not sure you want to know how involved he was with the cover up; you want to believe the best of Kendall, and if you learn that he was complicit in this kind of shit… the thought of it makes you feel sick.

Kendall and Jess leave for DC the next day, and you continue on with your week as scheduled. It’s weird being the only one there. You aren’t completely alone in the giant Waystar offices obviously, but without Jess and Kendall there, you’re pretty much just working by yourself and not answering to anyone. For this reason, you don’t hesitate to pull up the livestream for the congressional hearing on the day that Kendall is set to testify.

Tom Wambsgans is called first. You learned from Jess recently that he’s actually Kendall’s brother-in-law, and his assistant is Greg, the Roy cousin you met last week. Tom absolutely butchers his testimony in a way that gives you the worst possible second-hand embarrassment. ‘Good god,’ you think to yourself, ‘this company really is just a shitpile of nepotism.’

Kendall and Logan are next. Kendall sits next to his father with a stern look on his face. It’s the look that has completely replaced the crinkly smile you initially associated him with. You miss it.

Logan begins his testimony by attempting to gently brush aside the accusations, but when that doesn’t work, he doesn’t hesitate to throw Kendall under the bus. Your heart rate skyrockets as it becomes clear that Kendall is now the main target. Fuck, the last thing you want to do right now is watch what happened with Tom happen to Kendall. The senator questioning him seems ready to play hardball, and though you suspect that Kendall might be capable of striking back, watching him actually do it is hypnotic.

No stutters, no swearing, no filler words. He uses ‘sir’ and speaks respectfully while also turning every accusation back on the senator. The way he commands the room with his testimony is mesmerising, and as you watch him control the situation, you feel something change - a different type of attraction to Kendall is rooting itself inside you, and you don’t attempt to stop it.

Since the day you met him, you’ve thought he was handsome, smart, funny, sexy, all that good stuff, but right now… god, this is a side of him that you hadn’t fully seen yet and you need to see more. Despite fantasising about him for weeks now, this forcefully assertive side has you picturing him a different way. You can't stop yourself from imagining Kendall on top of you, telling you exactly what he wants, talking you through it while he brings you over the edge. He'd want to lay claim over you, he'd tell you that you’re his and only his.

You feel your heart rate pick up again.

His testimony ends and you close the browser. Fuck. You shouldn’t have watched this. It’s the furthest thing from ‘out of sight out of mind’ you could’ve done. Your brain is swimming with thoughts of Kendall. Kendall kissing you, Kendall touching you, Kendall fucking you. And now, you have to get ready for a date with someone else.

This week seemed like the perfect time to do it - waste no time and put yourself out there while Kendall isn’t around. You started matching with people on Hinge and eventually connected with someone you could see yourself having some fun with. He asked you out for drinks tonight, and you were originally planning on going home after work to change and get ready, but you don’t give a shit anymore. He’s not Kendall. It doesn’t matter.

You dump the contents of your bag out onto your desk. A tube of chapstick and some blotting powder are the only beauty products you have with you. Sighing, you dab at your face with the powder puff and apply the chapstick. You’ll quickly fix your hair in the bathroom before you leave, but unfortunately, that’s all the prep this Hinge guy is going to get from you today.

You hang around the office relatively late. Your date is at 8pm, so it isn’t until 7:30 that you finally stop spinning from side to side in your desk chair and leave the building. When you arrive at the bar and meet your date, you immediately feel guilty. He’s good looking, he’s well dressed, he seems excited to be on this date with you, and you couldn’t care less about him. You could be on a date with the man of your dreams right now and it wouldn’t matter because he’s not Kendall. “Hit us as hard as you can, we can take it. We have nothing to hide,” in Kendall’s deep, assertive voice replays in your head over and over, and no matter how hard you try, you can’t get excited about the man sitting in front of you.

You’re able to make it through 2 hours before you just can’t pretend to enjoy the date anymore. He offers to walk you home, but you don’t accept. He doesn’t pressure you, just tells you that he had a good time and he hopes you get home safe. You end the date with a hug before going your separate ways, and you know that you will never see that man again.

The journey home is a daze filled with negative self talk. Your mind is stuck on the only man in the city that you can’t have, and when a perfectly good alternative is presented to you, you can’t do anything except think about Kendall. God, you’re a fucking mess.

It gets worse when you finally return home. You begin digging through your bag for your apartment keys, ready to just crawl into bed and sleep this day away, but they’re nowhere to be seen. You check the pockets of your bag, your pants, your jacket, but they aren’t there. Your mind races, wondering where you could’ve left them when you remember dumping your bag out onto your desk.

“Are you fucking kidding me,” you swear under your breath. It’s almost midnight on a Friday night, there’s no way in hell that your geriatric landlord is going to be around to let you into your apartment. You have to go back to work.

You feel numb as your climb into the Uber you order and are shuttled back to work. Forgetting your keys further confirms for you what a mess you are. When you arrive at the office, you speak to the security guard in the lobby. After showing him your ID card and explaining your situation, and he lets you take the elevator up. You plan on getting out of there as quickly as possible, but that changes when you approach your desk and notice that a lamp in Kendall’s office is on.

And then, you notice Kendall.

He’s on the couch on the far side of his office, scrolling on his phone while he roughly rubs the back of his neck. Your task of retrieving your keys vanishes completely from your mind, and you approach his office door, knocking softly. His head snaps up at the sound, but his expression relaxes when he see’s it’s you.

“Hey,” you say gently as you push the glass door open. “You’re back already.”

He rises from the couch. “Uh, yeah… benefits of a private jet.” He gives a half-hearted smile and gestures for you to come in. “I uh, yeah, I didn’t want to stay in that, fuckin’, political hell hole any longer than I needed to.”

“Understandable,” you say as you close the glass door behind you. He’s standing near the window now, arms crossed, and you stand opposite him awkwardly. His eyes flash over to the couch.

“Sorry, I’m fuckin’ exhausted, can we sit please?”

Though all you want right now is to be in your own bed, the expensive couch in Kendall’s office is an acceptable placeholder, especially when staying here also means you get to be in his company. You nod and sit down, and he joins you, keeping a good amount of space between the two of you.

“So… how do you feel?” you ask after a moment, your head turning in his direction.

“Oh, um, yeah. Initially, I felt pretty good,” he says. His legs are spread apart and he’s leaning forward, forearms and elbows resting on his thighs as he clasps his hands together in the empty space. You notice his long fingers, the veins protruding across the back of his hands and defined tendons stretched across his skin. You never paid much attention to his hands before, but now, all you can think about is how much you want to hold them, want them on you, want his fingers in you. Fuck, you really shouldn’t have watched that livestream. “You know, everyone was telling me it went well, but, uh… someone still needs to go down for it. I just… I have this shitty fucking feeling that it’s gonna be me.”

There’s no trace of anxiety, or anger, or sadness in his tone. He sounds so removed from the situation, almost apathetic toward it. You’re desperate to find out if that’s for the reason you fear.

“Kendall, I have to ask,” you say slowly. “Did you… know? Anything about it?”

You don’t dare look at him after asking something like that, your eyes stay glued to your feet. He sighs, and you feel him sit up beside you. “I know it’s hard to believe but, no. I didn’t.” He pauses for a moment before he continues. “It’s… it’s kind of an unspoken rule that the nasty stuff shouldn’t reach my desk. The executives who report to me, they eat a lot of shit for me so that I don’t have to. Keeping upper level management out of it gives us plausible deniability… protects the company.”

You nod. It’s a relief that he wasn’t the one covering up the horrors that happened on those cruises, and you can now assume that his apathy toward the entire thing is a coping method - detaching himself from the feeling that he’s going to take the blame for everything is probably the only thing keeping him together.

He’s looking over at you now, and your concerned expression must be telling him a different story. “I know, just because I wasn’t fully aware of the details doesn’t make it okay. It’s fucking awful. But, I uh, I think I’ll be the one taking the fall for it anyways, so there’s my fucking karma.” He sighs again.

You shake your head slightly. That’s not at all the impression the hearing left you with. “I don’t know Kendall… I was watching and you… you did really well,” you offer. “I know I’m not a corporate strategist or anything, but from the perspective of an average citizen, you um…” you pause, wondering how to properly word this. “You seemed powerful.”

Kendall gives a small, slightly bitter laugh as he leans forward on the couch again. He hangs his head down and begins to roughly run his hands up and down his face. “Yeah, that’s uh, probably not the best impression to make when they want a top executive’s head on a fucking stick.”

You instinctively turn your body toward him and reach your hand out. It lands on his shoulder and you feel him freeze under your touch, but he doesn’t move away. “No, but not powerful in the sense that people will want to overthrow you, powerful in a way that seemed… warranted. Like… you controlled your responses so masterfully, no one could watch how you handled that situation and think that your power was just given to you by default or achieved through brutality.”

There’s no need to expand on this point - he knows you’re referring to Tom and his dad, and you wouldn’t dare to make any explicitly negative comments about either of them. You can see that the Roy family has a fucked up dynamic, but they also seem close. You need to focus not on what they did wrong, but on what he did right. “You presented yourself as someone who deserves their position, and Americans love it when people earn their privilege. I really can’t see you being a main target. You just… yeah, you came across really well,” you finish.

You suddenly realize that as you’ve been speaking, your hand has migrated from his shoulder to his upper back, and you’ve started to rub small circles against the smooth fabric of his button up shirt. He sighs, his head still hanging low, and you feel his muscles relaxing slightly.

“Thanks,” he mumbles softly, and you aren’t sure if it’s in response to your complimentary words or your soothing touch, but it doesn’t really matter as long as you’re helping him feel a little better. You continue rubbing his back gently for a bit until he slowly sits up straight again. You take this as his way of saying you can stop, so your hand retreats to your lap. You immediately wish you had another reason to keep touching him.

He takes a deep breath. “It, uh…” he stammers before pausing for a second, like he’s figuring out how to properly word what he wants to say. He leans back against the couch. “It would have been nice to have had you there,” he says, eyes glazed over and directed at the floor. “Jess was great, of course, you just, you have a comforting presence…” He hesitates before he looks over at you.

You hold his eye contact for a moment before your gaze drops to your lap. This conversation is heading in a risky direction - you should shut it down, say goodnight, and go home, but you can’t stop yourself from leaning into it further. The two of you can never be seen together outside of work, and right now, in his office with everyone else gone, is probably the only opportunity you’ll get to have another meaningful in-person conversation with Kendall. So, instead of being smart and leaving, you stay and say what you’re actually thinking.

“I uh, I’m actually kind of relieved that I wasn’t there,” you say lightly, fiddling with your fingers in your lap.

In your periphery, you see Kendall nod. “I get that… it wasn’t the most enjoyable environment to be in.”

“No, it’s not that…” you waver. Fuck, are you really gonna say this? There’s no coming back if you do, but maybe that’s what you actually want. The tension between the two of you has been built up too much and it needs to break. “Just… watching you… you know, do your thing, it um,” you laugh awkwardly, and Kendall sits up beside you as he waits for you complete your thought. You keep your eyes in your lap. “… I’m not sure I would’ve been able to play it cool around you after that.”

You keep your eyes down, but you can feel Kendall move closer to you, and when he speaks, you can hear a smile in his voice. “Oh yeah?” he says smugly. “You wanna elaborate?”

You roll your eyes, still keeping them off his face. “Oh my god, I already said you were powerful,” you groan jokingly. “What else do you want from me Ken?”

You’ve never shortened his name before. Jess always calls him Kendall, so using his more informal name would be suspicious. It slips out now though, but you don’t regret it. It just happened naturally, and you’re ashamed to admit it, but you love how it sounds coming out of your mouth. It feels a bit like how you would talk to him if he was your boyfriend. It’s nice to get to live in that world for a second.

“I want a whole fuckin’ sentence,” he laughs, and he moves even closer to you. Your legs are barely an inch apart, you can practically feel the heat radiating off him. You finally look up at him.

“It was hot, okay? You were hot, is that what you want to hear?”

His lips are on yours before you can react, but you don’t need to. Your response is immediate, as if you knew it was coming, and you fall into him like it’s second nature.

Kendall’s hands grip your face, his fingers knotting themselves into your hair. Your arms race to wrap around his neck, and you pull each other in. This is only the second time you’ve kissed, but it feels strangely easy, like it’s something the two of you have been doing the entire time you’ve known each other.

His mouth moves furiously against yours, his tongue slipping past your lips, and you feel excitement begin to build in your core. You could attempt to lie to yourself and pretend that you didn’t ache for him when you were in an office surrounded by other people, but it’s impossible to do that now with with his hands exploring every inch of your body.

Your arms loosen themselves from his around his neck and your hands slide their way down to the neckline of his dress shirt. It’s unbuttoned low enough for you to access the skin of his shoulders and upper back, and you sneak your hands underneath the fabric, desperate to feel his warmth. Your urgency to get under his clothing has him groaning against your mouth, and he pulls you onto his lap, his hands not hesitating in gripping your ass as he does. You straddle him, your core resting on his groin, and you can feel him hardening by the second.

Your hands travel down his chest to the buttons of his shirt, which you begin to undo frantically, and you feel Kendall continue to grow beneath you. God, knowing that you might get to feel him inside you again… it sends a rush of heat coursing through your body that settles snuggly in your lower stomach.

His hands still on your ass, he begins to guide your hips forward and back over his own, pulling your body down onto his so you can grind as much pressure against him as possible. The way your centre hits his just right is heaven. You break apart from his lips to moan into his neck, your hands still working away at the tiny buttons lining his shirt, his hands still guiding your hips.

“Fuck,” he husks into your ear, “god, fuck I need you,” and he begins to move your hips faster. Your fingers undo the last button of his shirt and you spread it open, pushing it off his shoulders and revealing his chest. You’re both feeling that same sense of urgency now, and Kendall’s hands leave your hips to travel to the hem of your shirt.

RING RING RING

The phone in his pocket sounds off, startling you out of your embrace.

“Jesus fuck, sorry,” he apologises as he pulls it out, and it looks like he’s about to silence the ringer when you both see the name on the screen - ‘Dad.’

He looks up at you. “Yeah, fuck, I should take this,” he says, and you immediately climb off him, returning to your spot on the other side of the couch. Kendall stands up, his shirt still open, and answers the phone.

“Yeah, Dad,” he says, and you can hear Logan’s gruff tone on the other side of the call. Kendall listens for a bit, his back to you, just nodding. “Yeah, okay, I’ll uh, I’ll make my way there. Okay. Yeah, see you soon.” He hangs up and hesitates before turning back to you.

“… Everything alright?” you ask. His eyes are fixated on his phone screen and he’s typing furiously.

“Um…” he says as he finishes writing his message. You hear the 'whoosh' of a text being sent before he locks his phone, stuffing it into his pants pocket. He then begins to button his shirt back up, and disappointment washes over you. “I… yeah, I don’t know. He’s organising a vacation for everyone… like my entire family, all the higher ups… pretty much anyone who could possibly take the fall for the Brightstar mess.” He shakes his head as he does up the last button. “Doubt it’s gonna be a fucking team building session or whatever.”

He finally looks over at you, pausing for a moment as his gaze turns a little softer. “It, um, it was probably good that we got interrupted before we did something stupid, right?”

Oh.

You look down and nod. As much as your entire body wants to pick up where you left off, he’s right. What were you gonna do, be the assistant who fucks their boss on company property? What a fucking cliche. Add in the embarrassment of Kendall being the one to call it off, and you can now feel anxiety starting to build in your chest. What began as something you desperately wanted is quickly shifting into the most shameful moment of your life. You have to get the fuck out of here.

You stand. “I should go,” you say. “Um… I hope the trip goes well, and I’ll, I’ll see you after.” You don’t wait for a response from him, you leave his office and quickly grab your keys from your desk. You don’t look back.

The elevator doors slide open immediately for you, and you rush to enter, scrambling to press the button for the ground floor. You lean up against the wall as it starts its descent, exhaling a shaky sigh.

Fuck.

What now?

Chapter Text

Kendall watches you rush out of his office. You grab something from the surface of your desk, turn the corner toward reception, and then you’re gone. He’s left standing with his hands on his hips in the centre of the room, completely alone. For a moment, his eyes refuse to the leave the place where he got his last glimpse of you. Shit… what a fucking mess he’s made of this situation.

He wanders over to his own desk and collapses onto the chair. The office should be painfully silent, but Kendall’s ears are ringing. He can feel his heart pumping and hear the intense beating of it as the blood rushes through his body and to his head. It’s all setting in now, how quickly he fucked up the possibility of the two of you ever being friends again, or hell, even having a normal working relationship. Coming back from what just happened… impossible. He can’t take back kissing you and he can’t take back calling it a mistake, so now he’s the asshole who made a move on you and then rejected you a minute later. Why did he even call it off? His desperate need to touch you again was all he had thought of for weeks, but when he gets the opportunity to, he suddenly has self control? Jesus Christ, what a fucking self-destructive prick he is. If he comes back from this trip to find that you’ve quit, he won’t be surprised. Depressed and angry, yes, but surprised? No.

Resting his elbows on the wooden surface, he slowly leans forward to cover his face with his hands. His vision goes dark, but it doesn’t stop the incessant pounding in his ears. ‘Fuck - up - fuck - up - fuck - up’ it seems to be saying, and he doesn’t disagree.

————————————

You don’t order your Uber from outside the Waystar building; instead, you begin walking as fast as you can in whatever random direction your body takes you. You’re 3 blocks away before you allow yourself to finally slow down and breathe, but unlike your body, your mind is still operating at full speed. You’re over exhausted, you’re emotionally drained, and you’re anxious as hell, which makes for a dangerous combination. Should you quit? Move away? Drop off the face of the earth completely?

‘Just get home,’ you tell yourself, ‘you can plan your escape after getting some sleep.’ You allow yourself to finally get an Uber, and after what seems like the longest car ride of your life, you enter your apartment. Closing the door behind you, you stand in the entryway and look around your space. It’s so small, just enough room for your bed, kitchen, and sitting area, but it’s yours. After a month, it’s finally started to feel like home. The space has been decorated in a way that feels representative of you, you’ve learned the trick to getting the perfect heating temperature from your ancient radiator, and you’ve even started to find comfort in the gentle footsteps of the person living above you. You can’t leave, not when you’ve just started to build something resembling the independent life you so badly wanted.

You flop down on your couch and throw your arm over your eyes, allowing yourself to take a few deep breaths. Kendall will be out of town for awhile, so you shouldn’t make any impulsive decisions before you’ve even determined exactly how bad working with him will be following tonight’s fiasco. You can just feel it out first, and if it’s unbearable, you can probably use your position at Waystar to leverage another job somewhere else. Okay. No quitting, no moving away, no disappearing. You’re not going to let Kendall’s erratic behaviour stop you from living the life you’ve wanted for so long. Let him sit in the mess he made. But you’re done with him for good now - really.

————————————

The Waystar vacation is exactly what Kendall knew it would be. Not a relaxing yacht trip in the Mediterranean, but a cesspool of tension, stress, and arguments about who is most at fault. Though the blame is passed around and multiple scapegoats are suggested, Kendall knows that his Dad has the final say. After a few days of uncertainty, Logan takes Kendall aside and appoints him as the sacrifice.

He knew it. He knew it would be him.

He understands why; his dad is right when he says that the optics make sense. Kendall was one of the central figures targeted by congress in the hearings, he was the executive that those responsible for the coverup reported to, and, being a member of the Roy family, his demise would be the exact kind of justice that the public wants. But all that aside, Kendall knows that this is karma coming back around for him.

“Maybe I deserve it,” he says to Logan, who immediately opposes, but Kendall can’t accept the dismissal. His dad may not think about it often, but that server kid never leaves Kendall’s mind for even a second. “Yeah, for everything… The boy...”

“No, no,” Logan dismisses again. “NRPI, don’t beat yourself up. ‘No real person involved.’ You know, it’s… it’s nothing.” He rises from his chair and it’s clear that he’s done with the conversation.

Kendall stares at Logan. He doesn’t want to believe that he heard his father correctly… but he did. No real person involved. His father doesn’t see what Kendall did as anything significant. Not a real loss. ‘It’s nothing.’

It’s evil.

He feels his foggy mind begin to clear. He’s done bad things, terrible things in his life, but he feels remorse. He feels guilt. He feels empathy toward others. His father? Kendall suddenly realises that he can’t recall a single instance of Logan exhibiting any of those feelings. Why is he protecting this man? What has his Dad done to deserve immunity? Why, of all people, should he not have to face the consequences of his actions?

Kendall has nothing left to lose. His life is at rock bottom, there’s nowhere to go but up. Logan, on the other hand, could fall much, much farther. Maybe it’s time to restore some balance to their dynamic.

Kendall nods. “Right,” he says flatly, pretending to accept the way his father shrugs off the conversation. He approaches Logan and places a kiss on the side of his cheek. It’s a final goodbye to this version of his life; living under the authority of his father, being a passive spectator to his own life, having no control. He’s done with it, he’s not going to sit around feeling sorry for himself anymore. If everything is going to shit anyway, he may as well do what he wants, and that includes going after the main thing he’s been depriving himself of.

After Logan’s decision is announced to the group, Karolina arranges for a press conference to be held the following day. The proposed plan is that Kendall will fly back to New York in the morning, and upon landing, will be escorted directly to the venue where he’ll announce his culpability in the Brightstar coverup. Kendall insists that he needs to leave immediately though; he has some other business to take care of. What that business is, he doesn’t say, but when his driver picks him up on the tarmac back in New York, he doesn’t hesitate to give your address as his destination.

It’s late, almost midnight. He doesn’t know if you’ll even be awake still, and he’s sorry if he has to wake you up, but this can’t wait until tomorrow - it needs to be settled tonight. He won’t be able to concentrate until it is.

His driver pulls up to your building and lets him off at the curb. He steps outside, an overwhelming sense of deja vu washing over him. The last time he was here, he was convinced that he would never be back or even see you again. How much has changed since then.

Kendall walks up to your building’s front door and takes a deep breath. The next 24 hours are going to alter his life in so many ways, and this right here is the first step. If he can successfully complete this, the next few steps are going to be so much easier. He presses the buzzer to your apartment.

————————————

You’re in your bathroom getting ready for bed. You’ve just finished brushing your teeth when your buzzer goes off and your heart stops. It’s not uncommon for these old brownstone buildings to still have their ancient intercom systems in place, and the buzzer into your apartment is obnoxiously loud. The sound doesn’t usually surprise you this much, but you also usually aren’t receiving unexpected visitors, especially not this late.

You lightly pad over to your front door, checking that it’s double locked first before you press the intercom. “Hello?” you ask.

It’s silent for a moment, and you think someone must’ve pressed the button for your apartment by accident, but then a response comes through.

“Hey…”

You know it’s him immediately. The deep baritone of his voice has latched itself into your brain. It’s a sound that sends your heart into frantic mess every time you hear it.

“It’s Kendall,” he continues, and you almost laugh. There’s no way you could ever assume that the deep voice calling up to your apartment at midnight was anyone else.

“… Can I come up?”

The background hum of the intercom stops buzzing, indicating that he’s taken his finger off the call button. You stand there for a second. Of course you’re going to let him up, but how should you play this? Why is he even here? Your last interaction with him was so embarrassing, and you can’t repeat that rejection again. You’re not going to make any assumptions about him wanting you the way you want him this time around.

You press the intercom button. “Uh, yeah. Apartment 201,” you remind him before buzzing him inside.

————————————

Kendall lets out a deep breath. Okay - progress. He was pretty sure that you wouldn’t turn him away, but it’s still a good sign that you’re open to talking to him privately after what happened in his office last week. He enters the building and the climbs the stairs to the second floor, his heart beating faster with every step he takes until he’s finally outside your door. He hesitates a moment, rehearsing what he needs to say to you before he knocks.

————————————

You haven’t moved from your spot beside your front door since you buzzed him in. You don’t bother to run to the bathroom to fix your hair, or to your dresser to change into something more presentable. Adjusting your appearance for him just in case he’s here for the reason you hope he is won’t help you go into this conversation with no assumptions. You just stand frozen in your tattered sweater and shorts for what feels like a century instead, waiting for him to knock. When he finally does, you count to 5 before opening it. You can’t let him know that you’ve been waiting at the door for him like a dog.

Your heart lurches at the sight of him; you’ve never seen him in casual clothing before. Even on the night you met, Kendall was board-meeting-ready in an expensive suit. Now though, he’s wearing dark jeans, a soft looking sweater that you have no doubt costs more than your monthly rent, and has allowed his stubble to grow in a bit. He looks so good that it hurts, and knowing that he’s not yours makes it worse. You have to remind yourself of the embarrassment you felt from his rejection last week to suppress the urge to throw yourself at him right then and there.

————————————

Kendall takes in the sight of you in your comfy clothing. He’s gotten so used to seeing you in the office that he almost forgot this side of you existed - this sweet, cozy side. The way you look right now, like you’re ready to curl up under the plush covers of your duvet, makes him feel safe. It reminds him of the one night he spent here with you and how, despite his early wake-up call, it had been one of the best sleeps he’d had in as long as he could remember. Your skin against his, the way you nuzzled yourself into his chest, feeling your body softly rise and fall with your breathing, it soothed him in a way that he didn’t think was possible. That’s all he wants right now; not to talk, but to grab your hand, lead you to your bed in the corner of the room, and hold you close until he falls asleep. He knows he needs to explain himself first though, and can only hope that this conversation will lead to him getting more nights like that.

“Hi,” he finally says. Your face doesn’t give anything away, he has no idea how you feel about him being here. He clears his throat. “Can I, uh… come in?”

He watches your eyes drop to the floor before you nod and step aside to let him in. ‘Uh, yeah, come in,” you say, but again, your voice doesn’t offer any insight to your thoughts about his midnight visit.

“Thanks,” he says as he steps inside and looks around your place. Most of it is the same as it was last time he was here, but you’ve made some decorative additions that he doesn’t remember from before. The room feels fuller, warmer, more you. He eyes the large framed print hanging over your couch. “That’s nice,” he comments, trying to loosen the tension.

“Um, thanks,” you say, eyes flashing over to the print before falling back on him. “Kendall… why are you here?”

Okay, straight to business then.

Your tone isn’t mean, or annoyed, or even curious, which is bizarre to him. You just sound tired, and whether that’s because of the late hour or the messy situation with him, he doesn’t know, but he does know that he doesn’t want to waste your time any more than he already has.

He sighs. “I… uh, I need to talk to you about something.” Fuck, how should he even start this? He clears his throat. This is just like making a pitch. He’s pitched a billion ideas before, this is no different. “Do you have a minute to, uh, hear me out?”

You pause for a moment before nodding and walking over to your couch. You sit down and wordlessly gesture for him to do the same. He does, leaving a good deal of space between the two of you as you pull your feet up and sit cross legged on the couch, grabbing a pillow to hug to your chest. You face him, but your guard is clearly up.

Kendall takes a deep breath, his hands flexing open and closed as he chooses his words. “So, I uh, I know we agreed that working together wouldn’t… that it wouldn’t be an issue, that we could, you know, keep things professional.” He pauses. How the fuck is he supposed to ease you into this idea? “I can’t, uh… I can’t fuckin’ do that anymore.” That last bit comes out a bit more seriously than he intended, but he can’t help it. It’s not easy to act lighthearted about how much wanting you has been destroying him.

————————————

You stare at Kendall intently. This all feels very familiar to the conversation you had with him in the copier room on your first day, the conversation when he told you to quit because your presence would be ‘too distracting’ for him. Now it seems like he’s hinting that you should quit for his sake instead of instructing you to.

You sigh. It’s not like you don’t understand. You can see that your presence at work distracts him just as much as his presence distracts you. His work is much more demanding than yours is though, and having you around clearly doesn’t make it any easier. But still, you need a job, and leaving Waystar after only a month definitely won’t look good on your resume.

“I can’t quit, you know that,” you begin, doing your best to not sound combative. “If you can just transfer me to a different department or something, I think it—“

————————————

He knits his eyebrows together and shakes his head. What? How did you manage to get the exact opposite idea of what he’s trying to say? “No, no, I’m not asking you to quit, just…” he hangs his head and closes his eyes. Easing you into this is much more difficult than he thought it would be. “I, I need you to understand that… that something has changed for me.”

Your eyebrows knit together as well, and it’s clear that he’s confused you even more. God, why is he so fuckin’ bad at this? “Okay…” you say hesitantly. “Well, what’s changed?”

Kendall looks at you straight on and takes a breath. He knows that he has to be completely open if he’s going to get what he wants, he can’t sneak his way into a relationship with you. Being with you will require vulnerability, he has to get used to that.

“…. I…” he starts, the words caught in his mouth, but he’s committed to getting them out. “I want something more with you.”

————————————

You can’t help it - your heart soars. After weeks of yearning for Kendall, hearing that he wants you… the feeling is indescribable. You can’t get your hopes up yet though, he needs to say more first.

“What do you mean?” you ask sincerely. “What are you asking for?”

He takes another moment to collect his thoughts, carefully choosing his words. “Can we explore a… personal relationship… outside of work?”

This is what you’ve been waiting to hear, but the way he says the words so slowly, so cautiously, makes you nervous. It’s like he doesn’t want you to get the wrong idea… If he wants to date you, wouldn’t he just say that?

You play dumb. Make him spell it out for you.

“Personal relationship,” you repeat. “We already tried to be friends outside of work…”

“I know, I know,” he interjects. You can tell he’s getting frustrated now, but you don’t feel guilty. He’s the one who came here to talk and he needs to be the one doing the talking. “I meant if, if you’d be willing to explore something more… intimate.” He looks over at you now. “It’d have to be, you know, private though, obviously,” he adds quickly.

Your heart sinks. The picture is becoming clearer now and it seems like he just wants to be secret friends-with-benefits. A situation where he gets to fuck you but doesn’t have to commit, doesn’t have to act like your boyfriend, doesn’t have to be faithful to you. You’ll just be the hidden hook up he can call when he needs to.

“Ken…” you say sadly, slowly. “I… I don’t want to be my boss’ side piece.”

————————————

Your words hit him right in the chest. He knows he hasn’t been as open during this conversation as he should’ve been, but how could you think that that’s all he could want from you? He can get sex whenever he wants, you’re so much more than that.

He looks at you, feeling ashamed that he hasn’t made himself clear in the way you deserve.

“Side piece?” he questions, shaking his head. “No, you— you can’t think that’s how I— that I’m just looking for someone to hook up with…?”

Your gaze has been directed down toward your lap, but you look up at him now. “… Maybe? I don’t know,” you say uncertainly, and his heart breaks a little more. He’s fucked this up so much worse than he thought was possible.

He shakes his head again. “That’s not, that’s not…” He’s struggling - how is he supposed to fix this?! “I really…” He doesn’t know how to be vulnerable with you yet.

He sighs and gathers himself. “Can I, uh, can I come closer?”

You nod, and he moves himself over to you, relieved to see you inch in his direction as well. You look so vulnerable right now - holding one of your couch pillows to your chest, curled in on yourself, an uncertain expression on your face. It makes him want to protect you, but he knows that what he needs to protect you from is his inability to be emotionally available. What you need right now, what he owes you, is real vulnerability.

He turns fully toward you, facing you and this miscommunication head on. “You are… so much more than that. I want, I want us to be together. I…” he sighs again. “It, you know, with everything going on, it does need to be just between us for the time-being, but…” he reaches for your hand now, he can’t help it. “I’m asking for something real, don’t- please don’t mistake us keeping it private for me not taking it seriously. I’m serious about this, about you.”

He’s on a roll now, and is almost tempted to say more. He wants to tell you how much you’ve affected him since you met each other, that you’ve made him reconsider his belief that he was better off alone, or that, without his status, he would be unlovable. Now isn’t the time though. Hopefully, there’ll be opportunities in the future to get into all of that, so for now, he just awaits your response.

————————————

You and Kendall hold each others gaze for a moment. His brown eyes are warm, sincere, and sad. You can see that he means what he says, and that it’s really important that you understand what he’s telling you. He actually wants you the way you want him. You look down at his hand holding yours and you’re torn between wanting to break into a smile from the pure joy you’re feeling, and crying from the tenderness of the moment, from the relief of hearing him say the words you’ve been so desperate to hear. You look back up at him and his eyes are still on you, waiting.

You just need to know that he means this though, that this isn’t just a late-night slip of self-control, something he’ll regret in the morning and have to take back. You’re positive that there would be no coming back from that.

“Are you… absolutely sure?” you ask hesitantly. “You have a lot going on right now, and I… I don’t think I can handle you changing your mind on me again.”

You give him a soft smile to let him know that you don’t mean this to come across bitterly, that you really are just trying to protect yourself, but that he needs to mean it. Really mean it.

He looks down at your hand in his, and you feel his thumb brush across your skin. “I’ve…” he starts. “I’ve gone back and forth about a lot of things lately… I feel a bit like, uh… like I’ve been floating, just fuckin’ untethered in the world. The only thing that’s made me feel… rooted, the only thing I haven’t doubted that I’ve actually wanted, is, uh, is this.”

A feeling of warmth rushes through your body. He’s said everything he needed to. It’s real, it’s happening. You get to have him.

You move closer to Kendall. You’re directly beside him now, still facing him with your legs crossed on the couch and his hand holding yours. You give it a light squeeze as you wait for his eyes to meet yours. He looks down at your hands before his lifts his gaze to yours. You nod gently as you utter a simple “Okay.”

Kendall looks at you, dazed for a moment. His thumb begins to gently stroke your hand as he takes in your single word. “Okay… so you… so you’re on board?” he clarifies.

You smile a little bigger. Leave it to Kendall to make something so romantic sound corporate. “Yes, I’m on board,” you laugh softly. “Very on board.”

————————————

Kendall returns your smile, relief washing over him. It feels like he’s been holding his breath since he walked into your apartment, and now he can finally breathe deeply. The full weight of the stress he’s been carrying for months seems to come pouring out of him as he exhales.

He looks at you now, his hand reaching to cup the side of your face, and realizes that there’s no reason to feel guilty with you anymore. He isn’t hiding his identity, he doesn’t need to resist you for the sake of a professional relationship, he doesn’t have to rush to have you because he’s caught up in a moment of weakness. He gets to enjoy you, savour you, be with you the way he wants to. He gets to take his time.

Kendall feels euphoric as he guides your face toward his. He meets you in the middle to kiss you, not hesitantly, or frantically. His kiss is gentle, tender, and affectionate, and he’s not sure what he was expecting, but he feels a weightless relief rush through him when you return the kiss enthusiastically.

Though his soul feels light, his body feels heavy. It’s like a magnetic force is pulling you toward each other, but neither of you seems to be making any effort to resist it as he feels your arms wrap around him just as his wrap around you.

He holds you close, trying to memorise every good feeling he’s experiencing in this moment. He isn’t confused or afraid of what he feels for you anymore; he can see now, as he gives up control and let’s his body respond to its connection with you, that this is what he’s been waiting for. He hasn’t been deprived of sexual intimacy in his life, but sexual intimacy with a true emotional element… he’d forgotten what that felt like. Not just two bodies wanting to experience pleasure, but two people wanting to express how they feel about each other. He pulls you in closer.

————————————

You can feel Kendall’s heartbeat in his chest as he holds you tightly against him. His hands grasp at your back as his tender kiss becomes a little deeper, and the butterflies in your stomach begin to stir as the affectionate tone to your make-out turns a little hungrier. You don’t realize it until he’s on top of you, but he begins to guide you backward on the couch until you’re lying down, his weight pressed on top of you as you melt into each other.

Kendall’s mouth detaches from yours and migrates to your neck where he begins to kiss and suck, causing your already heavy breathing to come out in a gasp. Your hands sneak their way under his sweater (which is just as soft as you expected it to be) and clutch at his warm skin, desperate to feel him against you. You hear a low “fuck” against your neck as Kendall feels you under his clothing, and he begins to grind his hips against yours, adopting a deep, slow rhythm.

The feeling of him on top of you, his length hardening against your centre, his mouth leaving long kisses wherever your skin is visible is intoxicating. “Kendall…” you breathe. You want to move to the bed where you’ll have more room to explore each other, but bringing yourself to stop him for even a second is going to be difficult.

“Yeah, baby?” he husks in your ear as he continues to rub his groin against yours, his lips brushing softly against your jawline as he speaks.

The pet name sends your stomach into somersaults and a rush of warmth to your core. You can’t stop yourself from removing your hands from underneath his sweater to bring them to his face, guiding his mouth back to yours. The kiss you initiate, deep and passionate, has his cock fighting against his jeans even more. You can practically feel it begging to touched by you. “Can we…” you breathe as you pull away momentarily, “um, go over to…”

You’re not sure why you feel so nervous asking to continue what’s already started, so you just nod your head in the direction of your bed. Kendall takes a second to take in your suggestion before he’s pushing himself off the couch.

“Oh, yeah, fuck, yeah let’s go,” he says, and he gives you his hand to help you up. The moment you’re standing again, he pulls you back into him, pressing his lips firmly against yours as he moves his hands up from your hips, and under your sweater where they land on your bare waist. He grips you there for a moment before you feel him begin to lift the hem of your shirt over your head, tossing it to the side and reaching back over his shoulders to pull his own sweater off. It lands next to yours, and the difference between the two articles of clothing side by side makes you want to laugh. Your worn-in cotton laying next to Kendall’s pristine cashmere perfectly captures the vastly different worlds you come from, and it suddenly hits you that you’re dating someone with an amount of money and power that you can’t even conceptualise. You don’t let yourself dwell on it now though; he’s here with you because he wants you. He’s made it clear now that he only wants you, and watching him pull his pants over his hips and off his legs, revealing the bulge fighting to be set free from his boxers, drags your attention back to the present.

You rush to push your shorts off as well, leaving you both in just your underwear as Kendall pulls you in again and presses his mouth to yours, his hands racing to grab your ass as your arms wrap around him. You smile against his lips as he squeezes, prompting an even bigger smile from him. As you pull back to look at him, you’re met with his crinkly eyed smile, the one you’ve been missing for weeks. You feel like you’re about to burst with joy.

“I really fuckin’ like you,” Kendall says as he smiles against your cheek, leaving a trail of kisses down to your jawline.

You breathe out a laugh. “Oh do you?” you tease softly, and you feel the hum of a low “mhmm” against your neck. The vibration as his deep voice rumbles against your skin sends a shiver down your body.

“I like you a lot too,” you sigh, your hands exploring the warmth of Kendall’s back as you bask in the pleasure of his lips hungrily working their way down your neck.

“Yeah?” he muses against your skin. His hands squeeze where they’re gripping your hips, digging his fingers into the plush of your skin. It’s hurts in the best possible way. “You like me a lot, huh?”

You smile as your hands run through Kendall’s hair, his lips still grazing over your neck. You know exactly where this questioning is leading, and you’re more than happy to play along. Excitement continues to build in your stomach, heat rushing through your body as you feel his hands glide up and down your back before returning to your hips to pulls them into his. You feel his clothed hardness pressed into your stomach, a glaring reminder of how much he wants you.

“So much,” you breathe in response, and you grab his hand to lead him over to your bed. “You want me to show you?”

Pulling Kendall onto the mattress with you, you quickly position yourself at his hips and allow yourself to graze over his bulge as you reach for the waistband of his boxers. Kendall’s hands race to touch you, desperate to stroke your head, your cheek, your arms, anything to feel you without getting in the way of what you’re about to do. You can feel him tense up in anticipation as you take your time pulling his underwear off his hips. The sight of his length springing free sends a rush of heat into your stomach. You feel a pool of wet between your thighs gathering quickly, and you squeeze your legs together in an attempt to ease the unbearable ache that’s building there.

Locking eyes with Kendall, you lightly grip his erection and lick a slow line up the side. Kendall watches you until he can’t keep his cool anymore, and his head falls back with a low groan.

“Jesus fuck,” he moans, and you feel his grasp on your arm tighten as you take him fully into your mouth. You move your head up and down on his hardness, bringing him to the back of your throat over and over again. His hold on your arm migrates to your hair, and he brushes it back so he can fully watch you. “Such a good fucking girl,” he husks, the hazy pleasure he’s experiencing seeming to deepen his already baritone voice. His praise sends a swarm butterflies flitting around your stomach.

You begin to move the hand that’s been encircling the base of his length up and down with your mouth as you adopt a steady rhythm, and the low moans and curses you hear from Kendall start to get a little louder and more frequent as he unconsciously ruts himself further into your mouth.

“Hang on, fuck— wait,” he says suddenly as you feel him guide you off his length. He sits up and, in an instant, has you on your back on the bed before swiftly pulling your underwear off your hips and then gently spreading your legs apart. His body looms over you as you feel one of his fingers slip past the outer lips of your core and spread the wetness that’s collected there up to your clit. He emits a low groan as he begins to circle your bundle of nerves, eliciting squirms and gasps from you as his touch sends shockwaves of pleasure through your body. “I fuckin’ can’t get enough of you,” he muses deeply as he leans his head down, and you suddenly feel the warm wet of his mouth latch onto your centre.

“Oh my fucking god!” Your words come out in a rushed breath as Kendall’s tongue begins to lap at you feverishly, his arms wrapping around your upper thighs as he pulls your core closer to his face. Your fingers race to his head, struggling to grip at his short hair, your hips bucking unintentionally in response to the way his mouth is practically worshipping your clit. “Kendall, oh my god, fuck,” you moan, unable to stop yourself from vocalizaing the flood of pleasure rushing through you.

Kendall lifts his head to look at you as he slides one of his fingers between your crease and begins to pump it in and out. “Fuck, keep saying my name,” he groans as he slides a second finger inside, and you feel your lower stomach clench as your arousal skyrockets. He leans back down and licks your core again, his fingers continuing their movement. “Fucking love how it sounds in your voice.” You feel him continue to passionately mouth your clit, and with the addition of his fingers inside you, you rapidly approach your climax.

“Kendall,” you moan, your squirming beginning to increase, “god, fuck, I’m so close.”

Kendall shows no sign of hearing you; he maintains the pressure of his tongue and the speed of his fingers, only momentarily bending them up inside you as he hits your g-spot, and quickly sending you toppling over the edge.

You grip Kendall’s head to your centre as a tsunami of warmth washes over you, the pleasure of it all causing your vision to go blurry. You can feel yourself pulsating around Kendall’s fingers as you call out his name again, your hands running through his hair as you grasp for anything to hold while you ride out the wave.

Your breathing is heavy as you feel him remove his fingers from your slit. He leans over to kiss you, and you can taste yourself on his mouth. “I’ve been thinking about doing that for too fucking long,” he smiles, his voice gravelly with satisfaction.

“You can do that whenever you want,” you laugh breathily. You pull him down to kiss you again before quickly sitting up. It’s his turn.

You push Kendall backward until he’s lying down, his expression slightly taken aback as you position yourself on top of him so swiftly. You don’t hesitate to line him up at your entrance the moment that you’re centred over his lap. “I still want to feel you though,” you say as you sink down onto him and feel his hands clench your hips.

“Fuckkk,” he groans, and you begin to move back and forth across his groin, his fingers digging into you as he attempts to adjust to the feeling of you around him. You can tell he’s losing the battle though - his pupils are blown out with lust as he watches you ride him, his eyebrows knitted together, and the stream of moaned curse words leaving his mouth is almost constant. You adopt a faster pace, finding a different kind of pleasure in the clear power you currently have over him.

“Sweetheart, fuck,” he groans, “I’m gonna cum if you don’t slow down.” He doesn’t seem to want you to stop though, as at the same time he says this, his hands reach up to feel your breasts.

“That’s what I want,” you breathe, your palms digging into his chest as your hips continue to grind against his. “Cum for me Ken, I want you to cum inside me.”

Your words are all it takes. Kendall takes you by surprise when he suddenly sits up, wraps his arms around you, and holds you tightly against his chest. A loud moan sounds through your apartment as he keeps you there, and you feel his cock twitching inside you as he finishes.

Kendall doesn’t release you from his hold as he comes down from his climax. He tucks his head into your neck as his heavy breathing softens, and you feel his length slowly do the same as it’s nestled inside you.

“Jesus,” he exhales, finally lifting his face to leave a kiss on your jawline. “You’re a little demon, you know that?”

“That’s a compliment, right?” you laugh softly. You begin to pepper little kisses around his cheek, revelling in the knowledge that this is something you’ll get to do with him again, before you climb off his lap. Kendalls flops backward on your mattress as you head to the bathroom to wipe his cum from your inner thighs, quickly rushing back to the bed so you can continue to feel him against your skin.

“I’m so happy we got to do that again,” you smile as you snuggle back into his open arms.

He breathes out a sigh of contentment as you settle back in with him. “Me too,” he says. “And won’t be the last time, yeah?” He grabs your hand and lifts to his lips, placing a kiss on your knuckles before lowering it to a spot on his chest, near his heart. You can feel his heart beating against your palm, and you do your best to memorise the rhythm of it. You love the idea of it becoming the lullaby you’ll get to fall asleep to every night.

“I have a question,” you say lightly, your fingers beginning to trace invisible hearts across his chest, “what were you gonna do if you showed up here and I said no?”

Kendall chuckles as he adjusts his arms around you, bringing you in a little closer. “Yeah fucking right like you were gonna say no,” he says into your hair with a smile.

You roll your eyes as you crane your head back to look at him. “Well obviously,” you banter. “But seriously, if I hadn’t said yes, what was your plan?”

One of Kendall’s hands rubs up and down your upper arm as he thinks. “Honestly, I uh, I tried to not think too much about that,” he laughs gently, but it’s clear that the thought of his confession having gone bad makes him slightly uncomfortable. “I guess probably just transfer you to work with someone else… maybe ask Tom to, uh, swap you with Greg or something? I don’t know.”

You turn your head in surprise to face him. “Greg?! God,” you scoff as you settle back into his arms, “you are so fucking lucky I said yes.”

Kendall laughs deeply now, leaning down to kiss your cheek. You can feel the vibration from his laughter as he presses his mouth to your skin. “Hey, watch it, he’s still a Roy,” he warns jokingly in your ear.

“Right, right, my bad,” you smile as you lean your head into his. You both stay there for a moment, cheeks pressed against each other, Kendalls hands rubbing up and down your arms as he gently rocks you side to side. After a minute or two, he sits up a little.

“Stay here, I’m gonna go outside for a cigarette,” he says softly as his arms retreat from around you.

“You don’t have to go downstairs,” you offer as he climbs out of bed and you climb out after him. You pull on your tattered shorts and sweater as he grabs his jeans from the floor. “Just go out on the fire escape.”

Kendall buttons up his dark jeans as watches you open the window on the far side of your apartment and climb through. You sit down on the cold iron of the fire escape and peek your head back through the opening. “Coming?”

He smiles as he pulls a lighter and pack of cigarettes out of his pocket and strides over to you. After climbing through, he takes his spot, both of you sitting with your backs pressed against the exterior wall of your apartment building. The air is chilly, you can feel goosebumps beginning to form on your exposed legs. Kendall lights his cigarette beside you.

“So…” you say cautiously as a riskier question comes to mind, “you never mentioned… what changed?” You lean the side of your head against the brick wall as you watch him smoke. Barefoot, bare chested, in just his jeans - it’s a Kendall you’ve never seen before. You can tell that this casual, less put-together side isn’t something he shows many people, and it feels like a privilege to be one of the lucky few who gets to see him this way. But you’re still curious as to why he’s suddenly opened up this part of him to you.

Kendall takes a puff and exhales, looking down at the cigarette between his fingers as he speaks. “I uh… had a uh, I don’t know, I guess… an epiphany, while I was away.” He looks up and stares at the brick wall of the apartment building across from your own. He shakes his head a bit as he takes another puff and then flicks some of the ash off the tip. “Yeah, sorry, I really shouldn’t get into now… you’ll find out tomorrow. Jess will, uh, send the details in the morning, but I have a press conference at noon.” He looks over at you seriously. “I don’t want you going into the office tomorrow. I’ll meet you and Jess at the conference, and we’ll, uh, after it’s done, we’ll go from there.”

He takes one last puff before extinguishing the lit end of the cigarette on the iron rail of your fire escape. In no way has he answered your question, but if you’ll find out everything tomorrow… you suppose you can wait. You don’t want to ruin the night by making him discuss Waystar bullshit anyway.

“Okay,” you nod. “So if I’m not going into the office tomorrow morning, where should I be going?” you ask as Kendall climbs through the window and back inside, offering you his hand to help you through after him.

A smile finally returns to Kendall’s face as you re-enter your apartment and he leads you back over toward your bed. “Nowhere,” he grins, “you stay right here with me.” He removes his jeans before climbing back into your bed, pulling you in with him. He holds you tightly to his chest, laughing as you pretend to squirm in resistance. “Yeah, don’t even fucking try, you’re not going anywhere.”

You cease your wriggling and jokingly squint your eyes at him in suspicion. “Really? You’re giving me a sleep-in? On a work day?”

He grins again. “No, I’m giving us a sleep-in. Press conference isn’t until noon,” he says he leans down to kiss your cheek, “I’ll go back to my place in the morning to get ready.”

“Oh, do you think you’re invited to stay the night or something?” you quip, giving him your best look of mock-puzzlement. “I don’t remember doing that.”

You should’ve guessed that he wouldn’t take that kind of teasing lying down; Kendall doesn’t hesitate to call your bluff. He begins to unwrap his arms from around you as if he’s going to get out of bed. “Is that right? Okay, I can leave if you want, it’s not like I have a fucking penthouse waiting for me or anythi—“ but he’s interrupted by you pulling him back down beside you.

“No no I’m just kidding,” you apologise and you force his arms back around you, Kendall chuckling as you do. “You can stay.”

“Thought so,” he smiles as he holds you close, settling in for the night.

————————————

Kendall feels you nuzzle yourself into his chest, your skin still a bit cold from the outside air, and he wraps his arms around you tighter. The moment feels just as blissful as he imagined it would. Here, away from the bullshit of his life, he feels safe, he feels wanted, he feels loved. He looks down at you, your eyes closed gently as you begin to drift off to sleep, and silently thanks whatever force in the universe allowed him to experience this, right now, with you. Breathing a deep sigh of contentment, he closes his own eyes and falls asleep almost immediately.

***

Kendall wakes up, not at 5:30am, and not to the sound of his personally customised high frequency alarm, but after 8am to the light of the sun streaming into the room and the feeling of you gently rolling over in your sleep. His eyes open slowly, adjusting to how bright it is in your apartment. He’d forgotten what it was like to wake up to daylight. The blackout shades in his own place ensure that not an ounce of light enters his room before he’s ready, but even with your curtains closed, he can immediately tell that the sun is out. He looks over at the window in your sitting area and admires the way little slivers of sunlight stream through the cracks of your curtains, casting warm strips of golden light across the hardwood floors.

Somewhere in the back of Kendall’s mind he can feel the stress of his upcoming press conference starting to build, but he refuses to let it ruin his morning with you. He’s always been pretty good at sweeping things under the rug, and this is no exception.

He slides across the bed until your back is cradled into his chest, his arms snaking their way around you to hold you close, and hears you breathe out a soft sigh in response to his touch. Kendall smiles as he gives you a little squeeze and places a light kiss on your neck.

“Good morning,” he husks deeply as you emit a small groan in response to him waking you up. “Had enough sleep?”

“Noooooo,” you whine, your eyes still closed. “You promised me a sleep-in.”

Kendall smiles against your cheek. “What, 8am isn’t a sleep-in?” he teases.

“Of course not you fucking sociopath,” you slur sleepily, and Kendall gives a low chuckle. It’s fun to have someone talk back to him when it’s done lovingly.

He settles in again, pulling your body tightly into his chest. “Okay, you can have a bit longer,” he concedes, and you hum happily in response before he feels you slowly fall back asleep. Your breathing takes on a soft, steady pace, and Kendall tries to concentrate on the rhythm of it rather than let his mind wander to what this afternoon will hold. He does his best, but his brain can’t help from transitioning to strategy mode as he thinks about what he’s about to do. How he’s about to betray his father, his siblings, and possibly destroy the empire he was promised as a child.

Kendall runs through what he plans to say at the press conference, what he needs to get done when it’s over, who he needs to call… it’s a lot. Lawyers, PR agencies, and Waystar board members are just the start of who he has to talk to within hours of leaving the press conference. He’s going to need to try to get his siblings on his side as well, and no doubt he’ll experience some aggressive push back from his dad trying to strong-arm him into backing down.

His dad.

There’s no coming back if he goes through with this. He may get Logan sent to prison, but even if he doesn’t, his father is not a forgiving man. Though Kendall can recall very few moments when he felt even somewhat loved or respected by his dad, there’s no chance he’ll ever experience anything like that again.

Not to mention… his sister’s wedding.

His father not only knows about the worst night of his life, but has the proof and witnesses necessary to expose Kendall and let the world know what he did. That he’s killed someone. That he left a young man to drown.

Kendall’s heart rate quickens. He already considered the possibility of this when he decided to turn on his dad, but with the press conference only a few hours away, the reality of it is beginning to sink in. He has no good options - either he takes the fall and goes to prison for his father’s wrongs, or he calls him out, tears his family apart, and possibly goes to prison anyway. He feels his chest getting tighter and his breathing becoming shallower.

You begin to stir in his arms. Almost half an hour has passed now; half an hour of you sleeping peacefully while Kendall reflects on the tiny corner he’s been backed into. You must feel the tension in his body, the way his arms are stiff as stone around you, because you roll over to face him almost immediately upon waking up.

“Ken?”

————————————

You’re still waking up as you turn to look at him. He loosens his grip on you very suddenly, as if your movement has woken him from a daze, and when you’re finally face to face with him, he doesn’t look at you. It takes you placing your hand on his cheek and repeating his name again, softer this time, for him to raise his eyes to yours. They’re downturned, flat, sad. He looks like he’s been in a mental struggle all morning.

Your heart sinks. You fucking knew it. You knew this would happen, that he would take it all back the next day. You can’t believe that he’s doing this to you after all the things he said last night.
Your hand retreats from his face instantly. “Kendall,” you whisper and you can’t help the almost pleading tone that comes out as you say his name. “You changed your mind, didn’t you?”

Kendall immediately jolts to life. It’s almost like his eyes come back into focus from their glossed-over state. “What? No, fuck no, no, why would you say that?” One of his arms unwraps itself from you to comb a few strands of hair away from your face. “No, of course I haven’t changed my mind.” The mix of his words and the affectionate touch are enough to convince you that you were wrong. The tightness in your chest eases up a bit.

“Then what’s wrong?” you ask, your hand reaching back up to his face, stroking his stubbled cheek. “Is it because I called you a sociopath? I promise, I only kinda meant it.”

Kendall smiles half heartedly at your joke, but you can see his eyes slowly fading back to that glassy, lifeless state as he thinks about whatever has been troubling him.

“No… I, uh…” He sighs as he watches himself twirl a strand of your hair around one of his fingers. “Today is, uh… is gonna be a fucking big deal.” He lets the stand of hair fall from between his fingers. You feel it gently settle on the side of your face. “I’m taking a… an astronomical risk, that could, uh… yeah, it could ruin my fucking life.”

His gaze meets yours again and you can now see the pool of stress hiding behind the listless, dull look in his eyes.

You’re starting to realize what you’ve gotten yourself into with Kendall. Dating a man who has such a hard time allowing himself to be unapologetically vulnerable but who also clearly craves closeness isn’t going to be easy. You think you’re prepared to take on the challenge, you just need to be patient with him.

You reach to grab his hand, bringing it to the spot where your neck meets your chest and holding it there tightly. “Kendall, I know we’ve both been very… aware of each other’s presence at the office, but I had the opportunity to watch you a lot more than you did to watch me.”

Kendall’s eyes don’t leave yours as he listens. The despair you see in them tugs at your heartstrings, and you wish you could remove some of it for him, take it on as your own, but you know that whatever today holds for him is far above your responsibilities as both his assistant and his brand new girlfriend.

“And if watching how you operate has taught me anything about you, it’s that you’re smart as hell, and you don’t do anything half-assed.” Your thumb begins to stroke the back of his hand, and Kendall’s gaze lowers from your eyes to the spot where you’re gently touching him. “So… I don’t know what you’re in for today, but I do know that whatever it is, you’ve thought it through, and you’re capable of seeing it out until the end. And I’ll be there for you the entire time, whatever you need.” You lift your head from the pillow to kiss the edge of his jaw. “In and out of the office,” you say as you lay your head back down beside his, “we’ll do this together.”

Kendall’s gaze meets yours again, still looking sad. You’re not 100% sure because he pulls you into his chest before you can confirm it for yourself, but his eyes seem glassier, like they’re filling with tears. He removes his hand from your grasp and wraps both arms around you again, placing a kiss on your forehead as he holds you tightly. He doesn’t say anything, you just hear him inhale a shaky breath and exhale deeply before his breathing softens a bit. You don’t say anything either, you just enjoy the feeling of him holding you, knowing that this is probably what he really needs right now; to feel like he’s not going into this (whatever this is) alone.

You’re not sure how long the two of you lay there for, but eventually he begins to loosen his hold on you.

“I should, uh, go back to mine and get ready,” he says in a gravelly voice as he pulls away.

“Okay,” you answer softly, and you sit up in bed as he climbs out from under the duvet and begins to collect his clothing from around your apartment. He looks up at you as he pulls his jeans on.
“We probably shouldn’t do any more sleepovers during the work week just to, you know, minimize suspicion, but uh…” He looks around for his sweater, finding it on the floor and pulling it over his head. “… You should come over to my place this weekend.”

Oh… Shit.

You cross your arms over the duvet pulled up to your chest. “Okay, yeah… yeah, sure, let’s do that,” you offer lightly, and Kendall looks up at you questioningly.

“… Is that not okay?”

You let out a little sigh. “No, yes, of course it’s okay, I really would love to see your place.” You begin to fiddle with the edge of the duvet. “I’m just… I’m not sure I’m ready to see how much you’ve been slumming it when you’ve stayed here with me.”

Kendall chuckles as he walks back over to the bed, your innocent anxieties a welcome distraction from his serious ones. “Oh come on,” he grins as he sits down beside you, “don’t look at it that way. Think about it like… you get to reap the, uh, the rewards of fucking your rich boss by hanging out at his cool ass apartment.”

You laugh at the cockiness. “Wow, you’re so wise,” you joke. “And for future reference, that’s exactly how I want you to describe this relationship.”

Kendall smiles widely again as he leans in to kiss you, pressing his lips to yours firmly. You can feel how much he appreciates this moment, last night, and you in general through this simple gesture. He lingers there for a moment before unwillingly pulling away.

“I’ll see you in a bit, Ken,” you say gently, reaching over to grab his hand and giving it a light squeeze. He lifts the other one up to slowly tuck a strand of your hair behind your ear, taking an extra moment to look at you before leaning in again and placing a quick kiss on your cheek.

“See you soon,” he says as he rises from the bed. He heads for your front door, his eyes flashing to you one more time before he closes it behind him. Your gaze stays fixated on place you last saw him as you listen to his retreating steps pad down the apartment hallway toward the staircase.

The deja vu of the moment is hard to ignore. Sitting up in bed while you watch Kendall dress before he leaves to deal with some urgent business is exactly how your first night with him ended. This time feels very different though. This time, there’s a promise of a next time.

***

After receiving a text from Jess with the location of the conference, you get ready for the day and Uber over. You arrive just as many of the reporters do, and you’re shocked by the amount of them. The room is filled with cameras, microphones, and droning chatter as cameramen set up their equipment and journalists make small talk. Whatever Kendall has to say is going to be immediately heard by millions.

Jess greets you at the entrance to the room where the press conference will be held. “Hey,” she half smiles, “sorry for the last minute change. There’s a lot up in the air right now so I hope you’re okay being flexible for the near future.”

You nod. “Of course, whatever you guys need. Just… what…” you gesture around you, “what’s happening? What is this for?”

Jess gives a slight shake of her head. “I really don’t have that much information, Kendall hasn’t said much. I’ve spoken with Karolina though…” she looks over her shoulder where a woman with a short brown bob is typing on her phone, “and she seemed to insinuate that Kendall, um, might be announcing his culpability in the Brightstar incident.”

You feel your blood run cold. “Oh my god,” you respond, and you hope that Jess can’t hear the emotional distress that you’re feeling in your voice. “Why would he do that?”

She shakes her head again. “The impression I got was that Logan may have appointed Kendall as the, um… sacrificial lamb.”

You stare at Jess incredulously. “No,” you say, but it comes out as more of a question than a statement. “What— no, that’s fucking insane, why would he agree to that?”

Jess looks at you sympathetically, her eyes sad, and it’s clear that she’s watching you go through the same denial that she must’ve gone through earlier. “You haven’t been around long enough to really see it, but the power that Logan holds over him… it’s absolute.”

Jess’ phone suddenly buzzes in her blazer pocket and she pulls it out, scanning the screen before putting it away again. “That’s Greg, he and Kendall are almost here. We should go.” She begins walking in the direction of the building entrance.

Your thoughts are a scattered mess as you follow behind Jess. In some way, you know it makes sense; Kendall’s surprise visit last night, his sudden decisiveness in his desire for you, his strange behaviour this morning, it all paints the picture of someone giving himself what he wants before everything is ripped away from him. But at the same time… it feels like there’s a piece of the puzzle missing.

You can’t say that you know Kendall that well yet, but he definitely seems like the type of person who would collapse inward like a dying star when faced with a guaranteed prison sentence. He would isolate and disassociate and wither away until there was nothing left. He wouldn’t go after something as meaningful or serious as a committed relationship, and you can’t help but believe that he’s not the type of man who would bring you into his world with the knowledge that his life behind bars was about to begin.

… So then why the press conference?

None of it makes sense to you, and seeing Kendall doesn’t help. You exit the building and step out onto the street just in time to watch a large black car pull up to the curb. Jess opens the door to the backseat, allowing Kendall to step out. The stubble and casual clothing he donned last night are gone, the clean corporate look you’re used to making its return. The only change is that he’s added a pair of dark sunglasses, preventing you from exchanging any sort of look with him or allowing you to read any emotions in his eyes. It doesn’t matter though, he doesn’t even look your way. He nods in the general direction of you and Jess as he exits the car and follows her into the building silently. You and Greg trail behind, quickly saying hello to each other as the two assistants way out of their depth and uncomfortable not exchanging pleasantries. Why Greg is here, holding a yellow document envelope, is also a mystery.

The group of you return to the backstage area and Kendall removes his sunglasses. He still doesn’t look your way, but when Karolina speaks to him and informs him that his dad is watching, he doesn’t seem to actually be looking at her either. His eyes may as well be pointed inside his head, you can tell that he’s barely present in the external world.

Karolina leaves to announce the start of the press conference, and Greg and Jess take their places at the side of the room with their backs against wall. As you follow them out, you feel the lightest of touches on your lower back as Kendall walks past you. You turn to look at him and his eyes finally meet yours. His face is impossible to read, it’s the blankest of slates, but he gives you one minuscule moment of acknowledgement. His holds your gaze while nodding his head quickly a few times, and then turns away as he leaves to take his place at the front of the room.
You’re unsure what this gesture is supposed to mean. ‘It’s going to be okay?’ ‘I’m fine?’ ‘I’ve accepted my fate?’

You have no time to really consider it though because Kendall begins the conference and has you captivated from the very first second. He speaks in a steady, clear manner, allowing you to absorb every single word. He’s going to talk about the wrongdoings… he’s been asked to explain his role… he’s an appropriate choice for the public to blame…

“But…”

You’ve just begun to comprehend the beginning of Kendall’s statement, that he’s supposed to place a target on his back in front of the entire world, when he adds this transitional word and your mind grinds to a halt.

“The truth is that my father is a malignant presence, a bully, and a liar, and he was fully personally aware of these events for many years and made efforts to hide and cover up.”

Oh my god.

Oh my god oh my god oh my god.

The entire room erupts in gasps and mummers of disbelief, and Karolina has begun to type frantically on her phone next to you, but you don’t move an inch or make a sound. You don’t even want to blink lest you miss a milisecond of Kendall in this moment.

You’re vaguely aware that he’s continuing to denounce his father, but you’re barely hearing a word of it. You’re focused instead on the tone of his voice, on his steady eye contact with the crowd and cameras, and the continuous stream of cutting words that he seems to be coming up with on the fly. It’s fucking mesmerising and you’re reminded of how you felt when you watched him testify in congress, but he power he has when you’re actually in the room with him is tenfold.

Kendall stands as he finishes his statement, reporters beginning to swarm him as he rips up the prepared note cards he had been given and tosses them aside. Your stomach lurches as he exits the stage and strides through the crowd, ignoring their frantically shouted questions as he heads in your direction. He looks like a god amongst men, the authority that’s radiating off him almost bringing you to your knees. He locks eyes with you momentarily, his gaze stern and serious, and you’re reminded that this intimidating figure, this untouchable man, is yours. He’s finally yours.

Chapter Text

The next few minutes pass by in a blur.

A security team hurries to escort Kendall to a room in the hotel, with you and the rest of his entourage following closely behind. You feel like you’re on autopilot, not taking in your surroundings or considering what happens now; your body seems to be solely focusing on following the pack. At one point, you feel yourself turn to look at Jess and try to read her reaction. As the much more seasoned assistant, her feelings about this will tell you how you should be feeling about it. She offers nothing though. Her eyes are wide but she keeps her gaze focused forward no matter how many times you glance her way. You get the sense that she’s refusing to look at you, like she’s trying to piece together how she feels about what just happened before she commits to one reaction.

The group finally reaches the hotel suite and you all pile into the room, the security team quickly shutting the door once everyone is inside. Your immediate instinct is to look around for Kendall, and your gaze locates him just in time to watch him stride into the bathroom and firmly shut the door behind him. You hear the lock turn. The group is silent as you all look at each other, wondering what to do now.

“Let’s give him a minute,” Karolina offers before sitting down on the plush white bed and returning her attention to her phone. She begins to type furiously as her device buzzes over and over again.

You take a seat in an armchair in the corner of the room, Jess taking the spot next to you and pulling her phone out. She keeps her head down as she navigates from one website to the next, likely taking stock of the general public’s immediate reaction to the conference. You wish she would even slightly indicate to you how she’s planning to approach the situation - this is by far the most out of your depth you’ve felt since starting at Waystar (which is saying a lot) and you’re really relying on her to lead by example right now.

Unsure of what to do, you watch Greg stand awkwardly by the bathroom door. He paces back and forth in front of it, seeming to be in an internal debate if he should knock or not. After a minute or so, he suddenly stops short and awkwardly calls out through the barrier.

“Ken…? Are you okay?”

When no response sounds from the bathroom, your thoughts immediately flip from the difficulty of your own situation to the severeness of Kendall’s. His anxiety this morning makes perfect sense now, and you can’t blame him for thinking that what he just did might end up ruining his life. That’s definitely not something you can admit though - he’s going to hear enough of that from lawyers, publicists, his own family… He needs someone to tell him he’s gonna make it through this.

You pull your phone out too and open your messages app, scrolling down to find Kendall’s name. You sit and think for a moment before typing out two simple sentences.

“So proud of you Ken, you fucking got this. We’re in this together.”

You don’t think before pressing send, but you immediately feel stupid as your text is marked as ‘delivered.’ You should’ve said something more motivational, more supportive, more meaningful… Kendall is probably spiralling on the other side of that door, one text isn’t going to do anything.

Well, it’s too late now. You lock your phone and place it on your lap, retuning your attention to Greg as he continues to flounce around in front of the bathroom. He leans toward the door and calls through again.

“If you’re okay will you just say okay so I know you’re okay? Otherwise I’ll have to break the door down… and I don’t really want— I don’t know if I’ll be able to…”

Greg trails off as he eyes the doorway, looking for its non-existent weak spot, but there’s no need. The door swings openly suddenly and Kendall exits the bathroom, looking determined. He speaks as if his last few minutes of isolation never happened and you’ve all just entered the hotel suite together.

“Okay. Action stations. Let’s fucking go, let’s get into this.”

The room comes to life immediately as people jump up from their spots. Kendall begins to call out orders, asking you and Jess to contact certain publicists and lawyers, Greg to keep an eye on his ‘cultural temperature,’ and Karolina to get the car ready to bring him to the Waystar offices. He gives a subtle squeeze to your waist as he moves by you, a secret acknowledgment of your text.

“That’s a company car Ken…” Karolina points out hesitantly. “I’m not sure you’re still an employee of Waystar, considering…” she trails off as Kendall stares intently at her.

“What I did was to protect the company. I had Waystar’s best interest in mind, and uh, I’m still on the fucking board.”

Karolina’s mouth sets into a hard line. “I don’t know if that’s how the rest of the board will see it…”

Kendall crosses his arms up against his chest as he stares her down. “Are you in, Karolina?” he asks impatiently. With the current situation, there’s even less dancing around confrontation than usual. “This is a fork in your life, this is the righteous path. I can’t have fucking Russians in my situation room - if you’re not Team Ken, you uh, you better jump ship now.”

“Kendall…” Karolina huffs defeatedly. Her one word reaction tells him exactly what he needs to know. He doesn’t hesitate as he turns to Jess and instructs her to call the car around, and he doesn’t look at Karolina again as the group prepares to leave the hotel room.

His ability to completely disregard someone who no longer has anything to offer him is somewhat shocking to watch. You know that it’s just business and he needs to make hard decisions in order to survive the war he just started, but still… you wonder if he is also capable of cutting personal ties that quickly.

There’s no real time to think about it too deeply as your body returns to autopilot and you follow the group down to the car. It’s harder for you to stay dissociated though as Kendall exits the building and is immediately swarmed by news crews, camera flashes, and reporters desperately shouting their questions over each other. Kendall somehow walks through the crowd as if he’s completely alone, like there aren’t dozens of people jostling around him and yelling in his face.

It’s very quiet all of a sudden as you climb into a large black SUV and the door is closed, blocking out the noise from the street.

“To Waystar?” Jess confirms with Kendall. He nods, his eyes locked on his phone as he watches texts, emails, and social media mentions flood his screen.

The car begins to move, leaving the crowd of reporters behind. One of them pounds on the exterior of the glass as the SUV pulls away from the curb and Greg gives a half-assed “Cool it buddy!” through the window, but you barely react. Your gaze is locked on Kendall’s side profile as you sit diagonally behind him, noticing every small raise or lower of his eyebrows, every minuscule twitch of the mouth. You watch him carefully, the same way you have since you started working at Waystar, but this time with different intentions. It feels like you’re getting a crash course on how your boyfriend deals with extreme stress.

His face suddenly changes drastically and takes on a sort of scared-surprised expression. When you watch his shoulders tense up too, you can immediately guess what’s caused this reaction - Logan. Kendall acted the exact same way when his father called him the morning after your first night together, as well as the night you kissed in his office. Your suspicions are confirmed when Kendall turns around and holds his phone up to you and Jess, his screen showing “Dad” on the caller I.D.

“Do you want me to-?” Jess asks, and Kendall nods as he holds the phone out to her. In this moment, he almost looks like a scared child. It’s another new piece of insight you’re getting into your boyfriend; no matter how high he is on the pedestal of power and authority, there’s still one person with the ability to knock him to ground.

You do you best to ignore the conversation between Kendall, Logan, and their middle-man Jess as it happens beside you, instead texting Remi, one of the executives at Waystar who has already claimed his spot on ‘Team Ken.’ Remi has been keeping you updated on the goings-on at the offices since the press conference, making sure that Kendall knows if he’s going to be ambushed when he arrives. It’s just as Kendall takes his phone back from Jess that Remi sends you an update text.

“They’re trying to cancel Kendall’s access card.”

You read the text aloud before looking up at Kendall and then over at Jess.

“… They can’t do that, can they?” Kendall asks to no one in particular.

“I don’t know… but it sounds like they’re going to anyway…” Jess responds hesitantly.

Kendall sits up straighter in his seat. “Okay… well, fuck… my place?” he suggests, and you’re beyond relieved when Jess shakes her head.

“There’s press outside.”

Thank god. The last thing you want is to see Kendall’s place for the first time while on a business field-trip with Jess and Greg.

“Okay, then… Rava?”

Kendall offers the name cautiously. Who’s Rava?

Jess raises her shoulders slightly. “Uh, yeah, that could be an option… I think maybe, um, you should be the one to call though…?” She phrases the last sentence like it’s a question. Who is so important that Jess thinks Kendall needs to personally ask for a favour?

Kendall nods wordlessly, unlocking his phone and selecting a number from his contact list. You hear a woman pick up on the other end. Kendall’s tone with her is familiar but still polite.

You can’t help it, you need to know. You lean over to Jess as she types on her phone next to you.

“Who’s Rava?” you whisper as quietly as you can manage over the gentle hum of the SUV.

“Kendall’s ex-wife,” Jess responds, her eyes never leaving her screen.

You lean away from Jess as if she’s slapped you.

Maybe you shouldn’t be this surprised; Kendall is in his late 30’s, of course he’s had time to date, fall in love, get married, and then fall out of love with someone. But still, this is a massive part of Kendall’s life that you’re discovering in the worst circumstances possible. You internally curse yourself for being too scared to google Kendall; you could’ve saved yourself from being blindsided like this.

Kendall hangs up the phone. “She said it’s cool, let’s head there,” he confirms before calling up to the driver and changing the destination to ‘Rava’s place.’

You can’t help but disappointedly stare down at your lap. You’re not sure what’s worse - that Kendall was married and this is how you’re finding out, or that you just started dating him last night and now you’re on your way to his ex-wife’s house. Probably the latter.

The drive is quick - Rava is wealthy enough (or became wealthy enough through her marriage to Kendall) to afford to live just outside of the financial district. It isn’t long before the SUV pulls up to the curb outside a beautiful old building.

'Of course she has good taste,' you think bitterly.

Kendall’s driver exits the car and walks around to open the passenger door. As the four of you climb out, Kendall gives a quick nod to the driver.

“Hang out for a second Fikret, Rava wants you to go pick up Sophie and Iverson and bring them to her Mom's. I’ll text you where they are.”

You look over to Jess, a questioning look on your face.

“His kids,” she mouths silently.

KIDS?!

Chapter Text

You can’t bring yourself to look at Kendall as you ride the elevator up to Rava’s apartment.

In your periphery you can see his eyes flash in your direction a few times, but your gaze doesn’t budge from the distorted reflection in the elevator’s metal doors. You’re positive that he wants to exchange some sort of look with you, maybe an apologetic one for dragging you to his ex-wife’s place. Or maybe he expects your expression to tell him how exactly how you’re feeling about being here, but you keep your face blank and eyes set forward. You can’t tell yet if you’re mad or embarrassed or jealous or overwhelmed… maybe a mix of all of the above. You only know that sharing a secret look with Kendall right now is going to confuse you even more. You just need to get through this next part on your own. Just see the ex-wife and go from there.

The elevator doors open directly into Rava’s front hall. Immediately you can see that the decor is bright, warm, and stylish. It smells like verbena. Fuck.

Kendall strides confidently out of the elevator and into the apartment. He always seems like he belongs in every room he enters, but with the way he carries himself now, you can’t help but wonder if this was the home he and Rava shared.

Jess follows a few steps behind him with you and Greg trailing even further back, very aware that you are taking up space in a stranger’s house.

“Just chill here for a sec,” Kendall says lowly as he enters the living room, and then you hear a confident “Hello hello,” as he turns a corner and greets Rava.

You approach the doorway to the living room and stand beside Jess, peeking into the space as nonchalantly as you can. Your eyes scan over the room quickly, taking in the natural light, warm tones, and refined furnishings. God, she really does have good taste.

Your gaze continues to move across the room until it reaches her - Rava, and she’s not what you were expecting at all.

Well, that’s not exactly true. You expected beautiful, and she’s definitely beautiful. But she’s also… effortless. Understated outfit, minimal makeup, simple jewellery. For some reason you had pictured Kendall marrying someone who liked to show off a bit more, maybe someone who liked to be noticed, feel glamorous… seem more obviously high status. Gorgeous apartment aside, that doesn’t seem to be Rava’s vibe.

You watch her as she talks to Kendall, a friendly smile on her face, and you strangely feel your emotions toward her start to change. Yes, you were missing a huge piece of Kendall’s past in not knowing that he had been married, but seeing the type of person he chose to be committed to and have children with… it offers you a strange sense of assurance, having concrete evidence that Kendall seeks out some element of normality in a partner.

You also have to admit that if you’re going to meet the mother of Kendall’s children, this is a pretty ideal situation for it. You’re less likely to experience any hostility from Rava if you’re seen as a random assistant instead of her ex-husband’s younger new girlfriend.

Maybe this whole thing isn’t as bad as you made it out to be.

Rava gives Kendall permission to bring the team in and you’re soon following Jess over to a large dining room table. As you begin setting-up a makeshift workspace, Kendall and Rava move to another room to continue talking. You momentarily consider what they might have to discuss (it keeps slipping your mind that Kendall has children), but your thoughts are soon otherwise occupied as lawyers and publicists begin to stream into the apartment as well.

Once Kendall’s temporary headquarters have been set up, everyone gets down to work. You and Jess work together closely as you do damage control, which includes a lot of fielding calls from news outlets, board members, and pissed off family members. You’re so distracted with work that you actually begin forget how much how much has been thrown at you in the past 24 hours (Kendall’s late night visit, his press conference, HIS EX-WIFE AND KIDS).

Surprisingly, the same cannot be said for Kendall.

He walks over to you and Jess at one point and leans over a chair stationed on the opposite side of the table, his hands gripping the back of it.

“Can you forward me the number of that Times reporter?” he asks deeply, his attention directed to you as Jess speaks to a board member on the phone.

You glance up from your work to nod quickly. “Already emailed to you,” you respond but Kendall shakes his head.

“Text,” he requests. "Please,” he adds before walking away.

You reach over for your phone, which has been lying face down on the table for the past few hours. You have a number of missed notifications, but only one of them catches your eyes immediately. A text from Kendall: “Quick talk, bathroom down the hall in 10?” It’s from over an hour ago.

You look over to where Kendall is now sitting with one of his new publicists. He must feel your eyes on him because he looks up, and you mouth a “sorry” as subtly as you can. He smirks slightly as he directs his attention back to the publicist, but you notice him discreetly tap his watch as if to say “in 10.”

Though the last few hours have flown by, the next 10 minutes seem to crawl. Kendall eventually excuses himself, saying something about taking a call. You don’t bother to make an excuse, Jess is still on the phone and you’re pretty sure that no one else on Team Kendall gives a shit about what you’re doing.

You walk down a hallway that leads further into Rava’s apartment, feeling more and more like an intruder with every step you take. There’s only one door that’s closed, so praying that it’s the bathroom with Kendall in it, you step inside and quickly shut the door behind you.

Kendall is standing in the centre of bathroom, his hands in the pockets of his trousers. He doesn’t make a move to touch you, he doesn’t say anything, he just looks at you with an unreadable expression on his face. You stand there for a moment as well, deciding how you want to play this. Now that you can speak freely, you’re beginning to remember how upset you were about being so kept out of the loop. For fuck's sake, even now, you're having a secret meeting in his ex-wife's bathroom.

Kendall's eyes are wide and anxious though. He looks ready to explain himself if he needs to, but also exhausted from already having done that dozens of times today. This one look is enough to disarm you - you can't bring yourself to be mad at him. This may be the most important day of Kendall’s life and it'd feel cruel to throw your personal feelings on top of everything he's already dealing with.

You take a few steps toward him and he’s immediately ready to pull you into his chest.

He holds you tightly there for a few seconds before you feel him reluctantly loosen his grip on you, his hands slowly retreating from your back. Your little meeting can only last a couple minutes and you have other things to discuss.

“So… wow,” you begin, reaching to hold his hands in yours. “Was not expecting any of this from today.”

“Yeah… I, uh, yeah. It… it’s a lot.”

He nods, more so to himself than to you as he looks down at your hands.

“… fuck, had to happen though…”

He seems to zone out for a second, staring blankly at the floor before he shakes his head, jostling himself from his thoughts.

“Got the best of the fuckin’ best working with us though, I’m gonna crush this thing.”

He sounds confident, but there’s a slight waver in his tone, like he’s trying to convince you and isn’t sure you’ll believe him.

You look up at him questioningly. “Of course you are,” you say like it’s the most obvious thing in the world. “I meant what I said this morning Ken, I have no doubt that you’re gonna come out on top. I’m so proud of you for taking such a huge risk,” you say as you squeeze his hand. “I can’t wait to watch it pay off.”

It’s not an exaggeration to say that Kendall’s eyes light up as he leans in to kiss you, taking you by surprise as his lips move furiously against yours. He pulls away before you’ve even had the chance to enjoy the moment, and you feel a rush of blood to your cheeks, your body struggling to catch up to Kendall’s burst of passion.

“And so you’re, uh, cool being here?”

His hands don’t settle anywhere on you, they excitedly move from caressing your cheeks to stroking back your hair to running up and down your arms. He can’t seem to stop fidgeting, the mix of adrenaline from the press conference with the ego boost you just gave him seeming to produce a powerful energetic effect.

You smile softly, reaching for one of his hands in an attempt to slow him down. You would bet money that his heart rate hasn’t dipped below 100 bpm since this morning. “I mean, I wish I had known that there was a here before I had to come up, but it’s been… interesting, you know, to learn about this side of you.”

Kendall’s face falls, and his hands halt completely. His eyebrows furrow together slightly as he pieces together what you mean.

“The fuck are you talking about?” he questions, shaking his head. “You didn’t know I'd been married?”

You look off to side, avoiding his intense eye contact. “You didn’t say anything, so no,” you try to say as confidently as you can. It sounds stupid coming out of your mouth now, there are so many ways you could’ve learned that information without Kendall having to outright say it to you.

You can see his expression change in your periphery from one of confusion to something a little more cheeky.

“What, have you not googled me yet?” he asks, and you can hear the amusement in his voice. You turn to look at him and the intense gaze has morphed into one of entertained disbelief.

You’re definitely embarrassed now, and also a little pissed off that you’re being made to feel stupid for not going out of your way to google Kendall’s history. You made the conscious decision not to do so, thinking it would be weird to admit you knew things that he had never told you, but now it seems like it’s weirder that you don’t know those things.

“No, I didn’t. Was I expected to take notes from your Wikipedia page or something?” You avoid making eye contact again, desperately trying to not show that you’re second guessing your choice to stay in the dark.

“No,” he chuckles, “it’s just that I can’t say that I didn’t, uh, look into you,” and his leans in to press his lips to yours again. You can’t help yourself from breaking into a smile.

“You googled me?” you laugh lightly as he pulls away, your brain racing through all the possibilities of what he could’ve seen. “Find anything?”

“Nice try, we’re not doing a fuckin’ one sided show-and-tell here,” he quips, his arms wrapping around your waist as he grins down at you. “I went in assuming you knew everything, I’m gonna have to reevaluate my strategy here.”

Your arms reach up to wrap around his neck and though you roll your eyes at his comment, there’s a grin on your face to match his. “Just checking, but you do know that dating isn’t the same as a corporate takeover, right?” You raise your eyebrows at him. “There’s no need to devise a plan to get me if I’m already yours.”

Kendall’s expression softens slightly as he leans in to press his mouth to yours again, less frantically this time. The kiss is deep, purposeful, and you can feel that beneath all the chaotic energy of today, this is safe for him. Grounding. Real.

Forcing yourself to break away feels impossible but you manage to slow your movements. Kendall follows your lead and pulls back, but only barely. He presses his forehead into yours and his hand reaches up to gently hold the side of your face. You savour what you know will be the last moment of affection for awhile, your head leaning into his hand. He presses his forehead into yours a little more.

Kendall inhales a deep breath as his fingers pass softly across the skin of your cheek. His hand gently drops from your face as he exhales the breath slowly, and you know what’s coming next. The second the air has left his lungs, he snaps back into work mode.

“We should go back” he says lowly, his head pulling back from yours and his posture straightening. You nod in agreement. The moment was nice while it lasted.

Your eyes are directed down to the floor, waiting for the moment he picks up his feet to leave the room, but the moment doesn't come. You look up at him in confusion, only to see that he’s also looking down. He doesn’t look up as he begins to speak.

“I… yeah, I,” he husks as he searches for the words he wants to say. “I’m uh… I’m happy you’re here.”

You can’t stop a light laugh from escaping. You were expecting him to say something a little more serious with that kind of hesitation, but you’re quickly learning that Kendall’s stutter closely corresponds with moments of vulnerability.

“I’m happy I’m here too Ken,” you smile at him, badly wanting to go back in for another kiss but unsure if you’ll be able to stop once you’ve started again.

Kendall nods, briefly raising his eyes to meet yours before he swiftly places his hands on the sides of your face and leans in to kiss your forehead. You feel him linger there, his thumbs brushing across your cheeks, and then his lips and hands are gone.

"See you out there," he says. The stutter is gone.

Kendall brushes past you as he makes his way for the bathroom door. You watch him pause momentarily as he reaches for the doorknob, just for a beat, before he pulls it open and strides out, closing it behind him.

You count to 50 before following him out.

Day turns to night and then late into the night, but Team Kendall is still full steam ahead. Jess, who you’ve noticed often has to remind Kendall that humans need to eat, eventually suggests getting food for everyone.

“Oh, yeah, sure,” he agrees offhandedly, his attention locked on a written statement his PR team has crafted. “Can you guys take care of that?”

Jess tasks you with going around and asking how many people want food (surprise surprise, it’s everyone), but you take the initiative to also ask Rava if she would like anything. You doubt she’s happy about Kendall completely taking over her home, so you figure that buying her dinner is the least he can do.

You find Rava in the kitchen, typing on her phone as she waits for a kettle to boil. A mug with a teabag sits ready on the counter.

She instinctively glances up as you enter, her gaze quickly falling back to her phone as she tries to avoid an interaction with another one of the strangers in her home.

“Rava, right?,” you start hesitantly. “Sorry to interrupt.”

Rava sighs, locking her phone and placing it on the counter beside the empty mug. “No, I should expect it by now. At least the entire team is consistent,” she says with a tight smile.

Shit. Not a good start.

“Oh, um, yeah, sorry" you apologize again. "It's really generous of you to let us set up here though. Everyone, Kendall especially, really appreciates it.”

Rava doesn’t respond. She cocks her head slightly to the side and nods, the tight smile still present on her face, but there’s no verbal attempt to accept your gratitude.

“Um, well,” you stutter. She doesn’t even know you’re dating her ex-husband and she already hates you. “Kendall is ordering food for the entire team so, uh, I just wanted to see if you’d like anything.”

Rava’s face releases from the tight smile. “Oh, no thanks. I think I’m just gonna bring my tea to bed and try to sleep while dozens of strangers stream in and out of here like it's some sort of open house.”

You let out a light exhale of a laugh. You can't help it; the way she's worded it really shows just how ridiculous this situation is for her.

Rava narrows her eyebrows at you, her gaze so harsh that you immediately realize that she must think you're laughing at her situation.

"Sorry, it's- yeah, it's just even more obviously insane when you say it like that."

Her intense stare lessens as you continue.

"Seriously, putting up with all this, you're so much more... tolerant... than I would ever be in this kind of situation."

Rava scoffs as she turns away from you, the kettle on the stove beginning to whistle. When she speaks, her tone suddenly seems far more conversational instead of dismissive. "Comes with the territory," she says.

Rava pours hot water into the waiting cup, lifting the teabag in and out of water few times before delicately wrapping her fingers around the mug's handle and turning back to you. She leans against the counter again.

"Sacrifices need to be made when you're in Kendall's life," she says as she looks out the doorway of the kitchen to where Team Kendall is set up. "And as you can see," she lazily gestures in their direction, "that continues even when you're not in his life."

You nod. You've clearly seen that Kendall's career does not make for easy living. "Yeah, I can imagine that the nonexistent work-life balance and the never-ending PR strategizing would be a lot."

You're surprised to watch Rava laugh lightly, but there's little humour in it. "I mean, yeah, that's some of it." She crosses one arm over her chest, her other hand still holding her mug of tea. "But I'm sure you've seen his personal ups and downs too."

She looks at you expectantly.

Your blood runs cold.

Does she know?

"Uh, yeah, like, I've seen him get stressed but he usually seems to handle the pressure pretty well?" You phrase it like a question, knowing it's likely not the response she's looking for from you.

She lets her face get half hidden by her mug as she takes a tentative sip and raises her eyebrows. Yep - definitely not what she was looking for.

"Sure,” she dismisses. "But how's he actually doing?"

It hits you that this is why she's still here talking to you in the kitchen and not confining herself to her bedroom like she said she was going to - wanting insider info on the ex-husband that just made a huge public scene.

You shake your head and lift your shoulders in a quick shrug. "Good, I think? Obviously Waystar hasn't had an easy time lately but he's handled it well and is intent on making necessary changes to the company." You shrug again. "I don't know, he seemed to be really sure that what he did today was the right move, and that he'd considered all his options and this was the best one."

Rava gives a knowing dip of her head at that last sentence. "Yeah, well, coke makes him feel confident about pretty much every decision."

You're taken aback for a moment, shaking your head quickly in response to the accusation.

"What? No, Kendall doesn't... I mean, I don't know about his free time but he's not high for work stuff.”

Why would she say that?

Your mind begins to race through your interactions with him in the office. He's never left his office or come back from the bathroom seeming overly manic or energized, you haven't noticed an excessive amount of sniffing, his pupils being dilated, powder on his hands or clothing... Seriously, why would she say that?

Rava smiles at you the way you might smile at a child who's just asked a mind numbingly stupid question. "How long have you worked at Waystar?"

"... Not long," you respond sheepishly, "only a few months."

She nods knowingly as she turns around and places her mug on the counter. "He's good at hiding it," she muses, lifting the teabag from her mug and letting it drop into the sink with a dull thud. "Waystar always has him at 100 so it'd be less noticeable in a high pressure setting." She picks the mug back up and faces you again.

"It's a little more obvious when you're living together and coming home to find white residue on your kids' iPads."

Jesus Christ.

"That's... wow, I'm sorry," is all you can think to say. Your mind is a bit distracted by that gut punch of an anecdote.

She brushes off your condolences. "It is what it is, I'm just pretty sure that today was another manifestation of that habit rearing its ugly head." She sighs, and you can hear years of frustration in the sound. "Those pretentious rehab retreats are useless."

You're struggling to wrap your head around what Rava is revealing; not that Kendall uses cocaine, that's pretty much a given for anyone working in finance in Manhattan, but that he's struggled so deeply with substances that it’s affected his home life and resulted in him checking in to rehab.

You struggle to dismiss the realization that most of what you've learned about Kendall today could've been revealed in a single Google search.

Still though, you're not a naive or oblivious person. You're positive that you would've noticed Kendall using coke at least once since you met. The first night you spent together, the many hours at the office, last night... nothing comes to mind. You know what coked out looks like and you definitely haven’t seen it with him.

"I... I don't doubt that you've had to deal with a lot with Kendall, but I really do think that today was a sober decision." You raise your eyes to Rava's. "He fully knew and accepted what he was getting himself into with that press conference."

You can feel that your face has morphed into an almost pleading expression.

She looks at you sympathetically, likely seeing a young employee who wants to believe the best of the man she works for rather than come to terms with the fact that she's being bossed around by a coke-addicted nepo baby. She thankfully doesn't see the new girlfriend whose feelings for Kendall means she's noticed his every move and overanalysed every interaction. You're positive that there's no way you missed something so significant.

You watch her as she decides to take pity on you.

“You know what? I'm sorry, I shouldn’t’ve said anything.” She shakes her head and holds her hands up in a gesture of innocence. “If you haven’t seen anything, maybe he is actually clean."

She makes direct eye contact now, and you can almost see her reliving past memories. “Just... you know, keep an eye on him for me anyways."

You nod as she places her mug in the sink and grabs her phone from its spot on the counter. "It was nice to meet you," she offers as she walks past you, out of the kitchen, and then out of sight.

You return to the group and Jess places the food order, but after that, there's not much else for you to do. The work is solely strategic at this point and as your opinions are of little value in this situation, you struggle to find something to keep yourself busy with. Jess eventually catches you yawning at your laptop screen as you browse through emails in an attempt to look like you're busy.

"Hey," she says to you lowly as she leans across the table. "You can probably head out for the night. Would be good for at least some members of the team to have a clear head tomorrow."

You don't argue. You're exhausted.

Kendall is, of course, surrounded by other members of his team as you're leaving, so you don't attempt to grab his attention. The most you can do is pull out your phone in the elevator and send him a simple message: "Jess sent me home. Let me know if you need anything."

You hesitate momentarily before adding a heart emoji to the end of the text.

You somehow make it back to your apartment, but the day has been so mentally draining for you that you aren't awake for long. You're asleep before your head even hits the pillow.

***

You’re awoken by the sound of your phone ringing next to you on your nightstand. The light of the screen is blinding, it takes a few seconds for your eyes to adjust enough to see who’s calling, but you don’t hesitate to pick it up when you make out a blurry capital K.

“Hello?” you murmur into the phone, and you can hear the sleep in your own voice.

“Hey,” Kendall’s low voice greets you softly. “I’m— there’s still press at my place, is it— I’m outside, can I, uh, can I come up?”

It takes you a moment to comprehend what he’s saying, you’re still half asleep, but you sit up immediately when you understand that he’s waiting downstairs right now. “Yeah— yes, of course, hang on.” You stumble out of bed and to your intercom system, quickly pressing the button to unlock your building’s front door. You hear the buzzer sound through the phone as Kendall pulls the door open.

“See you in a sec,” he husks before hanging up.

You wait where you’re standing - one of the other downfalls of this old building is that the apartment doors lock automatically, you can’t just leave it open for Kendall. He doesn’t make you wait long though, he’s knocking on your door less than a minute later.

You pull it open, your eyes preparing to adjust to the light from the hallway, but there’s no need. The second the door is out of the way, Kendall is all over you. You feel his hands cup your face, his lips press firmly into yours, and he breathes in deeply through his nose, as if kissing you is oxygen that he’s been deprived of for hours.

Your mind is still hazy from sleep, but your body has no issue following Kendall’s lead. You melt into him instantly, quickly matching the deep, slow rhythm of his lips. Just as you feel the butterflies in your stomach waking from their slumber, Kendall gently pulls away.

“Thanks,” he murmurs into your hair, his hands moving from your face to wrap his arms around you, “for letting me come by so late again.”

“Anytime,” you say softly into his chest. He smells like cigarettes mixed with expensive cologne - a scent you used to associate with rowdy strangers you’d met on late nights out, but is quickly becoming the most comforting smell in the world. “C’mon,” you say, gently pulling away, “you should sleep.”

You pad back over to your bed as Kendall undresses behind you, stripping down to his underwear before climbing under the covers with you. He sighs as he pulls you in, his entire body seeming to release most of the tension it’s been holding the second he has you back in his arms. “Sorry today was such a fucking mess,” he whispers, one of his hands running up and down your arm. “You know that I, that I didn’t mean for the… uh, the ex-wife and kids thing to be fuckin’ sprung on you like that.”

You keep your head tucked under his chin. “I know,” you murmur, “it’s okay, it’s kinda how relationships work. You find out things as you go.”

You feel Kendall’s lips press against your forehead. “Yeah,” he say lowly. “There’s a lot…” he pauses as he strokes your hair, “uh… there’s a lot you might hear about, you know… before I get the chance to tell you myself...”

You consider if now is a good time to bring up what Rava said - give him the opportunity to tell you about his substance abuse history before it gets mentioned in some article or news report.

The team’s job is to constantly stay updated on what is being said about Kendall in the press, so there’s no way you'd be able to pretend that you didn’t see it. You can’t imagine how he would feel if his struggle with substances became a PR strategy group discussion before he got the chance to discuss it with you privately. And you yourself would hate to have to learn personal information about him in a work setting again. Maybe now could be a good time to also let him come clean about anything else that could come up…

Your attention falls back on Kendall’s arms, firmly wrapped around you like a child hugs their teddy bear after a bad dream. You can feel how much comfort this physical contact is bringing him, how much stress is still contained in his body, and how much he needs this moment of refuge from the outside world.

In an instant, all thoughts of confronting him about Rava’s comment or discussing anything at all are pushed from your mind. You can’t introduce another element of stress for him, not today.

You lift your face and place a kiss on his jawline. “I know,” you whisper. “But that’s okay. We’ll take it as it comes.”

Kendall breathes out deeply and you feel his arms give a gentle squeeze around you as he sinks deeper into your bed, letting himself momentarily let go of today. You know it’s temporary, that in a few hours he’ll wake with the same frantic energy and urgency to get things done, but for now, you get to just fall asleep beside your boyfriend.

‘We’ll take it as it comes,’ you repeat softly, Kendall already half asleep beside you. With his arms wrapped around you and his breathing beginning to deepen, the world feels a little more right.

You just find yourself wishing that the comforting words were coming from his mouth rather than your own.

Chapter Text

Kendall only sleeps for 3 hours before his nervous system jolts him awake, reminding him that there's shit to do.

He sits up quickly, his heart already pounding in his chest as he remembers yesterday's events and how much of his life hangs in the balance.

Recalling the late night meeting he had with his siblings at Rava's (and the complete and utter shit show that it was) doesn't help either. It's forced him to come to terms with the fact that he's 100% alone in this, and that the work that needs to be done in order to take down his dad is now 100% up to him. Fuck.

You stir in your sleep beside him.

Kendall turns to look at you, finding you curled up and facing away from him. His half-asleep and stress-addled mind hadn't even registered that he had woken up next to you in your bed.

He instinctively reaches a hand out to you, his fingers finding the base of your neck before trailing across your shoulder and then down your arm. He watches your sleeping body curl into itself even tighter, his light touch having sent goosebumps across your skin. He feels the corners of his mouth turn up slightly.

Right. Not 100% alone.

But not 100% not-alone either. Yes, you told him before the press conference yesterday that you would be with him through whatever came next, and he doesn't doubt that you meant it, but it can't happen. It's too much.

He knows you're smart and hard working and competent, but you're also young, and relatively inexperienced, and... important. He doesn't want you in too deep with the messy legal shit that he's in, but more importantly, he doesn't want you in the same room as him if he flips out because something's gone wrong.

Kendall is painfully aware of how much of an asshole he can be in those kinds of situations. The way he treated Shiv last night when she refused to switch to his side is far from his proudest moment. He can breathe easy knowing that you weren't there to see it, but if that situation were to repeat itself in front of you, he knows there's no way you'd ever look at him the same way again (if you even wanted to look at him at all).

No way he's letting you see him act like that, especially not this soon. It'll be better if he can avoid bringing you in the loop until he can get the more high-stress situations under control.

The mix of exhausting work plus time away from you has the near future looking pretty fucking bleak.

He knows it's for the best though. He'll see you at night as much as he can, but the more focused he is during the day, the sooner he can wrap up this mess and appreciate dating you the way he wants to.

Better get started then.

Kendall gently pulls the covers back so he can climb out of your bed without waking you up. He retrieves his clothes from the floor of your apartment and gets dressed quickly. He feels his phone in his blazer pocket and pulls it out to find almost 100 emails, dozens of texts, and 9 missed calls. It's not even 7am yet.

He stuffs it back into his pocket and turns to face where you're lying - still fast asleep - in bed. He considers letting you continue to sleep, but that would mean leaving without saying goodbye. For his sake, you'll have to sacrifice some rest.

Kendall crouches beside the bed, his hand reaching up to stroke your head as he leans in and places a kiss on your forehead. He hears you emit a little groan as you come to.

"Hey," he says deeply, his voice still husky from sleep. He tries to speak as softly as he can while you slowly wake up. "I uh, I have to head out," he whispers, his thumb running gently back and forth across one of your cheeks, "but just wanted to say bye."

"What? Noooooo," you groan again, your eyes still closed but your arms reaching out from under the covers to wrap around his neck. He smiles at the gesture. "Please don't go."

Your grip on him is weak but he can feel how much you want to keep him there. It's been so long since someone has express such a genuine desire for his presence.

"I'm sorry sweetheart," he says lowly as he turns his face to kiss the inside of one of your wrists. "Have to get back to mine before the press do."

Fuck, does he ever want to stay though.

He strokes your head again. "I'll try to come back tonight if I can."

You nod, your eyes still closed and arms still wrapped around his neck. "Yeah, you better come back,” you grumble. "I'll come find you if you don't."

Kendall smirks as he leans in to kiss your forehead again. "Yeah, okay tough guy," he scoffs softly.

He crouches there for a moment longer, his thumb brushing across your cheek as he watches you drift back to sleep, your eyelids gently closed and your breathing slow and deep. It takes all the willpower he has to put physical distance between you and him by standing up and leaving your apartment, but he eventually manages to do it.

Reminding himself that he's gonna come back tonight helps.

----------------------

Over the next few days, you almost forget that you're dating Kendall.

Well, that's not totally accurate. He's slept over at yours for three of the past four nights, but he always shows up past midnight after you've already fallen asleep.

You have the same routine - he buzzes into the building, you sleepily prop your apartment door open for him and crawl back into bed, and then he joins you a minute later. The feeling of him climbing into your bed and pulling you into his arms is consistently the highlight of your day. Having him next to you, feeling him wrapped around you, you don't take a second of it for granted, but it doesn't stop you from craving deeper physical intimacy.

Since the night before his press conference, Kendall hasn't initiated sex, and with the amount of stress he's currently under, you don't dare to initiate it yourself. You figure that if he had the energy to fuck you, he would, so you try to remind yourself that he's severely overworked and still choosing to spend almost every night with you.

But it also doesn't help that you're still working out of the Waystar offices. Despite Kendall's very public callout of his father, he is still a Waystar employee/shareholder, and as his assistant, you both still have the right to enter the office. Kendall hasn't taken advantage of that yet, but you have no choice.

His instructions for you are clear - business as usual. There are still meetings to schedule and calls to field and emails that need to be responded to, so aside from the stares and side-eyes you receive when you walk through the office, your day to day is pretty much the same. The only other difference is that Kendall isn't there with you.

You know that it's purely business, that your job doesn't require you to be with him 24/7, but it sucks to not have him around at all. Your work days feel so much more meaningless without him, and having him around every night but without having sex almost makes it worse. It's almost like he's edging you with his presence - depriving you of him all day and then giving you a little taste at night but without the part that you're really craving.

It makes you feel a bit like a desperately horny teenager, but as you stare wistfully into his empty office one day, you decide that enough is enough. Fuck it.

---------------------

Kendall sits in the back of his chauffeured car as he heads home after having lunch with one of the many reporters currently writing a piece on him. He feels his phone buzz in his hand and turns it over to see your name. He opens the message immediately.

"Missed you last night. Almost willing to get on my knees and beg (or do whatever else) if it means I get some extra Kendall time soon.”

Kendall grins at his screen and leans further back in his seat. He feels a rush of excitement course through him as he rereads your not-so-subtle proposition, the image of you on your knees sending a pleasant ache into his groin.

He misses you a lot too, and it sounds like it's in the exact same way.

The self control he's been exhibiting the past few nights could be compared to that of a Buddhist monk. Crawling into your bed and feeling you so warm and soft beside him has been torture when he's trying to be considerate and not make assumptions about what you'd be okay with. You've been dating for less than a week and he really isn't sure what's off limits yet, so waking you up with sex feels like a big jump to make this early in.

Being this cognizant though means that there's been a specific itch that, this week of all weeks, he hasn't been able to scratch.

Kendall doesn't hesitate - he sends a message back to you within a minute of reading yours. Knowing that you want him as badly as he wants you is going to make waiting any longer than a few hours fucking impossible.

“I’d like to see that.
Mine tonight?"

Chapter Text

You punch in the code for Kendall’s apartment and the elevator begins to rise. You're not ashamed to say that you rushed over the second he said he was home - your pride is not worth losing even a minute of the time you get with him tonight. Your heart beats rapidly with every passing floor, but the doors open before you can determine if it's from nerves or pure anticipation.

Clean lines, muted colours, mid-century modern influences, and the biggest windows you've ever seen greet you. You take few steps out of the elevator directly into Kendall's massive living room before stopping short, unwilling to venture further into the apartment without him there.

Your first thought is that the place feels significantly more like the home of a billionaire than Rava's did. You’re momentarily reminded of the floor-to-ceiling windows and greyscale interior of the Waystar offices - it's almost too obvious how present work is in every facet of Kendall's life.

"Ken?" you call out over the low beat of music that seems to be coming from every corner of the room. You can hear the song echoing down the hall to your right, as well as through an entryway on your left that looks like it leads to the kitchen. You notice a staircase in one corner of the room that leads up to a second floor. How fucking big is this place?

"Yo!"

You turn to see Kendall emerge from down the hall.

"Welcome to Casa Ken."

He wears a dark polo shirt, black jeans, and the biggest grin on his face as he approaches you confidently, clearly pleased by your bewildered expression.

"Thought it was about time I hosted you," he smiles as he reaches for you and pulls you in, his lips quickly finding yours.

One trait of Kendall's that you absolutely love is his ability to kiss you in a way that makes the world around you disappear. You're sure it's a skill he's honed from years of being a playboy - a learned ability that comes naturally when frequently kissing beautiful women in dark corners of luxurious rooms. As usual, all thoughts fade to nothing as he deepens the kiss. You feel his palms press into your lower back, pushing you into his body. He moves his hips to meet yours.

You laugh against his mouth; you didn’t expect him to get down to business literally the second you walked in the door.

“Wow, what a welcome,” you say teasingly. “Not even an attempt to woo me with your apartment first?”

Kendall chuckles and looks down at you, eyes crinkled and warm. You resist the urge to press your lips to his again.

“Hey, you said you were nervous to see this place, I thought I was doing you a fuckin’ favour with that distraction,” he jokes, and you can almost feel him itching to touch you more. “But you want the, uh, the grand tour, huh?” He moves his hand to your lower back and walks you toward the apartment’s balcony door, his fingers carefully sliding around your waist. “We can do that.”

“Oh we’re definitely getting back to that favour,” you scoff, and he grins as he pulls the door open, letting you step out into the cool night. “But, you know, if I’m here…”

Your sentence trails off as you approach the balcony railing to take in the magnificent view - buildings towering over every street, clusters of light shining from the thousands of windows spread out in front of you, the dark night sky above it all. You lean against the cold steel barrier to look down, watching little figurine people pass in and out of the spotlights cast by the street lamps below.

It's a suitable perch for someone who could almost be considered a king.

You can feel his eyes on you before you feel his arms reach around your middle from behind. He presses his lips to your temple and you close your eyes, sacrificing the view in order to commit the moment to memory.

You’ve learned in your week of dating Kendall that he very much likes physical touch; he never hesitates to hold you, kiss you, or touch you when he comes to stay the night. But it’s all been in the dark and privacy of your small apartment, always late at night and hidden under your bed covers. You may not be in public right now, but it feels very different to have him claim you here, out in the open.

“Quite a view huh?” he rumbles in your ear. “Think you can see your cute little apartment from here?”
You hear the teasing tone in his voice and gently slap his arm. “You tell me, perv,” you banter. You turn around to face him, his arms still wrapped around you. You give an exaggerated look to your left and then your right. “Did you hide away the telescope you’ve been using to watch me?”

Kendall shrugs, playing along.

“No, just haven’t had the time lately, had to delegate it to Jess this week. I have the notes if you want them?" He says it earnestly, his face totally expressionless until he see’s your look of mock-horror and can’t stop himself from breaking into a smile.

“That’s not funny,” you protest, but the laugh in your voice says otherwise. It’s so nice to be playful with him again.

“It’s fuckin' hilarious,” he chuckles and you feel the vibration of his laugh as he leans in to kiss your cheek. “C’mon.” He turns toward the balcony door, his hand once again finding the small of your back as he guides you inside. “Let me show you the rest.”

He speed-guides you through each lavish room. You see the living room with its top-of-the-line sound system, the kitchen with its multitude of impressive appliances (that you suspect he’s never actually used), and his in-home theatre with the largest screen you’ve ever seen outside of a cinema. It’s not lost on you that the theatre room alone is the size of your entire apartment.

"Jesus Ken, I'm starting to feel really guilty that you had to slum it at mine this week," you joke as he leads you upstairs to the apartment’s second floor. “I’m sorry you had to experience such a housing downgrade.”

You’re taken aback when you hear his suddenly less than lighthearted response. "Yeah… Right,” he scoffs sarcastically. “You should feel really fuckin’ terrible for uh, taking me in like some fuckin’… stray cat every night.“

He plays it off like a joke, but it’s not up to his regular standard of wit and he doesn’t do a good job of hiding the tinge of bitterness in his tone. You hate that he seems to feel embarrassed about needing company during such a stressful time.

You give his hand a squeeze as he leads you down a hallway toward the only room you haven’t seen.
“Well those visits were the highlights of my week," you respond nonchalantly.

The truth comes out naturally, though it feels foreign to be so open about how much you like him. You’re usually more guarded than this in new relationships, but comparing Kendall’s deep-seated fear of vulnerability to yours has made you feel much more confident than you actually are. Next to him, you feel almost well-adjusted.

“Plus, who could resist letting in such a handsome cat,” you add.

In your periphery you see him give a slight shake of his head as he lets out a scoff of amusement, his cheeks shifting into a smile.

Kendall guides you to the doorway of his bedroom, allowing you to enter first. There's not much in here that you haven’t seen in every other room - massive windows, luxurious furniture, expensive TV, etc. etc. Two large paintings (undoubtedly worth millions) hang in the centre of the room directly above his bed, but they feel generic and not at all personal to him or his style.

Nothing in this room, or in the entire apartment really, has come close to conveying the warmth and depth that you see in Kendall. You very suddenly lose complete interest in the house; tour's over, it’s clear now that the only thing of value in here is him.

You stop in the centre of room before turning to face Kendall just in time to watch him shut the door and stride over to you. He’s waited long enough.

"Come here," he husks and hurriedly draws you into him.

Your body is pulled forward as one of his hand finds the small of your back and the other your cheek. He breathes you in like air, inhaling deeply through his nose as he presses his lips firmly to yours. His moves are rushed, desperate to fulfil a desire he’s been deprived of for far too long.

“I need you so fucking bad,” he growls, his mouth moving from yours down to your jawline as his hands grasp to pull you in tighter. You can feel him growing hard against you, his hips searching for the best angle to press into yours. Your lower stomach begins to stir deeply, spreading through your body like a shiver and forcing a breathy moan from your lips.

You don’t notice Kendall’s hands move to the hem of your shirt until you feel it being pulled up and off of you. His arms quickly replace the fabric by wrapping around you, but only for a moment. His hands race to your waistband next, undoing the button and pushing them off your hips. You instinctively step out, waiting to feel him wrap you up with his warmth again, but he doesn’t. He takes a step back instead.

“Fuck…” he says lowly, looking you up and down, taking you in. You can see his length fighting against the seam of his jeans as he admires you, but he doesn’t move take off any of his clothing as he steps toward you again. Instead, he surprises you by knotting his fingers in your hair and gently pulling down so that you're looking directly up at him. He kisses you hard and fast on the mouth before moving down to your neck and collarbone. You feel his tongue escape from his lips a few times as he licks at your skin, causing your fingernails to dig in where you're holding his arms. Your core aches in anticipation.

“I missed you so much,” you breathe as he works his way back up your neck and to your lips, finding that same dominant pressure as he kisses you again. He groans against your mouth as he feels your hand reach to grip him through his jeans.

“Yeah?” he husks, and he releases you for a short moment to reach over his neck and smoothly pull his shirt off. He cups your face and neck to pull you back in. “You missed feeling me? You wanna feel me inside you?” he says deeply against your mouth.

Your stomach does flips. His words send a surge of warmth to your core and you’re sure that your underwear has begun to soak through.

“So fucking bad,” you moan just as Kendall reaches down to feel between your legs. You feel his fingers press against you through the wet fabric, sending another moan to your lips. You vaguely hear him utter a deep “fuck,” but your mind is elsewhere as he pushes your underwear to the side, his middle finger reaching up to slip between your folds. He pumps it in once and draws it out coated in your slick. He doesn’t waste another moment.

Both hands retreat from you to undo his jeans, pushing them off his hips swiftly, his briefs following suit. He removes the last of your clothing as his energy shifts from deep admiration of your body to pure desire.

“Get over here,” he demands, and he guides you to his bed with him, quickly positioning himself on his back and pulling you on top. He watches you in a daze as you adjust yourself on his hips, his length sitting hard against his stomach and your core resting right at the tip. You feel him twitch against you.

It's been less than a week since you last felt each other, but it may as well have been years with the urgency you're feeling now. Neither of you can bear to wait a moment longer.

You reach down to grip him, feeling the hard weight of him in your hand as you line him up at your entrance. You watch Kendall's face as you slowly sink down onto him, hearing a breathy moan leave your own lips. Kendall's eyes close and he emits a guttural groan, the feeling of you slowly wrapping yourself around him bringing both of you the relief you’ve been waiting for.

"Oh fuckkk," he moans, his fingers digging into your hips as he holds you down on his lap, keeping himself buried deep inside you. "God I fucking missed you," he breathes, and he gently pulls your hips forward, moving them ever so slightly across his. The small adjustment alone has him groaning again. He looks at you with lust in his eyes as he continues to guide your hips back and forth.

"Fuck Ken, you feel so good," you moan softly, your movements picking up speed as you chase the pleasure of him hitting that spot inside of you just right.

Kendall's eyes stay locked on your body, one hand trailing across your shoulders, breasts, stomach, as the other keeps a tight grip on your hip, ensuring you keep the steady pace. He throws his head back as you push yourself a little lower onto his lap.

"Jesus Christ, you're gonna make me cum," he pants, but he doesn't make any moves to suggest you should stop. You can feel him instinctively bucking up under you, and he's now tightly gripping your hips with both hands.

Fuck. Already?

You’re flattered that it’s this easy to get him there, but you’ve been building tonight up in your head all week. It’s not supposed to be over this soon and if you continue to let him take the lead, it’s about to be done. He just has to wait a little longer.

You’re gonna have to make him wait.

Your hips stop moving very suddenly, and you feel Kendall protest the pause as his fingers dig further into your skin, still seeking out the release he was so close to achieving. He looks up at you, half puzzled, half dazed.

You smile devilishly. Oh, he’s gonna fucking hate this.

“Not yet,” you breathe as you lean down slowly, gently bringing your lips to his. You pull back the moment you feel his arms reach around you as he attempts to deepen the kiss.

“Not yet?” He repeats huskily, his breath suddenly hitching in his throat as you slide yourself off of him. You hate the sudden feeling of emptiness, but based on the expression on his face, definitely not as much as he does.

You shake your head in response. Kneeling beside him on the bed, you let one of your hands trace up and down his chest, caressing just low enough on his stomach to feel him slightly squirm under your touch.

“I think you’re too used to getting what you want, when you want it,” you begin. You lean forward, hovering over him and bringing your lips to his neck. You leave a line of kisses up to his jaw and then toward his ear, finally stopping to whisper “So I’m gonna make you wait.”

Kendall groans, seemingly half in response to your words and half in physical frustration.

“No,” he reaches for you, his voice husky and desperate. His hands run up and down your arms, across your shoulders, and up to your cheeks. He seems to know that touching you anywhere else will make this even more difficult for him, “C’mon, it’s been so fucking long,” he argues. “Just let me have you.”

You smile at the choice of words. “What’re you talking about?” you tease. “You do have me. And don’t worry, I’ll keep you entertained.”

You move yourself slowly down his body toward his groin and Kendall watches you in anticipation. He sucks in a sharp breath and throws his head back as you grip his hardness, licking a long slow line up to the tip.

“See?” you say as he eagerly settles in, his head quickly snapping back up to watch you and one of his hands rushing to tangle itself in your hair.

Kendall reacts to every second of attention you give his length; your tongue runs up and down the side, around the tip, down to his balls, and he continuously emits a steady stream of curses and short breaths. You feel him getting more and more frustrated with every second that he’s still stiff, and you knowingly make it worse by never taking him fully into your mouth.

“Baby, please,” he groans lowly as you remove your tongue and begin pumping him with your hand. He caresses the side of your head gently and you see pleading in his eyes. He’s clearly never had to sit with his arousal like this before.

“Soon,” you smile, sticking your tongue out again and tapping his length against it.

Kendall’s brows furrow as he watches you, seeing your smile and knowing that you don’t really intend for it to be ‘soon.’ “And what if I don’t wait and just finish myself off?” he challenges.

You shake your head lightly. “You won't. You wouldn’t settle for less when you know you could be getting something better,” you say matter-of-factly. And then you finally take him into your mouth.

The hand caressing the side of your head suddenly knots itself into your hair and Kendall swears deeply, overstimulated as he finally receives some relief from the pure anguish you’ve been putting him through. His other hand instinctively races to your head, momentarily holding you down on him as he makes the most out of the moment of reprieve. He groans when you come up for air, and again when you move to continue taking him fully into your mouth.

“Jesus fuck,” he husks, “don’t stop,” and you’re almost tempted not to.

Feeling Kendall stiff in your mouth and hearing his pleasure audibly spilling out in sounds and swears makes you want to keep going until he’s pushed over the edge. Despite the little game you’re playing with him right now, you want nothing more than for him to feel good because of you. But you also know that the longer you make him wait, the better he’ll feel.

You come to your senses and pull away just as he’s about to finish. You hear him groan in response to the sudden loss of your mouth around him.

“Sorry baby,” you whisper, and you move up to kiss him gently. “Just a little longer.”

Kendall gives a small moan against your lips. “Sweetheart - please,” he begs, the expression on his face almost desperate. “Please let me fuck you, I've been waiting all week to fuck you.”

The pit of your stomach stirs at his words, quickly followed by a rush of heat through your body as Kendall reaches to place his fingers on the bundle of nerves between your legs. You moan in unison as he slides a finger between your folds to feel the slick that’s pooled there, spreading it as he moves back up to your clit.

“God, you’re so fuckin’ ready for me,” he husks as he rubs you gently, and his other hand reaches down to tug at himself. You feel your legs instinctively spread apart as you hover over him, your breathing heavy against his jaw. “C’mon baby,” his baritone voice rumbles in your ear, “c’mon, let me make you cum.”

You feel him reach further underneath you to slide a finger into your hole, pushing it in as far as it can go. Your breath momentarily catches in your throat before quickly morphing into a moan as he curls the finger inside you. He doesn’t hesitate to insert a second finger and start pumping them in and out of you at an increased pace.

“Wouldn’t this feel so much better if it was my cock?” he murmurs, and your answer is clear immediately - you moan again at the suggestion, your body squeezing his fingers as you imagine sinking back down onto his length.

Fuck it.

You’ve kept both of you waiting long enough. At this point, you’re edging yourself just as much as you’re edging Kendall.

Your lips are on Kendall’s in an instant, your mouth moving frantically against his. When you reach down to grip his shaft, he groans in response and his fingers slip out of you so he can reach up to cup your face in both hands. You barely notice the new emptiness with the way he holds you, his hands firm on your cheeks and his lips pressed hard against yours. His length is hard and heavy in your hand, and you feel yourself tense up in anticipation of it filling you again.

“You’re lucky you’re so persuasive,” you breathe as you move to straddle him. Kendall grins in response momentarily, but his smile is cut short when he feels you position him at your entrance and then slide down. His hands had been resting on your thighs, but as you envelop him, you feel them grasp at your skin, his nails digging into your flesh and head thrown back as he moans loudly.

“Fuckkkk, baby,” he growls deeply. He watches your hips roll back and forth across his lap, his hands rubbing up and down your body, but they halt their movement and dig into you again as you start to pick up the pace.

“Oh I’m so fucking close,” he groans as he throws his head back again. “Fuck, keep going,” he pleads, and with your own climax approaching as well, you have no issue fulfilling his request.

But you can’t help yourself; you threaten to edge him one last time.

“How much would you hate me if I stopped right now?” you say breathlessly. The light note of teasing in your voice should be enough to indicate that you don’t actually mean it, but Kendall’s not taking any chances. His head snaps back up to look at you.

“Don’t you fucking dare,” he growls, and you feel his fingers press into your hips, holding you to his lap as he begins to fuck up into you.

He thrusts into you frantically - fast, deep, and at an angle that sends a rush of heat straight to your core. You can feel yourself nearing the edge, a warm heat quickly spreading through your body as he continues to hit that perfect spot inside you over and over again.

You hear his name escape your mouth in a pathetic moan, and suddenly his arms are around you as he pulls you down to his chest, holding you tightly against him while he continues to fill you over and over again. It happens suddenly - your climax washes over you before you even have time to register how close to your peak you’d gotten.
In an instant, you feel that familiar white hot heat rush through your core and spread across your entire body, but the wave holds you under for longer than you’re used to. You’re only vaguely aware of Kendall’s arms wrapped around you and his length still pumping into you as you moan into his neck, your hands gripping the bed sheets beneath him as you ride it out.

The pleasure washes over you and you come back to yourself just as Kendall reaches his climax. He squeezes you in his arms as his entire body tenses up, his length buried into you as deep as he can manage. You feel him twitching inside you rapidly as his moan echoes in the room. It’s clear that his wave of pleasure also keeps him under for an extra moment, and he holds you to his chest even tighter.

You can tell it's fully passed when he loosens his embrace around you with a deep exhale, but instead of taking his time to catch his breath, his lips rush to find yours. He brushes your hair out of your face as he kisses you tenderly, your bodies still pressed together and his length still nestled between your legs.

You both pull back after a moment, his hands moving to your back as he holds you gently against his chest and cradles your head into his neck. You take a deep breath and feel his fingers trace up and down your spine.

“So you know that was fucking cruel, right?” he finally murmurs, and you break into a grin.

“Oh please,” you laugh lightly, slowly pushing yourself off his body to move to the space next to him. “You loved it.”

“… I definitely didn’t hate it,” he concedes reluctantly, and then rolls over to kiss the top of your head before pulling away from you gently. “But no fucking way am I letting it become a regular thing,” he says as he walks to his ensuite bathroom. You watch as he grabs a hand towel and wets it under the tap.

“If only you had any say in the matter,” you mumble vaguely, mostly to yourself, but through the bathroom doorway you can see him scoff and shake his head with a smile. A moment later, he returns with the damp washcloth and gently wipes at your inner thighs. You watch the light concentration on his face as he cleans away the remnants of his arousal mixed with yours, his movements with the towel slow and careful. You’re surprised by the softness of the moment.

He throws the wet towel back into the bathroom where it lands in the middle of the floor, and then reassumes his place next to you. His arm instinctively reaches around you to pull you into his side, and you settle in happily.

“I’m gonna get revenge, you know,” he husks, leaning over to kiss your head. “When you least expect it, I’m gonna do exactly what you just did to me but I’m gonna make it so much fuckin' worse.”

You side-eye him cheekily. “That sounds less like revenge," you counter, "and more like you just really want your turn to watch me beg." He chuckles in response, his arm pulling you closer into him.

“Yeah, that might be part of it too,” he smiles. “But can you blame me? My fuckin' my name wasn't said positively even once this week... and uh, especially not in the nice way you were just saying it." You feel your face flush as he references how you'd just been moaning for him. "Maybe we can work on getting that number back up for me, yeah?” He smiles cheekily down at you.

It's suddenly very clear that he’s been feeling just as much like a horny teenager this week as you have; you jump on the opportunity to ensure that it doesn't happen again.

“Interesting," you muse jokingly. "Well, if we're going all in with our sleepovers and late night visits… I'm open to losing some sleep if it'll help you fill that name quota.” You look up at him with a sweet smile on your face and Kendall gives an entertained laugh.

“Oh yeah? You’re eager to work some overtime, huh?” he teases, and you shrug innocently.

“I’m nothing if not dedicated,” you say earnestly, and you feel him continue to laugh against your cheek.

“Oh, I know,” he chuckles, pressing a kiss to your temple. He holds you for a moment longer before you feel his arms withdraw from around you. “I’m gonna smoke, do you wanna come?” he asks, and you nod in agreement.

Kendall rises from the bed and disappears into his massive walk-in closet. He returns a moment later wearing sweatpants and a t-shirt while holding an extra pair of clothing. He hands them over to you.

“If you want,” he offers casually, and you smile at the gesture. Putting jeans back on is the last thing you want to do right now.

You’re not surprised that the clothing he’s lending to you feels soft and high quality - all of his clothing is. But you give a subtle head shake of disbelief as you step into the sweats and catch sight of the tag: ‘Balenciaga.’

Sometimes he makes it really hard to forget what radically different lives the two of you live.

---------------------

Kendall tries to not watch too intently as you dress in his clothing, but he can’t help it - it feels like a subtle way of branding you as his. If he can’t do it with a picture on twitter or a red carpet walk, at least he can do it like this.

“Those look good on you,” he says offhandedly as he throws his arm around you and leads you out of the room. “You should keep them.”

As he expected, you politely decline - ‘that’s so nice of you but I don’t need your things, I have enough cozy clothes, my closet is too small to fit anything else,’ etc. etc.

“Yeah, but it would be good for me to have some stuff at yours that I can wear,” he suggests lightly and, just as expected again, you agree. You won’t accept the gift if it’s just for you, but if it’s presented as something to help someone else, you’ll do it. Your thoughtfulness is almost too easy to manipulate.

Kendall leads you back downstairs and out to his balcony. He sits down on one of his outdoor chairs, lighting his cigarette as he watches you take in the view again, your body pressed flush into the railing. Your gaze scans over the skyline, down to the street, and then up to the sky. After a moment with your head leaned back, he sees your face light up.

“Oh, look!” you point above you, “you can see Orion!”

Kendall follows the direction of your finger into the sky. He can see some stars here and there, but nothing sticks out to him. “Do you actually know what you’re looking at or are you just making shit up?” he jokes, and you roll your eyes with a smile.

“Yes,” you laugh, standing up. “Hang on."

You walk over to the balcony door and flip the outdoor lights off. The stars begin to shine a little brighter.

You return and take a seat on the balcony couch, your eyes glued the sky. “I haven’t seen the stars in months,” you muse. “You might have one of the few places in New York that can escape the light pollution.”

Kendall takes a drag of his cigarette as he watches you, your attention fixated above. He allows himself to look away from you momentarily in order to follow your gaze, but still no clear shapes jump out at him.

“Well Galileo,” he prompts, flicking ash off his cigarette, “are you gonna show me how to see what you’re seeing?”

Your focus leaves the sky as you turn to look at him, your face breaking into a huge, somewhat skeptical, smile. “Really?” you ask, and you sound almost giddy.

“Fuck yeah,” he responds earnestly, taking one last puff before putting out his cigarette and turning his body to face the stars in the same direction you are. “Teach me how to uh, fucking find land if I ever get lost at sea or something.”

You look upwards again, a laugh in your voice as you respond. “I don’t know exactly how to do that, but I can show you how to find the North Star and a few other constellations.”

The excitement in your tone is clear, and he feels his heart fill with fondness for you. As someone who rarely gets truly excited about things, it’s strange that he can feel your enthusiasm rubbing off on him.

You begin by pointing out Orion’s Belt, and he’s surprised that he never noticed 3 stars in such a clear line before, but he supposes that he never really takes the time to look up at the sky. You move on to the next part of the constellation, patiently showing him where each star is, and he tries to stay focused on the lesson but he can’t help his attention from turning back to you.

Your gaze is practically glued to the stars while you talk, as though the entire sky will disappear if you let it out of your sight for even a second. You feel his eyes on you and glance his way for a millisecond, smiling when you see that he's watching you. Your attention returns to the expanse above, but his doesn't budge.

He can't explain it - something about this moment feels transcendent to him, though it takes a minute to figure out why. It's when his eyes are drawn to your lips that he realizes that the euphoria he's feeling is coming from the way you're speaking to him.

It’s not your tone, your expressions, or the words you’re using. It's the plain and simple fact that you just want to talk to him. There’s no ulterior motive of wanting anything, of trying to come across to him a certain way, or of persuading him to think one way as opposed to another. You’re just telling him about something you enjoy because you want to talk about it, and you want to talk to him about it.

He's internally embarrassed of this feeling almost immediately. Like Jesus fucking Christ, it's so fucked up that casual conversation is what constitutes a magical experience for him these days. But then again, when was the last time he really had a normal conversations with someone?

He tries to remember. College maybe? That was right before the real networking, schmoozing, and ‘one-upmanship’ing began. But even in childhood, he remembers learning what to say to keep his dad happy (or more accurately, not angry), and that his mom’s words always had a second meaning behind them. His life has just been a steady stream of conversations that hold something else beneath the surface. Even just moments before, his push to get you to keep his clothing was pure selfishness that he managed to mask as generosity.

It makes him slightly uncomfortable to sit in the knowledge that his conversations and relationships are all transactional, but it's not like he's only becoming aware of it now. It's just that the extent of it is so much clearer when he’s with you.

His muscles feel relaxed with you, rather than tensed like they are with other people, as if he’s preparing to fend off an enemy attack or verbally pounce on someone if they slip up. He feels accepted and at ease with you, rather than awkward or self conscious or judged. He knows that you like him for who he is, not because you want anything from him. Best of all, he feels light and uninhibited with you - a feeling he usually only gets when he's just had a line of coke.

Fuck his embarrassment - that is magic. You're magic.

You’re now pointing out the North Star, but you can clearly feel his eyes still on you rather than the sky. You turn to look at him.

“What?” you ask innocently, noticing the smile on his face.

He tries to return to a neutral expression but doesn’t succeed. “Nothing,” he looks down and shakes his head, but the smile in his voice gives him away.

“No, what? Tell me,” you press, and it’s clear that you won’t let it go until he gives you an answer.
“Really,” he clears his throat, trying to wipe from the grin from his face, “it’s nothing, just, I was just uh, thinking that this is why I like you.”

He leans forward, forearms resting on his upper thighs as he looks at you, and he genuinely can’t help another smile from forming on his face as he holds your gaze. His ‘type’ has always been women who he’d categorize as ‘hot’ or ‘sexy,’ and he’d definitely put you in both categories, but you’re also a third bonus thing he didn’t realize he’d been missing out on: fucking adorable.

You don’t respond right away, you just watch him skeptically, your eyes narrowing. “Fine, whatever,” you say after a moment, “don’t tell me,” and then you turn away from him to look at the skyline.

Kendall laughs. It’s an open, joyful, easy laugh, one that he feels coming from his belly rather than his throat. He rises out of his chair to join you on the couch, pulling your back into his chest when you refuse to look at him. “Hey, c’mon,” he laughs in your ear. “It’s true, I like listening to you.”

“Sure,” you grumble childishly, and he laughs again. Fucking adorable.

He chuckles as he leans down to kiss your neck and he feels you relax slightly in his arms. “I mean it,” he says against your skin. “I missed talking to you this week.”

This seems to soften you because you bend your head back to look at him. “Me too,” you say earnestly, your hand reaching up to caress his face. “I don’t even get office days with you anymore.”

He wraps you up a little tighter, one of his hands rubbing gently up and down your arm. “I know baby,” he murmurs, feeling guilty that he hasn’t been including you in the team’s out of office meetings. Granted though, he’s had a few blowups this week that he’s extremely grateful you weren’t around to see. “I’m working on it… I might be able to see you earlier tomorrow night?” he offers. He makes a mental note to cancel his drink plans with Stewy.

You lean your head back again to look at him. “Oh no, I have plans tomorrow night,” you say as if it’s the worst news in the world. “One of my friends from my business program just moved to the city and we’re going for dinner.” You pause for a moment, like you’re trying to remember something. “But I thought you also have plans with a friend tomorrow?”

Shit; he’d somehow forgotten that you’re the one who makes his schedule. He pretends like he wasn’t going to bail on Stewy if you’d been free. “Oh fuck, yeah you’re right. Forgot about that.”

“What about Sunday night?” you suggest. “Do you have anything then?”

Kendall scoffs. “Shouldn’t you already know that?” he chuckles.

You tilt your head back to look at him, your expression somehow both sheepish and proud. “Yes, but for the sake of a normal relationship, can we just pretend that I randomly chose a time where you happen to be free?”

Kendall laughs again. “Right,” he agrees with a smile. “Yes, I’m free.”

“Yay,” you say contentedly, and it’s quickly followed by a yawn that you attempt to hide behind a hand.

“Hey, let’s go to bed,” he murmurs gently, “I’m tired too.”

He’s not. If he was alone, he would probably stay up for at least another hour, but crawling into bed with you is an opportunity he’s not going to pass up.

He leads you inside, up the stairs, and back to his room. As you get ready for bed together and he watches you move about the space, he can’t help noticing how natural it all feels, like you bring the entire room together in a way he didn’t know was possible. Like you’re a central piece of the house that he didn’t know had been missing.

You settle under the covers together, your body curled up against his. As he feels you fall asleep beside him, he reflects on this chaos of this last week and how lucky he’s been to have you as an escape almost every night.

If only you had the power to help him escape the days too.

---------------------

You feel sleep overcome you within seconds of laying down. You suppose it could be the pitch black room, the Egyptian cotton sheets, or the lack of street noise that helps to lull you sleep so quickly, but you think the more likely reason is the sense of safety you get feeling Kendall’s arms around you, his chest pressed into your back, and his head curled down to rest against the nape of your neck.

In fact, given that every night this week has been the best sleep of your life, you’re 100% sure that’s the reason.

***

You wake up in a pitch black room. It takes you a moment to piece together that you’re not in your own apartment at midnight, but that you’re in Kendall’s blackout-curtain-covered room and it’s likely morning. You reach out across the bed, feeling around for Kendall, but he’s not there.

You sit up, your vision adjusting slowly to the dark room. There’s no light creeping out from under his ensuite bathroom door. He must be already up.
Wiping the sleep from your eyes, you pad over to his bathroom and flick on the light - it’s blindingly bright when you haven’t had the chance to wake up to any natural light. As you walk to the sink, you notice that the bathmat beside the shower is wet. Somehow you'd completely slept through Kendall getting ready for the day.

Fuck - how late is it?

You rush out of the bathroom to where your phone is laying on one of his bedside tables, turning over to check the time and expecting to see 10am, 11am, possibly even noon, but it’s 8:13am. Your nervous system slows down. Getting used to Kendall’s nonstop schedule is gonna be an adjustment.

Returning to the bathroom, you do what little prep you can - smooth down your hair, splash your face with a bit of water, and use some of Kendall’s mouthwash to rinse out your mouth. Sighing that you can’t do anything more, you dress in your clothing from last night and exit the bedroom, stopping very suddenly as you enter the hallway. You can hear Kendall speaking downstairs - sternly, firmly, aggressively - and your immediate reaction is that someone from Waystar has come over to confront him.

‘Be quiet. Go back to his room. HIDE!’ your brain shouts at you, but you wait to hear who it is first. You don’t even dare to breathe as you stand frozen in the hallway, but when Kendall finishes talking, there’s just dead air. He must be on the phone.

You allow yourself to exhale.

Kendall is standing by the window when you descend the staircase, hands on his hips and AirPods in his ears. He’s dressed casually - trousers and a polo with a cardigan - but the vibe in the room is anything but casual. His brows are furrowed as he gazes into the empty space in front of him, listening intently to whoever is on the other end of the call.

“No, no, you don’t railroad me like this. No, fucking way,” he says harshly, and then looks up when he sees you enter the room. His face softens very momentarily at the sight of you, but returns to its hardened expression as someone speaks into his ears. You head into the kitchen to give him some privacy and hear him aggressively counter “Yeah, well, accountability’s a fucker isn’t it?” as you walk away.

You take a seat at his kitchen island and pull out your phone, opening your work email. You’ve been cc’ed on about a billion messages from people who want to speak with, meet with, interview, or physically harm Kendall. Nothing in your inbox surprises you anymore - this has become the norm over the last week.

“No, do you think I’ll entertain any of this without running it by my team first? Fuck no, no, this doesn’t work for me. So, uh, fuck you, and god bless.” You hear the click of him snapping his AirPods case shut, followed by his steps as they approach the kitchen.

You turn around in your seat just as he enters through the doorway. “Hey,” you say sympathetically, getting to your feet.

He doesn’t respond. He makes his way to you purposefully and you know what’s coming; he pulls you in when he reaches you, one hand cupping your face, the other spread against your lower back, and he kisses you. It’s not a romantic, tender, or sexy kiss - it feels like a kiss born of necessity rather than passion. It’s the kiss of someone that desperately needs to experience a moment of closeness and comfort.

“Good morning,” he murmurs when he pulls away, placing a kiss on your forehead before moving around you to walk to the opposite of the island and grab an iPad off the counter.

“… Is it?” You ask hesitantly, sitting back down as he focuses on the tablet’s screen. Low music begins to play out of invisible speaker a second later. He places the iPad back down and leans down on the counter, running his hands through his hair.

“Yeah no, it’s uh, it’s fine,” he says unconvincingly. “Just, might have to see my Dad today to meet a shareholder so… gonna go strategize with the team at Lisa’s office to figure out the uh… the fucked up optics of that.”

The ever-present elephant in the room - Logan.

Kendall has never explicitly opened up to you about his relationship with his dad, but it’s not hard to put the pieces together. You’ve seen the way Logan operates in the office and how he threw Kendall under the bus at their congressional hearing. You heard what Kendall accused Logan of at his press conference. You remember that one of the very first things you learned about Kendall is that he has a father who “rules with an iron fist.” And most obviously, you see how Kendall acts when his Dad is around, or even just mentioned - a dangerous cocktail of fear, resentment, competitiveness, and idolization.

You’re sure he’ll open up to you about it all eventually, but today is definitely not that day.

For now, all you say is “Fuck Ken, I’m sorry. Is there anything I can do to help?”

He stands up from his position leaning against the counter to come around the island and pull you in for a hug. He exhales deeply before he speaks. “No, thanks sweetheart,” he muses into your hair. “No, enjoy your day and I’ll uh, I might come by yours tonight… if you’re around.” You nod an “mhmm” in response and he murmurs a barely audible “thanks.” After a quiet moment, he places a kiss at the top of your head and checks the time on his phone.

“I should get going,” he says, removing his arms from around you to begin typing a message. “Fikret should be outside for me in a minute, but you can uh, you can stay if you want.” He glances up from his texting briefly to look at you. “You’re welcome to hang out here.”

You try to imagine a world where you’d feel comfortable or relaxed hanging out by yourself in Kendall’s massive, pristine, empty penthouse. Doesn’t seem possible.

“No, that’s okay, thanks,” you respond lightly. “I have some stuff to do before I see my friend later so I should get back home anyway.”

He nods as he stuffs his phone back into his pocket. “Okay baby, just let yourself out whenever,” he says casually. His hand reaches up to gently lift your chin and he leans in to kiss you, his lips tender and affectionate against yours. He lingers momentarily, but not long. “I’ll see you later.” And then he’s gone.

You’re left standing alone in his kitchen, still feeling the imprint of his lips on yours, and wondering when you’ll finally get an uninterrupted morning together.