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The Office x Male Reader Oneshots

Summary:

The intimate misadventures of MC (or Y/N), the attractive HR rep hired in 2009 to replace Toby.

Chapter 1: Jim

Summary:

Aug 2009: MC, a new employee, has a night of drunken oral with Jim.

Chapter Text

     “Shotsss!” Michael Scott cried, holding up a tiny glass before downing the alcoholic beverage inside it in one gulp. I was surprised by how quickly I had acclimated to my new job at Dunder Mifflin; I felt like I already knew everyone so well after only two weeks. Now here I sat at this dark bar, surrounded by my new coworkers. Apparently after-work drinks weren’t too unusual for this place. Having met the people who worked here, I didn’t find it hard to believe that.

     “Hey, hot stuff.” I turned toward the voice that was yelling over the noise of the bar at me. I leaned back to look to my left at Meredith, two seats away from me, who was already on her third beer. “Got any Halloween plans yet?”

     I blinked, my brow furrowing without me noticing. “It’s August.” I chuckled slightly.

     “Never too early. Me, I live for the anticipation. I put a LOT of work into my outfits. Don’t tell anyone but this year—Hobo.”

     “You’re gonna be a hobo?” She nodded. “Well, actually, I have thought of my costume. I’m thinking of being Orin Scrivello this year.”

     “You’ll totally own that costume,” I heard a different, deeper, closer voice say. I looked up at Jim, who I had forgotten was sitting between Meredith and me. I felt a sheepish smile come onto my face.

     “Really?” was all I could get out while looking at his face. I found it a strain to hold in a giggle. I couldn’t hold in the blood rushing to my face, though. I downed another shot, despite hating the taste of alcohol. Maybe being drunk could cover it up. Jim smiled at me and ran a hand through the dark, voluminous hair sitting on my shoulder. He was clearly getting drunk too, much more than I.

     “Yeah. You’ll have to cut this off, though, if you wanna be recognized as him. Or else you’ll be like, dentist-meets-Anne-Rice.” Jim’s words were just slurred enough for one to notice he’d been drinking; his Ss had grown a bit more voiced like Zs and his Ys were long and drawn out. I let out a shy laugh at his remark, the feeling of his hand in my hair giving me goosebumps around my neck. “You’re right about that,” I conceded, fighting the bubbly warmth growing in my chest and rising to my face. I did plan to cut my hair if I was gonna go with that costume idea.

     I felt an uncomfortable warmth rush to my groin as I looked to my left at Jim, my eyes traveling up and down his body, seeing, feeling how close he was to me. Working in the annex, I didn’t see him all that much outside of group meetings or when he went into the break room. Still, my want for him, which had started on my very first day, had only grown; grown to a level so inconceivable that I found it astonishing I could sit still right now. I downed another shot, the nasty tingling of the drink burning in my mouth. I saw that Jim was continuing to drink as well. I wondered if he had a reason for doing so or if it just felt right at this moment, a subconscious whisper telling him to do so.

     I guessed that by now he might be drunk enough to not get mad at me (or even remember the next day) if I… tried my luck, but I still had to be careful. I had to plant the thought in his head if it wasn’t already there, which was a possibility. I placed my hand on his right knee, the khaki fabric keeping our skin from touching. I felt his head turn toward me and I turned my face toward his, smiling friendlily at him. He smiled back at me, his eyes a bit droopy and his face flushed from drinking. Or was it from something else? I didn’t entertain the idea. I squeezed gently, my outer fingers moving a tiiiny bit up his thigh, my thumb pressing in. I looked back up at him. He now smiled at me with teeth. Was I going crazy or was there something to work with here? I downed yet another shot, getting more and more used to the disgusting flavor with each swallow, and Jim put his arm around me. I sat still, the sudden feeling of his warm, muscled arm surrounding me causing a shock to my system. The smile disappeared from my face, but it was not replaced with a face of discomfort or uncertainty or anguish; rather, it was one of wondrous lust. The feeling of realizing what you can have at this very moment if nothing else goes wrong. I felt my pupils growing as I looked at Jim. An air of warm pink color seemed to surround him. I moved my hand up his thigh even more, just up to the more sensitive area, just enough to elicit a reaction. I felt Jim’s breath hitch just the slightest bit, and he looked at me without a smile, his mouth opened a bit the way mine was just a moment prior. My own jocular smile had returned and I got off my stool and crept around the corner to the back of the bar where the darkness lived without light. Only a couple empty tables sat in the area, and the bathroom doors and backdoor stood to my right as I stood, back against the cold, hard, concrete wall.

     I stood there with an anticipatory smile on my face, giggling to myself. I felt another wave of blush crash over my face when I saw Jim come around the corner, following me. I looked up at him; not very much, as he was only a couple inches taller than me. He smiled softly at me. “Hey.” He placed a hand on my shoulder and slowly creeping it down my back and halfway around my waist. I grabbed his face—his whole head, really—in my hands and locked our lips together, if only for a moment. He gently pulled his head away, not even pushing me away. His other hand came to my shoulder, rubbing it as he looked at me with this look in his eyes, like he was fighting his very self.

     “I-I’m engaged.” His voice was soft and weak, as if he didn’t really want to protest. “Maybe I shouldn—“

     “She isn’t here,” I countered weakly, looking up at him with big eyes. They were intense eyes that felt like they held all of the world’s desire in them as I looked into his.

     His own eyes seemed to hold a similar sentiment in them. They traveled all along my figure, so similar to his own. “I—“ I could see him struggle with what he’d started to say.

     “What, Jim? What? Just say it.”

     “I want it.”

     A satisfied smile crept onto my face. “Yeah? What do you want?”

     He swallowed and looked down. “You. Tonight.”

     “Let’s go.”

     “O-Okay.”

     I grabbed a hold of Jim’s loosened tie. “I’ll call a cab.” I let go and took my phone out of my pocket to do so. We sat back at the bar with everyone else (one or two people had left by now without having said goodbye to Jim or me) for a couple minutes as we waited. We took a few more shots each.

     “Well guys,” I announced to my remaining coworkers sitting at the bar, “I’m going home. And taking Jim with me. I’ll take him to his home.” Even while drunk, I still evidently could be a conniving liar. “Goodbye, everybody. See you…” I struggled remembering what day it was. It was Friday. Of course! “Monday,” I finished, holding up an empty shot glass as a salute to everyone. The cab would get here soon. Jim said goodbye to the group and we left through the front door to see the cab when it arrived.

      I stepped out and felt the cool night air nip my skin. I found it so odd that here in the north, they could have nights under 70 degrees even in August. I still wasn’t used to it. I savored the cool temperature, which I’d never been able to experience in the summertime in my hometown.

     I put an arm around Jim and rested my head against his shoulder for a second as we waited. When the cab came a moment later, it beeped and we got into the back.

     As the cab went off, I realized I still had the empty shot glass in my hand that I was holding earlier. I rotated it in my hand, feeling the bumpy diamond-shaped pattern in a ring around the outside. I pocketed it, and Jim and I got out as we reached my apartment.

     I got us inside quickly, hoping to minimize the number of possible eyewitnesses. The second I locked the door behind us I took Jim’s face into my hands and kissed him hard. A cloud seemed to lift from him as he wantonly kissed me back, one arm around my back and the other in my hair. I turned us around and backed him up into the couch, forcing him to sit. I kissed down his face and neck, stopping at his shirt and not bothering to take it off (so he did it himself, which took much longer that it should, even for a drunk person). I sat on my knees in front of him and undid his belt, setting it on the floor. Jim’s excitement poked out through his pants a bit. I felt my own grow hotter and my pants tighter as I undid his fly (feeling him pressing against the bottom of my wrist) and eagerly slid his pants and underwear down, freeing his growing semi. I immediately grasped it in my hand and stroked it, releasing a low moan from behind his shut lips.

     Stroking it a couple more times, I opened my lips up to take it into my mouth. I salivated as I licked the tip and sucked on it, taking his hardness deeper into my face. His cock was leaking precum and shiny with saliva when I took it out of my mouth and looked at it again. It had grown to its full size by now and it looked to be about 6 inches. I stroked it a few times again before licking up the underside and taking it into my mouth again. Jim let out a higher-pitched moan. I kept my hands on his thighs, gently gripping the lax flesh as I bobbed my head, feeling the head of his cock go deeper as I lowered my face and feeling the emptiness take over my mouth again when I brought my head back up. I looked up at him, bobbing my head gently, a little slowly, small drips of saliva making it out of my cheeks and trickling down his length. His half-lidded eyes accompanied his open mouth, which let out more little breathy moans, almost as if he still felt the need to keep this quiet in case we were to be heard, as if he was worried Pam was right on the other side of the wall.

     Suddenly Jim’s cock twitched inside my mouth and his hips cocked and stiffened as his eyes rolled back, his head sinking deep into the cushion. He let out a slutty little moan as cum gradually pumped out of his member and into my mouth. I licked the underside of the tip and half-bobbed my head a couple more times to ride it out and Jim’s moans turned into exhales as he finished cumming, a hand on the back of my head grasping my hair. I removed my mouth from his cock and swallowed without thinking about it, then looked up at him again. I had forgotten how horny blowing him had made me, but now that I realized I still felt that tightness in my pants and warmth in my groin, I really hoped Jim would like to do something about it.

     Jim messily pulled his pants halfway back up and, as if reading my mind, got on his knees on the floor. Now that we were level, he kissed me on the lips again and then lowered his mouth to the crook of my neck, unbuttoning my shirt (of which I’d already taken my tie off earlier) from top to bottom and feeling up my pecs with his hands when he got it open. When Jim detached his mouth from my neck, he looked at me with the face of a small woodland creature and felt up my clothed thigh, next to which my tent had been raging for many minutes. When he laid his eyes on it, he couldn’t keep in a “How big is it?” A film of curious lust cloaked his eyes. He moved his hand laterally to feel my cock through my pants and I got up onto the couch and sat, letting him undo my pants himself and slide them off as well as my underwear, a small thump sounding as they hit the floor due to the shot glass still in the pocket.

     Jim blushed when he saw my erection spring free, almost seven inches long and pushing against the skin of his nose. He pulled his head back a bit. I grinned at him. “Want it?” He grinned back and swallowed cartoonishly. “Yeah.”

     “I’ve never done this before,” he said, looking up at me, his big doe eyes half-lidded but so open. His hand rested at the base of my cock, barely pumping, seemingly without him noticing.

     “No, not in college?” He shook his head.

     “It’s alright. Just do what I say. You wanna do that, baby?” He nodded, “sh- sure,” and his hand crept up my cock, beginning to stroke the length of it.

     “Okay. suck my cock.”

     Jim blushed hard at the blatant order. I swore I heard his breathing hitch for a split second. “Y-yes sir,” and he took it into his mouth; the tip at first. He wrapped his lips around it and, as I had, massaged the underside with his tongue, which produced a louder moan from me than any of his had been. I didn’t care to keep it in, even if there did exist the possible worry of earwitnesses. He started to bob his head, not all the way down (I didn’t expect him to), but a little bit. His saliva started to coat the top half of my length as his hands tightly gripped my inner thighs. He even started to moan a bit on my cock. His eyes rolled up barely into his eyelids and he let out a low moan and I felt the vibration in his mouth. It felt like I grew even harder just from hearing that.

     I decided to take my chances. “You like daddy’s big cock in your mouth?”

     Jim looked up at me and moaned in affirmation. He then took it out to reply, “yes, sir,” as he stroked it before putting it back in his mouth.

     “Jim, how deep can you go, baby?”

     Jim lowered his head as much as he could onto my cock. I marked the lowest he went with my finger. When he took his mouth off, I found he’d taken about half of it.

     I felt in my own drunken train of thought that this side of Jim wasn’t just brought on my alcohol, but rather brought out. The swiftness with which this “new” version of him had appeared made me think. As he continued to suck my cock like a whore I found myself thinking that perhaps (whether he remembers this or not when he wakes up) deep inside Sober Jim lay these desires, possibly unconscious, that Drunk Jim simply accepted with ease as a factual part of himself, a part of himself which could coexist with other seemingly contradictory parts; i.e., he could be engaged and still go home with his coworker and suck his cock because he’s horny and thinks he’s hot. Did Sober Jim think I was hot too? I stopped myself from falling too deep into the mental rabbit hole.

     As Jim’s bobbing and licking became faster and moans more frequent and loud, I felt myself getting close. I found myself moaning his name and grabbing onto his shoulder, focusing on the movement and wet warmth of his mouth and cheeks and tongue surrounding my cock, and finally I felt a wave of relief and bliss as I came, pumping out cum into Jim’s mouth. At first he almost retreated his head, having to get used to the feeling of cum in his mouth. When I finished, he carefully removed his mouth from my cock, a string of saliva stretching and then disappearing between the tip and his lip, and swallowed like I had.

     After resting for a moment I realized I felt very tired. I grabbed Jim’s face, squishing his cheeks. “You. Are. Awesomeee. I love you. Buddy.” I kissed his mouth and lay down on the couch, not bothering to redress. Jim lay down on the carpeted floor, no clothes on except for his pants he’d half-assedly pulled back up (his cock was still out). I laid a thin blanket from the couch onto him.

     When I woke up the next morning, Jim would not remember anything after getting up from the barstool.

Chapter 2: Andy

Summary:

Aug 2011: MC gets Andy.

Chapter Text

     My lip twitched as I misclicked and lost my game of Minesweeper. I had a good streak going today, too. Oh, well , I thought. Guess I’ll get back to actual work. I stretched in my chair, leaning back and seeing Kelly to my right, on a call. I looked back to my computer, seeing what work I can do today. I unbuttoned the top button on my shirt, feeling choked by it. I expected a long couple hours ahead of me. That was until Andy came into the annex, interrupting me.

     Andy had just recently become the manager about a week ago, thanks to Robert California. It was going pretty well. Surprisingly, I trusted Andy as the manager and felt he was doing a good job. A better job than some people who had been recently hired to replace Michael, at least. Andy came into the annex loudly.

     “Hey guys!” He made a “zwoop” kind of sound effect, swooshing his hand and pointing a finger out of the door to the annex. “Tooo the conference room guys! Meeting!” He left, not before making eye contact with both of us, who had turned around upon hearing him enter the room. Kelly finished up her call and I followed her out of the annex to the conference room.

     In the conference room, we all sat down in our usual spots (mostly). I sat in a row in the middle and waited for all the seats to fill and for Andy to start. Once everyone was seated, he started drawing little stick people on the whiteboard.

     “We actually have two topics of discussion today. It’s been recently brought to my attention that…” He paused for dramatic effect. “…if HR has… let’s say… relations with other office employees and doesn’t document it, no one can report them to HR!”

     Oh shit. How does he fucking know? Has someone ratted me out? Have my hoes unionized and gone to Andy, or even worse, corporate? I swear I will kill somebody.

     Andy had drawn one stick figure surrounded by a circle of other stick figures, each with a line connecting them to the middle one. Then he’d drawn a little stick figure in the corner sitting at a desk with another one below them on the phone, apparently calling them. He looked kinda… done. A little annoyed. I hadn’t seen him like this often. This was… a tiiiny bit scary, actually. No worries. I smiled pleasantly at Andy from my seat, hoping to get him in a better mood.

     “Apparently something happened in the Yonkers branch and corporate sent me this memo—“ He produced a piece of paper from his pocket. “—which they probably sent to EVERY branch, telling me to talk to you guys about it. But…” Andy ripped it in half. “I don’t care what consenting adults do outside of the building.” He chuckled, his face bending into a big smile. “To be totally honest, I think corporate getting on our asses about this is kiiinda bull. I bet our handsome devil in HR has had his share of fun, and believe me, I’d never tattletale on him, or any of you.” He pointed at me, then to everyone else. Oh god this is so humiliating. I couldn’t help but shrink down into my chair a bit. Well, at least this didn’t mean that my various… encounters were public knowledge. Yet.

     “The other thing they wanted me to talk about was that apparently, though we’re still the strongest branch, our sales have gone down about 6% since a month ago.” Andy erased the previous drawing and drew a little “chart,” the line (representing sales) steadily going up, then crashing down (which was supposedly the 6%). “Anyone have any idea why?”

     Oscar raised his hand. “Because we haven’t had steady, responsible management since Michael left?”

     Andy pointed at Oscar. “That is exactly it. So now that we DO have a new steady, responsible manager, what can we do to fix our numbers? We don’t wanna get out-sold by Akron, of all people!”

     I raised my hand. “We can maybe try to… sell more paper? Via keeping up with our current clients and potentially acquiring more?”

     “Great contribution, Y/N! You’re allowed to leave the conference now.”

     I sat still for a second and pouted my lip in confusion. “I… don’t have to hear the rest of the conference?”

     “Nope, on account of your contribution to the conversation.”

     “Ooookayyy…” I slowly got up and when I was at the door, I leaned into Andy to whisper to him. “Hey, can I talk to you in your office after this? It’s not work-related.”

     Andy put on a really bad, Vandykean “English” accent and did a little bow with a hand flourish. “Uv cowwwse, moy good suh. Pip-pip!” He slapped me on the arm and I found my skin grow tingly as I felt the touch. I was nervous to admit to myself that around the time he became manager I’d started to find Andy kinda…

     NO. Stop thinking. I did a Jim smile (😐) in response to his attempt at being humorous as I headed to his office. I sat down in the chair across from his in his office and waited for him to come in. A couple minutes later, I saw everyone else return to their desks through Andy’s office window and Andy came in, sitting down in his own chair.

     “Y/N! Sew, just wot can I dew ya fouw?” Andy sat back in his rolly chair, a big, goofy smile on his face. I didn’t even try to identify that accent.

     I blushed, remembering the reason I’d wanted to meet with him in the first place. I thought of chickening out, but thought that since I was already here, I shouldn’t. It had taken me quite some time throughout my life to learn that if I wanted something, I often had to get used to speaking up.

     “Well… Andy, I must warn you, it’s not exactly work-appropriate. And… it’s quite personal. It’s a question. Or a request, I guess.” I felt my face grow with uncomfortable warmth.

     “Shoot.” Andy placed his hands, fingers intertwined, on his desk and looked right at me. I guess this was it.

     “Um… Could… I blow you?”

     Andy’s eyes became suddenly more attentive. His brows raised. His smile became slightly awkward. He just… blinked at me.

     “Wh…What?”

     “I… I just kinda wanna… feel it in my mouth. I don’t even find you that attractive, no offense. I know we’re friends, Andy, and if you don’t want it you can say no. But… I just have this urge. I want to. We’d never have to talk about it ever again. It’ll be a complete secret.” I wanted this pretty badly and I considered this my one chance, so I tried my best to convince him.

     Andy’s smile faltered a little, but didn’t disappear. “Y/N, that’s, like, totally inappropriate. And… I love someone else.”

     “Oh, right. You like Erin still. You wanna get back with her, don’t you?”

     He nodded.

     I leaned in a bit, lowering my voice. “Andy, you and Erin are my OTP. I don’t want to date you. Don’t worry about any of that. But right now, you’re still single. Y’all haven’t gotten back together yet. It’ll just be a one time thing. It’ll feel good.” I subconsciously formed my hands in a ball in front of me in a begging gesture. “No one will find out. This is something that I would just really like to do, Andy. It’d mean a lot to me if you let me. Do you want it?

     Andy looked down and took a moment to think. He blushed and looked nervous when he looked back to me and nodded. “Yeah,” he whispered, barely audible. “Okay. I want it.”

     I couldn’t stop a small smile from crawling onto my face. “Awesome.” I got up from my seat to close the blinds on Andy’s office door and windows. “This is gonna be so hot.”

     “Wait, Y/N,” Andy smiled awkwardly and held his hands out in front of his chest. are we doing this right now?”

     I looked back at him, my hair swooshing. “Yeah. I wanted to do it in here, during work. That’s just… how I’ve been imagining it. I guess I find it hotter. Don’t worry, no one will come in without knocking or anything. Just don’t be too loud. I’ll just get under the desk here. We can lock the door if you want. That might be more suspicious, though.” I walked over to his desk, patting it, and waited for him to scoot out to let me under it.

     “Um… Yeah, go ahead and lock it.” Andy scooted out. I went to the door and slowly turned the lock, hoping employees near Andy’s office wouldn’t hear the click of the metal. I walked back over to behind his desk and got into the space underneath. It was just barely large enough for me to fit in, and I still didn’t have room for my head in there. I looked up at Andy, my head situated right in between his thighs, and felt hot and tingly all of a sudden. The fabric of his khakis lay flush against his thighs and crotch. Especially sitting down, his bulge was already evident. I held my hand out, groping it gently to see if he’d get hard that easily. I licked my lips in preparation. I’d thought about this moment for weeks. I bet it was thick. Heavy. I wanted to feel it in my mouth, meaty and floppy. I began to undo Andy’s belt and fly, slipping his khakis off with a lust-driven speed I beheld the way his cock looked in underwear. It was even more evident. The fabric was thin and tight and his bulge sat protruding, and evident; it looked heavy and girthy. I felt my mouth start to salivate and my cock twitch. My breathing deepened and quickened simultaneously as I stared, a tentative hand stroking the fabric around his flaccid cock. I picked it up, starting to stroke it through the fabric, and felt it get a little hard. I heard Andy’s breathing deepen like mine had, but he was being good at not making noise so far. I slipped his underwear off so I could suck him and I started to stroke him gently. It was already kinda thick soft, but as I stroked him and it grew harder, I felt it thicken in my hand. I opened my lips wide and put Andy’s semi in my mouth, coating it in saliva and moving my tongue all along the bottom.

     “Oh, shit,” Andy moaned pretty loudly. I hoped no one heard that, but I seemed to know that was wishful thinking. I had to open my mouth so wide that I was kind of afraid my jaw would unhinge, but I was sure that was unrealistic. I moaned lowly as I bobbed my head down Andy’s now-fully-hard cock, the tip just reaching my throat when I brought my lips down to the base. He moaned again, quite loudly. Maybe he doesn’t care if anyone hears, I found myself wondering. When I took my head off of his cock to stroke it, I admired its thickness and color as it glistened with my saliva and a bit of precum. It was about average length. That was good; that meant I could fit all of it in my mouth, and I found that hot. I opened up my mouth again, putting the head between my lips and bobbing my head shallowly as I stroked the base, then I took it all the way in my mouth and stroked his balls.

     “Fuck,” Andy moaned softly. I’d never heard something so quiet come from his mouth. I stopped sucking his cock for a moment to suck his balls as I stroked him, feeling my own hard-on through my pants with my other hand. I moaned as I palmed myself through my pants while continuing to suck Andy’s cock, tasting the salty skin and feeling the hard, meaty girth with my tongue as I bobbed my head up, down, up, down, quickening my speed gradually. Andy let out a much louder, sluttier “FUCK” as I sped up.

     I felt my cheeks begin to get sore from stretching to fit something with just shy of a 2-inch diameter, and I retreated my head and closed my mouth to take a break while pumping his slicked meat. I began to roll my hips, grinding my erection into my hand while taking Andy’s back into my mouth and continuing to bob my head at the pace I was at. I looked up at him, his face flushed and begging for release. He looked close; then he told me he was close. He actually whispered .

     “I’m close, don’t stop, god, please~”

     I continued to suck, bobbing my head, my breathing intense, my eyes looking up at him, stroking myself through my pants, lowly moaning, when suddenly I felt Andy bring his calloused hand down onto my head and heard him moan loudly as his cock throbbed, pumping streams of hot, salty cum down my throat. He thrusted his hips up in a rolling motion, holding onto my head as I swallowed ropes of cum that shot out of his cock. I moaned almost whorishly as I felt his cum fill my mouth up, gripping his thigh & rubbing my tent. I would definitely jerk off to this memory later. As I felt Andy’s cock slowly stop throbbing in my mouth, as I felt the last bit of cum pump into my mouth and I swallowed it, I let out a big breath and slowly removed my mouth from his cock, keeping my lips flush with the skin until the tip as it slowly started to return to its softened state.

     “Holy shit, Y/N.” It took a minute or so for Andy to catch his breath and collect himself. Then, he pulled his pants up and sat back down in his chair, checking how red his face was with his phone camera and rubbing some cold water from his water bottle onto his face. I took these few minutes to let my boner die. When I was ready to walk out of the room, I opened the blinds back up before unlocking the door and exiting Andy’s office. I stopped for a second to stand by the door and scan the room just in case. To my horror, practically everyone—Erin, Jim, Oscar, Phyllis, everyone—was staring at the door as I opened it and at me as I came out of it. I looked at all of them. Many people quickly turned their heads back to their desks, as if they thought they were slick. Others, like Erin, just continued to stare unblinkingly. I blinked at them awkwardly. God damn it , I thought, the one thing I didn’t need right now. I couldn’t do much else but just slowly walk back to my desk, feeling everybody’s eyes on me as I walked through the kitchen and into the annex. Still gonna jerk off to that memory later, though.

Chapter 3: Ryan

Summary:

Jan 2010: Ryan asks MC to help him experiment.

Chapter Text

     “Are you winning?” Kelly’s chin rested on my shoulder, watching my computer. I double-clicked to open another section. My hand moved slightly and I clicked on a bomb on accident, ending my last Minesweeper game of the workday. I sighed. “No. I’m not.” I leaned back in my chair to stretch and Kelly went back to her desk, starting to pack her things. I’d noticed that she looked pretty today. What I hadn’t noticed was how close it was to 5:00. The clock on the wall of the annex read 4:55. Upon seeing this, I got up from my desk (turning my computer off) to retrieve a snack from the vending machine before I went home. 

     Standing in front of the vending machine, I felt a presence enter the break room. I looked up at who had walked through the doorway; Ryan. Had he been spying on me from his desk in the closet, waiting to talk to me when I wasn’t in the same room as Kelly? He came up to me; his freaky eyes looked up at me when I turned to him.

     “Hey Y/N!” Ryan slapped me on the arm with a forced-looking smile on his face. I looked at him, my bag of baked Lays in my hand. “Hey Ryan.” Ryan put a hand on my arm, softly gripping it (to keep me from running?).

     “Listen, uh…” Ryan looked a little nervous. “Do you wanna come over to my place? To hang out? I know we aren’t all that close, but…”

     Who could resist that face? I was free tonight. I was pretty much free every night…. He was right, we weren’t very close, but I was certainly willing to make a new friend out of him. What all could possibly go wrong? It’s just hanging out with Ryan. I wanted to get to know people better and leave the house (for reasons other than work) more, anyway.

     “Tonight?”

     He looked stunned. He thought for a second. “Um, yeah, tonight’s great.”

     “Okay. Send me your address. I can come any time. Is around 6 okay? I’ll come at 6.”

     Ryan softly chuckled in a slightly baffled manner. “Yeah. That’s fine. Just let me do that…” He took out his phone from his pocket and texted me his apartment’s address. I smiled and placed a hand on his shoulder. “See you.” 

Just then, before I could walk out of the break room, Ryan pulled on my shoulder a little harshly to pull me into a hug. I wasn’t gonna complain about that. I gently patted his back, feeling how his chest felt against mine, how his back felt against my arms, smelling his hair; it smelled like an old book you’d find in a dusty attic. “You too,” Ryan said into my ear before letting me go. I grinned gently while observing that he was a bit… fidgety. He had a soft blush on his face as he glanced away from me, then back. I then returned to my desk to pick up my things and followed a couple people through the door and out of the office.

 

     When I got home, I changed out of my work clothes and into a more casual and comfortable outfit. To waste a few minutes, I hung out and made some lists. Before leaving, I combed my hair and put on some lotion and deodorant. I felt like putting lotion on was something that fancy people who cared about cleanliness did, so I did it. Then I got into my car and made my way to Ryan’s address. I found the building and walked through the halls for a little while figuring out how the numbering system worked. The walls were cold; concrete. The sounds of my footsteps gently echoing made me low-key feel like I was in Amnesia. It was dark outside by now, and not much less so inside these halls, with their dingy, sparsely-placed lights. Not to worry, though; I finally found Ryan’s apartment. I checked my watch, 5:55 p.m., and knocked four times.

     Ryan answered the door a few seconds later, smelling pretty good, like… a strawberry shortcake candle. I took it in. He looked up at me, a cordial, nervous smile plastered on his face. He was in clean, casual clothes and looked pretty good, like he’d bathed. His skin looked dewy and kinda smooth.

     “Hey! Come in.” He moved aside and I did so.

     “Hey, Ryan. :)” I noticed he still looked a tad fidgety, perhaps nervous. Why around me of all people?

     I stood still, but not stiff, hoping he’d pick up on my energy like a wild animal and feel a little calmer. “What do you wanna do?”

     Ryan took a breath and looked up into my eyes. “Y/N, can I tell you the real reason I invited you over here?” he said in a hushed, hesitant tone.

     I raised my eyebrows in surprise and curiosity. There was a “real” reason? Was there also a fake reason? “Why?”

     He broke eye contact for a second, but forced himself to look back up at me. “I’d…” He inhaled. “…heard tell of your… escapades around the office.”

     Oh god. Someone had either told someone or someone had seen something. Where was this going?

     “…And?” I raised one eyebrow, a corner of my mouth on the same side coming up.

     “And… well, since Kelly dumped me I’ve been thinking a little bit about… exploring my sexuality.”

     A big smile slowly crept onto my face. I looked down at Ryan with a more seductive expression.

     “Oh? And so you chose me?”

     Ryan looked side to side. “Well… you’re probably the hottest guy in the office. I’m the second hottest guy in the office. And you like men, and I know you’ve had experience with that… sort of thing. More than me, at least. So… I figured you wouldn’t be too hard to get.” He let out a slight, dry chuckle at his own logic.

     I put a hand on my hip, my mouth frozen in a big smile. I hoped it’d go away soon so my cheeks didn’t start to hurt. I really was flattered that someone had a problem, thought of me, and decided to let me help them. I found it cute and endearing. I wasn’t sure about “second hottest,” though. More like third. “How very flattering. So… you wanna go ahead and start now?”

     Ryan’s eyes opened a bit more. “Oh! Um… I guess I’m as ready as I can be—“

     I took Ryan’s face into my hands and gave him a kiss on the lips; soft and gentle, so as to not turn him off of me. After a couple seconds I retreated my head and looked at him. The blush on his face had gotten a bit of a deeper red color to it. I was sure the same was true for me; I’d felt some warmth grow in my groin already. I thought he looked pretty cute taken aback and I grinned. I then attached my mouth to the skin on the crook of Ryan’s neck and sucked on it, slightly biting it. He let out a squeak. I ran a hand across his chest and felt the hard muscle under the skin… I definitely could do much worse than Ryan. I felt his heart beating quickly. I wrapped my arms around him loosely, bringing us closer together. I kept my mouth on his neck as I tucked my hands under his shirt, wrapping my fingers around his hips and brushing my thumbs over his hipbones and belly, then bringing my hands up to his ribs and chest. I detached my mouth from his skin in order to remove his shirt, which he let me do. He looked at me, clearly nervous and breathing a little quickly, and I took mine off. I pecked his cheek.

     “Don’t be too nervous.” I ran my hands back down his torso and rested them on his hip bones, pulling them towards mine as I ground my own groin against his. I felt a rush of blood to my crotch as my pants grew a bit tighter. My face was buried in the crook of Ryan’s neck as I gently touched him, my hands skimming his back, waist, hips, thighs.

     “I-I’ll try,” he whispered breathlessly. His arms were around me; his hips were grinding against mine, copying my rhythm with no effort or intent. I felt my growing hardness push against Ryan’s, blocked by my jeans and his pajama pants. I ground against him slower, more purposefully, and he let out a little moan. Fuck sex; I could just do this all day. But I couldn’t. I reached a hand down between our crotches and felt up Ryan’s quickly stiffening semi.

     “I think we know now,” I whispered into his ear. I then pushed myself away from him, just a little, so we weren’t holding each other anymore. My brain felt tingly and hot.

     “Where’s your room?” I asked. He looked down the hall. There were a couple doors: two open, one closed.

     “The last one.” His voice didn’t sound full.

     I saw the last door, an open one, down the hall. I gently pushed Ryan down the hall and hurried into his room with him. He had a full-sized bed and some random other furnishings and décor around the room. It didn’t look as disheveled as I’d expected; I’d half-expected him to not even have a bed frame.

     I took Ryan into my arms and I laid him down onto the bed on his back, caressing and kissing down his chest and belly until I got to the waistband of his pants and smoothly pulled them down with his underwear. My breathing was quickening now as his erection was uncovered. It was about five and a half inches long and I began to stroke it at a careful speed. Ryan moaned softly and began to gently thrust into my hand. He muttered a “yeah” and other similar things before I licked it all the way up the shaft and took it into my mouth, sucking my cheeks in and beginning to bob my head. He moaned louder, his hands getting in my hair and holding my head as he thrust a little faster, but not very deep (good thing). I moaned a little, lowly, as I closed my eyes and focused on the feeling of him in my mouth, focused on what I was doing. I placed a hand on Ryan’s thigh and sped up my bobbing (this caused him to moan significantly louder) and then stopped, removing his cock from my mouth and looking at it, covered in my spit. I stood up, aware of how hard I was and that I must have had an obvious tent in my pants. I looked down, about to unbutton them; yep, it was true. To be totally honest, it was less of a tent and more of a… flush outline. I groped myself as I undid my pants, showing it off to him. I pushed them off, keeping my underwear on. Ryan looked over at it, his mouth open, his breath hitching, his face flushing. His hand crept down to his own cock and stroked it slowly, his eyes still glued to the seven-inch-long, cylindrical bulge in my underwear.

     “You wanna suck it, baby?” I asked in a hushed tone.

     Ryan looked as if a drop of drool was about to drip down his lip. He looked like a fox eyeing a big, juicy steak. He looked up at my eyes. “Yes.”

     Ryan got off the bed and I got on, lying on my back. Ryan got back on, lying on his belly, his head positioned between my thighs. I looked at him, grinning expectantly, letting him choose when to rip the band-aid off.

     He looked up at me, his cheeks reddened intensely, his eyelids fluttering, and gently grabbed onto the waistband of my underwear, beholding and carefully anticipating the release of the bulge underneath it. He very slowly pulled the waistband down, my erection finally springing out once he got low enough. He pulled them down further and I pulled a leg through, shaking them onto the floor. Ryan beheld my dong, as long as his face was, and, never having touched another man’s private area before, wrapped a tentative hand around my shaft. He gave it a couple slow strokes before licking the head painfully slowly and beginning to suck on the first couple inches. He slowly and jerkily bobbed his head down and up. His hands crept onto my thighs, resting on them, gently gripping them as he got more used to sucking my cock and got more comfortable and smooth in his movements. His hips began to thrust into the mattress under him, begging it for some friction. I moaned loudly as Ryan’s tongue pushed against the bottom of my member. I buried my fingers in his hair, my hand riding his head down and up as he continued to blow me. I looked down at his face, remarking the shape his lips made around my girth and how shiny and slick my cock looked whenever Ryan retreated his head, only to bring it back down again. I didn’t wanna get too close from him doing this. I needed it.

     I gently pushed Ryan’s head off my head. “Turn over, baby.” I got out of the way so he could flip over as he was told, which he did, of course. He knew what was coming by now. I positioned myself between his thighs. I crouched down and held his pelvis up, his thighs surrounding my head, his balls just over my nose, and spit into my fingers, slathering it onto his entrance. I put one saliva-slicked finger into him to make sure it wouldn’t be too bad. He winced, then moaned a little when I pumped my finger in and out of him a few times. He was wet inside. I put another finger in carefully. Ryan groaned, which again turned into a moan shortly thereafter. “Do it, Y/N. Put it in.”

     I put his bottom half back down onto the mattress and spit into my fingers again, rubbing it onto my cock and his hole before lining myself up with his entrance and slowly pushing in. Ryan yelled, and I stopped once the head was inside of him. His breathing was fast and he looked up to the ceiling as it gradually calmed. “Okay. Go ahead,” he said, still looking at the ceiling.

     I slooowly pushed my pelvis toward his, my hard, wet cock sliding into him, filling him up. He didn’t quite moan, or groan, or yell; it was like a mix of all three, continued until I was all the way in, seven inches of meat filling him up. I rested once I was all the way in, settling and gauging his reaction. I kissed his cheek and jaw.

     “Fuck me.” And I grabbed his hips and ground my own into them, Ryan matching the motions, like ruthless, crashing waves in the middle of the Caribbean during a thunderstorm. I fucked him, alright. I held him to me tightly, grinding into him, breathily moaning into his ear, and then began to repeatedly pull out and slam back into him. That he seemed to really like. He screamed, moaning into the stale, lukewarm air around us, as I pounded him, pulling almost all the way out and then slamming back into him time and time again. I moved his hips up and almost fell onto him as I thrusted into him at a slightly different angle. This seemed to do it. He reached down and started to stroke himself quickly while begging me to keep doing that, all while high-pitched moaning. It turned to a lower pitch as I continued to thrust in and out of him, slowing down and speeding up, which didn’t seem to make much of a difference. He continued to stroke himself at the same pace as I changed mine; all he told me to do was keep going and cum in him. What a whore, I thought.

     I steadied my pace, choosing to go fast, and grabbed Ryan’s cock out of his hand, stroking it for him. My breathing was shallow and fast and if it hadn’t been so cold outside I’d’ve definitely been sweating by now. Ryan begged me not to stop (with some expletives thrown in there) and I didn’t until shortly after he jizzed all over my hand; as the cum came out of him in pulpy streams, I felt my hips tense up and thrust into him the last few times before my cock throbbed in orgasm, pumping pools of cum in the fleshy crevice of his insides. I moaned loudly (possibly with some expletives as well) and thrusted into him a few more times as I rode out my orgasm, intensely feeling every pump into him until I finally felt no more of that hot, orgasmic electric current pulsing through my groin. I sighed as I removed myself from him and fell back onto the bed right next to him, breathing heavily. I flipped over into my side, facing him.

     “You confused about your sexuality now?

     Ryan stared up at the ceiling, into space. A small smile crept onto his mouth. “No.”

     I closed my eyes, not thinking I was tired enough yet for a nap. “Good.”

 

     I woke up early the next morning. Damn, I guess I went to sleep after all. Ryan was sitting up in the bed beside me. The light of dawn was just about creeping into the windows from behind the horizon. He blew out smoke from his mouth.

     “I didn’t know you smoked.” My voice was gritty from having just awoken.

     Ryan looked to me, his naked bottom half only covered by the sheet, and looked at the cigarette in his hand. “I wanna stop. Soon.” He took another drag. “It’s better than coke, at least.”

     I remembered what day it was. Wednesday. I made a mental note that we’d have to work today and before I got ready I’d have to go back to my place. I didn’t have to do that just yet, though, I sat up, put an arm around Ryan and put my nose in his hair. It smelled of unwashed pillowcase and vanilla.