Chapter 1: Index
Notes:
Prompt list here: https://www. /kinktober-2025/787065908197818368/more-information?source=share
Chapter Text
Day 1: Masturbation, Orgasm Control, Incest (Sam x Dean)
Day 2: Coming untouched (Sam x Dean)
Day 3: Threesome (Sam x Dean x Adam)
Day 4: Voyeurism (Implied Wincest - Dean & Sam/Female Character)
Day 5: Dacryphilia (Sam x Demon!Dean)
Day 6: Outdoor Sex (& Humiliation) - (Sam x Lucifer)
Day 7: Chastity (Sam x Dean)
Day 8: Cages (Lucifer x Michael)
Day 9: Shibari (Richchesters)
Day 10: Oral Sex (Sam x Dean)
Day 11: Somnophilia (Sam x MoC!Dean)
Day 12: Kneeling (Jared x Jensen)
Day 13: Medical Play (Sam x Dean)
Day 14: Omegaverse (& Posessive Sex) - (Omega!Jared x Alpha!Jensen)
Preview:
Day 15: Sex Pollen (Sam x Dean)
Day 16: Remote Control (Sam Wesson x Dean Smith)
Day 17: Service Kink (& Messy Sex) - (Sam x Dean)
Day 18: Genital Torture (Sam & Terrance Clegg)
Day 19: Creampie - Sensory Deprivation (Sam x Dean)
Day 20: Mirror Sex (Sam x Dean)
Day 21: Rimming - Monsterfucking (Sam x Werewolf!Dean)
Day 22: Quiet Sex (Sam x Dean)
Chapter 2: Day 1: Masturbation – Orgasm Control – Incest (Sam x Dean)
Summary:
Day 1: Masturbation – Orgasm Control – Incest (Sam x Dean)
Chapter Text
“Stop, Sammy,” Dean ordered, voice firm.
“Please, Dean,” Sam whimpered, hand letting go obediently though so as to not finish himself off even if he was so, oh so, close to his orgasm.
“Oh no, Sammy, you promised to do whatever I want you to do,” Dean reminded him and yes, Sam had, though now he regretted taking on that bet.
Dean was sitting on the other bed, leaning back against the headboard, stroking his own hard dick lazily as he watched. He had not touched his little brother once that evening and yet he had him right where he wanted him, frustrated and on the edge and following Dean’s orders.
“Twice more, Sam, c’mon,” Dean instructed him, nodding towards Sam’s dick.
“No, Dean, c’mon,” Sam whined, stubbornly leaving his hand on his thigh.
“You didn’t have to agree to that bet but you did, but if you wanna be a sore looser I’m sure I can come up with something else for you to do or maybe I could finally put those clippers to good use,” Dean offered, an innocent smile on his face as he gestured to Sam’s hair.
Sam’s scowl deepened and he grumbled a “fine” before he grabbed his dick again that hadn’t flagged a bit. He continued stroking himself, biting his lip to stifle his noises.
Dean let him do it for a moment longer before he spoke up again. “Do it right, Sammy,” he said, demonstrating on his own dick as he swiped his thumb over the sensitive head, collecting the pre-come there.
His brother actually followed suit for once, eyes squeezing shut and a moan escaping as he mimicked Dean’s movement, his thumb rubbing across the leaking crown of his dick again and again.
“Fuck,” Sam yelled a second later, one hand moving to clamp down on the base of his dick while the other gripped his own thigh tightly, nails digging into the flesh.
“Don’t cum, Sammy,” Dean reminded him, letting his own dick go, the sight of Sam pushing him closer to his own orgasm than he liked.
Sam’s breathing was heavy, labored and maybe even with a sob in there too if Dean listened closely.
Dean let his brother come away from the edge for a few moments and this time he didn’t need to say more than his brother’s name for him to start again.
“Good boy, “ Dean told him and he could see the shiver run through his brother’s body at the comment.
Sam had to stop himself even quicker this time and Dean almost wanted to take the cruel joy in making Sam do it more often than that but Sammy’s flushed and desperate face was enough to make him cave.
“Alright, Sammy, you earned it,” Dean said, his own hand still against his throbbing dick, wanting to focus on his brother. “Cum for me, Sam, c’mon.”
A few strokes was all it took for Sam to cry out, hand flying over his dick as he came and came. Sam’s hips were bucking up as he fucked his own fist, white ropes of cum covering his hand and stomach.
“That’s my boy,” Dean mumbled, watching Sam closely, beginning to stroke himself again too.
To no one’s surprise Dean came quickly too, milking himself to the sounds of Sam’s labored whines as the overstimulation set in.
Chapter 3: Day 2: Coming untouched (Sam x Dean)
Summary:
Day 2: Coming untouched (Sam x Dean)
Chapter Text
“Dean,” Sam whined when his brother bound first his right and then his left hand to the bed posts.
The cabins they sometimes stayed at often lacked the amenities of a proper motel but they did offer other advantages like privacy and sometimes beds with sturdy bed posts.
“You can do it, Sam,” Dean said, tying the knot off and grinning wickedly at Sam.
“Please,” Sam pleaded.
“Nah, Sam. You don’t need it, you’ll see.”
Sam had been able to do it once before, cum on Dean’s cock without a hand on himself and apparently Dean was determined to make him do it again. And to stop Sam from sabotaging Dean’s plans his brother tied his hands to the bed so there was no way Sam could reach his own dick.
There was a lot of foreplay and teasing and by the time Dean finally pushed his dick inside Sam, his wrists were beginning to hurt from the way he kept pulling at the ties.
He had been thoroughly fingered, his prostate abused by Dean’s fingers and maybe, just maybe with the way sparks of please had zipped up his spine he’d be able to cum like this if Dean could just repeat what he had done with his fingers with his cock.
Sam wrapped his legs around Dean’s waist, canting his hips up and chasing the pleasure whenever Dean hit the spot just right. The rhythm was just right, Sam moaning and groaning while Dean was breathing heavily over him, taking care not to touch him in any other way.
“Cum for me, Sam,” Dean said after a few minutes though Sam had to refuse.
“Can’t, Dean. Not enough,” Sam pleaded.
Dean rolled his eyes and Sam was about to tell him off for it when two fingers meanly tweaked his right nipple, Sam’s voice cut off by a stuttered and slightly pained groan. It wasn’t just pain though and Sam groaned in pleasure when Dean tweaked the other one, less meanly though.
“Sam,” Dean said again, the order still standing without him having to repeat it.
“Just a little more,” Sam moaned, arching under Dean’s exploring fingers.
Dean lifted Sam’s legs over even more, almost bending him in half, the angle of his hips making his cock pass right by Sam’s prostrate on every thrust inside.
Sam’s “almost” got lost under the sea of sounds, whines and moans he made when Dean somehow still managed to bite and nip and suck at the nipple that was not getting assaulted by fingers.
The hot wet pinchy feeling was enough to send Sam over the edge, his dick spurting cum between their bodies. It felt so intense, more intense than usual and yet Sam missed a firm grip around his dick, the way milking himself to the last drop felt so good.
But this was good too, really good and judging by the look on Dena’s face they would have to do it again soon.
“Knew you could do it,” Dean praised him. “Knew you could cum on just my cock,” all smug and self-satisfied and Sam was too blissed out to say anything, even less, do something about.
Chapter 4: Day 3: Threesome (Sam x Dean x Adam)
Summary:
Day 3: Threesome (Sam x Dean x Adam)
Chapter Text
“Are- are you sure?” Adam asked, uncertainty clear in his tone.
“Yes, Adam, he likes it, needs it in fact,” Dean assured him, a confident smile thrown his way.
God this was fucked up, wasn’t it. But then again so was being resurrected and a whole load of other stuff he didn’t want to think about. Even more fucked up was the fact that he was jealous of Dean for the end of the deal he got.
“I’m the oldest” He had told Adam when he had asked and the look on his face didn’t allow for any discussion about it.
“Okay,” Adam mumbled, gripping the base of his dick before he thrust forward a little.
Sam’s lips were soft and the inside of his older brother’s mouth hot and wet. Adam couldn’t hold back a groan at the way the head of his dick was enveloped in that soft heat, Sam’s tongue lapping at the sensitive crown.
“Fuck,” he moan, hips stuttering forward.
“Told you, it’d be good,” Dean said, smugly, his own hips working hard and pushing Sam's body forward on the bed and right onto Adam’s dick.
Sam in the meanwhile was making small mewling and whining sounds around Adam’s cock before he choked a little when it hit the back of his throat too fast.
“Don’t pull out,” Dean immediately said, staring Adam down. “He can take it.”
Adam wasn’t so sure, especially not when he saw tears gathering in Sam’s eyes but he did as Dean commanded. Instead, he pushed in deeper, his balls hitting Sam’s face now too as he sunk all the way inside and into his older brother’s throat.
“He loves taking care of his brothers,” Dean spoke up again, voice strained from his own pleasure.
One of Dean’s hands was gripping Sam’s hip tight, pulling the big body along with every stroke while the other one had wandered all over Sam at first, pinching at a nipple and now teasing Sam’s own dick that was laying rock hard and nearly purple on his stomach, a pool of pre-cum collected under his belly bottom.
Sam did indeed look like he enjoyed it, dick twitching and hard, noises whiny but not pained and the blissful expression on his face was enough for Adam’s hips to jerk again.
God this was so fucking fucked up.
It was however not fucked up enough to stop him from thursting deep into Sam’s mouth, pulling out and smearing his cock along Sam’s lips before plunging back in again. Heat was gathering in his lower belly and Adam knew he would be coming soon.
“He swallows,” Dean said, evidently having noticed just how close Adam was getting to his orgasm.
“Fuck,” Adam groaned, pushing all the way balls deep back inside as he unloaded in his brother’s mouth, Sam’s throat working around him as he swallowed what Adam was giving him.
The wet tongue felt overwhelming on his softening dick as he pulled out and he breathed harshly, leaning against the wall behind him as he caught his breath.
He looked down at Sam, legs wrapped around Dean’s waist, being pushed and pulled roughly along the bed as the oldest brother was fucking into him. Sam smiled at Adam, upside down and with tears and spit over his face, some of Adam’s cum collected in the corners of his mouth.
“Thank you,” Sam said hoarsely and Adam wasn’t quite sure if he came back from the dead right or not but maybe it didn’t matter either.
Chapter 5: Day 4: Voyeurism (Implied wincest - Dean & Sam/Female Character)
Summary:
Day 4: Voyeurism (Implied wincest - Dean & Sam/Female Character)
Chapter Text
Dean knew he should feel much more shame about it than he actually did - which okay, would be any shame at all but the sweet sounds of his baby brother’s moans were just too tempting.
He had a perfect view through the doorway, hidden in the darkness and the wardrobe in the hallway. His pants had been too tight since the moment he had realized Sam and the girl from the case, whose name Dean hadn’t gotten right once, had not noticed him coming back. They were too busy on the living room couch in the house they were squatting in to apparently hear the front door.
Dean peaked around the corner, groping himself through his jeans as he saw Sam’s muscled but lean back flexing as he dipped down to kiss the girl. He could just see the top of his little brother’s naked ass, the curve and the shape alluding to quite the tight, perfect thing Dean would love to get his teeth into.
That wasn’t going to happen anytime soon though so Dean did the next best thing, the closest he would get to sex with Sam.
Dean leaned against the wardrobe, hands fumbling to open his belt and jeans. As soon as he managed to do it, he shoved his right hand into his boxers, a tight grip around his thick erection. He bit down on his bottom lip to stifle his moans and groans as he stroked himself - he had a private concert to listen to after all.
Sam’s moans were interspursed by ones just slightly higher pitched and just by the rhythm Dean could tell his little brother was fucking her oh so sweetly. He peaked around the corner again and visually confirmed what he had heard, her legs were wrapped around Sam’s waist, heels slightly blocking Dean’s view of Sam’s ass as he worked his way in and out of her, muscles flexing.
Dean tried hard to keep himself quiet as he worked himself over, Sam’s ass and his moans and groans in his ear. Oh what would he give to be the one to make Sammy moan like that, he could probably make him mewl even sweeter, take over the work, let Sam just enjoy being fucked open just like he was doing to the girl on the couch.
Pre-come was slicking the way and a particularly loud groan from Sam almost made him blow right then already but the girl's cry of his brother’s name stopped that quickly, anger boiling up at the knowledge that she got to have his Sam like that and not him.
“Wait, shit, fuck,” Sam moaned and Dean saw as his hips jerked even more and goddamnit, now he knew what Sammy sounded like when he came as an adult.
Dean’s hand was flying over his dick now, his grip tight as he tried to follow his baby brother into bliss. He bit into his left jacket sleeve to silent himself as he spilled all over his own fist and into his boxers.
His breathing was harsh when he finally let go of his sleeve and looking back into the living room he saw Sam still hovering over the girl, heads pushed together, presumably kissing. He stayed looking just long enough to see Sam pull out, sadly not catching a glimpse as he disposed of the condom but the perfect view at Sam’s back and ass to fuel at least the next three times Dean would jerk off.
Quietly he took his hand out of his boxers before silently making his way down the other way of the hallway and towards the actual guest bedroom where he would need to try and sleep and not just think about how badly he wanted to fuck his Sammy.
Chapter 6: Day 5: Dacryphilia (Sam x Demon!Dean)
Summary:
Day 5: Dacryphilia (Sam x Demon!Dean)
Notes:
Never written demon!dean or dacryphilia so be warned
(See the end of the chapter for more notes.)
Chapter Text
“Don’t be like that, Sammy,” the demon, not Dean, never Dean, said.
Sam tried to relax, he did, he really did but it was more than difficult with the way he had been manhandled so far.
He also knew that he should be afraid, terrified about what the demon would and could do to him but all he could think about was how he could get Dean back. There had to be a way to reverse the way his brother’s soul had turned black, nothing in their lives had been final, not even death.
Getting close to Dean was the first step and what easier way than to offer himself up to the demon.
The slick, nearly purple head of Dean’s cock was shoved into his face again and this time he obediently opened his mouth. The hand against the back of his head immediately forced his face towards Dean’s crotch, the dick in his mouth shoved past his tongue and down his throat. He gagged, trying his best to stop choking when the demon didn’t let up or pull back.
The hard fucking into his mouth that followed might have allowed him to breathe kinda every once in a while but it didn’t stop tears from gathering in his eyes at the way his soft palate was abused.
Dean cupped Sam’s cheek with his hand, his thumb running along his cheek in a mockingly sweet way before it pressed closer to his eye, making the gathered tears fall down his cheek.
“Don’t cry, Sammy, we’re gonna get to the good part really soon,” Dean crowed, his thumb still smearing the wetness along Sam’s skin as his dick was pushed deep into Sam’s throat again and again.
More tears gathered and Sam wasn’t so sure if it was because of the choking or because of something else but the glint in the demon’s eyes told him that it didn’t matter anyway.
Sam had expected to be turned onto his front, ass up when they finally got to the next part but no. He was on his back, his knees basically by his ears, Dean’s hands pressing them further back as he fucked deep inside an underprepared hole.
The strain in his leg muscles at least somewhat kept his mind off of the way his hole was being split apart.
“Isn’t this better than fighting?” Dean asked, a smile on his face Sam had never seen before. “Think we should keep you like this. My pretty slut to fuck. Boyking? More like boywhore.”
Sam felt shame where he should be feeling anger or dread and he turned his head away from Dean.
“You’d like that, wouldn’t you? Chased me down for months just to get this, right?” the demon asked again, voice mean and mocking.
“No,” Sam tried to reply but his voice was rough and barely understandable after the forced throat fuck earlier.
“Don’t deny it,” Dean said with more conviction, grabbing his chin and turning his face back.
A chuckle and another swipe over his cheek, spreading the new wetness over it. Another swipe and a suck as Dean licked the tears off his own fingers.
The demon’s thrusts got rougher and quicker, eyes focused on where Dean was trying to force away his tears.
“I’d say so sweet for me, but it’s rather salty for my taste,” Dean commented though Sam did not get the feeling that it was deterring him, it more felt like it was spurring him on.
Sam was shoved up the bed again as the demon kept fucking into him again and again and again.
Notes:
I know there's no orgasm here but these are just ficlets after all
Chapter 7: Day 6: Outdoor Sex (& Humiliation) - (Sam x Lucifer)
Summary:
Day 6: Outdoor Sex (& Humiliation) - (Sam x Lucifer)
Notes:
(See the end of the chapter for notes.)
Chapter Text
The last thing Sam remembered was the rushing in his ears and the pain of his throat being ripped out. He hadn’t dared to think about where he would end up after this death but it certainly hadn’t been back here, in the tunnels, alive again. The dread in his gut felt like hell and the devil was there to boot.
“Sammy, Sammy,” Lucifer drawled as he stepped closer, making Sam scramble back on the dirt floor. “So good to see you again.”
“Don’t,” Sam choked out, trying to get his feet under him again.
“Oh don’t be like that, Samuel.”
The fake sweetness in Lucifer’s voice made a shiver run down Sam’s back that only spurred him on. He successfully twisted around and half ran, half crawled out of the cave, the weird half light of the apocalypse world greeted him.
“De-” Sam tried to yell but was interrupted by a swift kick to his back.
“While I would love to show your brother what a good time we’re gonna have, I don’t really wanna deal with him interrupting us,” Lucifer snarled, pushing Sam further into the dry earth.
“No,” Sam gasped again, staring up at the archangel, frozen to the spot.
Lucifer chuckled, awful grin spread wide as he peered down at Sam. “Oh but it used to be so good, Sammy.”
Sam kicked out but was swiftly flipped, leverage gone as Lucifer bound his hands behind his back with the tie on that glow stick necklace he was wearing.
“I’d tell you what I’m gonna do but there’s no real reason to, is there? Not our first rodeo, right?” Lucifer joked and dread filled Sam, knowing exactly what was going to happen.
“It has been way too fucking long.” Sam heard just before his jeans were painfully pulled over his hipbones, Lucifer not bothering to undo his pants.
Hands that were too warm and too cold at the same time spread Sam’s ass apart like they had done hundreds and thousands of times and a sob escaped his throat even though it felt too tight to let any sound out. “No, please.”
“Still so pink and tight for me,” Lucifer praised him, one finger breaching him already and for some reason Sam mind stopped to think about how dirty and grimy Lucifer’s hands must be.
“Not for you,” Sam ground out but it was muffled by the way he was laying on the ground.
Lucifer didn’t bother with preparing Sam, not that he had expected it, but the glob of spit before the familiar cock breached him was not enough to keep the pain at bay. Sam breathed in as deeply as he could, physical pain always easier to deal with than any other kind.
The numbness he had waited on didn’t come though, his hole feeling like it was ripped apart as Lucifer roughly trusted inside him, the heavy weight pressing him down onto the dirt. Sam could see dead trees and mountains in his limited vision, a clear reminder that this was the apocalypse world and not their own, that there were even worse things at stake.
“So tight for me, really been needing a good stretching, didn’t you?” Lucifer asked, one hand gripping Sam’s hair.
“No,” Sam ground out.
“Don’t worry, we’ll get you loose again in no time. Just like how you used to be for me. You were such a slut for me, Sammy, don’t deny it.”
Sam let his head hang as much as possible at the implied threat, the reminder of his time in the cage too much to bear.
He couldn’t tell you afterwards how long it had lasted, only that the parts of his body that had touched the ground were rubbed raw, his hole and ass had been sore and painful and bloody, the light was still half-dim but he had survived, had gotten back up again.
Notes:
And now we know why Sam limped into camp during S13E21...
Chapter 8: Day 7: Chastity (Sam x Dean)
Summary:
Day 7: Chastity (Sam x Dean)
Chapter Text
This was a little extreme, even for Dean but he really saw no other way. He had to keep Sam from Ruby and if that meant having Sam in his view near constantly then that was what he would do. And after Sam had escaped the panic room once already Dean was not about to risk it again. Sam would just have to stay close and be monitored, no sneaking out for booty calls or anything else.
And maybe Dean had gone to quite the extreme to ensure Sam stayed away from his booty calls, but that was just what this situation called for.
Sam was pissy and short with him and Dean knew exactly why but it didn't make him cave. His brother could suffer through a few weeks of blue balls if it meant no more demon blood and no more consorting with hell bitches.
“Dean,” Sam began, pacing through the motel room.
Just by the tone of his voice Dean already knew that Sam wanted to argue with him about it again.
“No, Sam,” Dean immediately responded and leaned back on his bed. “And I’m not discussing this with you.”
“You cannot keep me locked up,” Sam responded and Dean could see how much it cost him to keep from yelling.
“Yes, I can. And I will.” Dean watched as Sam stopped pacing to stare at him. “I’m calling the shots here Sam, since I can’t trust you to make the right decision, can I?”
Sam’s eyes were furious and anybody else would have felt threatened by the way he was posturing but not Dean.
“It’s been over a week-”
“My offer still stands,” Dean just said, not willing to get into it.
“I’m not gonna-” Sam said but stopped again, looking down at his crotch, the fight draining out of him.
“Okay,” Dean shrugged.
-
Three days later Dean was fed up by Sam’s attitude. It was worse than when Sam had been a teenager and he was just about ready to put him over his knee.
Actually… yeah that might not be such a bad idea.
“Stop being such a bitch,” Dean growled out when Sam started arguing again.
“I’m not-”
“I swear to go, Sam, you’re being a child about this,” Dean said, stalking closer to his brother.
“A child?” Sam asked indignantly.
“Yeah, and d’you know how to deal with a misbehaving child?” Dean asked, eyes dangerous as he went for the lunge.
“What?” Sam asked, not fast enough to escape Dean’s grip as he turned him around, hands trapped behind his back.
“I think you need a good spanking, Sammy,” Dean explained as he manhandled Sam and himself down onto the bed, Sam awkwardly bent over his knees. Sam was almost kneeling on the ground himself but Dean tutted as he tried to move away, bringing his free hand down hard on Sam’s clothed ass.
“Dean-”
“No, let’s say ten okay? One for each day you’ve been a bitch,” Dean spoke over him, pulling harshly at the sweatpants Sam was wearing.
There was a lot of wiggling and complaining until Dean had finally managed to expose Sam’s ass, the metal cage uncomfortably digging between Dean’s thighs.
Dean thought about drawing this out but that would only result in more bitching and so he didn’t make Sam count them as he delivered ten precise swats, five to each cheek. The skin was red and puffy, Sam’s still complaining under his breath but he was also wiggling and rubbing himself on Dean’s lap.
“And just to make sure you stop complaining-” Dean said just as he pulled Sam’s cheeks apart, exposing the tight furl of muscle hidden between.
“What?” Sam asked, voice a little choked off.
A thick glob of spit dropped between the cheeks and Dean rubbed it in with his thumb, pushing it into the hole.
“Dean-”
“Stop wiggling,” Dean just said and clamped one hand down on Sam’s hip as he fully pushed his thumb inside Sam. “You’re bitchy because of your blue balls, right? I’m just gonna fix it.”
Dean’s thumb got replaced by his fingers and by the time he had two steadily pumping in and out of his brother’s tight hole Sam had gone from wiggling to shaking.
“I don’t-” Sam whined. “I can’t-”
“Yes, you can,” Dean said, stroking over Sam’s prostate again and he could feel the way his thighs were getting soaked with Sam’s pre-cum.
He kept on fingering Sam, not wanting to stretch him or to draw this out, he just wanted to milk Sam dry so hopefully his attitude would get better too.
“Dean, I-” Sam moaned, whole body shaking and Dean knew that it would not take long now.
A few more precise strokes over his little brother’s prostate and Sam bit off a yell as he clenched down on Dean’s fingers.
It was a shame that Dean couldn’t see his little brother’s cock just drooling cum between the metal bars of the cage. He’d bet it looked all cute so caged up as Dean didn’t let up the movements of his fingers, making sure to really drain Sam’s balls.
Sam was breathing heavily, still shaking when Dean finally pulled his fingers free. His brother was limp on his lap and it was difficult to get him on the bed but once Dean finally did he looked down at the fucked out mess Sam was. And yes, indeed, Sammy’s cock all caged up and smeared with all the cum Dean had milked out of him looked just as pathetic and cute as he had expected.
Well. Maybe he’d just have to keep him locked up a little longer. Just to be safe of course.
Chapter 9: Day 8: Cages (Lucifer x Michael)
Summary:
Day 8: Cages (Lucifer x Michael)
Notes:
Am I happy with this? Not really
Is the use of powers realistic? Probably not
Chapter Text
Time worked differently in the cage and Michael was still trying to get used to it. What he did not need to get used to, no matter how much time had elapsed was his bitchy, dramatic little brother. What also didn’t change was the fact that Michael had to put him in his place and seeing how Lucifer had spent far too long alone in the cage not being disciplined, it was urgently needed.
And now might just be the perfect time to start again.
“Lucifer,” Michael warned before he pushed him against the cage wall, the cold metal biting into his little brother.
“Michael,” Lucifer ground out and tried to fight the hold the older had on him.
“I think you forgot your place,” Michael said, binding Lucifer’s wrists.
It didn’t stop the younger from thrashing but MIchael put a quick stop to it by making sure to keep him in place.
“You’re making this harder on yourself, you know that,” Michael tutted.
“You-”
“You better watch what you’re saying or I will gag you too,” Michael interrupted him casually, walking once around his brother who was kneeling on the cage floor by now.
Michael easily kicked Lucifer’s elbows out of the way, making the younger crash onto the floor with his shoulders though he still wasn’t satisfied with the position. Back in heaven Lucifer’s chest used to almost meet his knees, properly presenting himself to his superior brother.
“You’re out of practice, little brother,” Michael commented, making sure to sound as disappointed as he felt.
“Shut up,” Lucifer growled, earning himself a harsh smack to his ass.
Getting rid of their clothes was nothing more than a thought and Michael stopped for a second to admire the miles of milky skin he hadn’t seen in so long.
“You keep forgetting who’s in charge here, Luci,” Michael smacked his brother’s exposed ass again, the flesh turning pink.
Lucifer tried to squirm again but both he and Michael knew what would be happening next - it wasn’t the first time he had to discipline his little brother after all.
When not in their celestial form there was a certain amount of preparation needed for the act even when it was supposed to be a punishment but Michael didn’t bother as much as he had seen humans do. Spit had to do as he stretched Lucifer with two fingers immediately. Michael appreciated that Lucifer didn’t make too big of a dramatic performance out of the prep - not that he hadn’t in the past though, with complaints and whines.
Michael’s cock was rock hard and dripping by the time he finally entered Lucifer, the squeeze tight in these forms. He grabbed his brother’s hips and pulled them tight against him, sinking his cock all the way inside.
This was a punishment so Michael went as rough as he could, pushing and pulling at his brother, the wet slaps of skin on skin only broken by small muffles from Lucifer. The cold metal must be burning his cheek and shoulders and knees but Michael did not care, a few scrapes were to be expected while disciplining.
“I thought the cage would teach you well enough on its own but apparently we were wrong,” Michael said, hips unrelenting. “Don’t touch it-,” he growled, interrupting what he actually wanted to say in order to stop Lucifer from touching his own cock.
“But-”
“No! Father, you really need to be reminded of your place,” Michael growled, binding Lucifer’s hands again where he had apparently slipped in his pleasure.
The punishing rhythm continued until Lucifer’s breaths began to stutter and he clenched down on Michael’s cock. His little brother stiffened as much as he could as he came onto the cage floor.
“You better remember your place when we get out of here or-”
Michael’s threat was cut off by his own orgasm, his seed shooting deep inside his brother, another reminder to Lucifer of who was in charge here.
Chapter 10: Day 9: Shibari (HunterCorp!Sam x HunterCorp!Dean)
Summary:
Day 9: Shibari (HunterCorp!Sam x HunterCorp!Dean)
Chapter Text
“I’ve been shopping,” Dean confessed in the evening.
Sam turned his head to him, smiling at the way Dean was framed by the glowing sunset. The air was warm and Sam was only wearing his swim shorts after spending the whole afternoon in the pool or tanning in the Brazilian sun.
“Okay,” he said when Dean stayed silent. “What for?”
“I want to try something new,” Dean said, cheeks just a slight touch of pink.
Sam raised an inquisitive eyebrow, smile turning a little more sly. “In the bedroom?”
Dean’s cheeks pinkened up a little more but he nodded. “Yes.”
“Well then, let’s go.”
-
Sam sat naked and patiently waiting in the middle of their bed as Dean opened a box to take out a length of red rope. He reached out to touch it, the material feeling not nearly as scratchy as he had feared.
“I wanna tie you up,” Dean said, letting the rope flow through his hands.
“Okay,” Sam agreed, not needing anything more to agree but the knowledge that this was something that Dean wanted and so Sam was going to give it to him.
“You need to tell me when it hurts or when you want to stop or-”
Sam chuckled and patted Dean’s cheek. “I will, don’t worry,” he said before kissing Dean briefly.
They didn’t have any experience with this type of bondage, only getting tied up occasionally on a hunt but pretty soon Sam figured out that Dean had obviously done research with the way he was winding and tying the rope around Sam.
His arms were pulled behind his back, wrists and forearms tied together. Rope around his chest and stomach, his pecs framed and Dean took a few seconds to lick and nip at his nipples until they were pink and sensitive and Sam was whining.
Dean didn’t stop there though, winding the rope further around him, thighs spread open, lower legs meeting the backs of his thighs. Sam would have expected himself to feel uncomfortable with being so tied up and helpless, especially once Dean turned him onto his side but no, he felt safe and secure in his bindings with Dean’s warm hands running all over his body.
He certainly felt safe enough for his cock to lie hard on his belly, his own pre-come soaking into the rope there.
“Fuck, Sammy, you look so pretty all tied up for me,” Dean said, stepping back and admiring his work.
Sam felt himself flush at the compliment, no way to hide himself away from Dean’s appreciating eyes, not that he really wanted to.
“You’re not just gonna look at me, are you?” Sam asked, a little worried that Dean had planned the rest of the evening very differently than Sam had expected.
“Nah, Sammy, you know I can never keep my hands from you,” Dean said, smiling down at him before he divested himself of his clothes.
His older brother kneeled on the bed a moment later, dipping down and cupping his cheek before kissing him softly.
“Gonna make you go crazy before I even get inside you,” Dean promised him, fingers skimming down his chest, over his nipples and to his cock. He gave it one firm stroke before he squeezed the base tighter. “Next time, I’m gonna tie this up too,” Dean promised, making Sam groan at the image.
Chapter 11: Day 10: Oral Sex (Sam x Dean)
Summary:
Day 10: Oral Sex (Sam x Dean)
Chapter Text
The road was smooth and empty, in the middle of nowhere in middle America. Roads like they had been driving on all their lives and Dean knew them like the back of his hand. Enough so that he didn’t need to do all that much concentrating while driving along in his baby.
They had no real destination in mind, just going wherever the wind took them and then checking local newspapers for any kind of supernatural event.
Sam was shifting in the seat next to him and a smirk formed on Dean’s lips as he was reminded of the night before and the surely sore ass Sam had right now. Dean had taken hours to eat Sam out, to tease him open, to stretch him wide, to make him cum twice before even getting inside him - no wonder he was squirming in his seat now.
But instead of feeling bad about it, it only made Dean’s cock twitch in his jeans, slowly filling up with every shift of Sam’s hips and every quiet complaining noise.
“D’you need something to distract yourself?” Dean asked, looking over at Sam briefly and winking when Sam looked back.
“What?” Sam asked.
“It’s like someone put ants in your pants with all the wiggling,” Dean said, grinning.
“There are no ants-”
“Oh, I know why you’re all squirmy, I just wanna know if you need something to get your mind off of it.”
Sam narrowed his eyes slightly. “Depends on what you’re talking about.”
Dean nodded towards his crotch, watching Sam look down. Sam rolled his eyes but Dean could see him giving in.
“You’re a horn dog, Dean,” Sam mock-complained. “Almost forty and your dick still gets hard by a stiff breeze.”
“That’s stretching the truth a little, don’t you think?” Dean asked, looking between the road and his brother.
“Nope and I bet you have the stamina of a teenager too,” Sam joked.
Dean scoffed. “Why don’t you find out?”
Sam scooted closer, turning slightly before he started fumbling for Dean’s pants. He scooted forward a little so as to give Sam more room and his little brother used it immediately to finally open his pants.
His hard dick was pulled out and he hissed between his teeth when the cool air of the car hit the wet head of cock. It was quickly replaced by warm, moist breath as Sam leaned down, scrunched together on the benchseat, so he could take Dean’s dick in his mouth.
“Fuck,” Dean groaned, hands gripping the steering wheel tightly as Sam kitten licked the head of his cock.
Sam bobbed his head up and down his cock, lips tight around him but teeth never even grazing him. The sounds were obscene and Dean had to turn the radio lower so he could hear it better. His hand fell to the top of Sam’s head, twisting in the long hair and lightly pushing him further onto Dean’s cock.
“So good, Sammy,” Dean groaned, the car slowing down as he got more preoccupied.
Sam hummed around him and Dean’s grip tightened on his hair. He didn’t like to admit it but maybe his stamina wasn’t as good as he wanted it to be but who could blame him? His little brother’s mouth was soft and wet and so fucking perfect around him, the suction just right and he made those sinful noises.
“Fuck,” Dean yelled, as his hips jerked up into Sam’s waiting throat. He pulsed deep in Sam’s mouth, his little brother obediently swallowing what he was giving him.
Sam pulled off with a pop and grinned up at Dean. “Told you, you wouldn’t last.”
His sass was a little undermined by the slight croak to his voice but Dean still glared at him. “Shut up or I’ll give you something more to squirm about.”
“Oh, I’d like to see you try.”
Chapter 12: Day 11: Somnophilia (Sam x MoC!Dean)
Summary:
Day 11: Somnophilia (Sam x MoC!Dean)
Chapter Text
This was simply unfair and nobody could expect Dean, in the current state he was in, to turn this temptation down.
Sam was laying on his bed, in only a towel that had halfway unraveled already and the mark sang with the desire to take.
Dean hadn’t actually been gone for long this time, had even managed to keep in touch with Sam so his brother should have known that he was coming home - which also meant that him laying here on Dean’s bed basically naked was a clear invitation, right?
The mark wasn’t the only thing that got excited at the view and he could feel his cock harden in his jeans.
“Oh, Sammy,” Dean murmured as he stepped further into the room and closed the door behind himself. The dim light of his bedside lamp was enough for Dean to see the way Sam’s skin pebbled up with goosebumps as he ran a hand lightly up his brother’s leg.
Sam was on his side, legs slightly drawn up which had loosened the knot in the towel.
“What a coming home present, huh? Gotta let me unwrap it?” Dean asked, knowing there would be no answer.
The dark circles under Sam’s eyes spoke of sleepless nights and Dean suspected that he was conked out for good now that he was finally sleeping.
“Let’s see,” he muttered, fingers picking at the loose knot and pulling one side of the towel away. The other side followed quickly and Dean was blessed with the sight of his giant of a little brother, naked in his bed, soft dick laying on his thigh as he slept.
Dean opened his jeans, shoving his hand into his boxers and began stroking himself at the sight. There were many options of what Dean could do now but it had been too long since he had simply been inside his little brother so it was quickly decided.
With a little effort, Dean rolled Sam some more until he was laying more on his front, one leg drawn up and there was only a little snuffle until he settled down again.
He always kept lube in his bedside table and he retrieved it now, pulling Sam’s cheeks apart and spitting on the revealed hole once before pushing a lubed finger inside. As much as he wanted to play and toy with Sam’s yielding body, the throbbing in his cock spurred him on.
Sam was tight and a sense of possessiveness, starting from the mark, ran through Dean at the knowledge that Sam had not fucked anyone, probably not even a toy since Dean had last been here. It also meant that opening Sam up should take more time and care but Dean had to rush through it, too wound up to take his time. He added a second and third finger not so carefully, especially once Sam started to slightly squirm as his sleep got more disturbed.
“Shh, Sammy,” Dean whispered, readjusting on the bed and slicking his own cock up with the lube.
It was too late though and Sam grumbled something before trying to turn his head.
Dean used the last second of calm and peace to hold Sam’s cheeks open with one hand and to guide himself inside the tight hole with the other.
He groaned as he pushed inside, Sam squeezing down on him as he woke up further.
“What?” He asked, sleepy and confused.
“Just relax, Sammy,” Dean told him, pushing him back into the mattress as he began to move.
“What are-” Sam tried to ask but his voice was muffled by the blanket.
“Came back and found you basically naked on my bed, Sam. What a nice invitation for your big brother,” Dean said, finally fully thrusting inside Sam.
Sam stiffened a little. “No, that’s not-”
“Opened so nicely for me, Sam,” Dean continued, gripping Sam’s hip and pulling him closer.
His brother moaned instead of answering and Dean decided talking was unnecessary if he just kept fucking Sam good enough.
Sam’s prostate was easy to find after years of practice and soon Sam was mewling and moaning and thrusting back against him.
“Go on, Sammy, take what you need,” Dean told him, letting Sam rut back against him before grinding into the bedding in front of him.
“Dean,” Sam groaned and yeah that tone meant he was close.
“Come for me, Sam,” Dean ordered, the mark burning with ecstasy when Sam followed his command and squeezed down on his cock as he came.
Dean rutted roughly inside Sam a few more times before he pushed Sam into the bed as he came deep inside him.
Chapter 13: Day 12: Kneeling (Jared x Jensen)
Summary:
Day 12: Kneeling (Jared x Jensen)
Notes:
This is my first time writing J2 so please be kind :)
Chapter Text
Jensen had gotten over the fact that Jared was taller than him years ago, no reason to be bothered by things he couldn’t change - not that he wanted to change anything about Jared really.
It was however still nice and satisfying to look down at the taller man every once in a while, especially so if he was kneeling in front of Jensen, naked as the day he was born.
Another advantage of having Jared on his knees like this was that his usual excited puppy behavior was replaced by a different kind of eagerness.
Jensen stroked through Jared’s hair, hand cupping his jaw and turning his head up until those big multicolored eyes looked at him.
“You ready, Jay?” He asked just to be sure.
“Yes,” the man in front of him replied, hands coming up to pull Jensen’s boxer down, revealing his straining erection.
Eager lips parted and Jared kitten licked the crown of his cock, making Jensen’s hips twitch and jerk.
“Fuck, baby,” Jensen murmured as he watched Jared go from licking to sucking at the tip, lapping up every drop of pre-come that formed.
“Taste so good, Jen,” Jared purred, smiling up at him after he pulled off for a second.
Instead of focusing on the tip again, Jared took Jensen’s cock as deep into his throat as he could. Only with a lot of effort did Jensen keep his hips still so as to not choke Jared too badly, head falling back and moans spilling out when the younger man began swallowing around him.
Jared, the bastard, hummed in response and Jensen wanted to pull him off his dick right then and there and bend him over his knee but he just about stopped himself. Jared very well knew that that was Jensen’s weakness, the way he came the quickest and he was doing it now deliberately.
“Don’t, Jay. Gonna cum right now if you don’t stop,” Jensen said, breathless.
Jared pulled off with a pop and smirked up at the older man. “That’s the point, Jen,” Jared said, grinning before licking at the tip again. “So you won’t be distracted while I show you the new toys I bought.”
And before Jensen could reply or even fully comprehend what the other man had said, his dick was being swallowed again. Jared sucked and toyed with the tip for a moment longer before beginning to really bop his head, taking Jensen into his throat over and over again.
The wet heat and the sucking were already threatening to push Jensen over the edge and he tried to focus on not coming but knew he wouldn’t last much longer.
There was some more humming and Jensen couldn’t help but twist his fingers in Jared’s long hair as he came a moment later, groaning loudly as he jerked and shot his seed down the other’s throat. Jared swallowed, shifting slightly on his knees and Jensen was sure that his own erection was probably demanding attention but the younger continued to suck and lick until he had lapped up every drop of Jensen’s cum.
He wanted to be embarrassed but if he understood Jared correctly, they would have a long night ahead of them.
Chapter 14: Day 13: Medical Play (Sam x Dean)
Summary:
Day 13: Medical Play (Sam x Dean)
Chapter Text
Sam had been beaten and shot and injured more times than he could count. He could however count the amount of times he went to see a doctor about any of those. Usually their field medicine was enough to see them through and in the last years Castiel was only a few prayers away for the really serious stuff.
Which was why Sam was a little surprised when Dean took Sam down to the infirmary after they came back from a hunt where Sam had been taken by the monster of the week. Sure, Sam had some scrapes and cuts and bruises, but it wasn’t anything really serious.
But, it had been a long day that had followed a long week that had followed a long month and so Sam easily gave in and followed his brother down into the infirmary.
There was a cot in the infirmary but Dean steered him towards the examination table which Sam obediently sat down on, swinging his legs up and scooting back.
“It’s nothing serious, Dean,” Sam said to try and appease his brother again.
“Just let me check you over,” Dean said, not willing to argue.
Sam rolled his eyes but let him do as he wished. His brother wiped the few shallow cuts clean, bandaged the deeper ones and even put a few butterfly bandages on the ones that needed it.
He was just about to hop off the table when Dean grabbed the bottom of his shirt to pull it up.
“What are you doing?” Sam asked, holding up his hands.
“Gotta check for broken ribs or anything else,” Dean just said, undeterred as he pulled Sam’s shirt over his head.
Sam just grumbled but knew that arguing wasn’t worth it so he let himself be subjected to more prodding and poking.
“Nothing’s broken, probably not even bruised,” Sam anticipated and earned himself another scowl from his brother when he had to nod and confirm Sam’s suspicion.
“Sam,” Dean said in a warning tone though before unceremoniously opening Sam’s pants.
He struggled out of his jeans at Dean’s insistence and after making sure that there were only minor bruises, Sam had expected to finally be allowed to leave and have that shower he was hoping for.
“Well?” Sam asked.
“Mhm, yeah, still overgrown but everything seems to still be attached,” Dean hummed, running his hand up Sam’s leg once more. He ran it up further though, rubbing across Sam’s crotch and all of a sudden the atmosphere in the infirmary changed.
“Just to be thorough obviously,” Dean said as he pulled Sam’s boxers down. Sam was perplexed enough that he let him and his previously limp dick slowly even twitched alive.
Or maybe not so slowly by the way Sam’s dick was now rapidly filling with blood at just the lightest of Dean’s touches.
“So what’s doing it for you, Sammy, huh? The sterile environment? The antiseptic? Doctor Dean?”
And damnit, that wasn’t it but his dick apparently didn’t care.
“Hmh, it’s okay Sammy, Doctor Dean is gonna take good care of you,” Dean said, stepping back and snapping on a pair of gloves Sam hadn’t even noticed before.
Sam gritted his teeth in discomfort as Dean took his dick in the gloved hand and tried to give it a stroke.
“Dean,” Sam said between gritted teeth. “Don’t-”
“Hold on,” Dean replied as he looked around, spotting the ointment he had used on some of Sam’s bruises and squeezing some of it on his fingers. The slide thankfully got slippier with it and Sam moaned at the way the gloves now felt against his sensitive skin.
“Everything looks good so far,” Dean commented, breaking Sam out of the haze of pleasure.
“Wha-”
“Slightly above average length, average girth,” Dean continued. “Solid production of pre-cum.”
Sam shook his head. “That’s not what it’s actually called,” he informed his brother.
“Shut up, who’s the patient in this scenario?” Dean asked, adding a twist to the upstroke in order to shut Sam up.
Dean’s second hand came up to roll Sam’s balls in his palm, making the younger hiss at the feeling.
“Firm, good,” Dean said, rolling them again.
“Fuck, Dean,” Sam moaned, head falling against the headrest of the examination table.
Dean tightened his grip slightly, stroking him in just the right rhythm. “Doctor’s got you. Gotta make sure the pipes are clean.”
“Stop talking,” Sam groaned out.
Dean did not stop talking. Instead he got even worse and Sam began to worry what kind of porn his brother had been watching.
“Give us a sample then, Sam, c’mon,” Dean said, rubbing over the head of his cock.
“You’re not helping,” Sam grumbled, though his hips chased Dean’s hand, fire building in his gut.
His brother chuckled but thankfully didn’t say anything else until Sam stiffened up and came, his semen covering his own stomach, Dean’s gloved hand and even his boxers.
“I’d say it’s all in tip top shape, still works how it’s supposed to,” Dean grinned, stepping out of Sam’s swatting reach. “Just let Doctor Dean know when it’s time for a check-up again.”
Chapter 15: Day 14: Omegaverse (& Posessive Sex) - (Omega!Jared x Alpha!Jensen)
Summary:
Day 14: Omegaverse (& Posessive Sex) - (Omega!Jared x Alpha!Jensen)
Chapter Text
It had been almost two weeks since they’d had enough time and privacy and most importantly energy to do anything more than just fall into the bed and sleep.
Today would be different though, Jensen would make sure of that.
He had finished on set earlier than Jared, had wished everyone a happy weekend and had set out to plan his own one. Jared had a later start that day and would still be gone for at least an hour, so Jensen set out to start a load of laundry and clean up a little to tame their pig sty of an apartment before the chaos walked back into their place.
The alpha thought about cooking but opted out when his thoughts drifted to dirtying the kitchen any more than necessary after having just cleaned it. There was a pizza place that delivered nearby and it would certainly do for tonight.
An hour later Jared opened the front door, smiling and waving back at their driver when Jensen pulled him inside and pushed him against the hallway wall immediately.
“Jen,” Jared gasped in surprise before Jensen captured his mouth in a searing kiss.
The omega twisted his hands in Jensen’s shirt, pulling him closer as they deepened the kiss.
“Been too long,” Jensen murmured before nipping along Jared’s jaw and neck.
“Yeah,” Jared agreed, breathily.
There was some more heavy making out, Jared grinding against Jensen whose own jeans were getting way too tight for his liking.
“Bedroom, Alpha, c’mon,” Jared whined and pushed away from the wall.
“Pushy, Omega,” Jensen answered but gladly grabbed Jared’s arm to pull him down the hallway and towards their bedroom.
They were impatient in undressing, quiet and quick so that they could continue as soon as possible.
“Present, Jay,” Jensen said, watching as the tall omega scrambled onto the bed. Shoulders down, ass up, just like Jensen liked it best.
“Fuck, ‘mega, look so good,” he purred, kneeling behind Jared and running his hands over the other’s ass.
“Don’t tease, please, alpha,” Jared whined, pushing back into Jensen’s grip.
Jensen tutted but could not blame Jared since he himself was feeling pretty desperate too. They had the whole weekend after all, Jensen had plenty of time to tease his omega later.
“Okay,” he said, kneading Jared’s ass for a moment before pulling the cheeks apart.
Jared’s hole was already glistening slightly and as Jensen pushed a thumb inside just so he could feel more slick leaking out around his digit.
“So desperate for me, aren’t you?” Jensen asked, exchanging his thumb for two of his fingers, stretching the omega wider.
“Yes, yeah, please, Jen,” Jared babbled, hole fluttering around Jensen’s fingers.
Jensen couldn’t take it any longer and he pulled his fingers out, using Jared’s slick to lube up his own cock, knot already beginning to inflate.
There was little more preamble before Jensen lined himself up, pushing all the way inside so that Jared could feel all of him.
“Fuck,” they groaned at the same time.
Jensen leaned forward, folding himself over Jared’s back so he could hold onto his omega’s hair with one hand and bury his face in his neck, licking at the scent gland hidden under the hair.
“So tight, ‘mega,” Jensen growled, hips working roughly.
Jared arched against him, pushing back on every thrust and trying to grab at any part of Jensen he could.
“Alpha, please,” Jared moaned, voice already getting desperate.
The smell and sounds were affecting Jensen and his knot was swelling rapidly, only a few more thrusts and he would be tying with his omega for the first time in two weeks.
“Knot me, Jen.”
And how could Jensen not give his Omega what he wanted.
“You gonna cum on my knot, Jay? Huh, you gonna cum on your alpha’s knot?” Jensen growled as he pushed deep inside his omega, feeling his knot catch and tie them together.
“Yes,” Jared keened, hole tightening up and squeezing down on Jensen’s knot as he came.
“Omega, my omega,” Jensen moaned into Jared’s neck, teeth threatening to bite down as he followed Jared over the edge.
No marks were allowed during filming but Jensen made sure to fill his omega up, to remind him who he belonged to.
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