Chapter Text
Special Agent Henriksen paces around the interrogation table, glancing down at the gorgeous little miscreant chained to it. “Been huntin' you for a long time, boy. Didn't think you could run from me forever now, did you?”
“Ehh, it was worth a shot. Got the feelin’ you enjoyed being behind me.” Dean winks up at him, grinning like the little shit he is.
Huffing a laugh, Henriksen stops and leans down to whisper in his ear. “Don't tempt me. See, that isn't two way glass. Had this room built just for people like you, Winchester. What happens in here stays in here.”
“Oookay. That a promise or a threat?” Dean jerks his head back to hit Hendrikson in the jaw, then laughs at the shocked “ oof” he earns.
A moment later, Dean's face is being shoved against the cold metal. “I heard you like it rough, but that? That was beneath you.”
“Sounds like you finally heard something right. That feel good? Know it’s rare for you to have your facts straight.” Dean grunts against the table, fighting his grip just to test him. “Didn’t catch that last part, you want to be beneath me?”
He laughs, cold and low. “Murder. Identity theft, credit card fraud. Grave desecration. What's that last one about, anyway? Seems like a lotta work to dig up a grave just to get your rocks off on some old lady bones.”
The hand pinning him down releases, and Henriksen sits on the edge of the table. Dean cracks his neck and glances up. “You wouldn’t understand. Wouldn’t believe the truth if it slapped you in the face. Not sure if you seen me, but gettin’ my rocks off has never been a problem.”
“See, I thought you might say that. Doesn’t leave me with many options, though, now does it? Got a trail of bodies behind you so long I need a telescope to see the whole damn thing.” He reaches over, gripping Dean’s chin and puffing out his lips as he sizes him up. “They're gonna make short work of you in there.”
“Think so? Sounds kinky. Don’t go gettin my hopes up now,” Dean says with a wink.
Henriksen chuckles, but it abruptly cuts off. “Stand up. Now.”
“You stand up,” Dean retorts, even though he’s already standing by the time the words come out.
“See, you can be good. Still a pain in the ass, but... I think maybe it's time I return that particular favor.” He trails his fingers along Dean's shoulders and down his side, then slides his hand down his pants to palm him as their bodies press together. “I wasn't gonna do this, but I'm thinkin' maybe it's smart to get in here before the guys in prison use your pretty ass up. What do you think?” he asks as squeezes his cock through his boxers. “Maybe a little practice run before you hit the big leagues?”
Dean’s body is responding before he can stop it. He tugs on his handcuffs with a grunt, his cock twitching in the agent’s hand. “How about you take these cuffs off so we can do it right, boss?”
“Nice try. I don't really need you to do much of anything but bend over, so... bend over.” He pushes him down, then pops the button on Dean's jeans and exposes his ass. “I've had dreams about this ass, Winchester. Nightmares, really —” he splits open his cheeks and spits on his hole — “Hope you don't mind... forgot to pack the lube today. Oops.”
A long, slick finger slides in, and Dean grunts as he pulls on the restraints, but he’s grinning in spite of himself. “Dreamin’ bout this ass, huh?”
“I dream about a lotta things that piss me off, don't flatter yourself. I sure won't.” Henriksen works him open quickly and almost brutally, hissing when he doesn't get what he wants fast enough. With three fingers buried deep and twisting, he reaches around to stroke Dean. “You ever been fucked with your own come before, Dean?”
“Nah... haven’t had the pleasure. Fuck…” Dean bites his lip, giving in to the pleasure. He’s leaking in Henriksen’s hand, rutting into it with the small space he has. “I dunno if you can handle this ass, Henny. Little outta your league,” he eggs him on.
“Please. Call me Victor. You're gonna have to learn to loosen up, pretty boy. Your cellmates, now they won't be as nice as me. Gonna end up tearin’ somethin' in there.” He strokes him faster, reaching his other hand up to wrap around Dean’s throat and Dean groans at the emptiness in his ass. “You’re gonna come in my fist and I'm gonna take this tight little ass of yours right here, you understand? Call it reparations for all the time I spent runnin’ all over this country lookin’ for you.”
Dean's already on the edge, he can't help it. “Y-yeah... fuck... squeeze a little harder!”
“Ahh, hell. Here's me thinkin' you were gonna put up a fight. You want this, don't you, Dean?” He twists his hand and tightens his grip around Dean's throat. “A guy like you, of course you love bein' used. What goes around comes around, huh?” He presses his mouth to Dean's ear and whispers: “Gonna have to come for me if you want my cock, boy.”
“Sonofabitch, Victor,” Dean grunts, just before releasing into his fist with a long, drawn-out moan.
Henriksen brings his messy hand to Dean’s ass and shoves his fingers in, pushing Dean’s come inside his body. “Now if only you behaved this well outside of this room, we wouldn't be here.” The rest of Dean’s spend ends up on his cock and he nudges in, groaning at the tight squeeze. “Ahh, fuck. You always got that game face on, but I knew there was a little slut hidden somewhere under all that flannel.”
“Y’got me, big guy. How about you shut the fuck up and teach me a lesson, huh?” Dean grips the bar he’s cuffed to and tosses his ass back, huffing a deep laugh at the burn.
Victor’s hips snap so hard Dean’s own slam against the side of the metal table. He shoves him down until his neck is pressing into the bar, and a broad, huge hand covers his mouth. “That's about enough outta you. Look on the bright side, Dean. You'll be heading back to your cell filled with enough come you'll be able to handle Tiny… and I promise you, the nickname isn't literal.”
He stuffs two fingers between Dean’s teeth to keep him silent as he hammers in, that thick cock splitting him open so completely that he probably couldn't have said much, anyway.
Dean’s drooling around his hand and he’s hard again, groaning loudly as he slides his tongue between those digits and sucks. He couldn’t use words if he tried, couldn’t even think a full sentence. He’s never been so used before, and he shivers when he realizes just how much it does for him.
“I see you, Dean,” Victor growls out. “Yeah, I had a feeling you'd like this, getting stuffed with your own come and fucked like a whore. Surprised I didn't get you on that too, honestly.” He changes the angle, hitting Dean's sweet spot over and over again. “Gonna come for me again, pretty boy?”
When Dean doesn't immediately respond, he moves his fingers, smacking Dean's cheek. “When I ask you a question, I expect an answer.”
“Unngh!” Dean grunts, his eyelids slamming shut. “Ye— fuck yeah.”
“You'll address me as ‘Sir’, try again.” Victor pulls out, letting his leaking, pulsing cock drag over Dean's hole. “Say ‘yes, Sir.’”
“Fuck!” Dean growls, shoving back in search of his cock. “Goddamnit! Yes, Sir! C’mon!”
He gets what he wants after a hard smack to his ass. Victor slams back in, stroking Dean in time with his brutal thrusts. “Better. Not great, but I knew better. Now be a good little whore and come for me, I wanna feel this ass strangling my cock.”
“You’re a fuckin asshole. Fuck me harder... Sir.” Dean closes his eyes, focusing on the assault to his prostate and his cock his Victor’s hand.
“That's my pretty boy.” He grips Dean's throat again and pulls him up, twisting the hand on his cock as he fucks him deep.
“Oh go—d! Gonna— come!!” Dean leans into his hand, coming soon after all over the floor under the table.
Victor just keeps fucking him until Dean’s a boneless, babbling mess, then finally fills him up with a low growl and leaves fingertip-shaped bruises on his hips. He pulls out, sliding two fingers back into Dean to play with the mix of come. “Got you all used up already, but I gotta say, Dean… that second one was a nice touch.”
Dean holds up a breathless thumbs up, his head rolling on his shoulders. “Never—” he takes a breath — “never thought you could get me off once, let alone twice.”
“You underestimated me. Didn't think I'd catch you, either. Get used to it, Winchester. The guys where you're goin’ are used to livin’ off snacks, and you're a whole ass meal.” Victor fixes his pants and straightens his tie. “See you at the sentencing. It's gonna be the best day of my life.”
~~~~
The trial turns out to be a joke. His lawyers — a spineless twink named Hughie Campbell and a gorgeous-yet-Bible-thumping broad called Annie January — can't be more than a couple of years older than Dean is himself, and since he's only 26… they don't exactly inspire confidence. The combination strike fear into absolutely no one and Dean’s convinced he's going away for life — but the prosecution fails to prove beyond a reasonable doubt that he murdered that chick in St. Louis, so the worst of his charges is taken off the table. Still, the rest of it is bad enough, and Annie bats her doey, stupid eyes at Dean as she tells him God’s judgment will be worse than whatever the court throws at him. Yeah right, lady. Get a damn grip.
In the end, the judge takes pity on Dean and only gives him ten years — which, for four counts of grave desecration, two counts of identity theft and two counts of felony credit card fraud, he got off damn lucky. He’d been looking at the death penalty when that murder charge was brought up.
He's taken straight from the courthouse to intake, and stripped of the whole three possessions he still has to his name. Despite how vehemently he asks anyone and everyone that comes near him, though… no one will tell him what's happening to his car. That's a worse punishment than what the court handed him, not whatever some stupid, make-believe higher power has in store for him.
His cellmate isn't there when Dean’s shoved inside of it to settle in, and he's not sure if that's a good thing or a bad thing. There aren't any posters on the walls or weird, toothbrush-shiv graffiti marks, either, so he doesn't honestly have a damn clue what his cellmate is gonna be like as he makes his bed and checks out the room. All in all, it's really not bad. The toilet isn't in its own room but it is mostly hidden by a small bookshelf, which is better than he anticipated.
After that, he's given a quick tour. There's a small common area with a tv and a couple of couches, and he laughs to himself when he sees the extremely vulgar note taped to the fridge warning people against eating or drinking something they didn't buy.
The guard doesn't share his amusement.
Outside, the prison yard looks exactly like he thought it would. A basketball court, a few picnic tables, and a shitload of concrete and metal. The sun beats down directly in his face and he shields his eyes to try and see out past the fence and how far he'd have to run to reach freedom — he already knows he won't make it in this place a full ten years.
“Oye!” the guard snaps. “Don’t even think about it, ya cunt. Move along.”
Dean smiles innocently. “Just enjoyin’ the view, pal. Wouldn't dream of it.”
Unamused, the grizzly bear pushes Dean back toward the door. “It’s chow time.”
The food ends up being every bit as shitty as he feared it would be, and the lack of pie makes him want to bust out this instant. No way he goes a full decade without pie… he’d rather hang himself with his 100 thread count bedsheets.
Despite keeping his eyes down and minding his own damn business like he heard he was supposed to, Dean barely gets through his dinner before he hears a low voice behind him.
“Look what we have here. Fresh meat.”
He expected this, and honestly, he hasn’t been laid since Special Agent Douchebag bent him over that interrogation table, so he’s definitely on board — still has to play hard to get, though. He doesn't have a single intention on making this easy for any of them. “You can’t afford this cut of meat, buddy. Heard there’s bologna a few cells down, more your speed,” Dean says with a wink, then clicks his tongue as he gets up to face the man.
He's a damn giant, is what he is. Bright blue eyes and a scruffy, graying beard, and muscles for days. Next to that Australian — or is he British? — hunk of a guard he just left, this guy is easily the best thing Dean’s seen yet.
The giant chuckles, gallic shrugging. “Funny. Name's Benny. And brotha, look around you. I'm the best you're gonna get in this block.”
Cajun? Seriously? Everybody around here got a hot-ass accent? Dean sniffles and checks him out. “I’m Dean, and you’re right about that, Benny. Gonna make it worth my while? Been craving a Twinkie for days.”
“Oh, c’mon, now, chere. I don't pay for shit around these parts… I take it. How do you think I landed here in the first place?” Benny stands, reaching over to cup Dean’s chin. “Drop the soap, don't drop it, doesn’t make a lick of difference. I'll have you on your knees before lights out one way or the other. Take care, now. I'll be seein’ you soon… and good luck findin’ that Twinkie.”
Benny walks away to talk to a guard, and a skinny dude comes over and sits next to him to take his place. “Winchester, right? I'm Fitzgerald, but if you promise not to steal my cookies, you can call me Garth.”
So that's a no on the accents, then. Damn. “Alright.” Dean’s still frowning, a little annoyed that arrangement didn’t work out how he hoped. But he isn’t about to give up yet — someone will take that deal eventually, and in the meantime, he’s got a little fight on his hands. “These guys threaten you daily, too?”
“Not the way they're threatening you. They say I'm too skinny, but... no matter how much I eat, I just never seem to gain any weight.” Garth smiles and pats his stomach, but jerks his head back toward Benny. “If you want to avoid getting threatened, he's your guy. Been in here for a dime already, and they say every few years, he picks a toy. No one ever fucks with Big Ben's toy.”
“You sayin’ I’m his next toy?” Dean wonders if that means he’d just have to deal with the one guy, and then wonders if that’s better than the alternative.
Garth shrugs. “I'm saying you can be, if he likes you well enough. He's a good dude... for being who he is. A lot better than some of the others, that's for sure.” His eyes travel to a slightly older man. “That's Ishim. He's... well, you'd just better steer clear of him.”
Dean looks over and Ishim is already eyeing him. “Shit. Alright... what else can you tell me?”
“I probably said too much already.” He smiles apologetically. “You seem like you can handle yourself in a fight, you should be fine.” Before Garth can say anything else, he notices Ishim glaring at him and swallows thickly, then stands up abruptly. “I'll see you around, Winchester.”
“Great... friggin awesome.” Dean stands after Garth bolts and walks to lean against the wall, his eyes taking in his new home. Thought there’d be more hot dudes.
Not two minutes later, Ishim is standing in front of him. “Heard you'll trade that sweet ass of yours for Twinkies. That true?”
“Damn. Like high school in here, huh?” Dean stands taller and sees he’s much bigger than Ishim. “Nah, that was a one time offer, guy.”
Ishim straightens up and smirks, nodding to one of his extremely huge, henchman friends. “Think maybe we should give him a tour, shouldn't we? Really welcome him to Cellblock D?”
The oaf behind him cracks his knuckles like they're in some kind of cartoon and pushes Dean between the shoulders. “Walk.”
“Kinda comfy right here. No thanks.” But he pushes again and Dean’s feet are moving, his heart pounding in his chest. He could swing now — maybe get solitary for a day or something — but it’s a temporary fix for a ten year problem. He sees everyone watching, everyone knows what’s about to happen — so he starts walking normal like it isn’t a big deal. It's only gonna be a big deal if I'm a little bitch about it… not on my fuckin’ life, pal.
Ishim sucks his teeth like a creep as they exit the cafeteria and head toward the laundry room. “Should've just taken the Twinkie… things would've gone a lot smoother for you.”
When they get through the doors, the oaf stands guard and crosses his arms as Ishim unzips his jumpsuit. “It's your first day, I'll show you a little mercy. Pick a hole… that pretty mouth, or that prettier ass?”
“If I pick mouth and suck you good, can we renegotiate that Twinkie deal?” Dean wipes the side of his lip and looks down at his cock.
A feral smile spreads across Ishim's face. “Well, it'll certainly help convince me to reopen negotiations. Get on your knees. Oh, and... if you bite me, my friend here will see to it that you'll be fed through a straw for the duration of your stay here. Understood?” He walks forward, jacking himself off.
“Yup. Loud and clear. No teeth.” Dean clenches his hands and drops down, licking his lips and parting them. Up close, it really isn’t a pretty cock, but he barely gets a chance to see it before it's being shoved in his mouth.
Ishim hisses as he thrusts forward, tugging on Dean's hair to bring him closer. “That's it... use that tongue, boy. Don't make me do all the work.”
Dean almost smiles at its size. It hardly reaches the back of his tongue, so it’s easy to hollow his cheeks and slide his tongue up and down until Ishim falls apart above him.
“Shit, you weren't kidding. Sucked a lot of cocks before, huh?” He snaps his hips a little faster as his breathing speeds up, and all Dean has to do is meet his eyes for him to slide out and start stroking himself above Dean’s face. “Right there, open wide. Gonna watch it paint that pretty fucking mouth…”
He obeys, staring up at him with his tongue out and as soon he winks up at Ishim, he comes with a grunt. It spurts all over Dean's face as Ishim pulls his hair a little harder, then shoves back into his mouth until he's empty.
As Ishim fixes his pants after, he chuckles softly. “The Twinkie deal was for your ass. You decide to give that up, you can have as many Twinkies as you can handle. If not, well... I'll just bring my friend along again next time, and maybe I'll let him have your mouth while I help myself to your ass.”
Dean stands, glad he only chubbed up a little from that and that it isn't visible for Ishim. “Alright. And how long do I have to decide?”
“Until I decide I wanna use you to get off again.” He nods toward the towels and mutters as he turns to leave, “Clean yourself up, you look like a whore.”
He wipes down his face and discards the towel, then sits there in the laundry room a while. It isn’t smart; anyone could just walk in... but he needs a moment to think about whether being someone’s bitch in prison is worth it or not.
And right now, he's thinking maybe it is.
~~~~
Luckily for Dean, no one else visits him in the laundry room. He ends up staying there until it's time for work detail to come in and sneaks out quietly before he can get caught, then makes his way to the showers. He'd been excited for this part until he'd actually gotten here — the thought of a bunch of hardened criminals jacking off right in front of him was hot as shit, but he realizes now that's probably not how things are gonna go down at all. Startin’ to think all those prison pornos I watched lied to me.
He gets more than a few knowing looks on his way to the shower block. Every damn one of them knows he just had to blow his way out of a situation, but Dean keeps his head held high as he strips down and gets under the water.
Doesn’t mean he's not nervous as hell, though.
Benny approaches him first, rubbing shitty, prison-issue soap all over his chest as his giant cock swings heavy between his massive thighs. “You look a like a deer in the headlights, chere. Somebody round here botherin’ you?”
Dean’s eyes widen at his size, but he stands straighter and looks around for a guard. His stomach sinks when the only one present slips from the showers without a word. Great. Guess that’s that. “Nah. No one was botherin’ me.” Around them, a lot of others are watching, and most of their cocks are hard like they’re about to get off watching him get raped.
“Relax, brotha. Pretty little thing like you... you'll come to me willingly soon enough.” But instead of moving on, he steps behind Dean. Benny chuckles as he reaches around him for the shampoo, then squirts some in his hand and starts rubbing it into Dean's hair. “Rough first day?”
“You can say that…” Dean’s far from relaxed, but he lets Benny do what he wants. He's really not trying to get his ass kicked while he’s naked and wet.
Sure enough, a couple of the guys close to them start playing with themselves as they watch, and Dean keeps waiting to get shoved against the wall. When Benny's fat cock presses between his cheeks, Dean freezes, still not sure if he’s just being tested right now or if it’s actually happening. “Happy to see me or is that just always a monster?”
“Can't it be both?” Benny ruts against him and brings a hand up to Dean's neck to squeeze, then huffs a quiet laugh as he pulls back and smacks Dean's ass on his way out. “Welcome home, chere. Enjoy your evening.”
He flinches at the slap and forces a laugh, rinsing everything off and grabbing a towel to dry off before someone else can sneak up on him. He rushes back to his cell and stares at the bare walls with a sigh. “Home sweet home.” He lays down, eyes glued on the door.
Eventually, exhaustion wins out over any sense of self-preservation and he gets a couple of hours of sleep before the breakfast alarm goes off.
When his eyes shoot open, he groans. There were a few moments where he thought maybe this was all a bad dream, but when he wakes with his back stiff on the thin-ass mattress, he knows it’s real. Dean washes up and goes to chow, shoveling it down before someone can steal it and chugging the cup of water.
“Oye, Winchester,” the guard from his tour says as he approaches. “Yer work detail’s come in. Yer on landscapin’ duty. You've got one hour before you've got to report outside. Don't be late.”
Not wanting to piss him off, Dean nods and heads around him to go back to his cell, but runs into Garth on the way out. “Hey, what’s with Kangaroo Jack over there? Looks like a guard but keeps bossin’ me around.”
Garth clears his throat and looks a little uncomfortable. “Oh, him? That's Butcher. If you ask me, he likes this job a little too much.”
“Butcher? That his real name?” Dean takes another look at him and lets out an impressed “huh” when he takes in the muscles popping through his shirt.
“Nah. All the guards have nicknames around here. We call him Butcher because he used to be one, but apparently got tired of beating up dead animals and came here to pick on live humans, instead.”
“Yeah? I’ll try and stay on his good side, then. Gettin’ butchered isn't exactly a part of my ten year plan. Thanks.” He walks away without asking about any of the others, knowing Garth doesn’t really want to be seen with him, anyway.
Dean goes into his cell to change into his white shirt and orange pants for outside, and he nearly gets his ass covered up before he hears whistling.
“Whoo! What an ass,” the inmate yells. “Bend over for me, sweet thing, I need some new spank bank material.”
One of the other guards kicks the guy in the back of the knee. “You’re deesgusting, get zee fuck out of ‘ere.” He stops in the doorway as the inmate takes off and eyes Dean. “Ee’s not wrong, though. You ever need… mmm…. protection, you come and find Frenchie, oui?”
Dean wonders who the hell this little guy is protecting, but he learned a long time ago not to judge a book by it’s cover. “Got a few of those offers so far, thanks.”
“Oui, but none as good as mine. I assure you.” He winks, disappearing and yelling after the inmate that ran away.
Chuckling and mildly interested in that, Dean finishes dressing and hits the bathroom before walking outside. He still has a little time, but the sun feels so good on his skin that he closes his eyes with a small smile on his lips.
He jumps when Ishim sneaks up behind him. “See you pulled the long straw. Come with me, it's time to get to work.”
Dean hesitates, standing there for a few more moments and looking around to see where the guards are — but when all he sees is Butcher, he forces his feet to move and follows Ishim.
For the first couple hours, they really do work. Part of the exterior of the prison needed painted and the small, pathetic-looking garden needed dug up and replanted. When they finish with that, Ishim wipes dirt from his brow and points his small, dull rake at Dean's chest. “Shed. Now. You and I have other business to attend to.”
He's about to say no when that same, massive friend of Ishim’s steps up beside him. “Shed's that way,” he grunts.
The last thing Dean wants is to suck his nasty cock again, so he stays against his better judgement. “It's a nice day outside. We can talk here.”
“Tiny... handle this, please.”
“I said... shed's that way.” The behemoth shoves Dean so hard he falls over, hitting the concrete.
He jumps up as fast as possible, not wanting anyone to see him on the ground and dusts himself off. “When’d you become his bitch, Tiny?”
Ishim tsks. “I'm technically the crew captain here. It would be a shame if I had to report back and say you were being uncooperative on your first day. You're still on the clock.”
“I did all my fucking work.” Dean’s fists clench but he starts walking, not wanting to deal with fucking Butcher, too. “I'm not sucking you off again.”
The shed shuts the shed door behind them, casting them into shadow, but not complete darkness. “I've had better, anyway. But we're not here to talk about your subpar blowjob skills. I made you an offer. You can either give that ass to me willingly and you'll be rewarded with... what was it that you wanted? Twinkies? Those. And if not, I'll just take it anyway. So—” he stalks forward — “what will it be?”
His heart is pounding in his chest as he stands there, trying to think of some way out of this. Shoulda fought while I friggin could. Where the fuck is Butcher or Benny when you need ‘em? Hell, even Frenchie. “Nah... you can keep the Twinkies. Lil’ too sugary for me.” He offers a grin, though it doesn't reach his eyes.
After a single nod from Ishim, Tiny grips Dean by the back of the neck and bends him over the toolbench. “This could've been fun for both of us, but now… it'll just be fun for me. And maybe Tiny,” Ishim adds as Tiny shoves down Dean’s pants.
The door flies open before Dean’s asshole can even clench and Butcher takes a few, thunderous steps in. “Ishim, you stupid little cunt. Get out’a my sight.”
Ishim turns tail almost instantly. “He asked for it. Offered to sell himself to m—”
Thwack.
“Ow! Fu—” Ishim grabs his chin and darts out of the shed, Tiny right behind him.
The door swings shut once more as Butcher checks out his knuckles with a satisfied hum, then fixes his eyes on Dean’s ass. “Didn’t even break the skin.”
Dean stands, trying to right his pants, but he can see the way Butcher is looking at him. “Thanks for that.”
Butcher steps forward, shaking his head. “Keep 'em down, kid. I didn't save ya out'a the goodness of me heart. Ass like that doesn't walk in 'ere often.”
Sonofabitch... at least he’s better looking. “Shit…” Dean sighs and pulls them down again, his heart hammering in his chest as he bends over. “So uh... you won’t mind if i get off too, right?”
“I prefer it.” He pulls out a small bottle of lube and starts fingering him. “Tight, ain't ya?”
“Yup. Been a— fuck... been a while. You got some fatass fingers, Butch.” Dean closes his eyes and wonders if he’ll have a single encounter here that he doesn't have to get on board with after it's already started. “C’mon, big guy, don’t let me down and go easy.” He reaches down and grips his slowly chubbing cock as Butcher shoves in a third finger.
A rough, callused hand replaces Dean’s own as Butcher brushes the tip of his prostate and starts to stroke him. “Be a good lad and make a little bitah noise fer me.”
He grunts whether he wants to or not and braces his hands, letting Butcher take over so he can focus on the pleasure. Soon, his cock is hard in Butcher’s hand and Dean is moaning, pushing back onto his fingers. “Let me have it, fuck... c’mon.”
“Atta boy.” Butcher pulls his fingers out and shoves his cock in without warning, tugging Dean up until their bodies are flush. “Ahh, fuckin' 'ell, knew this ass would be top notch.”
“Goddamnit... and I knew you’d have a fat cock.” Dean moans at how full he is and pushes back, then gets bent roughly over the tool bench as Butcher lengthens his thrusts.
Each brutal snap causes the tools on top to rattle and the table slams against the shed wall hard enough to shake the glass. It actually has Dean more turned on than he’s been in months. His cock throbs and leaks so he reaches down to jack off, keeping pace with each brutal thrust. “Fuck... right there... ah, shit.”
Butcher does nothing but grunt as those thrusts somehow become harder. His hands slide down until he's gripping Dean’s thighs and lifting him clear off his feet.
“Ah, fuck... Butc— I’m—” Dean moans loudly just before he comes all over that tool bench, sighing a laugh when he finishes. “Goddamn!”
The guard mutters something under his breath as his cock pulses and he fills up Dean's ass, humping him until he finally empties. He pulls out with a growl and squeezes Dean's ass, then smacks it hard enough to make the skin jump. “That's more like it.”
“You’re tellin’ me. Don’t get used to it. You caught me in a horny mood. Just didn’t want that creep,” Dean lies. The truth is, that was the best he's felt in years — but this asshole guard doesn’t need the ego boost.
Butcher scoffs, but snatches a clean rag from a nearby table and tosses it to him. “Well, ‘ave it yer way, then. Might put some ice on that before lights out.”
“Nah, I’m a big boy. Thanks.” Dean cleans up and then moves to walk past him, blushing when he sees a few inmates around the shed. “Enjoy the friggin show?”
Again, he's rewarded with a handful of whistles and catcalls that don't stop until Butcher threatens them.
He feels kinda low — not that he’d show anyone — and he walks with his head as high as he can. As far as fucks go, it wasn’t bad. The orgasm was even better than with Henriksen, but he wonders how many more assholes are going to try and fuck him. He thinks of Benny’s offer, but quickly pushes it away and gets back to work, ignoring Ishim’s angry glares.
~~~~
When Dean returns to his cell, he's limping just a little from the abuse his ass just took. More than anything, he just wants some damn peace and quiet — but there's yet another giant waiting to greet him when he steps in. This one looks like he could be gorgeous with all that wavy blond hair and hard muscle, but his face is beat to hell and one eye's half swollen shut.
“Hey. You must be Dean,” he says as he holds out a bandaged hand. “I'm Jask. Jask Morningstar. Guess we're cellmates.”
“Guess so.” Dean shakes his hand but drops it quickly. “You alright?” He sits on his bed with a flinch, eyeing his new cellmate’s injuries. “Guard or inmate?”
Jask chuckles. “Both, actually. This fucker named Ashton clocked me trying to start a fight and Mother’s Milk got involved. Somehow, it became my damn fault and I got sent to solitary for three days.”
“Sounds shitty. How long you been in here? Think it’s obvious I’m new,” Dean says with a bitter laugh.
“Bout a year and a half, give or take. But that's good news for me, means I'm out soon.” He grins, but then winces and picks at one of his wounds. “Tell ya what, I won't ask you what you did if you don't ask me.”
Dean chuckles at that. “Deal. You wouldn’t believe me, anyway.” He lays back on his bed with a grunt. “Fuck... wait, am I in your bed or somethin’?”
“Who cares? They're equally shitty. Sleep wherever you want, just don't be surprised if I try to spoon you in the middle of the night.”
“I'm a little sore back there, so don’t try anything just yet,” Dean says with an amused grin.
Jask huffs. “Hate to break your heart, but I won't be trying anything. Let's just say I've got someone waiting for me. Promised him I'd keep it in my pants, but he knows what a baby I am. Platonic cuddling is all you'll get from me.” He pauses for a moment, then adds, “Seems like you've already met the horny fuckers here, anyway.”
“Yeah. Been a rough couple days. That’s good for you though, man... none of these assholes try and... y’know…?” Treat you like you're a piece of meat?
“Nah.” Jask sits forward and adjusts the bandage. “Told everyone I have IBS… they left me alone real quick. I double up on beans at dinnertime and let a few rip at opportune moments, no one comes near me. Sorry in advance, roomie.” The laugh he lets out is contagious, and Dean joins in, finally feeling a little bit better.
“Man, kinda wish I thought of that. Sucks the hottest guy here is taken though, woulda preferred you to anyone else here.”
“You think I'm hot now, wait till you see me when I'm healed.” Jask flops back and glances over at him. “So who was it?”
“Uh... which time?” Dean attempts to joke, but he can’t even fake a smile. “Butcher earlier... after stopping Ishim. Some rescue, eh?”
Jask grimaces. “Yikes. I mean, hey... Butcher's kinda rough, but he's mostly harmless. You say no? From what I heard, he doesn't touch the ones that say no. Ishim's a fucking creep, though. Don't think he'd care either way.”
“Guess I need to use my words, then. And nah, Ishim don’t care. Definitely told that asshat no. It wasn’t so bad, I got off for the first time in a while so…” he trails off with a gallic shrug.
After a moment, Jask gets up and digs under one of the books on the bottom shelf until he's pulling out a small bag of pills and tossing them to Dean. “Here, take a couple of these. They're just those hybrid Advil things, nothing illegal or fishy. I uh… got a connection in the medical ward,” he says with a smirk.
Dean takes them in the sink and lays back down. “Thanks. I’ll pay you back somehow.”
The pills disappear under the same book. “Don't sweat it. I don't really need much, and like I said... I won't be here much longer. Just gotta keep my nose clean for the next few months and I'm out.”
“Good for you, man. I’m lookin’ at like ten, but... maybe good behavior can get me out a little sooner. Still... in it for the long haul.”
Jask glances over with a concerned expression. “You're not gonna last. If I were you, I'd get on the good sides of Butcher, Benny, Frenchie… Kimiko. But good luck with her, crazy woman has never uttered a damn word to anyone. But she throat punched some guy the first week I was here for fucking with Fitzgerald and he hasn't uttered a word since, either.”
“Benny?” Dean looks over to meet his eyes. “He's uh... he’s offerin’.” He licks his lips nervously. “You sayin’ I should be his bitch...?”
“Yeah, I am. He won't touch you without your permission and he'll kick the living fuck out of anyone else that tries.” Jask lowers his voice. “Hell, if I wasn't otherwise taken and not all that into bottoming, I'd have been his bitch. He's the only one around here people are actually scared of, 'cept maybe Tiny and the Angel of Thursday.”
“The what of Thursday? Angel? People are scared of an angel? Sounds ass backwards.” Dean chuckles at that. “Who am I to talk about ass backwards?”
Jask shrugs, grabbing a stress ball and tossing it against the wall over Dean’s head. “All I know is that he works over in Absolution Row, and he's far from an angel.”
He hasn’t even seen this so-called angel, and he has a feeling he wouldn’t want to. “So... my best bet is Benny. And if I try and go it alone…”
“You can take your chances,” Jask replies. “But I wouldn't advise it. You've been here, what... two days? Multiply that by ten years and tell me if you think you can go it alone. Benny's a lifer. He's not going anywhere.”
Dean gets quiet for a while, thinking about what that would look like. “I gotta like... hold his pocket and shit?”
Jask barks a loud laugh that echoes off the walls. “No, no. I think people around here use the word "toy" a little loosely. He just wants company, honestly. Someone that isn't gonna betray him and is half decent in bed. Can you blame him?”
“Not really, no... you his salesman or somethin? Makin’ it sound pretty damn good, buddy.”
A weird look crosses his face. “Yeah, maybe a little. He uh... he helped somebody I care about out in a big way a few months back. Figure if I can help you both by pimping you out, then… why not?” Jask asks, shrugging it off as he tosses the ball again.
“Well, alright then. I’ll think about it.” Dean rubs at his temples with a sigh. “You know I hadn’t even come out of the damn closet before I came here? Now my ass is being tossed around like a friggin hot potato.”
Jask snorts, then goes silent as a couple of inmates walk by. “Don't say that too loud, you think it's bad now… they get the hint you haven't always loved being stuffed full of cock, they’ll start doing it just for the power trip.”
“Good to know. Thanks for all the ass advice.” Dean sits up and then stands. “Hungry?”
The look he gives Dean suggests he's always hungry. “Kitchen should be open for dinner, if we hurry up we can finish before any of your friends arrive,” he teases.
“Your friends. Not my friggin friends.” Dean rolls his eyes and starts walking that way, a small limp in his step. “Sure you wanna be seen with me? Garth won’t even sit at the same table.”
Jask purses his lips. “Little twerp is scared of his own shadow. He’ll be fine now that I'm back, you'll see.”
Sure enough, the second Garth spots them come in, he scoots to make room at his table. Not like anyone else was sitting with him, anyway, but still. They get their food and Jask nudges Dean that direction. “Go on. Guess I better walk behind you before someone else trips and falls into your ass.”
“You always a smart ass, Loreal?” Dean walks in front, chuckling until he sees Butcher. He looks down, trying not to flinch too hard when he sits.
Garth's smile fades when he sees Dean's face, but he doesn't comment. Instead, he turns to Jask. “How was solitary this time?”
“Same as last time, and the time before that. Heard you were trying to avoid my cellmate here, Fitzy. What's that about?”
His face reddens. “I'm sorry about that. I'm... not very good with new people.”
“Not a big deal. Don’t gotta explain shit to me.” Dean starts eating, staring down at his plate and eating quickly. He looks around after a few bites and sees Benny, letting their eyes linger a little longer than he should and then looks away.
Jask reaches over to steal a piece of meat from Garth's tray and chews it with his mouth open. “Tax for being a twerp.” He smiles warmly, though, and Garth returns it.
Benny watches Dean from his table periodically after that, but once again gets up to talk to one of the guards. “Who’s the guard Benny is taking to?” Dean asks curiously.
“Huh?” Jask looks over and chews slowly. “Oh. We call that one Mother's Milk... MM for short.”
“Oh. Heard his name a few times. Why’s he called that?”
He points his fork in that direction. “Cause he just looks like the type of dude that would still be suckin' his mom's tit, that's why. Hey, we're inmates... not poets.”
Dean actually barks a laugh at that — much louder than he intended to — but when Benny and MM look at him, he looks pointedly at his water with a grin still on his face.
“Don't let them fool you, he knows why. Butcher loved his nickname and I’m pretty sure Frenchie made up his own.”
“Frenchie is just self explanatory. Butcher... well, I already got that explanation but I didn't really need it there, either.” Dean stares at the table as his face darkens, realizing maybe it wasn't quite as “fine” of an experience as he made it out to be.
Jask nudges him. “Hey. Finish up. I'll talk to Butcher, okay? It won't happen again.”
“Nah. Don’t need you to do that. Actually, I’d prefer you didn’t. I can handle him. Like you said, I didn’t tell him no and it was better than the alternative. I’m gonna hit the head. See you guys in a bit.”
It doesn't look like either of them want him to go, but neither say anything as he heads out. For a moment, he thinks Benny's gonna follow him — but he doesn't, no one does. He ends up back in his cell after speeding through a half-clothed shower and doesn't realize until he gets there that he never finished his dinner, but when Jask shows up a few minutes later, he shoves a paper towel full of food in his hand. “Eat, or I'll force feed you.”
Dean rolls his eyes but eats, missing when he could just eat all day. He climbs into bed after brushing his teeth and stares up at the ceiling, saying quietly, “Thanks, J. Kinda nice to have someone around who doesn’t wanna fuck me.”
“I absolutely wanna spoon you, though... so... just sayin'. Don't be afraid to crawl over here.” He winks as the lights dim for the night but stays on his own side.
“Night,” Dean says with a smile. He won't do it yet, but he'd be lying if he said it doesn’t sound nice. And with the way things have been going… he can use a little more of that.
~~~~
The next week goes by without too many incidents. Butcher wanted a blow job and Benny washed his hair again, but at least his ass had had time to recover.
After a while, the alarm waking him up for breakfast stops scaring the shit out of him, and he heads down alone, knowing Jask usually sleeps through breakfast so he doesn't die during work detail.
There aren't many people down there this early, but the ones that are there are assholes that Dean’s learned to steer clear of. He barely gets his food and sits down before some idiot named Max comes over and steals his only piece of toast.
Dean shoves the rest of his tray away and stands up, instantly swinging on him and busting his nose. The toast falls to the ground and Dean nearly grabs it to shove down the dude’s throat, but he doesn’t want to turn his back for a second.
Max knees him in the gut in an attempt to push him off and spits on him. “Fuck you, Winchester, get offa me!”
A growl rips through Dean’s chest as fury makes him see red. He can handle a lot of shit — but not that. He punches Max repeatedly until two sets of hands drag Dean backward and he slides across the floor, flailing and trying to get up. He gets tossed out in the hallway outside of the cafeteria as Kimiko runs back inside with her baton out, and Frenchie hauls Dean to his feet with a strength that surprises him. He shoves Dean’s chest and points to one of the vacant recreation rooms. “In, now.”
Dean wipes his face and nearly charges back in but instead turns and goes where Frenchie wants. He definitely doesn’t want him as an enemy. The moment the door swings shut, Frenchie backs him up against the wall.
“What's amatter, Weenchester? Strung a leetle tightly all of a sudden?”
His heavy accent actually has Dean relaxing slightly and chuckling. “Ween.” He chuckles again. “And uh, yeah. Am I supposed to just bend over and be everyone’s bitch out there? I don’t let people fuck with my food. I’m in jail, I’ve been forced to fuck and suck my way through — not to mention I haven’t gotten off in over a week. So yeah, leetle strung, buddy.”
Frenchie clicks his tongue. “Oooh, now we're cracking jokes, eh? You're lucky eet was me 'oo pulled you out of zere and not someone else.”
“That so?” Dean looks him up and down and realizes he’s actually pretty damn hot, especially now that he’s felt his strength. “So no punishment from you, Frenchie?”
He seems to be having the same thought, because his eyes rove down Dean’s body and it genuinely looks like he wants to say yes for a moment. “Non,” he says, but doesn't back away. “I prefer my partners to be willing, you see. So much more satisfying that way.”
“That’s a first.” Dean leans in, his eyes flashing slightly. “And what if I’m willing, boss?”
“Call me Frenchie.” He grips Dean's chin and pulls him into a kiss, backing him against the wall again. Dean’s dick instantly responds, his hands gripping at the guard’s waist as he ruts against him, showing him he’s hard.
Frenchie licks into his mouth with a heated growl as he unzips Dean’s jumpsuit and slides a hand in to palm him, gripping his own cock through his pants with his other hand.
“Fuck... take it out, Frenchie. C’mon.” Dean kisses him again as Frenchie fumbles with his belt, and his radio pops off and clatters to the ground. He ignores it, ignores everything but the way their cocks feel when they're finally fisted in Frenchie’s hand.
The guard rolls his hips and braces his free hand above Dean’s head on the wall as he catches his tongue and sucks on it, stroking a little faster.
It’s absolutely the best Dean has felt since... well, before prison. He moans, rutting into that amazing hand and leaking all over his fingers.
Frenchie trails sloppy kisses across Dean’s jaw and down to his neck as he twists his hand, and his movements soon become staccatoed. “Give it to me, Dean.”
“Ah, fuck…” Dean bares his neck as Frenchie starts to bite, kinda hoping he leaves marks to turn off other inmates. “Frenchie— gonna come!”
He drops to his knees and jacks himself off as he sucks Dean’s cock into his mouth, flicking his eyes up to watch him unravel.
“Oh go—” Dean ruts into his throat as he comes, his leg shaking with his release. “Shit... Frenchie... let me have yours.”
The guard swallows and pulls off to lay back on the ground, fucking up into his fist with a strained moan. “‘Urry up, I’m—”
Dean drops down and sucks the head of his cock just as he begins to come. It tastes better than the others too, so he gets a little greedy sucking him dry.
“Fuck,” Frenchie whispers, finally stilling. “See what I mean? It is always better when two people want it instead of one.”
“I fuckin’ agree. Thanks for that.” Dean sits back after sliding his clothes back on and lays his head back against the wall to catch his breath.
Frenchie fixes his pants and grabs his radio, smacking it on his palm to make sure it still works. “In ze future, if you want more toast, I’ll get you more toast. You want more orgasms, I help there, too. Maybe try... less fighting.”
Dean looks at his busted knuckles and huffs a bitter laugh. “Sometimes, I’m gonna have to fight, French. You know that. I really do appreciate it, though.”
He shakes his head with a grin and opens the door. “Don't be a pain in my ass, I won't be a pain in yours... unless you ask me nicely.” He winks, disappearing back to the cafeteria.
Dean gets up and goes to rinse his hands off, then heads to work. He nearly gets in another fight there, but Butcher breaks it up before it begins and by the time he’s sitting in the yard, he’s a little pent up again.
Luckily, he comes across some cards so he lays them out and stands up. “Who wants to get their ass kicked?”
Ashton, the dude who fucked up Jask’s face, comes to sit across from him and looks at the empty table. “Do you even have anything to bet with?”
“You'd be surprised,” Dean says, winking and clicking his tongue. He knows the effect that has on people and Ashton proves to be no exception.
He leans forward and bites his lip. “Which part of your cocky little ass are you offering up, then?”
Dean purses his lips in a pout, pretending to think about it. “How about a blowey in the laundry room, and I want... pack a cigs?
“You're serious? You think your mouth is worth an entire damn pack?” Ashton raises his eyebrows, but doesn't give him a chance to answer. “Fine, deal me in. You're hot enough that I don't care if you suck at it.”
“Suck at suckin’?” Dean leans in. “My mouth is worth ten packs, Ashy boy. Ask around.”
“Funny, the only one I've heard saying a word about your mouth is Ishim, and he says it wasn't that great.” Ash taps the table. “Deal, pretty boy.”
“Yeah he would. You think I gave a creep like that top shelf? Dumber than you look, Ash.” Dean deals, watching his facial expressions and decides to keep him distracted. “Why you hittin’ on my roomie, anyway?”
“ Hitting, not hitting on. And why does anyone do anything around here? I was paid to.” Ash stares at the cards in his hand, and his face gives away how shitty it is. “And no, I'm not telling you who did it. I'm pretty sure they didn't get what they wanted out of it.”
Dean rolls his eyes. “Hittin’ on is hittin’, Ash. I didn’t think he was your type, anyway. How about you do yourself a favor and fold now.” Dean flashes a smile. “Also, about your friend Ishim, what else he tell you, huh? He tell you he came in twenty seconds?”
“No, he didn't tell me anything, and he's not my friend.” He frowns when he swaps cards and his hand isn't any better. “Just heard rumors, that's all.”
“Mmhm... so who are your friends?” Dean asks, trying to make him slip about who paid him. He assumes what they wanted was Jask to have to get more time, but he just wants to know who.
Ashton doesn't answer for a long moment, then tosses his cards face down and stands up. “This is prison. No one has friends. Enjoy your cigs… and watch who you ask that many questions to, Winchester. It's not a good look.” He tosses the pack on the table and throws his hood over his head as he walks away, and though Dean tries to peek and see who he goes to, the fucker just goes back inside.
Dean makes a mental note to watch Ash, but not in an obvious way. He takes his cards and his new cigs and goes inside for lunch, and after trading a few cigs for snacks, Dean makes his way over by Frenchie and leans against the wall near him, munching on a Twinkie with a grin. “Want a bite?”
Frenchie tilts his head as he stares at the hickey he left on Dean’s neck. “Looks like I already took one, but if you're offering again..."
“Maybe I am.” Dean pops the rest in his mouth and leans in. “Kinda cravin’ a lil boeuf bourguignon, Frenchie. Taste much better than anything else in this joint.”
That earns him a satisfied hum and a chuckle. "Clever. Will you come quietly this time, or would you prefer to fist fight someone else first?"
“I’ll take door number two. Kinda feel like deckin’ someone before I get off. Then you can give me some soufflé.”
Frenchie outright laughs and playfully nudges him. “Fine, but leave my cafétéria. If you fight again on my watch, I will be ze one taking ze punishment.”
“Alright fine, door number one then. Who knows what room they’d throw me in. Same room, five mins?” Dean doesn’t wait for an answer, just walks out and goes to the room.
There's no way a full five go by before Frenchie follows him in, and the second the door shuts, he backs him toward the couch and falls backward onto it, pulling Dean with him and into a kiss.
Dean straddles him and smiles into the kiss, rutting his rapidly hardening cock against the guard. “Gonna give me that dick forreal this time, or you gonna make a guy beg?”
“Lock ze door. Take off that ridiculous jumpsuit and come 'ere.” Frenchie pushes him off and struggles with his own pants for a moment, but gets them down around his knees.
Dean locks the door and walks back, stripping for Frenchie with a cocky grin and gripping his boner, getting a better look at him this time. “Kinda hot, Frenchie.”
“Kind of? You really know how to turn a guy on, Weenchester.” He grins at the face Dean makes and fishes a small bottle of lube out of his pocket, then slicks his cock. “Bring that beautiful ass back to me.”
Chuckling, Dean straddles him again. “How about I show you how hot I think you are.”
“That’ll do.” He teases Dean's hole and slides a finger in, quickly working up to two as his other hand travels up Dean's body. “And you're the beautiful one.”
“Butterin’ me up, huh? Knew the French loved butter.” Dean grins, reaching back to move his hand. “I'm good. I like feelin’ it.” He lines up and sinks down, groaning at the burn and not stopping until he bottoms out.
Frenchie's eyes slam closed as he rocks up, bringing his messy hand around to stroke Dean's cock. He starts muttering in French, and it's hot as hell so Dean starts bouncing, staring down and watching him come unglued. “Feel good, French? You like this ass?”
“Oui,” he grunts, planting his feet on the couch and slamming up as he strokes Dean faster. “Ahhhh, shit… I could die in this ass and be happy.”
“Yeah... say that in French, baby.”
“Je pourrais mourir dans ce cul et être heureux!” He bites his lip and lets go of Dean's cock, grabbing both hips and pulling him flush as he grinds up, burying himself as deep as he can go.
His cock finds Dean prostate and he tosses his head back with a groan as his cock rubs on Frenchie’s stomach. “Fuck... I’m gonna—”
“Donne le moi.” Frenchie fucks up harder, groaning with the effort it's taking not to come first.
Dean grips the couch and releases, moaning Frenchie’s name with a sinful growl and getting it all up his shirt, clear to his chest. The rush of hot come fills him at the same time, and he’s pulled down into a heated kiss as Frenchie slows his movements. Dean rolls his hips through it, stopping after a few moments and then sitting up to roll off and get cleaned up. “Best fuck i’ve had in a year, hands down.”
Frenchie chuckles. “I could say ze same. Maybe even two years. Maybe three.” He catches his breath and gets up, wiping some of the mess from his shirt and then fixing his pants. “You should go before you get caught.”
“Alright. Thanks again. Always a good time in France.” Dean kisses him and makes his way back to his room, ready for a nap.
As he lays down and covers his head with the pillow to block out the light, he smiles to himself. If things stay good with Frenchie, he may not need anyone else at all to help him get through this.
He's got this.