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“Good morning,” Dean purrs, mouth playing along the line of Sam’s jaw.

Sam grins, stretching as best he can on the prison bunk. “Good morning to you, too. You’re up early.”

“New cellmate today,” Dean reminds him, one hand playing under the hem of Sam’s undershirt.

“Give him time to adjust before breaking him in.” Sam brings his arms down to encircle Dean’s shoulders, like they could possibly get any closer.

Dean pouts at that. “You’re no fun.”

Sam just smiles and rolls them over, fitting himself between Dean’s thighs. “I’m plenty of fun. Let me show you.”


Jack Kline is the youngest addition to the prison in a long time and he had a rough couple days before Sam really paid him any mind. The kid is tough, despite his innocent looks, and he’s held his own well enough. He looks so young and sweet, though. Sam just wants to bundle him away from the world and keep him safe.

Dean took some persuading, but they’ve been down a proper third for a few months- really, Fergus shouldn’t have tried to betray them like that- and he’s itching for young blood. Sam rides Dean’s cock one night, hunched over to whisper all the dirty, filthy things they can do to Jack, and Dean quickly changes his mind. With both Winchesters on board, the Warden had no other option and the paperwork was filed for the cell transfer.

When Jack enters their cell, he appears torn between genuine fear and a determination Sam finds admirable.

“Hello,” Sam coos, backing Jack up against a wall and taking his possessions. “I’m Sam. That’s my brother, Dean.”

“I know who you are,” Jack says, glaring defiantly up at him.

“That’s good. You’ll have the top bunk.” Sam hands Jack’s things off to Dean, who places them on the designated mattress. “Dean and I share the bottom bunk. If you would like to, you’re welcome to join us.”

Surprise flicker’s across Jack’s face before he can suppress it. “What?”

Sam brushes the back of his hand against Jack’s cheek, frowning. “Poor boy. Did you expect us to rape you?”

The nod is almost minuscule. If Sam weren’t standing so close, he might’ve missed it.

Dean makes a disgusted sound and Jack’s eyes snap to him. “No. Never. We might be the kings of this prison, but all of our partners come willingly.”

“Rape is not tolerated here,” Sam continues. “Did someone try to touch you?”

“There was a man, in the showers,” Jack says, the slight tremble in his voice betraying how much this incident really shook him up. “But someone else stepped in and stopped him.”

“Who?” Dean almost growls, moving in to stand behind Jack, like he can protect the boy from everything with his body alone- he probably could.

“I don’t know,” Jack admits. He’s hugging himself now, shrinking a bit between the two men, and Sam realizes how small he is. “I think someone called him Walker?”

“Gordon,” Sam spits. “Why am I not surprised. Don’t worry, baby. He won’t come near you ever again.”

“You’ll protect me?” Jack’s eyes are wide. “And you don’t expect anything in return?”

“Of course not,” Sam assures him. “This cell is a safe space. Everyone knows that whoever shares our cell will be under our protection forever.”

“Why me?” The boy looks back and forth at them both. “You don’t know me.”

“No,” Dean agrees. “But we would like to know you, even if you never come to our bed.”

“What if… I want to come to your bed?”

Sam grins, turning his hand to cup Jack’s jaw. “Do you want that?”

“I want to try it,” Jack says.

“If you need to stop, tell us,” Dean says, his own hand sliding around Jack’s waist.

“I will, I promise.”

Sam leans down until his nose bumps against Jack’s. “May I kiss you?”

Jack’s response is more a breath than a word. “Yes.”

His lips are smooth and soft against Sam’s, yielding easily to the kiss. His body arches into Sam’s, hands crawling around the bigger man’s middle. He’s so tiny in Sam’s arms, tiny and perfect in all the best ways.

Reluctantly, Sam breaks the kiss. Jack is flushed, mouth hanging open in a daze, and his interest can be felt where their bodies are pressed tight. Sam chuckles and rubs his thumb against Jack’s lower lip.

“Good?” he asks.

Jack manages a nod.

“Would you like Dean to have a turn?”

The man in question is waiting patiently behind Jack for his turn. Jack twists around, offering himself up to Dean.

“Ask him nicely,” Sam encourages, shooting his brother a knowing grin.

“Please, Dean,” Jack says, voice sweet in the most tempting way. “Will you kiss me?”

“Fuck, baby,” Dean growls, tugging Jack in tight against him. “Want me to kiss you?”

“Please,” Jack repeats.

Sam loves watching Dean kiss, regardless of the partner, and Jack is far from disappointing. Jack molds himself to Dean’s chest, fingers curling into orange jumpsuit, and gives as good as he’s getting. It’s like he can sense that Sam is really the one in charge here.

“Beautiful,” Sam praises when they break apart.

“Yeah?” Jack is smiling. He tucks his head into the curve of Dean’s shoulder, fitting in like he belongs right there. Sam is beginning to think he does. “Can we do more?”

“You want more?” Sam hadn’t expected things to move this quickly.

“I’m not a blushing virgin,” Jack informs them. “Just never been with two men at the same time, let alone two men… like you.” He does blush at that. “But I want to do this.”

Dean’s hand slips down to grip Jack’s ass. “We’ll take good care of you, sweetheart, but I think we should wait until tonight.”

Sam nods. “Make it special. Let us wine and dine you a little before we fuck your brains out.”

Jack’s laugh is the purest thing Sam’s ever heard. “I can wait for that.”


Wining and dining in prison isn’t much- Sam can’t wait until they’re out; he wants to take Jack to a high-end restaurant and treat him like a prince- but the Winchesters do their best. They pull some strings and get Jack a soda to go with his dinner, as well as fresh bread and butter. Jack blushes and ducks his head. The meal gets some whispers from other inmates, but a glare from Sam or Dean is more than enough to shut them up and Jack seems much more confident by the end of the meal. He even holds Dean’s hand on top of the table.

Finally, it’s time to return to their cell for the night. Everyone files back into the cell blocks. Some nights Sam hates being shut up like this, but tonight he doesn’t mind. As soon as the door latches shut, Jack turns and tugs him down into a fierce kiss.

“You promised me something,” Jack reminds them, grinding his hips against Sam’s thigh. His interest is clear.

“We did, didn’t we?” Sam curls his arm around Jack’s waist and nuzzles under his jaw. “Gonna make you feel so good, sweetheart.”

Dean moves in behind, an echo of their positions from earlier, and his hands immediately begin to free Jack of that unflattering orange jumpsuit. Once that’s gone, Dean moves on to his own clothes and allows Jack to focus on Sam’s. When they’re all down to boxers and socks, Sam steers Jack over to where Dean is pulling the mattress off the top bunk.

“The downside of being as big as us,” Sam chuckles in Jack’s ear, “is those beds. Gets a bit squishy.”

“I can imagine.” Jack stretches up to nibble along the line of Sam’s throat.

“Gonna mark me up?” Sam asks.

Jack immediately retreats. “Is that not…?”

“No, no, it’s okay,” Sam assures him. “I like it. We want to mark you up plenty, it’s only fair you return the favor.”

Teeth find the edge of his collarbone. Jack bites and sucks until he’s satisfied there, only to move lower on Sam’s chest. He tugs Sam’s shirt collar down to get at the smooth skin of his pec and digs his teeth in. Sam grunts, but the pain is a good one.

“Already discovering kinks,” Dean teases, gripping Jack’s hair and pulling his head back. He’s gentle, but Jack still gasps and his hips still stutter against Sam’s thigh. “Oh, someone likes that.”

“Please,” Jack breathes, slender fingers digging into Sam’s biceps.

“Please what?” Dean questions, tugging Jack away from Sam so he can begin exploring the boy’s body with his free hand. “What do you want, baby?”

“Anything, everything,” Jack sputters.

Dean mouths at the side of Jack’s neck before guiding him over to kneel on the mattress. Jack goes willingly. The position puts his head at the right height with Dean’s hips and he immediately takes advantage of this. His fingers find the waistband of Dean’s boxers, pulling them down and off.

“Eager,” Sam observes, kneeling behind Jack. He curls his fingers around Jack’s hips, watching as small hands encircle Dean’s cock. “Gonna suck it?”

Jack is already moving, wrapping candy pink lips around the head. Dean moans and Jack blinks up at him, impossibly innocent even as he takes Dean’s cock deeper.

“So perfect,” Sam praises, letting his fingers quest under the waistband of Jack’s boxers. He finds soft skin and a tight ass, and then a rapidly hardening cock he quickly wraps his hand around. “I want to fuck you.”

Jack groans, the sound muffled by Dean’s cock, and nods. Dean cups his head in one hand and gently pulls him away.

“Gonna make me cum if you keep that up,” he says when Jack pouts. “Lay back, sweetheart, and let us take care of you.”

Jack goes easily, lying on his back and letting Sam strip him of his remaining clothes. His body is perfect, in Sam’s opinion, a balance of hard muscle and the softness of youth. He lets his legs fall open, baring him to the brothers.

“Look at that.” Dean slides his hand down one soft inner thigh to frame the base of Jack’s cock with his fingers. “Pretty baby.”

Jack blushes but doesn’t squirm or turn away. Sam moves in on the other side, leaning down to mouth and bite down the center of Jack’s chest before moving to one tight, dark nipple. Jack whines and arches into Sam’s mouth. Sam hums to himself and pulls at the peak with his teeth.

When Jack gasps, body trembling on the mattress, Sam glances down to see Dean deepthroating the boy’s cock. Sam grins and moves to the other nipple, giving it the same treatment as before.

Dean moves off the mattress of a bit but returns quickly. He sets a bottle of lube on Jack’s belly, settling between his spread thighs once more.

Sam reluctantly leaves Jack’s nipples to continue exploring his torso, moving down over his abs with careful nibbles and kisses. Dean has slicked his fingers up and is stroking Jack’s cock with one hand, the other out of sight beneath where he’s mouthing at Jack’s balls.

Jack tucks his knees up even more, one pressed against Sam’s side and the other held out of the way with his hand. “Dean, please,” he grunts. “Just do it.”

Dean chuckles. “We found ourselves a little cockslut, didn’t we? Hear that, Sammy? Baby wants my fingers in his ass.”

“Want more than that,” Jack retorts.

Sam laughs and lifts up to kiss him. “You’ll get more, sweetheart, don’t worry. But we don’t want to rush this.” He shuffles around to kneel over Jack’s head and curls his own hands around the back of Jack’s knees, holding him open as Dean presses a second finger inside. “Gotta make sure we take good care of you. Right?”

Jack nods, mouth hanging open a bit as he tries to roll his fingers down on Dean’s hand. Sam’s got him pinned, though, and he can’t do much with his lower body. He combats this by tugging down Sam’s boxers and sucking the hard cock that bobs free into his mouth. The position allows him to take Sam much deeper than he was able to take Dean’s earlier.

“Such a good little slut,” Sam comments, watching where his cock vanishes between pretty lips. “Look at you, taking the initiative. Told you he would be good at this.” Sam shoots Dean a grin.

“Yeah, yeah,” Dean grumbles without any real heat. He’s got three fingers now- when that happened, Sam’s not sure. “You want first go at his hole?”

Sam shakes his head, pulling his hips back. Jack pouts when he loses access to Sam’s cock.

“Is it okay if Dean fucks you first?” Sam asks, releasing one knee to he can rub at spit-slick lips with his thumb. “I think it would be better. He can work you open, and then I can have his sloppy seconds.” He winks and Jack’s cock jumps against his belly.

“Yes, please,” Jack agrees. “I want that.”

“Good.” Dean pulls his fingers free and sits up, slicking his cock. “Put your legs around my waist, baby.” Sam lets go so Jack can follow Dean’s instructions. “There you go.”

The first push in has Jack’s head falling back, eyes squeezed shut and mouth open in a noiseless cry. His heels dig into Dean’s ass, driving him onward when he tries to stop. Finally their hips are pressed together and Jack inhales.

“You okay?” Dean asks, rubbing one hand against Jack’s pelvis.

“Move,” Jack grits out.

Sam laughs as Dean does just that, pulling out and driving back in, yanking his shirt off as he goes. Jack grunts and grips at Sam’s hip, pulling him down so Jack can get his mouth on Sam’s cock once more. Sam braces himself against Dean, their faces close enough for some kissing. It’s their first physical interaction tonight and it’s nice, familiar. Sam loves the reassurance of something as simple as a kiss, knowing his brother and other half is right here with him in this.

“He’s tight as hell,” Dean murmurs, bumping their noses together. “Can’t wait to watch you have at him.”

“I’m thinking of having him ride me,” Sam says, feeling Jack groan at those words. “But it would be nice to put him on all fours.”

“Bet he’s a noisy bottom when his mouth isn’t full.” Dean kisses Sam again before sitting back and giving a particularly brutal thrust that has Jack whimpering.

Sam is inclined to agree. “Can’t wait to hear that.” He settles back on his knees, leaving on the head of his cock within reach of Jack’s mouth. “What do you think, sweetheart?”

Jack just moans, eyelids fluttering as his tongue teases Sam’s slit. Sam traces the shape of his cock through Jack’s cheek, shifting his hips forward to press a little deeper. He’s careful not to go too deep, he doesn’t want to choke Jack. Having been on the receiving end of that once or twice in the past, he knows isn’t always as fun as pornos like to make it look.

Dean is rocking steadily into Jack’s body, hands busy exploring all the little sweet spots that make Jack wriggle on the mattress. He finds those tight little nipples that have the boy arching and crying out.

“Fuck,” Dean grunts. “Like that, do you? That made you clench up.” He plucks at one nipple and then the other, and Sam bites his lips at the sounds vibrating through his cock. “Wonder if you could come just from us playing with your nipples? We’ll have to try that later.”

How Dean’s still talking, Sam has no clue, because he can tell from the stutter of his hips that Dean is very close. Sure enough, a few more thrusts and Dean slams in with a final shout. His whole body shakes and shudders, and Jack sighs contentedly as he’s filled.

“Perfect,” Sam praises, leaning in to kiss Dean through his aftershocks. “So good. My turn now.”

Dean pulls out, shifting to sit beside Jack. Sam stands, strips, and moves around to kneel between Jack’s legs. He pets the soft skin of Jack’s inner thighs, watching Dean’s cum drip from his hole.

“Do you want me like this?” Sam asks, taking Jack’s cock in one hand and just holding it.

Jack shakes his head, already moving. He rolls onto his belly and lifts up on his knees, presenting his ass for Sam’s hungry hands. “Like this,” he says, pillowing his head on his folded arms.

Sam groans and wastes no time shoving in. Jack opens up to the intrusion with a wail that the other inmates definitely heard.

“Yeah, fuck him good!” someone shouts from further down the row.

“Shut the hell up,” Dean snaps back.

Jack is blushing, hiding his face in his arms and biting back sounds as Sam fucks him.

“Hey, hey,” Sam murmurs, leaning in to blanket Jack’s back with his body. “Don’t listen to them. I want to hear all your pretty little sounds, sweetheart. Don’t hold back. They’re just jealous.”

Jack turns his head, glancing back at Sam. “You’re so big.”

Sam chuckles, petting Jack’s sides soothingly. “Yeah, I’ve heard that. Part of why we had Dean go first, to help you relax a little. Are you feeling okay?”

“Need your to fuck me good and hard,” Jack replies.

That’s all the encouragement Sam needs. He settles back, bracing himself with his hands on Jack’s hips, and get to work. Each thrust punches a sound from Jack’s lungs that makes Sam’s balls throb where they’re knocking against the boy’s. He loves the way Jack arches his back, pushing his ass up so Sam can get deeper.

Sam reaches around to wrap his hand around Jack’s cock, stroking him in time with each thrust. In no time, Jack is wailing and shaking apart, spilling all over Sam’s hand and the mattress. The clench of his body is enough to push Sam over his own edge and he cums with a growl, free hand pressing Jack’s shoulders into the mattress.

Once the aftershocks have faded, Sam carefully pulls out. The sight of his cum, mixed with Dean’s, leaking from Jack’s hole is enough to make his cock twitch. He pushes the dribbles back in the best he can, wishing he had a plug to keep it all trapped.

Jack is trembling and Sam gently lowers him to the mattress, letting him stretch out fully for the first time tonight. “Good boy,” he murmurs, stroking Jack’s back and thighs. “You were so good for us tonight.”

“Yeah?” Jack says with a sleepy grin.

Sam enlists Dean’s help in getting Jack to sit and then stand. They wipe him down with someone’s t-shirt and then somehow get all three of them into the lower bunk. It’s squishy, but Dean puts the blanket over himself, tucking Jack into his front, and lets Sam slip under the blanket from the other side. Their legs tangle together, Jack’s head on Dean’s chest, and the tight fit works. Sam likes having both Jack and Dean this close. He sleeps easily with them there.


The next morning, Jack finds himself alone in the showers for a few minutes. He knows Sam and Dean will be in soon, though, so he gets comfortable beneath warm water. He’s never felt more relaxed, having finished a sort of three-way 69 with the Winchesters, and he hums softly as he wets his hair.

A huge, hard body shoves him up against the cold tile wall, pinning him in place by pure size alone. Jack opens his mouth to shout, but a hand covers it.

“Heard you last night with the Winchesters,” a voice growls, and Jack recognizes the man Sam called Gordon last night. A hard, slick cock slides between his ass cheeks.  “Sounded like a professional bitch taking Sam’s cock. Wonder what you’ll sound like on mine.”

Just as suddenly as the weight of Gordon’s body arrived, it’s gone. Jack presses himself tight against the wall, squeezing his eyes shut at the sound of at least two people fighting behind him. Someone goes down with a grunt and Jack hears Dean snarling threats as the guards arrive.

Hands settle on Jack’s shoulders and he flinches away, trying to make himself as small as he can.

“Hey, hey.” Sam’s voice is low and soothing as he gently pulls Jack into his arms. “I’ve got you, it’s just me. C’mere, sweetheart.” He tucks Jack in, surrounding him with the warm strength of his body. “It’s okay, he’s gone.”

Dean appears, falling in on Jack’s other side. He pets Jack’s hair and shoulders. “Are you okay?” he asks, body joining Sam’s in shielding Jack from the curious eyes of the other occupants of the shower room.

“I… I’m okay,” Jack stammers. “He didn’t do anything but… touch. And talk.”

“Touching is bad enough,” Sam sighs. “I’m sorry, baby. We shouldn’t have left you alone. I thought the threat of getting on our bad side would be enough, but apparently not. He won’t come near you again, I can promise you that.”

Jack nods, rubbing his nose along Sam’s collarbone.

“C’mon, let’s get you cleaned up,” Dean suggests. “A shower and then breakfast. How does that sound?” He brushes Jack’s hair off his forehead. “Sound okay?”

“Okay,” Jack murmurs. He turns his head, stretching up to catch Dean’s lips in a kiss. “Or you could show everyone else who I belong to?”

Dean’s eyes darken immediately at that and Sam’s arm tightens around Jack’s waist.

“You want that?” Sam asks, hand sliding down to grip Jack’s ass.

Jack grins up at him. “All we need is lube.”

Lucky for them, the fancy conditioner Sam has brought in from the outside works perfectly.