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Dean is Sam’s.
There’s no other way to put it, no single word that can possibly encapsulate the relationship they have with one another. Dean- Dean who can charm the habit off a nun when he’s with others but who stays quiet when Sam doesn’t give him permission, who listens and learns and does- is Sam’s brother, his lover, his property, and there isn't any argument about this fact. That's what it is- indisputable and tangible. Dean is Sam's, and there's nothing that's ever going to change that. It's about more than ownership, however, and both of them are well aware of it.
It's about having someone to fall back on, someone to hold and to protect without any stigma attached, and while in public they come off as a pair of relatively normal brothers, what they do behind closed doors is something entirely different. Dean, who's been the one in control since they were boys, the one in charge, the one who took it upon himself to take care of Sam and raise him almost as if his brother was his own, likes relinquishing that power and Sam likes taking it up again.
So their relationship evolved from brothers to lovers to more, to a partnership that's all about trust while heavily outweighing equality. Sam enjoys seeing his older brother lose himself, likes to see Dean at his most vulnerable, and letting go is all Dean has ever wanted. So while their relationship isn't something most people consider normal- or even healthy- they enjoy it. It's the only thing that's ever truly brought them together, deeper than flesh and soul and mind.
Sam says and Dean listens.
It's the way it works around their house. If Sam doesn't want to speak, Dean isn't allowed to, either. Sam dictates where Dean goes, what he wears and if he leaves, and it works better this way. In public, Dean is the one in charge. Loud, abrasive, less than adept in social situations but still gifted with an innate charisma that works on his side, he takes control of conversations. Sam, though, is the one holding the leash, and if Dean strays too far or says something Sam doesn't like, he tugs on it.
There's the time they fucked in the bathroom at an office party, the night Sam left Dean's ass bruised and raw and striped with dark blue welts raised on his skin and tears stinging his eyes for days afterwards whenever he attempted to sit down. Humiliation is part of their game, part of the thing that makes them work, and if Dean is left in a position where he can't snark or snap or talk back, Sam's done his job well.
And then he meets Castiel and his entire world is thrown for a loop.
Castiel is dark-haired, slim and intriguing with eyes the colour of the ocean and pale skin, and while he's soft-spoken, he commands attention. He's smart and he's fast and a little naive, and Sam is interested. Dean- who meets Castiel when Sam brings him home for a business meeting- is interested as well. The businessman with the penchant for skinny ties and khaki coats is worming into them the way neither of them can for each other, and it's creating a rift.
Sam notices it one night over dinner, Dean quiet across the table from him but looking slightly more thoughtful than usual. "What are you doing?" Sam asks, and Dean looks at him. The flicker of something in his eyes makes Sam uncertain for a moment, something he hasn't felt in years.
"Thinking," Dean says, and it isn't the answer Sam was looking for. Dean knows it, too, the corner of his mouth twisting upward into a half-smile, and Sam continues to look at him, almost expectant. "About Castiel," Dean finally says, and Sam licks his lips.
This ought to be good. Castiel's been over a few times by now, Sam trying to work out a business deal with him. It's something that would benefit them all, but there's no earthly reason why Dean should be interested. "Are you getting bored?" Sam asks, and he manages to keep the tone of incredulity out of his voice. That's no good.
"No." There's enough honesty in Dean's eyes to convince Sam that he's telling the truth. "I'm not."
"We can't bring in a third person," Sam says.
Dean nods. "I know."
There's a moment's pause, a silence so pregnant with unsaid things that Sam feels like he could pop it with a pin. He gets to his feet after a moment, looking at Dean for a few seconds and trying to think. He wants to keep Dean. He wants to keep him for as long as he can until they have to stop pretending, stop acting like they aren't brothers and they aren't living out their lives in a bubble, a place where people can't permeate. They both know it's going to happen soon enough, and putting it off isn't going to help.
But it isn't going to hurt either, and Sam mulls this over before holding out his hand. "I want to take a bath."
Dean shrugs, standing up and twisting his fingers together with his brother's, letting Sam lead him upstairs. It doesn't take long for the two of them to sink into the tub, the hot water more than a little relaxing, and Dean is content with leaning against Sam for a while until Sam slides calloused fingers up his legs. Dean parts his lips, lets Sam do what he wants because that's all he's known for the last few years, and Sam leans in close, his teeth worrying Dean's earlobe for a moment before he murmurs, "I think I have an idea for you."
Dean just looks at him for a moment, biting back the urge to say something in return and staying quiet instead. Sam continues to touch Dean's legs, fingers exploring every inch of the skin before he comes to a stop on Dean's hips. "You have to shave, though."
"Excuse me?" Dean says it without thinking and earns a hard pinch on the ass, groaning slightly but knowing better than to try and twist away.
"Shave. You're going to have to shave. Your legs. Your face. Your stomach." Sam's fingers trace down the line of hair on his brother's abdomen, coming to rest right above his cock. "Here, too."
"Sam."
"It's not an option, Dean." Sam slides his hand past his brother, lifting the razor he uses to shave off the side of the tub and leaning in slightly. "I'll shave you if you don't want to do it."
"Why?"
"Because I want to."
Dean doesn't argue despite wanting to, frowning slightly instead and getting to his feet. He steps out of the bath and retrieves the shaving cream from the cupboard beneath the sink before slipping back into the bath with Sam, his brother kissing him on the neck before lathering Dean's face with the cream. "Trust me," Sam says lowly, and Dean does. He always does.
---
It takes a few days to get used to being clean-shaven. His legs prickle slightly but Sam takes care of it, touching up the areas that need it and paying special attention to the now-bare areas around his cock. "Maybe we should get your ass bleached," Sam teases every now and again after their first experience with shaving, but Dean is pretty sure the thought has crossed Sam's mind in a serious capacity more than once. If his brother tries to force the issue, Dean's pretty sure he'll have to refuse.
Once Dean's accustomed to the feeling, to maintaining his smooth legs and stomach, Sam comes home with a suitcase full of things. He doesn't tell Dean what's in it and Dean knows better than to look, no matter how much his curiosity wants to get the better of him. He keeps his mouth shut and Sam doesn't tell him until they're laying in bed that night, Dean already half-asleep against the pillows. When Sam unzips the bag, though, Dean wakes up immediately. "No," he says after a moment, and Sam hits him in the chest, hard enough to sting but not really do much else.
Sam pulls out makeup, a wig and a few outfits, along with a couple pairs of shoes, and Dean swallows, staring at the articles set out before him. He doesn't like this. He's worn women's underwear before on rare occasions but this... this is asking too much. There's no way he can do it. Sam, however, ignores whatever expression Dean is currently making and lifts one of the wigs, eyeing the blond affair before slipping it on Dean. "It suits you," he says, and Dean just stares.
"Why?" he asks, and while it's the second time in less than a week that he's questioned his brother's motives, Sam doesn't call him out on it.
"Because you're mine. Look, if you don't want it, then you know the safe word." Dean glances at Sam, who's watching him almost darkly, and decides that their safe word isn't a necessity. He adjusts the wig on his head and tries to force down the humiliation rising in his stomach. Sam smiles. "You look good."
---
Sam makes him wear the clothes, the girl's shoes and the makeup, and the first time Dean is fully dressed like a woman, Sam tugs him into the bathroom and forces Dean to stand in front of the mirror. Dean doesn't recognize the person looking back at him, a blonde-haired hazel-eyed girl in a tank top and short shorts, stiletto heels strapped to her feet. He feels a surge of uncertainty, an almost overwhelming moment of what can only be described as self-loathing, and for a moment he considers going against Sam.
At the same time, however, his cock hardens, pressing against the tight denim of the shorts. Sam slips one of his hands down over the bulge in Dean's shorts, his finger slipping across the length of the shaft slowly. Dean groans, leans into Sam's touch, and Sam nuzzles into his neck, kissing the freckled skin there gently. "Sam," Dean murmurs, and Sam undoes the top button on the shorts.
"What should I call you?" Sam asks after a moment, his fingers poised on the bare skin just above Dean's throbbing prick. "You need a name."
"It's just Dean."
"No." Dean knows what's coming next. "How about Deanna?"
Terror floods through Dean's veins. He isn't frightened of Sam, but of losing his brother. He's scared that Sam doesn't want him, wants a girl instead, and that isn't something he's ever going to find in Dean. Dean's tongue darts out, licks at his lips coated with candy apple red lipstick, and hits his brother in the face. "Colt," he says, practically spitting their safe word at him before tugging off the tank top and the wig. Dean catches sight of himself in the mirror, rubs fruitlessly at the mascara adorning his eyes, and storms out of the bathroom.
He's less angry about the crossdressing and more angry about what it might mean.
---
It takes Sam a few days to coax Dean back to bed, to rebuild their repertoire, and even when he does, things aren't the same. Dean doesn't want to give in, wants to stay mad at Sam and what Sam did to him, but soft words and fingers sliding up his spine are enough to get him to bend, if only just a little. "I'm sorry," Sam murmurs on a Saturday afternoon, the two of them tangled together in their bed. "I don't want to replace you."
"What the fuck ever."
"I don't." Sam sits up slightly, still holding onto Dean. "I thought you'd like it. That we'd like it."
"Why would I like it?"
"Because I want you to."
Coming from anyone else, that excuse would be laughable. But Dean likes to see Sam happy, likes to do things for him he wouldn't do for anyone else, and if that entails dressing like a girl, he's probably going to do it. Dean pushes back his hesitation, his fear, his loathing, and rests his hands palms up on the bed, acquiescing to his brother. "Okay. We can try again."
Sam grins, leans in and kisses Dean on the mouth hard enough to leave his lips red. He tugs Dean in, slides his hands down over Dean's ass and lets them come to rest on his brother's legs lightly, nuzzling against him and pulling Dean into his lap. Dean, wearing on a pair of boxers, lets his brother touch him because it's what he needs to do, but his heart is pounding furiously in his chest and he feels a little dizzy.
He isn't a chick. He's one hundred percent sure he isn't a lady, doesn't like being called one or treated like one, and the idea of Sam wanting him to dress like a woman is humiliating because it isn't who he is. He swallows and allows Sam to trace the vein in his neck with his tongue, hoping he doesn't notice how fast his heart is racing.
----
Sam begins to expect things. He begins to expect to come home and find Dean made up, ready and waiting in a dress or leggings or whatever outfit Sam picked out for him that day. He stops expecting Dean to be himself, starts anticipating Deanna to be standing in the kitchen waiting for him, all blonde hair and rouged lips, and Dean is beginning to lose himself in an identity he never, ever wanted in the first place.
It's humiliating in a way nothing else has ever been, having Sam call him slut or bitch or Deanna when they're in bed together, and Dean is starting to hate it. He hates the dresses, the sticky feel of mascara when he's had it on for too long and the way he finds himself checking that he looks presentable. He dreads the times he's alone in the house, given the opportunity to go back to being Dean, because he knows that if Sam found out he hadn't spent the day in the clothes he'd picked out, there'd be hell to pay.
At the same time, though, he likes it. He'll never admit it- hell, he might not even know he likes it in the first place- but this is the ultimate humiliation, the epitome of a torture Dean never really knew he wanted, and as much as he's fighting with his masculinity, he puts up with it. He lets Sam do what he wants because he trusts him, even if he doesn't particularly enjoy it.
Sam comes home one day with a drycleaning bag, setting it on the kitchen table and looking at Dean intently. "I bought you something," he says simply, and Dean, who's been given a rare day off from pretending he's someone else, looks at him.
"What?"
"Open it."
Dean frowns and unzips the bag, tugging out a maid uniform. It's the kind he's seen in pornos and on girls at Halloween and he swallows, biting back his discomfort and instead turning his gaze on his brother. "Sam." The thing is all black lace and white frills, with only two thin spaghetti straps at the top and a skirt so short he's sure his ass will be visible. It comes with thigh-high stockings and a garter, along with straps, and Sam grins at him before pushing another box at him.
"It comes with panties," he says simply, and Dean opens the box to find a pair of lacy underwear, not quite boy shorts but close enough, and he tries to look pleased about it. There are shoes, too, heels that look uncomfortably high, and Dean feels vaguely upset by this point.
"Do you like it?" Sam asks, and his tone makes it clear what he expects the answer to be.
"Yeah," Dean says, and he manages to smile. Sam leans forward and kisses him and while it relaxes Dean in the slightest, it isn't enough.
"I have a meeting with Castiel tonight," Sam says, Dean nodding in response. "I'll be back around midnight. I want you wearing that." He presses his mouth to Dean's ear, kissing along the sensitive flesh gently. "I want to fuck you tonight."
"Okay."
Sam smiles and pulls back, waving before heading out the front door. Dean looks down at the outfit in front of him and steels his resolve. This is something he has to do.
----
Castiel can hold his alcohol like a champ. Sam's mildly surprised by this- he'd never taken Castiel for much more than a lightweight- but it's amusing in a way he hadn't expected. They're on their fifth drinks of the night, holed up in the corner of some ritzy bar in the heart of downtown, and while this began as a meeting, it's ending as a celebration. After months, they've reached a deal for their business partnership, and Sam hopes it's the beginning of a good friendship.
"You know," Castiel says after a moment, leaning forward. His words are slightly slurred. "I think people put too much stock in relationships."
Sam, who's been in the same relationship since he was eighteen, wrinkles his forehead but nods anyway. "You're right." Castiel's wrong, but telling him that won't accomplish anything.
"I mean..." He pauses, searching for the right word. "I'm a virgin," he finally admits, and Sam's eyes widen before he can stop himself. "Kind of," Castiel clarifies. "I... I've had women."
"Oh."
"I don't want women."
"Oh." Sam wasn't really anticipating this turning into a coming out experience, but now that it's taken that rather unfortunate path, his mind starts to click into place. He knows what it is he wants, and he knows how he can get it. He likes Castiel. Castiel is new and exciting and Sam wonders how he'd look in the midst of sex, head thrown back and sweat beading on his brow. Dean's attracted to him, too- Sam knows it even if Dean doesn't want to admit it- and this could be perfect. "You sure you don't want women?" he asks after a moment, and Castiel cocks an eyebrow at him.
"Why?"
"I have one that's more your speed," Sam says, gesturing for the tab. He might as well have a little fun.
----
Dean sits on the stairs of their house, the uniform on, the skirt bunched up under his ass. The panties are way more comfortable than they should be, tight enough to create a sort of pressure against his cock that's kept him in a state of half-arousal for the entire evening. The heels are hard to walk in but Dean manages, and all-in-all, it isn't the worst outfit Sam's made him wear.
He looks like a woman from head to toe, blonde wig pinned up into a messy bun, and although he's no makeup expert, he does all right. He certainly doesn't look like he's been wearing makeup for too long, however, his mascara sloppily applied, his lipstick not quite perfect, but as far as he's concerned, it's good enough. These times when Sam is gone, when Dean is left alone in their house and forced to think about thinks he's never really sure he wants to confront... they're always the worst.
Dean is losing himself. He feels more like a girl every day, knows that Sam wants him to be one, and it's simultaneously scary and confusing. He's always been a guy, always identified as nothing but a guy, but he can only take dressing like a woman for so long before his mind begins to believe that it's something he genuinely wants to do. Dean is starting to feel a little trapped.
He smooths down the front of his skirt, checks that his shoes are on correctly, and continues to wait for Sam to come home. It shouldn't be long now, and he wants to be ready. Dean isn't sure if he wants to be ready to get fucked or ready to tell Sam he doesn't want to do this, but he looks up once the lock clicks nonetheless, sliding off the stairs and getting to his feet. Sam walks in and Dean starts to greet him before spotting Castiel, the slimmer man holding onto Sam's arm. Dean immediately swallows, looking at his brother. "Hi."
Sam presses a finger to his mouth and it's clear from the look in his eyes that he doesn't want Dean to give anything away. It seems like a cruel thing to do to a man who's been nothing but great to him since they first met, but Dean has a streak in him somewhere, something that wants to fuck someone aside from his brother, and if he's going to be dressed as a woman, he's going to take advantage of it.
Castiel catches sight of Dean and he looks vaguely confused for a few moments before glancing over at Sam, his lips turned up in a slightly confused smile. "Who's this?"
"My girl," Sam says, not bothering to look at Dean when he says it. Dean- who's growing more and more accustomed to his brother addressing him as the opposite sex- simply nods and holds out one hand. If Sam is going to bring another man into this relationship, Dean's going to make him welcome. "You'll like her."
Castiel looks uncertain, almost scared, and Dean takes a step forward, grasping one of Castiel's hands with his own. With a nod from Sam, he starts to lead Castiel upstairs, teeth clenched as he tries his damnedest to keep calm. He's kind of a little fucking ticked off at his little brother right now. He leads Castiel to the bedroom he shares with Sam anyway, Sam following the two of them quietly, and once they're inside, Sam closes the door behind them all. "Go ahead," Sam says lowly, placing a less than chaste kiss to the nape of Castiel's neck. "I don't care."
It stings in a way Dean wasn't expecting it to, his eyes darting to Sam's after a moment of contemplation, and he takes Castiel's face in his hands, leaning in and kissing him hard on the mouth. If Sam wants a show, he'll get a damn show, just as long as he understands they aren't going to fucking do this again without Dean already being in on it. They might not even do it a second time, depending on how Castiel performs this time.
Castiel's mouth is hot against Dean's, his lips smoother than Sam's ever are, and Dean finds himself leaning into the kiss, eyes slipping closed. He slides his hands up Castiel's back, his fingers coming to rest on the other man's shoulderblades, and Castiel kisses back with such need, such desperation, that Dean's beginning to wonder exactly what it was that Sam told him to get him here. He opens one of his eyes to find Sam watching them, looking pensive, and Dean knows that he has some plan for all of this, although he isn't exactly sure what it is at this point.
Dragging his tongue over Castiel's lower lip, Dean moves one of his hands to Castiel's short black hair, keeping them crushed together as he kisses back harder than he intends to. He needs this, needs some justification that just because Sam is dressing him like a Barbie doll, he can't still enjoy sex, enjoy his body and everything that comes along with it. Castiel moans lowly in the back of his throat, his fingers sliding over the front of Dean's maid uniform and coming to a rest on Dean's hips.
He's going to notice soon enough. Dean's cock is hard, pressing against the front of the panties almost painfully, and he can already feel the precome beading at the tip, slicking up his lower stomach. Castiel has to notice. At the moment, however, Castiel seems more intent on kissing Dean, tasting every inch of his mouth, and Dean's only too happy to oblige. He curls his tongue against Castiel's, sucking slightly and eliciting another low groan from the other man. If these small touches can get him making noises like that, Dean wonders what else he can do.
It's nice to have someone aside from Sam to please for once, and although Dean knows that what he's doing is something his brother wants, it's something he wants, too, despite how he's dressed and how he's been made to act lately. There's a sudden surge of heat in his stomach, a roiling coil of desire, and Dean realizes that he's going to be humiliated. Castiel's going to figure out he's a guy, see his cock and the state he's in, and Dean isn't sure if that thought turns him on or leaves him more confused than ever.
"Touch her," Sam says, and Castiel breaks the kiss in order to look over at Sam. Castiel's clearly a little drunk, although sobriety is creeping in quickly. There's no way he's going to keep going if he sobers up all the way, so Dean understands Sam's need to have Castiel touch him already. He's waiting for Castiel to figure it out just as much as Dean is dreading it. "Come on, I don't mind. Touch her."
Castiel nods, looking back at Dean and furrowing his brow. He pushes Dean back slightly, forces him to sit down on the bed, and tugs off his tie before climbing on top of Dean, capturing his lips again in another, deeper kiss. Dean arches up into Castiel slightly and slides his arms around Castiel's neck, feels Castiel's fingers slip up his thighs and over his ass, and he doesn't try to keep it from happening as Castiel's hands find his underwear.
Castiel runs his fingers over the front of the panties and immediately stops, featherlight fingers resting on Dean's aching cock. He pulls back slightly, still on top of Dean, and looks down at him with an expression of utmost confusion. "Dean?"
Dean smiles despite the position he's in, cocking an eyebrow and looking over at his brother. Sam's grinning, looking utterly pleased with the fact that he managed to get Castiel back here and into the situation he's in now, and he walks over to the bed, sitting down next to the two of them. "I told you I had a girl you'd like."
"He's your brother," Castiel says, but instead of moving his hand off Dean's cock, he slides his fingers over it, clearly attempting to make sense of what's going on. Dean can't really object, not when Castiel's caressing him so slowly, and they sit in silence for a few moments before Castiel clears his throat. "Do you... do you engage in this sort of behavior often?"
"The sex or the bringing other men home?" Sam asks, and Castiel waves his free hand, clearly unsure of what he's supposed to say.
"The... both."
"We fuck all the time," Dean says, propping himself up on his elbows, and Sam nods, not admonishing Dean for speaking. "And you're the first Sam's brought home."
"Oh." Castiel pauses, staring at a point on the wall behind Sam for a while before nodding. "You look nice, Dean."
"Can we keep going?" Dean asks, more to Sam than to Castiel, and Sam nods, leaning forward and pressing his mouth to Castiel's neck. Uncertain, Castiel freezes before realizing that he's all right with this situation, all right with having Dean beneath him on the bed and Sam kissing along his neck, and he tugs Dean's panties down slowly, managing to get them off with minimal effort. He pushes up the front of the skirt Dean is wearing, licking his teeth and looking down at his already hard cock before wrapping his hand around it, jacking him off slowly.
Dean tilts his head back, his dick already throbbing in Castiel's hand, and he knows that if they keep it up for much longer, he won't be able to stop himself from coming. Sam seems to realize this and he grabs Castiel's wrist, tugging his hand away from Dean's cock and leaning in slightly. "Leave him alone for right now," Sam says lowly before kissing Castiel hard. Dean can practically hear Castiel's heart speed up in his chest and he disentangles himself from his brother and Castiel, smoothing down the front of his uniform and waiting for any further instructions.
Sam breaks the kiss with Castiel in order to look at Dean, his eyes dark with lust. "Get our box," he says lowly, pushing at Dean's legs. "And take off your shoes."
Dean complies, getting up off the bed and hastily removing the heels before walking to their closet and sliding out an oversized garment box that Sam uses as storage for their bedroom toys. They don't use it often- Sam enjoys torturing Dean with only his hands for the most part- but Dean enjoys the thrill it brings, the heady feeling of humiliation and Sam having absolute control, and if he said he wasn't excited to have Castiel use some of these on him, he'd be the worst kind of liar.
When he gets back into the bedroom, Castiel's shirt is half off, Sam's hands on his chest and tweaking at one of his nipples, causing Castiel to moan in a way that sends pleasure shooting straight to Dean's cock. He makes his way back over to the bed and sits down, setting the box in his lap and watching his brother continue to lavish attention on Castiel's chest, which seems to be more than a little sensitive. He's happy with just watching for the moment.
Sam finally pulls away from Castiel's chest, sliding his hands over the other man's skin slowly before looking at Dean. "What do you want us to do to you?" he asks, and Dean simply blinks at him. Sam rarely- if ever- asks Dean what he needs. Mostly they just end up doing what Sam wants and Dean enjoys it anyway.
"Whatever you want," Dean finally says, because having Castiel here is good enough for him. He doesn't really have a preference for whatever else happens.
"All right." Sam leans forward and pulls the straps of the dress down on Dean's arms, tugging down the front of the dress far enough that his brother's chest is exposed. "How do you feel about bondage, Cas?"
Castiel makes a slightly strangled noise and it's clear that he's having trouble keeping up with all of this, but he nods after a moment, turning red. "I guess I like it."
"Good." Sam flips open the box, digging through it before tugging out a pair of handcuffs. They aren't the pink fuzzy ones that have a safety switch but the kind cops use and before Dean can object, Sam's pulling his hands forward and cuffing them together uncomfortably. The metal digs into Dean's wrists but he keeps his mouth shut and his eyes trained on Sam's face, waiting for whatever his brother feels like doing next. "Cas, come here."
Castiel moves forward on the bed, sitting beside Sam and Dean and clearly trying to keep himself calmed down. Dean can see the outline of cock through his trousers, Castiel's dick thick and long, and he's eager to get it in his mouth already, to see Castiel looking absolutely fucked. Now, however, he needs to deal with Sam and whatever Sam wants to do with him. "I want your help," Sam says lowly, pressing his lips to Castiel's cheek and pushing the box towards him.
There's an assortment of toys in there ranging from vibrators to cockrings to clothespins, and Castiel stares down at it uncertainly for a few moments before tugging out a hot pink cockring, Sam grinning and watching Castiel slide it down over Dean's rockhard cock. It's uncomfortable around the base of his cock, the pressure in his balls almost overwhelming, but Dean bites his lip and attempts to get accustomed to it because there's no damn way he's going to show how much discomfort he's currently in.
"Good choice," Sam says lowly, running his finger down the shaft of Dean's cock slowly and coming to rest on his balls. "I'm kind of in the mood for pain."
Dean swallows and watches Sam pull out a handful of clothespins, handing some of them to Castiel before pinching Dean's chest so that he can attach the clothespins to his nipples. Soon enough, Dean's chest is adorned with clothespins, pinching the skin and leaving it red, and the pain is almost overwhelming. Dean's fighting back tears by the time his brother is done, and both Sam and Castiel look relatively pleased with the state he's in, red-faced and bound with his skirt pushed up around his stomach, his cock needing relief that he isn't going to get.
"I want to see you suck his cock," Sam says to Dean, gesturing to Castiel, and Dean nods, managing to get on his knees after a few moments of struggle. Carefully, he manages to get Castiel's slacks undone with his bound hands before Sam shoves him down so he's practically on his stomach, only his elbows keeping him from being face-down in the mattress. "He's great," Sam tells Castiel, and Dean leans forward, nudging against Castiel's cock with his mouth, the thin cotton of Castiel's boxers doing nothing to disguise how hard he is.
Dean runs his tongue over the shaft of Castiel’s cock, the taste of cotton deterring him only a little from continuing to work Castiel’s cock over through his boxers. He nuzzles against it, wishing he could do more, but without the use of his hands, he's essentially at Sam and Castiel's mercy. After a moment, Castiel pushes his boxers down, revealing his cock; it's as thick as Dean was expecting, coarse black pubes at the base and his balls looking more than a little inviting, and Dean looks it over for a moment, practically feeling Castiel get harder at his gaze alone.
He flicks his tongue over the head, savoring the taste of the precome there- he tastes different than Sam, but it isn't exactly a bad thing- before languidly pressing his mouth to the spot where Castiel's foreskin is attached. Castiel bucks forward almost immediately and it's clear that's a sensitive spot for him but Dean wants to find every area, make this the best blowjob Castiel ever fucking gets, and as a result of his exploration he drags his tongue around the corona, feeling Castiel tense beneath him.
"Oh," Castiel hisses lowly, covering his mouth with one hand as he reclines against the headboard, and Dean takes that as a sign to keep going. He slides his tongue down the vein throbbing on the underbelly of Castiel's cock, takes his time slicking up the shaft. Even though his focus is going to be the head, the areas that made Castiel jerk beneath him, the shaft needs to have attention paid to it as well, every second that Dean laps across it another second where he has Castiel essentially at his beck and call, and he works his way down it slowly before coming to rest at Castiel's balls.
Dean takes a deep breath and almost lovingly strokes his tongue across Castiel's right testicle, feeling Castiel shudder beneath him. Another sensitive area, another spot where Dean can work Castiel up into a frenzy, and the thought of this excites Dean. He leans forward, takes one of Castiel's balls in his mouth and sucks gently, eyes slipping closed as one of Castiel's hands goes to his hair, tugging on it.
A moment later, Dean's ass is being pushed up in the air, Sam's familiar fingers digging into his thighs, and Dean groans, pulling back slightly and lapping at the base of Castiel's cock. There's the cold, wet sensation of lube dripping down Dean's ass and he can't help but whimper, two of Sam's fingers entering him slowly. They do this enough that he can take a lot without much pain, although there's still the dull ache and burn as Sam scissors slowly.
Dean concentrates on Castiel's cock, ignoring his brother currently fingerfucking him and working his way back up to the head of Castiel's cock, taking it in his mouth slowly. Sam tugs his fingers out of Dean's ass and there's a moment of emptiness before something thick and plastic is being forced inside him, Dean grunting and dropping his forehead against Castiel's thigh. "Shit."
Sam smacks him hard on the ass, the spot stinging like hell even as his brother speaks. "I'm tired of hearing your voice unless you're begging for more, Dean."
Dean doesn't have time to adjust to the thing currently buried inside him before Sam flips a small switch and it starts to vibrate, sending absolute fucking pleasure searing through Dean's body. The tip of the vibrator is pressed to his prostate, every single motion of the vibrator leaving him feeling dizzy, and Dean knows that if it weren't for the cockring currently wrapped around the base of his prick, he'd have come all over the sheets.
As it is, however, he knows that neither Sam nor Castiel is going to let him come unless they've both gotten off before him and Dean has to make that happen. He leans back in, tongue worrying the slit in the head of Castiel's cock and coaxing out more precome, even as he wraps his mouth around the crown, lips pressing against it. Castiel groans and tightens his grip on Dean's head, tugging off the wig; Sam doesn't object so Dean takes it as a sign that he can do whatever he pleases, just so long as he gets one of them off in the process.
Keeping his ass in the air, well-aware that Sam is still watching the two of them, Dean lowers himself further onto Castiel's cock, his lips stretching in order to take him in deeper. He tries not to gag on it as he presses down as far as he can go, tongue pressed flat against the head of Castiel's cock as he manages to keep from going deeper. Castiel gasps and Dean realizes he's getting someone who isn't Sam off, forcing himself to fight down a smile as he swallows around Castiel's dick.
A second later and Castiel's shooting down his throat, his seed dripping down Dean's chin and onto the sheets, and Dean pulls back slightly, his mouth full of the other man's come. Sam grabs his face before he can spit, looking at him closely before smiling. "Swallow."
Dean gives him a dark look but does as he's told nonetheless, the taste of Castiel's come not exactly an unpleasant one but not an experience he wants to repeat anytime soon. Sam kisses him once he's swallowed, the liplock almost chaste in nature, but before Dean can relax any, Sam forces him back down on all fours. "Lick it off the sheets and then clean his cock," he orders, and Dean drags his tongue over the sheets, lapping up whatever come fell from his mouth before turning his attention back to Castiel's cock.
He's almost entirely flaccid by now, looking a little confused, but Dean takes his time cleaning Castiel's cock off with his tongue, stroking it from base to head with his mouth. By the time he's finished, Castiel's half-hard again and Dean knows that if they keep it up, he'll be a mess by the end of the night.
"Good girl," Sam says, twisting the vibrator still slid up Dean's ass, and Dean groans, trying not to let Sam see how much he's enjoying having his ass spread so wide. "We should do this more often. Sit up."
Dean sits up, forcing the vibrator in as deep as it can go and watching his brother obediently, trying not to look at Castiel, who seems utterly overwhelmed. "I want to get rid of the clothespins," Sam says, and Dean braces himself for what's coming.
Sam yanks off a clothespin with little chagrin, leaving a red welt on Dean's skin. Dean gasps despite himself but twists his fingers together in front of him, trying his best to keep the pain from showing on his face. This hurts like hell and when Sam tugs off another one of the clothespins, Dean audibly groans, which only makes Sam look more pleased. By the time Sam has pulled off all the clothespins, Dean is nearly crying again, even the pleasure coursing through him from the vibrator not doing much to quell the pain in his chest. His skin is a mottled mess of red marks and bruises by this point, but Sam leans in slightly, running his hands over Dean's chest and kissing him on the collarbone. "You're doing great," he murmurs, and it isn't incredibly reassuring.
Dean stays still, however, even as Sam's fingers continue coaxing at the red flesh, leaving Dean feels conflicted about this whole thing. "I want him to fuck you," Sam says lowly, glancing at Castiel. "I want to watch him fuck you."
"Okay," Dean murmurs. He doesn't care by this point, just wants to get off already, and if he can achieve that by letting Castiel fuck him however he wants, he's all right with that.
"Are you clean?" Sam asks, looking at Castiel and gesturing slightly, and Castiel nods.
"I... yeah."
"You sure?"
"I've only been with one other person. I'm sure."
"You're practically a virgin," Sam says, and he tugs Castiel over. It's clear from his expression that he's thinking of how to best utilize this. He kisses along Castiel's neck, holds him by the hips and teases at the flesh there slowly, his fingers barely brushing over Castiel's hard cock. "You're going to fuck her," Sam says dismissively.
"All right." It's becoming clearer every moment that whatever Sam has got going on is beginning to infect Castiel in the same way it infected Dean a long time ago, and Dean isn't sure if that's a good thing or not.
"Lay down," Sam says to Dean, and Dean does as he's told, laying back against the pillows and spreading his legs wide. Sam pulls the vibrator out of him slowly, leaving Dean gasping and feeling emptier than ever. He watches Castiel quietly, keeping his legs spread and his ass on display, and Castiel watches him in return before putting his hands on either of Dean's thighs and pushing them apart further.
He leans in, kissing down Dean's thighs and leaving small marks on the freckled skin before he reaches the other man's cock. Castiel pushes Dean's skirt up the rest of the way and before Dean can protest, Castiel's tongue is running down the crack of Dean's ass, playing over the sensitive skin surrounding his entrance and leaving a sort of numb pleasure slamming its way up Dean's spine.
"Fuck, you're dirty," Sam murmurs, starting to undo his own slacks, but Castiel ignores him, burying his face in between Dean's legs and pushing his tongue past the ring of muscle loosened up by the vibrator. Dean's only had this sensation on the few rare occasions when Sam feels like trying it out, and he enjoys it thoroughly, even when Castiel pushes his tongue in all the way, leaving Dean feeling wet and fucked out.
Castiel's clumsy at tongue-fucking but somehow it leaves Dean wanting to beg for more, his breath catching in his throat every time Castiel flicks his tongue a certain way. "Fuck," Dean hisses after a few moments, arching up off the bed. "Please, please, can I please come?"
"No," Sam says, and Castiel pulls back slightly, one of Sam's large hands sliding through his hair. "Fuck him already."
Castiel swallows and it's clear he's unsure of what it is he's supposed to be doing, although he steels himself after a few moments and picks up the lube laying on the bed, pouring some onto his hand and stroking his cock slowly, coating it entirely and pressing the head to Dean's ass. He's already stretched out, ready for pretty much whatever Sam and Castiel decide to throw at him, and if one of those things is getting fucked up the ass, he can handle it.
Castiel pushes into him slowly after a few moments, Dean groaning as Castiel buries himself inside Dean fully, and as slow as Castiel is moving, it's still uncomfortable. Once he's sheathed entirely inside Dean, the tip of his cock pressing against the bundle of nerves buried deep inside Dean's ass, he freezes, unsure where to go from there.
Sam takes him by the hips, pulls him back slightly and forces him to move forward again, and before Castiel really knows what he's doing, he's rocking into Dean, fucking him at a slow, rhythmic pace. Sam grins, kissing along Castiel's neck and pressing against the smaller hand, grinding his trouser-clad cock against Castiel's ass slowly. "Can I fuck you?" he asks after a while of Castiel clumsily fucking into Dean, who's beginning to wish he had more stimulation.
"What?" Castiel asks quickly, twisting his head around to look at Sam. They stare at each other for a few moments before Castiel shrugs, clearly nervous. "I... Why?"
"You're fucking my brother. I think it's fair that I get to fuck you in return." Sam nuzzles into Castiel's neck, a finger sliding down over Castiel's ass slowly and coming to rest on his entrance. "You been fucked in the ass before?"
"No."
"Then you might as well start, right?" Sam takes the lube from Castiel, spreading the clear fluid over his fingers slowly and pressing one against Castiel's asshole. Dean, still pinned beneath Castiel with the other man's hard cock buried inside him, gets a good look at the discomfort that spreads across Castiel's face, momentarily wondering if that's how he used to look when Sam tried to fuck him. To be fair, his brother doesn't exactly have small fingers.
Sam begins to fingerfuck Castiel, driving his index finger into the other man as hard and deep as he dares, and Castiel ends up taking it out on Dean, who's beginning to discover that when Castiel is provoked, he turns into a fucking beast.
"Harder," Dean finally whispers, staring up at Castiel and doing his best to drive the other man deeper, rolling his hips down in a feeble attempt to get Castiel to fuck him as hard as he possibly can. "Come on, please, just fuck me harder."
Sam slips another finger into Castiel, who promptly groans, leaning over Dean in order to grab the headboard, slamming into Dean even as Sam starts to stretch his ass out methodically. “How do you do this?” Castiel murmurs after a moment, his breath hot against Dean’s cheek as he slams into him, clearly attempting to match the pace Sam is establishing.
Dean grins despite himself, leaning up and kissing Castiel on the mouth gently. "It gets easier," he says after a moment, gasping as Castiel drives especially deep. He might have just implied that Castiel would do this with them again, and surprisingly, he's okay with that. He likes that.
Castiel makes a strangled noise and buries himself in Dean, refusing to move for a few moments. Sam's clearly pushing into him, Castiel's fingers digging into the headboard and the expression on his face one of utmost pain as Sam pushes in deeper. "It's okay," Dean whispers, and although he can't do much to help Castiel out, he can feel the other man relax slightly at his words alone.
"I'm in," Sam says, and Dean- who lost his virginity to his brother and knows that the size of Sam's cock leaves little to be desired- genuinely feels for Castiel, who seems momentarily paralyzed. "Move."
Castiel refuses to do so and Sam grabs his hips, slamming into him after a moment and forcing him to fuck into Dean. Dean arches up off the bed, feeling thoroughly fucked now that he has the weight of two men driving into him. Castiel's hands go from the headboard to Dean's shoulders, fingers digging into the skin there, and Dean knows that Castiel's being pushed towards the edge. He wants to see Castiel break, wants Castiel to fuck him harder than Dean's been fucked in a long time, and he can tell that there isn't much holding him back now. Sam fucks into Castiel almost brutally hard, the noises that leave Castiel's lips little more than pained cries mingling with a sort of sadistic pleasure, and Dean's starting to see that maybe the guy currently slamming into him has a kinky side.
This manifests when Sam thrusts into Castiel particularly deep, Castiel practically screaming and dropping his head forward. When he looks up again, it's clear he's broken, Dean swallowing and preparing himself for the onslaught. What he gets is Castiel's fingers against his throat, pressing down hard enough to cut off the air and leave Dean dizzy. He likes it- hell, he fucking loves it- and he doesn't bother fighting it, eyelids fluttering as darkness starts to creep in on the corners of his eyes.
"Don't knock him out," Sam says smoothly, and Castiel loosens his grasp, Dean blinking the darkness out of his eyes and gasping for air. "It's no fun fucking someone who's unconscious."
Dean's feeling heady, his cock close to bursting but absolutely unable to, and Castiel leans down, peppering kisses along his neck and nuzzling against him before his hands are back at Dean's throat. Choking has never been something Sam was too fond of but Dean likes it, likes the utter loss of control that it offers, and apparently Castiel enjoys the look on Dean's face because he presses harder, leaving Dean feeling dizzy and nearly high. It isn’t long before Castiel shudders and goes slack, a heat pooling in Dean’s gut, and he knows that the other man came.
Sam’s still fucking him, though, which means Dean’s still on the receiving end of most of his brother’s weight. Castiel does him a favour and pulls out, though, and Dean watches the two of them quietly before Sam climaxes, grabbing Castiel’s waist hard enough to elicit a groan of pain from the slimmer man and leaving Castiel just as fucked out as Dean’s currently feeling. “Sam,” Dean murmurs the moment his brother pulls out of Castiel, twisting slightly on the bed in order to look at Sam pleadingly. “Come on, man, you’ve got to let me come.”
“I could just leave you there.”
“Please, please, Sammy.”
Sam glances between his brother and Castiel, who’s recovered enough to sit up, and it’s immediately apparent that Sam has a plan for all of this. “I want to try something,” he says bluntly, wrapping his hand around Castiel’s cock and starting to jack him off. Castiel just takes it in stride, too tired by this point to object to it, and Dean watches the two of them for a few moments, feeling the heat in his stomach begin to turn into total desperation. He needs to come, needs it more than anything, and the dull ache in his balls is nearly enough to leave him in tears. He just wants to come already.
“You really don’t have any intention of stopping,” Castiel says, more of a statement than a question, and Sam kisses him on the neck.
“This is the last one, swear.” Sam works Castiel back up to full hardness before pulling Dean forward, running his hands over his brother’s thighs before lubing up his ass again, looking at him steadily and shoving him towards Castiel. “Ride his cock.”
Dean, exhausted and feeling mentally unstable by this point of the night, slips his hands over Castiel’s head, using his shoulders to keep his balance thanks to the fact he still has no way to use his hands. Cautiously he straddles Castiel’s waist, poising himself over Castiel’s throbbing prick, and Castiel takes the initiative to guide the tip of his cock to Dean’s ass, pushing in slowly. Dean’s tired of being patient, of waiting for Castiel to fuck him slow and deep, and he pushes his knees down on the bed and takes it upon himself to impale himself on Castiel’s cock, groaning as he forces the other man as far in him as he can possibly get. He’s already fucked out, his ass still dripping come from Castiel’s last climax, and it’s relatively easy to get a pace going, although the faster he goes, the harder he tries to get fucked, the more his thighs burn and the more tired he gets.
He freezes when Sam grabs his waist, his heart skipping a beat when his brother presses the tip of his cock to Dean’s ass. “Sam,” Dean hisses, trying to twist around, because he has no clue if he can take them both at the same time.
“It’s fine,” Sam says. It’s a command, plain and simple and clearly not up for argument, and Dean tries to relax, tries to spread his legs further to make it hurt less. Sam pushes in slowly and it hurts like a motherfucker, Dean’s ass stretched wide as both cocks rend him open, his legs shaking. Sam gets all the way in and Dean has never been in so much pain in his entire life, a few unbidden tears making their way down his face, and bizarrely he wonders if his makeup has smeared during all of his, even as Sam starts trying to strike up a pace.
What results is Castiel pulling out as Sam slams in and the opposing thrusts, the continuous fucking, is leaving Dean feeling more fucked than he’s ever been in his entire life. He drops his head against Castiel’s neck, unable to move as both men fuck him without reprieve, and it’s only when Castiel comes that Dean thinks maybe he’ll get a chance to breathe again. Castiel pulls out as soon as he can, which leaves Dean clinging to him tightly as Sam slams into him hard enough to leave Dean gasping for air.
By the time his brother climaxes, Dean is all but broken, his mind no longer processing coherent thoughts. He manages to speak but it’s disjointed, confused, and pained. “Sammy… gotta… fuck…”
Sam slides the cockring off his brother’s dick and pulls Castiel forward by the hair, the smaller man raising no objections as Sam leaves him on his knees behind Dean. “You seem to like licking ass,” Sam says lowly, and Castiel gets the hint, pressing his hands to Dean’s ass and spreading him apart. Dean shudders on the bed but raises his ass more, Castiel immediately running his tongue up Dean’s come-stained crack and dipping his tongue in Dean’s fucked out hole.
Dean groans, grabbing at the sheets with his cuffed hands and trying to stay still, stay calm, because he doesn’t want to do anything that will ruin the sensation and cause Castiel to pull away. Castiel slides his tongue around the rim of Dean’s asshole, licking up as much come as he can possibly standing before leaning forward and rolling Dean onto his back. He kisses him, Dean tasting nothing but a mixture of his brother and Castiel, and he doesn’t mind it. He likes it- it makes it all so much dirtier, more wrong- and kisses back slowly, groaning when Castiel’s hand goes to his throbbing cock.
It only takes a few strokes before Dean shoots his load, come spurting all over the front of the maid uniform and staining the black lace, and he pulls back, swallowing the remnants of the come in his mouth and dropping against the pillows, exhausted. He’s fucked to pieces, unable to even remember his name by this point, but as Sam slides an arm around him, pulls him close and kisses him on the temple, and Castiel takes a spot on his other side, he feels safe and warm and sort of grateful.
He still hates dressing like a girl, but if nights like tonight happen more often because of it, Dean thinks he can probably adapt.