I was a taller girl too, once. (regala_electra) wrote,
I was a taller girl too, once.

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Fic: High Rollers (SPN, Sam/Dean, NC-17)

High Rollers
Author: Regala Electra
Fandom: SPN
Pairing: Sam/Dean
Rating: NC-17
Warnings: Sexual Content, Language
Spoilers: S3, Red Sky At Morning
Word Count: 4,042
Summary: How they wind up at the Borgata isn’t the important thing, the devil’s in the details after all, and it’s better to ask questions regarding Sam and Dean rolling around naked on money.
Author’s Notes: Without ignited, there would be no pie or joy in this world. Also, this fic would not be completed without her loving assistance.
Feedback is greatly appreciated.


First thing that’s clear once they walk into the Piatto suite room is that someone wasn’t drunk and/or profoundly high when they decided on the décor. It’s the nicest place that he and Dean have ever stayed at, that’s for sure.

Now they’re settled, which means that Sam’s pacing and annoyed, still working out arguments, battling a Dean inside his head that’ll give him an actual answer and not make some deflective comment any time Sam really tries to get Dean talking about the deal.

He’s not even making any headway with the fictional Dean inside his head.

As for the real and original Dean, well, he’s soaking in the tub that’s supposed to be for two people (Sam highly doubts that), fanning the money in front of his face (he was smelling it before and Sam had asked if he needed some alone time with the cash, which lead to the freakin’ bath in the first place). Dean’s hair is all sudded up, slicked up into swirls and peaks, and he looks like the world’s biggest kid taking a tubby and ain’t it cute?

No. It’s disturbing.

Sam makes sure to tell Dean as much, then says, “Seriously, I need to take a shower, Dean. We were on the road for way too long.”

“Dude, unless you want to shower over me, and there’s no freakin’ way I’m letting you try that, then you better suck it up.” Dean then picks up a bottle of bubble bath, shaking the near-empty bottle, he says, “This aromatherapy stuff ain’t as stupid as you’d think. Takes the stress off, I’m all Zen and shit.”

“Right, you’re totally Zen,” Sam says, fighting his need to roll his eyes. “You stay in there any longer and you might suffer some real damage, you know.”

“What the hell do you mean?”

Sam smiles then, wide as possible, a bright toothy grin, and says, right before heading out of harm’s way (don’t know what Dean’s gonna throw at him, after all), “Shrinkage.”

Apparently it’s the bubble bath stuff—Sam hears it make a weak thump against the door.

Bubble baths.

Sam decides it’s better not to speculate on what Dean wants to do next.


The Borgata is kinda more classy than Dean can normally take, but consider this: he wore a friggin’ tux recently, so whatever, at least it’s not one of Trump’s casinos. The idea of staying in something called the Trump anything was too much for him. Plus you really can’t trust a dude walking around with that weird hair, whatever it is, Dean’s pretty sure it might be evil.

(After all, he still has some misgivings about the mop that’s lying in wait on top of Sam’s giant egghead.)

The casino floor is full of all types, finest of the regulars, and it’s only Friday. Still, there’s enough bluehairs to get Sam all hot and bothered, “...ain’t that right, Sammy? You eyein’ anyone special? Don’t be shy. I’m totally your wingman.”

Sam continues on, fucker can take some mighty ass long strides when he wants to, all the way across, heading towards an exit.

“Hey, where the hell are you going?”

“Fresh air,” Sam says shortly.

“Dude, don’t—hey c’mon, don’t get pissy.”

He nearly gets knocked down when Sam stops, whirling around, hand in his pockets, yeah, that ain’t suspicious at all, “Pissy, Dean? Really? What are we doing here? We’re wasting time—”

Fuck, arguing out here, got guards and security keeping close watch, and there’s no fucking way he’s letting Sammy fuck up his game before he’s even started.

Don’t ask him why he fucking does it, element of surprise or some shit, anything to keep Sam from talking, to keep him from walking out, to, whatever, he just goes for it, and it happens.

After all, it’s not the weird, groping your brother in the middle of a friggin’ senior citizen convention, and learning that Sam’s really dying to get laid, considering he’s walking around half-hard, informing Dean way too much of how stiff Sam can really get.


Still, he’s a goddamn good bluffer, doesn’t want to look impressed or anything, just leans forward, tries to keep it cool and collected when he speaks, “Since you’ve ruined any shot of me making any decent scratch, it’s time for plan B.”

It’s kinda awesome that Sam just nods once, tight and quick, his face’s almost frozen, a pained look, the clench of his jaw, and yeah, maybe Dean should get his hand off Sammy’s junk. Still, he takes a second too long, odd how, for a split-second, he’d swear—nah, that would be, well that would be just too fucked up for them. No friggin’ way.

“I’ve been dying to do this,” Dean says as he herds Sam to the elevator, mindful that Sam’s gotta shake off a stiffy on the way, which royally sucks and hell, he won’t even give Sam shit for it, considering the poor bastard’s gonna have to take care of it all by his lonesome. “Wait till you see plan B. Oh yeah.”


“Uh, this is plan B?”

One day, Sam will learn to stop listening to Dean's ridiculous plans.

Sam wishes he could go off to the bathroom and masturbate but he’s pretty sure that he’ll hear no end of it, despite the fact that Dean’s the one who felt him up in public. Also, that’s a pretty good way of revealing a little more than he wants to, because he’s all wound up thanks to Dean’s stalling tactic from them arguing (yet again). It’s probably perfectly innocuous from Dean’s perspective, which only makes Sam more frustrated.

And the more keeps on piling on, ‘cause Dean’s down to his boxer-briefs, on the still-made bed, rolling around. On a pile of cash—the ten thousand dollars of questionably earned cash, to be exact.

It’s probably more impressive when it’s more money, the trouble is, Sam can only pretend he’s not looking by staring at his laptop, remembering to occasionally tap keys and run a fingertip across the mousepad to keep the lie believable. Because that’s all he’s doing—looking. And possibly gawking.

As for the wanting, that, uh, yeah, that’s something he’s really trying not to obsess over, so that’s exactly what’s consuming him, because dammit, he can’t deal with this anymore and Dean’s continued refusal to...goddamn it, he has to say something. “You’re such an asshole.”

There’s a twenty stuck to Dean’s thigh as he sits up, says, “Hey man, you want to have a turn, you go right ahead. No need to be jealous. But you might have to join me, ‘cause fuck, this is fun.”

“Dean, I don’t want to roll around in pile of money.”

“Yeah, I bet you’d want to roll around in coins. Gonna start making the rounds at the nickel slots? Make sure to keep all the names straight, you call Betsy Betty or mix up Esther and Estelle and there’ll be hell to pay.”

Sam can’t be held accountable for his actions. And there aren’t any choices or good excuse any more, it’s fight or fuck this time, so that’s what he does. The only thing he’s got left to do: jumping on Dean, the sudden shift of emotions give him the upper hand, but not for too long. Quick grapple, struggle, trying to just stop the runaround and by doing that, he’s starting something worse.


It’s when Sam bites down on Dean’s neck, that’s the moment that the tussling turned into something else, nearly makes Dean jump out of skin, only all he does is buck against Sam and—oh fuck—that ain’t exactly what he’d been expecting.

Sam’s not just pissed off, he’s turned on, all the way on, and what the hell is with all the demands lately for angry sex?

Not like Sam’s said that or anything but oh god.

“Good goddamn,” Dean says, voice shaking but he tries to stick with rough, ‘cause that’s better than shaking, “What the hell is your problem?”

“You’re my problem. Always are, Dean.” Punctuates it with another bite, this time it’s damn near on Dean’s jugular.

“Fucking—damn it, ow,” and he means it, enough that it gets Sam off of him, good thing, Sammy ain’t taking chances with Dean getting away, trying to crush him into the mattress, forgetting that Dean isn’t a friggin’ girl. Or little old lady. “Don’t you know how to bite? Not that hard, freak.”

Sam blinks, ready to start into a whole discussion on the merits of how much teeth and how hard but uh, maybe it'll be better to do a little something else. Yeah, he should just buck up against Sam again and see what weird face Sam’ll make this time, ‘cause huh, he does make some odd ones when he’s—oh hell, no other way to say it—fucking. God, they’re not even at that point yet, Dean should, well he oughta stop it before it’s too late.

This ain’t Vegas, but still, it’s Atlantic City , skeeve city, and he’s going to hell anyway, he figures.

Yeah, keep on saying that part and it’s not wrong at all that his tongue’s halfway down his brother’s throat, using the same tactic as Sam did when he jumped on Dean.

There’s a groan swallowed, click of teeth, Sam breaking away, grabbing all over, hissing Dean. Dean grabs, pushes Sam’s hair away, then winds his fingers in and grabs it, shocking Sam ‘cause he pulls too hard. Best thing to do, little surprise that he needs, cock hard and ready, and hey, sex and money, that’s what drives the whole goddamn world.

Two I Nevers in one: I never got laid on a pile of money and I never fucked my brother.

‘Course he’s gonna worry more about that last one, after this and—

Man, thinking about later, that’s...that’s never been his thing, and, shit, no, no more thinking. He’s getting back into the action, pulling Sam’s belt off, then, Sam still in a ton of fucking layers while Dean’s only got his jockeys keeping him from leaking pre-come all over Sam’s leg, says to Sam, “You wanna do a strip dance for me?”


“Dude, I’m not gonna fuckin’ tear these clothes off of ya. Strip.”


Despite Dean trying to stick a fifty down Sam’s underwear, saying that he wished he had a single ‘cause your ass ain’t worth more than that, Sam really can’t complain.

It could be because Dean’s mouth—which normally annoys the hell of Sam, all the smartass jokes coming out, can’t shut up, all the food he stuffs in it—that mouth, well, turns out there’s a very good use for it.

Apparently that irritating oral fixation, the one that once made Sam think Dean’s a living example of those cartoon wolves that do the rolling tongue that falls to the floor, well, there’s nothing better than having Dean’s tongue swirling a lick around the head of Sam’s cock.

Dean knows exactly what the very best thing he can do with his mouth, an implication Sam has ignored for a very long time. Until now, that is.

When Dean continues to take more and more of Sam and Sam can’t help it—watching—seeing his dick going in in in Dean’s mouth, it’s all he can do to keep on standing up. Sam doesn’t know what to do with his hands, not going to tug on Dean’s head, direct him what to do, not because of any worry that it would be rude or he might be too rough, no, that’s not the problem, Dean’s doing a bang up job.

Oh god, he’s thinking like Dean; that must have meant his brain’s fully short-circuited.

Loud smacking wet pop, suck and then back down again, Dean making this slight noise, way way back in his throat and Sam’s knees nearly buckle. Sam gets a bright idea, sharp and bright like the thrum in his chest, starts working the base of his cock, Dean’s not touched Sam with his hands yet, just his mouth, holding back.

Hates that he makes this little whine when Dean pulls back, licking his lips, not like he needs it, he’s the right kind of messy, mouth wet and shiny.

“Dude, what the fuck?”


“You’re all set to come from just that? Fuck man, you really do need to get laid more often if that’s all it takes to get your rocks off.”

Sam can totally be excused for the mild streak of homicidal rage that passes through him. Turns out, much like Dean, he takes being denied an orgasm very seriously.


He’s got Sam right where he wants him, kneeling on the bed, pulling Dean’s jockeys down (he’ll kick ‘em off later, once Sam’s flush across the mattress and Dean can figure out what other kind of obscene noises Sammy can make), when Sam says, in that kind of serious bitchy voice of his that could be goddamn buzzkill, only Dean’s way too revved up to let that happen, “Dean, do you know where this money’s been?”

“Sure!” Starts spider-walking his fingers around the narrow of Sam’s waist, dipping low, stroking, he says, “In your asscrack, I think. There you go, look, you got a hundred sticking between your legs. Let me get that for you."

“What? I don’t—”

But it leaves Sam looking around, which man, he actually fell for that?

Sometimes things are just way too easy.

Doesn’t give him a chance to turn back, way Sam’s head snaps back, angle of his face, his hair always in his eyes, across his temple, too messy, as Dean leans forward, damn near surges. It’s the kind of attack that should knock ‘em both over, but doesn’t. Sucks at Sam’s neck, hard, then teeth, scrape against skin, and yeah, that’s a fucking awesome noise that comes tearing out of Sam.

“And that’s how you bite someone, Sammy.”

Sam’s answer, a string of noises, fuck, it almost makes Dean laugh. Almost, Sam taking some initiative now, something Dean’s not gonna complain about for the time being.

No, it’s better to let Sam fumble, fingers digging and scraping into the sides of Dean’s hips, crappy revenge, no where near hard enough to hurt, if anything, hell, Dean’s kinda loving it and ain’t that a kick in the head?

“Goddamn,” he says, because a little blasphemy goes a long way when you’re going to hell.

His friggin’ jockeys are at a weird angle now that Sam’s been pulling and prodding, wriggling a hand inside, bypassing Dean’s cock (the bastard), going instead for his balls, then lower, getting Dean in the awkward position of spreading his legs, needing the touch, feel of Sam’s fingers in places that’re just too goddamn tight.

Dean shoves his boxer-briefs down, gets the curve of Sam’s smile against his neck, shoulder, Sam licking across him, “Been waiting for you to take these off.”

“Yeah? You shoulda just asked, I woulda—”

“No, you wouldn’t, Dean,” Sam mutters, rough, goes to look up at Dean, but Dean can’t take that, the look on Sam’s face now, nope, gotta ignore it, ‘cause this, here, now Dean’s perfectly fine with some sloppy tongue fucking; the kind of harsh pull and play that means business, I’m not going anywhere.

But Sam’s got other ideas (better ideas), pushes him down back on the bed, brief slip of air Dean forces himself to breathe in, he’s not going to let the air get knocked out of him. That kinda move, man, that shit would be embarrassing. It’s barely a second before Sam’s crashing against Dean’s mouth again, biting the bottom of Dean’s lip, quick hit of sharp pain, but enough to—god, that’s half okay, or more than that, little pain a good edge.

He’s mumbling, you fucker, other words crass on his tongue, familiar, only good defense he can take ‘cause Sam here, he’s got a wicked offense. He nearly pins one of Dean’s wrists down, the other fumbling to fist Dean’s cock. His palms are little sweaty, despite the A/C, still, it’s too much friction, too damn much, and Dean really has to get some control before he fucking loses it all over Sam’s hand.

The money’s slippery though, everywhere, just as Dean’s gritting his teeth, trying to get some purchase, can feel the papers stick and it doesn’t help when he moves, 300 thread count sheets rustling underneath. There’s not enough money to cover all of his back, hell, he’s gonna have money sticking everywhere. Finds himself wondering, randomly, if this place’ll blink twice if he says he needs to get some money laundered. Bizarre thought, too weird, so it’s comfortable in Dean’s head, distraction shouldn’t keep him focused, but it does.

Sam’s been taking a tour of Dean’s (awesome) chest, torso, sucking bites and nips, edge of his teeth sinking in a little too hard on the nipples, jesusfuckingchrist. Sam lifts his head and breathes against Dean’s cheek and neck, says, frustration creeping in, “You ever going to come?”

Grunt of annoyance when Dean says, “Fuck, Sammy,” bucks and twists, surprises Sam with the raw force of it, first letting go of Dean’s cock and then it’s easy getting Sam’s hand off his wrist. No longer pinned, he’s free to do whatever he fucking well pleases, a sickening thought lurches as he realizes he wants to do everything and he can, the freedom of it almost sends him hyperventilating.

It doesn’t though and he’ll take whatever measly mercies he can get, not embarrassing himself in bed, well, that’s at the top of the list. He peels a hundred dollar bill off Sam’s thighs, sweaty, almost brings his leg up. And he does, he get Sam to fit up against him, hips to fucking hips, goddamit, cock to cock, no use pretending, needs it now but he can’t.

“C’mon. What are you waiting—” Sam tries to say, the breath almost gets knocked out of him (hey, all’s fair in love and war, or, uh, whatever) as Dean bucks, twists, and they’re going rough and tumbling on the bed. Yeah, that big king bed, it makes Dean feel awkwardly huge, weird perspective to have when tussling with a goddamn giant.

Less fighting though, or even fucking, sloppy kisses, kind of messy work that Dean can barely believe he’s engaging in, the reckless bad kissing of kids bursting into puberty, all enthusiasm and no skill, still, that’s what they’re doing, kissing and rolling, one word noises breaking through despite their best efforts to have their mouths always doing something to each other.





“...are killing m—”






Dean doesn’t answer, one hard push, kind of roll in the money that gets the cash rolling around them too, some of it falling to the floor, fluttering around and nearly taking off in the air.


Rolling right into uncharted territories, they are, Sam nearly gets knocked off the bed, Dean stopping him by pushing most of his weight onto Sam’s chest. It’s unpleasant, but between the gasp and wheeze, there’s almost a laugh, at the ridiculousness of this.

The laugh doesn’t get much of a shot at surviving, dies in a deep groan. Sam hates how noisy he is, can’t be helped, Dean falling flush down on him, not an uncomfortable burden. In fact, not much to complain about when their hips don’t align but settle close enough, Dean’s cock rubbing against Sam’s, and oh, yeah, Sam is all for that.

No, what he’s really for is when Dean licks his lips, has to cant his head up to look into Sam’s eyes, that determined focus of his, Sam never thought Dean would've looked so serious about sex. Dean’s not wandering now, not thinking of something (someone) else, he’s here and Sam almost wants to figure out a way to keep Dean here, tell him this, this, right here, this is why Sam’s gonna fight, do whatever it takes to keep him safe.

Trouble is, Dean’s too deep in denial, damage set too deep to be repaired with a quick fix, so Sam kisses him instead.

It’s a little slippery, mostly friction and Sam’s really trying not to think about all the manhandled money sticking all over him. He concentrates on how Dean’s mouth shapes this perfect o before his lips press close, eyes scrunching, slight wrinkles, crow’s feet and Sam takes the chance, runs his hand, fingers, across the side of Dean’s face. It’s shocking that Dean actually leans into the touch, groans when Sam goes to touch Dean’s jaw, trying to get a different angle when he kisses him again.

“Sam,” Dean says, quick, vibration against Sam’s lips, a deep rumble, then urgently groaning, “Sammy.”

One hard thrust against Sam, actually it’s the perfect angle, their cocks sliding against each other and Dean comes, panting and pressing his face against Sam’s, trying to duck his head away, scrape of stubble against Sam’s cheek.

It surprises Sam that there’s no actual pause, no moment to collect himself, Dean manages to wedge his hand in between them, coating his fingers with his own come and with slicked fingers, he’s stroking Sam, hard pump down Sam’s shaft, too hard. Dean chuckles, voice hoarse, against Sam’s ear. His tongue traces along Sam’s earlobe, and then he says, “Don’t think of whatever old broad normally revs your engine, dude. We’re doing this—”

“I know what we're doing,” Sam says, amazing he can get the words out, “Dean. Fuck.”

“Good point,” Dean agrees, his other hand dipping around Sam’s hip, nudging Sam’s leg up, “Let me at least stick a finger up your ass. Give you a taste of what we can do later. Or I could taste you now—”

Oh God,” Sam says, nearly shouts it as Dean chooses then to grab a handful of Sam’s ass, clutching hard, “only you’d—”

“What? Ruin the moment? Don’t think so, your cock is fucking pulsing in my hand, gonna spurt out all hot and messy, all cuz of me. Not a good time to be a bitch, Sammy.”

Not many things to do, Dean has him in a compromising position after all, but somehow the thought manages to come to the surface, past the surge in him, ready to come, and he says, takes the risk, “What’s better? When you’re asking me to fuck you, Dean?”

“I don’t ask, Sam,” Dean says, fingers going closer, closer, but not close enough, only skimming down his ass and all Sam can do is keep on thrusting up into Dean’s hand.

Fuck,” he breathes out, only word, only thing left in him, holding back too much, heat and rise of it, coming into Dean’s fist.

After, he expects Dean to be smirking, arrogance coming off him like the stink of sex, but Dean just settles back on the scrunched up sheets, cash sticking all over him, even against the wet mess of his stomach.

He knocks his knee against Sam’s before he divides the space, his side and Sam's, little gap in between, a boundary that can be easily broken. “Huh.”


“You’re actually a decent lay. I’m proud of ya.”

Sam snorts, grabs the pillow behind his head and smacks Dean in the face. “Better than that.”

“Worth 10K easy,” Dean says, streak of a grin as he’s weakly grabbing for some bills. Fans a couple of them in Sam’s direction, adds, “Pay you for another round.”

Sam narrows his eyes and pushes the money away, lets it flutter down on Dean’s stomach. “I think next round should involve a shower, I really don’t want to catch the plague because we uh—”

“Had a roll in the hay? Or, heh, in the money,” Dean corrects, little bit of his tongue sneaking between his teeth, small thing he does unconsciously.

“Yeah, in the money.” Sam scrubs his face for a moment, then admits, defeated, “Okay, so this plan of yours didn’t suck.”

Dean nods, slapping Sam on the thigh, sharp burn, meaning it. “That’s because I’m a friggin’ genius.”

Tags: fic, spn fic, wincest
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