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

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Fic: Five People Dean Doesn't Mind Screwing (SPN, Wincest, Dean Het, NC-17)

Five People Dean Doesn't Mind Screwing
Author: Regala Electra
Rating: NC-17
Pairings: Dean/Sam, Dean/Cassie, Dean/Self, Dean/Tara, Dean/Crossroads Demon
Spoilers: All Hell Breaks Loose
Warnings: Explicit Sexual Content, Language
Summary: Dean's always up for variety.
Word Count: 3,650
Author’s Notes: The lovely ignited is, as always, a most fabulous beta, so I must thank her profusely.



He's halfway done with it before Sam notices it, stirring awake, never groggy, he's always bright and fucking chipper.

"Dude, did you just brush my bangs off my forehead?" Looks around wildly and then Sam asks, "Where are the scissors? Wait...why are we in the same bed?"

"I wasn't gonna cut your hair," Dean grumps. Then licks his lips, can still taste Sam’s come, even though too many hours have passed. Fucked Sammy into a damn near sex coma. He asks, "You, uh, remember how I totally blew your mind last night?"

Sam blinks, kinda slow, as if the wheels are turning in his head and then Dean gets an answer. "I don't remember it being my mind. But uh, we never do this, we're—"

"We're not, like, cuddling or anything." Stretches, noisy as he can be, throwing his arm across Sam's chest. Lamely says, "I was bored."

"Ah." The sheet that barely does its job of covering Sam’s business shifts and more of the dark thatch leading down, Sammy’s personal happy trail, becomes visible, almost distracts Dean enough that he misses that look.

He stares pointedly at Sam's grossly smug face. "I don't like that look."

"No, no, it's...sweet," Sam finally finishes and Dean wonders about the likelihood of him ever getting laid again if he pinches Sam in the groin.

But before Dean can insult Sam back, he gets the full morning breath kiss, foul as hell, and doesn't mind it one fucking bit. Not when Sam’s fingers form a fist around Dean’s cock and stroke him hard, leaves Dean with only one option, groaning his own raging morning breath into Sam’s open mouth.

Fuck sweet,” he says when Sam goes to leave bite-kisses across his stubbled jaw.

Sam, the bastard, actually barks out a short laugh, biting down on his earlobe before he says, “That’s the idea.”



In bed, it works. Or, you know, against a wall, in the shower, in the kitchen, on the floor, her sofa—hey, Dean's always for variety and Cassie agrees with him.

Elsewhere, well, it's good but he feels it fraying, unspooling just like the worn sweater she always tosses on at night 'cause her heater's a stubborn bitch, conking out without a goddamn warning.

Still, he's okay with waiting it out. Deluding himself that he can fix this. Says the same to her when he works on the radiator, swears that this time, that it won't wheeze itself to a premature death, kick off when she needs it the most.

She worries her frayed cuff whenever he brings up stuff about what she needs.

He likes how domestic it can be. Waking up and that lazy kind of sex that's not fucking, not when he's pushing inoutinout, lying behind her, murmuring nothing he'll be able to remember in her ear.

She'll tell him though, after, when it's all over, fighting with him. Says that for all his big talk (What? Bragging? Dean's downright modest with her, always tries to lay his cards on the table, that's what gets them into this fight in the first place), that he's got to go, that he's a liar and a freak and that snaps him back, the feeling of the ground dropping beneath his feet.

Lesson learned. Don’t do this. Fall in love? Fuck no, it can’t be...god, it can’t be that, just, the thing about getting close. It sucks and he’s gonna take some of her choice words—mainly the get and the out—and follow her directions right to the fucking letter.

If he stays a moment longer, he might have to fuck her on her precious writing desk, the one she pushed him away from the first time they'd started to coming together, half-dance and nowhere near a fight, pushing her hands flat against his chest, shoving him back. She'd had a plan (that's what she does, makes plans, living too much in her head that it scares him, 'cept that's how Sam operates too, kind of sick that he recognizes it), rode him hard into her mattress till he flipped them over, coming inside her buried deep, groaned her name in the thick curls of her hair.

Dean takes off because that's what was supposed to happen, right from the beginning. Licks his wounds and steadies himself, makes a promise to himself that he knows he'll break, that he'll never let someone else wind him up, kick him somewhere deep that still aches when he realizes if he had shut his fucking mouth, maybe he could have gotten it to work.

He asks her about the radiator when he sees her next, in another state and hell, in another state of mind, in that drowsy night of waiting for the next shoe to drop, if she ever managed to get the heating at her campus apartment fixed.

She tells him, drifting off to sleep, that there’s no way to fix what’s broken beyond repair.



Sam’s going to drag Dean kicking and screaming into monkhood or whatever the hell they call the belief in not getting laid. It’s unnatural how Sam just doesn’t want it.

Doesn’t make any sense to Dean. It’s sex, it’s uncomplicated and it’s, damn, it’s nothing to shoot down, man.

After Sam blows Dean’s awesomely crafted cover of them as secret assassins from Canada in front of Bellyshirt Girl and her hotter redheaded friend who decided short shorts were in (and on her? They so are.), there’s only one thing a guy with a hard-on can do.

“I’m gonna be loud,” Dean announces when he waves the porn magazine he picked up at the last pit stop right in Sammy’s face.

“I’m going to get coffee,” Sam answers, smoothly, looking for his other shoe.

“Yeah, better go for your venti triple lame with extra foam.” Dean starts unbuckling his pants in front of Sam and doesn’t that get him damn near sprinting out of the room. “And don’t whack off in the bushes, I don’t wanna bust you outta jail ‘cause you were in the mood to get your perv on.”

Sam just shudders his reply, heading out, taking the car keys with him.

Great, now it’s just Dean and...himself ‘cause Sam fucking cockblocked him.

The titty mag’s okay, most of them are silicone and the photos are all glossy. He’s not in the mood to purchase some dubious motel porn, because even though he’s the one paying for the room, Sam tends to scan over the final bill, rolling his eyes whenever he finds the high class movie Dean’s decided would be very beneficial to appreciate. Those are Sam Words for God, Dean, can you stop watching so much porn?

The answer is no. Sam may fuck over Dean’s chances of getting to eat pussy, but there’s no way that’s Dean’s gonna be denied visuals of pussy eating. And uh, other things, ‘cause yeah, for Dean, it’s all good.

In fact, that’s what starts him going, just thinking about all of it, how once his body got fully wired to appreciate sex, he did not look back, didn’t hesitate, just plunged in for good or bad, mostly good, ‘cause he’s Dean and he knows, when it’s good, that’s what makes life worth living.

When it’s bad, burying your head in the sand or somethin’, how can someone not want to see someone dangling on that sweet edge, the hot burn of coming apart right at the goddamn seams, sweaty and messy, smelling like sex, voice all crazy, and all you gotta say is, “you want this” or “gonna take all of me” or “gonna eat you till you’re screaming” and fuck

Dean ‘s got a lot of time, not for an encore, just the once, and maybe a shower, let the sex reek air out a bit before Sammy, fuck, before Sam walks in, all high and fuckin’ mighty, ‘cause he doesn’t get these urges.

It’s a goddamn lie, Sam just doesn’t talk about, which makes Dean unable to shut up about it.

Dean’s got his cock out and he stops to push down his jeans, stays mostly dressed, because it’s not like someone else is getting an eyeful, he closed the sketchy window curtains and everything. Doesn’t have to do this in the bathroom, ‘cause Sam would almost be disappointed if Dean didn’t live up to his lack of expectations, plus, fuck standing over the sink, or doing it on the toilet, or rubbing it out during a half-awake cold shower, he’s gonna come hard in this lumpy motel mattress. Not even Magic Fingers offers some good vibrations compared to the rhythm of his hand, pumping slow.

Has to grit down and power through, not coming ‘cause he can do this, holding off, tried to tell Sam about this once, yeah, quickies are awesome, but jerking off real quick is a bad fucking idea, better to get himself damn near crazy with it. To hold out until he can’t no more, because in theory, he’ll be able not to spill his load next time he gets laid.

Shit, if he ever gets laid again, which, fuck it, first willing partner, he’s going to fuck ‘em till they forget their name that by that time, Dean’ll have forgotten just the same.

This’ll probably lead to some crazy thought where he comes across his freaking doppelganger and you know what? Dean doesn’t have a problem with that. He’s a hot piece of ass. The problem would be, if Dean was actually fucking himself, of which one gets to be the catcher and who’s pitching and rock-paper-scissors would end on a draw. Plus, he knows how fucking competitive he gets, that ain’t gonna disappear just because he’s finally evenly matched.

Damn, it would be pretty complicated screwing himself.

And that, as he conjures up a detailed vision of fucking and getting fucked by himself, coming hard, spurting all over his hand and—fuck—Sam’s bed, would be something that Dean would kinda be totally up for.

Damn. First person he’s seeing? Gonna be fucked but hard.



Dean never thought of himself as a starfucker.

Look, it ain’t a matter of him not thinking he’d have a chance to score with some chick spread all over the glossy mags and looking sexy as hell on the big screen, it’s more like, he doesn’t plan stuff like this. All jokes about Lindsay Lohan aside, which, have you see her? Damn, that girl’s a hot mess.

But it’s the way that Tara looks him over, ‘cause he’s already fuckin’ vibrating with the energy of movies being made all around him and how weird these people are—see, that’s the best part, the weirdoes not noticing that Dean’s walking around, a certifiable headcase as his brother likes to say (only with bigger words), and once Tara gives him that smile, oh he is in.

Hey, if the trailer’s a-rocking, don’t come a-knocking, right?

Also, you know, he really is a fan of her work. Big fan.

So here’s how it happens: she’s still all gracious and down to earth, weird obsession with Strawberry-Kiwi Snapple in full effect because she’s turning a bottle around and around in her hands and he’s standing in her trailer like an idiot, no headset on to keep him distracted.

And yeah, he kind of wants to, at the very least, pull that robe off her body and lick her all over, see what kind of crazy expensive lotions and oils she rubs all over. Then he’ll suggest, quiet-like, to her that he’s gonna fuck her up the ass after he’s got her all lubed up and knows he’ll get her to come just by saying it.

He’s never said deep down he’s a good person because deep down, he’s a guy.

Tara raises her head up, all shy, hesitating before she says, “I really don’t do this.”

But the rest of her speech, probably gonna be real earnest and who the fuck knows if it’s honest, she just chucks it and ad-libs. Uh, if that’s the saying for what happens when he gets lunged at in the good way, the knot in her robe undoing itself almost as he slides his hands down around her hips, grabbing her ass, crushing her to him. Lets her know his dick’s standing up and fuck it, applauding at her performance.

Well, there ain’t no applause yet and he’s seriously invested in all the things she tastes like, no shocker that it’s fake strawberries and kiwis (whatever the hell they are) on her lips, in her mouth, huh, must get that kind of a limber tongue from all those speech exercises she does, ‘cause damn.

She’s musky on her skin, no fruity tastes there, perfume he probably can’t pronounce and sure as hell doesn’t recognize and she groans with that deep throaty voice of hers when he starts licking and nibbling at her breasts, nipples hard and peaked. Starts clawing at his back and he’s not one to refuse, yanks off his jacket and she helps him take off his shirt.

And man, she is in the moment, hand down his jeans, over his jockeys, gripping him and shit if she ain’t leading him right where he wants to be, that little bed that’s pushed up right against the wall and everyone’s going to know what they’re doing.

Tells her as much when he slips the condom on, fingering her, thumb circling her clit. There’s not much talking after that, has his head between her knees, gets her off but he promises he’s full service all the way, and fucks her with her legs over his shoulders.

“You were never in the business, were you?”

“Acting?” He’s looking for a wayward boot, remembers his manners and tosses her the robe, which she doesn’t put on, gets up to stretch, fussing with her mussed hair. Then gets the gist of it when she runs a tube of lip gloss across her bottom lip: suggestive little move of the tube. “Don’t need to be paid for something I love doing.”

And strangely enough, that is pretty goddamn true.



“Time’s up.”

Another brunette, this time copper-skinned and wide-eyed, exotic-pretty.

“And yet the hellhounds are running a little late? Or you came to take me down straight to the pit yourself?”

“You decided to spend your last night waiting for me at the crossroads, Dean? How sweet.” She laughs, a tinkling kind of laugh on par with wind-chimes, really fucking obnoxious and she knows it. Probably picked the body just for that laugh (and uh, proximity factors).

He grits his teeth at her in the best smile he can manage, because he can’t help but be repulsed by what he’s gotta do, but hell, he can’t weasel out of the deal at all, but what he can do is get this evil bitch so turned about that her deal-making days will be over.

He lied to Sam when they figured it out, said he’d be saving himself, but he knows that’s a fucking longshot, better he goes down to hell taking her with him.

“One request.”

That gets her attention. “I’m afraid there’s no more Let’s Make a Deal for you, Dean. You can’t protect your brother forever. But I do keep my word.”

“I ain’t talking about that.” Smiles as close as he can get to the real thing, luring her in, first time he trapped her, second time she got him, now it’s his turn again and it’ll be the last time they ever get stuck playing this fucking game. “You seal a deal with just a kiss right?”

“Mmmm,” she purrs and Dean changes his mind. That’s why she picked this body, for that deep noise of interest in the back of her throat, gives a man exactly the right kind of ideas. “I like that you emphasized just there. One last fuck before you go. Didn’t you already do that last night with—”

“Doesn’t matter,” he cuts in but that doesn’t stop her.

Dark eyes damn near sparkle as she must get some insta-demon vision into what exactly Dean was up to last night. “Why, Dean. Tacking on a major sin right before I bring you screaming to Hell? You’re so considerate.”

Yeah, keep on smiling, bitch. Has to smother that down but not enough, she reads it on his face. So he says, “Yeah, and I didn’t shower either. I’m as stained and vile as you’re gonna get me.”

“Now this is interesting. But you’re still disgustingly good, somewhere in there, deep inside. Not going to feel bad that you’re taking advantage of some poor girl? I could leave any moment, you know. Want to be fucking this pussy, which, ooh,” she shimmies, which shit, doesn’t exactly hurt to see, because a black miniskirt never goes out of style, “she’s got a pierced clit. So that’s why her body tingles so much. Mmm, you want to fuck me—her body—and have her come to right when you’re about to come? Another stain on your soul, can never have too much.”

“That’s something that could happen,” Dean drawls. “But it won’t. You’re gonna miss out on the full Dean Winchester Experience—only got a taste twice, bet however you demon bitches get wet, you’ve been aching for me.”

“There’s been things I’ve been aching to do you,” she hisses, venom overriding the musical quality of her stolen voice.

They’re circling around each other, shoes kicking up dust from the crossroads.

“Let’s get to it then,” Dean says.

Not a surprise that a demon attacks, he’s already had the brunt of her kisses, hard and sucking, getting invaded all over again by her tongue, feel the hate coming off her skin in waves. But there’s lust mixed in there and ooh, bad move for the evil demonic bitch ‘cause that’ll be the thing that fucks her over in the end.

Glad he doesn’t have to actually violate the poor girl being ridden by the demon, it’s as soon as she strips naked, wanting him, laid down in the dirt and ready for all sorts of things to be done to her first that he peels off his shirt, shucks down his jeans and yeah, she can fucking see it now, symbols all over his flesh, not to mention, he isn’t lying, he really didn’t shower.

The stench of what he and Sammy did the night before, the remains of it, all over his flesh.

She stands up, naked and furious, Dean makes sure to keep his eyes focused on her face because she didn’t mention the pierced nipples and that’s not a distraction he needs right now.

“You can’t—”

Then it starts, the shuddering and shaking, demon can’t escape out of the body, instead it starts steaming away, screaming out of the skin but in all kinds of bits and wisps of air, feebly trying to get back together but can’t manage it, old magic crippling her but good.

“Yeah, turns out I can. Now you’re screwed, bitch.”



It always begins and ends with Sam, Dean hates it admit it, but it kind of fucking does. As screwed in the head as he might be, whatever he’s gonna do, it comes down to Sam.

Like now, for instance, because once Sam comes, spurting and gasping, that’s when Dean’s gonna fuck him slow, long enough that maybe Sam’ll get hard all over again and won’t that be a sight to see?

‘Cept Sam’s fucking stubborn and okay, Dean’s a little impatient, because hello, they’re celebrating the here and now, no death sentence hanging over his head, so he does what anyone does in his position should do, he cheats, viciously. Detaches himself from Sam’s cock and before Sam can get out Dean what the hell are you doing? he’s mouthing Sam’s balls, but oh, he’s gotta go there.

“Get on your knees.”

And if Sam has any argument left in him, Dean kind of yanks it out with a tug on Sam’s dick, hard enough that Sam clenches his teeth, body tensing, willing himself not to come.

Man, Dean’s really gotta mock Sam for his gangly attempt to get his fifteen-foot limbs situated as he turns around, pushing his ass up in the air, and oh no, they have time for that. Spreads Sammy’s ass cheeks wide, opening him up, Dean says, “Thanks.”

Thanks ‘cause Sam’s saved his ass, so Dean’s gonna do Sam the favor of getting his asshole licked out good and proper.

Sam reacts awesomely too, actually smacks his head so hard against the wall that he curses, loudly and whoever the fuck is sharing the common wall thumps loudly, muffled protest of something brilliant like shut the fuck up.

Can’t let poor Sammy get distracted by that, Dean stops tonguing him to go back to fisting Sam’s cock, pumping hard ‘cause Sam likes it like that and Dean talks Sam through it, meanwhile, busies himself with what he wants to be doing as soon as Sam’s ready for his cock, finger pushing deep instead and bulleye’s (yeah, Dean can be as disgusting as he wants in his fucking head, and fuck it, he’s gonna say it too, get Sam coming with a strangled laugh), hits Sam’s prostate and don’t that just set him off, spurting messy and thick all over the stripped-down sheet.

Once he pushes his cock inside, groaning ‘cause he knows this isn’t going be the best fuck in the history of recorded time, but it’ll do—shit, they’ve got time on their hands—Dean says, “Fuck, I love screwing you.”

“Idiot,” Sam pants and then, changes the topic back to what they’re doing, “Harder.”

And hell, Dean is more than happy to give whatever Sam wants back—in a-fucking-bundance.

Tags: dean/cassie, dean/ofc, dean/other, fic, spn fic, wincest
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