dol_moon: (wincest)
[personal profile] dol_moon
Title : "Fun Time" for Adults
Author : Dolavine
Table : Get your kink on
Prompt : #1 Role Playing
Pairing : Sam/Dean
Rating :NC-17 (It’s porn people)
Word Count : 4,712
Disclaimer : Don’t own.. blah blah blah.. Enjoy this work of fiction.
Warnings : Established Wincest.. Authority figure kink, Hooker Kink
Summary : Dean gets a hankering for some role play and Sam gets to be the object of his desires.
Written for : [livejournal.com profile] spn_30snapshots

AN: Just want to thank my beta [livejournal.com profile] memoonster and my friends who kinda talked me through parts of it while I was staying up way too late on messenger and trying to write while sleep drunk. lol





Dean’s lounging on the bed, remote in hand as he thumbs through the television channels. It’s the same thing he’s been watching for weeks during their dry spell. He’s not made to sit around doing nothing, not happy when he isn’t hunting something and he’s jonesing for some excitement.

The bathroom door opens up and Sam walks into the room, fluffy white towel wrapped around his head, plush white Motel robe on and it isn’t anything Dean hasn’t seen a million times.

He flicks the channel one more time and it’s a movie, a very familiar movie. The woman on the screen is Julia Roberts dressed in a white Hotel bathrobe and towel turban, the movie is Pretty Woman. Dean watches Sam in his robe and towel turban as he digs through his duffel for clean clothes.

A smirk curls up his mouth as he thinks about how much Sammy looks like Julia in that get up. How he would love to just rip that robe right off of him and push him to the floor taking what he wants from him, but that’s nothing new or exciting. Then he has another idea, a boredom breaking idea.

“Hey Sammy,” he says sitting up on the bed and tossing the remote to the side.

Sam looks at him with innocent eyes. “Huh?”

“What do you say about a little, fun time?” Dean’s eyes are gleaming with desire, his mouth still in that dirty smirk.

“Depends on what you’re calling, Fun Time.” Sam is always wary of Dean’s fun time ideas, since the last time he had what he called a fun time, included pissing off a nest of Vampires. They barely got out alive.

“Awww Sammy, don’t be like that,” Dean says with a hurt sound to his voice.

“There are few incidences where your, Fun times are what I call, fun times.”

“Hey I have Awesome fun time ideas,” Dean says as he walks across the room. “Besides this time ends with a very Happy Ending,” he winks at Sam and gives him that coquettish smile he uses when he’s trying to subtly seduce him.

Sam sighs hard and rolls his eyes. He knows he may just regret this but it is Dean and when he promises a happy ending, it means he gets to cum. “Fill me in on the plan.”

Dean tells him the whole Pretty Woman scenario. He then lays out their roles telling Sammy that he’s the prostitute and he will be the john that picks him up in an alley.

“So, basically you’ll be Richard Gere and I’ll be Julia Roberts?” Sam scrunches up his face. “Dude, I am not wearing a mini dress and thigh high boots,” he says, his eyes set and looking directly into Dean’s.

Dean laughs, “If I wanted a chick I wouldn’t be after your dick. No matter how impressive it is.” Dean winks at Sam before pulling the turban off his head and running his fingers through the long strands of wet hair.

“So how are we doing this?” Sam asks as he wraps Dean up in a damp hug, pulling him as close as he can.


Dean pauses for a moment to push up and kiss Sam on the mouth. “Mmmha, well you put on your best slut outfit then go out to the alley and wait for me, I’ll be around to pick you up in a bit,” He slaps Sam’s ass before walking into the bathroom and shutting the door.

Looking through his duffel bag Sam wonders what he could possibly own that would pass as a slutty outfit. He sifts through everything finding an old black t-shirt with a grey dragon logo on it and a pair of jeans he had bought by accident that are hip huggers, they swing way too low below the hip line so he never felt comfortable wearing them.

He slips on the t-shirt admiring how the tight fabric clings to his body, he smoothes over it feeling his hard muscle beneath.

He pulls the jeans on, the waistband hanging on his hips as he buttons them up. The thin line of hair under his navel is completely visible the entire way down to his pubic line. The thick lines of his hip bones are jutting out from under the slightly short tight fitting shirt and he smiles at his reflection. Dean is so gonna love this.

His wet hair hangs in his eyes and he pushes it back with his fingers just making sure it is off his forehead but leaving it messy looking. He slips his hoodie on before knocking on the bathroom door.

“Dean, I’m leaving now,” He yells through the door.

“Good, get outta here so I can get ready,” there’s impatience in Dean’s voice.

Sam smiles, “Wear the grey suit, I love it on you.”

“Dude I am not gonna wear a suit,” Dean yells through the closed door.

“But you’re Richard Gere, he’s a businessman, you have to wear a suit.”

“Richard Gere is a douche bag, I’m gonna wear what I want and that’s that. Now get the hell out of here Sammy, I want to get ready.” He hears the door close before he opens the bathroom door.

He hurries out to the car and opens the trunk pulling out a black suit bag that is tucked under some tarps behind the weapons chest. He smiles at it and heads back in to the motel room.

Sam rounds the corner at the end of the block into the dark Alley; there’s a dim street light on a lamppost halfway down and he saunters underneath it. He leans up against the wall trying to look sexy, one knee bent with his foot behind him flat on the wall, his hands stuffed into his hoodie pockets and his hips pushed out as his t-shirt rides up even farther. He feel out of place but waiting for Dean has his cock hard and his heart fluttering like a school boy on his first date.

It’s not like they haven’t role played before but this time feels so different. This isn’t in the Motel room, in the dark, calling each other by porno names, its not you be the bad school boy and I’ll be the principal. This feels like he’s the hooker and Dean’s his potential john and it’s the hottest damned thing he’s ever done.

Dean slips the blue uniform out of the bag, his eyes raking over it as he licks his lips in anticipation of how it is going to feel on his body, how it’s going to feel while he’s fucking Sam through the blue cotton fabric, and how Sam is gonna blow his load when he sees him get out of the car in it.

He leaves his white cotton t-shirt on as he slips the blue short sleeved shirt over his thick arms, across his barreled chest, each tiny black button fitting snuggly inside of its designated slot.

The slacks glide over his legs, past his bowed knees, up his thighs over his naked crotch as he shifts them into place at his waist. He tucks his shirt down inside of them being careful to leave his cock uncovered as he’s going commando for this game.

There are black shoes in the bottom of the bag, a quick spit shine with his hanky and they are perfect, the shiny black toe showing from under the hem of his trousers and he adds the final touch. He dusts off the navy blue officer’s hat before putting it on his head.

He looks at himself in the mirror, stands tall and smoothes his hands down over the tight police officer uniform admiring the snug fit, how it accents his ass and his crotch. He bites his lower lip before adjusting his hat and heading out the door.

Sam unzips his hoodie as he sees headlights approaching the alleyway. He pushes his t-shirt up a little bit more exposing more of his belly and hip bones. He puts on a coy expression acting like he’s innocent as he watches the car slowly approaching him.

Dean turns the corner of the alleyway seeing Sam leaning up against the building and he slows down to a crawl as he puts a small red light on the top of his car and turns it on. The light is slowly rotating the red light off of the buildings and now Sam’s form.

The red light hits Sam’s eyes and he sort of freaks a bit not sure if it’s Dean or not. He straightens up and starts to walk towards the car as close as he can to the building when he notices it’s the Impala and he sighs in relief.

Dean comes to a complete stop in front of Sam and waves him over to the driver’s side window. He watches his tight body sauntering over to him, the headlights accentuating his tall toned form. The low slung jeans exposing his belly and hip bones that Dean loves to worship so much. He licks his lips before letting them turn up into a filthy grin. The too tight t-shirt Sam’s wearing is stretched across his broad shoulders as his hoodie hangs off of them in a seductive manner. Dean’s cock is half hard with the thought of what he is going to do to Sam.

Sam steps around the car, the red light hitting him in the eyes as he leans down to the open window and seeing Dean in a police officers uniform makes his cock jump to full attention in his jeans. He swears the head is actually peeking up from under the waistband wanting to get its own look at Dean.

“Officer,” Sam says as he leans on the car door.

“What are you doing out here so late at night boy?” Dean’s voice is low and lustful.

“Waiting for my ride,” Sam says giving Dean a big toothy grin.

“So you like to ride huh?” Dean licks his lips as he lets his eyes wander over Sam’s body, like he’s never seen it before.

Sam leans in the window a bit more causing his ass to stick out even farther, his left hip peeking out from under the corner of his hoodie to tease Dean, “Only way to go officer. It sure gets the job done,” he smirks, a glint of desire shining in his eyes.

“I think you’re up to no good,” Dean says pushing open the door and pushing Sam backwards as he steps out of the car.

Sam’s eyes get the full view of Dean’s tight toned body stuffed into that blue police uniform. The way the hat sits on his head and the straight line of his broad shoulders cut a line in the dim street light. Sam’s cock is fully hard now, it’s leaking a wet spot at the waistband of his jeans and he wants to rub at it, but he holds himself back.

Dean shuts the car door and steps around it. Sam’s standing straight now, his belly completely exposed, his hoodie off his shoulders and down his back half way, and those damned Jeans are barely hanging onto his hips. His hips bones are jutting out from under the jeans, the light catching the tanned skin in such a way that it almost glistens and Dean’s cock has reached full attention. He loves this game, this tease of body and mind that they are engaging in.

Its mere seconds and Dean is on top of Sam. His body pressing tight to his back, a hand holding each wrist at Sam’s sides as his hot breath is whispering into Sam’s ear.

“What are you doing out here boy?” The words are heavy and hot. They come out like commands, strained and yet sensual.

Sam swallows hard at the feeling of Dean on him, his hands restrained at his sides by strong fingers squeezing so tight and that voice, low and gravely commanding his obedience. “Just waiting for my ride sir,” he says it like he’s scared and truth be told, it’s a mix of excitement and fear thrumming through him as he presses back into Dean.

“I’ll give you a ride.” Dean pushes Sam forward over the hood of the car. He bends him in half, Sam’s ass pushing up into Dean’s hard cock that’s pressing a thick line through the cotton cloth. “I’ll give you a ride you’ll never forget,” his voice is darker, the gravel deep and extra rough as he strains to push Sam’s legs apart with his feet. Sam’s ass rubbing the thick line of cock pressed firm in Dean’s pants, a wet smear forming across them as he leaks a steady stream of precum from his intense excitement.

Sam groans at the touch, his face pressed against the warm hood of the Impala. His long legs spread wide as Dean’s hard cock rubs itself off over his ass cheeks. His hands are now restrained behind his back and he doesn’t think he can get any harder.

Dean’s holding Sam’s hands with one hand as he runs a finger over the top of Sam’s ass crack peeking up from under the low slung jeans. He licks his lips before leaning forward again; pressing his entire weight on Sam’s back, making sure his cock hits that bare spot of ass.

“I think I am gonna take you downtown for some one on one questioning,” He doesn’t let up on Sam’s body reveling in the feel of his heat pressed so tight to his body.

Sam squirms under Dean’s weight trying to get a tighter fit to his crotch. The hard press of Dean’s cock against his crack has him on edge already.

“Please don’t arrest me Officer.” He chokes the words out around breathy pants of desire.
“Maybe that is just what you need to set you straight boy, a little one on one,” Dean shoves his hips forward, his cock smashes into Sam’s ass. He runs his tongue across Sam’s earlobe.

Sam’s mind goes blank as his cock slams into the fender of the Impala. The fleshy head that’s been peeking up from under his jeans slides across the smooth surface of the car streaking it with precum.

“Please Officer, I’ll do anything you want,” Sam’s words are weak and breathy.

“Anything, you say,” Dean runs a hand down over Sam’s side, feeling the deep curve of his hip. He hooks his thumb under the waistband of his jeans and tugs down on it slipping them completely off of his hip bone exposing his ass cheek. “You’re such a little whore, boy,” his words cut the air like a knife, a sharp tinge to them as they leave his lips.

Sam groans at the feeling of Dean’s thumb pressing into his flesh, his ass being exposed to the cool night air and then quickly covered by warm soft cotton as he feels Dean’s hip replacing his jeans.

“Absolutely anything you want me to do,” his words are groans muffled by hard puffs of breath.

Dean stands up pulling Sam with him, he turns him around still pressed tight to his body pinning him to the car. He looks up into his eyes, the green burning with lust and his lips move spilling out filthy words, “Wanna fuck me boy, wanna put that dick in my ass and hear me beg for it?”

Sam swallows hard, his mouth is suddenly dry. He can’t believe what he’s hearing Dean say to him. He’s not sure what to say but what comes out stuns even him, “You want me to make you beg for it Officer?”

“Oh a filthy whore like you would love that wouldn’t you. You’d love to make me beg for your cock. Well, I don’t beg for anyone’s cock,” Dean’s eyes go dark with lust, his voice drops a few more octaves as he pulls Sam to the back of the car and swings the door open.

“No, Officer, please don’t,” Sam begs as he’s cut off by Dean’s rough voice.

“Shut the fuck up and get on your knees boy,” He shoves Sam down by the shoulders; his knees hit the ground with a mild thud. Sam’s long body kneeling in front of him makes him hard as a rock and he pulls out his cock. “You want my cock don’t you, whore?” He sits down on the back seat, feet planted outside of the car.

Sam stares at the pink flesh made even brighter against the dark blue and he wants to lunge forward and suck it down, taste the glistening head as it slides over his tongue to the back of his throat. He stares at it, and then up at Dean’s lust blown eyes and all he can say is, “Yes sir,” the tiny sounds coming from his lips are submissive and hungry all at once.

“Suck it boy, what are you waiting for,” Dean waggles the hard member at Sam’s face.

The cool damp cement is bleeding through Sam’s jeans to his knees as he moves forward on them to settle between Dean’s thighs. Dean’s warm hand cups around the back of his neck guiding him forward until he’s nestled in Dean’s crotch.

It doesn’t take any prodding from Dean to get Sam right where he wants him, he comes willingly and very eager to obey. His hot mouth sinks down on Dean’s cock as his eyes turn upward to look at Dean’s face and that makes Dean come apart. Sam’s innocent eyes locked on his, that hungry stare as he bobs up and down swallowing his cock and Dean wants the world to come crashing down around them, wants to let loose and fill Sam’s cheeks with his cum, but he doesn’t. Instead he slows Sam’s vigorous pace by putting his thumb inside of his mouth alongside of his cock to ease the sensation.

Sam slurps loud with the loss of suction due to the addition of the thick digit. He frowns a little having to work so much harder to gain suction and he grunts with a mild disapproval.

“Don’t stop boy, suck that cock,” Dean’s sex laden voice is a bit softer even though the words are hard.

Sam continues to move up and down over digit and cock. His tongue working over the slit each time he comes over the head for added sensation, since he can’t enclose his lips tightly around the shaft. He’s humming the best he can with each swallow letting his throat vibrate around the head and he feels Dean bucking into his mouth.

Dean feels like he’s about to lose every once of self control he’s trying so hard to keep in check. Having Sam like this, like this right here, needy and ready to please him at any cost is more than he thinks he can take. He knows he’s close and if he doesn’t stop Sam’s incredible mouth he’s going to blow his load too soon.

“Stop it boy, get off me,” He commands. His hands are shaking as he runs his thumbs over Sam’s lips and he pulls off with a loud slurp.

“Did I do something wrong officer?” Sam’s voice is raw but timid. He never breaks eye contact as he strokes Dean’s thick thighs through his trousers.

“Get in the fucking back seat, on your hands and knees,” Dean’s voice is strangled, his mouth is dry from panting and his tongue feels thick as he says the words.

Sam pushes past Dean who has moved aside for him and climbs into the back seat. He gets on his hands and knees, his jeans are now dipping half way down his ass. He turns and looks over his shoulder at Dean who is staring at the display with his lower lip clenched between his teeth and his hand working slow strokes over his cock. “Is this what you want Officer?” Sam’s voice is teasing as he wiggles his ass at Dean.

Dean climbs in the back seat before closing the door. He gets on his knees and rubs a palm over one of Sam’s half exposed ass cheeks. “This is exactly what I want,” His voice is dark and lustful. He squeezes Sam’s cheek before ripping his jean the rest of the way down exposing his ass completely.

Sam arches his back and pushes his ass at Dean. He knows what is coming and he wants it so bad he can taste it. His cock is being strangled by the waistband of the jeans and that is okay because it’s just enough pain to keep him from cuming all over himself, too soon.

Dean takes a small packet of lube from his breast pocket and rips it open. He smears a small amount on Sam’s hole, using his thumb to circle the puckered entrance. Sam shudders under the touch so Dean increases the push forcing the tip of his thumb inside past the tight ring of muscle. Sam bucks into him, a small whimper of a moan escaping his throat. “You like that whore, want me to fuck your ass,” Dean says as he pushes deeper, adding his index finger for deeper penetration and stretch.

Sam bites his lower lip and squeezes his eyes shut at the feeling, the thick fingers stretching his hole is slightly painful yet so fucking good he wants more, deeper inside of his ass. “Uhhhha,” he says it like a moan of pure exquisite pleasure.

He’s working his lube slicked fingers in and out of Sam’s stretched ass, pushing deeper, searching for his prostate, and then he finds it. The gasp Sam makes as he arches his back shoving his ass hard into Dean’s hand gives him the signal. “Now beg me for it slut,” he commands Sam with dark commanding desire.

“Please Dean, please fuck my ass,” his voice is shaky as he begs, the sensations shooting through him and his cock is in dire need of some attention.

“Who’s Dean?” Dean says before bringing a hand down hard across Sam’s ass cheeks, the crack eliciting a sharp yelp from him. “Tell me whore, is he one of your fuck buddies, one of the dirty John’s that you fuck in this alley,” Dean feels like he’s losing his sanity, like he’s losing himself inside of this dark fantasy they are building.

“No sir, no, I’m sorry Officer. Fuck my ass Officer; please fuck me hard like the dirty slut I am.” Sam whimpers at the loss of fingers in his ass, the words almost whispered out with hot breaths of air.

“That’s better,” Dean softens his voice as he slicks up his cock readying it for entry.

He lines it up with Sam’s stretched out hole and then starts to gently push it inside. He moves slowly at first, waiting for Sam to push back into him, giving him the signal to go all the way inside. He pumps his head against the puckered ring, letting it pull on his head as Sam moans and babbles a string of curse words before shoving back onto Dean’s rock hard cock. It slips in easily, the lube and stretch making it effortless and Sam seems to love it, he’s pushing himself so far down on to it that Dean’s got every possible inch inside of him.

Sam can barely hold himself up at this point and he lets himself fall forward onto his elbows making Dean’s cock go even deeper inside of him. He feels a jolt of pure pleasure as Dean’s cock rubs over his prostate. His over sensitized cock jerks against the denim restraint of his jeans. He reaches underneath and pops the button then slips the zipper down letting the hardness fall forward. It’s sweet relief as the heavy weight of it sags forward. The leaking head making sweet lube to ease the friction from the fabric of the seat as the head drags across it, with each thrust of Dean’s hips.

“Yeah, right there! Yeah fuck me. Do it harder sir,” the words are hard grunts as he pushes back faster, harder, begging for deeper penetration and Dean tries to oblige as best he can.

“You want me completely in your ass boy,” he grunts out as he thrusts so hard into Sam’s ass he’s afraid he’s hurting him.

“Oh My God YES!, right there, right fucking there,” Sam screams, the echo reverberating off of the windows. “Oh Yeah, Fuck me, f…u..c..k, ME!,” Sam pushes up onto his knees so that he is now sitting on Dean’s crotch, riding him backwards. His ass is sliding up and down Dean’s hard cock as he kneels in front of Dean’s lap.

Dean is forced back onto his heels as Sam pulls up and then sits on his lap to ride him. “Oh fuck yeah baby, ride me.” His hands are on the door behind him as he braces himself with each slam of Sam’s ass down onto his cock. “So fucking good, you sure know how to please a man,” Dean’s panting out the broken words.

Sam’s body grinds down onto Dean’s crotch, his ass clenching around the thick cock raking over his prostate and he can’t help it, he starts to jerk himself off. His hand working steadily at his cock as his ass pumps Dean’s relentless cock.

Dean knows he so close, his balls are tightening with the need to cum and he can’t hold back much longer. Sam’s ass is milking him, the tight ring clenching with each pull off to the head before plunging down completely again. He feels it twitching inside of the wet heat that is enveloping it and he knows he can’t hold on any longer.

“Fucking gonna…cum,” He grunts out loudly, his hips stuttering as the climax spurts out into Sam.

“Fill my ass sir, fill it full,” Sam pants as he works his hand harder and increases his speed on Dean’s shooting cock. He feel the moist heat as he slides up and down on it, smearing it inside and outside of his ass and he can’t stop himself even if he wanted too, he cums hard over his hand, the hot milky spurts shooting out and landing on the window of the door. It’s the hardest orgasm he’s ever had with Dean buried deep in his ass and he isn’t even worried what he’s going to say about the cum spray on his car window.

Their bodies are writhing as they work through their orgasms. Dean’s hands smoothing over Sam’s back as he stays buried inside of his ass, the aftershocks of his orgasm spasming through his body.

“Oh God Sammy,” His voice is broken and exhausted.

Sam pulls up and off repositioning himself so that Dean can get out from under him and stretch his legs out on the seat. He settles in between them, pushing back against Dean’s chest.

“That was..,” Sam can’t even finish. His brain shut down when he started to cum and he’s not ready to reboot it yet, he just wants to enjoy the sweet afterglow of their sex.

Dean runs his hands through Sam’s hair before leaning up and kissing his cheek. “Amazing,” he says finishing Sam’s sentence. “Just fucking amazing.”

Sam laughs as he notices the windows are steamed up, “We steamed up the windows,” he says reaching up and drawing a heart on the back window. He makes a big heart with an S on one side and a D on the other. “There, S hearts D,” He says snuggling into Dean’s chest and letting out a very satisfied sigh.

Dean can’t help but smile at the gesture. “D sure does love his S, that’s for sure,” he says squeezing Sam tighter and kissing the top of his head.

Looking back into Dean’s face Sam smiles and says, “So I’m your boy whore, huh?” he jokes.

Dean starts to laugh that hearty laugh he gives when Sam’s said something that hits his funny bone. “Only when you’re the whore and I’m the Police Officer. Every other time, you’re just my Sammy,” He says stroking Sam’s hair.

The End
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