AFF Fiction Portal

That Kind of Company

By: angeljade
folder Supernatural › Crossovers
Rating: Adult ++
Chapters: 1
Views: 1,330
Reviews: 0
Recommended: 0
Currently Reading: 0
Disclaimer: I do not own the television series that this fanfiction is written for, nor any of the characters from it. I do not make any money from the writing of this story.

That Kind of Company

Title: That Kind of Company
Fandom: Supernatural/Gilmore Girls Crossover
Author: Angel Jade
Rating: NC-17
Warnings: whore, slash, language, oral…doesn’t contain Wincest, but if you squint, it could make a reference…if you squint.
Spoilers: SPN pilot episode only / GG S3 vaguely
Pairings: Sam (SPN)/Jess (GG)
Summary: It isn’t his style, it never has been. But then this stranger looks at him like he knows him and all Sam wants is to not feel so alone.
Setting: S2ish SPN, although it’s timeline seems irrelevant as it’s sorta AU. S7 GG, but its AU from end of S3, so nothing past then applies.

Author’s note: Ah how confusing. Two Dean’s…in fact, two Jess’ too if you think about it. If you don’t know both fandoms, here’s a brief guide. SPN: Sam and Dean Winchester are brothers, Sam’s girlfriend Jess died in the first episode. GG: Jess Mariano stole Dean Forester’s girlfriend and they pretty much hated each other. Jared Padalecki plays Sam in SPN and Dean in GG…hence the mistaken identity. Still confused? Just skip to the porn and imagine whoever you want.

Big thank you to Maya for the beta!

==================================================

Sam picks the stool furthest away from everyone else in the bar and orders a hard drink to keep him going after a day of travel, deliberately ignoring anyone who so much as looks his way. He’s keeping his eyes down, partly from habit since his face became a little too well known for his liking…and partly because he just wants to have his drink and not be bothered by the scum he’s sharing the establishment with tonight. Despite his keenness to remain invisible, Sam can still feel eyes on his back that definitely aren’t a case of simple paranoia. Unable to stop himself from doing so, he turns to scour the dark room for the source of his uneasy feeling, attempting some amount of subtly doing it.

It’s then he notices the dark-haired boy across the room, looking barely old enough to be in there. He’s staring at Sam, a strange of look recognition and what looks like irritation on his face. Sam casually checks around to see if there’s someone else behind him, but it seems that Sam is the focal point of this stranger’s attention, and he’s sure that’s not a good thing. Though darkly attractive, the boy’s interest makes Sam wary, perhaps even a little intrigued. But forget how long it’s been since he’s had any kind of company, he needs to stay focused.

Another drink in front of him and he’s not sure focus is going to be taking part in any of his actions tonight. Sam just wants the world to go away for a while, or at least until tomorrow morning. He hadn’t intended on getting drunk, but then he’d consciously chosen to spend his night in here. What else is there to do except go back to his bedroom and sleep alone?

Suddenly the uneasy feeling of being watched evolves into a feeling of being snuck up on. Sam quickly turns and realises the guy from across the room is no longer across the room.

“Hey.” The greeting isn’t quite a greeting, sounds more like the start of an argument, if it were possible to start an argument with a single syllable. “What are you doing here?”

It’s accusatory, as if Sam shouldn’t be there, which is technically true. He’s supposed to be doing his job, not getting drunk in a bar that looks as if it’s about to be raided by the police, or at least the health inspectors, any minute. But this kid shouldn’t know that, so Sam regards him with mild suspicion. “What’s it to you?”

The guy looks confused and possibly even offended, studying him with dark eyes that are filled with the same kind of haunted existence Sam sees in his brother’s eyes every now and again. At least he had, before Dean decided to go all John Winchester and disappear into thin air without so much as a note. Sam wants to ask if they’ve met before, because maybe it would explain the weird tension between them. He even tries to recall sleeping with him, though Sam’s list is extremely short and none of the ones he can remember match this guy’s description. More’s the pity.

“Haven’t seen you in here before,” the boy says, finally, leaning at the bar and watching wistfully as the man behind the bar ignores him in favour of serving someone else.

“You want a drink?” Sam asks, before he can stop himself.

“Nah.” The reply is defeated, if not a little bitter.

Sam wonders if he’s missing something here. Then it dawns on him. He’s not an idiot. This place is crawling with them and Sam’s already turned down a few on his way in. “I’m not really…looking for that kind company right now,” he says, carefully.

The dark-haired boy stares at him, soulful eyes quickly becoming guarded as he backs off. “Whatever,” he states, his clenched jaw betraying his emotion as he turns and leaves the bar.

Sam looks down at his drink, thoughtfully. It isn’t his style. It never has been. He thinks that maybe Dean has, despite claims he doesn’t need to pay for sex. But then this isn’t about Dean. And Sam is desperate for a little company, whatever kind it is.

He tries to will himself not to move off the stool, and then, when he finds himself walking to the exit, he begs himself to just head back to his motel and forget he’s ever seen a dark-haired boy with eyes like Dean’s. He knows this is a bad idea, hates himself for even thinking about it, but those eyes are just killing him. Not to mention the mystery of why the stranger seemed to know him. It’s all too much for Sam’s willpower. He gives in.

Exiting the dodgy establishment, he barely moves in time to let two fighting locals pass him by, fists flying in all directions. Sam looks around unfazed, his heart sinking as he realises the guy he’s looking for isn’t there. Dejected, he thinks that maybe heading back to the motel isn’t such a bad idea and begrudgingly walks off in that direction, passing the fight as he goes.

“Heading home?” A voice calls from the side of him as Sam passes the alleyway between the bar and a boarded-up building that has definitely seen better days.

Sam stops in his tracks and turns to face his new friend, his chest tightening now that he’s faced with putting this very stupid idea into practice. “Yeah,” he answers, trying not to look as awkward as he feels. He casts a look down the alley and thinks this is probably where he should have looked first, though why anyone would choose to hang out there is beyond him. There’s dirt, squalor and more trash than Sam’s ever seen in his life and yet this guy doesn’t seem to notice.

“It’s not exactly Star’s Hollow, is it?” the stranger asks him, amused at Sam’s disgust.

Frowning, Sam doesn’t think he’s heard right. That or it’s a local saying…or a private joke…something which Sam is supposed to get, but doesn’t. So he doesn’t reply. Just gives the guy a forced smile.

Again with the studying, the younger man is constantly watching him, waiting for something. Sam isn’t sure what he’s supposed to say. “So, I changed my mind.” He tries to picture Dean doing this… even tries to inflict the same kind of confident tone into his voice. But he’s still not Dean and this…this is awkward.

“I figured,” the guy replies with a confidence Sam could never quite get a hand on. “You ever done this before?”

“Not like this,” Sam replies, honestly, shoving his hand in his pocket and checking his money is still there, not sure whether to ask for a price list.

“Come here,” he urges, still leaning cockily against the wall as if he’d known Sam would come looking. Once Sam’s close enough, he straightens up and takes him by the waist, guiding him until Sam’s the one up against the wall. Sam actually has to stop himself from saying something really stupid when the guy drops to his knees, eyes never leaving Sam’s. The look in his eyes is pure sex and Sam knows then and there this will be worth every penny.

“I’m, uh, Sam, by the way,” he introduces, nervously, caught between a dirty, paint-chipped wall and lips that look like they could commit a multitude of sins without even trying.

The guy takes his time with Sam’s jeans, popping the button before easing the zip down over the obvious bulge, before dragging the rough material from around Sam’s waist. He continues to look up at Sam with that same cocky, dangerous expression that Sam should never have compared to Dean’s. Not when it’s turning him on so much he thinks he might just come there and then. “Sam, huh?” He seems amused by this, enough to make Sam throw him a confused look. “Okay, Sam. I’m Jess.”

Sam winces immediately because wasn’t that just the worst name that could have come out of his mouth. The last thing Sam wants is to associate this with his dead girlfriend. But then Jess is squeezing his ass, pulling them closer together and Sam can’t quite draw in enough oxygen as he leans back against the wall, the name pushed to the back of his mind.

A hand slides up against his shirt, lifting the material to expose his chest as Jess begins a trail of wet kisses down Sam's abdomen. With every inch, he gets closer to Sam's erection. Sam’s breath hitches and his hands desperately clasp the wall to keep him from losing his balance.

Jess finally draws his lips against the head of Sam's cock, deliberately extending the contact until he hears a barely concealed whimper fall from Sam’s lips. With a hidden smirk, he slides his own lips down and takes Sam into his mouth, drawing his tongue across the underside. Sam’s hips buck of their own accord, sinking himself deeper without warning. Jess braces his hands on Sam’s hips, fingers tracing over the cool exposed skin as Sam thrusts deep into his throat, Sam’s own fingers tightening in Jess’ floppy, black hair. Adjusting quickly, Jess lets Sam fuck his mouth with increased speed, knowing he’ll feel the effects for days after as it continues to bruise his throat.

And Sam knows this is wrong, that his body is arched off the wall and every nerve in his body is screaming for this beautiful stranger that has Dean’s eyes and Jess’ name, and for once he doesn’t care. Sam’s done with worrying. He just wants to lose himself inside the intoxicating heat of Jess’ talented mouth and forget for five minutes he’s Sam Winchester.

The moment Jess’ throat tightens around his cock, Sam gets his wish. He comes fast and hard, his mind and body so hazed with arousal that the only thing he can think about is how badly he never wants this feeling to end.

As Jess pulls away from him, he’s barely conscious of the hand slipping into his pocket and pulling out a twenty from Sam’s carefully organised notes. He lets him, grateful he’s avoided the embarrassment of doing it himself. But then Jess is leaving and Sam has so much more he wants to say and do and this is the reason he doesn’t do one night stands, let alone with prostitutes. “Uh, thanks…Jess.”

Jess pauses as the entrance to the alley to look back at Sam. “Nice catching up with you, Dean.” He smirks as he turns and walks away.

Sam frowns, staring off after the stranger in confusion. “Dean?”


End.

This was originally a long plot-filled, roadtrip kind of fic with angst, romance and comedy…but I couldn’t seem to finish it, so I cut it short. I still have 20 pages so maybe I’ll continue it one day.