rivers_bend

Title: 5 times Dean got fucked with his boots on
Words: ~2850
Rating: Adult (graphic sex)
Genre: Het and Slash
Pairings: Dean/OFC, Dean/OFC, Dean/OMC, Dean/OMC, Dean/Sam
Warnings/Enticements: Dean starts young (14) with the sexual activity, though there is no underage intercourse.
A/N: this is tangentially related to Power'verse but stands alone. Thanks to mickeym for checking and squee.
Summary: I don't really have anything to add that the title doesn't tell you.



The first time: Home team dugout. (14)

Her name was Michelle and she was seventeen. She didn't know Dean was only a freshman, possibly because when they met, Dean was filling the Impala with gas, and so looked old enough to drive. She went to the Catholic school up the street. She was wicked smart, smoked like a chimney, and rolled her skirt up so it fell several inches above her thigh-high stockings. But Dean's favorite thing about her was her 14 hole Doc Martin boots. He wanted a pair as much as he wanted her.

The sun was setting and they were in the dugout at the public high school. It was football season, so everyone was at the field on the other side of the parking lot, watching the game. Dean had pushed her down on the bench and gotten his tongue up under her skirt. She whimpered and grabbed his hair, and swore like a sailor when she came.

After she pulled on her panties, she pulled off his jacket and laid it in the dirt. "What—" Dean tried to protest, but she said, "I'm not tearing my tights just to give you head," and Dean had nothing more to say on the subject.

Graceful as anything, she knelt between Dean's splayed army surplus boots, and reached for his zipper. He wasn't sure what to expect, but it wasn't that she was going to tug his jeans and shorts down over his ass and lick his balls before she even touched his dick. Not that he was complaining. Hoping to avoid splinters, he just slouched down further on the bench so she had better access.

When she licked her finger and started rubbing at his asshole, Dean decided that Michelle had access to much better porn than he did. But then he was distracted by the wet heat of her mouth on his dick. She pushed her finger in as he came in her mouth, and it hurt, like fuck, he thought, and almost laughed, but it was still the best orgasm ever.

The second time: Behind the drug store. (19)

Lorelei was probably not her real name, but Dean didn't much care. Anthony Johnson bet him $50 that he wouldn't get a hooker to give him head. Plus, he'd pay for the hooker. There was the part where he said he had to watch, for proof and all, but fifty bucks was fifty bucks, and Dean wasn't complaining.

She gave head like a porn star, all sloppy with spit to slick the hand she was using to work his shaft while she bobbed on the head. Catching a movement out of the corner of his eye, Dean looked up to see Tony palming his dick through his jeans. While he was distracted with that, the hooker reached in and started playing with Dean's balls. He watched Tony's eyes following her hand and heard him moan. Wasn't this getting kinky?

Dean leaned back against the bricks, slouching his hips, and Lorelei stopped. "Want me to play with your ass?" she asked. "Think your friend would like that?"

From Tony's glazed look and the long drawn out "Fuuuuuuck" that accompanied the question, Dean reckoned yes.

"Sure," he nodded.

She spat several times onto her fingers, making Dean a little worried about her idea of play. He'd had his own fingers up there enough times to know that even when you were expecting it, it hurt if you weren't relaxed enough, and this was not the most relaxing sex he'd ever had. "Don't worry, sugar," she said.

Lorelei was as good as her word, and when she swallowed his cock right down her throat, his ass just opened up around her finger. She didn't go too fast or too deep, just rubbed and swallowed and hummed. Between that and the noises Tony was making while he watched, Dean came so fast he was worried about his reputation.

The third time: Back seat of the Impala. (22)

Dean was very, very, very drunk. Which was the only explanation he could come up with for the fact that he was folded into the back seat of his car with a man's hand in his pants, his dad not fifty feet away on the other side of a motel door. He didn't know the man's name, though he was pretty sure it wasn't Sam, because when Dean'd called him that by accident, twice, he'd looked pissed off and mumbled something Dean didn't catch.

Apart from being tall, and having floppy hair, he didn’t really look that much like Sam, thank god, because that would just be wrong. What with the way he was sucking on Dean's neck and squeezing his balls and all. Dean probably just called him Sam because he'd gotten used to having his fucking traitorous, geek-boy brother around after eighteen years, and now he was gone and Dean just—what the fuck?

"Okay," he started, meaning that to be a preface to 'what the hell are you doing?' but not-Sam clearly thought it meant that Dean was ok with having his jeans and boxers pulled down to his knees.

The tongue in his mouth and the friction on his dick made it hard to explain he'd actually meant the opposite.

"Can I fuck you?" Mr. Lips asked.

Dean pushed him away and fumbled himself back into the corner. "Dude, I'm not a fag. I like girls."

"Um…" The guy gestured around at the steamed up windows and their general disarray.

"Well, yeah," Dean said, which, granted, wasn't much of an argument, but his tongue felt all thick, and his brain wasn't really… braining.

"Sorry," the guy, maybe Brent? said, when it was clear Dean wasn't going to say anything more. "I'll just leave then?"

Which sounded like a really bad idea, because Dean's dick was kind of hard, and the kissing had felt really good, and he was gonna end up jerking off with his fingers up his ass if this guy left, and that sounded like a lot of trouble.

"I didn't mean I don't like you." Dean grabbed maybe-Brent's wrist and pulled.

"Don’t know if you noticed, but I'm not a girl." Brent tugged at his own cock, which Dean had pulled out of his khakis at some point during the proceedings. It was shiny and red and skinny. Dean started thinking about what it would feel like to have that inside him.

"Do you have any condoms?" That should answer the guy's questions. Show him Dean wasn't a pussy.

"'Course."

"Ok, then."

The guy was a total player, he even had a little packet of lube in his pocket. Girls were so much easier. They made their own, which, woah, really convenient.

"Here. Sit on my lap." Brent pulled Dean up to straddle his spread thighs, and then pushed him a little so he was leaning forward over the front seat. Cold slippery fingers rubbed up behind his balls and then one at a time pushed into him.

Dean felt dizzy and a little sick and wanted the burning stretching to stop and to fill him up so he couldn't think. "More," he said, and pushed back. The burning was replaced with a heavy fullness and then nothing but fingers digging into his hips and lifting him.

"Okay?"

Dean just nodded, head propped on his arms folded on the seatback, hoping Brent could see.

There was no way to stop the hiss through his teeth as Brent's cock breached him. Dick, no matter how skinny, is nothing like a couple of fingers. The pain was sharp and dull, like the time Dean'd cut his finger open on a broken whiskey bottle after drinking it nearly empty. Only this was his ass, not his finger.

"Fuck," he said.

"Yeah," was the breathy answer. "Fuck, you're tight."

No shit, Dean wanted to say, but Brent wrapped a hand around his dick then, and it just came out a strangled moan. He was soft as a soft thing, but his flesh tried to respond.

Brent didn't move his hips, just held Dean flush against his thighs, jerking him hard and slow until it no longer felt like Dean was being torn in half, and his dick overcame pain and alcohol enough to appear interested in the proceedings.

"Okay," Brent said, "Okay. Yeah," and he started to move. Which was actually better.

Dean rocked back to meet his thrusts, focused on the friction, and didn't think about anything for what seemed like hours. Brent finally came with a noise like something Dean had hunted. He couldn't think what. When Dean pulled off his lap and flopped onto the seat next to him, Brent offered to blow him and finish him off. Dean doubted it would do much good and said so.

"Well, thanks," Brent said, as he tucked himself away. He tied a knot in the condom and then sort of held it awkwardly.

"There's a dumpster in the corner of the lot," Dean said.

"Right." Brent pulled his coat off the front seat and climbed out of the car. Dean watched him walk back towards the bar they'd come from.

He pulled up his jeans and struggled out of the car. With no warning at all, he vomited down the side of the ice machine on his way to the room.

The fourth time: Back Room (25)

Dean always thought that sex rooms in clubs existed only in the fevered imaginations of the writers of cable TV shows, but apparently he'd been going to the wrong sorts of establishments. Because this really was a sex room. Men getting and giving blowjobs—in one case at the same time, huh—fucking and being fucked, and generally kissing, groping and manhandling. He could see, though, how chicks probably wouldn't dig this, which was why you had to come to a gay bar to get it.

This trip to New York was supposed to be about figuring out how to stop a haunting when the guy's body was buried in the foundation of a 40 story office building, but neither John nor Dean could come up with anything, and they'd both declared a night off. John had gone down to see an old friend in New Jersey, and Dean headed for Greenwich Village. There was something reassuring about knowing you didn't have to bullshit some story, or flirt, or buy endless rounds of drinks. Just a wink and a nod, and you could get a hand job in the toilets.

This guy had actually bought Dean a drink, asked his name (Steven tonight), and given his own (Eric). When they finished their shots, he laced his fingers through Dean's and pulled him past the heaving sea of bodies on the dance floor through a pair of curtains. "Can I suck you?" he asked when they found a patch of wall that was free.

"Fuck, yeah," Dean said and wondered who turned down a blow job. Leaning back against the tiles, he started to undo his fly.

"Not your dick," Eric said, and gripping Dean's shoulders, turned him to face the wall.

Before Dean could respond, Eric was pulling down his pants and biting his ass. Which wasn't quite what Dean had in mind, until Eric started licking. "What the hell?" Dean jerked away, because, yeah it felt good, but that was just fucking weird. Who did that? Eric pulled him back and licked harder, groaning as Dean relaxed a little.

The tiles were cold against Dean's forehead, the guy next to him was grunting rhythmically as his partner thrust into him, the air was thick with sweat and heat, denim dug into the sides of his knees as Eric pushed his legs further apart. In the middle of all of that was slick teasing pleasure that made Dean want to curl away and press into it at once. Too much, overwhelming, but oh, god, so fucking good that Dean wasn't sure he could bear to ever have it end. His brain shied away from the fact that some guy had his tongue in Dean's ass, but whatever doubts he had were kind of obliterated by the noises Eric was making. From the sounds of it, Dean's asshole was the elixir of the gods.

"Fuck. Steve," Eric said and Dean had no idea who he was talking about. Then he said, "Touch yourself for me," and Dean didn't care.

Because, hell, yes that was hot. Eric fucked his tongue in deeper, moans vibrating right to Dean's balls, and it was nothing like having fingers up there, or a dick. It was soft-hard-hot-wet-slippery-thick-pleasure. And it was gonna make Dean come. Like right now.

He splashed the wall and his boots, jizz ran down his fingers, and Eric did. not. stop. The sensation was too much, but somehow just right, except Dean thought his legs might give out. He was about to beg for a reprieve when Eric's grip went from tight to painful and Dean felt him shuddering against his ass.

Eric rested his head against the small of Dean's back for a moment, and then stood, pulling Dean's jeans up with him. "Thanks," he whispered and kissed Dean's neck. "Maybe I'll catch you some other time?"

Dean just nodded, still pretty much at a loss for words, his fingers busy doing up his fly.

The fifth time: Room 13, Sweet Spot Inn. (28)

A day spent interviewing 'dancers' had not put Sam or Dean in the mood for more conversation. They were hardly through the door before Sam shoved Dean face first against the wall and said, "Stay."

Dean figured Sam wouldn't mind if he moved enough to get his jeans down over his hips, so he did. Back with slick and a condom before Dean had time to miss him, Sam pushed two wet fingers in by way of prep and then got his cock up against Dean's ass.

"Don't fucking tease, you bastard," Dean said, "Fuck me." He'd been ready for Sam's cock since Misty insisted on answering his questions wearing nothing but a pair of square black glasses and while trimming what her g-string might have covered had she been wearing one. Which wasn't much. Fucking Sam was… damn, it was awesome, but girls were still girls. Nothing was gonna change that.

Sam's left arm hooked around Dean's waist and hauled him back, giving himself a better angle to get all the way in. And in he went. God. Dean still marveled at how his body made room for Sam. How Sam could fill him like that and not break him. Even when it hurt, it didn't hurt.

"I saw you looking," Sam said in Dean's ear.

"Fuck, ye—" Dean stuttered as Sam fucked in hard. "Yeah, I was. Those girls were… well, shit. You saw them."

"Thought about you fucking them. About them bending over those little dressing tables, all lined up, waiting for you. While you fucked them. One after the other."

"Shit. Sam—" Dean could see it too, like it was right there in front of him.

"You made them all come," Sam went on, "But none of them made you come. You don't come til I fuck you." His right hand slid around and started playing with Dean's cock. "Fuck you right there in front of them while they all watch."

Dean tried to agree, but it sounded more like "Gnargh" than anything. He figured Sam got the point though.

"They've all got their hands on themselves. Fingering their clits, knuckles dripping with their own juices, while they watch me fill you up with cock. Watch you flushing, dick dripping on my fingers, slicking it up so when I jerk you it's that perfect friction. They're moaning and writhing around, wishing that cock of yours was up in them again, not in my fist."

Dean caught his breath, said, "Wishing you were fucking them instead of me, but you're mine. Only mine. Only I get to feel you like that."

Sam started driving into him then, no more words, just fucking hard and fast until Dean was pressed up against the wall. Sam went rigid when he came, nearly crushing Dean's ribs, though Dean couldn't have cared less if he'd broken them.

The collar of Dean's shirt pulled tight against his throat for a minute as Sam slid down his back. Feeble hands pawed at his waist, and Sam's head nudged at his hip until Dean turned around and slumped against the wall. "Mmmm," Sam said, before swallowing his dick. The sight of himself disappearing into his brother's mouth was all Dean needed.

When he was done, he slid down the wall to the floor and let Sam lean against his chest. "Think there's any way we can work this gig so all we have to do is haunted strip-clubs?"

"Probably," Sam said, and burrowed his face into the space between Dean's shoulder and his neck.