Dean wasn't kinky. He wasn't. Okay, so he might have this... thing, but it wasn't anything bizarre or sick, not like those weirdos that he'd read about that wanted to dress up as stuffed animals or got off on fucking pickle jars or anything. It was just a thing. Hardly noticeable, really.
He hadn't really thought much about it at first, had mostly just figured he was doing what he had to to deal with being 15, perpetually horny, and having little to no privacy thanks to Sammy's ability to be almost constantly underfoot. Dean had jerked off when he could, but Dad tended to frown on him locking himself in the bathroom for twenty minutes at a time, so he'd had to find another solution. He'd discovered it on a road trip, of all things: lying in the backseat while Sam and Dad bickered amiably in Latin up front, Dean hadn't really meant to get off, had just intended to shift his dick to a more comfortable position, but somehow he'd ended up rubbing one out right there, spraying the inside of his boxers and jeans, and it was fucking hot, more than hot enough to make up for having to deal with the mess at the next rest stop.
He'd tried it again when they were settled into the motel, jerked off into his boxers while Sam slept just a few feet away and Dad snored on a pallet on the floor, but it was supper at the bar the next day that cemented it. There was just something about it, something so sweet and dirty and hot and perfect, and it hit every last button he'd never known he had. A few weeks of trial and error taught him the right amount of toilet paper to stuff into his boxers so he could still feel the pulses pumping out into them without soaking through to his jeans to give him away. Long shirts helped, too, and thankfully Dad didn't seem to notice when Dean took to buying his a little larger to give him some extra coverage, as well as adding another layer that he could use for camouflage if he needed to.
There were other tricks he picked up along the way, from using little shifts of his hips to help get himself off in public if he felt like it, to the incredible wonder that was Magic Fingers. Dean was 17 the first time he discovered how Magic Fingers, a plug, and his prostate could combine to make his come his brains out. With the plug in, if he spread his legs just right, the way the bed shook would fuck it up into him at the perfect angle, and sometimes he didn't even need his hand to come. He used to cut class the day after Dad left on a trip, go back to the hotel, and spend all day soaking his jeans before he had to change and go meet Sam. The few times that Sam asked, he'd admitted to cutting class and usually made it sound like there had been a girl with him.
And sometimes, there really had been. As good as Magic Fingers could be, that was nothing compared to how good it felt to fuck against the sweet wet warmth of a girl. Dean had learned fairly early on that heavy petting and dry humping could get them both off, so he rarely pushed for more, which almost certainly fed his popularity; the girls got the benefit of his bad-boy image without having to worry about being asked for things they weren't ready to give. Of course, those that were willing, he wasn't about to turn down - he wasn't stupid, after all. So he fucked the ones that offered, and played through the clothes with the rest, and if he tended to pick the good girls that wouldn't let him under their panties and he ended up dry humping them until they were both shuddering, panting messes, then that was just his luck.
The boys in high school were even better than the girls; most of them were still far enough in denial that any real action would've sent them running off, but a little making out and rubbing up against each other they could write off as no big deal, especially if they'd both been drinking or smoking a little. They were easier to deal with than the girls, too - no big emotional scenes or expectations that he'd do the boyfriend thing, just two hard dicks and horny guys, shoving up against each other until they both lost it. And while Dean loved watching girls come, seeing how their whole body just arched and shuddered, there was something even better about making a guy come in his jeans - probably because he could really see it, see the way his jeans got dark around the crotch, feel them get soaked against his hand, and fuck, he almost always followed them right over the edge when that happened.
He ended up turning to guys more and more to get his fix as he got older, mostly because the high school girls turned into women who would willingly open his legs and probably think he was a freak if he said he wanted to dry hump them like they were back in school. So Dean went for women when he was in the mood for sex, which was most of the time, but every so often, he wanted to indulge that dirty little itch at the back of his mind, and that was when he'd go looking in other places. Even at the rough roadside bars where they usually stopped, there would be one or two guys whose eyes would linger a little too long on his lips or who might get just a bit too close when they played pool. Dean was careful never to make it too obvious - no leaning over the pool table like a slut, but sidelong glances would let it be known that he was willing, and he'd ended more than one night either shoved up against a brick wall and getting dry humped within an inch of his life or kneeling in an alley, jerking off into his jeans while he blew whoever had looked good that night.
Sam never knew about any of it, mostly because Sam was gone for four fucking years, but then he came back and Dean discovered it was a lot harder to hide things from Sam than it was from Dad. Sam gave a shit, for starters, and the first night Dean had slipped out back with his pool partner, Sam had thought he'd been kidnapped again and freaked the fuck out when he found him back at the Impala. Luckily, Dean hadn't been gone that long, so he'd managed to convince Sam he'd been in the john, but it was a warning that he had to be a helluva lot more careful than he was used to being.
But then, Dean never had been big on paying attention to warnings.
He did all right for a while, but then they found the motel with the Magic Fingers, and it had been a pretty long time since he'd indulged, so as soon as Sam left to interview the latest victim, Dean stripped out of his clothes, eased the little plug he kept buried in the bottom of his bag inside, pulled his jeans back on over his bare dick, which had been hard ever since he'd seen the little control box, grabbed his wallet, and headed for the motel's office. The desk clerk smirked at him as he handed the rolls of quarters over (no way he could claim they were for laundry, not with his hardon pressing visibly against his fly) but Dean didn't care. He was going to get off big time, and that was all that mattered.
Sliding the quarter through the slot made his dick jump and he adjusted himself as he lay back, the bed starting to shake under him. A few hitches of his hips and he had the right angle, the plug inside vibrating every so slightly, a gentle buzz that he could feel through his entire crotch. Dean stroked his fingers over the hard ridge of his dick, a loud moan breaking free when the first spurt of precome dampened the denim. He teased around the wet spot, swirling one finger over his head through the thick cloth, well aware that it wasn't going to take long to come, as worked up as he was getting and as long as it had been since he'd had a chance to do more than pick up a one night stand for a straight fuck. Sure enough, he barely managed to make it through a dollar's worth of change before he was groaning and shoving up into his hand, coming in hard pulses that soaked his jeans and left him still half-hard from the dirty thrill of it.
He meant to stop there, but somehow once turned into twice, then once more, and he was working on his fourth orgasm in two hours when he heard the door open and then close. Dean realized somewhere in the back of his brain that it was probably Sam, but he was too close to stop now, his dick shoving up against wet denim as he frantically writhed about on the shaking bed, whining low in his throat when the plug wasn't moving enough. He didn't often want to get fucked, but right about now, he would've spread for it like an eager slut to get more sensation. Besides, it might not be Sam - what if the motel manager had decided to find out what he did with the Magic Fingers and wanted to join in? And if it was Sam, he'd probably just leave as quickly as he could, so either way, Dean got to come, which was all he cared about.
"God... fuck, ungh, yeah..." he groaned, shoving two fingers into his mouth to have something to suck on as he got closer. Images flashed behind his eyelids - a dick in his mouth, one in his ass, hands roving over his body... God, he was so fucking close...
His eyes flew open at that, although he wasn't sure if it was his name or the way his brother's voice sounded when he said it, strangled and harsh and deeper than usual, that yanked him out of his sensual haze. Either way, it didn't matter, because all he could manage in reply was a choked gasp, "Sammy," as he came again, unloading hot and sticky into his already soaked jeans.