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by astolat

"Sammy, Sammy, Sammy. You seriously don't want to know."

Sam let his head fall back against the back of the seat. He wondered why the hell he let Dean sucker him into this crap every time. "You're the one who wanted to play truth or dare!"

"We've got twelve hours of highway to go and I'm bored," Dean said.

"Yeah, bored enough to make me moon the last five truckers we passed," Sam said. "You think you're backing out now?"

"Hey, you want to know, I'll tell you. I'm just trying to save you some trauma," Dean said.

"Oh, what, was there felching involved or something?"

"Dude, gross," Dean said, making a face. "Gimme another Twizzler."

"Uh huh," Sam said, and wagged the candy just out of reach. "Start talking."

"Okay," Dean said. "So this was maybe four years back, I did a job in Lake George, met this chick at a bar that night—"

"Just one?" Sam said.

Dean smirked. "Trust me, Sammy, this one was enough."

"Let me guess," Sam said, sighing. "Tall, brunette, D-cup—" It really hadn't been worth wasting a question on this thing. Dean volunteered info about his sexploits pretty regularly, bragging about the spectacular supermodel-hot girls he'd banged, how awesome they'd been in bed. He was probably happy to have an excuse to go into loving detail. Sam had only asked because—because—because he was freaking bored out of his head too, four hundred miles from Des Moines and seven hundred to Daytona, and he hadn't been able to think of anything better.

Anyway, he was never really sure whether to believe any of it or not—well, not the pickups, he saw enough of Dean in action to buy that, but the hinting at wild orgies and sex on a higher plane of existence or whatever. He had figured Dean wouldn't bullshit him in Truth or Dare, but if it was just going to be the same old—

"Nah, maybe five-three, a little chunky, dyed blonde," Dean said, and Sam eyed him sidelong. "She cleaned me out at poker—maybe I was playing a little cocky—"

"Wow, I'm shocked," Sam said.

Dean swatted him. "Shut up, she would have had you in two hands. Anyway, she cleaned me out, and then she tried to get me to go double-or-nothing on the Impala—"

"You did not."

"Course I didn't," Dean said. "I pushed the money at her and told her it wasn't going to be the first time I slept in the backseat—"

"Uh, why didn't you just get a room on a fake card?" Sam said.

"I already had one." Dean grinned over at him unrepentantly. "But I figured saying that was a lot more likely to get me bought dinner and taken home after."

Sam rolled his eyes. Predictable.

"Anyway, so yeah, she took me to dinner, and she invited me back to her place. And man, she was cute, don't get me wrong, but I hadn't expected her to be a tiger, and whooo," Dean shook his head, smirking. "We started out the old-fashioned way once, after that she asked me if that was it or if the dial went up any higher—"

"Did she actually say that or are you making it up?"

"Whatever, she said something like that," Dean said. "Am I telling this or what?" Sam flapped his hand at Dean. "So number two was standing up, start to spectacular photo finish—"

"Dean, you remember that this is supposed to be the freakiest sex you ever had, not the best."

"I'm just getting warmed up," Dean said. "And so were we, because after number two was number three. She wanted to tie me up and spank me—"

"You let a chick you met at a bar tie you up?"

"No! Dude, quit asking stupid questions," Dean said. "I know my freaking succubus lore. But I told her I'd stay put, and that was all good with her, and after she was done, she, uh, you know," Dean coughed, "rimmed me."

"So that's it," Sam said, somewhere between relieved and disappointed. He'd expected better than something out of Jess's softcore romance novels. "A little spanking and some rimming?"

Dean grinned at him cheshire-smug, and clapped a hand on Sam's thigh. "That was day one." Then his hand twitched just a little, and he made a quick darting grab to snag the Twizzler out of Sam's hand. He stuck it in his mouth and kept on talking around it, a little faster. "Anyway, day two, we didn't wake up until around noon. I didn't have anywhere else to be, so she made me pancakes and we had a couple more rounds, and then she brought out the weed—"

"Dad so would've kicked your ass."

"It wasn't any big thing. We just mellowed out some. It was like—you know after a really good hunt with some running and some digging, after you've had a chance to get a long hot shower, some dinner, a couple of beers, where everything just kind of unwinds and you feel like you're almost gonna melt—"

"So you got completely baked," Sam said, and looked away to hide the grin he couldn't help. He didn't get that kind of high from hunting, he never had, but he still knew what Dean was talking about: he'd seen Dean fall into it plenty of times, coming home and sprawling wide over any convenient piece of furniture relaxed and dopey, jeans unbuttoned and half-unzipped, hand tucked inside shamelessly and another one making slow love to the neck of a bottle, music on low.

"—and that was when she brought out the toybox," Dean said, and Sam double-taked back at him.

"Toybox?" he said, half-skeptical. "Are we talking silk scarves and feathers here, or—"

"We're talking everything," Dean said. " She wouldn't let me see to start with, she just snuck something out of it, and then—" he paused for effect "—she deep throated me."

"Okay, and," Sam said, raising his eyebrows.

"Dude!" Dean said, irritably. "Show some freaking respect. I'm not talking like, the fake deep-throat thing where the chick's using her hand on half your cock and slurping a lot, I'm talking real porn-star, all-the-way-down, you know, when you can feel the throat muscles on your—yeah, okay, look who I'm talking to." Dean snorted. "You're just going to have to take my word for it, Sammy, this was some truly awesome head, and then she slipped in the vibrator—"

"Slipped in?" Sam said.

"It was just one of those little bullet ones," Dean said defensively. "She'd lubed it up already or something, it went right in—" and Sam belatedly got that Dean meant she'd put it in him, and stared. Dean shrugged with one shoulder and an attitude of cool, obviously obviously faked "—and she flipped it on, and bang—"

"Okay," Sam interrupted, trying to keep his voice level, because suddenly this was starting to go somewhere he didn't really want to be, "you know, I'm still not seeing a whole lot of freaky here, Dean, so if you're just turning yourself on bragging—"

"Yeah, cause I'm the only one getting turned on here," Dean said, leering. "Patience, young grasshopper. I'm still just in the setup. So anyway, there I was, three knockouts and uh, down for the count, and then she snuggled up and whispered she had this fantasy she hadn't ever had the guts to ask a guy for, and since I was just passing through—"

"You do get that she probably used that line once a week," Sam said. "Also, I really hope you were using a condom."

"Oh, we were using 'em by the box," Dean said. "She had some special ultra-thin ones from Finland or something. Awesome stuff—lubed and ribbed on the inside, so it was all slippery on—"

"So what was her fantasy," Sam said, looking out the window. He wasn't really interested anymore—sooner Dean got through with it, sooner he could call an end to the stupid game. He rubbed his palms against his thighs.

"She, uh," Dean cleared his throat a little. "Well, it was a lesbian fantasy, except she wasn't actually into chicks, so—"

"Let me guess, pegging," Sam said, his throat tight, wanting it over. He shifted his weight some on the seat; his back was starting to ache after six hours on the road.

Dean cleared his throat some more. "Well, yeah, but, uh—" The tape ran out just then, and Dean paused and started rummaging around in his tapes, practically ducking his head against Sam's thigh—

"Dude!" Sam said, bending down and yanking the box of tapes off the floor of the car and onto his lap. "Eyes on the road."

"Ow, hey," Dean said, and managed to grab a tape by feel out of the box and shoved it in. He fiddled with the dials, pretty obviously holding back for the music, so Sam waited until Creedence started blasting and shot out his hand and twisted the volume all the way down, just in time to hear Dean finish mumbling, "—like a girl."

"What?" Sam said.

"She wanted me dressed up like a girl!" Dean said loudly, and okay, Sam took it all back, it was worth having listened all this way, it was worth having suffered ten million of Dean's other sex stories, it was worth having pulled down his pants in front of the five ugliest truck drivers in Missouri, because this was possibly the single most perfect thing he had ever heard in his life.

"So you, uh," Sam said, "you got dressed up like a girl and let her—"

Dean was actually getting kind of red, a five-hours-of-sun glow on his cheeks. "Yeah, well, I'd had half a joint and I'd made it six times in twelve hours already, so—"

"Did you get off on it?" Sam interrupted. "Did you get off on her fucking you with the strap-on?" Soon as he heard his own voice, too loud, he felt hot and embarrassed saying it, except he couldn't take it back.

"Whatever," Dean said, trying for casual and falling way, way short, "actually, I got off on being all pretty," except that came out sounding sort of true, and he coughed and leaned back in his seat the full length of his arms, gas pedal going down with a grumbling roar. "I mean, she put me in this silk stuff—it just—" He stopped.

"Did you shave your legs?" Sam said.

"Well, yeah, she wanted me in a skirt, so what else was I supposed to do?" Dean said defensively. "The shaving wasn't a big deal, it's easier than shaving your face."

Sam looked down and noticed he was gripping tight on the box of tapes, veins showing puffy on the back of his forearms where his sleeves were rolled up, and he made himself relax. It was awesome. He could totally just imagine Dean, spread out in a silk skirt, little silk panties underneath with his cock shoved into them, maybe bulging out a panel of lace—maybe he'd been on his back, so she could look at his face while she did it, maybe—

"She put makeup on you?" he asked.

"Yeah," Dean muttered, and fuck, yes, he'd been on his back so she could look at his long lashes and his mouth all painted red gasping while she put it to him—

"Okay," Sam managed. "I guess that's a pretty good Truth after all. Shouldn't have doubted you."

"Yeah," Dean said, unenthusiastically, and stared straight out ahead. Then he squirmed, just a little.

"There's more?" Sam said, and goddammit, his hands kept clenching back up again—"What, did you let her do it again the next day?"

"No," Dean said, and then he put his shoulders back, like he was going into a fight. He didn't look at Sam. "The next day we got me dressed up again, and we went back to the bar," and Sam wasn't sure he was going to be able to keep breathing, because no fucking way, "and we picked up a guy together, and back at her place, we told him I was on the rag, so first he fucked her, and then," he swallowed, and his voice was rasping a little as he forced the rest out, "and then I ate her out while he fucked me."

The box of tapes had gotten dented under Sam's hands, sharp cardboard folds jabbing his fingers, and he was gripping it hard against his thighs. "He didn't notice?" he said hoarsely. "He didn't notice you had a fucking dick?"

"He, uh. He didn't take the—he didn't take them off," Dean said. "They were kind of skimpy, he just pushed the back to one side and went in. Anyway, she hadn't let him get off, I don't think he'd've cared by then."

Neither of them said another word, all twelve hours to Daytona.

They didn't really need to talk much anymore on a hunt—a nod, a hand signal, an "I'm gonna—" and they were good to go. The spectre curled up and died at the first handful of rock salt and blessed herbs, and they were back at the hotel inside two hours, big sprawling motor inn room with two king-size beds and kitchenette and sitting area, and still way too small, even though Dean parked himself on the couch by the door to sharpen his knives and Sam went out onto the postage-stamp balcony at the other end to read.

He stared at the same page for ten minutes, hearing the slow, erratic rasp of Dean's whetstone—scrape, pause pause pause, scrape instead of regular, even strokes.

It made something weird go hot and cold running along his back. He was—he was angry, that was it, he was angry that Dean had ever started the stupid fucking game, that he'd gone along with it, that he'd asked, that Dean had goddamn told him, and now—and now—Now Sam had it in his head, Dean on his knees on the bed, long smooth muscled legs braced and spread wide open with his face buried between the girl's thighs, his skirt flipped up and a thick cock shoving its way into his—

She'd have picked up a really big guy, somebody bigger than Dean; she'd have wanted somebody who could make Dean look small. She'd have gotten him worked up, wet—slicked up his cock with both hands, gotten him really hard, and then she'd laid Dean out for him. Maybe she'd helped work his cock into Dean's ass. She'd already plowed Dean once, she knew how to give it to him. And Dean just—Dean had taken it, he'd let that guy fuck him thinking he was a girl, he'd as good as been a girl, he'd spread and put out in his pretty little skirt, silky panties getting wet, and the guy hadn't—the guy hadn't found out, so Dean hadn't even gotten a handjob, he'd only been fucked, and if he'd gotten off—if he'd—

He shoved open the balcony door and went back inside and threw the book against the wall. Dean's head jerked up. "You came, didn't you?" Sam said, savagely. "You let that guy, and you—"

"Dude, it's sex," Dean said, wavering bravado in his voice. "That's the general idea—" and Sam grabbed the keys off the table and went out the door. He got back in an hour and threw the shopping bags on Dean's bed: makeup, flippy little skirt, puffy silk blouse, and a fistful of Victoria's Secret sales, pink and teal and lacy. The shower was going, fogging up the balcony doors.

Dean came out, toweling off. His legs looked paler without hair, heavy thigh muscles standing out. He was already flushed with the heat and the steam. He didn't look at Sam, just stared down at the clothes and said hoarsely, "Go wait on the balcony."

Sam went outside almost blindly, and stood at the railing gripping it with both hands. He thought about Dean's mouth, traced with lipstick, eyelashes thick and long and sooty black around his eyes, and he felt an almost painful tightening in his balls, his cock jerking, even before Dean yanked open the doors. The skirt was clingy, plastering itself to his thighs, and his cock was a smooth thick line there under it, but that wasn't what Sam was looking for. Dean's hair was too short, he still looked a little butch, but his lips stood out glossy and tinted, bow-perfect and full, waiting to be kissed, bitten, to be—Sam licked his lips and said, "I'm going to make you suck my cock first," and Dean shut his eyes and said in a strangled voice, "Holy fuck, Sam," practically swaying in the doorway, and Sam shoved him backwards into the room.

Dean grabbed the pillow off the bed and threw it on the floor and went down on his knees. Sam's hands were shaking while he yanked open his jeans and shoved them and his boxers halfway down his thighs, just far enough, and stepped up to Dean—Dean looking up at him with his pink mouth and his thick lashes. Sam wanted to kiss him so much, but first he wanted—first he pushed his cock slow and carefully into the tight ring Dean was making for him out of his mouth, smearing the perfect lipstick over his cock. Dean shut his eyes and gripped Sam's ass hard, pulling him in closer and opening for it.

"Dean," Sam said, panting. "Dean, oh God, please, get me wet, get me," and Dean slid off him and licked up the sides of his cock, mouthed wet and messy all over it, lipstick already wrecked but his mouth even redder now. He went back down on Sam again, took as much of him as he could manage, gagging a little when he kept trying to take more than he knew how.

He pulled off again, his hand still gripping Sam around the base. "You want—" Dean said, low and husky, "you want to come in my mouth?"

"Oh fuck yes," Sam said, and Dean closed his mouth over the head just in time. Sam was already going, pumping into him, short jagged pulses, and Dean swallowed and made a face and kept swallowing. Then he slid back and licked his lips—he half raised his hand to his mouth to wipe it off, and then he remembered and did it careful instead, thumb along the line of his lips fixing some of the lipstick smear, getting the little white slick at the corner. Sam watched it mesmerized, standing there wobbly, and then he sank down to his knees and took Dean's head in his hands and kissed him.

Dean kissed him back, hungry, both of them going at it hard at first, and then Sam slowed it down, slowed it down a lot, started giving Dean long tender sweet kisses, sucking at his lower lip, nibbling, licking into his mouth. Dean shuddered under his hands and tried to squirm away, but Sam held on to him and said, "Dean, shhh, let me, you're so," coaxing, nuzzling at Dean's soft smooth cheek, dropping kisses near his ear, on his jaw.

"Sam," Dean said, strangled, and turned back to let Sam kiss him some more. Sam cupped Dean's face between his hands and smoothed his thumbs over the cheekbones, blush glittering on his fingers: Dean had put a little too much on. It didn't matter, he was still beautiful, his eyes shut and his face tilted up willingly, his hands curling around Sam's shoulders and then slowly sliding down to go around his waist, pressing them closer together. Sam's cock rubbed up against the cool silky smooth of Dean's skirt, felt Dean's cock on the other side of it.

He started to get hard again, kept rubbing his hips in short little jerks against the skirt even though he was still sensitive enough to hurt. His cock nudged a little between Dean's legs. Sam gripped under Dean's ass and lifted him a little to make it easier, and drove his cock in between Dean's thighs, gloved in folds of the skirt and rubbing across Dean's cock in the panties, feeling the lace through the layer of silk. He was still kissing Dean, Dean wasn't fighting him on it anymore; Dean was hanging on to him by the shoulders and breathing hard and desperate into Sam's mouth.

"Jesus, Sam," Dean groaned, pushing himself hard against Sam's body, like he was trying to rub off against him. Sam let him do it a little, felt Dean's cock swelling, and he reached down and rubbed his fingers over where the head was making a small damp spot against his belly. Dean tipped his head back and arched against him.

"You getting wet for me?" Sam whispered, stroking him back and forth just with a knuckle, not enough to bring him off, like he was rubbing a girl's clit.

"Fuck," Dean said; he knew it: his teeth were tight on his lower lip and red staining his cheeks.

"Wait for me," Sam said, because he wanted—he had to have—

"Yeah," Dean said thickly. "Yeah, Sam, just fucking hurry," and shuddered in Sam's arms, and Sam didn't have to make him wait anymore. He hauled Dean up and they stumbled over to the bed. Dean yanked the covers back and lay down, propped up against the pillows. Mascara was smudged dark on his eyelids and to the sides of his eyes, accidentally like something out of a fashion magazine, his lips and his cheeks flushed hot.

Sam took his shirt off and got out of his jeans the rest of the way, stood naked over the bed. Dean had left everything next to the bed, creamy lube in the girly purple bottle thick on Sam's fingers, stroking over his cock. Dean watched him, breathing hard, chest rising and falling. "Dean," Sam said, and he got onto the bed, knelt between Dean's thighs and ran his hands up them, spilling the skirt away and exposing the panties. Dean half-turned his face into the pillow, eyes squeezed shut. His cock and his balls were straining against the fabric, triangle of pink lace not big enough to hold them all in, head of his cock poking out over the waistband. Sam ran his thumbs along the crease of Dean's thighs, just brushing against them.

"Come on, Sam, come the fuck on," Dean said, his jaw clenched, eyes still shut.

"Shh, hey," Sam said, softly, stroking him again. "Easy," and he slid his hands down under Dean's thighs and into the thin silky underwear, rubbed slickness over Dean's hole. Dean jerked a little. "Look at me," Sam said, and Dean took a long gasping breath and slowly opened his eyes.

Dean kept his eyes open, only occasionally letting them drift half-shut, his mouth soft and rounded for breath, while Sam pushed into him. Sam panted through it, feeling Dean stretch open around him. "God, you're gonna take it," Sam said. "Dean, you're gonna take all of it—"

"Yeah," Dean said, wide open and soft and hot under him. "Yeah, Sammy, go ahead, give it to me, want it, want—" and all of a sudden Dean was just gone, going over, shaking with it, his cock jerking and staining the silk. Sam kind of lost the next five minutes, because all he knew was he was fucking Dean crazily, rocking him back and forth into the bed, and Dean was hanging on to Sam's shoulders and making helpless moaning noises as his cock rubbed through the mess he'd made, and then—and then—

"Holy fucking shit," Dean said, vaguely, about twenty minutes later.

"Oh my God," Sam said, staring at the ceiling. He wasn't sure whether he was thrilled or horrified.

"Yeah," Dean said. He pushed himself up groggily and yanked the blouse off over his head, and wriggled out of the skirt and underwear and kicked it off the bed. "Man, that stuff itches." He lay back with an arm behind his head and sighed luxuriously. Then he farted.

"Dude!" Sam said, shoving him, if kind of feebly. "Gross."

"I'm not actually a chick," Dean said, shoving back.

"It's okay, Dean," Sam said, because he couldn't not take bait like that. "You don't have to hide your real feelings with me any—awgk—" as Dean rolled over and thumped down on top of him.

"You know," Dean said, grabbing for the lipstick on the end table, "I'm thinking maybe you want to get in touch with your inner princess yourself, Sammy—"

"No—no—Dean!" Sam squawked, grabbing for Dean's hands as Dean tried to draw on his face. Then Dean leaned down and kissed him while they were deadlocked, and then they were rolling over into the crushed sticky mess of the bed, lipstick smearing all over both of them, cocks rubbing together and Sam panted out, "Dean—Dean, I lo—"

Dean tried to cover Sam's mouth with his hand. "Dude, don't say it." Sam nipped his fingers and pulled Dean back down on top of him, and whispered it to him instead.

= End =

With many thanks to hafital, Kass, resonant, and Terri!

All feedback much appreciated!
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