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Title: Lost in the Temple of Law
Author name: Icarus
Author email: icarus_ancalion@yahoo.com
Count:
Rating: NC-17
Pairing: Sam/Transexual
Summary: There's a first time for everything, right?
DISCLAIMER: This story is just written for fun. The characters and universe contained in this story are copyright Kripke and Co. What belongs to me are the words and of course, any original characters, et al. Copyright © 2007 All rights reserved. Only the original ideas contained within the works on this nonprofit web site are the property of their authors, and please do not copy these stories to any other website or archive or print without permission of the author. Ask, guys. I'm easy to reach and usually generous.
Author notes: Thank you to Emeraldsword and Pxr5. I have been officially lured to the dark side.

~~~~~~~~~~~~~


Lost in the Temple of Law
By Icarus

The atmosphere in the bar was dense and smoky, smelling of beer, wood, and overripe sweat. Sam didn't quite smile as he straightened his jacket, but stepping through those doors made something in him settle and feel lighter, like coming home. And how screwed up did his childhood have to be for a skeevy bar like this to remind him of home? But he could almost picture his dad brooding over a drink at the far end (he'd sit near the exit), a high shine to his cheeks saying he'd had one too many; Dean next to him with both elbows on the bar, chatting up an amused woman twice his age.

Sam swept the mop of his bangs off his face. He just needed a break from his first quarter at Stanford, that's all, the same way the Asian exchange students needed to band together and speak their own language for a while, head into Chinatown and whine about America.

Sam knew his childhood had been bad, of course; who wouldn't? But he was coming to terms with just how bad, in a thousand tiny ways. Today all it took was his roommate complaining about changing the cat litter for it to slam home that, hey, I never had a pet, and by the way, it really was never an option, and also, I can't tell you any of this because you'll want to know why.

So without much explanation or idea of where he was going, Sam had stepped onto a bus and got as far as he could from middle America and classmates who assumed he was normal. Only when he reached a run-down neighborhood, where people squinted at him out of the corner of their eyes and pretended they hadn't, did he finally relax, his unused reflexes and normal edge of caution jumping back to life. He was a gangly six foot four these days so most people kept their distance. The bus hissed as he got off and, like any bad neighborhood, the nearest bar was only a block or two from the next bar.

The regulars glanced in his direction and then ignored him, returning to their conversations. An old fashioned jukebox sat against one wall, a 1960s hit warring with the sound of the TV basketball game above the bar. Signaling the bartender, it occurred to Sam that this was the first time he'd been in a place like this without either his brother or his dad. He'd made his own fake I.D. -- he was underage for California -- but of course the bartender here didn't ask. Heck, they'd let him into places like this when he was nine.

A leggy brunette smoking a cigarette gave him a long questioning stare, her eyes sparkling. Sam looked away with a smile and an embarrassed chuckle.

Okay, this was different. Usually the women draped themselves over his older brother and ignored Sam. He accepted his beer and buried his face in it, glancing up at her over the rim. She gave him a broad obvious wink. Sam looked down immediately.

Out of the corner of his eye, he saw her slide off the barstool, swinging her hips as she came his way. When he finally gave in and looked again, he realized she was tall, easily as tall as he was in her spiked heels, and maybe 5' 11" or even six feet without them. He liked it. Also, by the lines in her heavy make up she was quite a bit older than him. Thirty, maybe thirty-five?

She smelled like too much perfume and a metallic whiff of hairspray wafted over when she took the seat next to him. Her short skirt rode up as she sat with her legs slightly parted before crossing them. Sam forced himself meet her eyes instead when he realized he was staring up those long legs to....

But she didn't seem to mind, just asked in a deep smoker's voice, "What's your name, hon?"

"Um." Sam blinked, deciding that maybe Dean had been a distraction for women all along. "Sam."

She leaned in close and said warmly, "Hi, Sam." The edge of a black lace bra showed around the rim of her blouse. She was built and knew it, smiling devilishly at him as his eyes came back up. He tried not to blush.

He didn't have a cheesy line for her like Dean would and his mind caught at the air, trying to think what to say. He finally just asked her name feeling he was in, like, third grade. He berated himself inwardly, mocking: Hi. I'm Sam. What's your name? Lila? Oh. Want to play with my toy truck?

He turned towards her, intent, and of course that's when his elbow hit the bar. "Ow, sorry." He had no idea why he was apologizing to her for hitting his own elbow.

Yet somehow she hadn't figured out that he was an idiot, and he gave her a smile. Scratching the back of his head he asked her what she did for a living – and then they were okay. She went on for a while about her job at a railroad, and that was interesting because he couldn't picture her working in such a rough environment. He said so.

He was sure she was flirting with him when she asked where he thought she should work. He looked up at the ceiling, laughed, and tried to come up with something complimentary. He decided just to be honest. "I can see you running things. In some business somewhere."

She looked surprised. "And why's that?"

"I dunno. Most women get walked on but I don't think you would."

She lifted an eyebrow, and then raised her glass in a toast. "Maybe I'm not like other girls."

One of the guys at the bar choked and she shot him a glare. And Sam realized he'd just scored points with her without even trying. He made a mental note, erasing a whole list of things that his brother had told him about women that he always knew weren't true.

But she'd now switched the conversation back to him, trying to draw him out. Well, what could he say? He stuck with college, depressed that she'd expect him to be normal, too.

As expected, she was impressed. "A college boy. Stanford, no less."

He barely caught himself before he mentioned he was only in his first semester, glancing at the bartender. Only a few months out of hunting and he'd already forgotten to lie. He thought it was a good sign. He had to admit, he was enjoying himself, just a little bit.

One of the regulars down the bar said, "Leave the kid alone, Lila."

"Get out, motherfucker," she said. And on second thought it wasn't surprising she worked at a railroad. Sam smothered a startled laugh. "The 'kid,' as you term him, is called Sam. And he's plenty old enough to decide for himself." She turned to him, her head held high. "Aren't you, honey?"

"Yes," Sam said, grateful. He was totally sick of being patronized. By his dad, his brother, teachers, friends who couldn't believe he'd missed all the hit TV shows and the junior prom....

The guy rolled his eyes and looked away.

They talked a while about nothing, edging closer together as it grew dark outside. Sam leaned his elbow on the bar and Lila's drink was only inches away. Her legs uncrossed as she flipped her hair back, her voice a deep hum, her lipstick red, eye makeup overdone although she had very pretty brown eyes. When she recrossed her legs, her thigh was between his knees. Her foot came up and briefly stroked his calf almost as if by accident. He was sure it wasn't. They forgot to talk a moment.

Finally she said in a hungry voice, "Come home with me, Sam."

Sam's mouth opened, but no sound came out, which was good because all he could think was Uh.... He had never... Dean always made fun of him because he hadn't. But he wanted to. Bad. Sam just nodded, licking his lips.

There was a first time for everything, right?

She drove a pick-up truck, the expensive kind with a huge cab, high enough off the ground that even Sam had to step up into it. He checked automatically for a gun rack behind him before he shut the door, but no. Nothing more than a set of Macy's bags. He'd been hunting too many years to ever fully relax.

She turned the key in the ignition – and wow, it looked strange to see high heels pump the clutch, shifting to the gas pedal once she released the emergency break -- and the radio came on, blasting Jimi Hendrix.

"Oops," she said. She shut it off, looking chagrined.

"No, really, it's okay. I like Hendrix," Sam lied, and gave her a tight smile.

When they reached her house, he upgraded his estimation of her age by about five years to forty. The neighborhood was nice, the kind that made Dean uncomfortable, with landscaped yards that lit the plants with track lighting and new cars parked all along the street. Sam wondered what the heck she was doing in that crappy bar. They'd driven further than he would have expected, too, although people had talked to her like she was a regular. Sam gave her an appraising glance, wondering what her story was.

"Well. Here we are," she said.

She caught him off guard when she grabbed the two empty trashcans at the curb and started dragging them behind her. Shrugging to himself, he played the gentleman and took over. He settled them next to the garage while she hunted for her keys in her handbag.

She held the door for him, waving him in. "Make yourself comfortable," she said.

Hands in his pockets, suddenly intimidated to be inside a woman's house, Sam looked around her place. It was... functional. There was a set of muddy work boots under a coat rack just inside the door. Simple prints of sailboats hung on paneled walls, and the furniture was out of the 70s. There was a long banister leading upstairs. She moved some coats so he could hang up his own jacket, and he noticed that all the ones hanging there were men's coats.

It occurred to him that she might be married.

Used to hunts, Sam's eyes narrowed and he plastered on a false smile as he eased off his coat. Dean wouldn't care if she were married -- Probably wouldn't, Sam amended to himself -- but Sam did. He began checking around for other signs of a couple. Double sets of car keys on the key rack. Family photos. Clothes that were definitely a different size. Or a table set for two. But the kitchen table had only one chair pulled askew, a pile of newspapers stacked on the chair beside it. There was a single cereal bowl soaking in the sink. And all the coats looked the same size, though since they were different styles it was hard to tell.

Sam asked anyway, swinging his arms, "So. You got any roommates?"

"Oh, thank god, no," she said in her smoky, throaty voice. She stepped closer and put her hands on his hips, pulling him close. "Unless you count tonight."

Her eyes were really dark brown and she was giving him a knowing look as she cupped his ass. Her hands were strong and Sam had to let out a breath. His smile turned real, though he looked down at the floor, squirming with embarrassment. She ran her hands up his back, sliding under his shirt and, whoa, this was fast. Sam murmured into her hair anyway, though he was fast losing control of this, "You ever been married?"

Like she'd tell him, he berated himself. He was out of practice.

"Sadly, no," she said, and it sounded genuine. Sometimes a point-blank question worked. Sam had heard enough people lie in his life that he was fairly sure when he heard the truth. "I guess I never found the right man."

She tipped her head up, just a fraction to meet Sam's lips, and then they were kissing.

One arm wrapped around his shoulder, her other hand sliding down the back of his jeans, their breathing shuddering. He didn't know where to put his hands and she pushed him back a step, the kiss turning hotter. She opened the button of his jeans while he stroked across the solid play of muscles on her back, seeking bare skin, and Jesus, what did she do at that railroad? Stack railroad ties?

She glided his zipper down with a slow rasp and he arched forward into her hand when she cupped him through his underwear. His mouth slid off to gasp and say, "Shouldn't we... shouldn't we try this upstairs?"

She gave him another squeeze, her eyes heavy-lidded, and said, "I thought you'd never ask." She flicked her eyebrows, "Big boy."

Sam's head dropped. He snickered, his smile bright.

She tipped his chin up with her hand, then stroked down his cheek with a forefinger as she asked, "You sure about this, hon?" Studying him.

"Uh, yeah," Sam breathed, the word half a laugh. Stupid question.

And with that he followed her up the steps, watching her hips swing. He wished he'd had the presence of mind to unzip her blouse. And he was never teasing Dean about taking women home from bars again because this was great.

Upstairs, her bed was unmade, the walls here also paneled. A men's shirt hung on a hanger off an wrought iron vanity where makeup was scattered and left out in front of the mirror. He saw himself in the vanity mirror out of the corner of his eye as he reached for her. She met him halfway and then they were kissing again, her hand sliding his shirt up. He turned her around as they stripped off his shirt and undershirt, peeking so he could watch when he pulled down the zipper of her blouse, getting even harder as the back of her black bra was exposed.

She dragged him over to the bed and sat on it, shoving rumpled blankets aside. She tugged him down onto her lap, his legs straddled over her, and Sam realized she was big enough for him to do that, to hold his weight, his mind doing a little flip. Then she grabbed his hips to grind up into him, head tipped back as she groaned, low and deep.

She arched at a different angle, hands sliding to squeeze his ass as she circled, her teeth gritted -- and that's when he felt it.

"What the hell?" Sam shoved away.

She was pushed back on the bed onto her elbows, breathing heavily as she asked, "What?"

And Sam, his mouth hanging open in astonishment, added up all the cues. The men's shirt. The coats. The pick-up. How tall she was. Her low, smoky voice. Her back... he'd been touching her back.

He looked her up and down -- and how screwed up was it he couldn't switch pronouns? -- the curve of her hips, the totally perfect legs that he could see now were in thigh highs, her obvious cleavage, and couldn't wrap his mind around it.

He shook his head and made an inarticulate noise. His pants were undone in front of a guy. Who'd been groping him.

Her shoulders sagged and she looked away with a self-deprecating snort. "I knew this was too easy," she said in a voice that was definitely a guy's now.

Sam's mouth opened and closed, before he managed to say, the words coming out on a shaky laugh, "I-- I'm sorry, I thought ... I mean, those look ..." He gestured helplessly to her chest.

"What?" she asked challengingly, that same defiant chin he'd seen in the bar.

"It didn't feel like a stuffed bra."

She laughed. "Oh, they're real, honey." When Sam raised his eyebrows doubtfully at her, she said, "Hormones. And maybe a little silicone."

"Maybe a lot of silicone," Sam said.

She snickered and got up, hips swaying gracefully, her blouse still undone, bra strap showing as she passed him to stand in front of the vanity. She took off her earrings and shook her head. Sam stared, fascinated, unable to get over it. She looked... real.

He noticed the round Styrofoam head on the vanity and realized what it must be for, though he asked anyway. "Is that really your hair?"

She smiled. "My hair's long, but not that long." She set the earrings in a little jewelry box.

He waited, expectant. It was crazy, okay, maybe. But he wanted to see.

She looked over at him, long lashes thick with mascara as she blinked. "You want me to take my wig off?" she said with a note of surprise.

Sam swallowed, then nodded.

She tipped her head to the side, rolling her eyes a little like he was the weirdest person on the planet, and Dean had had that expression so often that it seemed it was a unanimous conclusion from the universe. But Sam just waited.

She sat down on the vanity stool, grabbed the side by her ear, and pulled it off.

Her hair was up in tiny tight little bobby pins. It did not look nice. She had a slightly receding hairline, though it was a dusky brown, the same color as her hair in the bar. Sam liked that, the fact that this much was genuine. But the bobby pins had to go.

He reached over, hesitating, then pulled one out. It was very tight and he had to give a little tug, unwinding and then finger combing the lock of hair which was soft and came nearly to her shoulder. He stood behind her and watched in the mirror as she started in on the other side. Measuring with his eyes, he decided to start on the bottom front and work his way up and back.

They worked for several minutes in silence, his hand brushing her shoulder sometimes as he stroked out her hair. Bobby pins clicked and bounced as they dropped to the table. Her natural hair was curly and fluffy, like an afro almost, and felt better than the wig. Smelled better, too. Clean. No hairspray.

He smiled and joked softly in her ear as he fluffed it, "You need a disco ball."

"Ha, ha, like I've never heard that before," she said.

He could see down the front of her shirt from this angle and he licked his lips. It was still unzipped, too.

She followed his gaze. "You gonna help me with this?"

Sam nodded. Oh, yeah. This he had to see.

He slid the top off her shoulders. It caught on her breasts so he had to lean forward and peel it down. She had on a black lace bra that seemed almost too small to hold all of her, and he could see a wide dark nipple through the fabric. He shifted where he stood. He checked out the other side, which was the same, and the same soft curve. Her chest rose and fell, jiggling a little.

He fumbled at the back of the bra strap. It was stuck so he tried some more force. He winced as she frowned at him, and then he finally got it. Man, these things were made like Fort Knox.

He slipped it forward and, oh, God. There she was. Very full. And yep, real. Too real.

He didn't ask, just reached over and touched her. Gathering them in his hands, running his thumb over her soft, wide nipple. He looked up at the mirror to see them from the front, see himself doing this. He was taller than her by a couple inches, his eyes bright.

"Cup them from underneath," she urged him, and he did. They were sweaty on the underside and so firm as he squeezed, her frizzy hair in his face as he watched them.

She inclined her head towards him. "You ready for the rest?"

That sounded like a dare.

"You first," she said.

And Sam blanked for a moment. She nodded with her chin to his jeans, which were still open he realized.

"It's your turn."

He looked at her sideways, considering. Well. Fair was fair. He stripped down his jeans, stepping out of them.

He spread his arms in a broad okay, so here I am shrug as he stood there in black socks and white briefs. He looked ridiculous, he was sure, but she'd asked.

She leaned her chin on her fist, still half-naked -- Sam goggled -- then she made a little spinning gesture with her finger for him to turn around.

With a snort of laughter becoming a smile he turned, feeling like a piece of meat on display as she devoured him with her eyes. He could see himself in the mirror over her shoulder and he had to admit, other than the stupid black socks, well, he looked good. Not as big as he got when he was hunting, but no string bean either. His smile was a little smug once he put his hands on his hips and finished the circle.

"Very nice, college boy," she said in that smoky dark voice.

Then she stood, and shimmied the skirt down to pool at her feet. Black thigh-highs and smooth legs, and Sam swallowed. She had on black underwear, and yeah, there was a bulge in front, but it didn't really register.

Then with a dangerous smirk she pulled the underwear down, and curving down with it....

Sam rolled his eyes and turned away, but the image of a hard cock curving downward, almost no hair around the balls, thick all the way up the shaft, was burned into his brain. He sat down on the bed and hid his face in his hands. "Oh my god. I don't believe it."

"You boys never do," she said.

It had curved a little to the right, god, he couldn't get the image out of his mind. So he looked up at her face and tits instead. Though his gaze kept slipping lower. He blinked rapidly and sat on the bed. "How did you--? Why?"

She brushed past him and said, "Okay. You've had your peep show. Now run along little boy, because if I'm not getting some loving tonight, my friend and I need some alone time." And Sam laughed a bit, because Lila had her dick in her hands as she bent over the dressing table, pawing through clutter in a bedside drawer.

She pulled out a king-sized bottle of lube and a couple condoms, dropped them on the bed, then tied her hair up in a pony tail, ignoring him. He started grinning, shaking his head in disbelief, elbows leaned forward on his knees. He wondered if anything like this had ever happened to Dean. Except Dean would have punched her as soon as he found she was a guy, then cut and run.

Sam's eyes flicked to the condoms. Two. And.... "You don't need those for yourself," he said.

"Nope."

Sam's eyebrows raised. "Expecting company?"

"You haven't left yet."

And, no, he hadn't. Dean wouldn't have wanted to know what she truly looked like either. But Sam had more questions bubbling over. He had never met anyone who'd done this to themselves.

"Why didn't you... go all the way?" Sam breathed, looking down her body, eyes stopping where it got awkward and blinking away.

"Would you?" she asked pointedly.

He cringed. "Um, yeah. No way."

"Neither would I."

"But why would you, um," he paused, to think of how to phrase this delicately. He looked up at the ceiling as he thought this through. "I mean. Did you feel you were always a woman inside? Or... was it somehow a way to accept your sexual preferences, or am I... stop me if I'm getting warm here."

Turned out she wasn't listening. "I could go down on you," she said with an eager breath. "It would be just like a girl, that's all you'd see. Only I'm much better, honey."

"Um...." Sam leaned away.

"We can use one of these." She held up a foil-wrapped condom.

Sam frowned and wrinkled his nose. "Wouldn't that taste like a hospital glove?"

Her smile turned dark as she stood. "It would be perfectly safe. You wouldn't have to risk catching anything from an old faggot."

Sam's mouth fell open, offended. "I didn't call you a faggot." The word came out of him with a moue of distaste.

"But I am old?" she noted with one hand on her hip.

Sam licked his lips and said, eyebrows raised dangerously, jaw tight, "It's not fair of you to trap me into insulting you."

She seemed taken aback a moment. Then she held up the condom, undeterred. "So, no to these?"

"Well, um...."

It looked like he was getting a blowjob.

That had been a vague part of the original plan, of course, one of those half-formed hopes back at the bar, but not quite like this. She sank to her knees on the shag carpet and parted his thighs. She shifted his underwear aside, sliding his dick out. He was flaccid, though he couldn't tell if it was from the situation, the fact that he knew this was a guy, or if it was because she'd just pissed him off and that was never a turn on for him.

She cradled his limp dick in her hand and nuzzled it, looking up at him through thick lashes and dark plum eyeshadow, strands of her hair falling into her face. She was right. From this angle she did look like a woman, her pendulous breasts shaking a little as her hair fell forward, her lipstick already smeared. She cupped his balls and licked the tip of his cock, her tongue flicking.

She turned to nibble the inside of his thigh and Sam felt his muscles jump as her cool, slightly damp hair slid over his sensitive dick. She spread his legs wider and tongued at the crease between his ass and his thigh, hot breath teasing down to the base of Sam's spine. Sam leaned back, swallowing a sigh, watching under half-lidded eyes. Her smooth cheek brushed along his cock as she turned to do the same to his other thigh, and he arched forward because she was neglecting something very important and he was definitely getting hard now. But she ran the tip of her tongue behind his balls instead, like she was going to lick... further down.

Sam's eyes widened at his totally unexpected reaction to that, even as he prayed he was clean down there. He rolled his eyes at the ceiling in gratitude when she returned to his cock, which was now arching towards his stomach.

She wrapped her big hand around him and pulled, then dragged him to her lips... and he slid into wet, tight heat.

Sam moaned as he lay all the way back on the bed, eyes closed. He was fairly sure he was being deep throated. This was no high school blowjob. He writhed rhythmically as he felt her mouth work him all the way down, his chest rising and falling with gasps. He reached out and gently, tentatively touched her hair as she bobbed, her tongue working his slit. Sam breathed harder, sliding his cock in her mouth, and moaned as he found a slow undulating rhythm, her tongue gliding down, suction tight around him. Sam's mouth fell open and his hands gripped her hair as she sped up. She slid him out, the cool air hitting his wet cock, then she dove back down, her palm reaching under to cup and knead his balls. His eyes slit open, watching her breasts shift, the wide base of his cock between her lips, the smear of lipstick at the corner.

"C'mon, get up," Sam said, thinking of her knees on the floor. That couldn't be comfortable. "Get up on the bed." He tugged on her a little.

She pulled off. "But you'll see me." Her voice was hoarse from swallowing around him.

"That's okay," he said with a toothy smile. He edged back on the sheets until his head found the pillow. He sighed in relief, relaxing. That was much better.

She climbed up, giving him a doubtful heated look, and yeah, he could see everything. Her large swaying breasts hanging down and he – Lila – was not very big, but he was very hard. It occurred to Sam that he'd gone to college to lead a normal life and now, two months later, he was in bed with a transexual. He choked on a laugh. My life is insane, he thought. He rubbed his eyes and gave in to weak snickering, like the world had played a practical joke on him.

"You see my dick. Then you start laughing. This is not turning me on," Lila sniped. "You were ready to come, too," she grumbled.

"In that big of a hurry to get rid of me?"

She shoved at his chest. Hard. He thought it was going to bruise.

"If you keep laughing, I will be."

"Sorry, it's just...." He waved a hand at the whole house, the bar, Stanford, his life. "If my brother ever found out about this...." He shook his head.

"He'd kick your ass?"

"He'd kick your ass, probably. Me, on the other hand? I'd never hear the end of it," Sam said. He trailed his hand across the decorative headboard, feeling the bumps of the carvings.

She reached for his cock and stroked, and Sam let his head fall back to the pillow. He shut his eyes. It felt good, and he smiled, feeling a weight lift from his shoulders for reasons he couldn't fathom.

"You like pissing off your brother?" she said.

No. "It's... complicated."

Her hand didn't feel at all like a woman's, hard and strong and pretty big. With his eyes closed, her breathing didn't sound like a woman's either. He slit his eyes open and peered down past her breasts to her dick.

What was the point of pretending she was something else? He slipped his hand down and, gingerly, gripped it, feeling it warm and solid in his palm.

She paused, seeming uncertain, surprised, and he moved it closer to his own cock, wrapping his hand around both. This is where he was, right now

He stroked, feeling the elongated pressure of another cock squeezed against his own, and exhaled. She dipped down and kissed him, quieter and more hesitant than before. They pressed together and he brought his other hand up in her fluffy, soft hair, trying to stroke between them, feeling fragile, like he didn't know what he was doing. He was far off the map of his experience. "I don't know if I know how to do this," he said. He broke away and licked his lips, chin dipped down.

"You're doing great, baby," she breathed, ecstatic, her mouth inches from his.

So he kissed her again, his neck leaned off the pillow, delving deep into her mouth. Then realized he'd forgotten to move his hand again, trying to both at the same time. He cringed. This multi-tasking during sex wasn't easy.

She edged his legs further up onto the bed, until both knees were up, exposing him. Or at least he felt exposed, his heart thumping in his chest. Embarrassed, he experimentally rubbed his balls against the base of her cock. It felt... well, like not much of anything. A tease.

"You sure now?" she asked him. Again. It seemed like he'd heard that question a lot tonight.

Sam rolled his eyes. He'd already gotten the point of his position. He might be... oh, unfamiliar... with all this, but he wasn't exactly stupid.

"You can do me if you like," she offered, dipping her head to lave warm kisses down his chest. And Sam found his breathing had quickened.

That would be a lot like what he could get anywhere. But it was also what he had wanted in the first place....

Sam blinked through the possibilities, then shook his head, lifting her face, unable to explain it. Or rather, he didn't know how to say it without this turning into an argument. Maybe if it weren't his first time with a woman ... but, although he wanted this, he really did, he didn't want to be thinking of it in the future when he was with a girl. Comparing. He wanted that to be special, different, its own thing.

He licked the inside of his lip and carefully kept it simple, wondering if that counted as a lie. "No. Like this." And he slipped his feet higher with a little squirm.

Lila's eyebrows went all the way up even as she tipped her head in doubtful surprise. "Okay," she said, drawing out the syllable. Weird how much she reminded him of Dean there. Sam decided Dean's working class sensibilities and language was a lot like hers. She did work at a railroad after all.

She tore the packet on the condom and slid it on, eyelashes fluttering. She arched her back, breasts out as she did it.

"So. What do I do?" Sam asked. He folded his hands behind his head.

"Lie back and think of England," she joked, and Sam laughed. Strangely, joking around made him harder. He edged his hips forward on the bed, his thigh falling open naturally. He watched her, smiling. He realized he should probably be upset or freaked out by this, but he wasn't. He had no idea why.

"I'm going to--" she started to say, but he'd already grasped the concept behind the lube she was squeezing onto her fingers. "Good idea," he interrupted.

"You sure you've never done this before?" She shook her head with a snort of laughter. The lube was cold and he flinched.

"Positive." He frowned suddenly, lips pursed in worry. "I'm, uh, I'm clean down there, aren't I?" His forehead creased as he peered up at her with one eye.

"You're fine," she said. Which wasn't quite the unequivocal "yes" he'd been hoping for, but if she could handle it....

He hadn't expected fingers actually inside him, however, and wasn't sure he enjoyed the hard, intruding knuckles, though given something much larger was going in there he got why it was a good idea.

"Now you looked pissed off." She stopped, one finger buried at a particularly uncomfortable angle.

Sam pressed his lips together and shook his head. Smiled back firmly. "No. Everything's cool."

She shrugged with one shoulder, a gesture that did mesmerizing things to her breasts and Sam froze, arching his chest as those fingers went in easier.

Huh. Interesting. Being turned on helped this part. He blinked and reminded himself that being turned on likely helped all sex.

He watched her mouth, the way the tip of her tongue traced her lower lip, and the sultry sidelong glances she gave him, checking out his body. The looks she gave him almost purred. The red smear of her lipstick reminded him of just how that had happened, her mouth on his cock, the sight of her between his legs – and okay, that worked. He felt how smoothly her hand went in now.

Her eyes went up to his face and she gave a sideways smile.

She pulled it out, which meant... uh-oh. She sidled up closer. He blinked down his chest and stomach to a guy's... she was still wearing her black lace panties, a hard cock pulled out around them, flushed and darker than the rest of her skin, circumcised and smooth.

He wasn't ready for this. Sam clutched the headboard over his head. That was a cock -- a guy's dick -- forced against him, squeezing inside. And even though it hadn't looked very big before, it was huge, and going where a dick was obviously never, ever meant to go. What the hell had he been thinking? He wasn't gay! Did he so desperately want sex that he was willing to get it anywhere? He'd accused Dean of that often enough. It seemed like he was no less guilty.

He grabbed her shoulder.

"Ow. Man, you've got a grip," she said, stopping. "What's wrong?"

What was wrong? Sam choked on how much was wrong. The manifold levels and layers and facets of it boggled the mind. "I don't know," he said, discovering that that was the truth.

She spluttered, slumping above him. "You straight boys are obnoxious."

What?

"What?" Sam said. "You think I'm straight." And the fact that the whole question hadn't even occurred to him till now, either way, perplexed him.

Her whole body shook as she chuckled, sagging against this chest, her breasts a cushion between them. At that moment, she was back to looking like a girl. With the sole exception of that dick buried in his ass, of course.

"Either that, or you're the most nervous virgin I've ever seen," she said.

"You can tell?"

He wondered if it had been plastered across his face the entire night at the bar, and cringed.

"Don't worry." She stroked his jaw with her thumb. "I won't throw you out."

He gave her a small frown.

"I was considering it a minute ago." Her thumb returned to trace his lips, which felt small and soft under her touch.

Sam blinked at her. "Yeah, okay. I get that." He relaxed, breathing out, staring up at the ceiling. A cobweb fluttered off an air vent. "I just need time to think...."

"Jesus. You think way too much," Lila said in his very masculine voice, suddenly not playing with him. Channeling Dean again.

No one could understand. How it was Sam's job to do the thinking for his family, how he had to be every bit as smart as he could, or they'd be dead. It was tough for a little kid to keep up with two experienced hunters. His dad turned it off with his drinking, and Dean had sex, but Sam, well, Sam never could.

"I've been told that before," Sam said with a wry flinch.

This wasn't Dean though. Nothing in his life since he'd left had had anything to do with his family. If Dean had been at that bar with him, he would have protected Sam from this, told Lila to get lost. Muttered about freaks and weirdoes. And Sam would have gone along with it, picking his battles. Sam cupped both his hands around her face and drew her down into a long, open-mouthed kiss. "Yeah, do it," he breathed into the space between them when he let go.

"I'm not asking if you're sure, because I swear, I don't want to know anymore," she said with a slicing gesture.

"No. I mean it," he said, earnestly. And added with a small, mischievous look. "I mean, while you're down there...."

Lila didn't wait for an engraved invitation.

His eyes widened, his breath forced out in a rush. Intellectually, he understood that he'd had time to adjust while they were talking, but he still didn't expect it to feel... not good yet, but this had potential. With a steady rocking, Sam recognized she was being gentle as he breathed through his mouth, gasping, looking up at her face, amazed. She had her teeth gritted, eyes closed, her jaw too strong for a woman, really, skin coarse under the veneer of make-up.

He sank into it, letting the experience build. He lifted his legs a little higher for that better angle, grateful he still had his socks on, hooking his ankles over her back. That jolt of heat as he discovered something that worked for both of them. Lila met his eyes, smiled, and sped up.

Then it started to burn, and hurt, and feel really good all at once.

Sam lifted his chin and gasped. He let go of the headboard and draped his hands over her moving shoulders. She bent down and kissed him, a light peck on the mouth, and he started laughing with disbelief -- because he'd looked down, and saw her tits bouncing as she fucked him. He kissed her deeper to shut up any potential complaints, wrapping his arms and legs around her. With his thighs he slowed her insistent stroking inside him to a pace he found he liked, stretching the burn, slow and gasping and deep, then released her with a pointed look.

She ignored him and sped up again, though he understood a moment later as she murmured nonsense words, her breaths coming deep, lifting up on her arms. She rocked him backwards an inch, losing control, and he made a wild grab for the headboard, his other hand gripping her shoulder as she hammered into him, hard, several times. He felt his legs bounce and felt ridiculous.

She arched her neck, clearly outlining her Adam's apple, and from her pained expression, eyes rolled back, Sam realized that he'd just watched another guy come. He blinked inwardly and couldn't quite process the information.

"Keep going," Sam said, twisting. That hadn't been enough. His ass burned and tingled but was just on the edge of something great, he could tell.

"Sorry, babe. The manufacturer's warranty has run out on the hardware," she said, gasping over him. She'd stopped moving and sweat had smeared her make-up. Her blush was almost gone, and yes, he could feel her – him – going soft as she slid out. "I'm not as young as I used to be."

That was disappointing, kind of, though he could understand. He wondered if they could continue with the blowjob.

She stretched over him, reaching for the bedside drawer. He'd assumed she was reaching for cigarettes, or some other movie cliche – after all, most of what he knew about sex had come from the movies.

She drew out a long, black dildo. Life-like, if slightly larger than life-size. Sam's eyes grew huge.

"Don't worry. Gilbert here never fails to please."

Sam coughed a laugh, his eyebrows raising into his hairline. "'Gilbert'?"

"If you're gonna have him in you, you better know his name," she said. She held it up. "Say 'hi,' Sam."

Cracking up, Sam said, "Um, hi...."

She mouthed it, so he continued, slowly, "...Gilbert."

"Good. I think the two of you are going to get along just fine," she said as she rustled down the sheets.

"You know, uh, I didn't exactly volunteer for a three-way," Sam said. Fingers were probing, circling, in his now too-sensitive ass, and he figured that he was never going to like that. He squirmed.

"I have a feeling you didn't volunteer for a lot of this."

True.

At that point, Sam heard the snap of the cap on the bottle of lube, a sound which made him break into a cold sweat, from the associations this evening. He marveled at how fast those had formed, his breathing turning shallow as his mind took a quick detour through adrenaline research and its connection with the strength of memories. He blinked those thoughts away and came back to the present, where a very large dildo was having a condom slipped on, then warmed and slicked with oil, turning shiny-black and wet.

"Um. Can I go with 'Gil'?" Sam asked, a strange look on his face. His elbows sank into the pillow as he lifted up to watch.

"Gil's not very hot," Lila complained.

Sam managed to say through a splutter of laughter, "And Gilbert is?"

Lila blushed and admitted, "There's a little bit of history with that."

Ah.

Now normally, Sam would ask her about that -- ex-lover? Porn star? The one that got away maybe? -- he liked people and was already curious about her. But at the moment, a very firm black dildo was sliding down the crack of his ass, finding his hole easily.

Sam hated to look like an idiot. Blinking, he was hyper-aware that this had to look stupid as he spread his legs for an inanimate object. It shouldn't be sexy. But on the other hand, Dean never seemed to mind making a fool of himself as long as it felt good, so Sam decided to take his cue from Dean, just this once. Because this did. He let himself relax back against the pillow as it slid in. He might have even moaned. Filling him, squeezed against him in a way that Lila hadn't. He decided that if he ever did this again, which he totally wouldn't -- but if he ever did, he would look for someone a little bigger than her. No offence.

The dildo glided back in, and out, with a wet sound, and this time Sam did moan. Lila leaned on one elbow next to him, her faced lined with concentration. Sam melted into the pillow, canting his hips a little higher, and his eyebrows flicked up as that started to... whoa. He licked his lips and pressed back against it, panting through his mouth. He shut his eyes and got a rhythm going, slow heat starting to build. Lila shifted the angle and yeah, oh, that was it. He reached down and started to beat off, but Lila brushed his hand away and then her hot, wet mouth surrounded him again.

He was so startled, he lost his rhythm for a moment. Then he shut his eyes again and went for it. He wanted to play with her clit, then realized she didn't have one, so he stroked his hand down her hip and cupped her ass, squeezing and kneading. He slid the tip of his finger into her hole and imagined fucking her, pressing his cock up into her mouth as she found that steady, fast rhythm that worked for him. He grit his teeth, squeezing around the insistent pressure inside him as he came, smothering his groan, feeling her mouth work around him as she swallowed.

Sam lay back on the bed, gasping and stunned. Fairly sure that he had just topped the kinkiest thing Dean had ever done. By, like, a factor of ten.

"You can make more noise than that," she said, sounding smug and self-satisfied. "No one's going to hear you." Sam shut his eyes as she started to pull the dildo out. He blinked. Why did it feel larger now?

He shook his head once he caught up with what she'd said. "No. I grew up in hotel rooms with my brother. You couldn't make a sound." And that was more than he had ever intended to tell anyone about his childhood. He put his hand on his forehead in disbelief.

Fortunately, Lila was completely uninterested in his psychological history, as ever. She pulled the condom off herself and the dildo and, her breasts jiggling a little (it definitely was silicone because no way a forty year-old could be that firm), she left for the bathroom. Sam heard the faucet and stretched his legs under the sheet. He tugged it up to his chest.

Lila returned and quirked her head at him. She was stark naked, big breasts and a flaccid dick; it didn't even phase him now.

"You staying?" she asked, wiping her face with a towel.

Like it was even a question. Sam couldn't imagine just leaving after sex. Did people do that? Then he thought of all the times that Dean had come home in the middle of the night and realized that, yeah, they must. Huh. But he wasn't Dean.

She took his silence for an answer. She'd removed all over her make-up and the strong lines of her face were more apparent. Her nails were long and painted bright red, though, as she flicked a hand at him. "Move over then. You're on my side of the bed."

"Oh." Sam edged and crab walked to the other side, taking one of the pillows with him. "Sorry."

She snuggled in under the covers, her back to him, the bed rocking a little as she made herself comfortable. Sam pulled the blanket up to his chest and looked around the strange room, their clothes cluttering the floor. She adjusted the blankets around her, then looked over her shoulder.

"You're going to need a ride to school in the morning, aren't you?" She seemed amused by the idea, and he got it: the faux-motherly, guy-dressed-as-girl, older-man-with-college kid irony of it all.

"Um." Sam frowned suddenly. Man. He'd kept an eye on the route they'd taken, of course, and could easily find his way back to the bar, but it occurred to him that he had no idea what neighborhood he was in or even how far it was back to Stanford. He winced, squinting an eye. He hadn't done his homework for class tomorrow either. What had he been thinking?

"Yeah." He cleared his throat. "That would be good."

She chuckled and turned off the light.

Sam lay there for a long time with his eyes wide open, staring at the ceiling. Hand resting on his chest. In bed with a woman... okay, guy... well, sort of both... listening to the sound and feel another person in the room, unable to process everything that had happened.

Lila sighed heavily.

"Could you freak out a little more quietly?" she said. "I've got to get some sleep."

"I'm not freaking out," Sam said.

"The hell you aren't, college boy."

~*~*~

He found he couldn't sleep at all.

Eventually, he slid out from under the covers and stepped into his jeans in the dark, buttoning the fly, not bothering to find his underwear. The steps creaked underfoot, but downstairs Sam felt comfortable turning on the hall light. He sat down in the kitchen, a square of light spilling through the door, and looked around at all the signs of a lonely single life that he'd noticed before, getting the implications now. The skeevy bar far from home. The people at her job at the railroad who had to know. Lila passed for a woman if you weren't looking for it (or were a stupid college kid) but she wasn't perfect.

Sam felt her presence before looking up. Lila had put on an old-fashioned ruffled dressing gown, like something you'd see in a 1950s movie, and leaned against the door jamb. She held her collar closed.

"You okay?" she asked.

"You must have really wanted this," Sam said, unlacing his hands, his face earnest.

"'This'?" she said.

Sam made an up and down gesture to her body and then swept out to indicate her house, her life, everything, letting his hand fall. His meaning was apparently clear.

"That's the dumbest thing I've ever heard." She snorted. "Of course I did." She made a cupping motion as she shifted away from the wall. "Now. Come back to bed before I'm responsible for you flunking out of school."

As he followed her up the stairs, Sam couldn't help saying, only a shade irritated, "You know, that really isn't likely. I'm in the Honors program. Pre-Law."

"And you didn't even use it to get me into bed? Why, Sam, I'm proud of you."

~*~*~

In the daylight, Lila's truck was fire engine red, and somehow Sam wasn't a bit surprised. She loaned him a clean button down shirt – it fit – and then told him to keep it with an off-handed gesture.

He wanted her to drive right up to the front of the dorm in front of everyone, sort of giving them the finger for expecting him to be just like them. For disappointing him, when he'd wanted to belong. There was a part of Sam that wanted kiss Lila in front of the entire university. But Lila said, "No, thanks, I'm not a fan of train wrecks" and dropped him off on the circular drive outside the campus. She smiled a little when he leaned in through the driver's side window and insisted on a goodbye kiss. She gave him a gentle peck on the lips, fingers trailing down his cheek. "You take of yourself, okay, Sam?"

Years later, he respected her decision.

But at the time, it was a long walk through the lawns of a college that seemed even more alien than ever, a jacket slung over his shoulder, in a shirt that smelled like someone else. His legs were rubber and he felt, to borrow a phrase from Dean, fucked six ways from Sunday, and then only loosely strung back together. He trudged down the pavement not bothering with the sidewalk. A car passed him. He looked around at Stanford's palm trees, the clean southwest style archways and terracotta roofs, and tried to square that with the dust of midwest roads and cleaning an arsenal spread across his father's hotel bed.

He'd always been one of those kids who could talk to adults on their own terms, give his older brother a look that put him in his place, and clearly see from an early age that his father was a flawed human being. He was smart in other words. He'd always had it together, aced his classes even when he was dragged through three school systems in one year.

Sam stopped outside the dorm and stood there.

He couldn't go back to Lila's, he knew that instinctively, but he could just pack up his stuff and leave. He could go anywhere. He didn't have to do this.

Sam squared his shoulders and took a deep breath. He ducked his head, mouth pressed in a firm line, and forced himself to take the next few steps leading up into the dorm.

On the other hand... if he speed-read through his textbook, he might just make it to his afternoon class.

~*~*~*~*~

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