Chapter Text
Dean Winchester awoke in the back seat of his 67' Impala with a crick in his neck and random brunette whose name he didn't remember. He yawned and stretched as best he could in the tight quarters, thinking to himself that this had been a hell of a weekend. Two nights in a row with two different girls - it had been a while since he'd gotten that lucky. He adjusted his jeans, which were still hanging half off his hips and zipped up before nudging the sleeping woman next to him. It was already ten-thirty, and hotel checkout was at eleven. If he wasn't there to pick Sammy up soon, he'd get an earful the whole way back to Lebanon.
"Hey sweetheart," he purred in his silkiest possible sex-voice. "I don't mean to rush you out, but I have to get on the road."
"Oh. Yeah. What time is it?"
"Just after ten-thirty."
"Shit, I've got to be to work soon," she grumbled, sitting up and fixing the skirt that was twisted up around her waist. "Have you seen my panties? Wait, here they are." She huffed as she struggled to put them on, trying not to kick Dean in the cramped backseat.
"Here," Dean interrupted. "Let me."
"What?"
He shot her his best smirk and gently shoved her back against the car door, then grabbed her ankles and straightened her legs as she giggled.
"I'm gonna miss these beautiful legs," he murmured, sliding his hands up her calves for a moment before picking up the satiny red panties and slipping them over one ankle. He picked up her other foot and threaded it through the panties and began sliding them up, but as he got to her knees, he paused. Placing her legs over his shoulder, he knelt and hiked her skirt up once more, then slid the panties up onto her hips. With a sly grin, he spread her legs and leaned forward, pressing a gentle kiss to the red satin as she squirmed with arousal.
"Fuck, you're smooth," she panted as he winked and fixed her skirt again. She cleared her throat quietly as she took a minute to compose herself. "Well this was fun. If you're ever passing through town again..." she said, reaching into her purse to jot down her number, "give me a call." She shoved the scrap of paper into the pocket of his flannel shirt and gave him a quick peck on the cheek before opening her car door and strutting away.
Dean sighed blissfully he leaned back against the seat. Yes. It had been a good fucking weekend. He took a second to straighten his clothes and then got back in the front seat, slammed the car into gear, and hurried back to the motel.
Sam was standing out front, slumped against a soda machine when he pulled up, and he wasn't looking pleased. He scowled and shook his head as he picked their duffel bags up off the ground.
"'Bout damn time," he grumbled. "Don't worry, I cleaned the guns and got everything packed up myself." He walked around to the trunk and threw the bags in, then climbed into the passenger's seat.
"Aw shit. Sorry," Dean grimaced. "I forgot we said we were going to do that. You could have waited for me though." He turned the Impala onto the main road in search of the nearest diner.
Sam sighed and shrugged his shoulders. "Nah, it's alright. What else was I gonna do alone all weekend?"
"Well thanks."
Sam nodded, relaxing now that he had got that off his chest. "Suppose I shouldn't go raining on your parade. Two nights in a row, huh? Bastard," he grinned.
"I love this town," Dean smirked. "That happens once in a lifetime, Sammy."
"Yeah, yeah. So I assume it was that Rachel girl from the bar last night? She was hot."
"Rachel! Right! She was hot. And she was a total freak," Dean hummed happily.
Sam rolled his eyes. "And I'm guessing... that dark-haired guy from the night before? Derek, was it?"
"What? No! The hot waitress from the restaurant." Dean felt a warm flush creeping over his face. Sam knew he hooked up with guys from time to time, but it still made him uncomfortable talking about it. He had no idea how Sam knew - It wasn't like they'd ever had a heart-to-heart converstation or anything, Sam just seemed to know, and thankfully, he never questioned it.
"The cute redhead? God, I hate you," Sam laughed. "Oh hey, Cas stopped by last night. He was looking for you."
"Oh? Did he say what he wanted?"
"Nope. Just that he wanted to talk to you. Speaking of Cas and hooking up, when are you two going to do it?" Sam winked.
"Dude! What the fuck? " Dean yelled. "Me and Cas?" It wasn't the first time Sam had pestered him about it, but it was really starting to get under his skin.
Sam grinned. "Why not? He's clearly into you. You can't tell me you haven't noticed! The way he follows you around, the way he's always touching you. And Jesus, the way he looks at you! "
Dean shifted uncomfortably in his seat. "That's ridiculous! He's not into me. That's just... his way. He's socially awkward. It's probably an angel thing."
"He doesn't act like that around me."
"Yeah, well, he's closer to me than you. Trust me, he's not into me."
Sam closed his eyes and leaned back against his headrest. "Whatever you say, Dean. Hey, wake me when it's time for breakfast."
"Sure." Dean frowned and focused on the road ahead. Well that had killed his good mood. What the hell was Sammy talking about? He was always joking about it because they were so close, but he couldn't possibly think Cas was into him. Jesus, they were friends! Dean had never had many close friends, but he was pretty sure their relationship was just friendly. He wasn't even sure Cas was into... well, anything, really. He'd apparently had sex with April, but aside from that, he'd never even mentioned hooking up with anyone. Though he'd gotten better over the years, he was still pretty naive in terms of human sexuality and emotions, and Dean couldn't even begin to imagine Cas in a relationship.
He drummed anxiously on the steering wheel as he drove, silently seething at Sam for bringing this up again. If he was being completely honest, it wasn't like he'd never thought about it. Cas was a pretty attractive guy, in a dorky tax-accountant sort of way. Most of the time, any dirty thoughts occurred in his dreams, but on rare occasion, those deep blue eyes would haunt his memory when he was jerking off. Those were the nights he'd lie awake cursing himself for being an awful friend until he finally fell asleep, guilt gnawing at his stomach. It might be different if he thought Cas was interested, but it was a stupid, one-sided infatuation that he'd been pushing down for the last few years. He wasn't sure if he could ever be in a 'relationship' with Cas, but he was sure as hell attracted to him. Oh god, stop thinking, he berated himself. This is the kind of thing that destroys friendships.
He sighed as he realized he'd just passed the diner he'd been looking for, and he pulled into an empty driveway to turn around.
"Wake up, Sammy. We're here."