Things the Winchesters Learned the Hard Way

AN: You probably noticed already, but these first two are a more PG-13 than normal so be warned. But I inflicted girl-related humiliation on Dean in the last chapter, so it's only fair to do the same to Sammy.

Winchester Life Lesson Number Two: Don't let your big brother play matchmaker.

"What are you doing here?"

Sam barely glanced up from his laptop screen. He was sitting on his bed, in sweats, the TV on in the background. "What do you mean?" he asked tonelessly.

Evasion. Sam-code for I don't wanna talk about it.

"I mean, why are you here? Thought you were out, y'know, gettin' some?"

Sam snorted.

"Eh, don't be like that." Dean raised an eyebrow. "You know and I know what was on your mind when you left the bar. The prude act's got nobody fooled, Sammy."

Sam shrugged, face carefully blank.

"Dude, what happened?"

He was silent for a moment. Then, "Not my type."

"Not your type?" Dean asked incredulously, locking the motel door behind him and shrugging off his coat, throwing it on a chair. He'd just come back from a late-night fast food run, content to hang out here and maybe catch some pay-per-view while Sam finally, finally got himself laid. Truth be told, Dean had been rather proud of the hand he'd had in the whole thing: he'd blackmailed a Sam who'd been in a rather bad mood after a day of research into talking to the pretty Latino girl at the bar by threatening to introduce Sam to her himself if Sam refused to talk to her. He hadn't exactly thought that, given Sam's track record with women, that Sam would want to sleep with her at all, even if he was interested. But they'd be here for at least the rest of the week on this case, and hey, never say never, right?

He'd been pleasantly surprised when Sam left the bar with her, not even minding that Sam had taken the car and left him to walk because he was so simultaneously proud and amused by the whole thing. She'd needed a ride back to her place, as she'd hitched a ride with her sister and her sister's husband, and the bar was only a few blocks from the motel, so it hadn't been a big deal for Dean to walk back himself. It had been nine-ish when Sam had left with her, and ten when Dean had left the bar himself in search some semi-decent fast food and taken his time walking back to the room.

It was twelve now.

…So obviously something had gone wrong.

"Not your type?" Dean repeated, sitting down opposite Sam on his own bed. "What do you mean she wasn't your type? Man, you sat there with that Anita girl—"

"Allegra," Sam muttered.

"—Allegra, whatever. You sat at the bar for two hours with this Allegra chick talking about literature, for cryin' out loud. And I didn't even bother to eavesdrop because it made my freakin' head spin every time I tried. It was disgusting. Of course she was your type."

Sam's jaw clenched. He stared determinedly at the laptop. "Yeah, not so much."

Dean's eyes drifted to an open bottle of vodka sitting close to Sam on the bedside table. "You didn't chicken out, did you?" he asked, teasing.

That got Sam defensive. "No," he said dryly. "I was just going to drive her home. Some of us like to get to know a person a little before trying to get in their pants, you know."

"Oh," Dean said with a suggestive leer. "So how'd that go? How well do you know Allegra now?"

"Pervert."

Dean shrugged. "Your type or not, you were gone for a couple hours, dude. Everybody's got urges every once in awhile. So what happened?"

Sam frowned at him. "None of your business."

Dean rolled his eyes. "Oh, come on. You know I'm just gonna keep asking until you tell me."

"Dean," he repeated, annoyed. "Really. I don't want to talk about it."

Of course, Dean completely ignored that, and started guessing anyway, rapid-fire. "Bad breath?" he ventured. "B.O.? Three kids?" He thought for a second. "Tranee in disguise?"

Sam scowled but otherwise ignored him.

"Come on, man. No fair. You gotta give me something."

"No, I don't."

"Toe hair? Communicable disease?" No response. "A husband at home and a Brazilian pool boy on the side?" Still no response. Dean sighed dramatically, but kept firing off the guesses. "Lesbian. Russian assassin. Scientologist." A pause. "She isn't secretly that goblin we're supposed to be after, is she?"

Though he tried to hide it, Sam smiled a little at that one. "No."

"What, then?"

"Just forget it, okay?"

"But—"

"Please."

Dean frowned. Sam had actually sounded a little desperate. Okay, maybe he should back off…

"Yeah, okay."

Sam nodded once. "Thanks," he muttered.

"Sure." Dean gave it a moment before asking, "That bad, huh?"

"Uh…" He looked anywhere but Dean. "Yeah."

And that got Dean a little worried. Because really, if something bad had happened, like bad bad, it was kinda-sorta-totally his fault for making Sam go talk to the girl in the first place. "Did she…" He leaned forward a bit and scrubbed a hand over his face, wondering how to word this delicately. "Did she, uh, do anything to you?"

Sam looked up. "No."

"Okay…" Dean wasn't sure if he ought to just leave it at that, then. Sam didn't appear to be lying, and some things…well, some things a person certainly had the right to keep to themselves.

…Especially from an adult brother.

…But still.

"Uh…" he began, clearing his throat and trying to push past the incredible awkwardness of the situation. "Are you sure it's something you don't wanna talk about?"

Sam glowered at him. Yeah, right.

"Nah, really. I mean it. You get a free pass, and—" he picked up the vodka bottle and handed it over to Sam—"and after tonight, we'll never speak of it again."

Sam looked at him skeptically. "Really."

"Yeah."

A beat of silence.

"Promise?"

Dean held up his hands. "Scout's honor."

Sam stared at the vodka bottle in his hand for a long moment, as if scrutinizing the label. Then he huffed a sigh and set the laptop aside, pinching the bridge of his nose.

When he still didn't say anything, Dean asked, tentatively, "She didn't…hurt you or anything, right?" Because if she had, girl or not, Dean would be hard pressed to resist the urge to hunt the skank down and kick her ass.

"No." Sam fidgeted, picking at a hole in his sweatpants. He was still determinedly not looking at Dean. "I already told you, no."

"You sure?"

"Yeah…" Sam rubbed at the back of his neck. Dean noted that his face was going slightly pink.

"Yeah, but?" Dean pressed. "I sense a 'but' coming on."

"But," he muttered darkly, unscrewing the cap of the Vodka, "She would have hurt me if I'd given her half a chance." He took a long swig of the vodka. "I'm told that sort of thing has got to be consensual, though," he added, almost inaudibly. His face was now blotchy red, and he'd gone back to fiddling with the hole near his knee.

Dean blinked. "Oh."

Oh.

He cleared his throat. "So...one of those."

"Yep." Sam smiled thinly, obviously mortified. "One of those."

And honestly, Dean didn't know whether to burst out laughing—a dominatrix? And Sam?—or feel really, really guilty.

But the guilt thing wasn't so easy to manage when he was having a hard time keeping a straight face.

"'S not funny." Sam mumbled, glaring at him.

Dean shrugged. Maybe making light of the situation would help things. "Eh, it's a little funny."

Sam just kept glaring.

"Nah, but seriously, dude, I don't blame you for bolting. Tried that shit once. Some freaky girl from Fort Lauderdale. Or, uh, St. Augustine. Not sure, actually."

"Really?" Sam smiled, surprised and maybe a little relieved.

"Really," Dean admitted. Well, there went my dignity for the evening… "You were in California at the time, and… Yeah, not really my thing."

"Yeah, me either." Sam shook his head, looking nauseated. "Not sure I get how it could be anyone's thing."

Dean shrugged. "Got me." He thought for a second. "Except maybe the outfits." He sighed appreciatively. "Leather bikini and chains, man. Wasn't a bad look for Miss Fort Lauderdale. Well, uh, 'till she started doing the freaky stuff." He made a face. "Not sure I understood the point of that riding crop."

Sam laughed. "Riding crop?"

"Yeah, yeah, laugh it up," Dean grumbled. Geesh, the lengths he went to to be sympathetic towards this kid…

Sam chuckled and handed Dean the vodka. "Sorry."

"No, you're not."

"You're right. I'm not." A pause, and then an embarrassed grin. "Allegra had a dog collar."

Dean gaped. "What? Aw, gross. Really?"

Sam winced. "Yeah. It's…out sitting on the dashboard right now."

"You put it in the car?" Dean asked, appalled. "You actually put that shit in the car? You contaminated my baby."

"Sorry. I was kind of in a hurry."

"Alright, well, first thing in the morning we're burning the damn thing." He shook his head. "A friggin' dog collar? Really?"

Sam reached for the bottle. "Really."

Dean shuddered. "Why?"

Sam took another long drink before answering. "Dunno. But she called me...Uh, she called me 'puppy.'" He looked sufficiently wierded out.

"What?"

"Yeah."

He met Dean's eyes. A second passed, and then they both burst out laughing.

"Puppy?" Dean gasped out, nearly doubled over from cracking up so hard. "You're kidding, right?"

"No." Sam's previous tension seemed to drain away, and he was unable to keep a smile off his face now.

"Wow," Dean chuckled. "That's ten kinds of freaking disturbing."

"I know, right?" Sam flopped back on his pillows and stared at the ceiling. "Man, we have got to finish this hunt so we can get the hell outta this town."

"Agreed." Dean stood back up, intent on grabbing a shower before bed. He looked down at Sam. "Seriously, though. Puppy?"

"Apparently."

"Lame. You shoulda asked her for something more awesome, like…I dunno, 'Lone Wolf'."

Sam cringed. "Okay, suddenly I'm not so comfortable discussing this with you anymore."

Dean smirked. "If it'd been me, I'd have been 'Raging Tiger.'"

He had to duck as a half-empty vodka bottle was chucked in the general direction of his head.

*End*

Next time, Winchester Life Lesson Number Three: While they might be a good way to get girls, Broadway shows are to be avoided at all costs.