Purgatory Palace wasn't for anyone who didn't know what they were getting themselves into. The first thing that hit him when he walked in was the cacophonous music and the piquant smell of cologne lingering in the air from performers in meager blouses. Some of them were male, which earned Ruby an apprehensive look from Sam. She swore up and down that she hadn't taken him to a gay bar but he couldn't be too sure when he was sitting on the other end of the establishment under more decent lighting. The chairs on either side of him were unoccupied. Most likely because most twenty-somethings his age were either in a bordered-off section getting private lap dances, dancing with their one-night partners or mingling around the bar, debating on which pick-me-up to have on their night out.

Ruby left Sam to "scope out the selection" around the time that they walked in. A girlfriend of hers, Meg, was keen on stealing her from her best friend. Sam couldn't be entirely sure but between Meg's smoky eye shadow, six-inch stilettos, and the fact that she wasn't being hounded by men with her looks was sending him very strong vibes as to her intentions with a single brunette like Ruby. He didn't blame her, though. Ruby, as a strictly friend point of view, was very pretty. She had those daring brown eyes and a sharp rectangular face like a young Olivia Wilde or Keira Knightly.

But he couldn't help but feel like more of an outsider as he sat alone at the bar. Sam didn't have any distinctive features that set him apart from the majority of the people in the room. Dean was always more of the clubbing type because he was self-reliant and had the charisma—and, more than often, the comicality—of a five-year-old. Dean could easily go home with three different girls if he wanted. Girls dug guys for confidence, not substance.

"Excuse me, sir, you're going to have to order something if you want to sit here," came the bartender's voice.

Sam's back was to the woman. He barely registered it over the collective applause. "Uh—oh, yeah, sorry, I'm leaving now anyway—"

"Wait, do I know you?" the girl said, tilting her head inquisitively to the side. "It's Sam, right?"

Sam turned around to lock eyes with none other than Jessica Moore. She looked as beautiful as always, only this time her blonde hair was pinned behind her head and she wore a strapless black imitation tux corset with black skinny jeans. Usually, Sam didn't care much for the breasty-er outfits but she definitely pulled it off. And a little too well, arbitrating by the salivate crusting at the corners of his lip.

"Oh hey, Jess—Jessica," he stammered. Had he almost called her by nickname that he had fictionalized in his head? Smooth one, Winchester.

Jessica smiled nonetheless, out of amusement or plain cordiality. He'd like to think it was the second one. "What brings you here?"

"Well, I—you know, just hanging around." He propped his arm up on the island for that whole confident look, but probably failed when his hand slipped underneath him and his face almost met the hardwood counter.

Jessica gave him a quizzical look. "I can see that," she said. "It's just that not a lot of people come here to hang around."

"I guess I'm the exception," Sam said, taking a shot at being casual. "So you, uh—you work here?"

"Yeah, it's a part-time job until I can pay back my enrollment."

"I get that. I'm probably five hundred dollars in debt with the bookstore. I have a tendency to…hold books longer than I should."

"Oh, I see, so you're a book worm and a thief." The bartender's eyes crinkled in interest.

Sam laughed. "Hey, it's only classified as stealing when you don't give them back. I'm just… borrowing for an extensive period of time." Jess giggled at that—actually giggled. She had the most beautiful laugh he'd ever heard. Whatever incantation he had conjured out of his freshman Latin class to make that happen, he would be sure to use it again. "What are you into?"

She told him about her fascination for animation. Cartoons were a huge part of her childhood and drawing them was her passion. She wants to be a tattoo artist but claimed that there wasn't any livelihood in it. Her dream job is to get a contract with Disney ("Pixar, not the channel," she clarified), drawing cartoons for kids movies and hopefully learning the ropes behind animatronics. Sam smiled keenly at the perspicacity she spoke with, and at the day when she had worn a Smurfs t-shirt with the collar cropped out. Not that he was looking at her breasts in the first place… the jersey was very colorful, and certainly didn't draw attention to the respectable amount of cleavage that she bared...

"That sounds really cool, Jess." Damn it did it again, moron.

Small dimples revealed at the corners of her smile. "What are you into?"

"Law," Sam replied lamely. He felt just as dumb saying it. "The profession runs in the family… and by runs in the family, I mean my dad practically forced law down my throat. It's probably not as exciting as some of the other guys you talk to around here."

"Au contraire, most of the guys who walk in here are fraternity brothers with a couple beers to their name. Besides," she leaned in closer to Sam, resting her breasts on the counter in front of him, "I think it's kind of sexy."

Sam scoffed, albeit nervously. He'd never been this close to any girl, let alone the girl of his dreams. He swallowed something in the back of his throat when he noted that she wasn't scooting back any time soon. "W-what, studying?" he said.

"No—overpriced suits, using fancy words, putting criminals behind bars…" She trailed off, envisioning the thought while biting on her lower lip. She stared back at Sam with those gleaming brown eyes that bore into his soul a little while longer before the sound of a raspy-throated man's words stirred them both from their musings.

"I'll have a Guinness on the rocks."

Jess cocked her head in the direction of the rather familiar tone. Her lips turned type of way that could only be classified as a pity smile. Luckily for Sam, she lifted her bosom from his line of view when she said, "Another rough one, Cas?"

The man, Castiel, answered with a curt grimace. Sam would have been envious of the new guy occupying her services, but this wasn't the stereotypical Stanford douchebag that called him faggot because he was holding his then-estranged brother in an embrace for more than five seconds. The guy next to him was too debonair to be that type. With his slicked back hair and two-piece suit, he almost looked like he could be the next 007. He was relatively handsome too, with primitive features. If he wasn't creasing his lower lip with his teeth and shifting his blue eyes so often, Sam would have been easily fooled into thinking that he was confident beyond his exterior. (Having a policeman for a father set the bar high for his deductive reasoning skills.)

Castiel spoke up after he chugged down his drink a few times. If he hadn't stopped, Sam wouldn't have been surprised if he downed the entire bottle in a single sitting. "That's an understatement." He had an unnecessary growl in his tone. This guy was definitely aggravated about something. "You—do you have a partner?"

The young boy's face burned bright scarlet. "Me? No, no—I'm not with anybody."

"Good," Castiel said before lifting his bottle again, "all men are clueless piece of shits."

Sam nearly choked on what he presumed was his throat. Jess was giggling in the background, pretending to be preoccupied with shining an already-sparkling glass. "I'm not, uh—"

"Don't take it personally," Jess said, after containing more bubbling laughter. "Cas has been trying to get with this guy all week—" Castiel held up two fingers with his right arm while he buried his head in his left. "Two weeks. I don't know what it is. Maybe the guy's got a stick up his ass or he's not digging the whole corporate look but either way, but poor Cas here has been resorting to the bar faster than the dude has time to hook up with another girl."

Sam shrugged. "Maybe he's not gay."

Castiel gave him the death-stare. "Trust me, Thor. I haven't seen a guy rise that fast since Stanford was having its first annual Sausage Festival."

Sam scoffed at Castiel's subtlety. "Alright, where is this Prince Charming?"

"Watch and learn," Castiel said languidly, swinging his body to face said man. There was a massive throng of people but in the direction that Castiel was in, Sam could barely make out Mr. Passion Fruit. He had wispy brown hair and emerald green eyes that kind of reminded him of—oh my God. "See that?" Cas probed through gritted teeth, "he's giving me that leering look. He always does that when I pass by him. That woman is a cover-up, I know it."

Dean, his heterosexual brother Dean, was at the same club as him and making heart eyes at a dude. And damn, he wasn't just looking, he was writing a freaking novel. He would have finished if the girl next to him hadn't been harassing him to dance again. Dean shook his head and shifted his attention to her, rocking his body to the rhythm of her hips.

Castiel was practically snarling. Jess already had her back turned, pouring another drink.

Before Sam knew what he was getting himself into—before even comprehending that this was his brother in question and why the hell would he care so much about who he shacked up with when he didn't even have a girlfriend?—he was hurdling guidance at Castiel.

"Who the hell are you to give me advice?" he said bluntly.

That certainly wasn't an arrow to the knee. It wasn't like Sam had feelings of his own, or anything. It wasn't like he coveted the warmth of someone, and it most certainly wasn't like this guy, Cas, wasn't in the same exact position as Sam was making the same exact mistakes. Either this guy had sipped his drink a little too fast or he was naturally this demeaning. Sam didn't have to be a nice person. He could walk out right now, leave the both of them hanging with their mouths wide open and Ruby to lip-locking with some chick with a thousand oral herpes.

But Sam Winchester was too nice. At least that's what his brother said. The same brother that was currently rejecting a seemingly decent man—if you're the type that digs the film where 007 stalks the man of his dreams and gets hammered in the process—for a woman who he didn't even have simple courtesy for.

That's the kind of courtesy that'll win her over. "First of all, lose the coat. You look like you're more suitable to crunch numbers than you are another dude's junk. Secondly, loosen up on the hair grease. I feel like I'm looking at Danny Zuko's corporate twin. Oh, and unbutton your shirt. Dean likes cleavage."

Castiel was gaping at him like he had just seen a ghost. But he was more focused on the last sentence where he had peculiarly said… "Dean?"

Crap. "Or, uh—whatever his name is. Look, are you gonna take my advice or not?"

Castiel was doing all of the things that Sam had told him to do. He set his jacket on the counter, ran his hands through his hair a few times, causing it to fray up at the top, and unfastened his shirt until the younger man gave him the okay. Sam retracted his head, giving him a good once over. He looked more like Magic Mike and less like Michael Clayton.

Jesus, if Dean had overheard him using a Channing Tatum reference, he would have never heard the end of it.

Cas glanced back behind him, the same disenchantment surging through him like turpentine. "He's still with that woman."

"Be aggressive, Cas," he said firmly. "If you want him, you have to act like it."

He waved Cas off into the mingling crowd, watching him as he went. Sam realized then that maybe Dean wasn't better off with a woman. If Castiel was only into Dean for a one night stand, he sure was one determined son of a bitch. Dean needed someone like that. Someone to show him that there's more to what meets the eye—even if that's what caught his brother's attention in the first place.

From a distance he sees Cas approach Dean, tapping him from behind. One thing led to another—and by that Sam meant that the minute Cas had Dean's attention, he locked his mouth with Dean's in a force that would make Skywalker jealous—and Dean kissed him back before they decided to further consummate their love in the bathroom.

Sam chuckled lightly and turned around to Jess leaning against the back counter, one hand holding a pre-made drink and the other on her hip. She had an impish grin on her face.

"I think I could go for that drink now," he said, as if he had just been through a beating.

"This was for you, anyway, on the house," she said, laughing, handing him the drink. Sam raised his glass and downed a large sip.

"That was really nice of you, you know."

The law student set down his drink. "What?"

"Don't give me that sanctimonious retort, Sam Winchester," she reprimanded. "I know you just hooked up a completely random stranger with your brother."

Sam shook his head indifferently. "He's not completely random, he seemed nice en—wait, how did you—?"

"I once was a victim to the charms of a douche athlete. My ex, Casey Winters, was the guy that called you gay for hugging your brother. I broke up with him the same day and went to apologize to Dean." She paused to laugh again. "He said it was cool was long as he got a lap dance."

He rolled his eyes. "That's my brother."

"But he also said that he didn't really care," she said. "He told me that looking after you was his job since you guys were little and that he didn't mind grade-school name calling as long as you were safe. He even stayed the extra half hour before your class started just to make sure that you were."

Sam set his drink down to crane his head to where Dean was on the dance floor, albeit he was currently in the restroom getting hickeys from a tax accountant. He smiled. His brother really did love him underneath that I'm-one-hundred-percent-man-flesh persona. That's my brother, he thought again, this time more fondly.

"Hey Jess," he said, shifting his eyes back to the beautiful girl, "do you want to dance?"

The artist smiled, slight rouge threatening her collected features. "Granted that I still have an hour before my shift ends, I would love to."

So Sam sat in the same stool for twice the amount of time that Dean had spent waiting on him a few months before. He'd never focused so steadfastly on an analog clock in his entire life. By the time that ten came rolling around and he finally got to hold the girl of his dreams snugly in his arms, Ruby was out on the floor with a new boy and Dean was leaving hand-in-hand with his. Unconsciously, and a fair distance apart, they were both smirking in the couple's direction uttering, "That's my boy."