I posted this on Tumblr already, so I thought I'd post it here, too. :) Review?

Usual disclaimers, I don't own Supernatural, or any of its characters.

The story of how Dean Winchester became best friends with Castiel Novak was… Well, interesting to say the least. Dean wasn't really even aware of Castiel's existence, outside of the fact that he was the youngest of the Novaks, and there were a lot of them, so that was pretty much common knowledge.

Dean knew as much as everyone else about the Novaks. There were five of them, big family, pretty tight. They had a big ass house, but he supposed, with five kids you'd have to, right? They'd moved to town about six months ago, at the start of the school year. Their father was some big business man, so they were kinda loaded. There was Michael, who apparently was at college, Balthazar, who was travelling the world, Gabriel, who was a senior, and then there was Anna and Castiel, both juniors.

Dean honest wouldn't have given a crap about any of that, except he was curious. Why? Because damn Anna looked good. Cheerleader, long legs, red hair, Dean was pretty sure they were made for each other, the first time he saw her. Dean didn't get around half as much as everyone seemed to think, and he was completely capable of holding a relationship for more than a week. Sure, he flirted a lot, but that didn't mean he slept with everyone he flirted with. According to the rest of the student body, it did, Dean just… Didn't deny it. Any publicity was good publicity, right?

It took him all of two days to convince Anna to give him her number, and two weeks to get her to go out with him (he was going to do this one right, because the last thing he needed was four angry brothers after him)

Three weeks into dating Anna (to the amazement of everyone he knew, including his little brother, Sam) she invited him over to his place after school. At first he was he was all for it, but then she'd told him that one of her brothers would be home. He didn't even ask which one before replying, "I don't know Anna…"

Anna sighed and fixed him with that look that all the girls he'd dated seemed to have, the Dean-why-are-you-so-frustrating look. "Dean, my brother won't be a problem, okay? He'll probably just be in his room." She gave him another look, the please-I-really-want-you-to-do-this look. "Please? Besides, you can't avoid them all forever. You'll have to meet my brothers sometime."

He laughed, but it was without humor, since his brain was busy filling he was imagining what would happen to him if Anna's brothers ever found out what they do in the back of the Impala. He cleared his throat, and hoped he didn't look too pale. "Ah, yeah, alright," he finally agreed. "I'll let Sam know, and meet you at my car after school, okay?" Because really, how bad could it be? Anna was promising alone time, and who was Dean to turn it down?

"Great," she replied, giving him a quick kiss before heading to her class in a flurry of red hair, leaving Dean standing, stunned in the hall. Why? Why did he have to meet her brothers something? Dean was pretty sure he could go his whole life without wanting to meet them. The only thing was… He really liked Anna, to his own surprise. It wasn't just that she was hot anymore, it was that she was hot and funny and fun, and God he was so screwed.

That was how Dean found himself being let into the aforementioned big ass house. It was nice, and not as snobby and obviously rich as he'd thought it would be. There were family photos, mostly of the five kids pulling faces, or standing in weird poses. The Novaks were just like him and Sam, Dean decided, except with more money and more of them. Maybe Anna's brothers wouldn't be so bad, Dean thought as he followed her through to the kitchen, which was very in scale to the rest of the house, meaning it was massive. Anna gave him a quick tour of the house, kitchen, living room, her brother's rooms, her bedroom, and it was when they got to the bathroom that things started to get interesting.

Interesting as in just as they were walking away from it, because Anna's brother was in there, taking a shower, he walked out. Anna obviously hadn't told him they'd be having company, because he only had a towel wrapped low around his hips. It took him a few seconds to notice that Dean was standing there, and when he did, he looked between Dean and Anna for a few seconds, before turning around and walking into one of the bedrooms without a word.

"Well," Anna said, turning to him, taking in the confused look on his face. "You just met my little brother." That was Anna's nerdy little brother? When Anna had told Dean about her brothers, he'd pictured him a lot different. Anna had told Dean that Castiel was a total genius, so of course he'd pictured him with glasses, scrawny… Typical nerd.

But with eyes and a body like that, there was no way he was a typical nerd.

And wow that sounded gay.

Dean didn't even try to redeem himself from that. There was no way he could make that sound less gay.

"That's…" He paused, trying to remember the order of the Novaks. "Castiel?" Anna nodded, and Dean felt a wave of relief wash over him. It would have been a little awkward if he'd said the wrong name. After three weeks with a girl, he knew he was supposed to know, at least who were brothers were, but there were so many of them, and they had such weird names, he tried to remember them, but he couldn't help it.

Dean was still a little dazed as Anna led him to her bedroom, but he soon pulled himself together and pushed all his confusion aside, enough to do what he did best.