For Gallein! Sassy Exchange 2012 on Tumblr. Oh God I hope you like this. I hope I didn't mutilate the prompts too badly. I hope it's not too silly. Oh man.

Wordcount~3800, Rated T for language and heavily implied sex

If this were a romantic comedy, which this in no way resembles, really, it would be called The Wooing of Sam Winchester (but it's not a romcom, therefore this is not called that; actually, just for future reference the characters would like to disavow themselves from anything to do with romantic comedies).

Stage One: in which Castiel is annoyed, and then annoys Dean, and then realizes he just might be romantically interested in Sam Winchester.

Looking back, Castiel could pinpoint the exact moment the ball started rolling. That was because his memory was excellent; he was, after all, a higher being. What he was not so great with were metaphors. Sam had explained the rolling ball one to him, though. In this case, the "ball" was his attraction to said human.

Castiel would acknowledge that sometimes metaphors were useful. Just not out loud, because if Dean found out he would never hear the end of it.

(Or maybe he would. Sam would probably tell his brother to cut out any teasing that would result from such an admission, and Dean would probably-kind of listen. A little. Maybe. But Sam would try, at least, because he was a nice person like that.)

Going back to the moment with the "ball" and the beginning of its "rolling," here's what had happened:

They were in Texas, and he was annoyed. Very annoyed. Not for any one specific reason, but because of a buildup of frustrations and irritations, which all together were too much for him to just ignore. So he was being a bit sharp with his companions, and they noticed.

"Jesus, Cas, what's wrong with you?" Dean had exclaimed. "You've been pouting and glaring into space the whole day."

It took a great deal of effort to stop himself from punching the human. Castiel felt it would be justified, but he had to have self-restraint, and discipline, and—

"Seriously, dude, you look like you're constipated or something."

Luckily for Dean, Sam chose that moment to intervene.

"Dean, come on."

Dean spread his hands with an expression that said What? What did I do? Sam rolled his eyes and lightly shoved his brother towards the door.

"You're being insufferable, man. Why don't you go find a bar or something? I'll finish up on research."

Dean made a face. "Insufferable, seriously? You're such a geek." He snatched up his keys and left, but he was smiling. Castiel got the feeling he'd been waiting for Sam to release him into the wild.

Sam closed the door after his brother. "Sorry," he said to Castiel. "He gets a bit…he gets like that if he'd cooped up for too long. Tries to rile people up as entertainment."

Castiel, who had felt an immediate lessening of tension when Dean left (he was, after all, one of the major sources of annoyance in his life), finally relaxed back into the couch, closing his eyes. "Thank you, Sam."

"No problem," he heard Sam say. "Maybe now I'll actually get some work done." The tapping sounds of the laptop's keys resumed. Castiel opened his eyes and watched him work for a moment. Sam was intent on the screen, leaning forward and biting his lip in concentration. After a few minutes he seemed to sense he was being watched, and looked up. He frowned, and Castiel sorted through his mental collection of Winchester expressions and matched it up: this was Sam's "concerned frown."

"I'm fine," he said, preempting Sam's imminent question. Sam just looked at him, shook his head (the "exasperated head shake"), and stood up. The next thing Castiel knew, the other man was sitting on the couch next to him.

"You're obviously not fine," Sam said. "You're one of the most level-headed guys I know, and you were about ready to slam your fist into Dean's face just then."

"Perhaps your brother just has that effect on people," Castiel commented wryly. Sam grinned at him; the angel felt a vague sense of satisfaction at being able to make him smile. "Truly it's nothing, Sam. It's just…'been a long week.'"

Sam nodded. "Tell me about it."

For a moment Castiel thought Sam was using another colloquial expression, but then he realized he meant it literally.

"I couldn't—"

Sam crossed his arms and gave him one of the variations of his "stubborn" expression. Castiel resigned himself to an awkward conversation.

…which actually turned out to be not so awkward, much to his surprise. He was halfway through explaining what had happened with the two cats and the pigeon while he had been attempting to walk home after he somehow got lost trying to take the bus downtown, and admittedly he was being more animated than usual. Sam was leaning forward and biting his lip, the same "intent" expression he'd seen an hour earlier.

"That sucks," he said after Castiel explained the next part, with the bicyclist outside the Chinese restaurant. "No wonder you're stressed." His words were sincere, and somehow that made Castiel feel a bit better. He halfway smiled, which seemed to surprise Sam but nevertheless he beamed back at him. For some reason, Castiel had to look away.

"I'm sorry to complain to you," he started, but Sam immediately waved it off.

"Hey, I asked you to. And I wanted to listen. D'you feel any better?"

"Yes, actually. Thank you. Again."

"Anytime, Cas. I mean, really, any time you ever wanna talk—"

"Ugh, is that what you girls've been doing while I was gone? Talking?" Suddenly Dean was there; Castiel hadn't heard him come in. Sam shared a look with the angel, then got up and returned to his computer.

"You're back early. Did you accidentally hit on a guy again?"

"Shut up, Sam," Dean said with a scowl, but didn't explain. Interesting.

Castiel got up and trailed Dean into the kitchen, for no other reason than to unnerve him, which he had found was fairly easy to do if he just stared at him long enough and stood a bit too close. He thought Dean might be on to the fact that he was doing it on purpose, because Dean just kind of glared at him like he'd expected it.

"Why don't you go back to bothering Sam?" Dean asked, pulling a beer out of the fridge.

"Sam is busy. He's researching."

"Wasn't stopping you when I walked in," Dean pointed out.

Castiel shrugged. "He volunteered to listen. It was very nice of him."

Dean just rolled his eyes at the implied unlike some people I could mention. "Yeah, he does that."

"Does what?" Castiel inched closer, trying to make Dean as uncomfortable as possible. Yes, this was almost as satisfying as punching him.

"Listens. He didn't always do that, you know. When he was younger it was all talking, all questions, all the time. Didn't really listen to anyone much. Changed after he went to Stanford. I think it's because of Jess."

"How do you mean?"

Dean kind of glared at him. "What's with the interrogation? I dunno, I just think having a long-term relationship like that made him a good listener. I'm sure his girlfriend would've had bad days and he'd listen and then they'd…I dunno, have really great sex or something."

Castiel was stunned. "You're saying that his listening to me was…boyfriend behavior?"

"Well yeah, I mean—no, no wait, I don't mean—shit. I don't mean he wants to be your boyfriend or anything. He just, he does that with everyone, okay? He fucking listens, wants to talk about feelings, whatever. It's just something he picked up from Jess and now it's a habit."

"Oh." Castiel had to tell himself that Dean's clarification was not disappointing at all. Then he had to tell himself there was no reason to tell himself such a thing because he wasn't disappointed. At all. In any way, shape, or form. No.

"Right. Something he does with everyone. And not because he wants to be their boyfriend."

"Right," Castiel agreed.

Dean took a long gulp of his beer. "Why me?" he asked no one in particular. This seemed a bit overdramatic, in Castiel's opinion. He decided to devote the rest of his night to bothering Dean.

And not thinking about Sam.

So maybe "pinpoint" and "exact" weren't really accurate. "The moment" was more like a blur of Sam smiling at him and Dean saying the word 'boyfriend.'

Still. He knew he hadn't thought about Sam in a romantic sense until after that night. And he hadn't really, really thought about it—it was just kind of a vague idea in the back of his mind—until this happened:

Pennsylvania this time. The motel room was cramped. He was making dinner.

Sam leaned over his shoulder, peering into the pot on the stove. Castiel could feel one hand on his back and soft hair against his cheek.

"Looks good," Sam said, and Castiel started blushing.

Which was new.

"Cas, are you—your face is all red; are you okay?" Sam turned him around, leaned down and stared at him. "Cas?" His proximity was only making the blush worse. Because for some reason it was just now hitting him that he wanted Sam to want to be his boyfriend. And Sam was standing too close, and it was making him, of all things, blush.

"Dean!" Sam called out. "I think something's wrong with Cas!"

Dean hurried into the tiny kitchen. "What?"


They were both staring at him now.

"Well that's weird. What is it Cas? Are you sick or somethin'?"

He was still too close. Castiel found himself unable to speak.

Sam put his hand on his forehead. Castiel tried to pull back, because this was just embarrassing.

"Dude, you're making it worse, whatever it is," Dean said, swatting Sam's hands away.

"What?" But it was true; Castiel's blush was intensifying. Sam looked bewildered. "I—I guess I'll go outside then?" And he hurried out of the kitchen.

Dean waited for Sam to close the door behind him. Then he gave Castiel a look that Castiel couldn't recall from his mental catalogue, but recognized immediately. It was a dude-I-cannot-believe-you-have-a-crush-on-my-brother-what-the-hell look.

"Don't say anything," Castiel warned, but Dean just scoffed.

"You know, you're not intimidating at all right now. So seriously, what the fuck? When did this happen?"

"Just now, apparently," Castiel muttered sullenly. Thankfully he could feel his face starting to return to normal.

Dean gave him another look. Castiel was expecting some kind of lecture or rebuke, but suddenly Dean was smiling. It was the quite possibly the worst moment of Castiel's life, to see that smile.

"Dude. This is hilarious."

"I'm glad I'm such a source of amusement for you," Castiel growled, and shoved Dean away. The man stumbled back a few steps, but the grin remained.

Once again, the urge to punch him in the face was rising. The second-best option was to escape the kitchen. Or the apartment. Or the mortal plane altogether.

He settled for escaping the apartment, only to remember once he was out the door that Sam was outside, too.

Sam had been sitting on the curb, but he immediately got to his feet when Castiel walked out.

"Hey! Are you alright?"

Castiel merely nodded, finding himself speechless again.

Sam bit his lip and shifted nervously. "Was it—was it really something I was doing?"

Castiel opened his mouth to reassure him, but still couldn't make himself say anything.

Sam shrank back. "Okay. Um. I guess…I mean, that's alright, I can just. Just. Keep my distance—"

"No!" Castiel finally regained the ability to speak, only to realize he hadn't quite recovered the finer points because his voice came out too loud and a bit too high-pitched. "You don't have to do that. Or anything like that." He paused and cleared his throat. "It was just that the kitchen was too crowded and…" He couldn't come up with a decent excuse.

"Well, okay. As long as it's not that you hate me or something like that." Sam tried to sound like he was joking, but it was a bit too subdued.

"Of course not." He steeled himself for the next part, knowing Sam needed the reassurance. "I like you very much, Sam."

Sam smiled at him. It was quite possibly the best moment of his life, to see that smile.

Oh no, Castiel thought. I'm doomed.

Stage Two: in which Castiel makes a plan, then attempts to execute that plan, and is continually embarrassed through the entire process.

The plan was to find out what Sam liked, and use that to…well. Castiel didn't really know what word to use. Mostly because they all sounded cripplingly trite and embarrassing. His choices were: 'romance,' 'court,' and 'woo.' He eventually settled on 'woo,' for no other reason than that it was the shortest and he felt that somehow made it the least humiliating.

But yes, the plan was to woo Sam Winchester, because just being around him and trying very hard not to be in love with him proved to be impossible, no matter how much he attempted it.

The wooing was to be achieved by finding out what he liked and using those things to get closer to him. His first attempt to gain some insight into Sam was to ask Dean—which was useless and mortifying and why had he done that? It had been horrible. His next attempt had been to just ask Sam, but he'd chickened out. So instead he ended up covertly following Sam around, in a completely un-stalkerish manner. Occasionally Sam would catch him at it, but wouldn't say anything. In fact, he seemed kind of amused, and he'd let Castiel join him in whatever he was doing without questioning why he'd been following him in the first place.

Sam was very nice. Castiel caught himself just thinking about how nice Sam was sometimes, and then he'd smack himself on the forehead for being so ridiculous. Admittedly this had garnered him several odd looks from each of the Winchesters. But that wasn't important. He was on a mission.

First he tried giving him food. Both Winchesters liked food, although their taste in everything except beer varied. Sam had a penchant for healthier food which wasn't particularly hard to pick up on.

They were in a fast food restaurant, the one with the redheaded pigtailed child, and Sam ordered a salad. After they sat down with their food, Castiel shoved a packet of ranch dressing across the table to Sam. He knew from his observations that ranch is Sam's favorite. Both Winchesters stared at him for a moment. It was incredibly awkward.

"Thanks, Cas," Sam said eventually. He smiled, which broke the awkward tension. Dean went back to ignoring them in favor of scarfing down his burger. Sam drizzled the ranch over his salad, then glanced up at Castiel. "Want a bite?" he asked, holding the fork out in invitation.

Castiel hastily shook his head. Sam shrugged.

So that didn't work out so well.

His next ploy was to try touching Sam.

Sam seemed like a very tactile person, which was unfortunate because Dean didn't seem to be. Sam was all about patting his companions on the back, or clasping a shoulder, and other small touches. Castiel figured it wouldn't be hard to reciprocate somehow; naturally, he was completely wrong.

Mimicking those touches was hard. Mostly because he was embarrassed and wasn't used to touching people. At all. And that made the whole think even more awkward.

Once again, though, Sam found a way to make it feel normal. Castiel was fairly certain Sam was trying to help him out on purpose, probably thinking he was attempting to fit in more. Whatever Sam's reasoning, it made the touching thing much easier.

Sam would smile and put his hand over Castiel's whenever he awkwardly tried patting his shoulder, extending the brief contact. Eventually Castiel grew bolder. He felt his crowning achievement was when he sidled up behind the couch and pushed his fingers through Sam's hair, something he'd been thinking about doing for a while. Sam had made a surprised noise, then a pleased one, and had allowed Castiel to continue the motion for several minutes. He'd stopped when Dean came in, retreating to his own side of the room. But Sam had smiled at him.

It had been great.

What was not so great was the lecture he got from Dean, which included the phrases "better be serious," "if you dare hurt him," and most horrifyingly, "do you need condoms?"

At least that meant Dean thought he was actually getting somewhere. Castiel felt like he hadn't made much progress at all, as far as wooing went.

Another time they were staying in an inn on the Outer Banks. Castiel had followed Sam down to the waterfront. No one else was around, surprisingly. It may have been because the day was a bit chilly due to the breeze. In any case, the only other occupant of the tiny strip of sand was a large white bird on long legs, wading in the shallow pools of water left behind when the tide went out.

"Is that an egret or a heron?" Sam asked. "I can never remember the difference."

Castiel just shrugged. Words were beyond him at the moment, because Sam's face was flushed pink from the wind, and he was smiling, and had Castiel mentioned Sam's eyes yet? Because they were quite beautiful.

"I really should know," Sam continued. "When I was in high school I helped the Science Olympiad team out a lot, and they had an ornithology event…"

So Sam liked birds. That was nice.

Hm. For some reason, the fact that Sam like birds stuck with him. But Castiel's thoughts were moving slowly, like molasses, which was a simile and not a metaphor.

Sam liked birds. Well, Castiel finally managed a coherent thought, angels are kind of like birds, right? (He knew several angels who would smite him for thinking such a thing, but that wasn't important right now.)

Sam liked birds. Birds had wings. Castiel had wings.

"Sam," he said.

By the time Sam turned around from watching the heron/egret, Castiel had allowed his wings to manifest.

Sam's eyes went wide. "Cas—oh, wow."

Which was certainly a gratifying response. Castiel had to fight the urge to preen. He was not actually a bird. In fact, he was much more interesting than a bird, so take that you stupid heron.

Sam inched forward, almost shyly, staring in fascination. Castiel lifted his right wing and used it to herd Sam closer to him. Since touching was okay now, he allowed himself to maintain the contact, so the wing covered most of Sam's side, including his hip, where Castiel longed to put his hand. With just a bit of shifting, he had Sam standing inside a kind of protective circle, surrounded by his wings and close to his body.

"Wow," Sam said again. His voice was soft. Castiel was almost positive they were finally about to have a romantic moment of some sort, but then they both heard the barking of a dog, getting closer rapidly. Sam gave him a rueful smile as his wings disappeared from sight again.

Later, Castiel told himself he was not jealous of the dog as he watched Sam rub at its ears and chat amiably with the owner, who had been walking the mutt on the beach.

And much later, he finally got his romantic moment.

Kind of.

They were finishing up a hunt, and Sam had (of course) been slammed into a wall by the monster. As a result, Castiel had his arms full of woozy Sam. He was attempting to hold him up, which he definitely had the strength to do, but not the height. Sam was basically draped over him, which meant Castiel had to keep one arm wrapped firmly around his waist and the other…lower. He wondered if this counted as taking advantage.

Sam pulled away momentarily, despite Castiel's protests that he really shouldn't be moving around. "Wh're's D'n?" he slurred.

"Upstairs, getting the last of the—"

Sam cut him off. "Good." And he leaned down and kissed him.

Castiel stood completely still, shocked. Then Sam passed out.

Now what? Castiel wondered. Fuck.

When Sam regained consciousness in the back of the Impala, he looked immediately to Castiel. "That happened, right?"

Castiel nodded, unsure what to say.

"Okay. Good."

"Good," Castiel repeated.

"Great," Sam said, smiling.

"Oh my God, shut up," Dean said from the driver's seat.

A week later, Dean was not there to tell them to shut up when Castiel found himself naked and seated in between Sam's legs on the bed in their motel room. He wasn't quite sure how he'd got there, but it seemed like an excellent place to be.

"Wow," Sam breathed after Castiel kissed him again.

Castiel was having an instinct. He leaned down and used his tongue to—

This time, the noise that came out of Sam's mouth was not a recognizable phrase in any language, unless there was a language that Castiel was unaware of which consisted entirely of moaning.

Later Sam finally found his words again. "I was not expecting that," he said, looking dazedly up at the ceiling.

Next to him, Castiel said, "Did you know the shortest war on record was between Zanzibar and England, and it lasted for thirty-eight minutes?"

Sam blinked at him. "Wasn't expecting that, either."

Castiel shrugged. He'd thought it was interesting.

Sam stared at him a moment longer. "More sex," he decided. "We can do weird history facts pillow talk later."

"Okay," Castiel agreed.

Stage Three: in which Castiel has a boyfriend, he annoys Dean some more, and it's pretty great.

"I think I'm getting the hang of doing this backwards," Sam said. He finished tying Castiel's tie, and smoothed it down carefully. "There, you can barely tell you were having sex just a few minutes ago."

Dean made a gagging noise from the living room. "Jesus Christ, you guys know I can hear you, right?"

"Yeah? How long've you been listening?" Sam called back.

"Kill me now," Dean groaned.

This was really nice, Castiel concluded. Dean was in the next room and he didn't even have to stare at him to make him uncomfortable any more. Sam's hands were still on him, and he was smiling. Mission success.

"Love you," Sam murmured, leaning down to kiss him.

"I love you, too, Sam."

"Would you guys quit with the lovey-dovey crap and get a move on already?" Dean shouted.

And he didn't even mind that Dean was being annoying, because he had Sam, and Cas had fallen head-over-heels for him, and that was a metaphor, and this is the end.