A hand smacked the fold-out table that was Dean's "booth", his head jerking up from his phone at the sharp noise amid the hubbub of the crowd.

"Hey, there, artsy," a short, blonde man said, grinning crookedly, hand still flat on the plastic surface, "My brother wants to get his face painted, and we were hoping you could help with that."

Dean raised his eyebrows but plastered on his professional, customer-service, dealing-with-rude-people smile. If the man couldn't be bothered to read the stupidly bright and colorful sign declaring Face Painting, $10, there was a large chance Dean would need to work hard to keep his cool. "Well, you've come to the right place." He stuck his phone in his pocket before waving vaguely at the assortment of paint-splattered brushes standing proudly out of a red plastic cup. Not incredibly professional, but he did work at a fall carnival, after all. It's not like he could afford a nice studio set-up as a high schooler with a part-time gig. Plus, his usual clientele consisted of four-to-seven year olds, and as long as Dean knew how to paint Spider-Man, they couldn't care less. "Long as you've got ten bucks, I'll paint whatever he wants."

"Oh, it doesn't matter what he wants." The man grinned wider. "Ooh Cassie!" He turned and sang over his shoulder, "Come here!"

"Cassie" parted from the throng and walked over, radiating embarrassment. He looked about Dean's age, which was a welcome surprise after painting children all night. No offense to the little guys, but the squirming and nose wrinkling made it hard to paint straight. He was cute, too, Dean mused to himself. Dark, messy hair and blue eyes. The trench coat was a little weird, sure, but certainly not the worst choice to protect against the October temps. "Gabe, do we really have to do this right now?"

"Yes." Gabe's face was serious, but Dean trusted that about as far as he could throw the guy. He could still see the corner of his mouth twitching and the wicked amusement in his eyes. "You agreed to this, bucko."

"Yes, but I thought it would take you longer to find someone." Cassie muttered, rubbing his forearm nervously. His eyes were locked onto his brother's, obviously trying to puppy-dog-eyes his way out of the situation.

Damn. Guy could give Sam a run for his money. Dean chuckled quietly to himself.

Unfortunately for Cassie, it seemed Gabe was immune to the look. He turned back to Dean, smirk firmly back in place. "Columbo here- "

"Rude." Cassie muttered quietly.

"-has agreed to sit still while you paint whatever your little heart desires all over his pretty face. And then walk around with it all night, no matter what it is."

Dean blinked and slowly raised his eyebrows. "And just why would he agree to do that?" He glanced over at the teen, who still looked incredibly like he wanted to disappear.

"Not your problem, sweet cheeks." The blonde finally lifted his hand to reveal a crumpled ten on the cheap table. "We got ten bucks, you paint. Weren't those the rules?" He gasped dramatically, covering his mouth with his hand, "Unless you changed them?"

"No," Dean plastered on his fake smile again, suppressing the urge to punch the guy. "Those are still the rules."

"Well, ain't that just swell." Gabe turned and raised his eyebrows at his brother, sweeping his hand dramatically to the wooden stool across from Dean. "You sit, Cassie. I'll be back in twenty minutes. That cotton candy looks to die for. Paint something good!" Gabe disappeared as quickly as he had come, melting seamlessly into the Friday-night crowd.

After a few moments, Cassie shuffled awkwardly around the table, lowering himself slowly onto the seat.

It was almost comical, how much taller that made him than Dean. The stool was higher up, for the kids, so it put the guy at least a full head above Dean. This one might hurt his neck a little, Dean noted.

"You know," Dean began conversationally, fiddling with his paints, carefully avoiding eye contact. He felt like, if anything, that might make the guy more embarrassed. "If you want, we could just tell him to shove it. I won't get fired or anything."

"No, I did agree to this." The teen muttered, but he still sounded like he was marching into his own grave. His eyes were focused intensely on the red and white striped canvas wall behind Dean's head.

"Yeah, it's frickin' ugly, isn't it?" Dean turned around to where Cassie was looking, trying to lighten the mood. "I tried to ask for a black one or something, but the owner of this place is really weirdly attached to the whole 'carnival' look."

Cassie cracked a small smile, shoulders loosening a bit. His feet rested on the bottom rung of the stool, legs clearly longer than the seat was made for.

"So what's your real name?" Dean asked, turning back. "I have a feeling it ain't actually 'Cassie'."

"No, it isn't, Gabe just likes to call me that because he knows it bothers me. My name is Castiel." It looked like the small talk was helping him relax, so Dean kept going.

"Hate to agree with that guy," Dean screwed up his face in distaste, leisurely picking up a brush. He was hoping if he started slowly, he wouldn't spook the guy. "But it is kind of the older brother's right to call the younger one nicknames. God knows I bug Sammy enough with it." He dipped the brush into blue paint, almost absentmindedly.

"Yes, well," Castiel shrugged. "That doesn't mean I have to enjoy it."

Dean chuckled. "No, it doesn't." He lifted his hand, bringing it up to Castiel's face carefully, but not yet touching his skin. He smiled at the widened eyes, slight panic obvious in them. "The paint might be a little cold, but don't worry. This doesn't hurt at all." He said soothingly, drawing from past experiences with freaked-out toddlers.

"I'm not worried it will hurt." Castiel screwed his eyes shut, eyebrows furrowed and nose crinkled. Dean sighed internally. So much for that, then. "I'm worried about what you're going to paint." He cracked his eyes open when he didn't feel anything on his face.

Dean laughed, lowering his hand again. "Don't worry, dude. You seem like a really nice guy, so far, anyway, and I'm not the type to paint dicks on anyone's face. Even if they're a dick."

The slight blush and averted eyes told Dean that had been exactly what the other boy had been expecting.

"No way, man!" Dean crowed. He felt slightly offended, but couldn't help but sit back and laugh. "You thought I was going to draw dicks on your face!"

A woman walking by his table cast an offended glare at him and hurried her little boy along. Dean snorted at the kid's delighted grin, still giggling to himself.

"Well!" Castiel began defensively, "You're a high school boy! They draw dicks on everything!" He pointed at Dean, "Plus, if Gabe got to choose the design, he definitely would have told you to paint them on me."

Dean pursed his lips sympathetically, but couldn't help the small chuckles still escaping. "Yeah, I met him for thirty seconds and I could see that. Don't worry," He held up his free hand, the other still resting on his knee with a dripping paintbrush. "I promise I will not paint dicks on your face. Scout's honor."

Castiel squinted at him suspiciously, but nodded acceptance. "Okay, fine. You may continue." His shoes squeaked on the cheap wooden rung. "I trust that you won't paint inappropriate things on my face." His face smoothed out as he relaxed again.

"Oh, are all inappropriate things banned?" Dean grinned, quickly reaching up and swiping a few calculated lines on Castiel's face. "I just promised no dicks, we didn't talk about other stuff."

Castiel squinted at Dean again, lips pressed tightly together, obviously trying to figure out whether he was kidding. The crowd noise seemed louder in the silence, overlapping voices creating a rumbling background to the impromptu staring contest. "… you wouldn't." A game booth a few tents down started ringing some kind of bell.

Dean snickered at the look, secretly thinking that it was adorable. It was like a puppy growling at you. Especially with the random streaks of blue across his forehead. "No, I wouldn't. I'm joking, Castiel. I am not going to paint inappropriate things on your face."

"Good." Castiel muttered, his face slowly returning to a calm expression. His hands tangled together in his lap, he still visibly looked a little unsure about the situation.

Dean calmly reached up and started adding lines, dipping back into his paints every few strokes. "So why are you doing this?" He asked gently, dabbing color onto a temple. "Don't get me wrong, face paint is a way better route than a tattoo or something, but no offense, you don't really look like you want to be here." He leaned in and stuck his tongue out of the corner of his mouth as he grabbed his thinnest brush, beginning to slowly add web-thin lines.

"No," Castiel protested softly, "I don't mind it here. I like the energy. It's almost like sitting in the middle of a thunderstorm." His smile crinkled the wet paint next to his eyes.

Dean felt the odd sensation of simultaneous disappointment at the smears and appreciation of the cute smile. He smiled and shook his head at himself, reaching up to fix the area.

"I just don't like to participate. It's very suffocating, the crowds are…" He shrugged self-consciously. "Gabe says I plan too much. I'm not 'impulsive enough'." He did the little air quotes, the dork. "This was supposed to show that he was wrong."

Dean raised an eyebrow, adding more white to his paper plate "palette", mixing a lighter shade of blue. "I don't know, man, it kind of just sounds like an opportunity for him to mess with you." He would know, he'd pulled schemes like this on Sam enough.

Castiel sighed before scrunching his nose at the touch of the brush on the bridge of it. "Yeah, I figured that out about five seconds after I agreed to it. Like you said, though, face paint is better than a tattoo."

The game booth bell rang out again. "… he wouldn't." No way.

"Oh, I assure you, he would."

Dean shook his head in disbelief. "Crazy, dude. Your brother is crazy."

"You don't know the half of it." Castiel muttered darkly.

"Probably not," Dean agreed. He used his free hand to gently push some curls off of Castiel's forehead, smoothly adding a few more lines.

Castiel's eyes slipped closed, apparently now used to the feeling of the brush. "He once replaced every document on my laptop with a copy of the Bee Movie script."

Dean winced in sympathy. "Ah, damn. He didn't erase anything super important, did he?"

"No," he sighed, "I had back-up copies of everything incredibly important." His mouth twisted into what Dean could only describe as a pout, and a cute one. "It did put me a few days behind on a final paper, though."

"Yeah, I bet." Dean said, dipping into some gray. "I haven't done anything like that to Sam, just the little stuff. Itching powder in his underwear, spoon in his mouth while he's sleeping," he shrugged, even though he knew Cas couldn't see it. "Nothing that would really hurt him or ruin anything critical."

Castiel scrunched up his nose again, and Dean sighed at the new smudges. "That's certainly better than my brother, but it still doesn't sound too pleasant for Sam."

"He always gets me back, don't worry about him too much." Dean carefully corrected the blotches and continued. "Don't wrinkle your nose like that." He admonished softly. "It messes up the paint."

"Oh, sorry, I didn't think about it." Castiel seemed embarrassed by that.

"Not a big deal," Dean tried to soothe, lightly brushing a few more curls out of his way. "You're doing way better than my usual, promise. Have you ever tried to paint the Batman symbol on the cheek of a five-year-old who just finished his third cotton candy?" He shuddered loudly.

"No," the corner of Cas' mouth twitched up faintly. "Can't say that I have."

"It's not for the faint of heart." Dean muttered darkly.

Castiel chuckled under his breath before they both fell silent again.

A girl walked by arm-in-arm with her girlfriend, both laughing loudly at something. A boy a few stalls down whooped as he won a stuffed crocodile. The crowd continued to buzz, friends yelling at each other across the path as parents scolded children for wandering off.

It was oddly peaceful, sitting here, painting Castiel's face. It was nice, Dean thought as he switched brushes again. A comfortable silence.

"What are you painting?" Castiel asked quietly, eyes closed.

Dean grinned lightly at the hesitancy in the other boy's voice. "Cas, I am painting a giant Hello Kitty design." He said, keeping his voice low and calm. "Aaaallll over your face. You have a pretty little pink bow here." He tapped the handle of the brush against Cas' temple, "A nice little yellow nose here," tapped against the tip of Cas' nose, "And whiskers." He traced the handle over Cas' cheeks teasingly.

"Dean," Cas' voice was amused, if anything. His eyes stayed shut, seemingly unconcerned. "You haven't painted my nose or cheeks, and you were using like five different shades of blue."

Dean chuckled under his breath. "Yeah, okay, Columbo, you're right." He sat back for a moment to take in the whole design critically. "You know that Willy Wonka movie with that blueberry chick?"

Cas' eyes flew open and he shifted suddenly, about to stand. "You did not- "

Dean quickly reached out and tugged him back down, laughing. "No, no, Cas, of course I didn't."

"You better not have." He muttered as he sat again. "I have to walk around with this all night, you know."

Dean nodded, pretending solemnity, dotting a few more places. "I know, Gabe told me."

"Assbutt." Castiel muttered.

The bell rang out from the game booth again. Dean carefully sat down his brush and raised his eyebrows. "Assbutt?"

Castiel looked over at the churro truck down the way, avoiding Dean's eye line. "Yes." His cheeks looked suspiciously pink. "And are you calling me Cas now?"

Dean suppressed a smile and shook his head. Dork. "Yes." He reached out and turned Cas' face back to him, doing a final sweep of the design. "Lookin' good." It really did look good; at least Dean thought so. It had helped that no one else had wanted their face painted. He hadn't had to rush to get to another customer.

"Are you done?" Cas didn't seem to mind the hand that was still resting against his cheek, but Dean put it down anyway. No need to freak out the guy.

Dean hummed an affirmative before grabbing his hand mirror and holding it against his chest. "You ready to see it?"

Castiel looked unsure, but nodded anyway.

Dean felt a warm glow fill him at the guy's trust, and couldn't help the grin that spread across his face. The game booth bell started ringing again, this time flashing lights, too. Someone had just won big. Dean raised the mirror to Castiel's height. "Ta-da!"

Castiel looked awestruck. A few moments passed, silence from both teens as someone at a game booth yelled something about a palm tree. "… how did you do this?" He whispered, reverently trailing his fingers across the lines.

Dean suddenly felt bashful and dropped his arm, shrugging awkwardly. "I just painted it, dude." He rubbed the back of his neck, unsure. "So you like it?"

Castiel gently pried the mirror from Dean's hand and held it up to his face, turning left and right to see the entire piece. "Oh my gosh. It's amazing! I love this!" He beamed at Dean, who couldn't help but smile back in the face of that gummy smile.

Castiel continued to examine himself in the mirror, admiring the beautifully complicated network of blue lighting emanating from his right temple, arcing across his face to the other side. Dean had layered different shades of blues and whites, making each branch look incredibly 3D and lifelike, and even added some stormy clouds across his hairline. He couldn't stop smiling at it; the artwork was so stunning.

Dean leaned back against his chair, quietly satisfied that Castiel liked the final product. "Soo…" He drawled, "I guess this means you'll take risks more often, huh?"

Castiel lowered the mirror and beamed at him again, replying, "If it ends anything like this, I will become the most reckless person in Lawrence."

Dean rolled his eyes and took back his mirror, putting it back on the table. "Slow down there, Evil Kenevil, you can work your way up. Nothing dangerous, you got me? I kind of like your weird, dorky ass."

Cas rolled his eyes, but he was still smiling. "I feel like I should be insulted, but I think that was a compliment, so thanks."

"Yeah, no problem." Dean rubbed the back of his neck again. "So, look, uh…"

Castiel waited patiently, fingers absently reaching up to brush against the paint again. It probably itched, Dean thought.

He blew out a hard breath before deciding to just get it over with. "I know we didn't talk all that much, but you seem like a really cool guy." And you're unbelievably adorable, Dean added silently. "I haven't taken my break yet and, if you're not in too much of a rush to get back to your brother, I'd like to see if we can't hang out some more. Maybe." He glanced up. "Like get dinner or something."

Castiel tilted his head to the side, reminding Dean of when they got Bones as a puppy. He couldn't help chuckling again at the cute motion. "Would it be a dinner-date or just a dinner?"

"Well," Dean tapped his fingers against the table, staring at a yellow splotch on his ring finger. "That's up to you, I guess." He glanced up, "I wouldn't mind it being a date, but if you're not comfortable with that, we can just get food as friends. No pressure." It would be a little disappointing, sure, but he definitely wouldn't mind being friends with Castiel.

Castiel ran his hand through his hair, a few curls falling onto his forehead. "I would like for it to be a date, as well." He smiled shyly.

Dean stood up, brushing his jeans off. "Awesome." He smiled and stepped forward, gently brushing the curls back off Cas' head. "Careful with that for a minute," he warned quietly, "paint might not be totally dry yet."

Castiel hummed acknowledgement, and Dean could see the slight blush at their closeness, without a brush in between them. They both smiled softly at the other.

"C'mon." Dean took a step towards the main thoroughfare, sticking his hand back to Cas and wiggling his fingers in invitation. "We won't find gourmet steaks, but Garth's deep-fried turkey legs are pretty great, if that's okay with you?"

"Sounds good to me." Cas sent Dean a quick smile as he took the painter's hand.

"Will Gabe be worried if we aren't here when he finally comes back?" Dean asked, beginning to find his way through the throng. He accidentally bumped into a woman, both parties muttering a quick apology.

"Probably." Cas stepped closer, grip tightening on Dean's hand. Dean smiled privately at the action. "But he always is telling me to be more impulsive, so, if anything, he'll be proud."

"He wouldn't leave here without you, would he?"

Castiel was silent for a few paces, "You have a car, right?"

Dean threw back his head and laughed, squeezing Cas' hand and stopping in front of Garth's truck. He had a feeling he was going to have a very good night.