A/N: Although I didn't intentionally write it as such, you could certainly read some Dean/Cas into this if you wanted to. Also, I originally wanted Dean to win the game (this was also going to be a wee!chesters fic initially), but then the idea of Cas... well, you'll see. Read on!

Sam isn't sure who started it – Dean is adamant that it's Sam's fault, and Sam blames Dean – but somebody, somewhere along the line, lost a bet, and that's the basics of how they got here. Sort of. Anxiety is building up in his stomach, something like nausea boiling and making its presence known, and suddenly Dean turns to him and snaps, "Jeez, Sammy, can't you tell your friggin' stomach to shut up?"

"'S not my fault," Sam mutters, but he's kind of craving a nice Caesar salad right now to calm his nerves. The crunch of the fresh lettuce, lightly dripped dressing, enough to add flavor but not enough to smother the yummy greens… mmm, yeah, that'd be real nice right about now. But no, he's not looking at a delicious, healthy meal at the moment. Instead, he's staring at the door to their motel room, which could be the door to Hell itself from the way the brothers glare at it, regarding it warily like it might try to eat them at any moment.

Finally, Dean throws his hands in the air in obvious frustration. "Why are we even waiting here for him anyway? It's not like he's going to come in through the front door anyway."

"Habit," Sam mumbles. In a louder voice, he adds, "Besides, he's your angel. You have to teach him to use the door sometime."

"For the last time. He is not my—" But Dean gets cut off there, because in a temporarily blinding flash of light, immediately after which Sam mentally moans, My poor retinas, Castiel appears. With a box in his hands.

Sam cranes his neck, trying to read the words on the box, or at least catch a glimpse of the picture, anything for some sort of clue – but it's pretty hard to do with his eyes feeling like they've been peeled like grapes by some sort of lightning knife. He can sort of see Dean doing the same next to him, but of course it's easier for him because Castiel is doing his usual hovering-by-Dean thing. Which gives Dean a completely unfair advantage in situations like these, Sam thinks; but then again, he'd rather not have a feathery holy being less than six inches away from him at all times, thanks.

"What is it?" Sam asks nervously, because he's not sure he can stand the tension anymore.

Of course Castiel says nothing until Dean says, roughly, "Cas?"

And just because it's Castiel, and Castiel is Dean Winchester's angel, he grants a response. "A board game."

Sam scrunches his features into b*tchface number 32, one of his personal favorites, and barely manages to not roll his eyes as he grumbles, "Well, obviously. That was the deal, right?"

"Actually," Dean interrupts quickly, "seeing as nobody can even remember the original challenge, maybe we shouldn't do this anyway. I mean, it's not like it counts if nobody remembers, right?"

"Or maybe," Castiel offers, "you should not make bets when you are so drunk, Dean."

Dean turns a sort of purplish color, which Sam finds rather interesting, and finally splutters, "Oh, whatever! Let's just do this, all right?"

"The game," Castiel announces with a flourish, "is called Pretty Pretty Princess."

Sam has his face in his hands, so he can't see Dean's gleeful expression as he smirks, "Oh, yeah, Princess Samantha over there will just love that."

"Whatever, Dean. Just remember that loser has to do laundry and dishes for a week, and it's my turn to pick our next hunt," Sam shoots back, already planning a nice and bloody zombie hunt or something equally sinister.

"Not like it matters, since I'll beat your butt into next Tuesday," Dean brags.

Sam raises one eyebrow. "Do you really want to win at Pretty Pretty Princess, Dean?" he asks.

"Oh, shut up," Dean growls. "Let's get started, Cas."

Castiel carefully goes about the process of setting up the game. It's in pretty good condition, Sam notes, and he's not sure he wants to know where the angel found it. The spinner's a little wobbly, and one of the stick-on gems on the crown is missing, but all the pieces are there.

"Okay, Cas. You gotta pick a color," Dean instructs.

Castiel looks up at him with those sickeningly adorable puppy-dog eyes. "Why would I choose a color?"

Dean sighs. "You spin the little spinner thingy to determine how many spaces to move your pawn, then the space you land on decides which piece of jewelry you get to pick up. The goal of the game is to get all of the jewelry of one color, then the winner gets the crown. Well, sort of. There's enough for every color except there's only one crown, so – you know what, forget it. You'll figure it out."

"It sounds as though you have played this game before," Castiel notes.

Sam starts laughing as Dean turns bright red. He says defensively. "Look, Alice was the only friend I had in fourth grade, okay?"

Castiel nods seriously. "I am glad that you had friends, Dean, even if they were girls."

Sam's so busy trying not to bust up laughing that he forgets to pick a color, so of course Dean dumps him with pink.

"Really, Dean?" he says grumpily, but he doesn't really care. Dean chooses green, "because it's the manliest color there is in this friggin' box," and when Castiel spends a whole minute debating between purple and blue, Dean decides for him. Blue, of course. Sam rolls his eyes for at least the fifteenth time in as many minutes. Because of course it has nothing to do with Jimmy Novak's brilliantly blue irises, right?

At first Dean insists that Castiel get the first turn, but Sam reasons that he should go last so he can observe how the game is played. Dean agrees and instantly seizes the spinner for himself. Part of Sam wants to argue, but contrary to Dean's opinion, he's not a child anymore. In fact, he's probably the most mature out of the bunch, in spite of the fact that Cas has centuries – heck, probably milennia – on him, on account of the angel is new to this whole human thing.

Cas seems to get the hang of the game rather quickly, and ten minutes later, it's a pretty near tie. Sam looks around at the three of them sitting cross-legged in a circle on the floor. They make a pretty hilarious sight, actually: Dean's wearing one earring, a necklace, and a ring; Castiel has managed to snag both blue earrings and a bracelet; while a bracelet dangles from Sam's wrist and a pink plastic ring adorns one finger. It's Castiel's turn, and when his pawn lands on the black ring, he reaches for it without hesitation.

"Aw, man, Cas,that sucks," Dean comments, laughing a little.

Castiel appears confused. "What do you mean? Isn't the object of this game to collect every piece of jewelry?"

"Yes, but if you still have the black ring at the end of the game, you lose," Sam explains, trying to hold back more laughter. This is great. He's playing Pretty Pretty Princess with his brother and an angel of the Lord, for crying out loud! That's pretty much the weirdest thing he's ever done, hands down. Even with all the supernatural crap he's seen, this has got to be the weirdest.

"Oh,"Castiel murmurs, and he looks so forlorn that Sam automatically goes to hug him before he remembers, Angel of the Lord. Right.

"Aw, don't worry, Cas," Dean encourages. "You'll get rid of it soon enough."

And he does. Sam half-expects Dean to take it from him when he lands on the "take any piece" space, but instead he reaches over and yanks off one of Sam's pink earrings. Sam glares at him, but he doesn't say anything, even though he's pretty sure the little girls this game was made for aren't quite so aggressive with trying to tear apart each other's earlobes.

At the end of the game, Sam is stuck with the black ring, even though he's got everything else from his set. He's about ready to chuck the stupid mirror at his brother when he sees that Dean isn't wearing the crown – it's Castiel. Castiel, who wasn't even a part of the original bet, has won.

Initially Dean opens his mouth to complain, but then he seems to have an idea. Dean gets an evil glint to his eyes. "You know, there's one last part to the rules, Cas," he says.

"No making up rules, Dean. Cas won fair and square. Just because you hate losing—" Sam begins.

"Hey, Sammy? Shut up, will you? I'm not tryin' to cheat here. I swear." He digs out the tattered instruction booklet from the bottom of the cardboard box. "There's one last thing you gotta do."

And there is no way, even if he were under orders from Heaven and Hell both, that Sam could keep from snickering as he watches the angel look into a plastic mirror and utter quite seriously, "I am a Pretty Pretty Princess."