1. When Sam is 5 and Dean is 9 he's got this big idea about Halloween. It's still new to him, it's still fun and staying up all night eating candy is still worth the throwing up and stomach ache in the morning. He still wants to dress up as a ghost or monster, he still thinks they are fun and exciting, he knows nothing of what is totally real about the scary supernatural world his family hangs out in.
And Dean's okay with that. Sam's young, he deserves to be a kid about something, really. But Dean draws the line at a few things and Sam's Halloween idea is one of them. Dean would be fine is Sam wanted to be a ghost, a vampire or some random cartoon character, he can deal with taking him house to house in the random neighbor they ended up in this Halloween. He'd even be fine throwing a sheet over himself and going door to door for the candy if Sam wanted him to.
But this, this isn't' something Dean's fine with.
"Please!" Sam whined in a high pitch little brother cry that he developed over the years, "I really want to Deany! It'll be fun! Please!" He bounces on his heels, as Dean sits on the smelly old motel room couch.
Dean rolls his eyes and crosses his arms. "No, Sam. I'm not doing it. Everyone will laugh at me."
Sam pouts his lips and mimics his brother's arm cross stance. "They wont laugh at you Dean! They will think what an amazing brother you are to me! Just this once, Daddy said I could dress up as whatever I wanted and this is what I wanted!"
Dean's last defense is another huff and eye roll knowing very well it's a lost chance when it comes to something Sam wants.
And later when they are out trick or treating, when they ring their first door bell and an older lady with a bowl full of candy answers the door, she has to fight back a laugh as Sam in a pair of bright blue overalls, stripped shirt and wig of red hair stand next to Dean in his bright red and white nylons and blue and red dress with his own matching red wig stand before her, bags open wide and waiting.
2. It was all for Sam, really. There's no way you can attend your first Home Coming dance alone. That's just sad and pathetic, so Dean decides if Sam couldn't get himself a date, then Dean would take matters into his own hands.
Even if that means Dean would have to wear a dress. A short, black, boarding on cocktail dress. Hair hiding underneath a long brown wig, eye shadow, lip gloss and some smelling stuff the lady at the beauty counter tells him would drive the boys wild. He struts in the dimly lit (and thank God for that) decorated gym and calls out Sam's name in his most sweet and innocently girly high pitch voice.
It's worth the look on Sam's face, totally worth it.
3. So, there was this ghost that haunts a lesbian bar, and one of them has to look the part. Sam's too tall to pull it off, truthfully. And the dress was cute, short red little number that swooshed and swished around Dean's knees. And that if he saw any other girl walk past him wearing, he'd be all over that. And he's got some lip gloss that makes his lips all sparky and smooth. Smells like strawberries at that.
He pulls it off rather well too, with Sam, his pre-op Transvestite friend. He flirts, he twirls in the dress, he even dances a little with a very cute girl with curly brown hair who laughs and touches his shoulder and winks at him. And then he loads the ghost full of rock salt and burns every last inch of it's evil lesbian obsessed bones.
All in all, he makes a pretty damn good woman in the end.
4. You'd do it too if a hot chick asked you. Dean isn't that kinky, really, but this one, this one's a piece of work. Legs that go on forever, he's gonna do anything to get a hold of that.
Even wearing her midnight blue party dress. And heels. Long, clear, plastic, cheap hooker looking heels that make him wobble too and fro when he tries to stand. He feels as tall as Sam almost. It's the heat of the moment when she asks and Dean's upstairs brain hasn't been in charge for a few hours and the downstairs one green lits anything that'll keep this kinda thing he's got going on to go on.
So, the dress it is. And she makes it worth his wild and manges to leave it for him as a reminder when she slips out in the morning.
5. This time it's all Dean, because truly every once in awhile you need to feel pretty.
(And Sam has the black mail pictures to prove it.)