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Dean was drunk. Like, absolutely and truly hammered. And not the kind of drunk that he got from whisky and/or beer. No, Dean was drunk on cute little drinks that were pink and came with an umbrella.
Cas was newly human and the Winchesters were slowly introducing him to new things. Cas didn’t like beer, or whisky (which Dean hated) so Dean decided to take him to a bar and see if they could find Cas’ drink. Dean guessed that Cas would like something sweeter, and boy was he right.
Cas somehow maintained an insane tolerance for alcohol even after the fall. He was basically drinking Dean under the table. Dean didn’t mind. The more tipsy Cas got, the more he turned into a flirty, sassy, bitch, and Dean was in love with it. Dean, himself was turning into someone he didn’t recognize, either. The more he drank, the more his southern drawl came out. He started acting catty, and putting his hands all over Cas. They were both letting out a part of themselves that they never get to, and they were loving it.
After they got a cab back to the area around the bunker (even though Dean protested that he was fine to drive) they stumbled their way back. They thought about hanging out in the war room, but then Dean didn’t think that there was a good way to play music in there, so they decided to go to his room.
They walked into Dean’s room, shut the door, and then Dean turned on the radio. The first thing that played was Shake It Off by Taylor Swift. Cas waited for Dean to turn it off, but to his great surprise, Dean started bobbing his head to it. Dean got more and more into it, singing the song if he knew the lyrics, dancing horrendously constantly.
And Cas was giggling. He hid his mouth behind his hand, and giggled like a schoolgirl. Because watching Dean Winchester, macho man, shaking his booty to Bad Romance by Lady Gaga was a sight to behold. All of the sudden, that man had no shame.
Cas rarely laughed, and so Dean was over the moon that he could get this reaction out of the former angel. At this point, he would do anything to get that man to laugh.
Dean was dancing like his life depended on it, when suddenly he remembered something. There was this box that Charlie had given him, along with some other things that he had collected (shut up) would be perfect right now.
He told Cas to wait a minute, and went into his closet. Cas could hear him rummaging around in there, but he waited all the same. The radio station just kept playing these hits from years ago, and Cas had to ask himself what the hell kind of radio station this was.
Then Cas heard this dumb dialogue with a beat in the background. It sounded like some stupid thing that a kid would listen to. It was the worst song Cas had ever heard, and he’d only heard five seconds of it.
Then, right as the horrible high voice sang “I’m a Barbie-” Dean burst out of the closet wearing a pink feathered boa, no shirt, tiny black booty shorts that say “bitch” on the ass, a garter belt with thigh-high stockings, and fucking green crocs.
Cas snorted. He laughed hysterically, all while Dean did continuously embarrassing things. He danced around the room singing both parts (Cas would have to ask him later how he knew the words), he made a lame attempt at twerking, and started grinding on Cas.
Dean started walking forward in this horrible excuse for a catwalk, and started singing the last verse.
Dean’s deep voice had gone high, as he sang “You can touch / You can play / If you say,” at this point, Dean was right in front of Cas, a hair’s breadth away. Dean whispered, “I’m always yours.”
Dean crashed his lips into Cas, and Cas immediately grabbed onto Dean’s shoulders, drawing him in. Cas pushed Dean down on the bed, and laid on top of him. They made out sloppily, until they passed out, wrapped in each other's arms.