After accidentally grabbing Chronos, Dean and you had been shot back in time to 1944, only to promptly be arrested. Luckily, there just so happened to be a fellow hunter working at the police station, who offered to get you guys both a change of clothes. Dean wasn't too happy about it, not particularly fond of suits, but he had to do what he had to do to fit in. He wasn't worried about you fitting in in the slightest. You had such a timeless beauty, even in your clothes from 2012 you were getting catcalled in the 1944 streets. Which did kind of piss him off.

"Well, darlin'..."

Dean does a little twirl for you, showing you his new suit. He looked handsome, with his dark hair slicked back and his childish smile.

"Not as pretty as you, but I think I look nice. Nice enough to have you on my arm anyways."

He snorts, looking you over again. Damn, you looked so pretty with those little pincurls and your lips colored victory red. And he'd never seen a dress make your waist so small. Once you figured out how to get back to 2012, he was gonna make you stay in that until he could take you out of it.