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Summary
Dean likes to sleep around with anyone who'll spare him a glance. Gender, orientation and personality doesn't matter - he doesn't discriminate. The only problem is he's getting bored with how easy it is to coax his fellow students into bed. That's where the bet comes in.
Everyone thinks Sam is polite and well-spoken and an absolute Angel to everyone he meets. He isn't. In fact, he poured milk over Gabriel Milton's head last year when the older man tentatively asked him out, because eww. Sam doesn't do old, broke and friendless. He does, however, make bets with his brother.
If Dean can bed the University president's straight, wealthy son - Castiel - within a month, Sam has to date Gabriel until he graduates. If he can't bed Castiel, Sam gets the Impala; Dean's beloved car.
Who will win the bet?