Feathery_Fool
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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?
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After his father dies unexpectedly, Dean moves back to the only town that ever truly felt like home. It’s time to settle, put down some roots, and take over Bobby’s auto shop. At the local Gas’n’Sip, Dean runs into one of the reasons his feelings for Sioux Falls have always been so fond.
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Dean Winchester, owner of Winchester Fine Auto Restoration, is in town for one night, the last night of his trip as he checks in on each branch of his chain of shops.
Cas is Roman Enterprises CFO, and has been in meetings for days over a merger that should have taken a single 8 hour conference call.
A surreptitious invitation at the hotel bar could help both men unwind.
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Dean's a busy dad, he doesn't have time for dating. That may be changing, thanks to one very hot librarian. Can Dean overcome his insecurities long enough to make a connection?
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After a fallout with his situationship, Dean Winchester finds himself literally out on the streets. When he ends up in the home of his best friend to finish recovering from surgery, Dean struggles to keep his romantic feelings a secret.
Castiel would do anything for Dean, so when he plucks him off the street, it’s not a question that he’ll help Dean recover. He’s just got to work around the fact that he’s madly in love with Dean, with no hope of his feelings being requited.