Fics like Death of a Bachelor

A series of tragic circumstances left Dean with a pile of hospital bills and his brother to take care of. To make ends meet, he needs to take a new personal assistant job, one that's going to fly him halfway across the country to work for one of the nation's hottest new authors: Castiel Novak. Castiel isn't what Dean was expecting at all, and he comes to realize why Castiel has a reputation for being a difficult boss to work for. Time away from Sam, and getting to know his boss, make Dean realize he needs to reevaluate his life and what he wants for himself. And that just might include the one person he cannot have.

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