Fics like Sweet Boy

Dean's sixteen when he meets John's well-to-do boss, Castiel Novak, and he's quick to develop a crush during a time where he's only begun to discover his preferences. He dates the beautiful Lisa and practically raises his younger brother Sam, because it's what John expects. But Castiel appears to see Dean in a way no one else does, and despite him knowing there's no way anything can happen between them, he relishes in the idea that Castiel cares at all for his well-being. Between mounting pressures from a teenage Sam that no longer wants a caretaker, John's nudging for Dean to follow a career path he doesn't want, and a mysterious check for the exact amount of one semester at the school Dean had been eyeing, Dean finds himself reconnecting with Castiel. And Castiel has a very interesting proposition for him.

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