Sam/Dean, the boys having sex for the first time in years after Sam gets his soul back. (They haven't since Dean went to Hell in season three.) There's nerves and awkwardness all around on both sides at first, but sweetness abounds.
Dean's never really been the kind of guy who plans sex. It's usually kind of just something that happens--he meets a likely looking girl, or sometimes a guy, and if everyone seems amenable, there's sex
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