well technically he's a butt virgin
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There are people hitting on Sam wherever he goes, and Dean is doing weird things like holding doors open for him and touching him way more than is necessary, and it's all driving Sam up the wall. It doesn't help that he's been in love with Dean for just about forever, and all of it feels like a mockery of something he'll never get to have.
Meanwhile, Dean is at his wits' end trying to figure out how he can make Sam realize that he is, in fact, trying to get into his pants.