Dean tries to get Cas to loose his virginity at yet another strip club. Although he fails to loose it at the strip club that doesn't mean Cas stays a virgin for much longer. Things seemed okay, well- great at the time. But there are a few things that make Cas and Dean go through hell. Lets just say past exes, one night stands, angels, the works.
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A case comes up at a councelling retreat and Sam, Dean and Cas go to check it out. Sam snatches up the only job vacancy forcing Cas and Dean to go in as a couple.
None of them expect the events that unfold (but they kinda do).