The Girlfriend Experience by rageprufrock http://archiveofourown.org/works/91894?view_adult=true While it's not like Dean hasn't had a couple of truly regrettable hit-and-runs in his sexual history, this is probably the saddest fucking thing that has ever happened to him.
Also the stories of the gentle fall verse http://www.delicious.com/dirtydancer14/dean/castiel+verse%2521storiesofthegentlefall
And by the same author Right Up Over the Wire by liadan14 http://liadan14.livejournal.com/42274.html When Sam finds out about them he's convinced that Dean's possessed/bespelled/being controlled by some supernatural force, and Dean has to come to terms with the fact that yeah, he is actually kinda into guys, before he's able to make Sam believe he's still himself.
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The Girlfriend Experience by rageprufrock
http://archiveofourown.org/works/91894?view_adult=true
While it's not like Dean hasn't had a couple of truly regrettable hit-and-runs in his sexual history, this is probably the saddest fucking thing that has ever happened to him.
Also the stories of the gentle fall verse
http://www.delicious.com/dirtydancer14/dean/castiel+verse%2521storiesofthegentlefall
And by the same author Right Up Over the Wire by liadan14
http://liadan14.livejournal.com/42274.html
When Sam finds out about them he's convinced that Dean's possessed/bespelled/being controlled by some supernatural force, and Dean has to come to terms with the fact that yeah, he is actually kinda into guys, before he's able to make Sam believe he's still himself.