The Girlfriend Experience by rageprufrock

Title: The Girlfriend Experience
Author: rageprufrock
Fandom: Supernatural
Pairing(s): Dean Winchester/Castiel
Rating: Explicit
Genre: First Time, Humor, Angst (mild)
Word Count: ~15,300

Summary:

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.

Why You Should Read This:

I have this bookmarked at AO3, and have it in my iPhone in my favorites file. Even with that, when I went back this morning and re-read it, I was blown away by the work that was done by this author. What you have here, is two characters who are completely true to canon, in my opinion; up to and including Dean’s history of turning tricks when needed to feed Sammy or keep a roof over their heads, and Castiel trying to figure out how to live with his fading Grace. This piece is brilliantly written and watching these two fall together is a joy.

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