Who is the most unexpected person you had sex with?

The purple haired lesbian in the improv troupe. I reminded her of an actor she had a geek crush on, and we always flirted aggressively, but right up until things happened I thought it was just playing around. Her identity was really tied up in being a lesbian, but one night when we were REALLY drunk after a show, someone else in the troupe told me that she had a crush on me and later that night we were making out backstage. From what I understand I was the only guy she ever seriously messed around with. We only ever had actual sex once, but fooled around a good bit for a few months. Then she got a crush on my girlfriend and things got weird and we drifted away from the whole thing.

/r/AskRedditAfterDark Thread