This is a true story, though the names have been changed to protect the innocent (and guilty).
Back in my college days I lived in a house(NOT a frat house) that had anywhere from seven to ten coed students living there every semester. In an effort to get caught up on credits I decided to go to a session of summer school, and the house only had five people staying there at the time, three guys and two girls.
One of the girls was Kathy, a very cute girl working on post-graduate classes who was a few years older than me. I would've been interested in her except for one thing—one of the other guys in the house, a good friend, really had the hots for her. I spent a lot of time counseling him on how to get her to go out with him, so the thought of me pursuing her was not an option.
Unfortunately, after a month of valiant pursuit it was pretty clear that my friend had no chance. I had become good friends with Kathy, and she made it pretty clear that she just wasn't interested in the guy. From time to time I even felt like she was interested in me, but I fought off the urge to pursue anything.
Anyway, as fate would have it, Kathy and I ended up alone together at the house for a weekend. Actually, I was going to be alone, but then at the last minute she changed her plans—in retrospect, I might've expected something was up.
So Friday afternoon comes along, and Kathy and I are shooting pool at the house pool table. I had become a pretty solid pool player over the years, and Kathy had not played much, so I was putting a pretty good beating on her. I can't remember exactly how it got started, but at some point we started joking about playing strip pool, where if you lose a game you lose an article of clothing, to be removed later. The whole time we were playing, it was just a big joke, and we were laughing and having a great time with it.
The funniest part was that I suddenly could not win a game. I'd run half the table and then scratch on the eight ball, or Kathy would come up with some crazy shot to win a game. When she won the first game I promised I'd take off my shirt later—thinking I would clearly win it back—and then I'd go double or nothing. Four or five unlucky games later, I had bet away all my clothes. I'll have to admit that at some point I started to get warm to the idea that I would be getting naked in front of Kathy. The exhibitionist in me was starting to not mind losing. At some point during my losing streak I had decided that I might just make it more than just a joke ...
So we get through the final double or nothing game—I think I scratched, on purpose—and we're having a good laugh about how she's won all my clothes, and I tell her I guess its time for me to pay up.
At this point, I'm fairly sure she was still joking about the whole thing, but when I suggest that we do the pay-ups in my bedroom, she was still laughing, but starting to wonder how far I'd go. At that point, I wasn't sure myself.