Back when I worked in retail I used to go to conferences every year. Once, on the last night of this particular conference, i found myself closing down the bar with three ladies I'd gotten to know over the course of four days. Two of these ladies were roomates and suggested we continue on to their room where they had a few bottles of wine. So we did. These rooms were actually suites with a kitchen and a dining table. We sat at the table drinking and talking and one of the ladies was absentmindedly cutting and recutting a deck of cards. Someone (probably me) jokingly suggested we play strip poker. Everybody laughed, but no one really said yes or no. We did eventually play a hand, which I lost, and one of the ladies, again joking, told me to take something off. I made a big production of taking off my shoe, and suddenly we were off and running. The problem was, I kept losing. Before I knew it, I was down to my boxers and none of them had lost more than two shoes and a sock. When I lost the next hand they went wild laughing and high fiveing. As I stood up for the final humiliation, or so I thought, I turned my back on them, pulled down my boxers and for all practical purposes mooned them. When I turned to face them, I cupped my privates with my hands. They were still laughing and clapping, but insisted I pull my hands away. I refused, sitting back down but promising to stand again with my hands on my head if I lost the next hand.
I lost the next hand.
By this point, I had an erection and was scared to get up. I confessed my dilema, but they had little sympathy. So, I stood as promised, with my hands on my head. Not suprisingly, I was a bit dizzy, and when I put my hands on my head I lost my equalibrium and started to walk, fall sideways until I landed heavily on the couch.
The ladies decided that I had officially lost and would now have to be their waiter for the rest of the evening. I was allowed to put my boxers back on, but they decided to improvise and make a sort of "boxer thong." This is a lot like a wedgie. The material in front is gathered and kind of pulled down and then behind until most of it is pulled up in the back as it uncomfortably goes up your crack. And this is how I was for about an hour, serving drinks and walking funny. As one woman nodded off the other two decided to call it a night. I put on the rest of my clothes and went back to my room pulled off my shirt and pants and promptly passed out on my bed. I awoke the next morning to the sound of my roomate in the shower. As my head cleared a bit, I realised that I was on top of the sheets with my "boxer thong" still in tact. Fortunately, my roomate never mentioned it and neither did I. I left the company later that year, so I never did get a rematch.