Where it happened: school
I was finishing up PE, it was Senior Day, and alot had skipped school. Our PE class was small, about 15 kids, but 4 of us had not skipped. So me and 3 of my best friends had just finished playing flag football. We were required to wear some sort of athletic protection. So the Coach had said play good and I will be in the Teachers Lounge while you guys are playing. We all said okay. It was 10 minutes before class was over. We had to get showered and get ready to go home. We all put away the flags and cones. We went to the locker room and no one was thier. I started undressing, and the other 3 friends walked in and started undressing as well. I pulled down my gym shorts to expose my boxer briefs and my cup, the others had on normal jockstraps. they started talking about how I was an idiot for wearing the best stuff available. They said that I need to be more normal and wear an actual jockstrap. They started giving me crap for that. they dared me to try one on, my friend threw me a clean one and i put it on. They said to put my cup in it and see how it looked. I did and went over to the mirror. they said it looked good. They walked into the showers with thier jock straps on, and I followed. we got into the showers and we started squirting soap at each other. I slipped an fell on the ground, and we all started laughing. Sam came over and started to point out that my cup had fallen out, i looked and I had a weak erection. I laughed and they all asked me how a jockstrap felt. i said it felt great. then tom squirted soap all over my jockstrap. It tickled and i got a hard erection. we laughed and jerry mentioned that soap helps to lube when having sex. i asked if it was true, and he told me to try it on him. I began to stick my dick up his ass, and it went in smoothly. I began to pund my ballsack up against him. then sam told me to stop, i pulled out and sam started to jack me off. I came after a bit and it was the biggest any of them had seen. we got out after a while and we got home 30 minutes later, we had told our parents we had asked the teachers for homework help.