It all started that previous summer. I had just entered highschool. I knew I like boys since I was young, I just didn't know if I liked girls. So I am in the marching band and we are required to go to summer practices. I knew of a couple gay/bi kids that were in highschool based on drama I heard my older sister talking about. So when I went to the first rehearsal, I met one of the gay guys. He was junior and we will call him Josh. We instantly connected. At this time I had not come out to anyone except my one best friend. As time went on we started texting and calling each other. We decided to meet in the bathroom one day at rehearsal. When I went in, I got cold feet and left. We still met up at the park and nothing went further than kissing.
Skipping all the way to the beginning of November, my school was putting on the musical Cinderella. Being an excellent actor and okay singer, I tried out and got a part. Josh was in the pit(where kids play the music for the musical). It came down to crunch time where we had to dress in our costumes everyday. My costume consisted of an elegant shirt and green tights. This shirt was way too short and I felt very exposed. One day, both the pit and cast were practicing together when the director called for a 20 minute break. I saw Josh in one of the chairs in the audience seating. I went and sat by him.
The theatre was semi dark and we were in the back. We started talking when he put his hand on my thigh. This sent a jolt through me. I did the same. He then proceeded to go up and lifted up my waist band and slipped his hand in. By this time I was completely hard. I then slipped my hand into his pants. We started fondling each other. Every now and then people would walk by and we had to quickly escape each others pants. Josh was the sterotypical pretty boy, around 5'8', blonde hair and blue eyes. His penis was something else. I never saw it but I felt it. I'm pretty sure he is uncut, like me, with a huge head and I would guess it was seven and a half inches long and pretty thick. As time progressed we both started to breathe hard. He finally whispered in my ear that he was about to come. When he did it was never ending. This was sending me closer and closer until I couldn't take it anymore. I told him I was there and he started to jerk faster. My muscles tightened and I came. I came the most I have ever in my life. My hand was still in his pants caressing his now softening penis.
Time was dwindling and I had to go back up on stage to run my scene. In a desperate attempt to cover up the wetness on my tights, Josh threw me a pair of his gym shorts. I put them on, smiled and left. The whole time I was on stage people were giving me weird looks wondering why I had his shorts on.
This happened once more, but that is a story for another time.