Steve and I were in eighth grade. It was a Friday night before we had a basketball tournament. The tournament was far away from the town we lived in, so we stayed in a hotel. Steve's mom and aunt got a room for themselves and Steve and I got our own room. We swam a little in the hotel pool before we went back to our room to go to bed.
Being boys in eighth grade on a Friday night, we couldn't sleep. We watched TV for a while, but the later the night went on, the TV programmes got worse and worse. We were still not tired enough to go to sleep. I brought some playing cards out of my bag that I had packed along. We played a few card games, which was kind of boring with only two people. So we decided to play checkers. To throw a little twist into the game, the loser of the game would have to strip off some article of clothing.
We played this style for several games, by that time we were both fully naked, lying on the floor, stomachs down. At this point, I was getting turned on. We next made the stipulation that the loser of the next game would have to jerk off. I won the game, so Steve had to jerk off. He went into the bathroom and jerked off into a wad of toilet paper. While he was busy in the bathroom, I got busy myself.
After that excitement, there was no way we could get to sleep any time soon. Steve suggested we play truth or dare. I went along with it. Since playing the truth portion of the game is pretty dull, we decided to forego that aspect of the game and play only dare. We started the game off with some absurd dares like to streak down the hallway. Neither of us really wanted to do that too badly.
Steve finally dared me to jerk off on the bed with him in the room. I decided to give it a whirl. He said he would stay on the floor so he couldn't actually see me. The only noise he made was some laughing when he saw the bed shake. Finally at about 4:00 in the morning, we fell asleep. The next morning we had to be up and ready to play in the tournament at 9:00am. It was a short night, but a very memorable one nonetheless.