I just sent in a post about watching my brother do the deed in bed at night. Here is the story of my first orgasm.
When I was 11, I had been watching my brother masturbate in bed at night for about 4 years. For some reason I never tried it myself, though I enjoyed watching him, and found it very arousing. That would all change one day on the way to school.
We had a minivan that could hold 6 people, and my mother would drive several of the kids to school every morning. The first day of school I climbed in first, so got into the right rear seat. A kid from up the street, who was older than me by 3 years, got in next, and sat next to me in the middle, and another kid got in the right seat.
We were wearing shorts, and for some reason the skin on skin contact with the boy next to me in the crowded seat was somewhat arousing, and I got a boner. I don't know why. In his process of getting settled in, he put his hand on my upper thigh and pushed so he could slide his butt around to get comfortable. He went to do it again, but missed my thigh, and momentarily had his hand right over my hard little penis. I don't think he did it on purpose, but he noticed my boner, and I got a little embarrassed. He hesitated for a second, then grabbed my boner lightly between his fingers and gripped it twice while saying, 'toot, toot.' I don't know why he said that, but it broke the tension, and we both laughed. He noticed I didn't make any effort to push his hand away, so he left it there, an began fondling my penis through my shorts. It of course felt really good, so I didn't want him to stop. He did that all the way to school.
The next day I got in first like before, and he made a point to follow me. This time he had a light jacket with him (not on), and let it slip onto my lap. Then he put his hand under it and played with my penis again. While doing that, he reached for my zipper and pulled it down, and reached in. He tried to get into my underwear, but it was difficult, but he finally did have my hard little penis between his fingers, and it felt even better than the day before.
I thought about that all day at school, and decided to make things easier the next day. When I got dressed, I left off my underwear and instead slipped them into my backpack so I could put them on in the bathroom at school, and headed to the car with just my shorts, freeballing it.
That day was a repeat of the day before, but when he got my zipper open and found I didn't have any underwear on, he looked at me in surprise and I gave him a sheepish grin. He had easy access, and played with me under his jacket. It felt better and better as he played with it, and I could feel something coming, but unfortunately we arrived at school before anything happened, so I had to zip up quickly and get out, with my penis really tingling.
The next day was the big day. I just knew something was going to happen. I again left my underwear off, and as soon as we were settled in the car he had my penis out and was stroking it. It felt better and better, and suddenly my whole body tensed, and my penis started a wonderful throbbing, and waves of pleasure washed over me. Finally I knew what my brother felt when he did his nightly ritual, and it was wonderful. I had to reach down and hold his hand still since my penis was suddenly incredibly sensitive. He stopped and looked at me, and I know I was flushed, so he knew that I had had an orgasm. He smiled with satisfaction.
That became a daily habit with us, him bringing me to orgasm every day on the way to school. I once asked if I could do it to him, but he declined, saying it would be too messy and people would notice. After having watched my brother shoot, I knew what he was talking about, so I just accepted his favors without question.