The story of my first orgasm when I was a boy.
When I was younger, my mom was friends with a coworker who had a daughter who was older than me, named Jamie. She had two older brothers and an older sister, all three of whom were in or graduated from college at the time. I think this gave her a bit of a complex about being the youngest, but we bonded easily. We had a lot of fun together. We would have sleepovers and hang out playing video games. I remember once we used an easy bake oven to make brownies, and while we were waiting for it to finish we made barbies have sex.
One time when I was there, I was spending the night but had not brought a change of clothes. It was winter and we had been out in the snow, building snow forts, snowmen, etc., and I was soaked from the waist down. Her mom told Jamie to give me some clothes (since I was actually just about her size, definitely shorter though) while she put mine in the laundry.
My shirt was dry and I kept that on, but Jamie had given me a pair of white socks with these frilly cuffs around the ankle, a pair of purple cotton panties, and these kind of ugly, lime green pyjama bottoms, but I remember thinking, at least they weren't pink. I was a little taken aback at how casual it was that I was wearing her underwear but it was her mom's idea and I just accepted what adults said at the time.
Jamie wasted no time telling me how cute I looked as we resumed our play. The frills of the socks were peeking out of the bottom of the pyjama pants that were a bit tight and definitely showed the outline of the girls' panties I was wearing. I started to get a boner being dressed like that with her. At that time I had not yet started masturbating. I was getting boners but didn't really know what to do with them. Eventually it just went away and it was out of my mind until the next time.
Jamie noticed my boner and commented on it. It was uncomfortable to talk about my erection, and I told her I was sorry and I didn't know why it got like that. She asked if I wanted to know, and I said I did. She went to her door and looked out in the hall, checking, I assume, to see if anyone was there, and then closed the door again. She had me sit on the bed and then pushed me back so that I was laying down.
Jamie got on top of me so that she was straddling me, sitting right on my hard dick stuffed tight in her panties. She began to tickle me and there was nothing I could do with the position she had established. She turned around on me and started tickling my feet in her frilly socks. I was able to twist over and she stopped and said she would tell me why I got erections.
She explained that it was what happened when boys got excited. She had learned all this in sex ed and said she knew how to fix them, but she would have to touch it. I said it would be ok and she slowly placed her hand on my dick. She was really slow and seemed to be exploring, herself a bit nervous. My dick was up against my tummy, held down by the panties. She rubbed her hand up and down it, stroking my small shaft.
She stopped and said it would be a lot easier if I took the pyjama pants off. I just nodded, unable to really speak at this point. She scooted herself back and pulled the pyjamas down from my hips, leaving me in her panties and socks with a raging hard-on. She was rubbed her hand over the panties then moved so she was behind me, her legs outside of mine. She held me around my waist while her other hand rubbed at my dick.
I'm not sure she really knew what she was doing, because from what I know now, I would not say she seemed experienced by any means. It just felt amazing with her rubbing me through the fabric. The light friction combined with the softness of her underwear, and the whole situation really, had me extremely horny.
I could feel her little tits pressing into my back as she gasped in my ear about how I was going to feel really good. It already felt really good with her rubbing me, but the orgasm itself totally snuck up on me. I had no idea what was happening when all of a sudden my cock exploded in pleasure. I had no idea something so amazing could happen. I didn't shoot any cum, but from that moment I was hooked. I came down from it while she wrapped her arms around me and held me, exhausted.
We were together several more times before I moved, and I've never seen her since. Maybe I'll write about the other times.