I remember vividly the first time that I masturbated to orgasm. I used to imagine seeing one of the girls at school naked before I went to sleep each night. I'd get very hard, but I really didn't know what to do with it. I was quite young and very naive. I knew that 'having sex' involved putting your penis inside a girl, but I hadn't put it completely together in my head. I would often lay on my stomach and and move my hips, rubbing my penis on the bed. I did that often, but I didn't really try to bring myself to orgasm. I just did what felt good.
I had no idea what an orgasm was. I almost had one a few times, but it frightened me, so I stopped. I remember once I was enjoying myself as usual, and I felt a spasm. It was so strong that it almost hurt. I stopped because it was so powerful, and I just didn't know what was going on. I thought that maybe I'd pee or something. I just felt like I was losing control, and I was afraid of that. I remember that I didn't get that close too often, but when I did, I was fascinated. I was really worried about peeing my bed, so fear kept me from going any further.
Then, late one night, I was rubbing my penis against the mattress, and I spasmed again. I stopped, pushed my hips away from the mattress, and tried to hold back, but it was too late! Every muscle in my body was tensed as I fought to control myself, but I just couldn't. I continued to try to stop it, but it was way too powerful. There I was, sort of on my hands and knees, ejaculating into my pajamas. I remember groaning loudly when it hit me, and then with the next spasm I let out an tortured cry. I collapsed into a puddle, gasping and squirming.
I was completely terrified! I thought for sure everyone in the house had heard me. I had no idea what had just happened! I lay very still for a long while, listening for footsteps coming down the stairs. The house was silent. I was really wet down there. I pulled down my pajamas to look, and to my surprise, I smelled nothing like urine. I was so surprised! I can't say that it felt good, it was shocking and very powerful. I had discovered something entirely new! I was very curious to try to make it happen again, because I wanted to know what had happened. I was in too much of a daze to make sense of it. Exhausted, I fell asleep.
When I woke up, my bed and my pajamas were still soaking wet. I wanted to try it again, but I really didn't want to make such a mess. I decided to try making it happen again, but this time while sitting on the toilet in the nude. I was hard just thinking about it.
I sat on the toilet, and began to rub in a way similar to how I was rubbing myself in bed. It felt good, but hurt a little to rub so vigorously. I switched to the technique that I've been using for the rest of my life: I lined up my fingers just below my glans, put my thumb on the other side, and rubbed in a circular motion. This was the first time that I purposely masturbated to orgasm. This time I really paid attention to what I was doing, and what I was feeling. At first, I wasn't sure if I could do it again! I was really hard, and it didn't take long. Instead of fighting the feeling, I let go. Oh my! I exploded! This time, because I had my penis in my hand, I could apply pressure to it, and it felt much better. In fact, it was the best thing that I'd ever felt! I cried out again, but again no one paid any attention to me. What an experience! I could give myself such pleasure, and I could do it pretty much whenever I wanted! I realized that there was a limit soon after that. As soon as I finished ejaculating, I tried it again. I was able to ejaculate again, but it was much harder the second time. I didn't attempt a third try.
As a teen, I was quite obsessed with it. I lived in the country, so I had limited mobility. I didn't have a girlfriend, so I just enjoyed my body on my own.
That was my first orgasm. It's pretty normal, I think, but for me it was a life changing experience.