Under what conditons did you have your first orgasm?

I remember vividly I was around 6. My parents had to give me enemas to help me go poop and mostly I was terrified by being given them but one time I kind of stopped fussing and relaxed somewhat and I felt a tickle down there. I at the time figured it was the enema causing this sensation. Then my mom put me down for a nap and I started to pretend like I was having an enema my poking around my butt with first my finger and then a crayon. I noticed after I poked around down there I once again felt a tickle down there as I poked around. I naturally loved this feeling a lot. It made me curious so I continued to poke around and it felt even better. It got to a point where my body got stiff and I started to breathe harder. It was incredible. Then it was like my entire body tickled all over. It was amazing. It felt so wonderful to me even at this young age. I was hooked ever since. LOL

Hand masturbation as a teen. That was my first ejaculation. I doubt there had been dry orgasms before, though I recall rubbing my penis felt good.

This is very had to answer. Maybe, probably when I was over the knee being punished in school. You can believe or disbelieve that all you want. I say that because my first real memory of masturbation was when I began fantasies. That was around age 7. The subject of the re enactments was spanking. Masturbation at that age was not like we think of as adults. It was accidental bumping into objects or rubbing on things. You know boys are notorious for having reactions at the worst moments. Anyway laying over a pillow pretending it was my teachers lap, self spanking and rocking and bucking all over my pillow. So, no hands really. I had no idea of the actual mechanics of handing it in that way. But I certainly did become good at the motions necessary to repeat the feelings that were building, and the burst at the end. I had no idea what that was. It was AWESOME. Long before the time when there was a mess to clean up after. The excitement of pulling down my own pants while pretending they were being pulled down by my teacher. My underwear. Pretending it was forced and I was fighting.

Yup at that age. Anyway I slapped as hard as I could and tanned my own bum. Seriously just imagine had my best friend came in the house during this. Or family. Anyway tracking backwards it was a school fantasy from what was really happening to me. And if I can pinpoint a guess, I will say that somewhere along the way during one of her spanking sessions on me, my body against her bare lap had a big effect. It just happened that way and planets aligned. Its not like we talked about it after. It was over and she dressed me and off I went to cry and sulk. But through all that, I really believe during all the bucking and kicking and squirming that my body began to react. Maybe, when I discovered through the mix of emotions and slaps, that my little bittles were bare right on her skin.

Not first. But later once it was repeated and I began to settle into accepting the punishment as routine and necessary. And I did ! Once I began to relax into it, I became aware of smaller details. Through all the slaps and the burning and crying when I settled down quiet as she was still slapping. Maybe then a wave came over me there as I squirmed.

At 12 years old.

When I tried to hold my pee with my dick between my legs, I realized that if I squirmed my thighs, the movement produced a kind of pleasurable pain in my penis.

Since I was holding my pee and trying to avoid going to the restroom, and since I associated this sensation with pain I thought I was doing something bad to my body. The thing is, I would do this over and over again when I wanted to pee and the pleasurable pain would grow as long as I rubbed my thighs against my penis. In my mind I knew I was doing something bad (I thought so back then) but I couldn't stop since this "pain" would grow and grow. Now I come to think that probably is something similar at the pain/pleasure you feel when you scratch your scars.

Well the thing is that at the end when I couldn't stand this "pain" anymore, something happend inside my body and I thought that I had "broken" something inside. My underwear would get wet, just a bit. I said to myslef I wouldn't do it anymore but I would again and again.

It was a long time after I had discovered typical masturbation that I realized that this "pain" was actually an orgasm. I can say those were some of the best orgasms I had since they were not "polluted" by desire or sexual thoughts. Just pure physcal pleasure. I couldn't be able to replicate it now since thinking about sex is stuck in my mind in order to get an orgasm.