My first recollection of my own sexuality is about 5th grade or so. I remember having some sort of sore muscle in my arm or back, so I went to get the electronic back massager we had. I was sitting on my bed using this when it occurred to me for some reason I shall never know: "I wonder what this would feel like on my penis?" Not being one to wonder for long, I put it down there, and it felt good — so I decided to leave it there. After a few minutes, everything began to tense up and I didn't know if it was hurting or feeling good, but I left it there, and finally, I had my first orgasm.
When I was about 10 my brother (a year and a half older) and I went into the woods near home and saw a neighbor kid of 17 or 18 who was sitting under a little tree hut we had built. It was actually on his folks' land but a long way from his house, and I didn't think he even knew it was there. He had his pants down and was stroking what to me looked like a huge joint, compared to my little weenie. I'd never even seen an erection before or pubic hair but was intrigued. A better word today would be turned on, but I didn't know that then. When he ejaculated all over, I was mesmerized.
Although I probably had a hand around my fetal penis, I didn't masturbate to orgasm until I was about 14. A kid in the 8th grade lunchroom said something about "whacking off" and made a circle with his thumb and index finger. Up and down he gestured. I waited until a quiet Sunday afternoon when nobody was home. At that time I was still small enough to fit into an old canvas laundry bag, and I wore it over my naked body. The feel of the material stimulated me.
I am 20 years old, and it has been a long journey to be as comfortable with masturbation as I am now. My life and masturbation crossed paths when I was 12. My mother had dropped off some books, about all the changes to expect in my body, STDs, and all that fun stuff. I was reading them thoroughly, always hiding because I didn't want her to know I was reading them.
I am a 53-year-old man living in the U.K. I have been a regular (perhaps even a compulsive) masturbator all my life. However, I have also had a continual struggle to reconcile my feelings of guilt, the condemnation of my church, and the disinformation from my guardians with the pleasure I have derived from this universal activity.
I distinctly remember the first time I masturbated — it was after reading a book about puberty when I was 12. I was lying in bed and I had an erection. I didn't know about masturbation yet, but I did know about things like oral sex. For some reason, I thought, "I wonder what it feels like..." and tried, unsuccessfully, to get my penis into my mouth. Instead, I put saliva in my hand and put it on my erection — I thought of it as a simulation of my mouth.
I grew up in the 1950s in Calvinistic South Africa. It was a very straight-laced and conservative place — still is, in many ways. My mom was very religious, and sex, in any form, was not a subject of discussion. At school the word "sex" was never used. We would talk of "gender" or, maybe, male and female. A form might ask what your "gender" was. At least the modern forms say "sex" — to which I always want to respond, "Yes, please!"
Although I am only 14, I pride myself in my long and fruitful masturbation life. I first discovered masturbation when I was only 10. Bracing my penis on my stomach, I used to do it by taking my index and middle finger and rubbing vigorously until I orgasmed. (Of course, nothing came out.) When I discovered the cool feeling that resulted, I rushed to tell all my friends how to do it. They went home and tried it, and all came back to 4th grade thanking me deeply. In 4th grade, I kept up the habit a solid 3 times a day.
I grew up in a cool family. I'm the eldest in our only-boys family, and that the fact that we have no sisters makes us aware that we have nothing to hide from each other — we all have penises, and we know for a fact that we all masturbate. That's probably why we give each other enough privacy to do whatever we want to do.
I am unable to remember when my penis first revealed its abilities to me. Masturbation was something I was born with — just as many children are born with a thumb-sucking habit, I was born with a penis-rubbing habit. As a toddler, the dreaded "naptime" was always a pleasure session. However, because I began masturbating before I ever had any idea of its significance, I did not masturbate in the traditional style.