I was very shy and backwards as a kid, and not at all wise about sexual matters. My parents didn't really talk about sex, and I was too embarrassed to ask. I picked up some things from talking to kids at school, but most of it was over my head and abstract. I had heard of "jacking off" and "masturbation," but I didn't even know they were the same thing, or what they really meant.
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catholic
Leg-weakening
Birds and bees
I first discovered masturbation when I was 13 1/2. It was at the end of a summer during which I had many hours of privacy in the house. I was extremely naive as a child, rather protected, and hadn't had any instructions or hints from my friends or older brother about sex. In our family sexual things were never discussed, so it isn't surprising that my older brother hadn't said anything. My mother had given me a "birds and bees" book to read, but it was so obscure it didn't answer anything. It just made me more confused.
Bird
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.
Horseback riding
I have had several interesting times since I started masturbating. When I was about 9 years old, I worked on a neighbor's farm. They had a son in his 30s, unmarried, whom I worked with a lot. He would feel me up and put my hand on his penis, and eventually I started to masturbate him. To me his penis was so big, but to a 9-year-old, I guess it was. Then one day when I was about 10, I walked into the barn and caught my cousin going at it. He was 5 years older than me. He was to the point that he couldn't stop, so I saw him ejaculate.
Catch-22
My individual discovery of masturbation has been an absolute godsend to me. I come from a great family — very Irish Catholic, and not very talkative on the sexual front, but nevertheless a terrific family. However, a lot of things — in fact, 99.9% of the things I know about sex — came from my own "research," if you will. That research started with surreptitiously sneaking Playboy, Penthouse, and Hustler magazines into my house, reading them in the bathroom or bedroom, and masturbating like a maniac.
Draining spinal fluid
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.
Dr. boner
By the time I was 9 or 10 years old, I had discovered how good it felt to have an erection. Some of my friends started to talk about it, and we decided to show one another our erections. We would take out our penises and touch and squeeze ourselves until we got hard. It was a big joke, except that it felt so good. Nobody knew anything about masturbation, so we stopped there.
Voyage of discovery
I think I was about 6 or 7 when I discovered that rubbing my penis felt really good — not just nice, as it had felt when I was younger. It started with a "rosy palm" trick: grabbing my penis with one hand and rubbing the very tip of my penis with the palm of the other. The feelings were incredibly intense, and I couldn't do it for very long. A few times, I was able to do this with my friend John, who was about same age. We did this secretly, as somehow we knew it might get us into trouble.
The joy of solo sex
I started masturbating around 5th grade. We had a talk on it in sex-ed, and I just had to try. It was quite nice. I was kind of a bad student then, and even didn't pick up on most of the sex-ed stuff, but this I did remember. At the time I would just make a fist and jerk away. I liked the feeling a lot. Then after a while something sudden would happen, and everything would be strange and I would stop. I later learned that this was orgasm.
Hush hush
I first discovered masturbation when I was about 10, almost 11. I lived in a small town with not a lot to do, and I had one friend who was 14 or 15 at the time (can't remember for sure). Anyway he would come over and we would play super Nintendo or screw around or anything. One time he brought over a porn video and asked if I wanted to watch it, so I said, sure -- why not? So we did, and he asked if he could play with his penis. I said go for it. He told me to do it too, and I asked how, and he told me to just rub my penis. So I did.