I began the process of discovering self-pleasuring in the summer before 7th grade at, of all places, a church retreat. A kid at the pool we went to was staying over by the jet where the water comes out, watching a girl. When I asked what he was doing, he said I was too young to understand (which confused me, because I thought I was older than he was), but he did say that it "felt good."
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taboo
Oh-so-great
Bygone ben-wa ball
As a female, I'm always intrigued to find out about the coming-of-age experiences of the opposite sex. I love the JackinWorld Biographies because not only are they sometimes a turn-on, but they provide amazing insight into men in general. Though the majority of your readership might not care about a girl's masturbation experiences, I'm willing to bet some people might find female information a little interesting for a change.
Body vs. machine
Prior to beginning my life of masturbation, I had discovered my father's stash of "dirty" magazines. This was probably around age 10. I knew that I enjoyed looking at the pictures of nude women (more for intrigue than anything else at that point), but at the time, I didn't know what masturbation was, nor did I ever think about touching myself. My mother caught me looking at the magazines once and told me not to look at them. However, she didn't mention anything about sex or masturbation, not then and not ever.
My best toy
Where I grew up, in a very conservative state, things like masturbation were not even talked about. It seems to me that Idaho might be a bit on the homophobic side. Also, for some reason, some people have the unhealthy attitude that if you masturbate you are gay, when obviously as many straight people masturbate as gays do. At least in southeastern Idaho, that is the attitude. I never did have shower experiences with other guys because no one ever took a shower in P.E. I don't know how other people pulled it off without smelling horrible, because I had a terrible time with B.O.
Dicky parties
My first sexual experience was, believe it or not, in kindergarten during nap time. A little classmate by the name of Joey used to sleep next to me on a separate mat. Well, on this particular day I failed to fall into the usual slumber and opened my eyes to see Joey playing "innocently" with what I referred to at the time as his peepee. I raised my hand and told the teacher that Joey was not asleep. She told me I wasn't asleep, either, and sent both of us to the time-out closet. Needless to say, Joey and I got bored in the dark closet.
Cupped hands
I discovered masturbation at age 15, which I suppose is quite late. My friends in school were increasingly talking about "wanking," and through these conversations (and the hand-actions) I learned what it was all about but had never actually tried it myself. One night I was feeling particularly horny, so gave it a go, using the simple "fist" method that most people start with. It felt better than I had expected. However, when the orgasm came, I didn't know what was happening, and I suddenly realized I was ejaculating and had nothing to catch it in.
Paper trail
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.
New urine
I remember my first orgasm as clearly as if it happened a moment ago. It was a momentous event and I had absolutely no idea what had happened. Obviously I must have been masturbating long before I could orgasm, which was also long before there was an Internet or JackinWorld or even widely available pornography. I can say without a shadow of doubt I masturbated, because it felt good even before I could orgasm.
Bidet on business
I remember playing "doctor" with a neighbor girl as early as age 5. This excited me a great deal, and it felt good for her (or me) to rub my erection. (I think I have always had erections). But I never got to an orgasm from it.
Convergence
I had finished taking a bath. The thought came to me about what the guys at school were saying quietly: "moving back and forth, up and down." I had a fine erection, and the opportunity was present for a bit of self-discovery. For me it was one of the finest discoveries of my life, and at that moment, it was probably one of the most powerful. It seemed quite natural stroking back and forth, and the pleasure of the sensation was surely going somewhere that seemed both mysterious and exquisite. The intensity of that first ejaculation was both memorable and physically powerful.