My Sexual Beginnings: Jack

Sun, 03/09/2008 - 23:00
Submitted by Anonymous

Dear Betty:

In reading your book and making notes of chronological references I deduct that you and I are about of the same generation. I was born 6/1/25. It is nice to relate to someone of your own age.

On the subject of masturbation, my first sexual experience was around 12 1/2. Prior to my first experience, a neighbor girl and I initiated a fool-around relationship. I said, I'll show you mine if you will show me yours. I think this girl was about 13 and I was 11 1/2 at the time. We found some secluded place where we could look at one another and make comparisons. The girl was quite explicit in her demonstration of her genitals pulling back the hood from the clitoris for my observation. As I recall the little nubbin stood up proudly and she picked a speck of "cheese from it, saying "that's natural." I thought, "is that all there is to it?" She didn't say anything about her vagina and I didn't ask. Of course I made a display of my penis to her. According to the other boys, my prick was way over size, and I was, for that reason, a little reluctant to show it to her, but when saw saw it all my fears were dispersed because she found it acceptable.

My curiosity overwhelmed me. When I had to pee it was simple enough. But I wondered how a girl did it, to see a girl pee was my main ambition again we found a secluded place for secret observation and I was rewarded with the sight if urine passing from from the genital area of my new found girl playmate. "So that's why they have to sit down!"

Shortly after this, after dark, the two of us climbed up to the back of a billboard and sat there watching the traffic go by on the street below, our seating was rather precarious but still stable enough for my girl and me. She was wearing a light dress and lifted it high and persuaded me to put my hand down the front of her belly, past the waist band of her panties to her pussy which at that time was a little hairy. The hairs were damp and I wondered if it was piss. Nevertheless, I did as she asked and started rubbing there. She was quite explicit in her directions saying "faster or slower, up or down, this side or that side, and when she got real wet there I stopped because I thought she was pissing on my hand. I did notice though that the wetness was rather slippery, and that gave rise to great concern.

I thought something went wrong; especially because she was breathing rather hard, and her continence was not like her regular self. At this point, she pulled my hand away from herself and replaced it with her own hand to her crotch. I turned my head and watched her as she lifted her head high and wildly rocked her hips back and forth. I thought she had gone completely crazy but, in due time she regained her composure and seemed to be at peace with the world.

About one or two nights later we scaled another set of billboards, this time back to back with a lattice work on the bottom We fooled around there while feeling one another when she started getting really serious. In defense I climbed down to the ground to prepare for my escape. When I got to the ground she was right there and on top of me. I soon found that she had a dress on but, no panties. She pulled me to the ground, and straddled me and began to take my trousers off. She explained that her cousins did it to her all the time so, it wouldn't hurt if she put my penis into her pussy. My belt was unbuckled and my pants down far enough for the action she desired. In fact, her bare cunt was on my belly while my erection was easily in her reach. Then and there, I totally panicked, grabbed my pants and belt and ran like hell home.

A few nights later while I was out on the street playing some sort of kid game, I hi with my young lady friend in some place. She was sitting next to me, so I tried to put my hand in her crouch where she usually liked it. I was totally surprised when she hauled off and slugged me on the face. Well, that was the end of that adolescent relationship. She wouldn't have anything at all to do with me after that.

After this, it was only a matter of days when I was alone in the house after school. I was in the bathroom examining my "manhood" and contemplating the next move. A nearly empty jar of Vaseline was at hand so, I slipped it over the head of my prick and started to massage it back and forth. It was a good feeling, so I continued until suddenly a funny feeling overcame me. I picked up the tempo and suddenly, I removed the Vaseline jar to see white stuff issuing from the head of my prick. It DID feel good, but, I wondered again if something had gone wrong. I talked to other older kids about what happened and they proudly said, that, I had become a man.

Well, thereafter, I had many, many solo sessions; and I have to admit, they were guilt-free. That was my first after school activity every day. That was a convenient time of day for me because, my last class in junior high school was study period. A girl whose desk was in the aisle next to me and just ahead had chosen study period as her relief period, and I was in a perfect vantage point for observing her as she "jilled off." She supplied herself with a long, nearly unused pencil which she would slip, eraser first, under her dress and between partially parted legs. Her head laid on her other arm on the desk as subtle manipulations with her right hand and arm with the pencil got underway underneath her dress. I was sure of what she was doing when finally her hips would grind back and forth while she let out an inaudible sigh and her face blushed with the crimson of youth.

In short time the bell would ring and we kids were homeward bound. I had a 12 ½ year old hard-on that wouldn't quit and was compelled to carry my books home in front of me so people wouldn't notice. As you can probably understand, as soon as I got home, the first thing on the agenda was to masturbate. I'm sure that Ma knew what was going on in the bathroom with my prolonged stays, and on one occasion she remarked from outside the door that I was very "self-abusive." This of course was a reflection of typical Victorian attitude. But even in 1938, a more liberal understanding was starting to prevail.

Jack R., Sacramento, CA

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Sat, 09/29/2012 - 06:12
Ashleen (not verified)

Heeey! Jack,your story was so great! actually,this is my first time to know and heard what boys are actually doing when they have they're first sexual begginings haha and this is so great tho. ;) I love it and the story is really fantastic. :D <3<3<3