I was rather a naïve boy back in the 7th grade, when my neighbor, Jenny (not her real name), taught me how to masturbate. I know that sounds a bit strange, but it actually happened. Since it is still so vivid in my nearly photographic memory (age-wise I’m now a junior at Stanford), I’m using quotes that are pretty much accurate. Here’ what happened.
I grew up in a really religious family—Catholic to be exact. The subject of sex, my access to the Internet, my father having NO discernable sex magazines around, our carefully screened TV viewing and very limited and carefully monitored access to the Internet resulted in that high degree of naiveté. Oh…and I’m an only child.
Jenny lived right next door. We were born a month apart. We were like brother and sister growing up. We went to the same school and had the same friends. Our parents got us into tennis at an early age, which helped keep both of us in good physical shape.
Even though her parents and mine were miles apart in the department of religion, nonetheless they got along very well. We sometimes did family camping and hiking trips together.
Jenny’s sister, Christy (also not her real name), is 4 years older than Jenny. I mention her here because she becomes quite important pretty quickly.
Now that you have some background, back to the 7th grade. Jenny was at my house one day during the summer before that memorable year started. Out of the blue, she said, “So, Michael, do masturbate?”
“What’s that,” I said.
“It’s when you take out your penis and you rub it and it gets really big and you get this wonderful feeling down there and you shoot this white stuff all over.”
“What the fuck are you talking about, Jenny”? Yep, even though I was raised by straight-laced parents, my rebellion was the use of really colorful, often foul language. Jenny was as colorful in her expressions as was I.
“Masturbation, just like I said.”
“Nope. I guess I never heard of it.” I’ve been waking up in the morning and my penis is hard, but eventually it goes away.”
“You can make it go away faster by masturbating – guys call it “jacking off.”
“How the fuck did you learn that shit, Jenny?
“I’ve got a lot more freedom at my house than you do, Michael. Both my mom and dad work, sometimes into the evenings. Christy is my babysitter, and she’s huge into sex with guys and she doesn’t want me to grow up naïve and unprepared for life. Also, my parents don’t check anything we do on the Internet, and we’re careful to wipe out our history when we look at stuff. So I’ve learned a lot from watching stuff on there.”
“What kinda stuff, Jenn?”
“All kinds of shit. Kids fucking, adults too, gay and lesbian sex, orgies…you name it.”
“Wow. I had no idea you did that.”
“Yes. Like for only the last month or so though, since Christy thought I needed to be educated. You want to watch some of it too?”
“How? You know my parents rules about coming home right after school and how they call and check up on me to be sure I’m at home.”
“I know. So here’s what we can do. I can bring over my laptop. Our house’s wi fi will reach your house and we can watch some stuff that way. Your parents will never know.
So that’s how my “learning experience” got its start. My mom and dad never got home from work until at least 6:00. That semester, with sports and all, Jenn and I had 2 days during the week when we could have 3 hours together.
The first day we got together, Jenn found some great fuck videos. I was completely mesmerized. The people in the video were having a blast. They only looked to be about 18 or so, not much older than Jenn and I.
Of course, I immediately got a hardon, which Jenn pointed out immediately.
“Michael, you’ve got a boner.”
“Duh! Look what we’re watching. Doesn’t it make you horny too?”
“Like crazy horny, Michael. Hey…wanna masturbate together?”
None of the videos we watched that day had guys masturbating, and I was humble enough not to pretend I knew what to do. So I told Jenn, “Ya know, I really don’t know how.”
“I can show you, Michael. Wanna let me?”
So here goes another new chapter: Jenn seeing me naked. But I was smart enough to try to strike a deal by telling her she had to get naked too, to which she agreed. But before either of us got naked, I had another question. “How do YOU masturbate?”
Jenn said she plays with her pussy. Fortunately, from the videos we watched, I saw enough girls begging to have the guy’s cock shoved up their pussies that I knew what a pussy was. Jenn said that when she massages it, she gets the same feeling that I would get when I jack off (new terminology for my vocabulary that day).
I must admit, for a kid that had never even jacked off before, I was really jumping into the frying pan with both feet. And I observed to Jenn that we have always only been best buddies and that we had never even kissed. Jenn took care of that right away. She observed that she thought I’d never ask, and she put both of her arms around my neck and looked into my eyes with an expression I had never seen her make, which today I can only say was pure lust. She was hot.
So we both undressed for the first time in front of each other. Jenn took my shirt off and undid my belt buckle and pulled down my tennis shorts and I kicked them and my shoes off. She had been in swimming that day, so she had on some running shorts and a blouse thing (describing girls’ clothing is not my forte). I helped her out of her blouse first and then undid her bra strap. That released two nicely developing tits that I could not resist feeling right away. They were exquisite. Her nipples were perky and hard. I emulated what I saw in the videos we watched and sucked both of them for about 5 minutes. She loved it and she was breathing hard the whole time.
Then it was time for me to help her get out of her shorts. That revealed a real live pussy for me for the very first time. But it had no pubic hair. Then she explained that she had a little, but that her sister had taught her how to shave it and that guys liked it that way.
I had never been so hard in my life. It actually hurt and it was begging for release…soon. Jenn said she was surprised at how big my cock was for my age. I loved hearing that! She put her arms around my neck and she kissed me again. My cock slid between her legs, just outside of her magic chamber of pleasure.
Then she broke away and told me it was time that I learn how to jack off. We lay on the bed and she proceeded to jack me off for the first time in my life. And it didn’t take long for me to shoot and get it all over my stomach. She said that next time, I can do it myself. Then she showed me how she does herself. It didn’t take long before she too had a powerful orgasm.
After about two weeks we were sucking each other. She loved to eat my cum and I loved having my head buried between her thighs, sucking her juices and making her cum with my tongue and my fingers (she like two inside of her).
By the second semester of the 7th grade, Christy said we could play at their house any time we wanted when she was “babysitting” Jenn. The only requirement was that we had to use safe sex, which we agreed to do from day one anyhow.
As more time rolled along, there were times when late at night, I would sneak out of the house after I allegedly went to bed and go over and fuck Jenn. And, believe it or not, Christy joined us in bed from time to time too. Hot body, big tits, and loved anal (Jenn did not). More about that if anyone is interested.
By 9th grade, we had 8 friends that were really into sex, so we formed our secret “sex club.” Between all 10 of us, there was always at least one house where things could happen and no one would find out. The rules were very strict. NO means NO and protection had to be used. We had some bi kids in the group and 2 gay guys. All of us felt really comfortable around each other and no one cared who was fucking whom, or whether it was in the ass or the pussy or the mouth.
Jenn now goes to another college. When we get together, she tells me about all the guys she fucks and I do the same (about the girls I fuck, that is!). Those conversations really get us horny and we wind up in long fuck sessions. Christy is engaged at this writing, but when we are at home, she still joins us for a romp in the sack. She is beautiful, perfect body, toned, long blond hair, and a nice set of tits, albeit not terribly large but VERY sensitive, and a shaved pussy that is flawlessly perfect in every detail, not to mention great tasting. It feels good having an “older” woman in the mix. More later if anyone is interested.
