In the 1960s, I was a typical suburban teenager, with hormones raging but with little knowledge or outlet for my desires. My budding sexual frustrations were focused on a couple of girls in school. I was ignorant about sex and didn't know how to release my urges.
So my first masturbation experience came about quite by accident with my younger sister Darlene as my unsuspecting partner. It started innocently: a weekend morning watching TV in my PJs. Darlene also watching, wearing her nightie. My parents upstairs or outside, I can't remember.
We were both laying on the floor. My attention was elsewhere. I was reading a pre-teen magazine that actually belonged to Darlene and started to make fun of one of the articles. Darlene tried to snatch it from my hands. Being bigger and older it was easy to keep it out of her reach. I was laying on my back, holding it out when she plopped on my mid-section, straddling me as she lunged for the magazine. The pressure of her body on my penis made me erect rather quickly.
At first I was a bit embarrassed by my boner, but at the same time, I liked the feeling of her body pressing against mine. Then I quickly noticed that Darlene was making little thrusts of her pelvis as she pretended to grab the magazine from my outstretched hands.
She did it again and said, 'that feels good' and giggled. I was blushing madly, but replied that it felt good too. She did it again and then started to hump, rubbing her nightie-covered pussy against my PJ-covered penis. It seemed like a long time, but only lasted a minute or two before I felt this incredible, intense sensation in my loins and then began ejaculating in my pjs.
I groaned loudly when it happened and then Darlene saw the wet spot in my pants and asked what had happened. I tried to explain, though my knowledge was limited. Darlene told me that she liked to rub herself against objects and would sometimes get an intense tingling and wetness from the sensation.
Needless to say, we did this on several more occasions, always with Darline straddling me. We would do it in our pjs or underpants. But the last time, we were both naked. I think we realized we had gone too far, so we never did it again. Besides, I had figured out how to masturbate solo by then, and could take care of my urges on a daily basis.
But I'll never forget that first time experience with my little sister.