First Time Sex Stories #5: Sneaky Little Squirt

First Time Sex Stories #5: Sneaky Little Squirt
By Missy Younglove


Author’s Note: This work is based on a true experience that was related to me via email.


When I was 12, there was a neighbor boy my age who used to come over and play with me in the evenings. He was a little bit nerdy and I was kind of chubby so neither of us was very popular.

We took great comfort in each other’s friendship, though, and would often sit on my front steps and chat for hours. We never really talked about sex since we didn’t know who might be in earshot, but we eventually got to the point where we’d sit very close together so that our bodies could touch each other as much as possible without being obvious. Sometimes we’d discretely hold hands for a few minutes, but our palms always got sweaty with anxiety about being seen and made fun of by kids playing in the street.

One evening, just as dusk turned into twilight, he timidly began to stroke the inside of my thigh up near the knee. I tried to be nonchalant about it, but it was one of the most exciting moments of my young life. I suddenly knew that my physical interest in him was mutual and that some of my not-so-innocent romantic fantasies about him could actually happen. I nearly swooned as, for the first time in my life, I felt my body respond in all of the womanly ways.

Each evening after that, he would sneak a hand beneath my leg and stroke the inside of my thigh as soon as the shadows began to fall over us. I never objected and as the days went by, his strokes moved closer and closer to my crotch.

My pussy got very wet the first time he touched me and the farther up my leg he stroked, the wetter I got. It finally got to the point where I had to wash my shorts and panties in the shower every night and blow them dry along with my hair so that my mother wouldn’t see the stains. It was a small price to pay, though, and I started wearing very tight but stretchy shorts on the nights he came over.

One evening, he finally stuck his fingers inside the hem of my shorts. When I told him how nice it felt, he stroked me all the way to my underwear. I was dying for him to touch my pussy, but his fingers couldn’t get any farther than the outside of one of my cunt lips without it being obvious to any onlookers what he was doing. The best he could do was to rub his pinky around on my plump, sensitive pussy lip. That made my vagina flow like a river, too.

I reciprocated, of course. It was the early ’80s and high-cut, loose shorts were the style for boys so I had no problem slipping my hand in there. His thighs were so silky smooth that they felt like a girl’s. I loved caressing them.

Unfortunately, it was also a time when most boys wore tightie-whities, so I was ultimately no better off than he was. I could rub his soft, warm scrotum through his underwear with my pinky but that was all. Since I was an only child, the male apparatus was still a big mystery to me and my limited access didn’t help the situation at all.

One summer night, after we’d gotten each other all worked up, he said he wanted to touch my skin and that I’d like it but we’d have to find a private place or we could get into big trouble. We thought of a few places, but discarded each one until we were left with the shed in my backyard.

My mom was in the kitchen cooking dinner, so we sneaked back there. The shed was still very hot and filled with junk so there was no place to lie down or even sit. We had to stand up but were so horny that we didn’t care.

I remember being very excited about doing something so new and scary.