The beginning of the story of how my many adventures with my babysitter got started.
My babysitter, we will call her Michelle, lived in the neighborhood behind my house. We lived on a tree farm inside the city limits, but just a short walk through the woods to her house. She had been watching me after school, on holidays, and during the summer for nearly a year and I had developed a huge crush on her during that time. She was 17 and for my standards then she was pretty. Looking back at pictures and checking her social networking page I see that now and then she was very sexy. She had a very cute face, short dark hair, a small waist, big boobs, and a nice butt. I was very shy but had begun to open up to her a little, still not revealing my crush on her, but talking and such. She would play hot wheels, lego, and anything else I felt like and was always a good sport.
Eventually she began making any game we played about "playing house". She would be my wife and I would be her husband. One day she made our characters have sex, I knew very very little about that as I hadn't had that talk yet, went to a very small private school, and had no TV in our house. I asked her about sex, and she was happy to explain it to me in terms I'd understand. A day or two went by and nothing else happened until one day she asked me if I wanted to learn more about sex. My shyness kicked back in and I remember being a little hesitant when she told me to take off my clothes. She did a little sweet talking and before long there I stood wearing nothing but my tshirt in the middle of the trees on the tree farm.
My penis was soft and I had not yet uncovered the joys of masturbation so on the occasion my penis would get hard I only knew it made it hard to pee and hard to get dressed. She reached down and took my penis in her hand and immediately it sprung to life, ridged and throbbing. She seemed to like this reaction which calmed me. She then with one hand unbuttoned her pants and slid them and her underwear down to he ankles. I was mesmerized by the first pussy I had ever seen. It was glistening wet and had short trimmed pubic hairs in a small diamond shape. She started stroking me while rubbing her pussy. She took my hand and guided it to her pussy I was was never hesitant about that I began rubbing in the same circular pattern she was and she loved it.
Soon I began to have what I thought was the urge to pee and stopped and pulled my pants up. School was out a few short days later and we had decided to go to the neighbors pool. We swam and had a great time playing and chasing each other around the pool. She got tired and swam to the other side of the pool to relax and I kept playing. I then decided to swim up behind her to scare her, but as I got close I heard soft moans, moans I hadn't heard before these didn't sound like painful moans but a good kind of moan. Her face looked as if she was in pure ecstasy and she finally noticed I was watching. She told me to go under water and look at the pool jet. I did as I was told and noticed her pussy was directly in front of it. She had her suit pulled to the side but being that I wore goggles I could clearly see the water blasting against the skin around her pussy as well.
I came up and asked what she was doing and if that felt good. She told me she was masturbating and it felt amazing. She asked if I ever masturbated and I said that I hadn't. She told me that I should try it and pulled me in front of the jet. I was much further away than she was but could still feel the water hitting me and began to get hard again. She reached down and pulled my swim trunks down a little and grabbed hold of my now throbbing cock at the base and gently pushed me towards the jet. She lined up the water perfect to hit just below the head of my hard dick. Within moments of that the combination of her holding my cock and the jet I came like a sex starved monster, shooting rope after rope of young man semen into the jet and all around the pool, more semen than anyone that age should have built up probably.
I was hooked from that moment on and would swim every single chance I got, and always with no shame swim up to a jet and let it bring me to orgasm every time. She and I stayed close companions for years and years until I no longer needed a babysitter, and then I would walk to her house just to "hang out". Before that time came however we had many more experiences, including when she brought another friend, we will also call Michelle, to play with us both.