First Pussy

This entry is the last in a three part series I am calling “First Feels”. Yesterday I wrote about “First Boob”, and today’s entry is all about “First Pussy”.

Eleanor and I dated for a short time, but mutually decided to call it off. She had a crush on another friend of mind that I introduced her to, and I developed a crush on Jamie. That crush on Jamie, as you can imagine, caused a small rift between Rob and I. Luckily we had a strong friendship and quickly settled the issue and continued to hang out.

Jamie and I had been dating for a while and progressed from first to second base in a few weeks and our sexual tensions were running high. Her parents worked odd hours, so when I would go over, we pretty much had the place to ourselves. In typical teen fashion, we spent little time talking, and lots of time making out. By then, I had become a pretty good boob man, I learned quickly and knew what to do and how to do it. But it wasn’t enough for me, I wanted to proceed to third base and touch her pussy; unfortunately I was too shy to try.

Little did I know, Jamie wanted me to proceed to third base as well. One day we were making out on the couch, sitting next to each other, but had our bodies turned so I could play with her tits. Jamie suddenly pulled away, looked me in the eyes and held up three fingers. For a split second I had no clue what she was talking about, then it clicked, 3rd base.

We went back to making out for a minute or two and my hand found her thigh. It slowly moved up her leg, moving to her inner thigh and I then started rubbing her pussy. All I remember of that moment was the heat through her sweatpants. She then pushed her hips out and took off her pants, leaving her sitting there in her panties. Again, my hand went back to her crotch, this time over her panties, rubbing blindly. She reached her hand down and pulled her panties to one side, and I saw it for the first time, a pussy. I remember she had black pubic hair, not too thick, not too coarse.

I had no clue what to do at that point, this was a new and very complicated piece of human anatomy. We kissed again, my hand exploring this new and wet thing between her legs. I remember feeling her clit, but not knowing at all what it was, or what I was supposed to do with it. As my hand explored downward, I found the hole and attempted to stick a finger inside of her. Unfortunately at that angle, it was uncomfortable for her and she said “Ow”. A moment after, we heard a car door close and she picked up her pants and ran into the bathroom. I quickly adjusted my penis in my pants.

Her dad came in and gave me a look. We exchanged greetings and he asked what were doing, I explained that we were just watching some TV. I realize now he didn’t believe me, but at the time, I thought I got away with it. I though I was able to play with his daughters pussy and he was oblivious! Man was I stupid.