With Jessica

Jessica has been one of my closest friends since about sixth grade. We would always hang out during school, and sometimes after school. We were both the same age and same grade and had many of the same classes together until high school. We both knew that each other masturbated because we had talked about it before, but we had never actually done it with each other before. I had been masturbating since I was 13 or so and she had been masturbating a lot longer than I had.

One day when we were 14 and I think in the ninth grade, we had a sleep over at my house just the two of us. I thought it would be fun and I had no intention of doing anything sexual when I invited her. I lived with my parents and my brother who was 17 at the time, but he always stayed out of the way when I had company.

I think it was a Friday because we did not have school the next day. She came home with me after school and when we got to my house we were watching television for a while. Then it became time for dinner, so we ate, and then we did different things throughout the night. When it became dark, she said that she was going to take a shower. So she did and I was minding my own business. She came out and was in her pajamas. She was wearing a t-shirt with no bra and some bottoms. Once I saw her now I was slightly starting to get horny, but I kept it to myself and went about the night. It became time for us to go to bed. We really had no choice on where we were going to sleep in my room because I did not have a chair or couch, unless she wanted to sleep on the floor but she didn't. We both slept in my bed because it was a queen and it was large enough for the both of us. We both climbed under the covers and turned out the light. We both did not want to go to sleep so we kept talking about something that was interesting to us. We were talking for a while and somehow the topic got onto boys in school that we thought were cute. Then of course I ended up getting horny but I didn't want to say anything about it. I usually masturbate once every night before I go to bed because that is the only time I have privacy since my door does not lock.

I had the idea that I would just wait until she went to sleep then I would masturbate, but then something changed. I was turning over in my bed so I could get comfortable and I accidentally knocked her boob. She replied with an Ooooo, and then I sort of wanted this to go on a bit further. I chuckled and so did she. Then it seemed like she was trying to make me wet by asking questions like how do you usually masturbate and those kind of things.

Eventually, it went far enough to where she asked if I wanted to masturbate right now. We waited until about one in the morning so that we would be sure that my parents were asleep. I quietly said yes, even though I was very excited. We both took turns just masturbating in front of each other. We slid the covers down and I slid down my pants and took off my top. I was only 14, I think I was a b cup by then and I had a decent amount of pubic hair. I began to stick my fingers inside myself, and then Jessica told me to stop because she wanted to finger me. I agreed and she stuck her fingers inside me and it felt heavenly. I had never been fingered or ever seen another girl naked so this was a big first for me. She slid her fingers in and out and I was extremely wet and excited by this point. She did this for a little bit longer until I had this extraordinary orgasm that I could not believe. My body started to shake involuntarily, but it felt so good. I also let out a few moans and I made a small wet spot on the blanket. It took me a minute to get myself back on track and regain my control.

Then Jessica looked at me and said that it was my turn. So I moved closer to her and began to slip my fingers inside of her. She had a great body, what looked like b cups, and a shaved vagina. That is something I had never even thought about at this point in time. I moved my fingers in and out of her wet vagina as she quietly moaned and squirmed. After about the same time as me, she clinched up and had her orgasm. She was very wet and I almost came again by just watching her. She said thank you and told me that it was also a first for her to ever be fingered.

We cleaned up ourselves and went to sleep, but we also did the same thing again in the morning before anyone woke up.

This became a tradition for us, we did it every time we were alone at home or was having a sleep over. Those were fun times, but now I have moved to a different country even, but we still talk every once in a while. We are now both 29 going on thirty.