This is an actual account of my first masturbation session with a female.
I was a very naive 13 year old boy who had just become interested in sex though I had not yet discovered the joys of masturbation. Our neighbors had a 16 year old daughter who was a tomboy and played baseball with me and we generally hung out together. She was fairly well developed and I was beginning to notice her somewhat large breasts that bounced around in her tee shirt.
One early summer afternoon when our parents were at work we were playing catch in the back yard when she asked me if I wanted to see something in the woodshed that was on the back of their large yard. I followed her into the woodshed and she closed and locked the door which I thought was strange. Then she went and sat down on a bench and told me that she had seen me looking at her 'titties'. I turned red but before I could say anything she asked if I wanted to see them and I nodded yes. She took her tee shirt off and was not wearing a bra. Her breasts were probably about size 34C and hung just a little. What interested me most were her large brown nipples that had become hard and pointed. She told me to touch them which I did, rubbing my hands over her erect nipples. She took her hand and started to rub her crotch area through her yellow shorts and I noticed that my penis was hard and poking out the front of my shorts. She continued to rub herself for a while and told me that she could see that I had a 'boner'. Then she asked me if I would 'jack off' for her and let her watch. I told her that I did not know what that was and she said for me to take off my shorts and she would show me how to do it. I dropped my shorts and my little 5 inch boner stuck almost straight up and seemed to be throbbing. She said it was a nice 'cock' and that she would like to show me her 'pussy' while she showed me how to jack off. She stood up and took off her shorts. I was kind of scared by at the same time thrilled to see my first real live pussy. It was covered downy black hair and I could see her labia poking out. As she fingered herself I could see that her fingers were wet. She sat back down and told me to move closer, then took my cock in her hand and slowly stroked it up and down rubbing my foreskin back and forth over my swollen glans. At the same time she continued to finger her pussy, rubbing what I later found out to be her clitoris. She continued to jack my cock and it did not take long for me to begin to have a funny sensation in my cock, like I had to pee, when all of a sudden my cock began to jerk and twitch, then squirt out a small amount of watery fluid which landed on her breasts. At the same time she must have had an orgasm because her eyes rolled back and she moaned loudly, then stopped. Then she told me that was how to jack off and that boys did it all the time.
We continued to have mutual masturbation sessions all summer and she showed my how to finger her pussy and make her cum. Toward the end of summer I was ejaculating copious amounts of thick white cum when she jacked me off.
She moved away with her family that fall and I never saw her again. I still like to masturbate, often thinking of my very first orgasm with her. I also like to ejaculate on my woman's belly which I find to be very erotic.