When I was 18
When I was 17 and my sister 18, we lived in a large apartment building in New York. My sister's friend, Doris was my age. Doris and I would often talk and joke around but I never made a pass at her. She was my sister's friend and making a pass never crossed my mind.
One day, Doris was telling me that she met a really nice guy but that he kept pushing her to give him a handjob. I asked why she was telling me about it and she said something about how funny it is that all guy's are into jerking off.
So I went with the flow and asked her if she ever jerked a guy off. She said she didn't because she didn't know how. She said the only time she had seen a naked man was in a magazine.
Eventually, and I don't remember how it actually happened or what was said, but I remember she asked me if I would show her how to jerk a guy off. Wow! I told her I would be pretty embarrassed to be nude in front of her and so she offered to take off her top if I would undress. She promised not to tell my sister and I believe she never did.
I was very nervous but very excited. I agreed to do it. We went into my room and I laid down on my bed. My parents and sister were out. She took off her top as promised. I couldn't believe my eyes. Her breasts were not huge but they were awfully pretty to a 17 year old.
I began to undress and she watched every move. After kicking off my shoes and removing my shirt, my hands slid down to undo my belt. I grabbed the waistband of my pants and underwear at the same time and slipped both down to my ankles and then onto the floor.
I was totally nude with a 6' hardon. My cock throbbing. Doris just stared without saying a word. I remember asking her if she wanted to touch it and she just nodded her head. She took my cock in her hand and I told her to squeeze it just a little tighter. I'm sure I told her to take a firm grip but I don't remember exactly what was said. She started moving her hand up and down and I asked if I could touch her tits. Again she nodded.
I came in about two minutes. It was my first handjob from a girl.
After I came, and cleaned up, she asked me to stand in front of her. I did and I stood with my cock only inches from her face. She took my cock and balls in her hands and just kept exploring my body. She then asked me to turn around and show her my ass. I remember being embarrassed but totally into being an exhibitionist. She touched me all over and examined every part of my body. I got hard again and so she jerked me off a second time.
Later, we got dressed. For some time after that, she jerked me off whenever the opportunity arose (no pun intended). That continued for a couple of years.
Doris and I never were a couple, just two teens with a great friendship. She jerked me many times and I always saw her tits. But she never fully undressed and we never had intercourse. After high school, I went away to college. When I would come home, the handjobs continued. Eventually, I moved away and the friendship faded.