I knew Lenny since we were real young. He lived across the street from my house and we played together all the time. As we got older we were just very good friends and never had any kind of sexual contact. We were in each others house a few days a week and would watch tv, listen to music or play video games much of the time none of our parents were home. We talked about everything and at times confided in each other. We talked about sex often but still there was none between us.
One evening we were watching a Seinfeld re-run and it was the episode about masturbation and was very funny. Lenny turned to me and asked me how often I masturbated, not even asking if I did. I think I turned three shades of red because he never asked me anything like that before even though we did talk about sex many times. I wasn't sure what to say and before I could think of anything he began telling me he masturbated a lot every week. After quite awhile I did admit to masturbating without telling him how often and blushing the entire time. A week later I was in his rec. room alone when Lenny went to change clothes. As I walked to the bathroom I had to pass his bedroom. The door was open slightly and he was laying naked on his bed and masturbating. Instead of walking away I just stood there watching him and saw him cum. In all the years I knew him neither he or I had ever seen each other naked.
It was about a month later and we were playing video games. He said he'd be right back and that he was going to change into shorts. This time I didn't have to go to the bathroom but did just to see if he was masturbating again. As I got to his bedroom door again it was open a little and when I peeked in he was again laying on the bed jerking off. As soon as he finished I quickly turned to go to the bathroom and tripped and fell down. Now he knew I saw him and he came out to the hall with a towel around him hollaring at me. I just said I was sorry and I could tell he was embarrassed by it. He was mad at me for a few days and avoided me. So I knocked on his door and apoligized again and everything seemed to be alright. A few weeks went by and everything was back to normal and we actually began talking about me watching him that day. He wasn't mad anymore and after a short time I confessed it was the second time I saw him jerking off. I did tell him the first time was accidental and that I was only going to the bathroom. Then he admitted to me that the more he thought about me seeing him it turned him on. Thats when he asked me if I would like to watch him again. He pointed to his crotch and he did have shorts on, but I could see he had an erection. I told him no even though I really did want to watch him again. Over the next month or so every time he got an erection he would point it out to me and kept asking me to watch him masturbate, and I always said no.
After about two months of him talking about it and asking me I finally told him I would watch him. His mother wasn't home so he sat on the chair pulling down his shorts and underware and I just sat there looking at him. I have to admit I was aroused myself by watching him but never told him I was. After that, each time, neither of his parents were home and I watched him masturbate. After the third or fourth time he was always completely naked. He always encouraged me to masturbate with him and one day I finally did but only put my hand down my jeans to do it. It took months but eventually I started undressing and after him pleading with me many times was comfortable enough to be naked with him. It took several more months before we began masturbating each other and we continued doing it to each other until he went away to college. I had boyfriends but Lenny is the only boy who ever saw me naked. None of them ever touched my breasts or my vagina but I did make out with them. The boyfriend I have now I do have sex with and we masturbate each other often.
Christmas time was the last time I saw Lenny but we were unable to be alone. We do e-mail each other and talk on the phone sometimes. He knows I have a boyfriend but we are planning on being alone together when he is home during Easter vacation. I have really missed him and can't wait.