This was really my one and only masturbation buddy ever if you exclude my wonderful wife.
I lived in an apartment complex with my mother when I was between the ages of ten and seventeen. When I was about 14 years old and just beginning to masturbate there was a field near my apartment, back then the field did not have any development on it. It was just a huge empty field with brown grass, dirt and things people had thrown away such as TV's, refrigerators, etc.
One night I had masturbated with my window open and I liked the feeling of the cold air on my body so eventually I got the idea of going to the field at night. At first I would walk around with my penis out sticking it back in whenever I heard a car but then it progressed to masturbation and finally I started to take all my clothes off and masturbate.
I felt comfortable jacking off because the field was big and the only light came from the street lights that were not even pointing towards the field in the first place and the moon. I had confirmed that at night cars passing by could not see me. There was enough light for me to see what I was doing but not enough for people to see me doing it. I felt very secure about not being caught so when I went to this field I would take my time and masturbate.
There was a Mexican kid about my age that I knew well but we weren't necessarily friends. We knew most of the same people but unfortunately I was the butt of all of his jokes, so if I was hanging around friends and he came around I would feel very uncomfortable and find an excuse to leave. One day I was at the apartment pool with friends and 'Ricardo' the Mexican kid came around, he was looking at me and making the universal jack-off hand gesture and he kept saying 'Yeh, you know what that means.'
When I left the pool area 'Ricardo' followed me and said that he knew that I jacked off in the field at night and that I probably got naked and ran around.
I thought I was going to pass out when he said that because it was true but I wasn't convinced that he really had seen me because I had always been very careful to make sure that nobody was around. I always had my guard up and I was trying to think of a time when I had my guard down and he could have seen me. 'Ricardo' kept accusing me but I didn't want to confirm and I couldn't convincingly deny that I had been in the field doing all the things he was saying, so I just ignored him.
'Ricardo' told me that if I came to the field that night around 10pm he would be waiting for me with some 'jack off pictures' as he called them. The first thing to go through my mind was not 'I have a jack-off buddy now' I was thinking that this was a setup and I imagined some of his friends running up to me snapping my picture while I stood there with my hand gripped around my manhood. I was still very curious though because I had never had a jack off partner but had tried unsuccessfully to get one through dropping hints to my friends or trying to start 'truth or dare' games and hoping I would get dared to expose myself.
When it was a little after 10pm I went to the field and I saw 'Ricardo', I was standing on the sidewalk and he was in the field he kept motioning for me to come over but I didn't come.
'Ricardo' ran up to me and asked why I wasn't going over to him. He said that he had a bunch of porno and he was boned and to prove it he stuck his erection out of his jeans right there on the sidewalk under the street lamp. A car whizzed by and he turned toward it once it had passed us and made a quick jacking motion on his penis. That made me more comfortable and hornier as well, we walked out into the field and the whole time he had his dick out, I told him that I thought he was going to set me up to be humiliated and he said that he would never do that because it would be 'f-cked up.'
When we were far enough in the field 'Ricardo' asked me to get my dick out too and I did I had pre-cum on the tip of my dick because I was so excited to jack off with another person for the first time.
My penis at that time was near six inches long and maybe almost the same measurement as far as girth and I had a patch of pubic hair covering half of my mound.
'Ricardo' was not circumcised and his penis was the first one I had seen like that, it's head was sticking up over his foreskin and was much darker than the rest of his body, his testicles were also dark. His penis was probably about the same length and width as mine and to my surprise he had a lot of pubic hair, it was like a jungle of black hair.
I dared him to get naked and he did and after he took off his last stitch of clothing I also got nude. We touched ourselves, we touched each other and 'Ricardo' let me explore his foreskin. At the end we stood real close, faced each other and ejaculated at the same time onto each other's bare skin.
When all was said and done I had to ask how he knew that I jacked off in the field and he told me that he didn't know for sure but had seen me going to the field really late one night and just knew that the only reason to go to a deserted field, alone and late at night was to jack-off.
'Ricardo' and I became very close friends and I was no longer the butt of all his jokes, we basically hid a stash of porn in an old TV and went into the field to jack off often but rarely used the porn because we were more interested in watching each other. We mutually masturbated in that field regularly for a couple of years and in that time we once had a girl he knew come out with us and a boy cousin of 'Ricardo' as well. We stopped when we were 16 because 'Ricardo' complained that it was too 'gay' for guys our age to be jacking off together.
It's funny how things happen because I am now married with a one year old son and 'Ricardo' is a gay rights activist.