My first time seeing somebody else jack off and cum as well my first time seeing an uncircumcised penis up close.
My first time ever witnessing somebody else masturbate was about 10 years ago when I went on a tour of black colleges on the East Coast. I was 15 at the time and my best friend for the week-long tour was Danny, also 15.
Danny and I had already met two other times before the tour during the 'meet and greets' and we hit it off pretty well. Danny, as I remember him was a light-skinned African American, his brownish hair was braided when I met him the first time, but on the day of the tour I remember that he had an afro. He was also short and thin and it was sort of a running joke among the other participants that his afro was too big for his body or that his neck would be hurt from having to hold up the afro.
The first night we had a third roommate but he wanted to be in the room with his friends that he had made, so adjustments were made and by the second night it was just Danny and me.
Danny started walking around the room in his underwear and I would catch myself staring at him and then I would look away. He sort of had what I would now call a 'six-pack by default' meaning that I don't think he spent much time doing sit ups but he was young and was blessed to not have a huge amount of body fat like I had at the time so his ab muscles were visible. Also I could tell by looking at his boxer briefs that he was quite a bit more endowed than I was despite his body size.
At this point this was still only the second night of a 7-day long tour and we had gotten a knock on the door. Danny jumped into the bed and covered himself as I answered the door and it was one of the chaperones. He said that we needed to be getting to bed within the next 5 minutes because we were going to be heading out early the next morning.
The chaperone leaves and Danny gets out of bed and has an obvious hard-on and now I'm really staring. He says that he needed to 'nut off.' Then he asks me if I ever 'nutted' before, and I had never heard that term used before but I knew what he meant and I answered,
'No.' I was almost 16 at the time and truth be told I had 'nutted' as he put it, probably hundreds of times.
Danny then said that I should do it because it would 'relax me' and then I could sleep. He took down his underwear and his dick was huge and uncircumcised; his balls were about five shades darker than the rest of his body but nice. His pubic hair was the same weird brownish color as his afro was. He had a truly huge dick and sticking out of a small-framed body made it look even more massive.
He then asked me if I was bisexual or gay and I said 'no' and he told me that he thought he might be bisexual but wasn't sure. He walked around with his dick out for about five minutes trying to convince me to do the same but I wouldn't because I was about 5.5 inches on a good day he was probably 5.5 inches coming out of the pool.
After not convincing me to show my dick, Danny jacked off for a good 10 minutes switching from fast to slow. Danny's penis under his foreskin was a shade of purple that I would never forget and his 'head' was shiny and reddish. I was glued to his every move and finally it became clear from his quickening pace and deeper breaths that he was about to blow, he grabbed a pillow.
His cum first missed the pillow and shot onto the bed, then the rest hit the pillow. Each rope landed on the pillow until the last few drops rolled out. He then pulled up his underwear and went into the bathroom. While he was in there I stared at the cum on the pillow and even put my finger in it, it felt warm and slick.
Danny came out with his sweat pants on that he slept in and took the pillow case off the pillow and threw it to the side. He put a t-shirt on the pillow as a pillow case. Later that night I got up and took the pillow case into the bathroom and stared at it a long time before adding my own DNA to the mix.
Although Danny was never shy about being nude in my presence, he didn't jack off in front of me the rest of the trip. The next encounter we had was months later when I went to visit him.
I hope you enjoyed.