Some time ago I had a friend round to stay. His parents were away for the weekend and his sister was at someone else's house, so he wanted to come and stay with me.
I came to know him because I dated his sister, he is small, his voice is unbroken and he has light brown wavy hair with dark brown eyes.
We stayed in one of the outbuildings that has been converted into a house type dwelling, so it's away from the house. He came up at around 7:30 pm, and his parents went. We ended up playing some video games for a while, but then we watched some panel show type comedy when it got to about 9pm.
One of these panel shows started talking about masturbation, and of course this friend, who is younger than me, didn't know what they were talking about, and coincidentally asked me.
He asked me what you do, which I explained, and of course I mentioned it feels great.
I then offered to show him how, but he was hesitant, although I assured him it would be kept between us.
He started by undoing his tie (like me he hadn't changed out of uniform). Then he proceeded to remove his jumper and unbutton his shirt. He then removed his socks.
He undid his fly and button and dropped his trousers. He was wearing briefs instead of boxers like I was expecting. He then dropped the y-fronts to expose his penis. After he had undressed he sat on the sofa while I removed my shirt, tie and jumper.
I then dropped my trousers, although unlike him I was wearing loose boxers which were pushed out by the erection I had. I then removed my boxers. We were both now naked although he didn't have an erection, so I showed him some pornography to give him his first erection.
I showed him what to do, and then he started to do it while I was slowly pleasuring myself. I then shot a load of cum on the floor. He was incredibly shocked and asked me what it was. I told him it was called ejaculation (he hadn't done sex ed yet) and he would do it when he starts puberty.
When I had finished he carried on, by this point he was lying on the carpet and I was above him, viewing his penis and scrotum, which was hairless.
He then shook slightly and cried out in his high pitched voice. Saying it was an amazing feeling.
He did it another five times that night, only going to sleep at 3am. At one point we even did it to each other with our hands, and he rubbed his penis between my legs until he reached orgasm.
We did the same thing the following month, where he just stayed for a sleepover, in which he had a very small amount of pubic hair sprouting on his scrotum.
This time he produced a very small amount of cum, only a drip though. He said he loved the feeling and would love to make this a habit.
We even tried it outside at one point, at midnight, being a light night we crept outside both fully naked up to a mossy field and pleasured each other. He said this was the best feeling yet.
We are now very close friends.
I hope you enjoyed reading.