This site is cool!
I was spending the night at my cousins, (I was aged 13 at the time) and I had never jacked off before. Well this is what happened.
My cousin was having a friend spend the night (they were 16) and I had to spend the night there also because my parents were out of town, and so I packed my bags and my games console and I walked over to my uncles. I went downstairs and they were playing video games (lets say my cousin' name is Brett and his friend is John). So I played some games with them and they said they were going out for the night and I could do whatever I wanted to.
It was about 9:00pm and they left taking his dad's truck.(His dad was also out with some friends), and so I watched tv for about an hour and some soft porn came on and I got very horny. I started to rub my crotch feeling my cock getting hard and then I saw headlights pull in. I got startled and ran to the spare bedroom where I was sleeping and I heard Brett and John come in.
I had just remebered I forgot to turn the tv off. Too late, they had walked in and come downstairs, the tv was never shut off. I could hear like a moan coming from John so I crept out, not to be seen into the living room and I saw Brett jacking off John. I was startled and I ran back to my room. I think they heard me and came to my room and talked to me about what I saw. Then Brett asked me if I ever jacked off and I said no. He asked if I wanted to see what it was like.
Me being very horny said yes, and so I took off my pants and boxers and Brett winked at John. At this point I was confused, then John took my cock into his hands, it was about four inches cut and started jacking me off. It wasn't long before I shot my load right onto his hand and arm. I felt really bad but Brett just laughed and John seemed okay about the mess. That was how I learned about jacking off.