This is one of the earliest memories I have of masturbation. It's when I first learned about how to do it & I was probably 12 years old
My first memory of masturbation happened when I was spending the night at my friend's house. I'll call him Tom. We were both 12, though he was about 5 months older than me. He moved in across the street when I was about 5 years old and we had been best buddies ever since.We were in the same classes at school.
This night I was staying overnight at his house. He had a room of his own above the attached garage, so we had a lot of privacy. We were both running on hormones and spent the night talking about the girls we'd like to see naked. There were three of them that lived in the neighborhood and we had spent many nights sneaking around trying to peek into their bedroom windows. This night we snuck out in our underwear and went down two houses to see if we could peek into Becky's window.
It was a hot night and her window was up about 6 inches. We could see the light on in her room. Her house had a lot of bushes around it so we could get up close to the window. We both carefully peeked in and there she was in her panties and a little top. I looked at Tom and we both grinned and looked back into the window. She had apparently just gotten undressed and was putting some clothes away. She walked back and forth getting clothes out of a basket and putting them in her dresser. She'd bend over and we would see her pretty little butt as she put some panties or shirts in her bottom drawer.
I looked at Tom and had his briefs down and was playing with his peter. I decided to pull mine down and do the same. This was so hot in our young minds. We watched for about 10 minutes hoping she'd get undressed, but it never happened. We decided we better get out of there before we got caught, so we pulled up our underwear and snuck away from the window.
We got back to Tom's house and snuck back in. As soon as we got to his room we were both jabbering away like crazy monkeys, talking about what we had seen. I told him that I really wished she had taken off her panties so we could see her little vagina. We had both been looking at the encyclopedia and new girls were different, but we had never seen the real live thing.
Tom said, 'Man I'm going to jack-off thinking of that!' I asked him what he meant and he asked if I had ever done it. I said I wasn't sure what he meant. In my house we never talked about sex and the only one I could talk to about it was Tom. He said he'd show me how to do it.
He said we both needed to take off our underwear and get naked. I said sure! I had been an exhibitionist for a long time and loved to be seen naked. I was stripped in about 30 seconds and he wasn't far behind me. Both of us had hard dicks. He told me to lay down on the bed and he'd show me how to do it. He took hold of my wiener and started to stroke it up and down. It felt so good I thought I'd die. I told him I never knew this could be so much fun! My dick was getting really hard and feeling good. I wasn't really ready for what he did next. He bent over and took me into his mouth. I nearly screamed out loud but managed to hold it in.
He began running his mouth up and down my little hard peter as I laid back and enjoyed it! I was feeling harder than I ever had, even when we were watching Becky in her panties. He was sucking and I was really enjoying it. He stopped for a minute and asked if I wanted to suck him too. I said sure and he straddled my face. I took him into my mouth and began sucking him like he was sucking me. We both began breathing harder and harder. Pretty soon I felt like I had to pee and told him so. He just kept sucking. Pretty soon I felt like my peter exploded and started moaning around his dick. He started moaning too and I tasted a little liquid in my mouth.
We both laid on the bed in a stupor for about 20 minutes. He then started to play with me again and I returned the favor. We kept doing it for most of the night. Neither one of us had a real load of cum, but we both enjoyed the orgasms that we had over and over again!
This was the start of many nights of enjoyment, and when we both started to shoot a lot of cum it really added to our experience. Oh, yeah, one night when we were about 14 we did see Becky naked in her room. We even got her to come outside and join our little game, but that's another story!