This all started when I was around eleven. Two of my friends and I all kind of figured out about masturbation around the same time. It started as the normal truth or dare stuff (running around the house naked, etc.), but it soon went further. A few stories in particular I would like to share.
My two friends, let's call them Brian and Ken, and I would have sleepovers a lot and generally spend a lot of time together. One day we were at Ken's house up in his room playing truth or dare. At this point we had all jerked off before so it was old news, but had never really done it together. Brian decided to dare all three of us to jerk for 30 seconds. Ken and I happilly obliged so we all whipped it out and started stroking. Man it was great just watching each other stroke, cause we knew how good it felt. After the 30 seconds were up we all stopped and went back downstairs because we were being called. The rest of the story just involve me and Ken.
Ken had a pool at his house so we would always go swimming if it was warm enough. One day we started to play a little game where we would go under water and take turns doing things. It first started with just pulling our bathing suits down to show our schlongs. As we kept going it went to pulling down our suits and stroking for a few seconds, and then to pulling each other's down and stroking each other. Sometimes we would go over toward the jets in the pool and one person would stroke and the other would go down and watch underwater! At this point we knew we had to finish the deed.
We had to wait a little while since it would obviously be apparent how hard we were when we got out of the pool, but once we were relaxed enough, we would get out and go up to his room to 'change'. When we got upstairs we would strip down and just start stroking. We would watch each other's technique, size, how hard we each were. He was uncut and I was cut. It was so much fun just watching each other jerk off, so exciting!!! After a few minutes we would each pronounce our time and cum on some old underwear. These kind of sessions happened almost everytime we would go swimming.
As time went on our sleepovers became more adventurous. We would stroke each other a lot, making each other cum. Most times we would try to cum at the same time.
We still keep in touch and from time to time will stroke online with each other, which isn't as good, but it's better than solo!! One time a few years back we did get together at his college over one summer. We were both a little nervous because we hadn't stroked with each other in years, but once we stripped down and started it was great!!
Wish I had more, but that covers most of my childhood masturbation!