I've read a lot of first time stories here, and love them. Here's mine.
When I was a kid, Saturday mornings were always a marathon caroon watching session for my brother and I. It seems we always wanted to sleep in, but after getting up for school every day, we automatically woke up, so we'd shuffle down to the family room and lay on the couch to watch cartoons. It was a big couch, and I would lay on one end and my brother on the other.
From as early an age as I can remember, we'd lay in our boxers and T-shirts, which was our normal sleeping attire. I noticed when I was really young that my brother (who was 3 years older) would play with his penis while we watched. Sometimes he would do it through the cloth of his boxers, and sometimes he'd reach his hand inside and do it. Of course I emulated what he did, and found it felt really good. I'd get a little boner and just play with it while watching TV. When I got older I saw other boys doing that, so obviously it is a common practice if boys have the privacy to do so. We did, since our parents were able to sleep in on Saturdays, and seldom got up before 10 am.
So that was just the normal thing we did every Saturday morning, and there was no connotation to it; we were both just doing what felt good.
By the time I was about 8 and my brother 11, I sometimes noticed that he got a little tense, closed his eyes, and shook a little after doing it a while, but I didn't think anything of it. When that happened he always had his hand inside his boxers, and was holding still.
My own fondling was really pleasurable. I'd finger my penis till it got hard, then play with it. The best was gripping my foreskin and rubbing the head inside through it, sometimes rotating, sometimes pulling the foreskin back and forth. That felt really nice.
Then one wonderful Saturday morning it happened. The good feelings seemed to build up to something. I felt I had to pee, but I could tell that wasn't it. Suddenly my penis got really hard and sensitive, and began to throb with the most wonderful feeling. Even to this day I can't describe an orgasm in words, but this wonderful throbbing feeling radiated from the head of my penis and all through my groin. I tensed and held on tight, clamping my thighs together, and I must have yelled out in some way, because before it was done my brother was looking at me with a big smile on his face.
As the orgasm died away and I was panting, I looked over at my brother, and for the first time he had his penis out of the fly of his boxers, and he was rubbing it fast out in the open. He asked me, 'Is that the first time that's happened to you?'
I gasped 'yes,' and kept holding my penis, which was still tingling.
'I do that all the time,' he said, and closed his eyes and kept rubbing out in plain sight, and soon he, too, stiffened and held still, and I could see his penis throbbing.
After he recovered, we talked about it for a while, and he said he loved doing that. I agreed.
For two or three weeks we did that every Saturday morning, and I came to really look forward to it. Then I noticed one night that my brother was doing it in bed at night (we shared a room), so I did, too. From then on until he went off to college three years ago, we did it almost every night. I learned a lot from him, especially when he started to ejaculate a year after I first did it, and I enjoyed watching him shoot and looked forward to when I could. He said it wasn't all that great, because it meant you had to be more careful when and where you did it because of the mess that had to be dealt with. Exploring that subject, I found that he did it other places than in bed at night and on the couch on Saturdays. He admitted he used to do that on the school bus, and a couple of times in class at school, but once the semen came, he had to stop.
I never got up the nerve to do it in a public place, but I enjoyed his stories. When he did it, he would always tell me that night while we were doing it in bed, and it excited me. I always wondered if all his stories were true, but he did do it on a public bus once when I was with him, so I knew at least some of the stories were true.