My uncle is 10 yrs older than me and I always looked up to him like an older brother. He always helped me and I could always talk to him about anything, he is awesome. My Mom worked nights sometimes so I spent the night at my uncles apartment. For many years I saw him change clothes and shower all the time. Sometimes I got a boner and he said that was normal, and he told me he got them too. I saw him hard some mornings but I never saw him touch his cock. Lots of nights we talked in bed before sleeping. One night when I was about 11 I told him some things I heard in school about boys masturbating. He said it was normal, and all guys do it privately, and some day my cock would tingle and vibrate so much I would love it. After that I touched my cock a lot while alone but it took me a few months more to discover an orgasm. After my first orgasm, I told him and he was happy for me. He said it was cool to jack off. He told me to do it in private, like he did. I asked him if I could see him jack off, but he said No, we needed to do it more privately. Some nights when I slept over with him, I jacked myself off while he was asleep. I never worried if he woke up, because he said it was cool. I secretly hoped I would catch him jack off, but I never did. Some mornings as he slept, I saw his morning hard-on and I was amazed at how big it was compared to mine.
One night as we went to bed when I was 12 I said boys at school had told me about ejaculation, and asked him to explain. As we sat on the bed in our underwear, he explained semen, ejaculation and wet dreams. I was erect hearing about this, and looked at his underwear and could see his cock hard, which excited me more. Then I saw a wet spot on his briefs and said 'Wow, it looks like you ejaculated.' He explained the wet spot was called Pre-Cum, then explained it happens when dudes think about sex or are aroused. From all of this exciting conversation, I went to the bathroom to jack off alone.
A few months later near my 13th birthday I had my first ejaculation. I was so anxious to tell him, and he was happy for me. I asked him if he did the same, and squirted CUM also, and he said he did. At that time I was jacking 2 or 3 times a day and asked if that was normal. He laughed and said yes it was normal. I asked how often he jacked off, and he did not want to say, but admitted when he was my age he jacked off several times a day for a few years.
One hot summer night a few weeks later, I got in the mood to jack off while sleeping over. He was asleep, or so I thought, so I jacked for awhile under the sheet, then pushed the sheet down because I was so hot on this summer night. Then I saw my uncle's cock inside his briefs, it was hard with the head of his cock sticking out of the waistband. It got me so excited looking at his hard cock, I jacked even harder and I was breathing fast. There was just enough light for me to see the head of my uncle's hard cock glistening with pre-cum, then I looked up at him. His eyes were open and he was watching me jack off. He did not say anything or do anything, he just watched. I stopped jacking for a minute, but I was so excited I continued to touch myself. I kept looking down at his cock again, and I heard his breathing faster as I jacked myself off. I was so excited I kept jacking and looking at his cock, then up at his eyes as he stared at my cock. The head of his cock swelled larger, and the entire head was outside his briefs. Pre-Cum was dripping from his cock, and he said that only happened if he was really aroused. It excited me so much to know he was so aroused, I wanted to touch him so bad. The closer I got to orgasm, the less I resisted the temptation to touch him. He was breathing heavier, I could tell he was as aroused as me, and his cock was so big compared to my little cock with only a few pubic hairs.
As my body started to quiver closer to CUM, my left hand moved to his belly. My hand stopped on his belly and I looked into his eyes. He did not try to stop me. He was silent. I tested his reaction as I pushed my hand down his belly, then under his briefs and under his hard cock and felt his pubic hair, again he did not resist. Pre-Cum was dripping on my hand. By now my orgasm was starting, I moved my hand to touch his cock and he whimpered and gasped a quick breath as the palm of my hand slid over the head of his slippery cock. With so much pre-cum my hand was sliding down the shaft of his cock with my fingers toward his balls. He moaned. Our eyes stayed connected, I no longer looked at his cock. He started to quiver like me, he took quick gasping breaths. As I started to CUM and shoot my two drops of semen on my belly, I grabbed his cock firmly and jerked him hard. He CAME immediately. I could not believe how much CUM he squirted, it filled my hand, ropes of cum were all over my arm and even under my armpit. His entire body squirmed as he moaned and whimpered. When he relaxed I still had his cock in my hand, and I laid there for awhile holding it as it got soft in my hand. We were both silent, and just looked into each others eyes.
When we finished, he told me we needed to resist the temptation and never do that again. He said whenever I sleep over, the sofa would be a better place to sleep. After that he was much more careful about us not being nude together, and we never slept in the same bed again. I guess I hoped we could do it again, but it was our only time. After that, I jacked off many times remembering the feel of his cum squirting in my hand. He stayed being an awesome uncle and I could always talk to him honestly about sex after that. It was awkward for a few days, but we were even closer after that night.