This is the story of the first time I ever jacked off in front of or with another guy. My buddy and I were both 12 and it was the summer between sixth and seventh grade. It happened for the first time during sleepover at his house. We both slept in his twin bed and, of course, we both were wearing pajamas. Naturally the talk turned to sex. we were telling each other what we 'knew' about sex. I asked him how he jacked off. I knew how I did it and had heard another guy say he did it by humping his sheets. I was hoping my buddy would reveal a new way that I could jo. Well, to my surprise, my buddy had no clue what I was talking about but he was dying to hear more about the topic. I tried to use words to explain how I would jo and what it was like, but he kept interrupting with stupid questions. He clearly wasn't clear on what I was describing. So, I decided, partly out of frustration and partly because by now I was so hard and horny from talking about it, to pull down my jammy bottoms and showed him. As soon as I slid my jammy bottoms off, his eyes immediately locked onto my rock hard cock. He stammered about how huge it was (I had already begun puberty and mine had acheived adult size). I asked him what his was like and told him since I showed him mine, I get to see his. Reluctantly, he pulled off his jammy bottoms and I could see that his was still child size, but nevertheless, very hard.
After comparing our cocks, he asked me to show him exactly what jacking off was and how to do it. I meant to just show him a few sample strokes but since I was already hard and already very horny and after a few strokes and him watching, I couldn't stop. Jacking off in front of him with him watching me and me able to look at his naked, hard, twitching cock while I jo, I had to keep going till I shot.
As he watched three or four strands of cum shoot from my cock, he freaked. I was terrified he'd tell on me and I figured the only way to make sure he didn't was to get him to jo and shoot too. It took a while but I was able to convince him to try it. As he began to stroke his cock for (he said) the very first time, I quickly saw that he was so bad at stroking his cock (used just thumb and one finger, like he was afraid of it)he would never be able to make himself shoot. I pushed his hand away and took over for him. I was just going to show him a few strokes as an example but when I stopped, he begged me to keep going. At first I hesitated. I worried that I would be weird if I jacked him off till he came. But he begged me to keep going and I didn't want him to tell on me and figured if I kept going and made him cum, there was no way he could tell on me. So I took his cock back into my hand and stroked it like it was mine. It took less than a minute and he shot his very first load from me jacking him off. After that first summer sleep over, we made every excuse we could to have more sleep overs. Each sleep over, we'd wait till parents went to bed, then take off our jammies and we'd always jo ourselves and each other at least 4 or 5 times each night. We always had to sneak two cum soaked socks into the outside trash the next morning after every sleep over. Unfortunately, our fun ended when summer did. He and his family moved out of state before school started again.