This happened four years ago in my house with my best friend
My name is Brian and this is how I learned how to masturbate from my best friend, whose name is also Brian. I'm Caucasian, 5'4' at the time (my nickname was 'the midget') with short brown hair and an average (I think) body. The other Brian is Chinese, 5'6' and had short black hair with glasses and is a year older than me but was like a big brother to me. He came over one day after school so we could do homework and hang out. We finished our chemistry homework after an hour of fumbling with the formulas and then retired to my room so we could just talk without being interrupted by my family. Now for some background information, we've never talked about sex or masturbation that much, but he's admitted to doing it once or twice a night. At the time I tried it once but I never orgasmed because I didn't know about it so I stopped doing it. I also felt guilty whenever I touched my penis so I would stop immediately.
I was sitting on my bed facing him, who was sitting on the couch in my room and we just talked about random things. Every so often I'd re-adjust myself without noticing it since it was a hot day (guys would understand why). I noticed he kept trying to ignore it but I didn't make a big deal out of it because anyone would be distracted by that. I asked him if something was wrong and he said no, but that it was weird that I'd have to re-adjust myself so often. I apologized and then we moved on from that topic.
I kept re-adjusting myself but I'd catch myself halfway through and then I'd stop. Brian said it was fine and if I had to then he wouldn't stop me since he didn't really care. I re-adjusted myself again shortly after but then I got a slight erection, probably because I kept touching it. Brian noticed and chuckled and said it was ok since it happened to him too sometimes. We kept talking but then I got really hard (still not sure why) so I said, 'Dammit, it won't go away' and he made a wise guy comment, saying jerking off would make it go away.
I was kinda intrigued but I brushed it off and said yeah right. He said no really, it helps, you should try it out if it really bothers you. I asked how could it help if nothing happens and then he understood that I've never masturbated before. He asked if I wanted to try it and I said I'm not sure but after a few minutes of persuasion I gave in. He told me to drop my shorts and boxers so I did. He got off the couch and sat on the bed with me after doing the same.
Now we were sitting next to each other with our shorts and boxers around our ankles and our erections very visible to each other. He was 5 inches hard and I was 4 inches hard and thinner than him (I'd like to say I'm a late bloomer but four years later and I'm only 4.5 inches hard...) but he didn't say anything. His pubic hair was really different from mine because it was long, straight and black, and was in concentrated areas while mine were short, curly and brown and were all over my crotch. Our balls were about the same though, barely bigger than a billiard ball. He told me to watch him so I did and he gripped his circumsized penis and stroked slowly. I did the same but I was nervous so he told me to relax and I'll learn to enjoy it soon enough.
After a minute he said we should try masturbating each other because it'd feel a lot better. I objected at first but again he persuaded me and I'm glad he did. I've never touched another penis before so this was pretty exhilarating for me. His penis was warm to the touch, and it was leaking tiny amounts of pre-cum. I felt his hand wrap against my penis and I felt this intense surge of pleasure. He stroked me maybe five more times before I said I was gonna pee but he said no, I was gonna orgasm. Then it hit me, this immense rush of pleasure racing through my body.
I felt my body lose control of itself and then I watched as spurt after spurt of semen flew out from me and covered my legs, shorts, boxers, feet, sandals and floor. It felt like I got hit by a bolt of lightning except it felt so good. He kept masturbating me the entire time and I watched as my semen just dribbled out all over his hand. To this day I'm still amazed at how much I ejaculated. I turned to him and said that was the best thing ever. He said yeah I know, I'm glad you enjoyed it. I realized he hadn't orgasmed so I masturbated him too and it took a few seconds before he orgasmed too. It felt like I went back in time because he completely covered the area in front of him with semen the way I did. I felt his penis like move as he ejaculated and his body kept convulsing the way mine did too.
After that we cleaned up the floor and our sandals and then we took a shower together where we masturbated once more. I usually felt ashamed about my penis size, especially during gym but he made me feel better saying that everyone is different and my penis size didn't matter because I had the biggest brain in our age group! It was a fun day and I'm sure glad my family was downstairs because I'm sure I would've been asked a lot of questions. My friend sure taught me a lot and I'm still putting that knowledge to use, usually with him when possible.