This was four years ago when I was 14
I was best friends with this girl Sarah in eighth grade. One time my parents went out of town so I slept over her house. We hung out before bed playing games, watching tv and typical sleepover stuff. She had a younger brother Nate who was 13 and we hung out with him too. When it was time for bed I slept in mates room. We had sleeping bags on the floor and we played ps2 for a while until his parents told us to turn it off and to go to sleep. We weren't tired so we laid there talking. We started off talking about video games but then we talked about school and eventually girls. I knew he thought that mine and sarah's friend Ashley was cute so I started asking him about her. He said he thought she was really hot and he started blushing. I looked down and in the moonlight I could see his boner poking up in his sleeping bag. 'you need to take care of that thing?' I said with a smile. He looked down and blushed even more. 'Its fine. You don't need to be embarrassed. Everyone gets boners and everyone jacks off.'
He said, 'well, not everyone...'. I was shocked! 'what?? Why don't you??'. He replied with, 'well, um, I don't really, uh, know how...' I was even more shocked. 'wow. I can't believe you don't know how to masturbate'. He started frowning, 'I know. I'm a loser'. Now I felt bad. 'oh no, you shouldn't be embarrassed. You're not a loser', I wanted to cheer him up, 'how bout this. You want me to show you how?' he stared at me for about a minute. 'umm isn't that gay?' he said. 'it's only gay if you're gay. It's just a guy helping out another guy'. I could tell he wasnt totally on board so I just hopped out of my sleeping bag and pulled my pjs down as my 3 inch soft dick flopped out. Nate just stared as my dick grew semi-hard. I started slowing jacking off letting Nate watch. 'so you just make a circle with your hand around your penis and you rub up and down. See now I'm getting hard. After a while I'll cum. That's when white stuff comes out of my dick. It's feels really great.' he just stared and kind of turned as I knew his dick was getting uncomfortable. 'well?' I said. 'well what?'. 'aren't you gonna get your cock out and try this? I don't wanna be the only one naked here.' Nate had blonde hair and was short and slender. He kinda hesitated and fiddled around with his waistband. 'oh c'mon. Get your pants off!' I reached over and grabbed his pants and pulled them down. His 5 and a half inch rock hard dick sprang out. I told him to do what I was doing. He grabbed his dick and tried jacking off like me but wasn't doing it right. 'your not doing completely right, her like this'. I reached over and grabbed his penis. I started jacking him off and at first he looked shocked but I knew he liked it as I kept going. 'and with your other hand you can hold your balls'. I grabbed his balls with my other hand and slowly caressed them. 'wow. You're really good at this!'. Nate said. 'yeah so you think you can do this?'. He said yeah and as I was about to let go of mates penis he grabbed hold of my dick and started jacking. 'woah. Okay, I meant on you. But actually that feels great. Don't forget about the balls'. He grabbed my balls as he jacked my cock. I kept jacking him and he shivered as a little cum dribbled out of his cock. 'see look you came! Now keep doing me and I'll show you what it'll look like when you cum when you're a little older'. He kept going and soon enough I came and it shot all over the place. Some got on nates stomach. 'wow that was so cool!' ' yeah thank you for that. I think it was the best orgasm I've ever had!' we cleaned up and went to sleep. The next day I was out in their yard with Sarah and she asked what we did last night. I said we played video games. 'yeah but I heard you shut it off and I heard noises for like 30 minutes after'. 'well, okay you really wanna know what we were doing?'. 'uh yeah'. 'okay. I taught your brother how to jack off'. 'what?!?? Ewwww. Really?'. 'yeah, why? Guys do that together'. 'what exactly do you do?'. Now I new Sarah didn't know alot about sex and stuff but she didn't know about jacking off? 'well, it's kinda hard to explain. I guess I could show you too'. She looked shocked but agreed to it. We went and sat at this bench on the edge of their yard. I pulled my pants down and sat next to Sarah. She looked shocked. I started jacking and told her what I had told Nate. 'can I do it for you?'. 'wow. Eager? I'll let you if you let me rub your pussy'. 'umm? Well sure'. I stuck my hand down the front of her pants and started rubbing her smooth pussy. She grabbed my cock and started jacking. She loved how warm it was. I told her to lean down in front of my cock. She did and I came right in her face. She said it felt good. I rubbed her until she orgasmed. We did other stuff but that's not for this site.