This is a continuation of my first post, "Big Brother Teaches Me" from Oct 24.
It's a true story about how I taught my best friend Dan to jack off.
Dan's family moved into the house two doors over from mine when we were six or seven. We became instant best friends. It was like we'd always been that way even though we just met. Dan was an only child and was adopted, his mother being unable to have kids. I have two brothers, Lee and John. Lee two years older than me and John two years younger. I have shared a room with Lee as long as I can remember and it was Lee that showed me how to masturbate.
Dan became like another brother to us and was over at our house all the time and likewise for me at Dan's. At our first sleepover at my house when it came time to shower before bed I told Dan my brothers and I all went in the bathroom at the same time to make it faster and he could join us or we'd wait until he was done. He seemed a bit stunned and asked if we were all naked around each other. We told him it was no big deal to us, we all had "wieners". He said he'd never been around other naked boys and said he'd join us. He seemed to really like it, openly staring at us and himself comparing, and not shy in the least.
When I'd sleep over at Dan's, we'd do the same thing at bedtime and share the bathroom. We didn't do anything considered sexual. Just the normal comparing size and while we never touched each other with our hands, I vaguely remember one time when we both got erect we had a "sword fight" with each other. Swaying our hips back and forth, hitting our penises together.
I entered puberty first and Dan was amazed at my hair coming in. He would get on his knees and stare at it and then have me do the same to see if he had any coming in. He started getting hair several months later and confessed to me one day that he'd had his first wet dream and had I had any yet. I told him I did quite a while back and found this as the opening to teach him how to masturbate.
I explained how to rub yourself, demonstrating on my left index finger. And telling him to use something to lubricate himself or use soap in the shower. I also told him not to worry about feeling like he had to piss, to just keep going and see what happened. He wouldn't be sorry and would have the best feeling ever.
I just assumed he'd do it and don't remember bringing the topic up again, until one night sleeping over at his house. We were sitting on the floor in just our briefs playing Battleship and listening to the radio when Dan said "Crap, it's hard again. It's been doing that all day." Sure enough, I could see the tent in his briefs. I figured since he probably jacked off alone, he would like some privacy so I told him I'd go downstairs for a while so he could take care of himself. I was stunned when he said he wished he could but it didn't work for him yet. Not knowing exactly what he meant I asked him to explain and he said he did everything I told him and though it felt good, nothing ever happened. I again demonstrated on my finger and he said that's the way he did it, but nothing ever came out. I asked Dan if he wanted to show me how he did it in case he got something wrong. He hesitated and said only if I didn't tell anyone and I showed him how I did it. I figured since I did it with my brother all the time and Dan was closer to me than Lee it would be ok.
I told Dan to get some lotion and he got some baby oil and we moved to his bed, stripping off our briefs. The talk and expectation of jacking off made me hard and we lay down next to each other. We both oiled up and Dan jacked just like I did. After just a few minutes he stopped and said "See, nothing." I told him he just wasn't doing it long enough and to watch me to see how long it took.
I lay back with Dan watching me propped up on his elbow and went to town. I was a bit self conscious with him staring at me and I didn't say a word and hurried to finish, squirting straight up and arching down onto my stomach. Dan said "WOW!" and ran his finger through the puddle of sperm on my stomach. I told Dan it was his turn as I wiped myself off and he started again.
I urged him to keep going and his body would take over on it's own. He started speeding up and breathing heavier. He lay his free arm over his eyes and started to make little whimpering sounds, almost like he was in pain. His face kind of grimaced under his arm and I was starting to get worried, maybe something was wrong. His body suddenly stiffened and he blasted all over the place, blobs of cum all over his chest and belly. A lot more than my first time.
Once he climaxed, the grimace was replaced with a look of bliss. Dan looked at me, smiling. I asked how he liked it? He said "That's the best FUCKING feeling EVER!" It was the first time I'd ever heard him say the "F" word and laughed. I wiped him down and we ended up sleeping naked that night. The next morning we jacked off again, at the same time, while watching each other. I thought it was pretty cool and glad I showed him how to do it.
Strangely enough, it was years before we had another mutual. When I'd sleep over, we'd take turns in the shower. At my house, we just didn't do it. We compared our changing, maturing bodies often and wondered at how some of our friends were progressing and if they jacked off too. My next story will be about my second mutual with Dan where we finally got each other off.