A continuation of my true experiences as a teen.
I briefly mentioned my best friend Matt and his older brother John in my last story. This involves Matt and our experiences so I will give a background leading up to our first mutual.
I met Matt and his family before I can remember, I was four at the time. According to our parents we bonded the first day and we've been best friends ever since. Likewise with my brother Dave and John. Matt and I were 'attached at the hip' and I've always felt closer to him than my own brother.
I still remember the first time I saw him naked, we bathed together. I seem to remember him sleeping over for some reason and my Mom tossed us into the tub together. At that age I'd only seen a few naked guys outside of my family and noticed his penis was different from mine, but like my Dads. The end was covered up with skin. It intrigued me and made me think that some people had it and some didn't for whatever reason but it wasn't a birth defect or accident, it's just how some people were. Kind of wished I looked that way and wondered if I'd ever grow to be that way.
Matts Dad was a Contractor and had a really nice custom house, including an in ground pool, so I assumed they were wealthy. No one else I knew had one. I can't remember when it started since it seems we always did but we normally skinnydipped when it was just us brothers. I never felt shy around Matts parents and was never bothered being naked around them. My parents taught Dave and I nudity was no big deal and not to be ashamed of our bodies and Matts were the same. What I'm trying to explain is we were very open with each other with no 'hangups'.
Now the story takes up where I left off........
After I asked Matt if he learned anything the previous night and I got my answer with a blush we whispered to each other how awesome it was and how stupid we were for not figuring it out for ourselves. Like Dave and I, it became a nightly routine for Matt and John but the topic rarely came up other than speculating if other friends of ours did it. Primarily Mike and Scott who were two of our closest friends but Mike was an only child and Scott had two sisters so we wondered if they figured it out for themselves or just didn't know what they were missing out on. We talked about discussing it with them but never did. Don't know why now, I cant remember.
The first time Matt and I did anything together was when we were finishing eighth grade. We'd gotten home from and end of the year school dance and I was sleeping over at Matts and John was at my house with Dave. We were showered and in bed (I'd use Johns when I slept over) and were talking about the dance, the people there, our dates and how we had expected a little action, and poor Mike who'd had an obvious boner most of the night tenting his slacks. Talk stayed on sex and we speculated on when we'd finally get some 'tail' and how good it must feel compared to jacking off. We were both just laying on top of the beds in our briefs and the talk had us both tented, occasionally readjusting ourselves.
I started to think if I was at home with Dave I'd whip it out and go for it but wasn't sure how Matt would take it. But I could sense that he was in the same predicament and thinking the same thing. I mentioned I really needed to 'take care of this' pointing at my hardon and said it looked like he needed the same relief. Matt said 'Me too' and there was an awkward silence as we waited for the other to speak.
He then said 'You do it with Dave don't you?'. I told him pretty much every night. He said him and John too. More silence. 'You want to do it now?' we both asked at almost the same time and laughed. Ice broken we pulled off our briefs and started tugging ourselves, watching each other.
I mentioned earlier he wasn't circumcised and it'd always intrigued me. I'd seen him both soft and erect and was some how turned on by how the skin slid up and over his glans, exposing his head and covering it with each stroke. I figured it felt better than the same dry hand I was using, tugging at what skin I had left to reduce the friction.
We were openly watching each other intently and sometimes meeting each others eyes, shy in a way but ok overall. It didn't take long and I came first all over my chest and stomach with several spurts. Matt stopped and watched. When I was done he really went at it, his hand a blur, and when he started to cum just used his index finger to rub the underside of his glans with the tight skin covering the head.
He didn't squirt like me, it shot a bit but came back straight down on his hand in big globs which he rubbed over his dick as he continued to stroke until he was done. I had never rubbed my own cum on my cock and I thought I'd have to remember to try it sometime.
We relaxed and didn't talk for a bit. Using our underwear to clean up and even though I wasn't at home I threw it in with his pile of dirty clothes. We had a nervous laugh with each other saying that's just what we needed but swore not to mention it to our brothers that we did it together. We both went to the bathroom to wash off and I again marveled at how Matt pulled his foreskin back to clean the rest of the cum off, his cockhead red and almost looking raw but he didn't flinch as he cleaned himself.
Back in bed, exhausted and relaxed, Matt asked if it was ok if we ever did that again and I said 'HELL YES!' I confessed I wished we'd done it before since we were closer than we were to our brothers and we did it with them anyway so I didn't think it that much of a big deal. End of the conversation for the night, lights out and we fell asleep.
This first experience with Matt made us closer than I could ever imagine. Awkward, yes. I probably didn't describe it well enough. But like my brother and I, jacking off before falling asleep became common for us when I slept over or Matt slept at my house.