Sleepovers almost always caused some kind of horseplay
I noticed on here that a lot of guys weren't successful the first time they tried to jack off. I was pretty lucky and the first time I tried it, it worked and I had an awesome orgasm. No cum, but definitely the real deal.
I started seventh grade in a new school in a new town. I was a small skinny kid. Just turned 13. Up to then I was pretty sheltered and didn't know anything about sex at all, including masturbation. I had seen other boys my age naked and had also seen older boys, so I knew that boys' bodies changed as they got older. This one boy that I was friends with from my old school slept over once and we showed each other our boners and he showed me his peachfuzz. His dick was about an inch longer than mine and thicker.
At my new school, I made friends with a couple boys in my class and Brad, a boy from 8th. We hung out together at lunch and recess out on the edge of the playground, away from the other kids and talked about girls and sex. Right around this same time, I had a couple dreams where I was flying and then I would feel this weird tickling in my groin and it would feel like my dick was wiggling by itself. It would make me wake up and I tried to go back to sleep because the feeling was so good.
I learned a lot from those guys-like everybody gets morning boners. I also got an idea from watching their gestures about how beating off was actually done. It got talked about a lot for a couple days and the eighth grade boy admitted that he had tried it in the shower and white stuff had come out of his dick. Later on he showed us his dick and some of his pubes in the boys' bathroom.
That's what made me try it myself, so one night after my bath, I sat on the edge of the bathtub and played with my penis until it got hard. Then I used two fingers to stroke my stiff, skinny shaft. After a while it started tingling down there and then my orgasm hit. My legs moved involuntarily and my dick had that wiggly feeling like I got from my dream. I didn't shoot anything and it was almost a year before I could actually shoot sperm. Even so, I started jacking off just about every time I took a bath.
A couple weeks later, one of the guys got to have a sleepover and he picked us three to do it. He had a pool with a poolhouse where we were set up with sleeping bags and videos, etc. We stayed up late watching Star Trek and messing around. When we all got in our sleeping bags and the lights were off, the eighth grader said he needed to jack off. We all agreed to keep this a total secret, then we made sure the door was locked and turned on a small light.
Brad was sitting on top of his sleeping bag in white briefs. Everybody took off their underwear at once and looked around at each other. Me and one other boy were about the same size and hairless. The other boy was slightly bigger with a very small bush. Everybody was circumcised. Brad was biggest and had the most pubes and also some leg hair and armpits. His boner was much thicker and curved up toward his stomach. He started jacking first. My boner was so stiff. We all started stroking. It was going to be me and Eric's first time seeing cum. Turned out Jeff had already jacked before with Brad and had seen him shoot.
Then Brad told us about a game he played at camp where they rolled dice and had to give each others' dicks the number of strokes that the dice said. Again everybody had to swear to never tell anyone-ha ha, except you guys. Brad started the game and had to give Eric seven strokes. We all took turns and it ended up that we all touched each other at least once. I liked feeling the stiffness of the other boys' dicks. When Brad stroked me he also played with my tight little nutsack.
Brad said, let's all just beat off, so we layed on our sleeping bags and started going for it. It got quiet except for the sound of our hands on our skin and boys' heavy breathing. Me and Eric orgasmed first. Then Brad said he was ready and so we watched him shoot his jizz all over his stomach. He grabbed a sock and wiped it up. Jeff shot a tiny amount of sperm.
Brad lived close to me so after that night, we would bike to each others' houses for after school j/o sessions when our moms weren't at home. Also Eric's family once took me along on a houseboat trip and he and I had some adventures on jet skis and jacking off outdoors.