A true story of my first time masturbating with other guys. And I'll never know for sure but I think it was Brad's first orgasm.
This happened at a sleepover at my friend Tom's house after his 14th birthday party. Tom wasn't in my regular group of friends. I knew him through our parents and didn't see him often but we were close, like cousins I guess. I also knew the other guys, Kenny and Brad, through Tom. They were his neighborhood friends and when I was over at Tom's would often end up hanging with them.
The four of us had planned on staying up all night but by 1am were getting sleepy. We were sitting in a circle in our briefs talking about stuff I can't remember when Kenny gets up saying he has one more present for Tom. He went to his duffel bag and pulls out four porn magazines, dropping them in the center of our circle. He tells Tom he can pick one to keep but has to take the rest home to his brother, but we can all look at them.
I'd seen tame magazines in the past but these were the first hard core porn magazines I'd ever seen and just the picture on the cover gave me an instant erection. Looking at them we didn't talk much other than comments about the women and the size of their tits or how hot their pussies looked. Glancing around from time to time I noticed we were all tenting our briefs and I wasn't the only one sneaking peeks, we all were.
Somewhere along the line Kenny wondered out loud if our dicks would end up as big as the guys in the pictures. Brad said his already was but Tom pointed at his briefs and said there was no way that was anywhere close to adult size. Brad persisted and said he just wasn't all the way hard, it only got real big when he played with it. Kenny called his bluff and told him to prove it, saying his bulge looked smaller than the rest of ours, which was true. Brad got a bit red in the face and said he wouldn't take his out unless the rest of us did too.
I hadn't said a thing the entire time but was kind of hoping things would end up like this. I was curious what they looked like compared to mine and my other friends. We'd checked out each others dicks from time to time to see how we measured up to each other. I said I would as long as everyone else did and stood, hooking my thumbs in my briefs, waiting to see if they were going to follow my lead. Kenny stood next, Tom and Brad following. Kenny said to be fair we all had to strip at the same time, on the count of three, which we all did.
In a way I was surprised. Although Brad was the largest of us and his voice had changed he had the smallest dick, smallest balls and hardly any hair. Kenny was the winner in size and had hair but it wasn't really a bush yet. Tom was the smallest of us in stature and looked like a preteen but had a full bush of blonde pubes. I also had a full growth of hair over my dick and out of the four of us I was the only one with a little hair in my armpits.
You could tell Brad was a little embarrassed at his size and he tugged his dick trying to make it longer. Tom told him that wouldn't work and he'd get bigger as he grew up. Kenny asked if he could even shoot yet to which Brad said he didn't do things like that, turning red in the face. Kenny said bullshit, we all do it, and I want to right now. And right there he starts stroking himself.
The three of us were stunned, probably with our mouths hanging open and eyes bugging out of our heads. But we all slowly joined in, standing in a circle watching each other. Brad didn't seem to know what he was doing and his whole hand covered his penis and he seemed to be pulling on it instead of stroking. Tom and I looked at each other with questioning eyes like "what the hell is he doing?". Kenny too was watching him and said "you're doing it wrong" and pushed his hand away and started stroking him using just his thumb and two fingers.
Brad at first was shocked and tensed up but after a few minutes relaxed and tentatively reached over to touch Kenny, not stroking him, just feeling him up. Brad said he needed to lay down so Kenny let him go and they went over to Tom's bed and Kenny started up again. Tom and I had been watching while slowly stroking ourselves and we had moved over to the bed next to each other to watch.
I still don't know why I did it but while looking down at myself and Tom right next to me I wondered how his pubes felt. His hair looked so golden and soft I just needed to run my fingers through it. I took my free hand and put it on the front of Tom's thigh to see his reaction. He didn't flinch and looked at me with a little smile on his face, stopped his stroking and turned toward me.
I stopped my stroking too, faced him, and ran both of my hands over his chest and stomach lightly, trying to get up the courage to go lower. I probably wouldn't have continued but Tom started doing the same to me, being a little more forward than myself, lightly pinching my nipples and feeling the hair in my armpits. I was hornier than hell by now and went for it and I wasn't disappointed. His pubes were really soft compared to mine. Tom did the same and ran his fingers through my bush. I felt his sack and balls, rolling them in my fingers and he did the same. I saw a big drop of precum ooze from the tip of his cock and used my index finger to smear it around his glans which made Tom gasp. He grabbed my dick and started jerking me off so I did the same to him. It felt soooooo much better than doing it to myself. It was hard to do this standing but his penis felt a lot like mine and we were the same size though his looked bigger on his smaller body.
We had forgotten about Brad but stopped our fun when he started moaning and told Kenny to stop because something was happening. Kenny sped up his stroking until it was a blur and Brad's eyes got real big and his mouth made a big "O" of surprise and he shot all over his chest and stomach, his body convulsing with each shot. Brad let out a big breath when he was done with his orgasm, a look of bliss on his face. Kenny spit in his hand and really went to town on himself and shot his load in about a minute.
Tom and I looked at what was all over them. Brad's was mostly clear with some white streaks in it while Kenny's was milky white and thick. While they lay there Tom and I began stroking again to get off. Kenny was watching us both while playing with his now half soft dick, Brad had his eyes closed and was completely limp, running a finger through the cum on his stomach. I wanted to play with Tom's dick again but didn't, I was too close to cumming and wanted to finish. I think Tom was in the same boat. We locked eyes several times and I got the feeling he wanted to do me too.
Kenny stunned us by saying he wanted us to shoot on him. Tom and I looked at each other like "what the HELL?!?!" but didn't care, we were too close and I figured I'd shoot in my hand or on the floor anyway and even though it seemed kind of gross I did it anyway, unloading on his stomach and Tom on his chest.
It was a contrast seeing our different cum. Mine more yellow and thick than Tom's. Tom's white but runny. Kenny's very white and thick like mine. Kenny asked for his briefs and he wiped the mess off his chest and stomach and cleaned up Brad too. Not much was said and I think we all were having second thoughts about what we just did. Brad had dozed off and Tom was a little pissed at having to sleep on the floor, it was his room after all.
As we were laying in the dark trying to fall asleep I was confused but did know I enjoyed what we did and overall wanted to do it again. Maybe with my buddies. But how to start it? I wasn't that bold, not like Kenny.
The next day when we got up all was normal. It was like it never happened. Brad and Kenny went home and my parents picked me up around mid morning. Tom said "See you around" just like always. We never mentioned what we did again. I always wondered if Tom and his buddies messed around after that night but I'll never know. I do know it helped me initiate messing around with my buddies.