I am a sophomore in high school, and this happened a few weeks ago with my two best friends. This was our first masturbation experience together. None of us are gay, and we are much closer friends because of it, even though this was not my first experience.
First a little background: I am 16 years old as of a few months ago, and just finished my sophomore year of high school. I am around 5' 9' and 130 pounds or so, and I would describe my build as slim and athletic. I am a pretty good athlete and play basketball for my school team, so I work out quite a bit because of that. This was not my first masturbation experience with friends, but it was definitely one of the best.
And on to the story.
This year, I made two of the best friends I know I will ever have. We'll call them Nick and James. Things started out pretty coolly with Nick, we had a lot of the same interests and ended up at the same lunch table pretty much every day of the week, but never really talked a ton. Let me take a second to describe him: he's a little bit taller then me, and is a swimmer/diver, so he's in really good shape pretty much all year. I think most girls would describe him as cute; even though he's a few months older, he has this sort of boyish look to him.
James and Nick have been best friends for years. He is also an athlete and is incredibly fit, probably even more so then both of us! More importantly, both are really nice kids, even though at this point we weren't really that close.
Things started to change once we took a school trip together for a conference and the three of us roomed together. At the conference, Nick and I really hit it off. We had probably liked each other and thought we might become friends beforehand, but this is what really sealed the deal. We had a really great time together along with James, hanging out quite a bit, laughing hysterically, and getting some girls together too. This was also the first time I had seen both these guys naked to one degree or another. James had a six-pack going, with muscular legs and skinny arms, and was a pretty hairy guy even though he was kind of small. Nick had very little body hair and was pretty toned, but at this time, none of us were comfortable getting totally naked in front of one another.
When we got back to school, things really took off. The three of us started to hang out together all the time. I recruited Nick for a few activities I was involved in, he did likewise, and so did James. Things were great, and I was really excited to have two great new friends to add on to my already close-knit group. But I won't get in to the details; that's not why you're reading this!
Soon enough, summer came, By then, Nick, James and I were incredible friends, and everyone knew it. We spent a TON of time together, doing everything from working together, to studying, to doing after school activities, and just chilling out. When summer came we all had a chance to relax because all three of us are pretty serious students and we finally had a big load off of our chests.
One of those first days of summer when school was winding down, actually before finals were totally over, the three of us went to the pool. Eventually we got into the locker room which at this pool happened to be pretty nice with pretty much no one in sight. I guess by know we were all pretty comfortable with each other, and without thinking, I took off my shorts and started to turn on a shower to wash up. I was still standing there in boxers and a t-shirt when James followed my lead, but went a step farther. He took off everything except a pair of boxer-briefs he was wearing. I had seen some of his package earlier in the day through the outline of his bathing suit, and it looked huge! Now it really did! I'm not gay and neither are they, but for whatever reason, this was quite a turn on for me. I could tell Nick was checking him out too, we both seemed to keep staring at the bulge in his boxer-briefs. James seemed to like the attention, and before long, he made some comment about how his underwear was totally soaked and he needed to get out of them. By this time, Nick and I were standing in our own boxers and boxer-briefs sort of waiting for the showers to warm up, sort of waiting for something else to happen. Sure enough, James started to tug at the waist-band of the black underwear, and slowly lowered them to the floor. Nick and I were definitely watching.
What we saw did not disappoint! James is some percentage African-American, so his skin is rather dark, and he had a ton of dark black pubes starting a couple of inches below his stomach and continuing down towards his penis. His penis was long and thick, flaccid as it was probably about 4 inches, and the circumcised head was pointed and dark. His balls were somewhat small given the size of his penis, but hung pretty low, and also had some black hair. After what felt like twenty minutes, I'm sure it was closer to twenty seconds, he turned to go into the shower stall, and we caught a glimpse of his ass. It was pretty hairy and skinny, really no fat at all, and seemed to work with his body well.
At that point, Nick and I kind of just looked at each other. Again, we aren't gay. All of us had had plenty of girlfriends, made out with plenty of girls, and done some beyond that, and a lot of it had been in each other's presence! But something about what James had done got us both interested, and we both seemed to know it and not deny it.
But then, an employee of the pool walked in just as James stepped into his shower, and Nick stepped into his without taking anything off. Nothing else happened that day, and we headed out to meet up with some girls a bit later.
A few nights later, the three of us were over at my house hanging out with a few girls we were friendly with. I think we all had the same idea in mind: to try and get some action that night from the girls. But for whatever reason, it never really happened. The girls left around 11:30, and curfew was 12. James's mom said she couldn't pick him up until late, and my parents were out with our only car at the time because the other was in the shop, so I offered for both of them to sleep over. After my parents got home and went to bed, we headed down to the basement. I was still pretty horny and had a serious case of blue balls, and was looking to relieve some of the tension. Nick made the in. He flipped to a porn channel, and announced that he was really horny and needed to do something about it. James and I locked eyes and nodded in agreement. I then suggested we compare penis size, to satisfy my curiosity. All agreed, and I grabbed a ruler.
We had already seen James' penis, so he decided to go first. Now, though, he had a huge boner, and the veins were quite prominent on the side of his penis. His balls seemed to hang especially low, but would tighten as he gave his penis a light tug, and the head seemed to turn a dark shade of purple in anticipation. It was also a bit shiny from what seemed like a dab of pre-cum already dripping from the opening. He held the ruler out and announced 8 inches. Not believing it, I walked over and sort of subconsciously put my hand on the ruler and his penis to double check. I didn't even notice, but his penis seemed to love my hand on it and kind of jumped with delight. I finally measured him out at 7 inches.
I agreed to go next, and lowered my boxers and out popped my 6.5 inch penis. Jokingly, I also announced 8 inches, and now it was James' turn to double check me. I was also really hard, but for some reason I tend not to have pre-cum, so none was there at the time, but I definitely felt the build up as James put his hand on me.
Finally, it was Nick's turn to measure. He seemed to hesitate at first, but James and I egged him on, saying it was nothing to worry about and he had already seen ours. He then lowered his boxer-briefs slowly. He had what I would describe as a perfect penis. His pubes were dark but neat, he later told us he trimmed and shaved on occasion, and his legs seemed to work perfectly up to his groin area. His penis was not too big but not too small, was a pretty dark color compared to the rest of his skin, and pointed probably about 45 degrees in the air with his boner. The head had already started to turn a darker color, and was pretty skinny and pointed, kind of like mine and James'. His balls were tightly clenched towards his body, but were pretty big and hairless, and a darker color as well. His head, too, dripped with some pre-cum that must have been building. He, too, started to measure up, and almost seemed to want us to touch him when he joked '8 inches.' We didn't hesitate, and soon enough, three hands were on his penis, finally measuring out at around 6.5 as well.
With that said and done, I suggested we play a game of truth or dare for something else to do. Given that we already knew pretty much all there is to know about each other, Nick suggested we change it to a game of dare. We agreed, and I went first.
Nick dared me to jack him off for thirty seconds, which I did. Things continued like that for a little while, but eventually, without so much as announcing it out loud, we ended up in a circle jerk. I was jacking Nick, Nick jacking James, and James working on me as we watched the soft core porn and each other. I must have been doing a pretty good job, because Nick was moaning and squirming. I was rubbing his head in circles, aided by his now prominent pre-cum, and occasionally giving his shaft a long, firm stroke. I was also playing with his balls, which he told me he really enjoyed. Before long, I felt his penis tense in my hand, and he sort of tilted his head back with pleasure. His balls seemed to pull in even closer to his body, and his hips started to move up and down. Just then, he shot a few ropes of cum up into the air in what I would say was a pretty far shot. This seemed to send James over the edge, and I followed shortly.
We all just sort of sat there enjoying the pleasure for a few minutes, and eventually, I noticed our penises started to go flaccid again. We stopped for a while and talked, mainly about masturbation, how long we'd been doing it, techniques, and so forth. We finished the night out at about 4 in the morning with another circle jerk, this one a bit slower and considerably more tired then the last, but incredible nonetheless.
Since that night, we've had a few more experiences like this, some going farther than others, and have generally grown totally comfortable around each other's naked bodies and such.
The experience has made us even closer friends, if that's at all possible, and we are now totally inseparable. There was nothing awkward about it, nothing to be ashamed of, and no guilt. We talked about it the day after, and all agreed we aren't gay, we just enjoy masturbating with each other.
I would encourage anyone looking to become closer with anyone else to try an experience like this. Just make sure you're both (or all three of you) are comfortable with what you're doing, and nothing will go wrong. Indeed, it will be a ton of fun, totally worthwhile, and make you even closer friends!