I just submitted a story about masturbating with a friend of mine when we were in grad school. This is a story of an experience I had about 10 years earlier, which is one of the stranger ones I've had.
My family had taken a trip to Florida when I was 13. We were staying in a motel on the beach, and I met a couple of kids my age. One of them was named Mark, and we pretty much palled around for the four or five days we were there together. One evening, these two older (16- or 17-year-old) girls from the motel were at the pool about the same time we were, and Mark started talking to them.
They were both pretty and Mark was doing his best to flirt with them (if a 13-year-old could flirt). I was pretty shy around women at that age, so I kind of hung back. Pretty soon, we started horsing around, and one of the girls flashed us. I was totally stunned, but Mark took it in stride and dove under the water and yanked down her bikini bottoms. I'd gotten an eyeful of a pair of great breasts and a cute butt, and I was pretty overwhelmed by the whole scene, which had taken all of 30 seconds or so. I was also terribly hard under my trunks. The girls, I guess, decided that things had gone far enough and that enough teasing had been done. They quickly took off. Mark and I hung around for a few more minutes and then he said he had to go because his family was going to the movies.
The next day, Mark and I were hanging out after we'd finished dinner with our families. We saw one of the girls from the day before with some guy about her age. Sometime after they'd left the pool, Mark and I went down to the beach. The girl and the guy were on a bench under one of these little thatch shelters, making out. Mark said we should sneak up and watch them, and we skulked over behind the bushes to see what we could see.
They were making out and he had his hands under her shirt, but we really couldn't see much. We watched for a few minutes and although the action hadn't changed, I was getting excited. Then Mark started tugging my arm and said, 'Let's go.' I didn't really have a desire to leave just yet, hoping we might 'really' see something, but it was now dark and we couldn't see anything at all, so I followed him.
Mark went down the beach a ways to a small hollow behind a dune and flopped down on his back. I lay down next to him and he flat out asked me if I wanted to jack off! I was horny from watching the girl making out, but I hadn't thought at all about jacking off with Mark (I guess I was a little naïve at that age). I quickly realized it was a great opportunity and I said, 'Yes.' Mark practically ripped off his shirt and shorts and told me to get naked. I was kind of scared about being nude out on the beach (with another boy, no less), but I wanted to fool around so I stripped, too. We lay on our sides facing each other, and Mark said he'd do me if I'd do him. I, of course, agreed.
Mark then reached over and took my very hard penis in his hand and began to stroke me. I reached for him and, at his instruction, held his scrotum in one hand and pumped his penis with the other. Meanwhile, he alternately pumped and caressed my penis with one hand, while rubbing my stomach and butt with the other. We didn't have any lube and the positioning was clumsy. We kept bumping our arms into each other and having to shift position a bit. Despite my arousal, it took a long time (it seemed to me at least) before I started getting excited, if you know what I mean.
As we masturbated each other, I actually got kind of frustrated with Mark, who would start doing something to me that felt good, then change and do something else. I couldn't tell how well Mark was liking what I was doing, but I just did my best to steadily stroke him the way I liked to get done.
So we stroked each other for maybe ten minutes. Then, just when I was starting to get into it (and getting to where I knew I could have an orgasm if he kept doing what he was doing to me), Mark stopped stroking me and pressed up against me. He put his arms around me and grabbed my butt and started thrusting into my hand.
I really didn't know what to do, so I stopped stroking him. He told me to keep going and soon after that he put one of his hands between us and took hold of my penis again. He put it next to his and started working his hand on both of them as he continued to thrust. This seemed to me as awkward as before, but then either he or I had gotten excited enough that we started getting a little wet, and our penises began to get slippery.
Mark said, 'Spit in your hand,' and he reached up and spat into his hand. He put it back on us and it got even slicker. I did the same. Now we were both slicked up and it definitely felt good. I started humping my hips, too. We were lying on our sides with one hand each holding us together. We slid back and forth against each other, our free arms holding each other's butts.
Neither of us lasted long. Within maybe a minute, I started to orgasm while Mark kept humping against me and stroking us, which was almost unbearably pleasurable for me. Then suddenly, Mark said he was going to cum. As he started to orgasm, though, he pulled away from me and rolled onto his back and frantically pumped himself as he ejaculated. I was still right in the middle of my orgasm and was suddenly left frustrated again. Now I was on my back, too, frantically finishing by myself what had been one of the most intense orgasms I'd ever had. I tried to keep my orgasm going, but it quickly diminished as I watched Mark jerking his hips as he came. We both worked on ourselves until we'd gotten all we could from our orgasms, and then we just lay there, spent, for a couple of minutes until Mark suddenly sat up and said, 'Let's go' and started to get dressed. Neither one of us said much on the way back to the motel. Mark just said, 'See ya' before going into his room.
I'd certainly enjoyed our jack-off session, but I felt pretty weird about the whole thing. The next day, Mark was nowhere to be found and I never saw him again.