Just thinking about writing out this story has gotten me very horny, and I am sitting here naked and nervous while I'm typing.
To start out, I am and have always been a tomboy. All that girly-girl stuff never appealed to me. I would much rather be seen in jeans and a t-shirt than a dress and heels, and for as long as I can remember the majority of my friends have always been boys.
Back when I was about 14, my parents were at work, a couple of friends were over at my house (again, both boys), and we were out in our pool. We swam for a good two to three hours before one of them had to go home because he had some chores to do. The one who stayed behind was pretty much my best friend and had been for a few years. We kept swimming and started horsing around, wrestling and dunking each other under the water. After this went on for a while, I swam under him and tried to pull him under, but when I grabbed him, I felt something hard in his trunks. At this age, living in a rural area and having no internet, I knew very little about sex so we sat down in the shallow end and I asked him about it. He got embarrassed and said it happened a lot. Since we were open with each other, he told me about how often it happens, that he started masturbating, that he was starting to see girls differently, and that playing around with me got him excited. I asked him if I could see it, and after a few seconds he stood up and pulled off his trunks. Since it was my first time every seeing a boys penis I thought it was huge, but I now know at that point it was probably only four to five inches and fairly thin.
He then asked me about my masturbation, and I told him I didn't know what he meant. I had never masturbated before, but I did notice that drying off after a shower felt really nice, and that sometimes I had a little bit of dampness in my underwear. Talking about this made me feel flushed and my nipples were poking out through my bikini top. He then asked me if he could see my breasts (which were only about a B-cup), so I undid my top and showed him what I had. After a couple of minutes of us just staring at each other, he then asked me about my bottoms. I wasn't sure, but since he was naked it was only fair, so I slipped out of my shorts and stood there naked to the world.
Again, we just stood there for a little while just looking at each other, but then I asked him if he could show me how he masturbated. His hand went to his penis and started moving up and down on it. I asked him how it felt and he said it was really good, and then I asked if I could try it. He sat back down next to me and I grabbed his penis, moving my hand back and forth on it. This probably went on for less than 15 second before he grunted, lifted his butt off the steps and had an orgasm. I saw some white stuff floating around, and he said that's what happens when he masturbates, then scooped it up and tossed it out. He then said that he wanted to do it to me, so he spread apart my legs and started rubbing my vagina. It was awkward because he had never done it before, but it felt really nice. He kept rubbing the outside which was nice, but when he stuck the tip of his finger in, I gasped and laid my head back on the concrete. It was just the tip, but my vagina felt full from it. This didn't last long, and I told him I started to feel something weird but he kept going. Suddenly it hit me, I let out a high pitched squeal, my legs kicked and my toes spread as I had my first orgasm. I grabbed him and held on as the sensations went through my entire body. I thanked him for it, and after a little while we got out and went downstairs to my room in our towels. We flung off our sandals and sat on my bed naked and I said I wanted to watch him masturbate again, and he said he wanted to watch me too. We both played with ourselves two more times before we got dressed and went back upstairs before my parents got home.
The rest of that summer I masturbated constantly, both by myself and with him. We never had sex, not just because I didn't want to lose my virginity yet (and still haven't), but also because I didn't want to ruin the friendship we had. So just about any chance we had, we would both get naked in one of our houses or my pool and would have wonderful teenage orgasms. This went on for a quite some time until he found a girlfriend in our junior year, and he had to stop because he thought it would be wrong. I understood and we still stayed very close until we went to different colleges and mostly lost touch, outside of emails every now and then. From that point on I went solo and masturbated thousands of times, naked and alone but completely satisfied.
Now if you'll excuse me, I need to crawl into bed and rub myself to at least one orgasm. Happy masturbating!