My first experience with masturbation was when I was eleven. My cousin and I were spending the afternoon together while our moms shopped. Tom was fourteen and pretty geeky, but my mom wouldn't let me stay home alone and I didn't want to go shopping with her and my aunt, so I had no choice. We were at my Aunt's house and it was a rainy, disgusting day with nothing to do. I knew I was going to be bored. Tom and I got along OK, but really didn't have much in common.
I spent about an hour just watching crap on TV, and Tom was up in his room doing god-knows-what. Finally he came down and sat on the couch and started watching TV with me. He seemed kinda nervous and I didn't know what was wrong with him, so I asked him what was up. He said nothing, mind your own business, so I did. After another half an hour of mindless TV I told him I was bored and wanted to do something else. We decided board games were no fun, and we couldn't go outside. He said let's go up to his room, so I followed him up the stairs.
He turned on the stereo and sat on his bed. I started looking through his tapes. Out of nowhere he said he had some cool magazines I could look at, but I couldn't tell anyone about them because they were secret. I didn't know what he was talking about at all, but I was curious so I said OK. He stuck his hand under the bed and pulled out about five dirty magazines. At first I was shocked, but I was more curious about what was in them than anything.
I asked him where he got them, but he wouldn't tell me. I later found out he got them from a friend. He handed me one and asked if I had ever seen anything like it. I said no and opened it up. I forget what the title was, but it was real hardcore that showed everything. I flipped through it and saw women doing everything imaginable with men, and there were parts devoted to guys and girls masturbating.
He asked me if I liked them. I wanted to seem cool so I said yeah, but I was kinda weirded out. Then he asked if I ever saw a naked guy before and I said no, only in pictures. He said he would take off his clothes if I would. (Classic 'I'll show you mine if you show my yours...') I was very shy about my body at that age because I was just beginning to develop, so I said no way, that would be gross. He kept asking, saying it would be cool and everyone his age does it, and I was really curious because of the pictures and everything so I finally said OK.
Before I even knew what was happening, he had his shirt and pants off and was standing next to the bed in just his underwear. I couldn't help looking at his crotch, and I could easily see his penis through his white briefs. He was smiling and told me it's no big deal, and it was my turn. I was really nervous but took off my t-shirt and held my arms over my chest. I wore a bra but hardly had any boobs at that age. He told me how cool I was doing this, which I thought was great, so I stood up and took off my jeans. We kinda just stood their in our underwear for a few seconds.
Then he asked me if I was ready. I said, for what? He just laughed and pulled his underwear off, and there it was. I saw my first penis. He was obviously horny because it stuck straight out from his body. He had a patch of hair around the base, and it was pretty long and skinny. But I liked looking at it. He put one hand on his hip and with the other he took it and started to shake it and asked me what I thought. I told him it looked good. Then he said I had to take off my underwear. I was less scared now and more excited, so I took off my bra and then pulled off my panties. I remember him saying 'Oh my God' really softly and looking at my pussy. I only had a tiny bit of pubic hair then. He started rubbing his penis up and down and I asked him why he was doing that. He said it felt good and he did it when he was horny. He sat down on the bed and kept staring at me and told me I was sexy. I liked that! He really began pulling his erection fast. He said that he was going to have an orgasm, and I had a pretty good idea what that meant. He said to sit next to him and I could see better so I did, and as soon as I sat down he put his hand on my tit and started squeezing it. There wasn't much to squeeze!
He was groaning and staying funny stuff about how horny he was and how he was going to 'shoot.' Then he turned towards me and his penis was rubbing against my thigh. It was wet and sticky and kinda gross, but before I could pull away he shot creamy white stuff all over my leg. I told him it was disgusting but he didn't care. He got up and got a washcloth, then came back and told me to clean up. He put his clothes back on and so did I. He told me that if I told his mom or anyone that he'd beat me up and tell them that I was a liar, and tell me friends I was a slut.
Our moms came home about an hour later and we went home. My cousin and I talked about what happened about two years later. We had one more experience that was a LOT better than the first. I'll share that one another time.