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#1 Dylan

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Dylan and I shared many firsts. This post relates most of them.Dylan was the first guy ever to kiss me. It happened when I was 14 in the back seat of the school bus on our way home from an away basketball game. He didn't make his move until we were almost to our school, and his palm was sweaty in mine. I guess I was aggressive back then because I was very impatient waiting on him to kiss me already, and the second it ended and he pulled back, I grabbed his head and laid another one on him. We broke up after basketball season and got back together when we were both 16. By that time, he had shot up in height and was one of our star players; all the girls had a crush on him, as I had ever since that first kiss. He turned out to be about 6'3" (the first time we dated he was like 5'6"), with a six pack and a nice-to-grab ass. Every year his parents went to Florida, and when he returned he always had sun blonde hair and a dark tan. He was a show-off, too, and loved to flex his muscles when the girls were watching. But he did it in such an I'm-not-doing-anything way that we pretended we didn't notice. Anyway, we cheerleaders loved to watch. We were both virgins when we started dating that second time, and we felt so comfortable (and horny) with each other that it was only a matter of days before we started exploring each other's bodies. One of the first times he came to my house, my parents left us alone while they went out to eat. They might have been a mile down the road before I was straddling him on the couch (a move that turned both of us on to no end) and letting him run his hands up my shirt and down my pants for the first time. I was nervous because I could tell I was soaking wet and I didn't know what he would think about it, but once his fingers were inside me I no longer cared because it felt so good. When we had sex for the first time a few months later, my parents were again gone, this time to support my cousin who was in labor at the hospital (ah, the irony). We waited till midnight and almost missed our chance, but as nature would have it, it didn't last long. We were so nervous that I don't think we even got all the way undressed. I just wanted to see what it was like, like every other teenage girl I guess. I must say I was somewhat disappointed, mostly because I thought that something spectacular would happen just from the intercourse, like the world's best orgasm. It didn't hurt (though it did next time), and it did turn me on, but I remember thinking that it wasn't nearly as good as masturbation. The sweetest thing about the night was that he didn't want to leave me and go back to his house, even though he was already late for curfew. I stood at the door saying "you have to leave," and he kept leaning in and kissing me and saying, "I want to do it again, just one more time, please??" The real good stuff happened after we had been messing around a few more weeks and I showed him how to make me cum. We were laying on the sitting room floor "watching TV" and he was behind me in the spoon position. He was kissing my neck and he had his hands in my pants, which I had unbuttoned for him. He was feeling around and he kept brushing past my clit, so that it felt sooo good one second and then just good the next, so I turned on my back and took his finger and rubbed it across my clit a few times, like I did when I was alone. "Do it like that," I whispered. I kept my hand on his and put it where I wanted it when he missed, but for the most part, he caught on quick. With my other hand, I unzipped his pants and reach in for his hard cock. I grabbed it and started pumping it up and down. He kept rubbing my clit and moved his hand faster, and soon my pussy started tingling and I knew I was going to cum. "Keep going," I said out-of-breath, "just like that." This was the first time anyone had ever masturbated me and I was extremely turned on by it. Almost before I got the last words out, I came hard. This pushed him over the edge and he leaned over and kissed me as he came. He became very adept at rubbing my clit exactly the right way, and he always like to time it so that we came together. He also loved to kiss me right at that moment. Our favorite intercourse positions were those that made it easy for me or him to rub my clit. One of my favorites was for him to sit on the couch and me to sit on his lap with my back to him. I would put my legs on the outside of his, and since I was much smaller than him, he could hold me by my waist and move me up and down. I could cum easily like this, and I loved it because I could look down and watch his dick slide in and out of me. We couldn't do this too often early in our relationship because my parents were usually home. Instead, we'd get a blanket and lay down on the couch with him behind me and watch TV. Eventually his hand would slide in my pants and he'd start rubbing my clit, just like I'd taught him (he knew he could get me in the mood anytime by doing this), then we'd slide our pants down and he would enter me from behind, still rubbing my clit. A few times, my mom even walked into the room while he was inside me. This was both nerve-racking and exciting. The whole time she'd stand there talking to us, I'd squeeze my muscles then he'd flex his dick, which was interpreted on both parts as "Oh my god!" When I think about it now, I'm surprised we got away with all we did. But I guess we didn't really, because not a year later I was pregnant. That's another long story in itself, but suffice it to say that he's still in my life to an extent, and we have been known to hook up every so often and re-live past experiences. One of the most memorable of these reunions happened a few years ago, when our daughter was on vacation with his parents and he talked me into going skinny-dipping with him after dark. When we got to the swimming hole, there were already a few couples there and I was hesitant at first, but he went in and urged me to join him, so I stripped naked and swam to him. We clung to each other kissing and talking with the other couples and watching them kiss. Afterwards, he took me back to his place and we took a bath together. In the bedroom, I got on my hands and knees on his bed, expecting him to enter me from behind, and instead he leaned down, spread my pussy lips open, and licked me to orgasm. Yet another first from him. Nowadays he's married again and even though we agreed that we'd hook up, married or not, every few years, we're just friends at this point. Still, I can smell my pussy just thinking about him, and I wonder if his new wife is enjoying him as much as I did.

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