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#14 Trey

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Trey was part of a group that I hung out with when I skipped class at a community college. I had a crush on him and made a proposition, which he accepted.I met Josh, the ringleader of this group, in the lobby of the technology building while waiting for class to begin. He was "alternative" in style (this was before alternative became a norm here in KY), and wore a spiked dog collar around his neck. I was into vintage clothes at the time, and I think I might have had blue highlights in my hair, so it was nice to meet someone so unconventional. Around the same time, my friend Michelle had fallen asleep on a park bench on campus and a young guy woke her up, afraid that she would miss her class. It turned out that this guy was part of the same group, so we all started hanging out together. Josh had a house not too far from campus, and this was the hub of activity for the group. He kept the door unlocked so people came and went as they pleased. Most gathered after (or during) their classes, and since I hated my history class, I sometimes skipped it and drove to Josh's. Occasionally, Trey would show up while I was there. Trey was probably the youngest in the group. He was short and stocky with dark skin and sun bleached hair from working outside. He had deep dimples and a nice smile, so it was a pleasure to make him laugh. I had a crush on him and from the way he teased me I suspected he had a crush on me too, but he was shy and got embarrassed when I teased him back. I had no desire to date him since I had to commute 45 minutes to get to school, but when I was around him I was overcome with a desire to screw him. So I devised a plan. The day after Thanksgiving, the group planned a dinner party, with the guys cooking all the food. I knew I couldn't drive home safely afterwards, so I planned to stay the night. Sometime during the night, probably while the turkey was cooking, I approached Trey, cuddled up to him (he looked a little scared), and whispered in his ear, "I don't want to date you, but I would really like to fuck you." Well it was obvious that he didn't know what to do at that point, so I left him and went to mingle with the 10 or so other people in the house. The dinner was surprisingly good for having been cooked by a group of 18-21 year old guys, and afterwards, everyone was satisfied, stoned, and sleepy. Along with the couch, which was filled with resting souls, there was a folded-out futon in the living room, and I lay on it with Josh and his girlfriend, who proceeded to make out beside me. At that point, I didn't know if Trey was up for my plan, but I was already horny from suggesting it. As I lay there wondering, he walked up beside me, grinned a truly sheepish grin, and said "scoot over." As soon as he lay down and covered us up with a blanket, I slid my arm around him and started kissing his ear. He turned toward me and kissed my lips and our hands began to roam. He slid his hand under my shirt, and as I unbuttoned his pants and reached in to tease his cock, he found my nipple and pinched it. I continued to rub his cock lightly and he moved his hand to my pants and undid the button. Then he slid his hand down and started fingering me and playing with my clit. I don't know how many people were aware of what we were doing; I suppose Josh and his girlfriend had a pretty good idea, as she was in on the plan. I was so aroused by the thought of so many people in the room that I almost had an orgasm right there. We played like this for at least half an hour, and it was by far the most erotic foreplay I had experienced. Finally I whispered "Do you wanna fuck?" and we zipped up our pants and went to the bedroom. Once there, we realized that we didn't have a condom, so I went back out and interrupted Josh and his girlfriend, who seemed pleased that things were going well. She gave me some rubbers and I went back in to find Trey already undressed and in the bed. He watched me take off my clothes and held up the cover for me to climb in next to him, then he got on top of me and let me roll the condom over his by-now-engorged cock. He must have been as turned on as I was by the living room session, because he only thrusted a few times before he came. Normally, I get a little miffed when this happens, but I really didn't think much of it this time because the foreplay had been so great. I didn't even think to assure him that I was fine with it. We smoked a few cigarettes and learned after-the-fact that we had a lot in common, then he went home. I learned from Josh's girlfriend a few days later that he was very embarrassed about his performance, and that the guys had found out and had been teasing him. Also, I never got a chance to tell him that I had a great time because after that night, I had to worry about finals and didn't get to hang out with the group so much. In fact, I don't think I saw him again after that night, but I had great masturbation sessions after that thinking about his fingers on my clit and my hand on his dick and our soft tongues together with another couple next to us and at least five others in the room.

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