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After a few minutes of him starting to slow down, I pulled out and flipped over to my back and put my legs in the air. He kept asking me how I was doing, I told him to just keep going.
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Wow it felt like my skin inside was being stretched out. Then I felt his rock hard shaft push its way into me. I told him to go ahead as I was already nervous. He told me that he is quite a bit bigger than his finger and that penetration might be a little painful or uncomfortable. I told him that felt good and it was true. I felt a splash of something wet touch my hole, then his finger pushed inside me about an inch. He told me to lay flat on the bed, face down, legs spread. I quit sucking him and asked him how he wanted me. He grinned and said his biggest turn on is to take the anal virginity from guys. Then he asked me if I had been penetrated before, and to be honest, I said no. He asked me if I wanted him to penetrate me, I said yes. His pubes brushed up against my nose, and the entire area became a sloppy mess. To impress him, I pushed my mouth as far down as I could, trying to take the whole thing.
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The tip of his penis would hit the back of my throat and to my surprise I didn't gag. As I sucked, he put his hands on my head and controlled the pace. I remember his skin tasting rather bland, which was ok by me. To hide my cock, yet seem interested in sex, I got down on my knees, face near his cock, hands cradling his balls and asked him "may I please go down on you?" He said yes. I proceeded to take off my clothes but felt inferior to him as I was certainly less endowed. He asked if I would as well, as my eyes were fixated on his big cock. We got to his apartment and he didn't waste time taking off his clothes. I was shy because nobody had seen me naked before and here I was planning on going to have sex! I was also nervous as I didn't have condoms. I was wondering if he was a top or a bottom. I started to wonder what was going to happen. So we had a couple of drinks, and he asked me back to his place, which was walking distance away. He asked me if I was uncomfortable, to which, enjoying the attention, I told him I like it. We got a table at the pub and as we sat down, he put his hand on my leg. We chatted until the library closed and he walked me out and asked me if I wanted to go for a drink. One day at the university library, an older guy noticed I was reading about travel and we got into a conversation. I think most girls preferred a guy with more bulk than my lean build. Fast forward to midway through my 2nd year, I had just lost 70 pounds but was still a virgin. I started noticing less girls smiling at me and eventually started working out and going on a vegetable diet.
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My first year of university, I gained weight. I dressed poorly, and was starting to become overweight. I came from a sheltered middle upper class upbringing, but was raised to be cheap. Leaving high school and going to university, I believed I was completely straight.