I gasped in pain with his large size, but he began pumping faster and harder. He laid me on my stomach and thrust into me. It hurt, but I took the pai... since we had discussed this online and I knew he enjoyed it. He grunted as he came deep in my ass, and then collapsed on me before sliding off. He grunted and smiled and admitted that was his first anal experience. I was in pain and wanting to cry a little, but as I felt his load begin to drip out of me I felt better. I stood up and gathered. After we had all the beer that we needed, the guys had more fun lined up for us. They drove us out into the less populated area of the island, to a wilderness area with trails and waterfalls and even an ocean view from on top of the cliffs. We were all given our t-shirts to wear and shoes, but nothing else. Most of the girls had longer t-shirts, because they were using them as cover ups for their bathing suits, so they could move around a bit without their asses showing, but mine and Kathy’s. I was out of town on a business trip and I went to Walmart and bought a pair of panties, stockings and a mini skirt. I then went to a gas station bathroom and put on my girly things under my man clothes. While I was in the men's room there was a message on the wall that said, 'call for a good time.' So I wrote down the number and went to a payphone, yeah, back then there were pay phones.I called the number not expecting anyone to answer, or for it to be disconnected. To my surprise, a guy did. The first few weeks were orientation, the k**s did not show up until later in the summer. I had just turned eighteen and was the youngest of the group. There were several college age students. And one other group from my own high school. Unfortunately, it was the more popular crowd, the group that had picked on me throughout high school. Jim was one of jocks that always picked on k**s like me. His girlfriend Melissa was the hottest girl in school; she was always the envy of the entire school..
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