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We kept meeting for coffee, and lunch, for the next 3 weeks. The next time we got together for lunch, he put an envelope in front of me. He said they were his papers. I then pulled one out, and set it in front of him. We both pulled out the sheets of paper, and silently read them. We both looked at each other, and smiled. He then asked me if I wanted to come over to his place, and I said yes. I followed him to his apartment, and parked. After we entered his place, we got comfortable on the couch. He asked me if I wanted to watch a video, and I said sure. He then started the player, and on the screen, was a cross dresser, sucking on a man's cock. After watching the movie, I looked over at Dave, and noticed he had a little hard on. As the guy on screen was fucking the cross dresser, I asked him what role got him excited, and he said the part of the cross dresser. I asked him if he fantasized about fucking the cross dresser, or being the cross dresser. He then said he fantasized. First she put one finger into my ass after a bit she added a second finger this was giving me a new hardon after a bit more of her drilling me with two fingers she added a third I had never had anyone jam anything into my ass but now I was in heaven. I was so hot and hard that I almost came again. She than turned me over on my stomach she put a couple of pillows under my belly which raised and opened my ass to her she parted my chiches and slowly inserted her cock into my ass first her head it hurt a lot but now I was so horny I told her to push it in some more, than she said was I OK and I said it hurt like hell she said I could take it that I would feel better after I was used to it. She waited a little letting me get used to it. Than she started to push it all into my ass she stopped again and waited for me to get used to my ass being filled with her cock. I hadn't noticed that my cock was so hard but I felt it between my belly and the bed sheets I said I was ready to start real.
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