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W. was a frumpy, lumpy old redhead, with a wide ass and a prominent boob shelf jutting from the shapeless sack dresses she wore. To my nineteen year old self, she seemed ancient, although I suppose she was somewhere in her late fifties to early sixties. My room was on the third floor of the old house, sort of an attic under the roof with sloping ceiling and two dormer windows. There were two overseas grad students on the second floor, who I rarely encountered, and Mrs. W. resided on the main floor. I was given a key to the front door so I could come in late without waking her. After a few weeks I could tell that the old girl liked me as she would stop me on my way upstairs to chat about this and that. She would trudge all the way up to my room to change the bed sheets which she did not do for the other residents, and after a while she started to do my laundry which was not expected. Late one night after a hot but frustrating date with a coy coed, I came in to find the light was on. “What have you got there?” he said, looking at the bag I had brought with me. I handed him the bag and he opened it, and looked at the high heels I had brought. “GOOD GIRL!” he said. “You can leave them on while I fuck you, just like in the movies!” He told me that he had bought some makeup for me, and that I would have to learn to apply it. He was telling me all about his day as he drove, but I was only paying attention to doing my task of rubbing his crotch. When we got to his house, he had me go into the bedroom and put on my outfit and try some makeup. I did my best, but it wasn't great. I looked like a cheap whore who had been used all night, but I did look like a girl. Then he got out a Polaroid camera and a bunch of boxes of film. He had me pose in various positions...some very nasty. He took pictures of me sucking his cock, and looking over my shoulder with his cock in my ass. Carl had me fuck in many different positions. Doggie style, on my back, riding him, laying on my.
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