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I haven't always been a crossdresser, when I was very young I remember being fascinated by women's legs in nylon stockings (they still wore stockings ...n those days). I remember being at a friends house, and his mom used to put her son over her lap and rub his back with a soft brush as a form of reward, it was like a soft back-scratch if u like. One day she asked me if I would like a 'rubbing' and of course I said yes. She always wore skirts just above her knee and I noticed she always wore. I lifted his legs and licked on his ass hole. I worked my fingers in and out for several minutes to streach it out some. When I had three in him, I replace them with the head of my now hard cock. I pushed slowly in a little and back out. It took a few minutes but I got my head in. He said it hurt so we held off a few minutes before working some more. Eventually I got all the way in and started fucking him slowly. All the way in and all the way out. He said it felt good now so I went to. More

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