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It seemed that every time it looked as if I was going to forget what I was wearing, I would catch sight of myself in a mirror. A man in drag. A man in a red teddy and black stockings. The gaff was the only problem. It was uncomfortable, and every time I saw myself in a mirror, I would start to get hard, and then the discomfort became acute. But then I would just look down at my crotch and admire the smooth, uninterrupted curve of the teddy as it went down and back between my legs. It was worth. The normal time I’d be beating off to some porn chick while wishing it was my sister was now being wasted. I was too nervous to do anything.Soon enough I heard car doors slam and heard the higher pitch of female voices cackling in the driveway. I went to the top of the stairs waiting to see them walk in and see what my fate was. The front door opened and I heard my mom and sister….laughing. Oh what a relief. Like a weight came off my shoulders. I heard my mom go into the living room and give. "Par for the course," I thought to myself. "Why exactly, do I let this happen to me?"A motor behind the wall started whirring and with a jerk the metal valet-arms began to rise, slowly sliding the rubber pants up my legs.With a |snap!| and a hiss, an air-pump also started. I looked down at the pants and mumbled "Uh-oh!" In the front of the pants was a large funnel, now aimed directly at my cock and balls. As the funnel got closer I felt air moving around my legs and genitals, and then with a. “Do you want to... ?”It was our last lesson before the holidays and although we pleasured each other orally after every lesson, we’d only fucked on two more occasions since that first extraordinary coupling. I still needed to enter her to the side, but it opened up delicious scissoring positions – me on top, her on top – beyond merely feeding my cock into her curled body on the desk. The most wonderful aspect for both of us was that these positions offered the deepest penetration and Penny was.
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