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We chatted for some time, and I kept checking the on-line load boards. I kept checking her out while we talked too. I could tell she was doing the same. I found out she was heading to Portland so I started looking for loads going that way. The conversation kept moving towards sex, to my delight as it had been a few days. I finally ask if she wanted to climb in the sleeper. Portland said she would like that very much. My mind went into overdrive thinking, Am I clean enough, will I come too soon, do I have condoms on-board, etc. Too late she was already heading towards the back. I told Portland I have a rule she had to follow. She stopped short and looked at me with that ‘and what’s that’ look. I never sleep in the bed with clothes on. It keeps the bed clean. I said and you have to be naked in bed as well. She just started stripping without a word. Oh was this just getting better by the minute. When Portland started to shed the layers of clothes her fine body was better than I. I've got big plans for you, Girl. And you're going to find that they're a lot bigger than you bargained for."That sounded nice. Part of my fantasies always consisted of being made to do just a little more than I wanted to. As for a lot more, I doubted whether she could. I didn't think she, or anybody, could plan anything wilder or more fantastic than the ones I had imagined many times. I was wrong.I spent all day Saturday in that teddy. It was a lovely experience. 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 discomfort. Why hadn't I.
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