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”“So what? It’s not like we’d be having sex. Besides, it might be fun.”Well, I could hardly argue with that. Besides, my cock was already getting stiff.Understand that I was very inexperienced at the time. I hadn’t dated at all, all the way through high school. I guess I thought I was unattractive. I was really shy. My sex life so far had been limited to looking at back issues of Penthouse and fantasizing about Shannon Kelly (or whoever my obsession du jour was). It had never seriously occurred to me that a girl might actually be interested in what was inside my pants. Now my own sister seemed highly interested in just that.Stephanie was fumbling with my fly before I had a chance to say anything. She fished my penis out from inside my boxers.“Not bad Little b*o. Here, it’ll be more comfortable if we get your pants down.” I lifted my ass off the couch, and together we worked my jeans and boxers down. I felt incredibly exposed like this. I really couldn’t believe it was really. He began to build a real desire for his very own tranny experience. And the culmination of all of those years was going to burst open today. On a business trip to Oakland, he had had a slight layover in Vegas. During this layover, he did what Julian normally did in Nevada. He threw a $20 at the dollar machines, and hoped for something big. This time, it happened. Jackpot! $10k! He was given one thousand, and the rest would come in the mail he was told. But he had money in the bank. He could 'float' himself a loan! As Julian boarded the plane to Oakland, he was jittery, knowing exactly what he would do. In Oakland, a quick zip through the terminal, car rental stop, and the hotel went by in a blur. He was in Oakland and it was Saturday around noon. Once in the hotel, he began searching in Google. 'Shemale escorts', 'Tranny dates', etc. etc., when finally, he found an ad on Craigslist. Tonya Devine was her name. She had her own website, with pictures. Tonya was a beauty. She had nice.
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