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Nervous as hell I spent several hours getting ready. Shaved, lotion, body sprays, make up, red head wig. My outfit was open boob tedi with garters and stockings underneath a spaghetti strapped black short dress. So I called an uber to take me to this local place about 15 minutes away. As I entered of course a got some stares as I made my way to the a seat at a small table for 2. It was awkward for about 20 minutes until they realized I was alone, but probably a visitor from out of town, my bar server was a very hot young gay server who made me feel comfortable. I was sipping wine most of the night, met some interesting gays, lesbians and even a few shemales. it was amazing how many gay men were so forward in getting me to leave with them. As the server brought me another glass of wine he said, a gentleman at the bar sent it as well as mentioned the gentleman would lie to pay your tab as well. The server pointed out an older bald headed nice bodied African American gentleman who. "He said he wouldn't. He begged and pleaded with me to change my mind. But I played my trump card."You know," I said. "The girl at the lingerie store, I think she knows you. Gorgeous little blonde thing. Hayley, her name is. She says she takes a class with you at school."His eyes widened. I knew for a fact that he had had a crush on Hayley forever.I laughed. "Don't look so scared, Darling. I didn't tell her all this lingerie was for you, or show her that video of you in my nightie that I saved on my cell phone. And I won't have to do any of that, I promise, as long as you do everything I say tonight. Ok?" Take off your clothes," I said. "Now." He began undressing, slowly at first, but faster when I mentioned that Hayley had given me her phone number and that we were meeting for lunch that week. Soon enough he was standing there, pale and naked and scared in front of his lingerie-clad mother. He was so embarrassed. And not only was he naked but he was hard, remember? I almost burst out.
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