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I knew if I ever had a shot at asking Debbie out it was now. She was alone by the water cooler. This was my chance. I took a cup and poured myself a drink. ‘So um Debbie,’ I began. ‘You know, I um, don’t wear a dress all the time. I can be, you know, normal. ‘ She threw her cup away and gave me an odd look. ‘What are you telling me this for?’ she interrupted. (Uh-oh) ‘Are you coming on to me?’ (BUSTED!) ‘Because if you are I’m OK being with a guy who likes to wear a dress.’ (Is she throwing me a lifeline?) ‘In fact I think it’s kind of kinky’ (YES! YES! YES!) For our first date Debbie gave me a tour of Pleasant Town’s club district. It was early evening in mid July the sun was just starting to go down. I wore a light brown sleeveless dress while Debbie had on a white blouse, black tight fitting slacks with a matching big rimmed hat. Usually I like to watch all the guys do a double take on me. That’s what makes wearing a long red wig even on a hot day worth it. But tonight, my focus. Cindy arched her cunt toward Jacks swollen cock as he thrust forward into her. He took it gently at first as he new she would need to get used to the extra size of his cock. Cindy gasped as her cunt was expanded to accommodate this huge cock. The wondering was over, she now new what it was like to have a large cock in her cunt. It was hurting slightly, but was also enjoyable. Jack moved slowly in and out and the slight pain in Cindys cunt was soon replaced by the pleasure of it all. She responded by fucking back as Jack thrust his huge member in and out of her cunt. The tempo increased as Cindy got used to the bigger cock that was now pounding her. She could sense that it would not be long before she would cum for third time and the night was yet young. She couldnt believe that such sexual wanton could be so pleasurable. She had only ever been fucked properly by her current husband. Her first husband didnt know what sex was really about. This was so different to what she thought and.
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