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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. "Put your fist inside of my pussy. Go on, Carlo?" How would my fist fit inside of your pussy hole? Wouldn't that hurt? I don't want to hurt you." It won't hurt. I am so horny and wet your fist will slide right in. Come on, Carlo! Do it!"Carlo looked at his aunt with a strange look but pushed his fist up inside of her pussy. Once his fist was inside of her, he began to pull it in and out of her pussy.Aunt Jackie was moaning and thrashing on her chaise lounge. Carlo couldn't believe how wet his Aunt's pussy was. He continued to fist her until she screamed in ecstasy and had an orgasm on her nephew's fist."Wow! You got excited. That was so insane." Put your cock into my mouth. Do it, Carlo!" Hell yes! I need a blow job. I love when you suck my cock."Carlo took off his swim trunks and stood next to her chaise lounge. Aunt Jackie moved her hand up and down and opened her mouth wide. She fed Carlo's cock into her mouth while holding and caressing his balls. He watched as his.
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