I thought I was a Casanova and knew everything. There was this couple that I would do stuff with and caddy for, Daisy and Walt. Daisy was a sweet heart and fun to talk to and very classy, Walt was rich drunk and drank all the time but he was cool till he had too much to drink. One day we were on the course, we would played about eight holes and then ended up at Walt's house. We were all having a good time, Daisy and I flirting and Walt drinking. Once at the house Walt quickly reached the point of too much. "Well Mike, are you getting plenty of pussy. When I was your age I was fucking every girl in sight." Walt said. "Walter, behave yourself." Daisy snapped. "Daisy was one of the girls I fucked every chance I got. Well all the guys did." Walt stammered. "Walt, Mike does not want to hear about you escapades or mine for that matter." Daisy said maintaining her class. "We all liked fucking Daisy, she has a great little pussy. Cute little tight thing that gets dripping wet in two seconds.. He just smiled and said he would love too.We got together quite a few times, when I wasn’t busy with others and they were always fun. He bought me my first real dildo and vibrator, he also brought nipple clamps, anal beads, restraints, and penis pumps. He got more and more comfortable with me and one day he asked if I would mind if he wore an outfit for me, I said what kind of outfit, and he said it was just something he wanted to try. I said sure I am game. When we got to the motel he took a back pack out of the car, and we went in, He went straight to the bathroom and was taking a while so I laid on the bed naked and started using my vibrator. I quickly brought myself to orgasm and then to another one when I heard the door open. He stepped out and I was shocked.He was wearing white thigh high stockings and heels, he had shaved his legs, his little soft cock was clearly outlined in his while silk thong. He had on a white corset and was covered by a sheer waist length robe. He put on.
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