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Charlie also knew that I toyed with my ass, so he probably assumed I had let some other guy have it. But I had always held out hope that we would one day get together again. I'd had some pretty big toys in my ass. They weren't as big as Charlie's cock, which isn't a monster, but they were big enough that he didn't have any trouble relaxing me and sliding it in. This was new for us so we tried a doggy position, something we can't do for vaginal fucking without the creative use of furniture and padding to match heights. It's not quite as bad as a Chihuahua and a Great Dane, but it's one of the adjustments we had to make. Fortunately, my asshole was just that much higher that his knees didn't have to spread too far. I was kneeling, not far from the headboard, and using it to hold my upper body up. Charlie put his hands on my hips and I felt his thighs start to smack against the back of mine. I had thought my pussy was done for the night, but I moaned when I felt a jolt of. I spent the few nights dressing up, and trying my hand at makeup, I did alright, and I didn’t look bad, as I already had long blond hair, almost no body, or facial hair, long legs, and a nice round ass. After a few days of playing alone, I decided to check out the local alternative lifestyle club, I heard they had drag shows, and it was a fun place, so I caked on the makeup, eye liner, blush, and lipstick, put on my stockings, skirt, padded bra, and a tight cut button down, it was the best I’d ever looked, I didn’t plan to meet anyone, I just wanted to get out there. I arrived at the club via cab, the cab driver kept leering at me in the mirror, I wasn’t into him, but I was flattered, as I know my body was rocking. When I got there, I sat at the bar, it was an older crowd late 30’s to 50’s I would say, and here I am 18, and nervous as hell, everyone was nice, I even got hit on by a few guys, I mainly just sat there watching the baseball game on tv. Just as I was about to leave I hear.
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