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My name is James, I am 44yrs old, I have enjoyed dressing up in womens clothing since I was a teen. I was raised in a home with just my mom and older sister. Whenever I was alone I would sneak into my mothers bedroom, pick out a sexy outfit and transform into Jaime, my female persona. I was now 18yrs old.One early Saturday my mother and sister headed out shopping, as soon as I heard the car leave, I locked the front door and I headed to mothers room to dress up like a little slut and. "Well, give me a few days to get used to this and we can meet," Terryreplied coyly.The man on the other end of the line laughed."So is that a yes? Or are you too insecure about your own masculinity tomeet me in public?" asked Terry.The man laughed even harder."I'm cool about this if you are," he replied."I'm glad to hear that," said Terry."So, when do you want to go out on a guys night out?" he asked."I'll give you a call as soon as I know my schedule. I suspect that we'llbe busy for the first. It seemed like half the human girls at Madison University had the exact same story she did, you know the one:You find your boyfriend on the hill, at the make-out spot that was supposed to belong to the both of you; but instead he's got his lips lathering up the gigantic boobs of that pixie transfer-student that arrived last week. Yes, yes, he's supposed to chase after you claiming that it's not what it looks like, when it obviously is. But he didn't even do that; there was denying the obvious;. I kept going, I had no idea what I was doing I just knew I wanted to touch her, touch inside her. ‘ Not here ‘ she whispered and turned around , she kissed me and walked off towards the bedroom and as she rounded the corner she said ‘ give me a minute the come in ok? ‘. I stood at the sink in shock, this was it, this was the moment I lose my virginity. I sniffed my fingers where they had been inside her, the smell of a woman. I took out my cock and began stroking it but had to stop as it felt.
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