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 ...ister. 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. ‘Oh, well, that’s… interesting’. Correcting himself, he asked again, ‘How long had you known ‘her’?’ ‘Not long’. ‘How long?’ ‘A day… If that’ She repeated in a tiny voice. He smiled, nodding, ‘She must be really something’. Jennifer smiled to herself, ‘She is… She’s a lot like you, actually’ she paused to look at him, ‘Charming, apathetic, beautiful,’ Caleb laughed, her eyes met his, ‘she’s just not as cruel’. He continued to smile, nodding to himself. ‘So why aren’t you still seeing her?’. More

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