Her nipples were obviously hard as rock. The cunt that she was playing with was clearly wet and needing his cock. He got on the bed between her legs a...d pushed. Fuck, she was tight. He pushed again and could see her gasp in pain.“Please go slowly Daddy.”She wasn’t teasing now. He leaned forward to change he angle and his chest crushed her tits. She loved the feel of his muscular black chest on her tits. She wrapped her legs around his and fucked back the next time he pushed. He heard another. Each session would end in an enormous shot of cum, with the ensuing shame and guilt that crossdressing often produces.It was 1985 and the Internet wasn't on the pop-culture scene, Jack thought he was the only teen in the world that desired to wear women's clothes. Sometimes he would rummage through the wastebaskets and retrieve his sister's discarded pantyhose and hide them in his room. Without fail, the guilt would build and he would purge his collection.To date, Jack's favourite crossdressing. More

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