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 was...'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. I grabbed onto his wheelchair and lower myself some more. He reached around and plays with my nipples, pulling on them and squeezing them. I lower myself and take six inches and try to raise myself back up, he raps his arms around me, grabs my breasts squeezes hard and shoves me down on the other couple of inches. I scream in pain and he tells me to fuck him. I rock my hips back and forth and let his long dick slide in and out. I lift myself up took the dick all the way out and slammed myself. More

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