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Hillary generally purchased cheaper, supermarket hose, but that didn't matter to Jack.Things continued on like this for the next few years; Jack would play dress-up in Hillary's clothes, admire himself in her mirror and fantasize about the girls, and teachers, that he had recently seen all dressed up in hose. 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 moment had to be Hillary's junior prom night. Hillary decided to get dressed to the nines, which fortunately for Jack included her choice of hose. Hillary and her mom went out together to. Each time I would gasp and pull away a little but at the same time I would be enjoying the feeling. It was certainly something I had never experienced before. His tongue was amazing. And I could feel the pressure inside me growing again. Histongue continued to lick my clitoris and as I began to get close to the edge of an orgasm he would change his tactic and move to licking my pussy and briefly as if by accident my arsehole. Then he’d go back to my clit. This teasing drove me wild and he knew it. It was so hot and horny! Eventually, desperate to orgasm I begged “oh please don’t stop, let me cum, pleeeeeese!” And as he immediately moved back to circling my clit I came within seconds, with the orgasm ripping through my body with such strength I was unable to do anything but lie still for a couple of minutes once it had stopped. Once I had recovered, I began to wander where my stranger had gone. The room was silent so I didn’t think he was.
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