The second drawer held her socks and pantyhose. 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. Anyway let’s get on with the exam.” he replied. As he was staring at her it was then that Jessica spotted something she couldn’t believe. The good doctor was actually getting hard! His pants were tight enough and you could clearly see a slight wet spot forming. Ah ha! So he was interested in her. Sweet! “I’m going to begin the breast exam now. Is that ok with you?” he asked with a tentative look. “That’s fine by me” Jessica responded. The doctor moved over to her left side and moved the sheet down to her waist. He began with her left breast and with two hands (One to hold the breast and the other to feel) he began to press her breast. He went from the outer rim all the way to the nipple. Then he did something she’s never seen done before. He pinched her nipple! “Oh” was her response as she tried not to move into the sensation. “Did that hurt?” he asked. “You said it had been a while since your last sexual encounter so I thought it would be best to check.
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