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Back then, it was all about the excitement of doing something apparently taboo, which really excited me. I felt dirty and embarrassed afterwards (thanks to my catholic upbringing), but I still loved it. I had started wearing my mom's and my sister's clothes since I was 10 but I was growing taller and they were not. Had a problem with the shoes too. Dressing as Santa Claus for a 3rd Grade Christmas party at school gave me the opportunity to wear Mom's black boots in public, that was so exciting.That was the main reason why I went for the stretchy clothes and luckily, Mom's wigs still fit. I still did everything behind closed doors and when everyone was not home. Nobody knew, at least that is what I thought. I really enjoyed prancing around when no one was home; I came savagely several times, usually with something big up my ass, all the time wishing I had someone to play with.At that time I was still going to college. I was taking a Philosophy class that most people thought was. I walked around, I tried to open the draws and cupboards to see what Miss Appleby kept in them, but they were locked. I sat in her thickly padded leather swivel chair, and twirled round and round. After about ten minutes I was bored. Slumping back in the chair, I sat twiddling my thumbs. My hand almost then automatically moved to my willie. I took it out and gave it a comforting rub, suddenly I spotted a straw basket in the comer, inquisitively I looked inside. On top there was a scarf, I pulled this away and dug deeper. There was a blue tennis skirt, a pair of gym socks, and underneath, the real prize, Miss Appleby's brassier and a pair of French style silk knickers. This was amazing to me. I picked up the panties and slowly put them to my nose. I sniffed them, then gently turned them inside out to see if there was any thing inside. I sniffed the insides, then rubbed them softly against my chin. By now my cock was as stiff as a yard brush, and I took it into my hands and began to.
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