It felt fabulous! Then I zipped it up the back. I looked in the mirror. I was a woman!The skirt felt great swishing against my nylon clad legs as I paraded in front of the mirror. Then I saw a pair of my mother's black patent high heels. It was a tight fit as I was 2 shoe sizes bigger than her, but after a struggle I managed to squeeze them on. I looked in the mirror again, what I saw made me feel soooo sexy and soooo dirty. The feeling was so good that before long I'd hiked the skirt up round my waist, pulled the tights and panties down under my cock and balls, and masturbated my self to an incredibly fulfilling, almost spiritual orgasm.I the weeks that followed I tried on all sorts of underwear, dresses and skirts, and squeezed myself into various sexy women's shoes, and naturally almost wanked myself into a coma.The risk of getting caught by my sister was now much higher, as it took longer to get the clothes on and off again. One day my sister came home early, just as I had hiked. I’ll give you my credit card.’ ‘OK, I’ll go but I think you’re crazy. Remember, the banquet is in another month and I’ll be showing a little as well. As skinny as I am, maybe even more than a little. Are you sure you’ll want to be seen with me?’ ‘Of course I want to be seen with you. You are a lovely girl. A lovely intelligent sweet woman that any guy would be proud to be seen with. You just get what you need and leave the rest up to me.’ A couple of weeks later on a Saturday, Penny decided to go shopping. Armed with Charlie’s credit card, she went to a few dress stores trying to find just the right dress. Having seen pics from past banquets, she knew the style so all she had to do was find the perfect dress. She finally went into an upscale dress boutique and the sales woman helped her find the dress she was looking for. She even arranged for it to be quickly adjusted based upon how big Penny’s stomach got. Satisfied with the dress, she went and got matching shoes and a cute clutch..
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