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During the time leading up to summer break, I had begun crossdressing. Itstarted with the clothes from the Halloween party. The thought of wearingthem again grew and grew in me until one day, when I knew Jessica wouldn'tbe coming over, I put them on. It was instant stress relief andrelaxation. It just felt good to be in them again. I felt more at peaceand better about myself when wearing them. Over the next few weeks, Istarted dipping into my saving to by an item here and there. I alsostarted perusing the internet to learn how to apply makeup and walk inheels; as well as trying to develop my female voice. I felt better andbetter as I dressed more and more often. I had a nice little collectionof clothes and shoes by the time the summer break rolled around.Back to the main story, it was two nights before our planned vacation. Ihad already finished my finals for the semester and Jessica had two finalson that day. I knew she would be out for most of the day; so I spent theday. I freaked out and hobbled out of class onto my next class.After that fateful Saturday night, John, Jen, and I stopped hanging out. We barely spoke during the school days, and I resorted back to my loser status. The rest of the school year, I spent my weekends either studying or sleeping. My senior year was coming to an end and my plan was an utter failure. It was time for Senior Prom and I was conflicted about whether to go. I was off my crutches at this point, and I basically faked through physical therapy as the gym brought back bad memories of the baseball player I used to be. The locker next to mine was Lisa’s. Lisa had big tits, but other than that plain jane. I think in 4 years of high school I spoke 10 words to her. Lisa was like me, a homebody with few friends. She was pleasant enough. Lisa had straight brown hair, wore little makeup, and didn’t dress very girly. I don’t think Lisa owned a dress. She was a jeans and t shirt kind of girl.The first 10 words were.
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She said it was. "It is Merv, you gave me your mobile number when you went to the financial conference", he said. "I was wondering if you were free and if you would like a dinner out. I'm here for a couple of days", he concluded. It took that amount of time and conversation for her to remember the events, not so much at the conference, but the room he was staying in with his friend and another colleague that joined them. "Yes I remember you Merv and also your two friends, how could I forget you all fucked me to the edge of exhaustion. Regards your question, yes I'm am free, very free and would be delighted to accommodate your suggestion", she said. A time was set and with a smile on her face, for she remembered only too clearly the delightful ravishing that she had received and the thought of again experiencing his throbbing cock was making herself feel giddy.She wore almost a twin to what she had on for the conference, but this time it was minus her bra and panties, but again.

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