My brown hair was always spiked to perfection and I showed off my sparkling smile at every opportunity. After working out for all of my high school years, I had developed a toned body, and my skin was a solid bronze due to my frequent visits to the tanning salon. The girls loved me, and I loved them, but the whole routine was getting old. Every weekend, I’d hook up with the same type of girl, it’d seem. Lots of make-up, slutty clothes, easy to take home…It was getting rather boring. I needed a girl that would be a challenge. A girl that didn’t want anything to do with me. A girl I’d have to work at.My birthday came early in the year, so I was beginning my senior year of high school already 18. My sister and I were twins, so she was 18 as well. It was about two weeks after our birthday that my fantasy about hooking up with a challenging girl came to life in a way that I couldn’t have predicted.I was sprawled out on the couch, watching some TV after dinner. My parents had gone out to. "No he's not!" I said shyly - I actually didn't think hewas.He was slim and about my height. As I glanced at him I mustconfess he did look handsome with rugged looks. I wassurprised to find that he too sometimes came to the clubdressed, but most often as a guy. Though not beforeconsidering myself in any way so inclined, the thought ofbeing attractive to a man was the ultimate femalecompliment and the thought excited me.As I mulled over the thought, I felt a tap on my shoulder."Excuse me..." It was Alex! "You're not from around hereare you?"I nervously replied in the negative. He offered to buy me aglass of champagne - astute at least, I thought. We chattedand when he confessed that he too was a crossdresser Iconsoled him with the fact that I already knew. He saidthat I was one of the most attractive he had met, andstated that my dancing was certainly the sexiest. We dancedfor a while and he invited me back to his place. Iexplained my previous arrangement and within a minute hehad.
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