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Yes, I had truly designed myself, at least outwardly. The common term was shemale, and I fully embraced the idea, not only physically, but in attitude as well.The trust fund left to me by my parents allowed me the means to live as I wanted and so I rented a Penthouse condo in an old converted building near the beach. It was a large open space with a kitchen and living area in the front and a large bedroom and bath in the back. In the corner was a metal circular staircase leading to a private rooftop patio which was perfect for sunbathing and entertaining.I was just finishing breakfast when the doorbell rang. It was Leena, my best friend in the whole world. Leena was three years older than me, twenty-three, and also a shemale. She had gorgeous brown skin and long, dark wavy hair. She was taller than me at five-feet-eleven-inches and had the build of an athlete. Beyond a more masculine body frame, the only tell that she wasn't purely female was her voice, which had a deeper, sultry. I had the hardest erection ever and I started playing with myself. I was staring at the mirror for like 50 minutes just jerking off non-stop. When I orgasmed, it was like 4 years worth of cum. It was my first orgasm. I think because my first orgasm was connected with crossdressing, my brain probably associates the pleasure of orgasm with dressing up like a girl. This is what we sissies call destiny. I was destined to be a sissy. If I could have it my way, I would make it law for effeminate boys to have their first orgasm this way.I think that’s what kept me interested in dressing up. That rush, heart-pounding, feeling of having the right colorful panties on. It’s like no other feeling ever. I was confused about my orgasm. I saw precum come out of my dick before but the orgasm was a feeling I never had before. It hurt a little bit but it felt soooo good too. I remember after I came, I ran to the bathroom and about 7 feet away in the other room, my brothers were playing video games. I.
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