1. My road to womanhood (so far....)


    Date: 8/10/2015, Categories: Anal, Shemales, Author: UnDressed2Thrill, Rating: 100, Source: xHamster

    concerned with what my f****y might think. Everything I continued to do was very much closeted and the friends I had at school didn’t know of my proclivities. It was also during my college years where I found the idea of transgender girls to be very very interesting and started to seek out, learn, and understand this aspect of sexual identity/sexuality. My b*****r had moved to San Antonio for his first job out of college and that is where I did my first internship after my second year of college. It was during that year I was in San Antonio that I had my first meeting with a transgender girl, I had just turned 20 and was no longer a teenager. I was still dressing fem in private and at the time I had two often polarized “moods”. Sometimes I wanted to be with a girl (TS or GG) while other times I wanted to be the girl and dress, but it was rare that I would feel the desire simultaneously. Not until I met Jamie. She was a CRAZY gorgeous TS girl. She was Latina and had the full package of what I believe most would view as the quintessential trans-girl. Hour-glass figure, huge boobs, gorgeous ass, perfect body all around. She was very feminine and pretty too, full and soft lips, female cheek bones/facial features, soft olive skin, all around gorgeous. Well one night, the 3rd time me met up, she actually asked if she could “top” me. Previously, whenever I was with someone who was feminine (only genetic girls at the time), I was the top and when with someone masculine (only genetic ...
    male) at the time, I was the bottom. This is one of the turning points that changed my view of sexuality and gender identity and put me in a new perspective. She was absolutely gorgeous and whereas I previously only wanted to fuck her, after that night I was much more open to having close sexual intimacy and desire while also being a bottom. We switched pretty much every time after that and I developed my love of being both closely intimate with a sexual partner while also being a bottom. My view and genuine consideration of being a trans girl really flourished at this time, granted it was still very focused on sexual desire and was highly fetishized in my own mind. Regardless, Jamie opened up my mind to genuinely considering transition. Pressure to be “traditional” in the eyes of f****y and friends held me back and kept me from moving in that direction at the time but the desire grew. A few sexual experiences with girls, guys, and trans girls continued throughout college and there was a time near graduation where I was more-or-less dating a guy, but only when I was fem. He had his own place in downtown and lived with a few of his friends, he was “straight” but liked trans girls because we tend to try much harder to be feminine than genetic girls in some cases (likely because we’re less likely to take femininity for granted) and that is what I found the most intriguing about him at the time…he was open about his sexuality, said was open about saying he was straight while also ...
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