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


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

    biologically a boy, enjoyed masturbating and very thoroughly enjoyed anal stimulation. It wasn’t till the later years that started to question if my appreciation for anal pleasure tied in some way to my sexual preferences or sexual identity. I certainly didn’t reach any conclusions at the time but didn’t let the internal exploration of it worry me to much either. I knew I was attracted to girls and never really did get sexually excited by boys, other than the curiosity about how they could potentially (or not) fit into a situation that I would find sexually pleasing. This ultimately lead me to trying to find someone (using the internet of course) that I could explore these things with. I started chatting in adult forums and found a few adult oriented sex sites and ultimately stumbled upon a gay site to try and seek a guy who would explore the phallic sexual experiences with me of which I was so curious. I found a guy who lived about 10 minutes from me and we chatted for days and days and after a few weeks, I finally decided that I wanted to try it out genuinely, we actually tried setting things up and meeting a few times before I finally had my first anal experience. It was very painful, but the thoughts that I had after the experiences were ones of wild passion and desire and I knew I enjoyed that sexually submissive and bottom role in relationships when guys were involved. I still never considered myself gay nor even bi really because I had always thought that to be gay ...
    one had to desire and feel true intimacy with someone of the same gender identity to their own. A man or someone desiring to be a man with the desire to kiss and be intimate with another man (or someone desiring to be so) was what I thought of as gay. Probably some over rationalization in my mind, but I loved kissing girls, I loved playing with girls, I loved having sex with girls, and I loved being very close with girls, whereas I didn’t like or really want that with guys. I merely wanted anal sexual gratification and so, at the time, I think a TS girl or a girl with a strap-on would have possibly met the desires I was seeking at the time, but that concept never really crossed my mind back then. This has evolved over time and what I desire from guys a girls is different from back then and so I consider myself bisexual now, whereas I still don’t think I was bi-sexual back then in the way I view things now. My desires and appreciation for dressing feminine proceeded in secret for quite some time, but I never explored it all that much before college. I left home for college in western NY (Rochester, NY specifically) and was up there for seven years with the exception 1 year I took off to move home and help my parents with my grandmother, and 1 year of internship I did for a research company in San Antonio. While in college, I was very far from home and this gave me more time and freedom to explore my sexual identity and just try to be who I wanted to be at the time, not overly ...
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