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Recently I was thinking of how I actually transitioned twice in my gender life. For over fifty years I considered myself a cross dresser. In fact, for the longest time I considered dressing as a woman to be a harmless hobby. Obviously the longer I went along, the more I discovered it was anything but a hobby and far from harmless. All the time I spent agonizing over my gender issues proved to be very self destructive. In other words, I spent countless hours wondering what gender I was becoming and what I would do the next time I had a chance to dress in my secret feminine attire and admire myself. This stage of my life essentially lasted from when I was ten-ish until I was sixty and finally decided to begin my second serious gender transition. Although I can safely say I knew I was experiencing gender issues way before the age of ten.
Of course I am aware no one can reclaim time but I do try to learn from all of my positive and negative experiences. Initially, I was able to install lights in my transgender tunnel which would allow me to learn the basics of makeup and how to dress myself. I stumbled when I went through my girlish high school years when I was in my thirties. Those were the days I committed the usual cross dresser sins such as trying to dress too sexy which turned out to be a trashy attempt to disguise my testosterone poisoned male body in clothes designed for an attractive teen girl. Needless to say, those were difficult days for me in my tunnel when the light at the end always seemed to be the train.
Fifty years is a long time and still I persisted and more importantly learned what I needed to do to better prepare my feminine self to go public. I can compare the process to enabling my strong inner female to take control of the process. Approximately it was this time I went into what I called my business professional period of my life. An example was when I would dress up as my best impression of an executive woman and shop all of the upscale malls back in the day when many of them flourished and so did I. Rarely did I experience any issues as I shopped. One of my favorite outfits I acquired was a pale, pastel green suit with a short skirt which I paired with pastel green opaque panty hose and kitten heels. I topped it all with my shoulder length blond wig and was ready to explore the world as a woman. What a relief it was when…
