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| Photo from the Jessie Hart Archive |
The earliest boundary I faced was learning how to dress and makeup myself to present well as my feminine self. As most of us know, just learning the art of makeup is daunting enough. Not to mention the time effort and money it takes to acquire and wear a new women's wardrobe. Believe me, the process involved more error than trial until I finally began to get the process right. Problems included not dressing for my age and body shape. In other words, I certainly wasn't the teenaged girl I was trying to look like. Predictably my early experimentations did not work because of my testosterone ravaged body and I just ended up subjecting myself to ridicule by the public. Learning my boundaries of how to present as a woman were difficult to learn but I did become fairly proficient in the ways of dressing to flatter my body style (the best I could) as well as learning through practice better makeup routines.
Along the way, my personality entered in when I considered the boundaries I faced when I was a serious cross dresser or transvestite. By nature, I always had pushed the boundaries of any thing I attempted. Once I thought I could do something above average, it was never good enough and I had to try to make it better. My whole attitude came from my parents pushing me along in life. I learned the hard way, nothing was ever good enough.
The whole process pushed me into going places I shouldn't have attempted as a novice transgender woman. Once I rejected going to the so-called "safe" gay venues, any other venue became fair game. Even though many times I was just going there to just see if I was presenting well enough to do it. The process led me to my well publicized times when I was formally asked to leave venues I shouldn't have tried to be in-in the first place. Once I learned what my venue boundaries were, most of my problems went away. Once I was able to dress the part and knew where to go, I was able for once to enjoy the process of living as a transgender woman away from the mirror in the world.
Just about the time I was becoming a little too satisfied with my progress in the world as my authentic self, I began to meet and gain friends. By doing so, I was able to progress farther and faster as a woman than I ever thought possible. I was able to watch and learn from them and just happened to have a wonderful time doing it. At the same time my friends were in essence were shielding me from potentially negative gender responses from the public, at the same time they were providing me a platform to learn and exist as a feminine person. I was enjoying the best of both worlds as I had the finest on the job training I could find.
By the time I had completed my on the job training as a transgender woman, I was ready to cast my boundaries aside and live my dream.
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