Gender Enablers

From the Jessie Hart Collection
Jessie (left), Nikki (Center), Kim (Right)

 Perhaps you had a special person or persons who helped you to open your own gender closet and take tentative steps into the real world. Perhaps you did it all yourself. In my case, after a very rocky beginning, I was fortunate  to have had several enablers to help me along in my transgender journey. My rocky beginning started when I enlisted the help of my first fiancé. After much convincing and begging I somehow convinced her to help me dress head to toe as a woman. 

My initial introduction to having a cis-woman make me up and help me dress turned out to have mixed results. I learned my fiancé didn't really have that much more skill than I had when it came to the art of makeup. Most likely because by this time in my life I had literally years of practice on my own face. Quite frankly, I was a little disappointed by the entire experience. Again it was because I had been trying and trying any new fashion accessory I could afford to help my feminine presentation along. Outside of the temporary thrill of having another woman provide instant feedback to how I looked, the entire experience lacked much fun or relaxation for me. The big problem which came about was not so long after this, she would attempt to use my cross dressing desires against me. 

For some unknown reason, my fiancé had a real paranoia about me going away to serve my country in the military. All the way to telling me if I didn't get out of my draft status by telling the military I was gay, she would leave me. To make a long story short, I wouldn't compound one lie with another by telling the military I was gay. So just before I signed up for three years in the Army, I graduated college and we broke up. Even though the whole experience was very painful at the time, it turned out to be one of the best moves of my life and she certainly was not one of my gender enablers. 

From then on I resolved myself to telling any potential serious relationships I was involved with that I was a transvestite as cross dressers were known back in those days. The whole idea worked well with my first two wives. As it turned out, my first wife was so mellow with the whole idea I think she would have not been surprised if one day I told her I was going back to where I served in Thailand but this time for a sex change operation. I was very close to doing whatever I wanted gender wise until I met and fell madly in love with my second wife who I write about all the time because we were together twenty five years until she suddenly passed away. Ironically, she was a gender dis-abler because she became dead set against any idea of me being transgender and beginning hormone replacement therapy. Through it all, we managed to stay together and I tried to learn from all the "tough gender love" she gave me. If she knew it or not. For example, she was the first one to tell me being a woman was much more than just looking like one. After yet another huge fight we had.

Following her death when I was free to start HRT and begin to seriously explore the feminine world, I was so fortunate to have found several serious gender enablers who helped me find my way in the world as a transgender woman. I have mentioned several times in the past several cis women lesbian friends who taught me so much about finding myself as a transgender woman. To this day I don't think they ever realized what all they did for me as my gender enablers.

Around the same time, I met my current wife Liz. Without a doubt she became my best gender enabler when she told me eleven years ago she never saw me as being anything but a woman. More importantly she encouraged me to grow into the out and proud transgender woman I am today. Even though the journey was rough and filled with tough times, destiny showed me the way to what I should have always known was true. I was just cross dressing as a man and biding time until my true feminine self could emerge.