Image from Nick Bolton on UnSplash.  Sometimes it seems as if closure to a transgender woman never comes. In the very early days in the mirror as I cross dressed, I thought I had reached closure when gender euphoria kicked in when I admired myself. It did until the pressure built to cross dress again and again. Predictably what happened was, I became so frustrated with the process of moving back and forth between the male and female binary genders, I decided to purge (throw away) all of my feminine belongings and go back to a male life. The problem was, deep down I knew purgi ..read more

Image from Author, Columbus, Ohio. More times than I would care to remember, evenings when I went out to explore the world as a cross dresser or novice transgender woman turned out to be a hot mess.  Particularly frustrating were the evenings or days when I thought I had planned everything out so well. I picked out the perfect outfit and applied my makeup just right and was ready to go. Perhaps my biggest issues had to do with figuring out where I was going to go and when I needed to be back before my wife returned home. Did I have a relatively long time to explore the world, or ..read more

Image from Ben White  on Unsplash. Secrets became a very important part of my life at a very young age. It all started when I viewed myself in women's clothes  in front of the mirror for the first time. I realized my life would never be the same again. Plus I also knew my desire to be a girl would not be well received by my family at all. It was in the late 1950's and early 1960's when cross dressing was still considered to be a crime where I lived near Dayton, Ohio. In those days any sort of gender dysphoria was thought to be a mental illness. Even then, I couldn't s ..read more

Image from the Jessie Hart Archives Following the time when my wife passed away, I actually tried to date another cis woman, once. During this brief period of my life, my old male self was still desperately hanging on to the idea he could still exist at all. At that time, one of my servers came into my restaurant with her very attractive Mother. After several inquiries I found her Mother was single and she would ask if she would go out with me. She did and we started our very short history of dating.  Right from the start I found she was a bit of a prima donna when we met on a ..read more

  Image from Marcus Spiske on UnSplash A transgender life is never a sprint, it is a marathon.  From the first time we slide on the hose and view ourselves in a mirror, we never believe the gender journey we have started would last as long as it did. Initially for me, I was on a very short term program when I would cross dress as a girl one day and live off the proverbial buzz until I could follow my dream and cross dress again.  I wonder now if I had known the journey I followed would have so many bumps in the road and would have lasted so long would I have still done ..read more

  Image from Engin Akyurt on UnSplash When someone says living a life as a transgender woman or trans man is a choice I get a huge chuckle.  I wish the people who think my life was a choice, needed to live a small time in my shoes and  then they could truly decide my life was never a choice. I was living in my gender prison. In many ways, I could describe my confines to a bigger version of what was called my personal closet. Either way, I was stuck in a very dark and isolated space where I was all alone. Especially in the pre-internet days when I was living. When the i ..read more

  Image from unknown origin.  I often wonder if during all the writings I do, as I  describe how I succeeded in living my dream as a transgender woman, do I emphasize the bad decisions I made.  Needless to say, I made plenty of choices I wished I had back to try again. First of all, I suffered from the same problems nearly all novice cross dressers or transgender women go through. Unlike cis gender girls our age, we didn't have the peer pressure or knowledge to help us be girls or women. We were not invited to the sleepovers where the girls experimented with makeu ..read more

  Image from Kevin Laminto  on UnSplash For the longest time, I considered the idea I was two separate people. On one hand, I was living the male life I was entrenched in and on the other, I was attempting to carve out the precious time I needed to explore my cross dressing self in front of the mirror. Trying to live a life on the gender border between male and female as very difficult to say the least. When I was in male mode, I spent every spare moment wanting to cross dress again at the least and trying to imagine what living as a girl would be like the rest of the time ..read more

Girls Night Out, I am on the bottom far left. Similar to so many other cross dressers or novice transgender women I have heard from, they dream of enlisting a cis-woman to aid in their appearance. I was included in having a similar fantasy. All the way to the point of begging my fiancé to completely dress me as a woman if I rented an out of the way motel room for privacy. Sadly, for me, she agreed and she did do her best to dress me as the woman of my dreams.  I say sadly for two reasons. The first being I did not see that much of an improvement over what I was able to do for m ..read more

  Civil War Cemetery image from the Jessie Hart Archives   In my life I have found several really rare times where true opportunity actually knocked on my door.  As I indicated, the situations were exceedingly rare and required split second decisions on how I was going to proceed. Possibly the first main one happened when I went with the "A" list trans women from the cross dresser - transgender mixer I was at in Cleveland. It was the night I gathered my courage, put on my big girl panties and was able to enjoy a professional makeover at the mixer. The result was I look ..read more