My Last Date...as A Man

 

Long Dark Haired Wig Look
From the Jessie Hart 
Archives.

In many ways this was the final straw in my attempt to live in a male world. Approximately two years following the passing of my wife, I had the opportunity to date the Mother of one of my servers. She was smart, single ( near my age ) and very attractive. If I was a "real" man, she was the ideal woman I had ever wanted. As always, I realized nothing had really changed with my gender issues when it came to dating other women. Still I went ahead and tried and succeeded on setting up a few dates.

Along the way, we went on dates to places such as the Frank Lloyd Wright designed home in Springfield, Ohio all the way to a company sponsored suite at a Cincinnati Reds professional baseball game. Seemingly we were moving along at an reasonable rate until she sprung the question on me which probably ended it all. She asked me what my deceased wife would say about the situation I was in life without her.  I fired off the answer I drove her to an early grave without thinking of the consequences. Even though essentially I told the truth, I didn't immediately realize my future days with her were numbered. Obviously I decided not to mention any of my gender issues as probably added to the extreme stress of my wife's life.  

Through it all, my daughter had monitored my return to the dating field with some interest and at that time I hadn't come out to her as a transgender woman yet. As a gift she gave me two tickets to the late Joe Cocker who was performing at a nearby outdoor venue. I immediately took the opportunity to invite my new friend to join me. Initially she said yes and I thought all was good. Then about three or four days later she abruptly called me and said she wanted to end all dealings with me. I was shocked and said goodbye forever. Then I had to decide who I would invite to go with me to the concert.. Fairly quickly i decided I only knew one other woman well enough to invite and that was me. It was a great opportunity to judge how well I could present in a totally different situation. 

First I had to come up with a proper wardrobe choice which would blend in with a probable slightly upscale audience. For the evening I chose my black slinky wide legged slacks along with a black sleeveless top. The outfit was one of the benefits of having nearly hairless arms. By this time, I had arrived at a point where I didn't have to worry anymore what people may think of me for having hairless arms when I was still presenting as a man. For the evening I selected my long black straight haired wig to go with comfortable flats and sensible makeup to fit in. 

To my knowledge, all went well during the concert. Nobody gave me an extra glance and I was able to enjoy a cocktail as well as the concert. I ended up being one of the better dates I had ever had. A fitting end to my often discouraging history of my dating as a man. Something it turned out I never wanted to do anyway.  

When I transitioned to a transgender woman and was dating women such as my future wife Liz, I relaxed and was finally able to enjoy a new and wonderful life. The entire process was similar to everything else I had discovered about myself. Living a gender lie was never easy or successful, My last date as a man just proved it again.

Transition within a Transition

For someone who has never followed a gender path to their authentic selves, they don't realize  the path

Nesting Dolls

includes many different separate transitions. Once I began to think about it, I started to equate it with a set of Russian Nesting Dolls.

The first major transition I went through was when I realized just living in the mirror looking like a girl was not enough. After the feeling of exhilaration or gender euphoria quickly faded, the true desire to actually be a girl remained. You could say I was going through the earliest realization I wasn't a cross dresser at all. My gender issues went much deeper than just dressing like a girl. I was similar to the smallest nesting doll in the picture.

As I began to follow my new gender path in life which always reminded me deep down I should have been a girl, I desperately needed to find ways to satisfy my urges. Sadly the entire process wasn't the smoothest and led me to the point of desperation when I faced the fact I would not see the light of day as my feminine self except once a year at Halloween. I compare it to being doll number five in the set. the more I learned about my feminine side, the more I wanted to learn. which included getting out into the world and escaping my mirror and very dark confining closet.

Once I began to get out of my closet, there was no going back. I began to quickly move to the bigger nesting dolls following successful journeys into the world as a novice transgender woman. Slowly and very unsurely I found my way into ever larger gender challenges.  To me the fourth nesting doll from the top represents the times I had to learn to communicate with other women and men in this brave new gender world. I was trying to make my way without any of the old male privilege's I had built up over the years. Looking back, I'm lucky I didn't break this fragile doll.  Many times during this period of my life, I thought I had it made to some extent but I didn't realize how much farther I had to go. I thought the biggest dolls would be the easiest to obtain.

Surprise, they weren't. I view the second to biggest doll as when I started hormone replacement therapy. HRT provided me with the chance to improve my external appearance as well as opened my internal self to a new softening I never thought possible. All in all my second doll provided me with all I needed to know to move forward to the biggest doll. The biggest doll was my ultimate goal of living full time as a transgender woman. 

I managed so far to find my largest Russian  nesting doll and not break it. I survived many gender transitions within a transition and I am happy for it.

Transgender Fear versus Ignorance

Ohio State Student Union
Jessie Hart Archives

 Often I think all the right wing attacks in our country and elsewhere come from fear of what a transgender woman or trans man can bring to the table. After all we have had the opportunity to experience the two primary binary genders from both the male and female perspectives. Some people have a tendency to become uneasy when you have the possibility of knowing just a little too much of where they are coming from personality wise. Others carry very little self esteem and are always looking for the slightest edge when it comes to thinking they are better than someone else. I perceive many "TERF's" as suffering from gender insecurities normally reserved for men. "TERF's" by the way are Trans Exclusionary Radical Feminist's. 

Perhaps the radical feminist's are fearful transgender women will find out too well how it is to be a woman and have access to too many feminine privileges. I have been fortunate in that my personal dealings with TERF's has been fairly rare. Going back several years ago when I was asked at a lesbian Valentine's Day dance what my real name was, all the way to being refused acceptance into my wife Liz's lesbian social club. Which she promptly left. 

I looked at the groups refusal to accept me as pure ignorance and nothing more.  These days though I perceive all anti-transgender rhetoric is mostly fear based in where it comes from. How could we trans folks have the courage to live as our authentic selves when others in the world are stuck in their mundane existence. Plus, as I have mentioned before, gender all by itself is a powerful force. So much so, many parents are afraid to discuss it with their children. They would rather take extreme measures such as banning books on the subject from schools and libraries. All stemming from a deep seated ignorance of the subject. Since the number of true transgender women or men is a small portion of the overall population, very few people ever have the chance to meet and know a trans person and realize we are not much different than the average person.

Then there are the drag queens who all of the sudden became threatened with all this far reaching anti-LGBT legislation. Once again it seems in some circles, transgender women are being mistaken for drag queens. Or vice versa. We will see how a few of the smug seemingly protected cis gay males take it when their rights come into question again. If motivated, they can bring at the least, monetary resources to help with the upcoming battles. 

Maybe I am making too much of the fear aspect out of all of this. In many circumstances fear comes from ignorance on a subject. The only way around all the ignorance is education. I consider being able to be out and proud with my authentic life is a blessing. Hopefully I will be able to help those coming behind me with my actions.