Transgender Vacation Blues

 

Image 
from UnSplash 

Back when my second wife was still alive, in the early fall or late summer we used to vacation close to the same area every year. 

We used to just take off and travel from our home in Southern Ohio and make the trip up through Toledo and Detroit up into northern Michigan. Often trying to escape the late summer heat, we went as far North as the Upper Peninsula of Michigan. It was a great time to go because many upscale venues in places such as Traverse City discounted their prices for off season tourists and we didn't have crowds to deal with. 

During that portion of my life, things should have been going good. My restoration efforts on our 1860's brick home, were coming together and both my wife and I enjoyed jobs which provided us with a little spendable income. What could possibly go wrong? In reality, just one major one. My battle with gender dysphoria. I was just beginning to experience more success as a novice public cross dresser and or transvestite and I wanted to do more. I was also riding the waves of gender euphoria when I went out and gender repression when I couldn't. Part time exploration of my transgender needs just wasn't working. 

It figured then, if I wasn't able to try to experience my gender euphoria just before we went on vacation, most certainly I would mentally crash and burn during our vacation. Of course when I did I would grow grumpy to the point where my wife would ask me what was wrong. She would ask what else I needed in life to be happy. At that point I just couldn't tell her the truth. The only thing which would have made me happier at that moment was if I was making the vacation trip as a transgender woman. From then on I did the usual male response and internalized my feelings and acted as if I was feeling better.

Sadly my gender dysphoria managed to ruin several vacations for me as time after time I fell into bouts of gender depression. I was even affected when we made our annual stop in the village of Frankenmuth, Michigan to look for rare Christmas tree ornaments my wife didn't already have since she was a Christmas fanatic. I over compensated by encouraging her to over buy every year. As we walked through the stores, no matter what I was outwardly feeling, inwardly I wanted to be doing it with her as two girlfriends. Naturally, the entire process ruined the vacation time I should have been enjoying.  I had the vacation blues which at times frustrated me even more because I should have been enjoying my hard earned time away from my pressure packed job.

Since I never had the courage to face my transgender truths until much later in life, my vacation blues never changed until I retired and met Liz, my current wife. The vacations we have taken changed the vacation narrative for me. The blues have disappeared and for once I have been able to enjoy myself. . 

Deep Gender Frustration

My attempt at formality.
From the Jessie Hart Archives.

One of the first deep seated internal  frustrations I felt with my gender dysphoria was when I first encountered the challenge of attending my junior-senior prom in high school. 

I was very shy and nervous when it came to being around girls of any type. I didn't have any sisters or any girls in the neighborhood I grew up in, so I had no experience. When I made it to the time when my first prom came up in my junior year, I was stuck in a new high school with very few friends period. Especially no female ones. So I had no one to even summon up the courage to invite to the prom. It turned out, the problem was going to take care of itself without much effort on my part. 

What happened was a group or clique of popular girls noticed one of their group did not have a date to the prom. At that point, they reached out to me to find out if I was interested in attending the event. I nervously said yes and the planning began. Little did I know what I was getting into. As the male part of the date (back in those days) I was expected to provide everything from transportation, to dinner to flowers for my date.  My deep problem was I was the one who wanted to wear the fancy gown and be given a corsage then dined and danced with. I was deeply frustrated. The only good parts of the entire night were my parents were proud and probably a little relieved I was finally going out with a girl. On my part I was interested to see how I would finally find out how I would react to a real live date.

As predicted, my first prom did absolutely nothing to relieve any of my deep seated gender frustrations. In many ways, the whole process just made it worse. At  the least at that point I had began the process of learning what dating a girl was all about. In my senior year I actually met and stayed with another girl until I went away to college. The time included another prom in my senior year which I needed to suffer through since once again I wanted to be the girl, not the guy. I hated the tuxedo I had to wear all the way (again) to not being the one in the glitzy dress. The only revenge I ever received came years later, the supper club we went to eat at prom became a large gay venue and I was able to use the same women's room my date used. A small amount of retribution but meaningful none the less.  

When I went way to college, the initial months on campus provided one of the few gender respites I ever experienced from my transgender life. But to make a long story short (as you know) my desires to love everything feminine never went away. In fact, years later my jealousy re-surfaced in a major way. During my years working for a major restaurant chain franchisee, the company threw lavish Christmas parties for the store managers and upper level assistants.  The parties were semi formal  so once again I was thrown in to being downright jealous of the women who would be attending. Several were very attractive and needed to try to negotiate getting in and out of the limousine the company provided  for transportation in the fancy gowns. As the other men admired the women and their attempts to stay modest when they entered and exited the limo, I on the other hand, wanted to be one of the women in the beautiful dresses. 

It wasn't until fairly recently when I came even remotely close to achieving close to the same feeling cis-women feel when they are able to dress up. During recent Christmas's and other banquets I have managed to come up with a semi formal dress up look. It provided me a respite from a little of the gender frustration  I experienced over the years.  I also discovered women all along were aware of their own insecurities of semi formal events. Often the grass is not always greener on the other side of the gender fence. 

Code Red Moment

Image from Alexander Grey
on UnSplash

I remember like is was yesterday the night years ago when my life changed forever.

It was the evening when I decided to journey out in the world as a transgender woman for the first time instead of just trying to get by as a cross dresser or transvestite. I knew I was playing with labels but the whole process was important to me. 

First, I was so terrified I would fail and be subjected to more of the public ridicule I had experienced in my recent past. Even though I was relatively a novice in trying to present responsibly as a woman in front of the world, I still knew I had to make a concerted effort to do my best to blend in with the other women I would be facing when I went out. 

I chose where I wanted to go carefully. I knew that every night around eight or nine o'clock many single women would gather at a TGIF Fridays after work at a nearby upscale mall where they worked. If you are not familiar with a Friday's, it was one of the first venue's to welcome and provide a safe environment for single women in the country. 

Up to that time, my gender life was similar to riding a "teeter totter" on a kids playground. One day I was up with gender euphoria but the next day I was in the depths of my gender dysphoria. Desperately trying to find a way out until the "teeter totter" reversed and moved up again. The process dominated my life and made it very difficult to lead a so called normal life. 

On the night in question, I was determined to make a statement and help my gender euphoria. I began by picking out a fashionable black pants suit I had found in my size at a local thrift store and paired it with a sensible pair of women's flats they might wear following a long day in heels on the job. I applied my best makeup and longish blond wig and I thought I was ready to attack the world...or at least a small portion of it. To top it all off, my anxiety level was at an all time high as I traveled the twenty five minute trip to arrive at the venue. Once I did arrive I think I must have spent twenty minutes in my car trying to calm my nerves before I gathered enough courage to go in. I think my male self was becoming frightened the beginning of the end was coming for him.

As I went in, I had a small amount of knowledge on the venue I was going to. In addition to my wife and I going there, I had worked for a chain of competing venues for several years. So, I knew, if I could get past the hostess stand in good shape and secure a seat at the bar (if one was available) I had a chance of succeeding. When I did all of that and was able to breathe again, I was actually able to relax and enjoy myself and then start thinking I was in a "Code Red" lifetime moment. Deep down I knew, my life could never be the same again as I had arrived on the successful threshold of being a full time transgender woman. My male self was aware to he was in deep trouble.

From that moment forward I was able to go back to the Fridays and establish myself as some sort of a regular. Even though I never thought I presented completely as a cis-woman, I knew I was easy to remember. Back in those days, transgender women and men were just becoming slightly better known in the world. In addition I never caused any trouble and tipped well. In a couple places where I became a regular I even think the venue valued my business as a sign of their diversity.    

Whatever the case, the code red had occurred and the teeter totter began to stay in the upward position which meant my old male self was never coming back.