Poor Executuion equals a Hot Mess

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 a short time to visit a few of my favorite venues and be back in time to remove all vestiges of my makeup and attempt to return to my male life. 

In the beginning, big mistakes would appear to ruin my time and turn it into a hot mess. I did not understand because I thought I was doing my best to put my new feminine cross dressed image to the public test. Some of my problems came from taking too many chances and others came from just purely being new to the world. Examples of taking a chance came when I used water balloons as breast forms, knowing full well how fragile they were. Predictably, one broke when I was out in public, making a huge mess in a rest room I was in. The only good thing which happened was, the room was empty except for me and I was able to clean up my mess and exit before anyone else came in.  From there, I learned the hard way to invest in silicone breast forms which I was able to use until I was able to grow my own breasts with gender affirming hormones. 

Other mistakes I would put under the title of ill-advised were the times I was simply having too good of a time and lost track of what time it was. Those were the evenings, I came home and ran directly into my second wife who was not amused. A huge fight always ensued until she settled down days or even weeks later. The whole process was not pleasant and just kept repeating itself essentially until just before she passed away. Finally I decided to purge my trans-feminization self and grew a beard for the last six months of her life. During this time, I didn't know she was as sick as she was and she passed totally unexpectedly and I often wondered if we could have stayed together for any length of time had she lived. All I do know was, I was making a hot mess out of our life because of my transgender issues. 

During this time also, I was desperately trying to catch up with all the small issues a woman has done to live her life. I did so many things such as wedging my heels in sidewalk cracks, which of course destroyed any image I was doing my best to project as a confident well dressed professional woman. 

Through it all, my wife still prodded me on by telling me I still didn't know anything about really being a woman. I wasn't able to learn until later how correct she was. My excuse is I wasn't allowed to play in the girl's sandbox until I earned it. I compare the process to being able to land a job by finally having all the qualifications needed. Until someone gives you the chance to move up, you have to earn your way or you never get the chance. I was always under qualified to play with the rest of the girls until I forced my way in.

Getting there wasn't easy. I needed to find a group of women I could learn from and not be judged at every turn. I also need to locate women who had no knowledge of my previous male self. He was never mentioned and most certainly, I never brought him up. When I did my life became so much easier. I did not have to worry about my transgender execution and hot messes became increasingly a part of my past.

Trans Girl Secrets

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 see the act of cross dressing in women's clothes to be an act of mental illness. 

What happened then was I needed to go into a dark secretive closet, I would not come out of completely for a half a century. Along the way, I included very few outsiders in my secret. Four or five to be exact. I did not even include myself in my secret. What I am referring to is the fact I wanted to do much more in my life than just cross dress as a girl, when in reality, the reverse was true. I was a woman cross dressing as a man the entire time and I was indeed transgender after all.

Predictably, one secret leads to another and another and in my case led to lies being told later on. My dishonesty came when I refused to admit to myself who I really was and took out my frustration on those closest to me. I became a very unpleasant person to be around when my gender dysphoria was at its worst. Even to the point of me losing a job because of what I was going through. It was like I was setting myself up for failure at every turn in my life as I waited for more and more people to discover my secret. 

The longer my secret was hidden away and on the other hand, I was desperately trying to discover a new feminine world as a transgender woman, the heavier my secret became. I attempted to hide all my transgender activities from my second wife and was reasonably successful. I say reasonably because I would do more and more as a trans woman until she caught me and the gender battle between us would continue. She was wiser than I was when at one point she told me to just leave her and live a life as a woman. That made her the second woman in my life who I should have listened to when they told me the same thing. The first was my gender therapist years before. 

Sadly, my male self was not ready to give up the strangle hold he had on my life and encouraged me to do the male thing and try to ignore and internalize all my struggles. Of course in the end run, the only thing which happened was the pressure just kept on building as I managed to keep my secret. However, no matter how hard my male self tried to protect his domain, he was slowly sliding down a cliff of no return. Finally, with the help of several close friends I made the gender leap of faith. I gave away all of my male clothes, started gender affirming hormones (HRT) and never looked back. 

Perhaps the best part of not having to protect my secret and not live a lie was my new friends never knew my old male self at all. My inner feminine soul was finally free to live her life. When she did, she became the third woman in my life to tell me the same thing.

The only secret I really ever had was I was never really a man at all. 

A Night at a Concert

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 date in downtown Cincinnati. I suggested stopping at a micro brewery for a quick appetizer when she wanted to go to an upscale steak house on my dime. I should have known then she was out of my league but I kept on trying anyhow. In a very short period of time, I told my daughter I was dating again. In response, she came up with two tickets to a local park pavilion near her house. The concert performer was Joe Cocker, so I could not wait to go. I even asked the new woman I was dating if she wanted to go and she initially said yes and the date was on, or so I thought. A couple days later and a week before the concert in the park, she called me and broke up our brief affair. I was slightly shocked but then again not so much as I began to consider what I would go with an extra ticket to see Joe. 

At the time, I was increasingly exploring the world as a transgender woman, so I thought why not take myself on a date in the park. I knew exactly what I would wear .My long silky black slacks with my black matching sleeveless top and black flats for comfortable walking. I then applied my makeup and topped my outfit off with my long black straight wig and I was ready for the half hour drive to the venue. By this time all of this happened, I was becoming very comfortable with my feminine self so I was really looking forward to the evening as it approached. I had spent many a evening being alone with myself. I wasn't very nervous as much as excited by the expectation of having a good time. 

The evening of the concert turned out to be ideal weather wise, a beautiful warm but not too humid Ohio summer evening. I showed my ticket and was admitted to the venue without a problem. Before I went to my seat, I decided to buy a drink and then headed to sit down. Again I experienced no problems with anyone in the venue in my section. I was able to enjoy my drink and relax even further before the music started. I especially enjoyed the silky sensation of my clothes in the summer evening air.

I was glad I went because I had been a Joe Cocker fan since the Woodstock concert days and it wasn't too long following the concert, he passed away and I was still able to be completely enjoy his performance before it was too late.

As far as I was concerned and as selfish as it may sound, the whole exciting evening was more fun for me than taking a woman I barely knew. Plus my experience even further increased my confidence as a novice transgender woman. Even to the point of coming out to my daughter who I told that I enjoyed the concert very much but never added who my "date" was. 

The night at the concert was one of those lifetime experiences I will never forget. It was the last time I ever tried to date as a man and the first time I was ever to seriously explore my life as a transgender woman. Once I did, the more I understood it was the life for me. 

It Has Never Been a Sprint

 

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 it. On the other hand, I was never a sprinter and a marathon was a closer match to my personality. Plus, there were milestones along the way which kept me going. Very early on, I knew I needed much more than just the feel of women's clothes to propel me forward. There just had to be more than just looking like a girl, I wanted to do more and be a girl. I knew the journey would be difficult and maybe impossible but I needed to keep trying. 

First of all, I needed to learn the basics of feminine appearance so I could safely explore the world as my new exciting self. With no help and very little money, I haunted the thrift stores trying different wardrobe items which were very inexpensive until I finally began to see improvement. My sprint during the time in my life when I was experimenting more and more was exhausting. The one thing which was evident to me was I was on my own. To win or lose was my passion but first I needed to see away around surviving a stint in the military where I could not express my feminine self. Fortunately, I could fall back on what my male self had taught me about internalizing my feelings. During my three years of military service, I managed to survive without cross dressing except for one notable Halloween party which led to me coming out to a few friends of mine as a transvestite. Included in the group of three was a woman who was to become my first wife and the mother of my only child. This brief sprint set the stage for me coming out to others in the future. 

For awhile, I was over confident about others accepting my authentic self until a conversation with my Mom brought me back down to earth. She soundly rejected me and I was off I pursuing my gender marathon again. Even with the set back, I had plenty of energy to move forward. Move forward I did, regardless of living with an unapproving wife. I needed to hide nearly all of what I was doing as I ran my next sprint. 

By this time, my sprints were becoming more defined as  I was increasingly discovering my dream of living a fulltime life as a transgender woman just could be a reality. Next up on my sprint were gender affirming hormones and making the decision to never look back where I had come from as a male and plan ahead a life as a transgender woman. 

The only constant I found on my gender marathon was change. Every time I thought I had it made in the process, something came along to disrupt my thinking. It could be as minor as being mis-gendered in the world or so much more now as I reach the twi-light of my life. Now making it to the finish line of my gender marathon in the best shape possible is my main goal.

Transgender Expectations

 

Picnic Image. My wife Liz on the right.

When I began the long and very difficult transgender journey I decided to take, I had many expectations.

At the time, I was still entranced with wearing all the pretty clothes a woman had access to. I could not wait to have my own wardrobe which would match any occasion from casual to formal. I was very naïve back in those days and thought a woman's life was all about how she looked. I was so wrong as I discovered as I explored more and more of a transgender woman's life. In addition to the layers cis-women went through in their lives, trans women face all of those and more. To begin with, we don't have the benefit of growing up around other girls and learning from them. Making our own way was difficult when the only input was coming from the mirror. 

Loneliness ruled my feminine side all the time my male side was trying his best to survive in the world he never really felt comfortable in. As I observed all the girls around me, my expectations of what their life was all about just increased. The problem was I had a distorted view of everything feminine. One example was I was shy and never liked having to ask a girl out on a date. I thought the whole process was so unfair just like worrying about serving in the military and getting shipped off to Vietnam. 

What I did not realize was the gender grass was not always greener on the feminine side. Was it easier to be the one asking someone out, or waiting for someone to ask you out. As far as the military went, there was nothing I could do about it, so I tried to hide my resentment and move on. 

As I did move on, I discovered many other expectations I never planned on. Communication was one of the major hurdles I needed to overcome before I could learn to live a quality life as a transgender woman. I was blindsided quickly when the public wanted to talk to me faster than I was ready to respond. Initially, before I went through vocal lessons, I tried to just talk in a soft background voice and hope for the best. Trying to match the voice to my appearance was not an expectation I planned on but it happened. It was just all a part of moving out of the mirror and into the world. 

As I matured as a trans woman and started to communicate with other women, I learned the grass was certainly not greener on the feminine side of gender. As I thought back to the Christmas envy I had because of my two girl cousins who were dressed in their new dresses and white tights. Liz ruined my illusions of pleasure when she told me stories of getting in trouble for getting her tights ruined by playing with the boys. 

Even though I found the grass was not greener on the other gender side, the more I learned of the gender differences I faced, the more I wanted to continue my journey. It seemed the more I experienced, I more I felt I had paid my dues as a transgender woman. More or less, as a rite of passage such as a mammogram. 

Since females are not born women but rather socialized into womanhood, transgender women have to go through the same process. By following all those expectations all those years, I finally arrived. The path I followed was difficult but in many ways the same as other women, transgender or not. 

Living in Your Own Prison

 

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 internet came along with social media, I was able to locate a few others who were cross dressers or transgender women , which made life a little easier in my prison. My biggest problem then became hiding my new on-line contacts from my wife who was more tech savvy than I was. Let's just say I needed to learn the hard way when my wife found a discussion I was having with a person in nearby Indiana and I had to become much too comfortable with.

Looking back, I could call the few, brief times when I tried to purge my feminine wardrobe and be a full time man as being out of my prison on parole. The problem was deep down I knew what I was doing was wrong and the pressure would build to build a new feminine wardrobe and try again in front of the mirror. I could almost predict when I would go back to my gender prison. 

Yet another casualty of me serving time in my closet was one I always mention, my mental health. Since it was already fragile and I was going to therapy for help, I didn't need any extra problems to push me closer to the edge.  I was becoming a hot mess as I took more and more chances when I left the house as my novice transgender self and explored the world. The problem became, I was feeling more and more natural when I escaped my prison. Even still, the process was not easy and involved too much scary trial experiences when I first went out. 

The entire process became all I thought about and when I was in my my male mode I caught myself thinking too much of the next time I was going to be able to experience life as a transgender woman. Plus, at the least I was busy studying the mannerisms of all the cis-women around me. I was locked in to one thing only and it was being a woman myself. It was a good thing I had my therapist to talk out my exploding feelings about my gender. 

I guess the only frustrating part of trying to explain to the outside world what it means to be transgender is there was no choice. If I would have continued in my self destructive male ways, I would have killed myself and become yet another statistic. Fortunately, destiny had other ideas for me when I escaped my gender prison and started to live an authentic life as a trans woman. Similar to so many others in the transgender community I was a survivor and thrived when I was free to do so. 

Bad Gender Decisions

 

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 makeup and clothes and it showed. I equated the whole makeup process to painting model cars when I was growing up. It took lots of practice to get the basics right. In the meantime, as I learned, many times I made bad decisions and came out looking like a clown. This was especially true with the clothes I chose to try to wear. I tried way too long to force my male body into clothes designed for sexy teenaged girls and I paid the price when the mirror lied to me and I tried to go out in the public's eye. 

When I was laughed at in public, I knew my feminine life had to change for the better if I was ever going to be able to survive. I just could not keep coming home in tears after another night out making bad decisions. Certainly. the process was not improving my deepening gender dysphoria. In desperation I sought out help from one of the only known gender therapists in Ohio at the time which was a good decision. The bad decision came when I decided to not listen to what she told me. She told me there was nothing she or I could do concerning my deep seated desire to be a woman. I would have to learn to live with it. If I had not been so hard headed and stubborn, I would have taken her advice and prepared myself for a life as a transgender woman. 

Once I started to really explore the feminine world, I made plenty of bad decisions. The primary example was when I became comfortable in presenting in places such as clothing stores, book stores and malls, I would always challenge myself to do new activities as a trans woman. Activities where I had to face the public and communicate one on one with the world. By doing so, I knew sooner or later I was going to have to challenge myself and use the women's restroom. Nature was calling and I knew I needed to answer the call. 

I started the process innocently enough by using the women's room in one of the bookstores I went to on a regular basis. I would do my best to make sure the room was empty before I went in and took care of my business. I was fortunate in that I read about and knew quite a few basics women follow when they gather in the restroom. I also knew from my experience in the restaurant/bar business women were not always the pristine gender they are known to be but that is another story. As well the other basics I needed to learn such as looking other women in the eye, washing my hands and stopping to adjust my hair and makeup. 

For the most part the only bad decisions I ever made as far as rest room usage was concerned was which rest room venue I decided to use. On a typical night, I would plan to go to my regular venues  plus maybe try out a new place. By this time, I was becoming fairly secure in my presentation to the point I wanted to try to challenge myself. I decided to go to a borderline redneck venue, order a couple of beers and try to use the restroom before I left. Before I knew it, someone had called the police on me and I was told to leave. Which had to be the worst decision I ever made. From there I went back to my usual regular venues and everything was back to normal.

Normal for me was difficult to change. I was so use to pushing my boundaries as a novice transgender woman, I had a difficult time adjusting my life when I no longer had to push so hard. I was enjoying the fact I did not have to face making bad gender decisions to begin with.

Are You Really Someone Else as a Trans Person?

 

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. To make matters worse, I even dreamed of being a pretty girl when I was asleep. Then I had to wake up confused and bitter when I found out life really hadn't changed and I was still a male after all. I needed to go again and challenge an unwanted world. 

Through it all, I often wondered why me? It took years for me to embrace who I really was and know the answer. I was just me and it would have to be good enough. However, the family upbringing I went through made it so difficult. During my youth, I was taught nothing was good enough. When I brought home any "B's: in my studies, they were not good enough. Where were the expected "A's." The never good enough attitude carried with me into my cross dressing life, all the way to when I became a novice transgender woman. In other words, when I acquired a new dress, when its newness wore off, I always felt I could look better in another dress, It led me to being a thrift store shop-a -holic. I couldn't wait until I could take what I had set aside money wise from my wife and use what time I could set aside to locate the next great outfit. 

My problem became especially bad when I was able to afford shopping for new wigs. I went through what I called my clown era of wigs before I settled into one or two wigs I wore all the time. By doing so, I was able to finally begin to build myself as a stable transgender woman in the world. I was beginning to learn I was someone else and that person was not a guy. 

As I was doing all of this  and as I lived a new and exciting world as a trans woman, I found I was taking all the stress off my mental health. The new authentic me enabled me to feel more confident on the gender path I was taking. I was fortunate also to have had a good therapist at the time to help me talk my way through it with her. Since I had previously been diagnosed as being Bi-Polar, both of us were careful to keep my gender issues separate. Plus, no mention was ever made of me being two people. I set the idea aside as being yet another mistaken idea from my youth. It could have been my male self attempting yet another move to survive the onslaught of life changing ideas which threatened his very existence. 

My life today proves I was always only one person and that was my feminine side. It is so sad I needed to fight so long to feminize my entire life as a transgender woman. The only true person I needed to be.  

Teamwork makes the Dreamwork as a Trans Woman

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 myself since by that time I had practiced in the mirror myself for years. The second reason I say sadly came years later when I was facing being drafted into the military and being sent off to Vietnam. At the time she pressed me to tell the draft board I was gay to be deferred from going. Even though I didn't and don't have anything against the gay community, I knew I wasn't gay and wasn't going to lie to escape military service. The end result was she ended up breaking the engagement when I went off to the Army which I learned later was the best thing which could have happened in my life to that point.

As you can tell, I didn't have anyone to enable my teamwork work from any sort of a dream work. One of the problems I was having was working my way through exactly what my gender dream. I was still years away from facing my reality of being a transgender woman. So I suffered alone with my gender dysphoria before I was able to break out of my gender closet. It wasn't until much later when I discovered the beneficial beauty of having cis-woman friends who accepted the new transgender me for who I was. When I let it happen, my dreamwork began to flourish. 

Quickly I began to learn the world from the aspect of being an invited participant in girls' nights out. I was invited along to several different groups of women. All the way from married women to younger girls still in the dating pool. Neither mattered to me because I was learning so much about living a women's life with no men around. Even though when I went out with the younger group, I found how it was to be the decidedly older and less attractive woman in the group. Again, it didn't matter as I flattered and happy to be invited to begin with. 

This was an exciting time of my life when all of a sudden my dream of living a life of a fulltime transgender woman seemed to be so reachable. Being included and  embraced by the women I met was the difference. We went to birthday dinners together, went to parties with each other and of course used the rest room together, All of which turned into the ultimate bonding experience as a new trans woman.

Was I scared? Sure I was but the embraces I received within the group quickly put me at ease so I could enjoy myself and gain confidence in the new feminine person I was creating. It turned out I did not have much creating to do because once my feminine soul hit the world, she flourished. 

Even still, being in a women's world and experiencing their teamwork, did make the dream work happen for me. I was a better person for it once I left my gender dysphoria behind. My mental health improved as well as everything else in my life once I left my male self behind.