The Long Dark Transgender Tunnel

Image Courtesy Snowcat
on Unsplash

 Recently I was thinking of how I actually transitioned twice in my gender life. For over fifty years I considered myself a cross dresser. In fact, for the longest time I considered dressing as a woman to be a harmless hobby. Obviously the longer I went along, the more I discovered it was anything but a hobby and far from harmless. All the time I spent agonizing over my gender issues proved to be very self destructive. In other words, I spent countless hours wondering what gender I was becoming and what I would do the next time I had a chance to dress in my secret feminine attire and admire myself. This stage of my life essentially lasted from when I was ten-ish until I was sixty and finally decided to begin my second serious gender transition. Although I can safely say I knew I was experiencing gender issues way before the age of ten. 

Of course I am aware no one can reclaim time but I do try to learn from all of my positive and negative experiences. Initially, I was able to install lights in my transgender tunnel which would allow me to learn the basics of makeup and how to dress myself. I stumbled when I went through my girlish high school years when I was in my thirties. Those were the days I committed the usual cross dresser sins such as trying to dress too sexy which turned out to be a trashy attempt to disguise my testosterone poisoned male body in clothes designed for an attractive teen girl. Needless to say, those were difficult days for me in my tunnel when the light at the end always seemed to be the train.

Fifty years is a long time and still I persisted and more importantly learned what I needed to do to better prepare my feminine self to go public. I can compare the process to enabling my strong inner female to take control of the process. Approximately it was this time I went into what I called my business professional period of my life. An example was when I would dress up as my best impression of an executive woman and shop all of the upscale malls back in the day when many of them flourished and so did I. Rarely did I experience any issues as I shopped. One of my favorite outfits I acquired was a pale, pastel green suit with a short skirt which I paired with pastel green opaque panty hose and kitten heels. I topped it all with my shoulder length blond wig and was ready to explore the world as a woman. What a relief it was when my feminine life was starting to come together. But the biggest problem became, now what? I knew the light at the end of the tunnel wasn't the train but something different. However, the closer I became to the light at the end of the tunnel, I knew I felt too natural to ever return to my unwanted male existence. He was fading away.

As I said, I ended up following the light in my transgender tunnel and decided to transition for a second time. This time I decided to never look back and begin hormone replacement therapy. From that point forward I was going to not only leave my long tunnel behind but I was going to allow my inner feminine self to find her way in the world. A possibility I am sure she never thought was going to happen. Once I did relinquish control, my feminine self made certain I knew it was her providing the light in my transgender tunnel. The light was very dim in the beginning but became brighter the farther I went.

The big question I have now is why was I so stubborn in hanging on to what was left of my male ways.  Even though all of my male life wasn't miserable, I think after my daughter was born I could have left the remainder of him in the past. I could have said then I was a cross dresser for twenty years instead of fifty. 

For any number of reasons none of it happened and I continued down my long dark transgender tunnel much longer than I should have.    

It Takes a Village

Virginia Prince in 
the 1940's

 I am sure over the years you have heard the term "It takes a village" to describe the best way to raise a child. I think the phrase is especially true when it comes to negotiating a gender transition. You regular readers know how often I mention the lack of transgender mentors we had as we each tried our best to cross the binary gender divide. As with most of you in the same senior age category I am in, mutual contacts were very difficult to come by. 

Fortunately later in life, my contact group expanded and I was able to take advantage of my new peer group. It all started with me when I discovered "Virginia Prince" and her "Transvestia" magazine. As I remember, it was published every two months and I couldn't wait to receive my new edition. Of primary importance to me were the announcements of regional transvestite "mixers". One of which was within driving distance to me where I lived in Ohio. Naturally, I couldn't wait to attend one of the mixers if I could get the trip approved by my wife. Finally she went along with the idea and she even helped me to try to pick out an outfit to wear. 

Regardless of our disagreements on what I thought I should wear versus her ideas, I went and I learned. Most likely the biggest lesson I learned was the different layers and types of the other attendees I met. Every layer from the so called beautiful mean girls to the overtly masculine cross dressers and me in between. I just didn't feel comfortable in either group. 

It wasn't until much later in life I finally discovered why. When the transgender term was introduced, I knew then I discovered an idea I could identify with. I felt that surgery wasn't the driving force in my quest to live a feminine existence but the mere fact of being able to live as my authentic self was. And the authentic self proved to be my inner woman. 

During her path to the surface, she received quite a bit of help. It took the village I mentioned to enable her to finally break free. I don't mention enough the group of cis women who embraced me when I came out of my gender closet. Then, after the first group, there was a second circle (as I like to call them) who helped me solidify my new life and move on. I will mention them more in another blog post. 

In the meantime, even though it took me years to realize it, a village was welcome and needed for me to find my way to a life I really wanted to lead. As a full time transgender woman. 

Transgender Teamwork

"Shawna Wegner" is fighting a proposed bill in Arkansas which would force transgender women and trans men to use the restroom which was originally listed on their birth certificate. Now you can sign a petition to fight back. Every signature counts.

 No matter where you live, legislative bills such as this ultimately threaten our very existence. Please go here to add your name! 

Thanks!!!!

Dream on Or Transgender Dreams

Image from Randy Tarampi on
Unsplash

 I am fortunate, rarely do I suffer from not being able to sleep. Normally do I not benefit from my eight hours of slumber. Some nights it is even very entertaining. 

Early in life I remember vividly the mornings I would wake up from dreams in which I was a girl. I was immediately disappointed to learn  nothing had changed with my gender. I wasn't the girl of my dreams. Sadly for me my girl dreams were vastly outnumbered by my numerous boring male dreams. These days, following living forcibly as a male for sixty years, my nightly experiences are becoming more mixed according to gender. I guess the more I spend time as a transgender woman the more my subconscious mind is accepting it and is beginning to build a backlog of experiences of me in a feminine world. 

These days, I have made it to to a wonderful mix of gender dreams when I would have one dream as a man and the very next as a woman. Now interestingly I have reached the stage of being a cross dresser. Often I have to go through being exposed as a man in a dress and subjected to the normal rejection by the public. Perhaps I am just reliving the time in my life when I was coming out of my hidden feminine shell. Often to the stares and outright laughter at the hands of an ignorant public. 

Through it all, I am still dazzled by my subconscious which is able to switch my genders at will and put me in impossible situations in either. An example was the night, I started by dreaming of running a perfect shift during a very busy night at a restaurant I was running then going to a time when I was wearing a dress which was too short. To the point I was embarrassed and was trying to cover up my bare legs. 

I wonder if I live long enough, if my time as a transgender woman will overtake my time as a man. Which will be tough to do since to equal experiences out I would have to be one hundred twenty years old. Perhaps what will make up for the difference in years will be the intensity of the experiences I have been living through. Perhaps all the years of learning to find myself as a transgender woman will come back in my dreams. It will be interesting to find out. 

Using my very weak mathematical skills, I have calculated I spend approximately one third of my life sleeping. Since I do, I hope my dreams stay interesting. They remind of a rich life I have been able to live. One as part of the male gender I never wanted and the other as part of the female gender I always wanted to be included in. More examples of living as my authentic self will be welcome as reminders of my old unwanted male self fade away. Finally my transgender dreams will triumph as well as I have triumphed in my gender wars in real life.  

Transgender Safe Spaces

This afternoon is my oldest grandson's birthday party/dinner. Without hesitation, my wife Liz and I said we would attend. Not so long ago, my response would not have been so quick or so easy. Similar to so many of you transgender women and trans men, I went through significant stress finding a safe place to go to and explore the limits of my new authentic self. 

Photo from the 
Jessie Hart Archives

The first venues I tried were the primarily gay bars where I discovered quickly I really wasn't welcomed. After all the vast majority of the gay men in the space were looking for other men and only viewed me as another drag queen. If there wasn't a drag show scheduled for the night I was there, I was totally out of place. It did not take me long to seek out other so called safe spaces where I could attempt to learn to live my new life. 

A few of the venues I chose did turn out to be safe while others not so much. First I tried a couple of small lesbian bars I discovered in the Dayton, Ohio area. Both were former biker bars. One maintained that image for lesbians While the other was certainly more mellow and welcoming. The first place always made sure I never felt welcome while the other was the opposite. Primarily because it turned out my male self knew one of the bartenders. The only problem I ever ran into in the second venue was when I was forced into singing karaoke by a very masculine lesbian. I don't sing at all, so it was quite the challenge. It wasn't so long after that the place closed for good and I was forced to find other safe spaces to go to.

Since I was already the general manager of a very popular and busy casual dining bar/restaurant, I knew with some certainty what I could do to develop another safe space or two to go to. I found I was successful in locating a couple and decidedly not successful in trying to become a regular at others. So much so, I had the police called on me when I tried to use the restroom. I easily explained my situation to the cops and was sent on my way. I did manage to become a regular at three other sports bar type restaurants and even received rest room privilege's in the process. Plus when I finally established myself with a small group of friends I came with, I became ever more of a regular. I enjoyed my space spaces immeasurably and was able to grow my feminine self. 

Outside of a couple isolated instances, I never went back to the gay venues again. Where I never did really fit in. 

As far as my daughter's in laws were concerned, I write often concerning how accepted I was as a transgender woman. I think I was more concerned about how I would be treated than they were. After all I was carrying a ton of my old macho male baggage with me. Plus, speaking of safe spaces, I would be remis not mentioning all the current concern over a pre opt transgender woman in a woman's locker room without any clothes, I don't believe it's time for  any real input from me  Except from saying personally, I wouldn't want to show off my naked body in either locker room and I can't imagine someone doing it without backlash. Also, as a transgender community, we don't need any potential negative publicity. 

On a brighter note, I hope you all have found and developed your own transgender safe spaces.  

You Wanna be my Girl

 During my errands this morning, I heard the "Jet" song "Do you Wanna be my Girl." If you aren't familiar, the lead singer mentions his lust interest in the song as having long blond hair and long legs. Back in the day, I tried my best to look the same way as I wore my skirts too short and matched them with a long blond wig. Through it all, I certainly wasn't having any music written about me. Ironically I was doing all the wrong things fashion wise as I supposedly didn't want to attract any attention and blend in with the world. My problem was I was presenting to attract men and not blend in with the other women around me. 

Girls Night Out from the Jessie Hart Collection
I'm seated in Stripes on Left

As I look back at my life, I see how often and desperately I wanted to be my own girl. Way back in high school after I was turned down yet again asking a girl on a date, I would run home and if possible shave my legs, put on a pair of pantyhose , apply makeup and finish dressing as my favorite girl...me. I always knew she wouldn't turn me down. This continued through out my life until the Army briefly forced my male self  to stand up and be counted. That didn't continue long because my dominant feminine self was always waiting patiently and often not so patiently to live her life in the public's eye. Not only I found did she want to be my girl, she wanted to be "the girl". 

Being "the girl" turned out to be the best move I could make. The big differences came as I was coming out of my gender closet and into the world. Instead of feeling terrified, I felt excited and so natural I couldn't wait to do more to achieve my inner woman's goals of coming out. As I quickly learned, when I got out of her way, she knew who she was and developed quickly. So much so, she was slowly but surely pushing my wife of twenty five years out of the marriage.  

Sadly the only thing which saved the marriage as long as it did was her untimely, sudden death from a heart attack at the age of fifty. Often before she passed, we had a dog who was certainly a one person dog and the person was me. My wife always said if something happened to her, the dog would never miss her. Which is very close to what happened. What also occurred was when she passed, the door was suddenly opened for my feminine self to come out. In many ways it seemed she had waited long enough for her turn and here it was. Even though the entire experience was and is a total shock to my being and I loved my wife dearly, I knew the path was clear to my gender freedom. At my age of sixty I was in a position to take the gender leap to freedom and not look back. All of a sudden, I didn't know how much time I had left as I lost more and more of my closest friends to cancer. 

The answer was clear, I wanted to be my girl. Even though I knew there were going to be many more bridges to cross and some even to burn. I was given a second chance in life I just couldn't turn down. 

A Gender Threat?

Photo Courtesy Linkedin

Recently I wrote a post concerning a communication with the public as a new transgender woman. When I did the gender transition, I did it and surprisingly learned I could communicate with women better than I ever had before. After reading the post, Paula from "Paula's Place" blog, checked in with this comment:

"  I have actually found it easier to engage with strangers as a woman than I ever did when the world was experiencing me as a man. Being seen as man often equates to being seen as a threat. Being seen as a woman I am "safe" I can now indulge in the casual conversations with strangers that used to annoy me so much when my Mother did it." 

Thanks for the comment! I agree being seen as a man does equal being seen as some sort of a threat. Plus, there is also the sexuality facet which needs discussed. How many men want to approach a woman from a sexual aspect. Women on the other hand, especially attractive ones have grown up suspecting men because all they want is sex. Or men too, appreciate the chase of a woman and grow restless after they have "won" the "battle" for the woman they were approaching. During my dating years, I was most likely too timid in my approach to women. I didn't want them to think I was only into them for the sex. When in reality I just wanted to be just like them. I wanted to be the hunted not the hunter in a relationship. I thought life would be so much easier if for once a girl would have to ask me out, rather than me going through the torture and the nerves asking a girl out. As you can guess, I was often rejected and most of the dates I went out on were set ups by friends. Actually having a date on my arm helped solidify my standing in the guy community. The date went right along with me driving the best car I could and playing as many sports as possible. All of which were covering up my deepest, darkest secret. All I wanted was to be a girl. 

When we cross the gender frontier and earn the chance to have casual conversations with other women, as Paula said we essentially learned a lesson in gender communication. We are now "safe" and have escaped the rigid boundaries of gender discussion. It is no longer forbidden to compliment another woman on the simplest thing such as her earrings. I learned very early, a simple compliment could open the door to knowing another woman so much better. The more we talked, the more I learned about what the other woman may be thinking about me being transgender. 

The only time (and it was rare) I was perceived as some sort of a threat was when another woman's man entered the picture. I said it was rare because most all men had the tendency to leave me alone. It was when they didn't, the claws began to come out and I had to retreat. As far as I knew her man was just being friendly and was attempting to insert himself into our feminine communication which Paula alluded to. 

Sadly in this day and age women of all types are being subjected to more gender threats. If and when a transgender woman achieves a completely passable image, then she is faced with "surprising" a so called unsuspecting man. Violence could follow which leads to the very high rate of transgender murders. Very luckily in my case I was able to nearly avoid brushes with violence when I lost my male privilege of safety. I learned the hard way and was able to move on unscathed. I was neither the hunter anymore or the hunted. I wasn't a gender threat and it opened many doors I never expected to see behind. The trip was worth it. 

It Was a Team Trans Effort

Overall I have written several times on how a journey down a transgender path can be a very lonely experience. At a very early age we trans youth find we are on our own. We don't even have the benefit of peer influences to shape our path in areas such as make up and clothing. Especially in the pre internet days, our gender closets were very dark and lonely indeed. Because of all of that, many of us desperately wanted an understanding cis-woman to help us with our transition, mostly in the appearance department. In my case I found just because a woman I knew would help me with my makeup and clothes it did not mean she had any real expertise to help me. In fact, the first person to really help me with makeup advice was a male makeup artist at a transvestite mixer I attended. He worked miracles with me and even explained what he was doing so I could repeat the process myself. I went on to help my second wife with her make up on numerous occasions because I actually wore more make up than she did. 

Later on in life, when I seriously began to explore being a feminine person in the public's eye did I begin to find the peer support from other women who helped me transition into the person I am today. They have been so important to me over the years that every now and then I mention them here in the blog. 

Photo Courtesy Rachel

Along the way I received advice on buying a banana from Amy to practice how to pleasure a man all the way to a constant reinforcement that I belonged in the world as a woman from people such as Kim and Nikki. Who had very little to do with men at all. The experiences such as lesbian mixers all the way to woman's roller blade events were priceless learning sessions. Of course I wasn't accepted by everyone but  since I had my core of supporting friends around me, no one else mattered. In other words, my life experiences back then taught me the boundaries of what I could and shouldn't do. For the most part I had a great time as I had in depth lessons on how to blend in with a new terrifying yet exciting feminine world. 

As you can see, I was blessed with having a total supportive transgender team around me including a couple more people I can't leave out.  Rachel was another transgender woman I partied with often. She was the one who told me I passed out of sheer confidence. Which I always took to mean even if I was not the prettiest trans girl in the room, I was not going to let it stop me from living an authentic life. The other person who was so very instrumental in my MtF gender transition was my wife Liz. Eleven years ago she told me she had never seen anyone but a woman in me and I should quit straddling  the gender fence and start living full time as a woman. 

After such a slow lonely start, it was a total team effort for me to become the person I am today. I have been fortunate to have had so much help.

Engaging the Public

 Engaging the public as a transgender woman has always been difficult for me.  First of all, I am an inherently shy person  and secondly when I first reached a level of coming out as my feminine self, I had to begin to communicate with the general public. All of this added to me being increasingly shy. 

Photo from the Jessie Hart
Archives

For some unknown reason, this morning was different. Since my retirement, I especially don't like to get up early in the morning. But as a favor to my wife Liz, I got up at 5:30 AM to go with her to a doctors appointment which was a half an hour away. As bribery, I made sure Liz knew we would have to stop for breakfast at a certain fast food place we enjoy. Plus we had to hurry because she had to be back as soon as possible to sign in to work which she does from home. 

In addition to getting up so early, we arrived fifteen minutes early and we had to wait in the outer hallway for the office to open. As we were standing there, a man came by with a crock pot full of some sort of food. I waited for Liz to say something and when she didn't I quickly said "Is it time for breakfast?" He laughed and said brunch and we were invited. Looking back I was amazed I took the opportunity to start a conversation with a complete stranger. I think this morning for some reason I thought the light makeup I was wearing matched how my hair looked and my gender dysphoria was not an issue and did not bother me. So I had as much right as Liz did to initiate a conversation.

Amazingly, I felt empowered to do it again when and if the opportunity arises. It felt good to shed my shyness around the public. Maybe if I was more into setting more new resolutions for the year 2023, I could have considered adding speaking up more to my non existent list. As I felt this morning, possibly engaging the public more will help me to continue to build my personality as my authentic feminine self. My excuse is the Covid years of relative isolation hiding behind a mask stunted any personal growth I had with the public. Plus, back in the day when I was first coming out, I enjoyed my time communicating with the public, for the most part. It could have been too I was caught up in the newness of it all. After all, the communication skills women required to survive in their world were so vastly different to me. Even with all the years I spent working with women, I found they shielded me from what they really meant on certain subjects. 

I have considered also that over the years, writing had become my preferred form of communication. To the point of hurting my verbal communication. Since I was afraid of using what I called my feminine voice, I softened my vocal delivery to a point of not being heard by some people. 

Now I hope to try to get out into the public more and practice my vocal skills more in depth. Adding yet another dimension to my overall public presentation. Years ago I did take a few lessons on developing a more feminine voice and think I still have the practice notes and homework I was given. I will have to find the paperwork and try again. Engaging the public was so enjoyable.  

Trans Imposter Syndrome

During the strenuous years of trying to achieve a passable feminine image, I never thought I would ever come close to feeling the  transgender impostor syndrome. In fact, I know for certain for the longest time in my gender transition it wasn't a term at all. Before we go any farther in this post, here is what the imposter syndrome means to me.

Photo from the 
Jessie Hart
Archives

My interpretation is when you have arrived at a certain point of your life which you have worked diligently to achieve,  all of a sudden you feel you don't belong for whatever reason. The closest example I can come up with was when I was promoted to a executive general managers restaurant position I had worked years to secure. Once I did get promoted I always felt I belonged there because of all the work I had put in plus all the success I had achieved. Ironically, I never felt the same when I transitioned to  a full time life as a transgender woman. 

As my life unfolded, I always wondered why I wasn't more satisfied with the results. I mean, hadn't I earned my spot in the feminine world by doing a ton of experimentation which led to learning  what worked and what didn't as continued my often lonely path to gender fulfillment. Even though through much of the journey I had my doubts if I was going to make it at all, still I pushed forward. The one thing I never considered was what would my ultimate gender destination look like. 

I also never considered once I arrived as a full time transgender woman, would I ever feel as if I didn't belong there. Most certainly I have paid my dues over the years learning the feminine life experience. None of the learning came easy but on the other hand it all felt so natural. The first nights I went out to  be a woman, not just look like one was the huge unveiling of what my life could be like if I continued down the difficult path I was headed. Again, after that first successful evening, I knew deep down I could never go back and sooner more than later my life as a male would be over. It was about that time, I began to feel twitches of what I later learned was imposter syndrome. Even though I knew I worked hard at making it to where I was in my gender journey, did I belong there. 

It wasn't until much later in my life when all the new internet/social media driven terminology began to appear did I notice the transgender impostor syndrome. I saw seemingly more successful and attractive trans women and men who had their doubts concerning their journeys also. So I knew it wasn't just my own paranoiac self taking control. In my times of doubt, I was fortunate to have my relatively new feminized body and my wife Liz's reinforcement to get me by. My coping mechanism was I had as much of a right as the next woman to occupy the space I was in.  The world could always use another woman and she was me. I just arrived by a different path.

For the most part, any trans impostor syndrome I suffer from is a figment of my imagination and a part of my past. To be filed and put away with so many other often unexpected circumstances from my long and eventful gender journey.     

The Future Transgender "A" Listers

 Back in the day when I was first exploring my public feminine self, I learned the hard way there were many cliques, even hierarchies in the new transvestite community I was witnessing. First I think I learned that although the group was supposed to be exclusively heterosexual, it clearly wasn't the case. Even though nothing sexual was flaunted in public there was plenty going on behind the hotel's closed doors. particularly among the group I called the "A "Listers.  

Photo from the Jessie Hart
Archives

To me the "A's" were the impossibly feminine attendees. Other groups included the cross dressers who were trying desperately to maintain what was left of their masculinity even though they were trying their best to be feminine too. Then there were the rest of us. While I did my best to look the best I could, I also found myself to be an observer on the highest level. The reason was because I was still so confused on several issues which were dominating my life. At the time, I had no idea if how far I could go as an aspiring transvestite or even if I wanted to go farther at all. Then there was the pesky sexuality question. Little did I know, I would face years of self searching and practical experience before I would come up with any solid answers. 

Even though I didn't fit in with the "A's" appearance or personality wise, I found they could offer me a unique way of seeing the world as a feminine person. One way was even though this was before the transgender term was even invented, the "A's", clearly were a step above most of the other cross dressers who came to the transvestite mixer. However not all of the steps were positive ones. All too often they formed a clique not unlike the prettiest girls in a high school. Regardless, what appealed to me about the clique was they would go out into the world to select gay venues after the mixer was over. I didn't care what they thought of me, I just wanted to get out and explore the world to learn if I could make it as my authentic self. I took advantage to the fullest and even ended up achieving a great result one night after a meeting which included a free makeover to anyone who wanted one. I gathered up all my courage and went for it and was rewarded for an invite to go out with the "A's" to party. 

During our night out, I was further rewarded with a guy coming up to me in a bar we went to who wanted me to sit with him or play pinball. The group was amazed when I was picked up and none of them were. Mainly because I was in a different city than I was used to, I decided not to stay and went back to the hotel with the group. Plus, I didn't know how much the guy who approached me knew of my not so little gender secret. 

In the years following my earliest adventures at the mixers, I actually became a regular acquaintance of a couple of the "A's". One of which I even attended regular parties at her house in Columbus, Ohio. I knew that her as well as the best of group (appearance wise) went on to undergo genital realignment surgeries. Unfortunately, I lost contact with them after that. 

All in all, I learned quite a bit from being an hanger on to the group. I was torn because I badly wanted to look like them but in no way did I want to act like them. In the long run maybe I achieved both.