Trans Boomers

 

Without really trying to do so, I believe the blog has settled into having an older clientele, so to speak. Very rarely do I receive a comment from a younger transgender person or even a parent of a trans youth desiring to transition. By far the number of comments I receive come from other trans women of age. Meaning my age. I also have feedback from many other transgender veterans. Where ever the feedback comes from , I completely appreciate it. Here is my latest comment from a reader who prefers to keep her name private:

"When I look back, as I often do these days, I often feel that sense of regret for things done and things left undone. But, then I try to remind myself that my life has been remarkably good in comparison with the billions of sentient apes that have ever lived and is arguably better than most of the billions of humans who presently inhabit this planet. I do wish I had transitioned earlier and more gracefully, but imagine how many never had the chance at all."

Thanks for the comment! I like the parts about your life being arguably better than others who never stepped out of their comfort zone to live their dreams. Plus having the ability to have transitioned earlier with more grace really struck a chord.

I find the main things I have in common with other readers, is what we went through when we started to question our gender to begin with. The main problem we all had was the lack of internet communication with our peers. I remember distinctly the days when I communicated with other transvestites by writing letters, remember those? I believe my first experience with another "friend" on line was on an old "AOL" dial up chat room. All was proceeding past my expectations until my wife caught me one day. Then my brief experiences in chat rooms came to a halt. Until I could find a more secure way to do it.  Those were dark and lonely days in my closet but I was still desperate to get out and sample a more feminine world. 

It wasn't until I discovered Virginia Prince and Transvestia magazine, did I finally have a way to see there were actually others who shared the same desires as me. I was very excited when I learned the "Tri Ess" cross dresser organization  (which was somehow connected with Prince and/or Transvestia had regular meetings in my native Ohio. The first transvestite mixers I ever went to were a three hour drive away in a location up near Cleveland. Even better than that, I learned other organizations were planning get togethers in Columbus, Ohio which was only an hour away. I can't remember for certain now how many of the mixers I needed to attend before I began to feel more comfortable. I mostly was so dazzled to be around other people with similar gender pursuits to mine, I just came to view and judge the proceedings. 

The first thing I discovered was how layered the group really was. It seemed everybody quickly formed their own little cliques. Almost everything on the female stereotypical spectrum it seemed was there. And perhaps most dramatically, the rule that everyone had to be a heterosexual man was quickly thrown out the window. Too many people were disappearing behind closed motel doors to be totally innocent. Then there were the "mean girls" or the attendees who were often impossibly more feminine than the rest of the crowd and knew it.  I so wanted to look as good as them but without the attitude. The best part about knowing the mean girls was being able to go out with them and party after the mixer was supposedly over. That's where the true feminine action took place. Usually, a group went out to a large gay dance venue in downtown Columbus. Just being able to tag along and watch everyone else was my favorite part of the evening. Mainly because I was finally having the chance to live out my dream of living femininely. I felt I could never look as good as the mean girls but I could still enjoy myself.

Today I feel much has changed for the younger transgender population and that is mostly the reason for the "boomer" niche I find the blog to be in. These days (in at least many larger metropolitan areas) there are special LGBTQ organizations to reach out to. I can't imagine though the extra fear and even panic a younger person has these days when they consider coming out as transgender. I guess it proves no one gets a break, young or old, when it comes to being trans. 

I just wish as a trans boomer I could have helped provide a clearer and safer path for the younger generation today.  

Past, Present and Future

From the Jessie Hart Archives
The Ohio State Student Union with 
Brutus Buckeye

I know I write about my past experiences quite a bit but my excuse is I am old and allowed to. If you believe it or not it's my excuse and  I'm sticking to it. One thing I try not to do is dwell too much on the past to the point it effects my present. On the other hand, I find many of my readers who take the time to comment (thank you) share the number of years lived and similar experiences lived  as I have. Even more are very similar. Take the military for example. Since most of us who share the same age will agree, like it or not, the whole experience was a life altering time. Including what we were able to do concerning our gender issues.

In my case, the whole impact of losing three years of my life to serving my country did not impact me as much as what was going to become of my more than serious cross dressing urges. I couldn't imagine my drill sergeants in Army Basic Training would have approved of my favorite mini skirt or heels. On a serious note though, I learned several lessons in life from my gender dysphoria and the military. My biggest lesson learned from both was I could essentially make it through anything if I tried hard enough. In basic, for the first time in my life, I couldn't hide behind my skirts and use the excuse if I only was a girl, life would be better. Which might have been true but the problems would have still been there in a different form. 

The truth was the only unescapable fact that separated my past gender problems was my overwhelming jealousy women could not be drafted into the military and the burden of fighting all the wars and possibly dying fell upon the men. I learned the hard way in basic, to get over my problems and move on. Which was the best possible result which could have happened to me. I think too, my cross dressing-transgender past helped me to get by too. While it was true I couldn't sneak off and practice my feminine craft, I brought the idea with me that someday in the future, I would be free again to be as much of a girl as I wanted. 

Another part of the past which was really important to me was when my daughter was born. Little did I know how much she would force me to begin to settle my life down and be some sort of a father. An art form which I had little past knowledge of because for the most part, my Dad was very unapproachable. Even though my daughter was raised in two separate homes due to her Mother and I divorcing, later in life I found I must have done something right because my daughter grew in to having much of my spirit and also turned out to one of my main supporters during my gender transition. 

The problem is having the opportunity to learn from the past while still attempting to live the present in it's fullest.  Surely there are times I have a tendency to dwell on things I should have done differently in my life. Most certainly the possibility of transitioning earlier was one of them. Even though I know the world was vastly different. As the old saying goes, you can't cry over spilled milk and it quickly becomes useless to worry about the number of bridges you may inadvertently burned. It's a fact a long successful gender transition is better than never taking the chance to do it at all. I wonder how many tombstones in the cemetery would read "I wished I could have lived as my authentic self".  Which leads me to the future. Since I will be seventy four this year, I can see the end of the line and I worry about my health as well as the health of my loved ones. Then, of course what will become of me if I live long enough to find myself in an assisted care facility as a pre opt transgender woman. 

In the meantime, I do my best to honor the past, live in the present and plan for the future the best I can.

Is Seeing Believing?

Image from Unsplash

 Many cross dressers or novice transgender women and trans men spend a majority of their time living in their mirror. Many because they don't feel secure in totally leaving their gender closets and checking out the world. I know I spent years over respecting whatever the mirror was telling me. I would think I looked extremely good, then immediately get laughed at when I gathered the courage to go out the door. I learned the hard way the mirror was lying to me. 

Once I did learn looking good in the mirror wasn't my primary goal, my life changed. Instead of the mirror the public became my focus in judging how successful my feminine presentation was becoming or, how far I still needed to go to be successful in my gender dreams. Once I started to begin to communicate one on one with other women, I began to see in their eyes and actions how I was doing. The whole experience of stepping out of the mirror and into the world was at once exciting and terrifying. But everytime I felt as if I failed, I picked myself back up and decided to try, try again. 

Along the journey also, I learned there were so many different kinds of women. Some were attractive and had their own sort of extra special passing privilege and others needed to work harder on their hidden strengths to get by. I finally concluded being the most attractive woman in the room was not a reachable goal for me but perhaps being the most authentic one could be. By setting a more realistic idea of how I was presenting helped me to survive in the world.

I wonder now with all the anti-transgender feedback going on in the country, how it will effect the segment of cis-women who do not possess passing privilege. What  will happen when other people begin to question their restroom usage?   Will the transgender community gain more allies by default? It will be interesting to see what a cis-woman thinks when she is faced with the same discrimination trans girls grew up with. 

If by chance you were a "natural" and your feminine transition was relatively easy, perhaps your life in the mirror was too. For the rest of us the learning curve was so steep, hanging on was often the main problem. The mirror was all we had to get by since we didn't have a real peer group to rely on. I have included the infamous "faux" teenaged dressing years in this thought. Sadly, most of us were far beyond our younger years when we first escaped the closet and tried out a new world.  

Seeing is believing for me came when I became confident I could negotiate the world as my authentic feminine soul had wanted to do for so many years. Mostly pursuing my goals as a very serious cross dresser. It took me many years to realize the truth I wasn't cross dressing as a woman at all. In reality, I was cross dressing as a man and the mirror never told me.

Impostor Syndrome Revisited

 

Pride Ohio River Photo
from the Jessie Hart Archives

For many years as I started my transition from male to female, I felt as if I was an actress just trying to fit in with the world. In many ventures into the public eye I felt I needed to concentrate on having a feminine walk, among other important things. In many ways I was creating my own problems as I began to settle into a public presentation which fit in with other women. As I was having fun exploring all the new aspects a woman takes for granted, I was feeling guilty about my progress.

All along I wondered why. After all I was beginning to live a life I  previously could only dream of doing. Perhaps it was because I was still experiencing my age old guilt I suffered in my lonely, dark gender closet as I was growing up. In other words I was experiencing the same old problem expressing my true authentic self. At times the struggle seemed to be to much to bear. As the saying goes, what doesn't kill you, just makes you stronger, did make me stronger in many ways and hurt me in others. I overcame by trying my best to explore ways to power through my gender issues. 

By powering through, I attempted many less than successful opportunities to express my new self. I ran the gamut of reducing a young grocery bagger to a stutter all the way to be snickered at and or stared at in public when I tried too hard to be sexy. I  found when I did that, I never had the chance to experience impostor syndrome because I was attracting the attention for all the wrong reasons. For awhile, one of my favorite activities was making sure my short skirt was even shorter when I slowly passed a semi truck on the highway. When the driver responded with a horn blast or the flashing of the lights, it validated my femininity. Which I discovered was all wrong.

My impostor syndrome really began to kick in when I found myself in situations when I needed to communicate one on one with other women. All of a sudden I needed to evaluate what I should talk about and how I was able to voice it. Often I would be talking with another woman feeling great then the doubts would set in and I needed to try to encourage myself to keep going. If you are familiar with bowling at all, it is similar to bowling three strikes in a row then overthinking the next attempt and totally messing it up. 

It took me many years to overcome my impostor syndrome by primarily realizing I had as much of a right to be a woman as the next person. As with every other female I had earned my socialization rights. I can't stress enough how difficult the process was for me. My deep seated paranoia (from childhood) that somehow living as my chosen gender was wrong took almost as long for me to completely overcome it.  But I did and these days my primary response to impostor syndrome is to get over it. Especially if I encounter any out spoken gender bigots.

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.

Transgender Misconceptions

Image from Markus Spiske
on UnSplash

Since I had worked in the restaurant business for nearly thirty five years before I retired, I had a fairly good idea of how cis-women could trash a bathroom. So I often read with humor when I saw a novice trans woman and/or cross dresser singing the praises of how pristine women's restrooms tended to be.  Over the years, even before I began to use women's rooms exclusively, I began to develop a complete problem over how women discarded feminine hygiene products.  One restaurant in particular seemed to be more vulnerable than others I managed and I had to call the plumber approximately every two weeks for a stopped up toilet. In one restaurant I even put up signs asking women to please use the proper waste receptacles provided. All to no avail. Plumbers remained on my speed dial.

Little did I know, all of this would be just the beginning of the realization that women really weren't that much more tidy than men in the rest room world.  My first example comes with a warning to always look before you sit to pee. Sadly, it doesn't take very many wet butts for the point to get across that the last woman or two didn't bother to clean up after themselves. Plus, as the years flew by, I saw women using the rods holding the stalls up as acrobatic holders for their tricks. Wearing skirts or not.

Perhaps the ugliest women's room (if you really wanted to call it that) was at a venue in New Orleans during Mardi Gras. As I remember, the room had just enough space for a toilet and a sink. But the worst part about it was the smell. The place reeked of sewer gas so I hurried up and finished my business. It was so bad the tank lid on the toilet was just a piece of wood. As I said, I didn't waste anytime getting out of there and I was sure I had spent more pleasurable restroom experiences in "Porta Potties" or the green heavy plastic toilets you see at many construction sites. Even still, unbeknownst to me, a line of women had formed at the door waiting for me to finish. The first woman in line flashed me a disgusted look, probably thinking I was  responsible for all that smell. I didn't stop to return the favor  and headed back to our table while warning my then date Liz of the nasty potential which awaited her in the woman's room. 

By now you are probably thinking of all the gross men's rooms you have been to and most certainly that is true. Nature is an equal opportunity provider when it comes to rest room slobs. It's too bad when part of your job is having to clean up after a person or persons who don't care how they act. I can't begin to tell you all of the toilet stalls I have been into where the door latches and even the purse hooks have been broken. Even in newer venues. And, there is more.

The worst acting person outside of a restroom comes from a transgender woman She was in a group I was with viewing  an Any Warhol museum exhibit. She was coming down an escalator in front of me when all of the sudden she held on to both sides of the escalator and spread eagled flashed whoever happened to be watching below. She had a lot of class. It happened to be all low. Proving once again it doesn't matter if you are dealing with cis people, male or female and/or transgender people, it takes all kinds to screw up a world.

Plus, it doesn't just have to be in a rest room, where on a couple of occasions I had to nearly push my way through a group of gossiping women just to get to an hand dryer after I washed my hands. In fact I ended up giving one nasty cis woman a hair dryer experience when she wouldn't move and got too close. It was good for me.

If you are new to the restroom world expect the best but don't be surprised by the worst.

Fake it Till you Make It

 

photo courtesy Jazmin Guaynor
on UuSplash

I heard this comment from an unknown cis woman on a television show I was watching last night and it brought back so many memories. Some were pleasant, some not so pleasant. Similar to so many of you, I share many days and even years of living in the mirror as a young cross dressing girl. During these formative gender years I worked diligently on my makeup. While my other male friends became proficient at painting model cars, I increasingly became better at applying my own makeup. Even to the point of being able to buy my own makeup supplies with my meager allowance and earnings from delivering newspapers. Even though I did become fairly good at applying my own makeup, I still thought I was a pretender until my second wife began to ask me for help with her own cosmetic usage. 

The problem I had was, or one of many, I still didn't realize I had the entire gender situation backwards. All along I thought I was a cross dressing male but in reality I was a girl cross dressing as a guy. Not realizing this basic fact cost me decades of torment as I struggled to find my way out of a very dark and lonely gender closet. The only good which was coming out of the entire process was, the better and more I faked it, the more I slowly began to make it. 

The making it came in stages. I needed to grow out of my girlish adolescence and be able to dress my male body the best I could so I could make it better in the public's eye. Once I was able to accomplish this difficult task with little or no feedback, I was able to begin to sync up my overall feminine appearance and be successful. Or so I thought. I thought if I applied the lessons I learned the hard way in the public's eye and didn't get too outlandish, I could present fairly well as a woman. I did so well on a couple of occasions in New York when I was mistaken for a cis-woman at transvestite mixers, I went on a giant gender ego trip. I was so excited with my results making it a woman, I couldn't wait to do it again and again. It was all good until my wife stepped in and interrupted my ideas of further expanding my feminine pursuits and we began to have massive fights. One in particular which I have mentioned in my previous writings was when she told me I made a terrible woman. 

Of course I finally told her I wasn't trying to make anything but I still didn't have the courage to tell her what I really thought. I loved it when I could try new things as a woman. As it turned out, after she calmed down, she told me her comment didn't have a thing to do with how I looked. It was how I acted and the comment changed the trajectory of my life forever. What could I ever do to understand exactly what she was telling me. I was finally making it on appearance but still faking it as far as feeling good as a woman. It didn't come over night but after many years of trying I finally came to understand what she was talking about. In fact it took the presence of estrogen in my hormone replacement therapy for me to learn the effects of both male and female hormones. Sadly my wife passed away before she ever had the chance to see the complete transgender woman I had become. I don't labor under any ideas we could have stayed together but maybe we could have remained friends.

Age played a role in me being able to fake it until I made it as a transgender woman. I had enough time to make all the gender mistakes I made and still learn and survive. I most certainly faked my gender as a guy until I made it as a woman.