The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

The longer we live as transgender women and trans men, often we find many aspects which represent a double edged sword. 

One of the edges of the sword has to be the duress we feel when at first we arrive in public for the first time. To make matters worse, we have no peer group to help us out of the mirror to be judged by the harsh eyes of the world. No one to tell us we looked clownish as we tried the makeup arts for the first time. I can't tell you how many times I hurried home in tears following being stared at at the least, or laughed out of a venue at the worst.

From it all, I learned to develop a thick skin and always go back to the drawing board as quickly as I could to help solve any presentation problems I might have had. Even when I was doing it, the cross dresser drawing board was certainly difficult to figure out. What happened was, I used the very brief moments of gender euphoria I earned and moved forward attempting to tightrope my way along the sharp edge of my sword. I was risking ridicule at the least and the loss of family, friends and employment at the worst. Failure as a transgender woman was a very real pressure.

Once I began to learn how to present in public more effectively as a transgender woman, I began to use my sword more effectively.  Then the world became much more comfortable for me in my quest to live my femininized dreams. In addition, my makeup arts became better as well as my use of hair to enhance my appearance. 

It bares mentioning also, going through the overall transgender experience, made me a more resilient person and set up to battle the more challenging times we face. I learned in my research transgender folk have always been around and always will be, no matter who tries to erase us. Battling the sword all these years helped me be more secure in my transgender identity. 

In all fairness to my sword, it started out very dull. I worked long and hard to sharpen it by going out in public which was the best indicator of my progress.  So I took all the good and bad and did the best I could with it. All my interaction with the public included the dark evenings when red-necks repeatedly kept playing "Dude Looks Like a Lady" on the juke box in a venue where I was a regular. Since management at the time would not support me, I left to find another venue and took my money elsewhere. I was rewarded months later when an employee from the venue I was discouraged from coming to, found me in another venue and invited me back. To make matters even better, the manager who would not back me up was fired for drug use. Excluding a stray bigoted woman in the woman's room, I never had any further problems there again.

Once my gender sword swung back into doses of gender euphoria, I began to appreciate all it had done for me. Transgender womanhood was finally mine to enjoy when I learned I was not a quitter and was in my transition for the long haul. 

Trans Girl in the Winter

Image from Freestocks on UnSplash.

I happen to live in Ohio where there is often a weird mixture of the four seasons of weather. For example, when it seemed fall has set in, summer returns and the sweaters and leggings you have pulled out have to temporally go away. Now, around here we have made our way into winter. Which means I have had to dig a little deeper into my collection of leggings to find the lined ones. I love the soft feel of the leggings and how they keep me warm when the temperature dips well below freezing.

For my wife Liz and I's winter time walks, I usually pair my favorite leggings with my furry boots and bulky soft sweater before I have to go outside and brave the elements. These days, I need to force the issue with my walks since Liz and I are going to visit the Florida Keys in January. So I need to do my best to walk as long as I can when we go. Since there is thirty days away, there is plenty of time to write about our winter vacation before it arrives. Such as my first time swimming as a transgender woman.

If I had my choice, I would choose winter over our hot, humid summers any day. I like the fashion and the fact it is easier for me to stay warm in the winter rather than cold in the summer. I know possibly, I may be in the minority of all transgender women who value the look and feel of bare skin in warmer times. While I remember vividly the freedom I felt when I could finally shave my arms and wear short sleeved women's fashions, over the years, the feeling has somehow went away. One way or another, I have traded the feminine feeling of leggings for the sensation of shaved legs in the wind.

Either way, the entire fashion process is one of the reasons I enjoy my transgender womanhood so much. The planning ahead for the seasons means so much and winter is just a portion of the process. Of course we will see if I am just as enthused if we get any sizeable snowfall in December since I have one Christmas lunch coming up with the Cincinnati Alzheimer's diversity council as well as a Yule get together with Liz's circle of friends. During which I will have the opportunity to explain why I turned down an interview with a local television reporter after the election. 

So there is quite a bit coming up in December, including awaiting the arrival of a new laptop I thought I would go ahead and purchase before the proposed tariff's go into effect driving prices upwards. It will be interesting to see how easy or difficult the set up will be. I am not very technologically advanced. The laptop was one of the biggest purchases I have made in a long time. It was an online Cyber Monday purchase so I did not have to put up with any lines or pestering sales people. Patience, along with many other attributes will have to be my main goals following trying out a new laptop in over a decade. 

Overall, the month of December is more enjoyable with the fashion and festive Christmas lights in the neighborhood. I have respect for those who put effort into holiday decorations since all the work I put into my second wife's extensive decorations 

It all makes up for the drab months of January and February. Being a trans girl in the winter is yet another challenge. 

Was there Ever a Plan

Image from the JJ Hart
Archives

Looking back, I needed a very definite plan to follow as I transitioned into transgender womanhood. 

Similar to so many of you, I started by "borrowing" a few of my Mom's clothing when I could still fit into them. I would have added a sister in but I did not have one. When I became old enough to do it, I took on a newspaper delivery route in my neighborhood and combined my new meager funds with the allowance I received at home from my parents and with the money, I was able to buy a few clothes and my own makeup. Since we lived in a rural area outside of town, the plan was to stay a day or two with my Grandma who lived very close to stores *downtown where I could attempt to shop for what I wanted. The problem with the well thought out plan was my Dad worked downtown too and he was the last person I wanted to run into with my new "treasures." 

After I conquered my fear of shopping for cosmetics I did not really need, I was able to buy makeup which did not make me look like a clown. Another problem I had was, the only example I had of applying makeup came when I was able to watch my Mom do it. I wonder if she noticed me watching her. She was probably so entranced in her face, she did not notice I was entranced also. 

The older I became, the more entrenched the plan became. I was able to increase my small "collection" of feminine wardrobe and makeup as I went along and managed to hide it from my brother and the rest of my family. At the same time, I wanted to become better at the makeup arts and finding clothes which fit me. 

At the same time, I became comfortable with how I looked in the mirror and increasingly had thoughts of expanding into the world. I did try to come out fully dressed to one of the very few male friends who lived close by in the neighborhood but was quickly rejected and I scurried back into my dark, lonely gender closet. I stayed in the closet until several Halloween parties began to bring me out. From then on out, my plans really began to change.

During the parties, I learned how much I enjoyed my time out of the closet and I just knew I needed to figure out a way to live as a transgender woman without waiting for a whole year to go by. To do it, I knew I would need to start by telling my spouse what I was up to. So the plan was to find out what wife number one and two thought about me being a cross dresser before we were even married. It turned out wife one did not care and wife two was supportive to an extent which helped me along. 

The main rule I had with wife two was to never leave the house dressed as a woman. I started innocently enough before I veered off course and threatened our marriage of twenty-five years. I began going to women's clothing stores and malls where acceptance was easy to come by. Money was certainly more important than gender. I also would go to bookstores and even antique malls where I could browse with no problems to build my confidence. When my spirits went up, I planned ahead for my next big adventure which usually meant beginning to interact with more of the world as a transgender woman.

To do it, I began to stop and eat at restaurants along the way to make sure I had to communicate one on one with a server or bartender. Since I had an extensive background in the restaurant/bar business, I knew basically what I needed to do to survive. Just be nice, do not cause any trouble and tip well and I could be successful. 

From then on, I endlessly planned on what I was going to to next and how I could challenge myself in the feminine world. Sometimes I was successful, sometimes I was not but I always learned from the experience. In my life as a man, I had never really planned ahead on anything, so this was a big difference. Perhaps it was because I could not wait to try again to live out my dream of transgender womanhood.

*Those were the days of strong vibrant downtowns in many cities, including mine. Before malls took over and they tore the downtowns apart. 

Finding your Happy Place

 

Image from Priscilla du Preeze
on UnSplash

These days you may think finding any sort of happiness as a transgender woman or trans man may be impossible but it is not.

Take this morning for me as an example. As I was getting dressed and viewed my bare thighs before I put on my pants, I had forgotten how nice it is to view their increasingly femininized form thanks to the use of gender affirming hormones. In other words, I have developed my own hips, finally following years of hormonal usage. In many ways I took the slow cautious route when I started down the medical transition path on the advice of my doctor. He advised me to take minimum dosages until we could judge the effects on my body.

At the age of sixty, my body took to the new feminine hormones wonderfully and naturally. Soon I was put on higher doses of HRT and bigger changes began to take place rather quickly. I had set up a semblance of a timetable of when I wanted to shed all my male clothes and live fulltime as a woman but it turned out the timetable was a waste of time. What happened was I became very androgynous looking in a very short period of time. While I was developing an increasingly noticeable set of breasts, my skin began to soften which in turn softened the lines of my face. So much so that anyone who knew me from before would notice the difference.

Even though I was shocked at the rapid exterior transformation of my body, the whole process felt so exciting and natural I could not wait to do more and more as I accessed my new transgender womanhood. It all meant setting up new plans and timetables on who I was going to tell and when. By this time in my life I had outlived most of my family and close friends, so telling many people was not going to become a problem. I had even retired so I did not have to worry about transitioning at a job. All of this left me with two main people to come out to. My only daughter and only slightly younger brother. 

I knew at the time, I had a better chance of succeeding at telling my daughter the truth about me than my brother. My daughter was much more liberal while my brother's in-laws were right wing Baptists and I figured he would sell me out to appease them. It turned out I was right on both accounts. I found my happy place when my daughter totally accepted me and was down when my brother did not. I took my fifty fifty win/loss record and moved on.

To this day my happy place continues with my daughter and her extended family. In fact, my wife Liz and I just accepted an invitation to Thanksgiving dinner at my daughter's Mother-in-Law's house which makes up for the decade long snub from my brother. 

As the holidays approach, I hope all of you can find a happy place to celebrate with family, blood relation or not. In the transgender community, often we find the best family in non traditional situations. It is a wonderful time of the year to discover or re-discover a new happy place for yourself.

Running Against the Tide

Sarah McBride is running for the United States House of Representatives from the state of Delaware. Sarah grew up in Wilmington, and currently represents fifty thousand of her neighbors. Despite her impressive background in community service, one thing sets her off from all others seeking a seat in the House of Representatives, she is transgender.

Even though she is an example of a person going way past being transgender and just being her, she takes it to a whole other height when transgender people are under attack at so many levels by a certain political party I will not mention. At the least, she is an inspiration to the rest of us. 

Just last night I was watching the Texas-Georgia college football game and was unpleasantly surprised when a commercial for Republican Senate candidate Ted Cruz popped up on my television in far away Ohio. As luck would have it, Ohio and Texas have very competitive senatorial campaigns going on. I would estimate over ninety percent of the anti Democratic candidate ads on television involve false transgender claims. Which are brutal and false. Last night I was enjoying a game when the same commercial popped up with only the names had changed. It was a stark reminder that a major player such as an Elon Musk or Peter Theil are aligned against us. I forgot to mention they are both billionaires capable of buying off huge portions of the federal government such as politicians and supreme court justices. 

Enter Sarah McBride, a light in the end of the tunnel which is not the train. Many more pro-LGBTQ political candidates are running in this year's crucial election. As a group we must put our differences behind us and our future in front of us as we must identify and vote for the proper path forward. Sarah McBride is proof it can be done as she is favored to win her race. We need to make sure she is only the beginning.    

 

How Far will You Go?

Image from UnSplash.

I have always viewed my transgender journey as a series of upward steps. A few of the steps were short and easy to take, while others were the opposite. The steps seemed to be impossibly steep and dangerous to proceed. 

Early steps were thrilling and even exciting as I snuck behind my family's back to cross dress in front of the mirror. Even so, the risk of discovery was anything but easy because I was risking so much. In those days, discovery meant a trip to a therapist who knew nothing about gender issues and even worse being treated as if I was mentally ill. 

At that point, looking ahead, I probably knew deep down, things would not get any easier with my gender issues. But, time would tell. As I progressed during my life, it suddenly became obvious  my gender issues were not going to go away. In fact, they were only to become much more serious. Mainly because my male life was becoming so much more serious too. Once I made it through my military service, I settled in to raising my new, small family which I hoped somehow would make me more of a man, while deep down I knew it would never be the case. I wondered how far I would have to go to carve out a good life. 

Fortunately, I was able to even though the trip was difficult, I made it by deciding I would go as far as I needed to go to satisfy living as my feminine authentic self. Initially, I had several major hurdles to conquer. Such as, did I want major surgeries which were much rarer and expensive back in those days as well as how my sexuality would play out as my new self. 

Since I did not have any insurance to cover the surgeries, paying for them was out of the question so I moved on. Next was my sexuality. Since I had absolutely no experience in sexual time with men, I did not know how it would go. It turned out, I did not need to experience much time with me, I never had to move on from my sexuality with women. I was becoming a transgender lesbian. 

Of course, the further I progressed in my new world, the more I had to lose as far as family, friends and employment. I needed to prepare to lose it all if I needed to. I needed to determine if it all would be worth it. In my case, all the years of fear and struggle proved to be worth it. Thanks to my lesbian wife Liz, I was accepted for who I was. 

To arrive here, I did not have to go through extensive operations and change my sexuality. I have always thought gender was between the ears and not the legs so it did not matter to me. I guess it proves how diverse the transgender community is, if we allow it to be. None of the "I'm more trans than you" syndrome which is hurtful to us all. Especially now, in a political environment which is setting out to erase the trans population, we ALL need to be united and not divided behind a bunch of archaic labels, such as cross dresser and transsexual individuals. 

Regardless of the label, we all had to decide how far we want to go to satisfy our gender urges. Or sadly, how many risks did we want to take to change our life forever. It all proves how we never had a choice in who we are as transphobes seem to think we do. How far you go is entirely a personal decision which takes a lot of work and trial and error to accomplish. It' all depends how in depth you want to go. For example, the night I went out to see if I could meet and blend in with other single women on their own turf and survive. I did make it and knew I could never go back to the life I had before in the mirror. I wanted to go more in-depth. 

From then on, I needed the confidence to do it.

Transgender Instincts

Image from Atich Bana 
on Unspalsh. 

 First, I need to apologize for missing a post yesterday. I went to my primary provider at the local Veterans Administration clinic for my semi-annual checkup. While  I was there, I was able to receive my flu and Covid vaccines at the same time I was having my blood labs completed. By the time I had stopped and picked up lunch on the way home, I was pretty much ready for a nap and just laid down. By the time I woke up, I had ran out of time to do a post at all.

The visit itself was very mundane and I did not receive any negative responses at all and was never called "Sir." So I chalked it up to a win. In the past I wasn't so lucky and thought about reporting a couple people there for their transphobic behavior. For whatever reason, things have changed for the better. 

Now, onto instincts we have to develop as transgender women or trans men in order to survive in an often hostile world. Especially true for trans women. It seems we have to be on point at all times with our appearance just to get by and appearance is only the beginning. We need to move smoothly like a woman and learn to communicate one on one with mainly the other women we meet. I know I was petrified when I first was trying out the world as a transgender woman. Then, on a totally heightened level were the aspects of conquering and feeling comfortable in women's only spaces such as rest rooms. Which always is a topic for another blog post. Except when it came to the times when I was stuck in line at a restroom  and needed to make polite conversation with other women. 

These days, having your instincts about you as a woman, trans or not, is more important than ever before.  Depending on where you live, outspoken gender bigots have made our business their business. Plus as we transition into the feminine gender world, we need to be careful when it comes to our personal safety. In particular ignoring dark, deserted places such as sidewalks and parking lots. In particular, all things cis-women learn from a young age. Of course, I needed to find out the hard way about my own safety issues and was lucky I did not find myself in more serious harm than I did.

Sometimes, I feel interacting with the world as a transgender woman has meant developing a sixth sense. For me, my hearing improved as I strained to hear what someone else may be saying about me behind my back. From then on it is my decision on what do next. Recently, I have decided to stare the person down and even challenge them. I have spent too many years living to do anything else. 

Our instincts are powerful basics in our lives and changing genders brings a huge challenge. We have to start all over and learn our lives again. Being transgender women or trans men just brings a bigger challenge. On the other hand, learning to play in the other genders sandbox presents a unique challenge in life which very few humans will ever realize. 

Hopefully, we all can make the best of it and go though a safe and stable gender transition. 

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me. 

It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

Intimidating Women

Library of Congress 
image from 
UnSplash.

During my life, surprisingly so, I have encountered many intimating cis-women. 

Probably the most intimidating of all was my Mom, a dynamo at a mere five foot two inches tall.  From early as I can remember, we clashed on many different issues probably because we were so much alike. On the girl side, I was fascinated from a young age when I watched her skill with makeup and hair. I could only dream of ever duplicating her prowess. Of course I would never get the chance for her to ever see the fashion skills I finally developed as the daughter she thought she never had. 

As I grew up, my intimidation of girls of all kinds increased. I was so jealous of their ability to dress in pretty clothes and wear makeup continued. In addition, I was so shy, I was afraid to communicate with girls at all. So my problems continued to get worse. I never had the chance to circle back to where I began. All the time I was cross dressing in front of the mirror, it was a very solitary, lonely experience as I craved the peer feedback other girls my age had to work with. 

The older I became, the more I admired women who were stronger and spoke their minds. You might say I was intimidated in the most positive ways by strong women. I was even attracted to them to the point I chose one for my second wife who I was married to for twenty five years. Even though she knew I was a cross dresser from the very beginning, somehow I secretly thought she would help me with my on-going quest to be a feminine person. She never really did help me much and very much resisted any ideas I had I was a transgender woman. 

Perhaps I am attracted to strong successful women because I wish I was one. I so admired the women managers I worked with because of all the extra skills they had to use to be successful. Most if not all of them had families to support at the same time they worked a full-time job. I was in the restaurant business and some of my best kitchen managers were women who dealt with macho kitchen crews. 

Being a transgender woman, I think sometimes I intimidate other women. Sometimes they seem to melt with kindness such as the hostess last week when my wife Liz and I went out for my birthday dinner. She was beside herself to make sure we were satisfied with our experience. As I can remember, intimidation on my part of a guy was when I was shopping at a grocery store years ago for the families groceries. In those days, a fashionable woman who had the legs wore an oversize sweater with flats and a mini -skirt, so I did on that day. As I chose our food, I tried to contain my fear in checking out, I found I was wrong.  As it turned out, the store was nearly empty and only had one check-out lane open with a woman cashier and a male bagger. 

It turned out, I really intimidated the bagger, he blushed and stuttered when he asked me if I needed help taking my bags to my car. I looked at the cashier and him when I said I didn't and she gave me a slight knowing smile. I wondered then, if she knew I was transgender at the time or not. Regardless, it was quite the experience. 

It wasn't until I transitioned into a feminine world as a trans woman did I fully understand all the nuances of what it takes to be an intimidating woman. For example, some women use their heels to begin the process. Heels give a shorter woman a height advantage to be able to compete with the men in their world. Plus, these days, more and more young women are becoming educated to give themselves an extra advantage in the world. 

It turns out, in my life, intimidating women are becoming the norm as the future is female. 

 

Becoming Me

Image from the 
JJ Hart
Archives. 

As I bridged the gender gaps in my life to survive, I did what I perceived to be cross dressing as a woman in my family's mirror. 

Slowly I began to learn the makeup and fashion tricks the girls around me used to look their best. At times it seemed I was attempting the impossible as puberty set in and my body began to go through many unwanted male changes. Like it or not, I was stuck with testosterone poisoning and I would somehow have to get use to living with it. I was becoming a me which was very much unwanted. 

As I got by in life, I learned to camouflage my broad shoulders, and torso (among other negatives) and try to emphasize my positives, even if I needed to do it with feminine style padding in all the right areas. Since I was told I had good legs at the Halloween parties I went to, naturally I tried to emphasize my legs when I dressed. 

Sadly it took me many years to learn the truth about myself. Yes, it was true I was a cross dresser but not the way I always thought I was. In no way was I a male cross dressing as a female, all along I was a woman cross dressing as a man. Once I arrived at that point in my life, suddenly everything began to be so much clearer. I just wish I could have come to the realization so much earlier than I did. I always use the excuse to myself the world itself held me back in the pre-internet years before very little was being published or researched about gender issues. In fact, I still remember in my youth the news stories about the police rounding up and arresting men dressed as women. How could that be? 

Still I persisted and remember vividly the night I dressed up in a mini skirt, panty hose, heels wig and makeup and headed to a nearby gay bar when my wife was away. I was so scared and once I got there and was admitted through a locked door, I only had one drink and left before I even relaxed and I never had the opportunity to go back before the owner died and it closed. Even still, my adventure that night helped me to become the transgender person I wanted to be. At that point, the problem still was, I did not totally know who I was, or face up to her yet. But I was diligently working on the problem by researching my feminine life. 

To do the research, I needed to risk everything and leave the safe surroundings of the mirror and enter the world. I started with going to more gay venues and becoming quickly disillusioned when they all thought of me as a drag queen. Lesbian bars were better but I did not find true acceptance until I became brave enough to go to straight places. There I could watch my sports, drink my beer and become accepted as a regular fairly quickly by the staff. I minded my own business, tried to be friendly and tipped well and was in. Even though I knew they knew I was transgender. it did not matter and along the way I think it even helped me. One way or another, I was taking giant steps towards being me and I knew there was no way I could ever go back.

Perhaps the biggest step I ever took on the gender path to being me was when I started on gender affirming hormones. After being approved by a doctor, the changes occurred quickly.. In addition to the external changes such as breasts, hair and skin, I experienced internal changes also. My emotions changed as well as my whole life just softened. The entire time of gender adjustment was one of the most magical times of my life. 

Overall, the discovery of who I really was as a transgender woman was a terrifying yet exciting journey. One I don't regret taking, once I faced up to her, I was so much happier.   

Mental versus Physical

Archive Image
Ohio River in
background.

Is presenting as a woman when you are born male more of a mental or a physical effort?

I think, in my case, I started out with a more physical experience and then moved on to a more mental one. Possibly, it is because it took me so long to grasp the idea I was more of a transgender person in the making and not a cross dresser. I have nothing against cross dressing but it just was not for me. I wanted to go past just looking feminine to being feminine. Sadly, because of the lack of information and other excuses, it took me decades to understand myself. During those times I tried anything I could to resolve my gender pain I was feeling. 

What I did not understand was the amount of pain I was feeling was due to the transition from being a physical appearing woman to a mental operating one. Walking the walk and talking the talk with the public as a novice transgender woman certainly took a toll on me mentally. Finally I was coming closer and closer to solving all the public gender issues I was feeling. Walking and moving as a woman started to feel more natural but communicating with the world as a trans woman was much more problematic. I was very self conscious about the tone of my voice among other things. 

Another concept I did not consider was for the longest time I tried to fool the public into thinking I was a cis-woman. Instead of just resulting to being my natural feminine self. When the public interacted with the real physical person who was me, women in particular were intrigued with me and wanted to know what I was doing in their world. When they learned, I was not up to no good, the response was for  the most part positive. At that point, the mental aspect had to kick in with being transgender. I needed to work on what I was going to do with my old unwanted male self and decide what sort of a life I was going to build for an exciting future.

How I appeared to the world as my physical feminine self was still important and I am not saying it still is not. It just that is much of my appearance became easier to approach because I was all of a sudden I was just dressing to blend in with the rest of the feminine population. An example was this morning when I did not have to put on a fresh face of makeup and a dress to make the short trip to the street curb to pick up the trash cans and bring them back to the house. I could do what the neighbor lady does and just pull her hair back, throw on a pair of jeans and get the cans. This is an extreme example I know but a realistic one when the mental part of being transgender meets the physical part. 

When the two aspects did come together, my life improved dramatically also. There was less stress on my mental health primarily when my feminine inner self took over. It was as if she was saying what took so long. The main reason I took so long to transition was I ran from the gender truth I was feeling for all those years. I should have realized I was born to be a girl/woman long before I did. I did not and paid the price.

I also do not feel good about convincing people like my first two wives to come along through my turmoil. I convinced them I was just a casual cross dresser at the beginning and I was trying not to go further into a transgender world. It was unfair to all of us, Since  I was the driving force in both relationships, it was up to me to do better. Instead, I decided to take the lonely gender path for most of my life. Until I could put the mental and physical aspects of being a transgender woman together and discovered I could settle in and live a good life.      

Legacy?

Messy Office, Messy Mind?

As I see it, leaving a legacy is mostly a male topic.

Little did I know, being a transgender woman was probably the only legacy I could leave with my only child (daughter) and my three grand-kids. As it turned out, I did not have much else to offer. Especially not the usual male attributes such as wealth, possessions etc. A prime example was my Dad who was a self made man. Building his own house and rising to the position of bank president, mainly with just a high school education. 

Along the way, I was surprised to learn one of my grand-kids is transgender, so all of a sudden I became a role model. A role I never thought I would have during all the years of struggle I went through as I transitioned from my old unwanted male life. It turned out in many ways, I proved to my grand-kids anything was possible if they wanted it bad enough. And I was fortunate in that my daughter accepted me the way she did and wanted to share my new self with the kids. So I could not run away and hide. 

I was so successful, I made it to heights I never asked for or ever thought I could achieve. Without a doubt the biggest one when two years ago I received my first Mother's Day card and gift. The card brought me to tears because it was something I never asked for. It meant to me I made it to the pinnacle of my gender transgender transition. 

Adding to my legacy is a year long project my daughter gifted me this Mother's Day from a company who takes questions about me from the family for the duration and then combines them all into a book. When it is completed, I will have had the chance to write about myself and maybe equally as important, is the fact the kids will have the chance to learn about their great grandparents who they did not know anything about. It is important for me to be some sort of a bridge from the "Greatest Generation" my parents were part of to the kids of today. The entire gift is quite the chance to explain my legacy to my daughter and grand-kids. Since I have a degree in history from college, the entire process is important to me.

Legacy was something I had given up on when I left my male life behind. I thought no one would care. When it turned out they did, I was impressed and needed to change my attitude completely. In a way, all of a sudden having family care about my life made me proud of my gender accomplishments.  I indeed would have a legacy as a transgender woman past just someone who changed their name in the family bibles. 

Years ago, a friend of mine did a deep dive family tree research on my families, mother and father and found we had a revolutionary war relative. Perhaps now in the future, after I am gone, some other person with gender issues will read my story and understand they are not the first, not alone and can be successful living the life they want to live. 

  

Ditching Good with Better as a Trans Girl

 

Archive Image
from Witches Ball
Tom on Left.

Ditching good with better has always been a difficult obstacle in my life. 

I always blame my parents for my feelings on doing the best I could on anything I tried. Nothing I did was good enough. If I got B's they should have been A's was a prime example. Even though I was an above average student, I don't remember ever being told I was doing a good job. I think now, their influence carried on with me in every facet of my life, including when I was a novice cross dresser and budding transgender woman. 

It all started with my appearance as a girl. When I was younger and before I went through any testosterone poisoning at puberty, it was much easier to look like a girl. But just looking like a girl was never good enough, I wanted to be a girl and enjoy their life. Or at least as I perceived it to be. I guess my parents attitude was rubbing off on me. At the time, all I could really do to further my looks was to over achieve with my meager allowance and take on a rural newspaper route. Between the two, I could sneak out to the store and buy the occasional wardrobe item or makeup I could experiment with. I was doing my best to ditch my good with better as a trans girl during my early age. If I had given the same effort to everything else I tried during that time, at the least I could have received better grades and my parents would have been pleased. 

On the other hand, my parents in no way would have been pleased if they had known I had issues with my gender. I shudder to think what would have happen to me if they had discovered me dressed in my feminine wardrobe and makeup. At the least, I know I would have been sent to a therapist during a time when even being a cross dresser was considered a mental illness. I never wanted to even consider what the worst could be. Perhaps since we were not particularly religious, Christian conversion therapy would not have been in my future. The only thing I know for sure is, I would not have had any understanding at all. All along I did the best I could and was able to hide my cross dressing with the world. How I don't really know.

The older I became, good certainly did not become enough. A prime example would be the Halloween parties I went to when I was first testing the world  I started with just trying to be a sexy sleaze of a woman thinking I would receive some sort of a validation. Several parties later, I grew more bold and wanted to see if I could be mistaken for a real woman, so I wore my business attire and then waited for reactions. Overall I was received well with strangers who did not know me mistaking me for a woman who did not have a chance to dress up for the party. I was discovering better was always best when it came to how I presented as a transgender woman in the world, under the cover of Halloween or not. 

All of my experiences led me to establishing myself in a new feminine world. I needed to try very hard to do away with all my old values to do it. My whole world became a concentration of new friends and life. In my own way, I needed to be better than the world to succeed in chasing my dream of living full time as a transgender woman. Sure I needed to look the part but suddenly I needed to be the part which meant moving and communicating as a woman. 

Ditching good for better in my transgender world was one of the best moves I ever made. By the time I was medically cleared to begin taking gender affirming hormones or HRT, I was more than ready for the results. Almost instantly I knew I made the right decision.  Since my parents have long since passed away, there is no possible way for me to communicate to them they were right. For all the wrong reasons. Their resistance  to giving me any positive feedback early in life made it easier for me to find my own path in the world as a trans woman. A place where good was never enough for me.  

Much More than a Phase

 

Civil War Cemetery image
from the Jessie Hart Archives. 

When I was first experimenting with wearing woman's clothing, I worked long and hard to hide all my feminine wardrobe and makeup. 

Due to transportation and financial constraints I always had a difficult time adding to my very limited collection. Plus, I always wondered if my Mom ever really discovered her clothes and others I managed to "borrow" for my cross dressing trips to my mirror. If she did, she never confronted me about it. Perhaps she thought it all was a phase and I would grow out of it. Similar to the fallacy, being transgender is ever a choice, I learned my gender issues were much more than a phase.

Very early on, I discovered a lesson I should have relied on but kept on ignoring. The lesson was, I wanted to be a girl, not just look like one. The very beginning of the realization I was transgender as I envied everything girls around me did.  Which went far past their pretty clothes while I was stuck in my drab male clothes. All along I was stuck in a family which valued male superiority and I wanted to rebel but couldn't. I often wonder if I had been born into a more diverse family (if that was possible back in those days) I could have made my feelings known and thrived. Instead, I did the only male thing I knew how to do and internalized all my inner feelings. I even thought, if I ignored my gender issues long enough, they would turn out to be a phase and go away.

Of course my gender dysphoria never did go away and just grew worse as I began to understand the full depth of what I was facing. As I look back, Halloween parties were my first indication I could do more than living a shallow life in front of the mirror as a cross dresser. I learned the hard way, heels weren't so much fun when I first wore them on long walks all the way to how much fun I had experimenting with the clothes and learning from the parties as a whole. Another step towards showing me my phase was not going away, I was just growing into it.

Halloween parties proved to be false feedback in many ways. Most people who saw me were friends who thought Haha I was the clown dressing as a woman for a laugh. Even though I was going as far as shaving my legs. In my mind, my legs alone would do the trick and everyone would know I was much more than a once a year man putting on a dress. At least I wanted it to as I grew confident I could present more and more as a real woman at the party. When I had achieved my goal, I felt I was ready to pursue a future as a successful transgender woman. 

When I did, the work really started. Life was so much more challenging as I left my male phase in my past. I wonder now if my Mom ever thought my simple love of girls clothes was a phase, what would she think now. Outside of the one time I tried to come out to her as a transvestite and she rejected me, we never discussed it again before her death. I can't help but look back and regret how much life I may have lost if she would have ever accepted me. I on the other hand took the high road and honored her by using her first name as my new legal middle name.  

Normally, phases come and go but certainly none of it applies to being a cross dresser or transgender person. Once the public at large learns to accept we are not a phase, trans kids especially could benefit from more understanding when they are young. Parents and siblings could have a more serious outlook of what being trans is all about, helping the whole situation. Or, leave the phase out and help the person. 

The Gender Waltz

Image from Clarisse Meyer
on UnSplash

Since the beginning of time, the two binary genders have done a special dance with each other. 

Being transgender, I have been fortunate to have seen and experienced dancing from both sides of the spectrum. Before I go any farther, I do need to say I am a terrible dancer. In fact, the only time I have tried to dance was when I was so intoxicated I could barely stand up. Sadly, there were recordings made of my dancing struggles.

Certainly, my struggles with dancing were with women . I still tried but since I was so shy, I had very few interactions with girls or women at all. No dancing for me outside of the lessons my Mom made me take. It made it worse as I was at the embarrassing age when many girls were taller than the boys. We learned such trendy dances way back then such as the Cha-Cha as I remember. The grand experiment failed and immediately, I tried to put the entire experience behind me.

Of course gender waltz's go way past just real live dances. Just one of the main ones is inter-gender communication. When the book came out called Men are from Mars, Women are from Venus and appeared on the book stands, I wondered where was I from? It took me years to figure it out. I was from neither. Regardless, it did not take a genius to figure out there are very big differences in the genders other than biological. It is the reason, men and women have such a difficult time understanding each other.

Interestingly, the differences between  the genders extend to what friends we choose. In my case, since I grew up with only other males in my neighborhood, early on all my friends were boys. However, as I grew older, the vast majority of my friends were with women and I had very few close male friends at all. I guess deep down, I was getting ready for my future. 

Recently, I read a post from another transgender woman how she vastly approved having men friends over women. Why? Because she didn't  really like the interaction with other women including the body language on how they crossed their legs  all the way down to how they were sitting. In addition, she didn't enjoy the feminine give and take very much. She much more preferred to talk to men. In my case, I waltzed in the opposite direction. I didn't like the reaction I was receiving from men when I talked to them as a transgender woman. So I resorted back to when I was a guy and was able to communicate the best I could with the women around me. It was all I could do to survive in a new gender world. 

None of my new dance was easy to do. Even though it felt more natural to me. With women, especially, I needed to try to judge what they were really trying to say to me, often in a round about way. Was a compliment really a compliment or merely an opening to try to find out something else about me. I learned the hard way how to dance in a new world not as a cross dresser but as a novice transgender woman. Who knows, maybe other women sensed my innocent approach and it helped me to be accepted. Until the newness of meeting a transgender woman wore off and life resumed. 

Outside of a few exceptions, I rarely had many interactions with men I sought out and was accepted into a world of women. I enjoyed my new dance so much and wanted it to go on forever and so far, without a few exceptions, it has. Maybe I was just trying too hard to dance the wrong way after all. 

  

 

Going Through the Motions

Image from Dibakatur Roy 
on UnSplash.

Looking back at my fifty plus years of life as a cross dresser, I wonder when and how I crossed the gender barrier into being a transgender woman.

Also, how many years did I spend just going through the motion to arrive at my destination. I started with going through what I call now my mirror worship period. During this time, I couldn't wait for any opportunity I had to slip away from my boring, unwanted male life to slip into what feminine fashion and makeup I could find which fit me. Invariably, the mirror would give me positive feedback until I could come back for more. 

I am guessing now but I think approximately twenty years or so went by before I was brave enough to leave the mirror behind and see what if anything the world had to offer a novice cross dresser. On the other hand,  I know it took me longer than the two decades to figure out my truth. I was just going through the motions as a cross dresser and my gender issues ran much more deeper than just wanting to put on a dress and walk in front of the mirror. After years and years of doing the same thing, for some reason something clicked in me which made sense but at the same time was very scary.

It was the time I decided to find out if I could go co-exist with a group of women as a woman in their own territory. Previously, I had scouted out the venue I wanted to go to and when I wanted to try out my idea. It was the "Friday's" I write about often and yes I was petrified for several reasons. What if I did not make it and was ridiculed or maybe worse yet, what if I did and my life would change forever. If I did make it, I knew I could never go back to just going through the motions of being a part-time cross dresser. I was so much more. 

Finally, I got in so deep with me thinking I was transgender I reversed all of my gender thinking. Primarily I wasn't a man cross dressing as a woman at all I was a woman cross dressing as a man. Or, I was just going through the motions of being a male because I was born into it and was just attempting to get by until I could change my life for the better and live as a transgender woman. It represented a seismic change in my thinking on how I was going to live my life. 

By the time I was sixty, I could not take all the self destructive behavior I was experiencing any longer and decided to cross the gender frontier and live as a transgender woman. I embraced all my new gender thinking and set out to discover all I had missed by living my life as a man. Since my inner feminine soul had been observing my life and struggles the whole time, surprises were kept to a minimum. It turned out she was plotting all along how she would live once she got the chance. 

The last major step my male self gave her was going to the doctor and getting approved for gender affirming hormones. HRT just helped to further sync up what I thought I needed to be with what I actually was. Or, I thought I needed any help I could with femininizing my body to help me blend in with the world.

Of course, now I feel as if I was robbed of my life when I was going through the motions of being a man. On the other hand, I made the best of an unfortunate mistake. I gained a daughter, built a solid career and even survived my tour in the Army, so it all could have been so much worse as I battled my own gender dysphoria. It turned out, being transgender just led me into going through more motions than most people.   

A Trans Woman's Intuition

Anniversary Image 
from the Jessie Hart Archives

The world makes a big deal about woman's intuition, as they should 

I feel women as a whole have a deeper understanding of the world than men do. I have always believed women live a more layered life than men which leads to a need for more intuition. Not to mention a less secure life than men when it comes to personal security. Simply put, women have to learn at an early age the problems they could face dealing with toxic males. 

Add to all of that and you can imagine (or have experienced) the problems a transgender woman can face. We have to experience the impact of toxic men and toxic women also.  Lately it seems the anti-transgender societal atmosphere has made it a necessity for trans people to develop their internal intuition more effectively just to survive.

Early on, I was just so starved for male attention, I put myself into dangerous situations. I equated a man's attention into a validation of me as a woman. Fortunately, I was able to live through that portion of my life without any serious harm coming to me. Even though I barely escaped on occasion. I can not claim all of the credit for my escapes as I had other cis-women around me who helped. I can remember one night in particular when a man approached me at the bar in one of the regular venues I was a guest. When the server at the bar saw me and the man approach she did not say anything. Instead she just gave me a look which in no uncertain terms said to be careful. I took her advice, paid my bill and took off before he came back around to me. 

Also, toxic men are attracted to transgender women because they somehow think we are desperate for male attention. Which is the reason so many lonely trans women react to scammers on social media sites. Conservatively, I think I receive two or three scam requests a week from generals and doctors who happen to be widowed. I laugh them off and quickly block them. It never takes much intuition to know where they are coming from.

It is a different story in the real world of course. When women as a whole are warned to be so careful just when they are out to socialize. These days, women have to protect their drinks and make sure they go out with friends. Just another example of how a woman's intuition comes in handy. 

I think when I transitioned into a woman's world, gender affirming hormones aided my progression. In fact, I just answered a question from my transgender grandchild about my favorite smells. During my answer, I made sure I brought up the influence of the femininizing hormones on my sense of smell. One of the first big inner changes I experienced on HRT was the better sense of smell I realized. I am interested to see what reaction (if any) I receive. 

Most certainly I learned a transgender woman's intuition was a priority in order to survive. My inner woman, who waited so long to live her life in the world, knew it also. I learned when she took control how easy it was to let her take the reigns of my life. Early on she proved she knew what to do when she had the chance. I also learned I needed to be better than the average cis-woman. I did not have any of the benefits of growing up as a young girl. Catching up on the fly was often very difficult to do. Little did I know I could benefit from my old male life and use the lessons to help me when I jumped into the girls' sandbox.

Knowing where guys were coming from helped me to get by in the dating world on the very few occasions when I decided to enter it. I found I needed any advantage I could hold to help my gender life along. Including a better knowledge of my transgender intuition. 

 

More LGBTQ Outreach

Image from Brian Wangenheim on UnSplash

Recently I received a call from a therapist at the Dayton, Ohio Veterans Administration hospital. It turns out he is the replacement for my long time therapist who left some time ago. I was fortunate to have had her help for nearly a dozen years.

She was a huge help along the way in me being able to separate my bi-polar issues from my transgender ones. Not to mention all the assistance she provided with the paperwork I needed to change my legal markers from male to female with the government and the VA. Plus she talked me off the ledge more than once when I needed advice pertaining to my transgender lifestyle.

Another one of the legacies my therapist left behind was a series of LGBTQ support groups which invariably leaned towards being transgender dominated. Along the way, over the years, I ran across more than a couple unique transgender personalities.  Some of which I wonder what happened to them and some I didn't. 

It turns out now I may be able to have my chance to see them again in a new LGBTQ support group being put together by a therapist I have never met which will start in August. That means I will now have two outreach groups to participate in per month. The new VA group and the Greater Cincinnati Alzheimer's diversity council. I look forward to spreading the transgender word anyway I can to help anyone I can.

Now, more than ever before, with problem programs looming such as Project 2025, it is time for the trans community to be united before the election. In fact, I had quite the scary discussion with my daughter at last week's birthday party. During the festivities, I learned my transgender grandchild will be leaving The Ohio State University this winter with a degree in nuclear engineering and will be headed to Maine next year for her first job. So any hic-cups with a certain ex-president would not be welcomed. 

In the meantime, I get frustrated when all I can do is reach out to the groups I do and then write about it. Maybe through the other groups, I can finally network out and try to do more.   

Trans Peaks and Valleys

Image from the
Jessie Hart Archives.

Lifetime as a whole presents us with many peaks and valleys to negotiate.

Since I am transgender and always wanted to be a woman, my peaks and valleys often revolved around times when I came out as my authentic self in the world. Very early on, sadly, there were more frequent valleys than peaks as I learned to survive in the public as a novice cross dresser or transgender woman. I vividly remember too many times when I came home sobbing when I was laughed at. I don't remember now how I survived the dark times and continued to move forward. 

As I did move forward, there were other peaks in my life such as when my only child was born. When she arrived, my existence changed forever. Plus, I wondered how having a new person in the world would effect my gender desires. In many ways, I thought it was poetic justice when I had a girl. For some reason, deep down, I thought I could understand a girl better than a boy.  Since my daughter turned out the way she did, maybe I was right.

A big problem I had with my peaks and valleys was staying in one place long enough to actually understand if I was doing anything right. As I constantly changed jobs and moved my small family, I gave my second wife a hard way to go when I tried to chase myself. I am amazed we made it through twenty five years. 

Another problem I had was when I needed to come down off the gender peaks when I encountered them. Gender euphoria was so rare, I wanted to hang on to it as long as I could. When I couldn't I would become frustrated and ultimately mean around my family and co-workers. 

The more I progressed in my gender transition the more extreme the effort to climb out of the valleys became. The major problem was I didn't feel increasingly secure in my old male role and at the same time, I was feeling more and more natural as my femininized self. Which again caused me great frustration when I fell deeper into my valley. At several points I was so deep, I needed therapy to help me restore my mental health. Therapy on occasion did help me climb up to an acceptable level of a peak. When I was smart enough to actually take the therapist's advice. 

It turned out my fear of heights carried over to my transgender issues. The better I became at existing as a woman in public, I was scared. Primarily because for the first time in my life it seemed to be a real possibility I could reach my dream of actually living as a transgender woman. As I looked down on my previous male life, leaving it scared me. What would I do about  losing all of my white male privileges and then having to start all over again. At the time, the only female privilege I could see was a man opening a door for me. Which I later found to be false as there were other feminine benefits I had yet to experience as I climbed my gender peak. 

Finally, at the age of sixty, I could take the pressure of the climb no longer and I decided to stop all aspects of my old male life. I was taking gender affirming hormones to take me to the next step, my mental health was improving and for once I could see my life clearly as a transgender woman. So even though I needed to take a leap of faith off a cliff and transition, I found I had others around me who provided a soft landing. It turned out, I hadn't lost anything at all. 

My up and down life of trying to live as both binary genders was difficult at times to say the least. Near the end I found I made the correct decision on which peak to climb and it was not the male one.