I'm Back...Mostly

 

Well, my wife Liz and I's vacation to the Florida Keys was eventful, with many unexpected turns.

Since I have quite a bit to write about, I will start at the beginning of our bus trip. As we boarded a nearly empty bus way before dawn in suburban Cincinnati the morning was very cold and clear. From our boarding point, we needed to make two other stops to pick up other passengers for the trip in nearby Northern Kentucky.  Since we were nearly the first on the bus, my paranoia about being the only transgender passenger was calmed, especially since I was under the cover of darkness. 

As daylight came around and the bus filled up, the pressure for me to make a good first impression came with it. I managed to cope with a small mirror I put away into my purse, along with my foundation powder and lipstick. So instant touch ups were within my reach.

Of course, all too soon came the all-important first rest room stop. I stayed very close to Liz as we went in and there were no problems with anyone on the bus, or other strangers who were already coming or going in the women's room. I did my business, washed up and left with no interference which made me feel relieved after all the months of worry I put into thinking of what could happen. 

At this point, our bus driver deserves a strong recommendation for his work in getting us safely through very snowy and icy road conditions we encountered as we made our way south from Ohio. He also was available to help me on and off the bus when needed. 

Long story short, we made it to Georgia and spent the night in Macon. Then off to Orlando for our next stop.  By this time, I could not wait to make it to our staging destination of Key Largo. Then Liz and I began to notice how many people on the bus had bad coughs. Which is a spoiler alert for what happened to me later in the trip and would involve a trip to a hospital in Georgia. 

More on it, plus a very pleasant trip to Key West coming up when I finally begin to feel better, because I caught Covid on the bus. Even though I had been given the booster three months ago. Make of that what you will.

 

 

A Genderless Journey

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Jessie Hart
Archives

Recently I needed to take our car to the oil change place to get the transmission fluid replaced. 

In the past I have written concerning my paranoia of going to male dominated places. Since normally I am the only feminine person at the oil change place, the usual paranoia set in. The last time I was there, I was called "Ma'am" several times and had no gender problems so I did not really expect anything else this time. 

To prepare, I shaved closely, put on my foundation and contour blush with lipstick and was ready to go after tying my long hair back. Off I went to get the car serviced hoping I would not be mis-gendered. 

It turned out all my paranoia was baseless. I was treated with respect and not referred to as sir. Plus it turned out the whole process needed much more work than a simple oil change. So the manager was very much involved in the process. At times, he was so involved I wondered if he was trying to impress me. He even went as far as helping me turn off the "perform maintenance soon warning" off. Maybe I was the recipient of female privilege. Or, I needed help and he volunteered. 

Very soon the process was over and I was free to go (after I paid) and it was time to go through the drive thru of our favorite coffee place for a treat. The pressure was off and once again I wondered why I got so worried about going at all. Looking back, I have never experienced any negative feedback when I have gone to male dominated spaces. I guess I am afraid of being taken advantage of. When most of the time the opposite has happened. For the most part, men have bent over backwards to help me.

Maybe I will never change but I doubt it because the transition scars  run too deep. My gender dysphoria ran too deep as a transgender woman. It could be time to change my own oil.   

Just Weary

 

Image from Harry Quan
on UnSplash

Following a lifetime of doing my best to maintain a male lifestyle, I grew weary of living a lie.

Similar to many transgender folks and/or cross dressers I grew impatient with the progress I was making with my gender transition. I had two main problems, the first of which I did not know where I was going and the second was I had no basic idea if I was ever going to learn the basics of what I was doing. Very quickly, I tired of just looking at myself in the mirror and wanted more. I wish now I would have seen my feelings as being transgender but all of this occurred well before the term transgender was invented and became popular.

At the time, my frustration level was rising to an all time high. I was doing my best to learn the basics of feminine presentation but rarely had the chance to try my efforts in a public setting. Those occasions just happened to be Halloween parties which I learned many new basics from. Such as what happened when I dressed slutty compared to when I dressed in feminine professional attire. As Halloween rapidly approaches, I will try to be more in-depth on what I learned which helped me along on my journey to be a transgender woman.

As I went along, my femininization lessons just increased my weariness of being male. I grew extra tired of all the games guys play when they size each other up in the world and I wanted out. I could not wait until I could head home and escape into the safety of my woman's world, The whole problem was, my world was still so isolated and I needed to get out. To enter the world, I dreamed up ways to do it and began by going shopping where clerks had to accept me for my money, not my gender. I also started out by going to gay bars thinking I was safe there. In the long run, I discovered neither did me much good as I was not challenged to build a better feminine self. As I said, acceptance was a given in the clothing stores I went to and not a given in the gay or lesbian venues I went to. Through it all, with the ups and the downs, I learned I was on the right track to my gender discovery. Even though I needed to make sure the light up ahead was not another on-coming train.

My salvation turned out to be being myself, as I ended up going full circle and enjoying the sports venues I enjoyed going to as a guy. Sure I was scared at first, but I followed my instincts of being friendly to the staff, dressing to blend in with the other women and tipping well. Before I knew it, I became a regular at several venues as I enjoyed myself. During this point of my life, even though I was still intensely lonely, I still was increasingly weary of any idea I was still a man. 

To do away with any of my masculine traits became a primary goal of mine. I worked hard to lose weight and take care of my skin to do my best to improve my femininized appearance Plus the addition of the gender affirming hormones I began very much improved my confidence and outlook on life, I finally had arrived at my gender tipping point when all the male clothes had to go and it was time to consider coming out to the closest friends and family I had left. 

It was time to leave my weary life behind and open the doors to an exciting new life as a full-time transgender woman.  .  

Gender Prison

Image from Denis Oliveria
om UbSplsh

Many transgender women and trans men have spent numerous years in their own gender prisons. Sometimes referred to as closets. 

Unless you have had to spend time in your own prison with the walls closing in all the time, you have no idea of how bad it is. Just another proof being transgender is some sort if a choice. Why would we ever choose to possibly destroy ourselves with our gender issues. It all got to the point with me, I was doing all I could to manifest myself being as feminine as I could. When all along my male self was telling me I couldn't. 

I finally arrived at the point where I was given free time from my gender prison to explore the world as my new self. When I did, most certainly I discovered I wanted more and more free time. I discovered also, I needed a ton of work to prepare myself for freedom. I was not prepared for all the challenges I would have to face as a novice transgender woman. Since I had spent so much time cross dressing in my life, I thought how much harder could it be. I never factored in what my second wife was always trying to tell me, I did not really know much about being a woman and she was not going to do much to help me out of my gender prison. 

When she told me that, I reverted back to working ever harder to understand what she meant. Since I had studied women closely my entire life, I resolved myself to trying to get behind the feminine curtain to learn more. It would take me years to get there since it seemed I was living a life time sentence in my gender prison. Outside of a few varied chances to thrive, my prison seemed to be escape proof. How was I ever able to leave my prison without jeopardizing all the white male privileges I had worked so hard for such as family, friends and employment. It seemed the more I tried to escape, the more the walls closed in on me.

Once I staged my big gender prison break, there was no turning back. I discovered that even though my wife would not help me pull back the feminine gender curtain, other women would and I took advantage of their kindness. Even when I was able to, I found I was still looking over my shoulder for any male prison guards who were chasing me. It turned out, even in heels, I was faster than they were and I managed to outrun my naysayers which mainly was myself. 

With practice in the world, I finally put my prison time behind me and I set out to live my dream life as a fulltime transgender woman. One way or another, I had paid my gender dues for nearly half a century before I had the courage to fully transition. It felt so good to be let out of my gender prison and not have to go back. 

My parole officers turned out to be the women friends I found and cherished as I learned so much from them about living in a feminine world. When I used their input and included it with what my own inner woman was telling me, I was able to make a smooth transition even smoother. Plus, I was able to use my prison time as a powerful motivator of what not to do in the world. Even as a man, I tried to treat women differently than the other men around me. Mainly because I wanted so badly to be one of them. 

In the end, spending all the time in my gender prison did not do much for my life. I spent so much mental energy rebelling against my male world, I often wonder how much farther I could have gone if I had used all my resources. It wasn't to be because I was in my own gender prison and could not find the key.

Bridging the Gender Gap

 

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on UnSplash

It is a dirty job but someone has to do it, right? We transgender women and trans men are in a unique position to be the only go between both of the primary genders and make a difference. If society and politicians let us.

I did not set out to write another post criticizing a certain political party in my state of Ohio  which is trying to do away with all transgender rights. You all know where I stand. Instead what I am writing about is singing the praises of acquiring deeper gender knowledge. Very few humans ever get the chance to journey across the gender border and see how the other half lives. 

Interestingly, there were times I was asked for my feelings about how another woman's spouse or boyfriend was feeling towards her. Women are more intuitive than men and were seeking out my ideas because they knew I at one time, had occupied the male world. I was filling a void they could not find anywhere else. 

Even still, bridging the gender gap was exceedingly difficult. There were so many things to learn about how the genders interacted with each other to survive in the world. In addition, I needed to adjust to being the pursued gender rather than the pursuer was all I thought it would be. I grew up with the idea girls or women had it easier because they did not have to go through the torment of finding dates, right into deciding what was the right date for me. That is if I was ever asked. Which was not often since I was mostly rejected by men. The feeling was mutual because I did not feel any particular attraction to them anyhow. Especially so when I was accepted into a group of lesbians who showed me my validation in the world did not involve men anyhow. 

My new friends taught me how to bridge the gap and learned so much from them while I did it. I was raising the bar in my life without, for the most part, realizing I was doing it. It was difficult learning to walk the walk and talk the talk as a transgender woman but slowly I managed to do it. I think now my major success came from the point I was finally putting my gender picture together. I was no longer a one man show, I was a one woman show. I could see my gender dream was possible following years of denial and struggle. 

Looking off the gender bridge proved not to be so intimidating any more. Even though I was still afraid of heights, I learned my gender issues did not involve heights at all. It was more a matter of me keeping my feet on the ground. 

Once I did, being able to help anyone else with understanding gender issues was a huge plus. Paying life forward for me has always been a powerful motivator. Plus, being able to shine a light on the gender differences between genders is not something to be feared. The differences should be embraced and celebrated. Including those of us who have been fortunate enough to have the chance to experience both sides of the binary genders. Even though, for me at least, all the down times and bumps in the road I experienced did not feel so good at the time. 

If I could tell my young self one important fact, it would be to relax, learn as much as I can and know I would be successful in the end and bridge the gender gap. Plus, if I stopped building unneeded bridges to climb and jump off of, I would be so much better off.

A Trangender Happy Place?

 

Picnic Image from the Archives. 
Liz on right. 

Is there really ever a "happy place" to be considered if you are a transgender woman or a transgender man.

During our lives, we go through so much turmoil and change, we have very little chance to be happy with our choices. Primarily because we enter our interactions with others in a dramatic way. A prime example is the swapping of gender privileges. I remember vividly the night I lost a portion of my intelligence when I attempted to talk about a topic I knew quite a bit about with a man, It was the opposite of the intimidation a trans man friend I know told me about his new communication skills with other men, including rest room visits. Up to the point of me thinking initially the only privilege I was gaining was having men open the door for me. Later I learned I was wrong, there were other more substantial privileges to be gained by joining the world of women. They were just hidden from me and I needed to earn it. 

All the gender privileges in the world I found could not make me happy. Of course I could trace my search of the illusive happiness back to my up bringing. Being happy was not a priority in our family and I did not know how to be happy. So it took me years to at the least be satisfied with my gender transition process but not happy. I just had to be willing to take the walk. Since the walk included many ups and downs, my happy place still was difficult to find. Also, per norm, I was doing my transition different than many others. 

Examples are how I found other women who accepted me for who I was. I did it by going out repeatedly as a single transgender woman and risking the inherent danger in doing so. I was lucky and escaped several potential risks to my personal safety when I did it. The small circle of friends I found and I consumed way too much alcohol and drove all too frequently. Something I do not recommend to anyone. Another chance I took was going on line dating sites to try to find a partner since I was so lonely. Predictably, I was hammered by trash and less than stable responses. Plus, when I refused to meet up with the occasional local person who responded to me, unless we met first in a public spot, I was met with no shows or some squirrely guy who wanted to wear my panties. Not to mention the guys who were married. One of which I had a fabulous date night with but I knew there was no future. 

Through it all, I was still thinking I could find happiness. Somehow, I knew happiness could be around the next corner of the path I was on and was I blaming I could not be happy because I was transgender. Quoting "Jelly Roll" there was a very dark hallway between my ears. I needed to give up any ideas of impostor syndrome when I was successful in the world of women. I could not be happy until I gave up all of the guilt. After all, I was not doing anything wrong when I just was attempting to leave my old male self behind and live as my authentic self. 

All of this leads me to the question, am I happy now and does a transgender happy place really exist. While I am satisfied with my life as it exists now, I still work at being happy. For me happiness will be a learned response I can blame my parents for and not a result of being transgender. In fact, more than a few of the moments I call gender euphoria (or happiness) came because of my gender journey. 

The problem with envisioning a life of not having gender issues is impossible for me because I have always lived with it and it was never a choice. So I am biased that a happy transgender place has been very difficult for me, I have partially lit the dark place between my ears and am constantly searching for more. 

Life in Her World

Image from the Jessie Hart
Archives

Once I was preparing to live as a transgender woman, I needed to figure out what to do with my new life. . 

As it turned out, even though I had worked for years to figure out my ultimate gender puzzle, I found I still had a long way to go. When everything ceased to be in my mind and into the world, I faced the formidable task of rebuilding my life as a trans woman and leaving my male past behind. The first major problem came from my old male self accepting any of the idea at all. He kept reminding me of all the risks I would be taking if I transitioned. What would happen to my family, friends and employment if I entered my new exciting world. What I did for the longest time was attempt to live with one foot in one gender and one foot in another. Of course, my less than wonderful idea did not work and the pressure to move into her world fulltime became unbearable. I finally realized I did not have a choice and  I just had to complete my transition. I emphasize I had no choice because some transphobic individuals think I did. I would like them to live just a small time in a transgender life to permanently change their minds.

Another problem I had was the longer I lived in my new trans life, the more routine it became.  I found myself slipping back into my old male bad habits which were long gone. When my white, male privileges disappeared, I had no where to turn when life turned the tables on me. A primary example came on the occasions when my personal security was threatened as a novice transgender woman just learning the world. I discovered I could not just bluster or bluff away problematic situations which arose in the world. In many situations, like every other woman,  I needed to work hard to distance myself from the problem and try to learn from it.  Every time I slipped back into male mode, I was rudely reminded of what I did and quickly adjusted.  

Just moving around became a priority for me. I needed to unlearn the male walk and talk and learn to try to flow like a woman. I practiced everytime I could until I thought I had achieved a basic successful walk so I would  not look like a line backer in a dress. The whole process became easier when I finally realized I needed to put my male self away and adopt the feminine one forever. Without totally knowing it, I had moved away from my cross dressing days into a life in her world as a transgender woman. As far as talking was involved in the process, I write about the feminine art of communication often. As a male my habit of frontal aggression needed to go away as I found myself in a world dominated by passive aggression. All too often, I suffered the pain of claw marks on my back when I thought I knew what another woman was thinking or doing. Instead of making the first move in situations, I learned to lay back and let the other woman make the first move and then go from there.

Life in her world then became a question of how confident I had become. I came to realize even though another woman realized my path was different than hers, I still could be accepted as an equal. When I reached this moment of confidence, my life changed forever and I knew I could live the life I always dreamed of. In her world where I always belonged. 

In order to do so, I needed to finally trust my inner feminine soul to take over and run my life. She did a wonderful job since she had waited so long to do it. I was able to become a well rounded person in her world.

Is it Sustainable?

 

Image from the Jessie Hart
Archives

When I was cross dressing for myself in the mirror, it was easy to imagine me sustaining how I felt when I put on my small stash of feminine clothes. It seemed as if the feelings could go on forever. Then all too quickly I found I couldn't sustain my feelings of gender euphoria any more than a couple of days at the most.

At that point, I began to wonder about the feelings the clothes brought on to start with. I recognized at a very early age more was going on than just appearing pretty to myself in the mirror. I wanted to be the girl I had become, rather than just look like her. If I knew then what I know now, I would know my feelings would later lead me to discovering a transgender life. Perhaps if I thought it would be sustainable, I may have transitioned earlier.

One of the main problems with sustaining myself as a trans woman was maintaining a presentable feminine appearance. I worked hard to do it and when the mirror in the women's restroom I went to one night in a gay venue where I was meeting two lesbian friends told me I looked good, my confidence soared. It was summer and I was dressed all in black that night with  a sleeveless silky top with black flowing pants. I finished the outfit off with my favorite black sparkly sandals and long straight black wig. Fortunately by this time in my life, I learned the hard way my male privilege of personal security was gone so when I left, I asked my friends to walk me to my car which was parked in a dark urban parking lot. I had been there before and had been stopped by two men seeking money. Luckily a mere five dollars got me out of the bind I was in.

Keeping the appearance issue in mind, my biggest sustainability issue came from worrying how I would support myself if I transitioned. The industry I worked in, I knew would be very difficult  to succeed in if I suddenly changed my gender from male to female. So I knew I would have to find another way of financial support. What I came up with was getting old and just taking the early retirement option of Social Security. It wasn't a lot of money but it was enough to get me by and save me the extreme potential problems of trying to come out at a new job. 

So with all the help I discovered from my Veterans Administration health, doors opened for me which I never thought possible. The prime one was all the help I received when I finally decided to begin gender affirming hormones or HRT. A therapist was provided as well as my medication co-pay for all the meds I needed to really change my life. With those meds, at a price I could afford, my long term sustainability was secure. 

Perhaps the tragic aspect of all of this is almost all of my friends and close family had passed on. Leaving me with fewer and fewer people to come out to. However, times of potential gender trauma were greatly reduced and new doors were opened to me I never dreamed of as a transgender woman. The sustainability was there and so was I.  

An Opportunity or Challenge

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on UnSplash

If you are similar to me and if you had a quarter for every time you heard a so called problem was no more than an opportunity to improve, you would be wealthy.

As I moved forward down my gender path, I found an increasing number of opportunities. As I mention often (or all the time), I had a difficult time adjusting to how I should try to present myself as a novice cross dresser. All outfits which included too short mini skirts or shorts were out. In place came a more conservative wardrobe which I found I could blend in with the other women I encountered. The challenge or opportunities I encountered were exciting yet terrifying. 

I had many firsts to deal with in my wide wonderful new feminine world. Many of the firsts I encountered, did not go smoothly and I went home sobbing. When I did, in the safety of my own home, I took ownership of the damages and attempted to build a plan to do better in the future. I went through every opportunity to improve such as better makeup, wigs and wardrobe as examples. I was very focused on the entire process. To the point, I had a difficult time when I still had to function as my old male self. I experienced a new challenge to stay in cross dressed mode when I flipped my gender script. Slowly but surely I was spending more physical time as my feminine self. It took me years to realize I was a woman cross dressing as a man. Not the opposite. 

Then, when I really started to seriously cross the gender frontier and deal one on one with the public, other opportunities or challenges became important. By this time, I was becoming very courageous in how I lived my life. I sought new venues to see if I would be challenged as a transgender woman. Some worked out and some didn't, so I crossed many off of the list. Many of the opportunities became challenges back in those days when I first began to seek access to women's restrooms. The whole process was an overall success with some notable failures when I had the police called on me. Still I persisted and earned my rest room privileges the hard way by learning the etiquette involved with using the women's room. Such as always looking other women in the eye, not putting my purse on the floor and pausing to wash my hands (no matter how much attention I was creating) among so many other nuances I was learning. To go into it all would entail a whole different blog post.

Another huge challenge or opportunity I faced was when I decided to begin gender affirming hormones, formerly HRT. There was no way I could anticipate the changes by body would go through. Both externally and internally as I was suddenly seeing the world in a softer version of it's former self. My sense of smell heightened and my thermostat changed as I became colder easier are just two examples. All in all, my body took to the changes easily and I felt as if I should made the change years before I did.

If I had utilized all the time and energy I needed to overcome the challenges of changing my gender and put the energy into my male self, how much farther could he have gone. The end result was so powerful, there was no way I could ever look back and change my reaction to anything.  

You Don't Know

 

Image from Noah Grossenbacher
on UnSplash

You don't know what you don't know is so appropriate when it comes to describing a lengthy transgender transition. 

Similar to anybody else, I had my predetermined ideas of the steps I would need to go through.  Very early on, I was so involved in looking the part I failed to realize all the other intangibles I would face along the way.  My all encompassing desire to be an attractive woman many times would lead to huge fights with my second wife. She was a very strong, down to earth woman who accepted my cross dressing desires but drew the line at any idea I was transgender. Since she didn't wear much makeup at all, she was fond of calling me the "Pretty, Pretty Princess"  when I put the time and effort into being the most attractive woman  I could be. I got my revenge when we were going to an event where she needed to wear makeup and she was forced to turn to me for guidance. 

What I didn't realize how much my old male ego entered in when I was fortunate enough to be mistaken for a woman in the rare times I was out in the public's eye. Mostly without my wife. What happened was my gender euphoria was at an all time high, for a small amount of time. All too soon the euphoria would wear off and I was stuck with the same old feeling of living a male life I didn't want to. I wanted to explore the world more and more as a woman and the person holding me back was my wife. Not a good position to be in and our relationship suffered. Somehow I barely kept my urges under some sort of under control and we made it through twenty five years of marriage before she unexpectedly passed  away from a massive heart attack. What I didn't know was all the negative I was facing at the time would lead to new challenges as I transitioned.

The first major obstacle I didn't know I would have to face when I was crushed by the need to communicate with the world as my chosen gender. Essentially what happened was any gender euphoria I was experiencing was very fleeting as I settled into a new gender reality. Interacting with women and men was so new and different. Along the way I was still so concerned with my appearance but I now had to be concerned how I reacted with the world. It was time to face another unknown as I needed to put the entire gender picture together and attempt to live my dream of living full time as a transgender woman. The second major obstacle or unknown was would accomplishing my goal be as rewarding as I thought it all would be.

The great unknown was when I gave away all my remaining male clothes. It was the final symbolic step in saying goodbye to my old male self. It was so different  waking up  and having to be a feminine person rather than just wanting to be a woman on a temporary basis. The first thing which happened was I needed to accept what kind of girl did I wanted to be. As it turned out, it was during this time my inner woman took over. To make a long story short, I was more of a boho style tomboy, than I was a girly girl. I learned whatever the outcome, the transition came so naturally I wondered why I took so long to undertake it. 

As I reach my mid seventies and have less life to live than I have lived, I hope the unknowns will be less noticeable but I doubt it. What fun would that be anyhow?

Jumping Trans Barriers

Image from Shalomi Platzman 
on UnSplash 

 First of all, I never have participated in any sort of track and field events at all. So jumping anything, especially at my age is impossible. In my life, however, I have faced many invisible barriers when it came to being a transgender woman. 

The first barriers were self imposed as were many later in life. The main self imposed barrier I faced was my struggle to free myself from my mirrors who were the only way for me to reinforce my femininity. Sadly, the mirrors had a way of lying to me. No matter how I really looked, the mirror told me I was attractive. When I started to explore the world as my true gender self, I was greeted with many rude awakenings on my true appearance. Trashy, even clownish came to mind when I went out in the world. Fortunately, the negative feedback I received helped me to resolve to do better with my appearance. Slowly but surely I was able to build a small wardrobe of feminine clothes which helped to flatter what I possessed in the body department and led me to jump the barrier of being able to present properly. 

Along the way too, I developed more ways to see if I could truly overcome the barriers I was facing. One of the biggest ways I found was to go to Halloween parties in a "costume" as a woman. By doing this, I achieved a level of understanding of how I presented. Over several years of trying, I was able to make it to a level of being passable as a "professional" woman just getting off of work and attending the party. From there I was able to build a fragile confidence I could survive in the real world if I ever could pursue my dream of living fulltime as a transgender woman. Then, my fragile confidence would help me to jump more of my barriers. 

Also, there were the barriers which were all fake. I found out many existed only in my mind and I was making my own life so much more difficult. I likened it to running an obstacle course in the Army when you had to make split second decisions on real or fake targets. False obstacles included me judging the acceptance or non acceptance from strangers. Those were the times I thought I had acceptance only to have a passive aggressive person stab me in the back. It was all the more difficult because I wanted so badly to be accepted in the world as a  woman when in reality all I should have been looking for was to be accepted as me. Again confidence and a new circle of women friends helped me to get over this major barrier. 

Another point I needed to consider was my choice to pursue hormone replacement therapy or HRT. In many ways, my choice was the point of no return on my journey. Once I sought out a doctor to administer the new medications (and was accepted) the changes began nearly immediately and helped me to conquer more completely the external appearance barrier. As I changed, I learned also how much the hormones would effect my overall being for the better. 

Now, at my age, I am tired of jumping  trans barriers but now have to face the number of new anti-transgender laws in the legislature. In fact, Ohio where I live is trying currently to pass a restrictive rest room bill in the state. All in all, I have resolved myself to doing the best I can and trying to always be sure I am voting for politicians who support me.  It's the least I can do.

Why Now? A Transgender Dilemma

Image from Karla Herandez on 
UnSplash

Every once in a while I see a transgender sister in my age bracket being hassled for starting to transition later in life. 

Since I didn't begin a very serious gender transition until I was in my early sixties, I feel their pain when someone mentions they aren't trans enough. For some reason, the person applying the pressure to be transgender enough doesn't realize why the transitioning person felt the need to wait before seriously going down their gender path. There are many reasons. Primarily, life gets in the way. Examples are many and simple such as families which come along as well as friends and employment. 

I was guilty of considering all of those as I put off finally transitioning. Plus, it was true on occasion, I did enjoy the benefits of attaining a certain level of success in my largely unwanted male world. By male standards I was bringing home a better than average income while I became fairly proficient at managing larger groups of people in stressful situations. I was able to use my spendable income to treat myself and my second wife to dining out as well as attending large select sporting events we both liked. Even though I was treading water as a male, nearly always something was always missing. I wondered how everything I did would feel if I did it as a woman. 

Another point I need to make in why I waited so long to finally complete my gender transition was along the way, I was experimenting with how I was doing as a woman. I attempt to explain away the years I was trying to see if I could make it as a transgender woman as the years I was a very serious cross dresser or transvestite. During my fifty year journey to my gender truth, I could say also the world caught up with me. When I started and for years after, there was no internet or social media to connect others to me with similar gender pursuits. From there I learned nearly anything could be possible if I worked hard enough to do it. I just had to figure it out.

Perhaps along the way, I was a slow learner as I refused to look my truths in the face and see feminine. Gender dysphoria was a huge problem too. Some days I did see feminine when I looked in the mirror and some days male. Which in many ways continues to this day. I was furthered confused by the public I dealt with in those days who referred to me in the feminine sense when they weren't even thinking. What was I to make of that? What I did make of that was they were seeing past my male exterior into who I truly was. 

The simplest answer to all the doubters of my "trans-ness" is get over yourself. Without a doubt I have been a transgender woman my entire life. My dilemma was trying to learn how to express it. 

   

Being the Transgender Woman you Desire

 

Image from the Jessie
Hart Collection

Recently I went with my wife Liz to her latest Doctor's appointment. As I waited I was able to see and judge several genetic or cis women.  It is a past- time I have developed over my many years studying all sorts of women as I transitioned. Along the way I so envied women for many different reasons.

Before I transitioned and began to live full time in a feminine world, I over simplified what I observed from other women. In other words, I was seeing the totality in what I observed in the woman's world. Not the overall layers which went on behind the scenes.  An example was when I noticed a younger woman this morning with a head of curly beautiful hair. Since now I have an idea of all the necessary steps a woman with long hair has to go through for maintenance, I immediately had more respect for the woman I noticed. 

Over the years of changing my gender presentation, hair was not the only part of a woman I noticed. Of course there were the individual parts of a body to consider. When they were all brought together I discovered a new found respect for classic beauty in a woman. On the other hand, I also learned of another very important fact. Even though most women aren't blessed with so called classic beauty traits, just as many have a few of the traits to concentrate on. A very important fact to consider if you are a novice transgender woman or a cross dresser. While it is an exceedingly difficult job to cover years of testosterone poisoning, it is possible to work with any positives you may possess. Legs are a good example. Many male type people are blessed with good strong feminine looking legs which are a good starting point to building the woman you desire. The problem of course is when those same legs are connected to a thick torso and broad shoulders. The real work begins when you have to start hiding the upper part of your body. Before I lost many pounds, I resorted to loose flowing tops and I was still able to show off my legs in shorter jeans skirts. In essence what I was trying to do was direct the eyes down to my legs and away from my torso when anyone noticed me. 

I was also fortunate  in that I had always admired a more statuesque woman so I wasn't (and not)  impressed with the overly thin predominance of thin female models. So I didn't have that to worry about as I went about becoming a semblance of the woman I wanted to be. 

It turned out I was putting way too much worry and thought into the woman I was becoming. My inner girl already had the process worked out for me. Now I see other women for what they are and not what I want to be. I have learned to do the best I could with the cards which were dealt to me. Being the woman you are is a matter of letting her live. I know the process is so difficult for so many of us and I am far from putting myself up on any sort of pedestal. I have learned my lesson when my fall from feminine grace hurt me deeply. All I am trying to say is when anyone asks me when did I know I was transgender, I have always been. She was just waiting to be let out and be the woman she always desired.  

Tennis Anyone?

Image Courtesy Renith R
on UnSplash

 Years ago I felt the need to attempt to copy many of the most popular feminine mannerisms and/or activities I could find. This is a fun post describing one of those activities I was able to indirectly join in on. 

At the restaurant I was managing at the time during lunch we had several women come in for a late lunch and a cocktail (or two). During the warmer times of the year they were avid tennis fans and came in with their very sexy short tennis outfits. Of course, at the time, I wanted my own tennis outfit and be able to go out and show off my legs. 

What happened was, by total accident, I was able to piece together a passable (I thought) tennis outfit with everything in white excluding a tennis racket I didn't have or want. Since I had never really tried to play tennis at all. What happened was I found an all white, lite weight mini dress as a starter point. With it I was able to find all white tennis shoes which were very inexpensive in my size as well as a tunic of sorts (all white) to cover my arms which had tons of black hair I couldn't shave off back in those days because on certain days I needed to wear short sleeves for the kitchen work I had to do.  Hairy arms would not just work with the image I wanted to portray.  I even had to rely on trying to camouflage my hairy legs by wearing two pairs of panty hose as well as adding my own guilty pleasure, a pair of white thigh high stockings.  Because during this time I had agreed with my wife not to shave my legs during the summer. 

Of course, once I had my outfit together, I needed to find a venue to test it out. I finally decided on a nearby mall where I could test my new tennis look with my shoulder length blond wig. Once I got dressed and put my makeup on, naturally the mirror told me I was ready to go and I snuck out the back door while my wife was at work. When I was in the car and out of my hometown,  I began to breathe and enjoy the air on my legs and the drive to a faux tennis match. 

In no time I arrived at the mall, my anxiety over being "discovered" or even laughed at grew stronger as I wondered how I would be accepted. Little did I know during the time I was at the mall, it was nearly deserted. So I was stuck with "presenting" my new tennis look to a few old men who were there to walk around and get some exercise. Naturally, I was noticed and I tried to make it seem I was just in a hurry to pick something up and get back to my tennis. All in all the strategy seemed to work because outside of being stared at (as any woman would) nothing out of the ordinary happened. In no time at all I was back in my car heading home, loving my tennis experience.

These days with all the advanced conditioning available to athletic women, many appear to have developed more muscles with an resultant androgynous look, so a tennis outfit may not be as much fun. One way or another back then, I was able to check the whole experience off my bucket list of womanly things to do as a transgender woman. 

The Good Old Days?

On a Good Adventure in 
Columbus from the Jessie
Hart Archives 

As a transgender woman of a few years, I have a tendency to look back at my life. When I do, often the positive memories out number the negative ones. Of course I remember the benefits of being younger and potentially more attractive.  I had substantially fewer wrinkles as we all do when we are younger but on the negative side, I had more and darker beard growth.  These days I can get away for the occasional close shave every couple of days with no electrolysis ever. 

Then there were all the other days when I seemingly wanted to force my way out of my closet by making very bad fashion choices and ended up being ridiculed by a discerning public. For years I was sure all the public was just looking at me. Heading home extremely depressed to the point of crying most certainly were not the good old days. As with anything else in life, I needed to learn the hard way on how to properly face the public as a feminine transgender woman before I could experience the days I remember so fondly now.

Ironically, so many of my so called positive experiences were more adventures than anything else. Since I was always under a self imposed curfew to be home and undressed before my wife arrived back from her job, I seemed some nights I was literally counting the minutes. Those were the early nights when I was approached by several different lesbians in a small venue I went to often. Perhaps on those adventures I did too good of a job projecting myself as a "lipstick" lesbian where I went with my tight jeans, boots and long blond hair. On the other hand, the more likely possibility was the other women knew what they were getting into and were just considering some experimentation. In those days my old male ego was still with me completely and I was very vain about how I looked as a woman. 

Another reason I had adventures was I put myself into situations where I could find them. I actively sought out venues where the possibility of being harassed ran high, just to see if I could get by. Those were the evenings I had the cops called on me all the way to being asked to leave one venue. Plus the worst night I can ever remember was when another woman verbally assaulted me in the women's restroom by calling me a pervert. Definitely not the good old days. Destiny was kind to me though. Normally when I was at my lowest point mentally with my long drawn out gender transition something came along to encourage me. I would use the term "gender euphoria" but I think all of this occurred well before the term was invented. What was really happening was I was beginning to learn the basics of gender survival I would need to survive a very rocky journey. I needed to learn the hard way being a woman was so much more than appearance. How I walked the walk and talked the talk became so much more important to me. Of course I still wanted to look my best and I kept my weight down as well as keeping my skin as feminine as possible. I began to look at shaving as the ultimate defoliator. 

All we can ask for in life is to get an even break. Even though the good old days may not have been that good, I was fortunate in that I was able to learn from them and survive.     

Life is Too Short

As I went through many years of being a cross dresser, I knew time was running short ( I was sixty) if I was ever going to make the big jump to living as a full time transgender woman. As life went on, two major ideas set in.. Perhaps the hardest one was facing my own mortality and knowing I had lived longer than I was going to live in the future. The writing on the wall was telling me I was entering my senior years and time was growing short for any major lifetime changes such as a gender change. Of course changing my gender involved the possibility of losing friends and family as well as my financial livelihood. 

Photo from the Jessie 
Hart Collection 

The second major factor in changing my gender closet was how natural I felt when I was out of my old dark and lonely closet. Somehow the gender euphoria which flooded over me when I was out and about presenting as a woman was a feeling I had a difficult time expressing. Because there was no one to tell how I was feeling. At the time, my second wife was completely against any idea of me pursuing a transgender lifestyle. Being a pretend male at the time, I did what I was trained to do...hold your emotions in and get over any problem you may encounter. Or, man up and get over it. 

For the sake of saving my relationship with my wife, I did my best to go against my own natural feminine instincts time after time. Finally, the stress I was living under became to much and I tried yet another very aggressive act of self harm. I have written about it several times here in the blog because it is so important to me to spread the word that suicide is never the answer to your problems. Mainly because life is too short as it is and secondly what is true today may not be true tomorrow.

In my case, I learned the hard way to accept my own mortality when close friends and my wife all passed on within a relatively short period of time. All of a sudden, the old "now or never" narrative set in on me with a vengeance. So, after exploring being a woman in all the various ways I knew how, I decided to jump off the cliff and transition. I started with hormone replacement therapy and never looked back. Again the more I explored the world, the more natural I became and felt. It got to the point when I was massively depressed when I had to face the world as a male. Mainly because the hormones stripped away almost all of my male privilege's by making my appearance highly androgynous. Plus, at that point, I hadn't made it to the point where I could sample any of the female privilege's. 

Finally, I got it through my thick, stubborn noggin that my life acting like a man was over. More so because the whole male gender process should have never been undertaken to begin with. The weight was finally taken off my shoulders when I decided once and for all to live a full time feminine existence as a transgender woman. Even then I knew the process wouldn't be easy. The time I spent exploring and learning to find my way around told me to be prepared for more hidden curves and walls on my gender journey. 

On the other hand, I had prepared myself the best I could with assets such as appearance and communication so I could begin the journey. I figured life was too short not to do it. There was no attempting to succeed, I was going to make it.

All Kinds of Transgender Dilemma

 

Image from Karla Hernandez 
on UnSplash

We transgender women and trans men have always encountered plenty of dilemmas as we complete our gender transition, or attempt to. Most of us have friends, family and jobs to consider. Sadly we are considered to be selfish as we pursue our gender goals. Ironically there is truth to the selfish idea because we often need to address our most inner souls to find a path. We found muses were difficult to find.

Dilemmas were everywhere. I know one of my biggest drawbacks to transitioning earlier was trying to figure out how I would support myself. Most certainly I would have had to quit the well paying, hard earned male career I had managed to carve out. None of it seemed fair but who said life had to be fair? As I quote my parents who were fond of telling me just that when I didn't want to do something they wanted me to do.

Another huge dilemma came when I needed to learn the new basics of presenting and appearing realistically as possible in my new chosen gender. The whole process really defined being alone with a terrifying array of cosmetics to deal with. Then there was the problem of what to do about a new wardrobe. Styles and sizes became very important as well as cost. I was in a situation where I needed to hide any feminine expenditures from my wife. I found one big solution by shopping the thrift stores. I could purchase ultra cheap clothes and see if they fit on a very small budget. Plus, I was even able to gather the courage to try an item or two on in the dressing rooms. Finally I was able to dress my way out of my teen girl years and into a reasonable facsimile of what a cis woman my age would wear. Thrift stores not only gave me an excuse to go out shopping, and save money, I could also conquer the appearance dilemma at the same time. 

At the same time, I was ignoring the few friends I had accumulated. Slowly but surely my feminine side was sneaking into the forefront and stealing my life. The more I was in the public's eye, the less male time I wanted. It was working out to be a huge dilemma. The more I accomplished as a transgender woman, the more natural I became and all of a sudden the whole impossible dream of living a feminine life became more achievable. 

My dilemma  of telling friends I wanted to be a woman very much went away when my small circle of close friends passed away close to the time when my wife died. There was no one left to tell. Family, as I have detailed several times, my problems coming out to my family was a different process. Even though my parents had long since passed on, I still had a daughter to tell as well as a younger brother. I had a highly successful experience with my daughter and an equally bad one with my brother who I have not spoken with for nearly a decade now.

My final big dilemma was what to do about my finances. At my age I was getting close to being able to retire on early Social Security. I also owned a house full of antiques and collectibles I could sell to raise money, so I took the early out and retired. All of which of course, did away with me have to worry about job hunting as my new authentic feminine self. With most all of my dilemmas in the past, the door was finally open to complete my gender transition.  

You Wanna be my Girl

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

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

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

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

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

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

Another Transgender First

 From "BeLatina.com":

Latinas continue to break barriers, and we at BELatina are proud to see actresses from our community step forward to be the representation that is so lacking in television.

This time we celebrate the news that Latina trans actress Talisa García will join the cast of the Disney+ series “Willow,” becoming the first trans actress chosen by Lucasfilm.

As reported by Screen Rant, García will play a queen and the mother of Tony Revolori’s lead character in the upcoming Disney+ series, “Willow.”

Lucasfilm’s decision to cast García is not only historic for the production company but the first time in Disney history that an openly trans person will play a cisgender role.