Connecting the Gender Dots

 

JJ Hart, from
the archives.

Many outside of the LGBTQ community, or more precisely the transgender community, think connecting the dots between male and female is as simple as putting on a dress and makeup.

One of the problems is, in order to  walk a mile in our transgender shoes, you have to learn to tie the laces first. Very few people have the patience or understanding to do it. The complexity of gender scares most people off. They think gender is cut and dried but is the opposite. 

Even those in the community have a difficult time connecting the dots and don't realize that even if we have similarities as trans women or trans men, we have just as many differences. Obstacles such as male lives, spouses and sexuality face us as the next dot to connect becomes bigger and bigger or worse yet out of reach.

During my male to female transition, many times, connecting the dots seemed downright impossible and I would never be able to move ahead in my life. My primary problem was my spouse and my male  self were standing directly in my path to gender realization and they would not move or give up their spot in my life. What I did in the meantime, was fall back into a more realistic journey to the next gender dot. An example would be when I began to get out of the non challenging mall shopping experiences and into actual interaction with the public as a transgender woman. 

Many times, the dots would totally fool me when I totally had a mis-conception of what a woman's life would be like. For some reason, I did not think I would be the one whose personal security would be challenged or my intelligence would be diminished when I jumped the gender border into trans womanhood. I was wrong in my judgement and needed to rapidly rethink my path to another dot. Of course I always knew women's lives were much more complex than men's but I did not really know until I succeeded in connecting my dots. 

The frustrating part of my whole experience was two-fold. The first part was I needed to accomplish it on my own with no help and the second part was everytime I thought I had accomplished something, immediately it seemed I needed to accomplish another milestone or dot on my gender journey. It was not until I was accepted in a small tight knit group of women friends did I really begin to make progress in the world. I learned through them, I could validate myself in the world as a trans woman without the help of much of the public, including men. Connecting these dots made my life fun again and so liberating. 

I can not begin to completely describe my experience connecting my own dots because they could be so much different than yours. The one thing we may have in common is, in order to have success in the world, you have to summon the courage to put yourself out there. Of course the problem these days is the concern for your personal safety. You have to be very careful, be aware of your surroundings as any other woman would and connect your dots the right way.       

 

Sitting Pretty

Image from JJ Hart.

It never took me being a genius to figure out my appearance as a woman would cost me much more than my male self ever did. 

I started out my feminine life innocently enough as I began to save my meager allowance to buy a few articles for my girl wardrobe. I even took on a rural newspaper route to add a few dollars every week to spend on whatever I wanted. The problem was, finding my way to a store where I could attempt to spend my hard earned money. 

Our family home was actually in a rural area outside of town and I needed to figure some sort of an excuse to make it into town by myself because all I had was my bicycle. I figured out the answer which came to me when I was asked to go in town and visit my Grandma. She just happened to live very close to the downtown area and probably would not resist any attempts on my part to go downtown alone. I knew also, there were several stores downtown which sold makeup as well as other feminine accessories. So close but so far.

Predictably Grandma didn't and I had free reign to go shopping on my own. Then, the next biggest hurdle came along when I had to actually go into a store and shop for any makeup I found that may be suitable. The first time I was brave enough to shop for my own makeup, I was panicked and just wanted to buy something and get out of the store. Another problem was my Dad worked a short distance from where I was shopping and if I was caught, I would have no answer to why I was buying makeup. He never did catch me and the only hurdle I needed to face was the clerk who would be checking me out with my purchases. 

I was able to visit Grandma and do my shopping with no problems except for my extremely limited financial resources. Even though I managed to buy appropriate makeup, panty hose and even shoes, there was no way I could ever afford a suitable wig. For years, the wig of my dreams was just a fantasy of mine. Even so, time flew by and I managed to survive, even with my gender issues. It wasn't until I was out of the military did I realize how much sitting pretty would cost me. 

Dressing head to toe as a woman still proved a challenge for me to afford. Most of my needs would be met by going to thrift stores in our area. By doing so, I was able to find fashion "treasures" which were added to my growing wardrobe. While the thrift stores were cost effective for me, so many other aspects of cross dressing myself were not. Due to the size of my feet, thrift stores were out and I needed to shop retail. The whole process of adding new makeup, accessories such as purses and jewelry was a challenge because for the most part, my wife had control of the family finances. Through it all, going to a wig shop and buying a wig was still very difficult and frustrating. What I mean is, once I was able to put together a quality outfit, I was still struggling with having a wig to finish off my look. 

Finally, my financial situation improved to the point where I could afford a quality wig but then I needed to figure out which wig I could buy. Initially, I was like a kid in a candy store and picked out the wrong wigs which made me look like a clown. Through all my fashion errors when I was out in public for the first time, I finally was able to buy the correct wig which fit me well and framed my face correctly. It turned out the wig was the final piece of my presentation puzzle. 

For the first time ever, I was able to do my best and sit pretty as a novice transgender woman. 

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine. 

It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Options or Paradise

 

Liz on Left, out to eat! 

During our gender transitions, many times we have the choice of options or paradise. 

Often, options come about as not being a choice. Examples include all the days we had to rush around and hide our feminizations from our family and friends. We had no option but to hide our truths. For some if us also, our cross dressing options never became any better when we had to pursue stints in the military. Certainly, the military provided every roadblock in the world for pursuing any route to paradise for gender conflicted individuals. 

As a whole, back then, paradise was very difficult to achieve. In fact I can now refer rare paradise as gender euphoria. For many years and even decades my gender balance never changed. I was still sneaking around risking life as I knew it to momentarily express my true inner gender. Fortunately, I had the time to work on perfecting my femininized presentation. When I finally was able to pursue paradise by going out in public, I was closer than before to achieving success. In fact, once I learned to blend in with  other women in the world, I was more likely to find a fleeting sense of paradise. 

Usually, my paradise did not last long because I needed to quickly return to my male world which I was increasingly feeling uncomfortable in. I was desperately seeking other options to find more gender euphoria other than the annual Halloween parties I was going to as a woman. The parties and the transvestite/ transsexual mixers I started to go to helped me to understand the gap I was facing when I considered the ultimate outcome of where I wanted to go with my life. Instead of just embracing the usual male attributes in life, I needed to include the very real possibility I would have the option to live life out as a transgender woman. The reason I thought this way was I encountered paradise when I was experiencing the world as my true authentic self. I felt so natural and wondered why I had waited so long to do it.

What if I had experienced paradise a decade earlier than I did when I went to a TGIF restaurant and bar determined to mix with other single women. Maybe I was just waiting for the world to catch up to me but more than likely the opposite was happening. I had the options to catch up to the world and I took the chance. By the time I ventured out into the world, I had certainly paid my dues and was  ready to reap the benefits. 

Still I was frustrated when the benefits of my new life were just out of reach. Such as the times when I was so comfortable in my new feminine world I actually forgot where I was and caught myself slipping back into a male mode. I still did not have the full closure from my old male self I so desperately needed. I kept running into unexpected roadblocks and stop signs on my gender path such as a spouse's death which changed my ideas of where I was headed but not for long. Soon with fewer and fewer options to consider as well as a solid new life I was building, paradise was closer than ever before. 

As transgender women or trans men, we often experience periods of options or paradise as we follow our difficult, unique gender paths which separate us from other humans. The whole journey hopefully makes paradise worth it.  

Affirmation

 

Recently I had a very important reminder of my initial affirmation as a legal female in the world.

It came several years ago when I decided to have as many legal documents as I could changed to reflect my authentic feminine self. One of the major documents I needed changed was my Ohio driver's license. I made sure I acquired all the name change documents plus a letter from my therapist to insure I did not have any problems. The process was scary but exciting because among other things, I needed the picture ID of the license so I could vote. 

It just so happened my license was due to expire just ahead of the all-important election coming up in November so it was important for me not to procrastinate until the last minute so I can cast my vote against tRumpt. 

In many ways, being able to renew my license symbolically was similar to renewing my gender vows with myself. As far as completing the process, it was easy this time because I was already in the system as female and no one questioned me. Probably the most difficult part was having my picture taken because of all the insecurities I feel when it comes to my appearance. For the morning I chose one of my most feminine tops, applied a foundation, eye makeup, lipstick, blush and tied back my hair and was ready to go. I arrived early and only had to wait approximately fifteen minutes before being waited on. 

Even though I knew the process would be nearly painless, for some reason I was still suffering from needless paranoia. I was able to put it all behind me and reaffirm  myself as a legal transgender feminine person. 

Next stop is my upcoming mammogram appointment which is in the process of being scheduled now. I consider mammograms as a slightly unpleasant rite of passage I need to go through since my maternal grandmother died from breast cancer years ago.

Affirmation is good.

Gender Shape Shifter

 

Witches Ball Halloween
Image,

For years I obsessed with  the idea I basically was  just a shape shifter between my male and female selves. 

All of this coincided with the time I spent as a very serious cross dresser. Basically, all if my idle thoughts were grounded in my feminine appearance. Time I wished I could get back. As my feminized presentation became better, the more I felt more than just a shape shifter. Especially when I began to explore the world as a transgender woman.

My gender ideas were changing primarily because I quit thinking I was fooling the world and began to know I was living as my authentic self. So if the other person was a transphobe and did not like me, it was their problem, not mine. My mind had made a difficult yet important shift when I began to believe in myself. 

At the same time, ironically, my shape shifting became easier. I became more comfortable in the world and at the same time more confident. I found confidence to be my main feminine accessory. Much more so than my favorite jewelry, heels or wigs. Looking another in the eye was much more important when I used the women's room and other places I needed to communicate. Without confidence, I might as well just stayed home and watched television with my miserable male self. I was not shape shifting any longer, I was me.

When I did, I found I was so much happier and I wanted to push the feminine envelope I was living farther and farther. It was all good, until all of my actions put me on a collision course with my second wife who never approved of any ideas of me transitioning any more into a transgender world. I had put myself firmly between the rock and the hard place when it came to my gender issues. To attempt to survive, I did the best I could to live out my dual life I was living. I would over achieve in my work world as a man, then at the same time try to explore the world as a woman.

The more in-depth I became living a dual life as an accomplished shape shifter, the more pressure I felt to do something about it. In the meantime, I was doing things such as shopping for my wife's Christmas gifts as a woman. When I was successful, I was encouraged to do more and more as I suddenly began to feel secure in the world. 

Finally, I came to the point when I cross dressed as a man, I felt foreign as if I was shape shifting again and wanted no part of it. Happily, by that time I was able to try gender affirming hormones which femininized me even further. I enjoyed the effects so much, it was an easy decision for me to never go back to my male world. Being free of gender shape shifting was quite the enlightening experience. 

Transgender Guilt

Image from Civil War Cemetery
Cincinnati, Ohio.

 For many years I felt guilty about having my gender issues.

After all, I felt so alone in my desire to leave my male self behind and live in a feminine world. Not only was I alone, I even was scorned when I tried to express my desires. As I grew through the stages of being a weekend cross dresser into a novice transgender woman, I waited for the guilt to go away or at the least diminish. It never did. In fact, my guilt increased. 

Factors arose such as what would I tell my daughter and my wife, all the way to how I would manage to support myself and my family when it seemed I could lose everything if I transitioned. Selling my life out to be a woman seemed at times to be such a selfish idea and I felt guilty. So much guilt, it stressed me out so badly it wrecked my already fragile mental health. I would not have wished my gender problems on my worst enemy and even a bigger problem I had was there were few people I could even talk to about it. 

Sure, I had a therapist, but even then I felt guilty of sacrificing my masculinity and talking about my inner feelings. I had a gender storm inside me I could not get out and I was stuck between a cruel rock and a hard place. The reason was I was trying to live in both of the main binary gender worlds. For three days, I was learning if I could exist in a feminine world and in the next three days I had to go back to my boring male world. On the extra day, sometimes I lived in both genders, at least in my head. Of course doing all of this did nothing to relieve the guilt I felt on how I was living my life.

The more I lived my life between the genders, the more I could see what was coming. I was lying to myself when I tried to tell myself my inner woman was winning the contest for my soul. When I was spending my three days experiencing life as a trans woman, I felt more alive and excited about my future than even before. At the same time, I still felt the doubt creeping in about if I could make it at all. Perhaps freedom from guilt was on the horizon if I could just make it. So, I kept trying different things to enhance my future.

As I always point out, my male self pulled out all the stops and threw in guilt as one of the main weapons to keep the status quo he always fought for. As he fought, he made sure he brought up all of the fond memories of the time we spent together. 

Finally, his efforts proved to be to no avail as I started to put together a new life as a transgender woman. It turned out he could not compete with my truth, I had always been destined to be feminine. It was an unfair fight, guilt or no guilt. I could take the battle no longer and gave in before the stress literally killed me. I will forever remember the night when I gave in to my feminine side and decided to research if I was healthy enough at the age of sixty to undergo gender affirming hormone therapy. Which would signal a point to me which I could never to back to life as a man. 

From that point forward, I was able to give the remainder of my male clothes away along with the guilt they carried with them. I moved forward to legally changing my name and all the identification documents which could be be legally done in my state and with the Veteran's Administration. I was doing my best to put all the transgender guilt as far as I could into my rear view mirror. 

Kissing as a Contact Sport

Image from Brian Kyed 
on UnSplash

As a transgender woman, I have been at the crossroad many times of to kiss or not to kiss.

Before I proceed, I need to point out, all of this happened before I moved in over ten years ago with my wife Liz here in Cincinnati. 

The first time I was almost kissed as a woman was when I was entrapped by a much bigger than me trans admirer at a small party my second wife and I attended in nearby Columbus, Ohio. He cornered me in a small hallway and for the first time in my life I felt powerless to fend off another human being. Before he came in for a kiss, or so much more, I was rescued by my wife who told me not to wear such a leg revealing dress anyway with my long blond wig. Of course I did not listen and paid the price later on the way home.

Along the way, as I transitioned, I did kiss a few men, mainly to see what it was like. I was attempting to see if my sexuality was going to change with my gender or not. The interactions were few and included two date nights in the regular venues I went to plus another with a guy I met in a coffee shop. The dates ended up being one time affairs which was sad because I had a good time being validated as a woman by a guy but the coffee shop guy turned out to be multiple meetings before we went to his house. We did kiss passionately before he let it slip out he was married. When he did, I slipped out the front door, never to return. 

The only other man I had a crush on and wished he had kissed me was the big burly, motorcycle rider I befriended after his very short lived marriage to a woman I knew briefly. It turned out I was the only one in the group who didn't disown him and we became friends. But not good enough to be asked to ride on the back of his bike or be kissed. Very soon after I got to know him, he transferred jobs and I never saw him again.

From then on, it was back to kissing women for me. During the lesbian mixers I went to, I was kissed by several women I did not know and I was flattered. Along the way also, I did sneak a kiss in with my two party women friends and one was very sweet. Again, sadly a future relationship with all its complications was not to be and we both moved on but still stay in touch to this day.

All in all, kissing a man turned out to be a duty for me. Something which should be done in return for validating me as a woman. But the overall thrill or charge wasn't there to enable me to want to change my overall sexuality. Plus, I did learn how frustrating it could be to be wanted and not the person who was the pursuer. I found the other gender grass was not always greener, especially when I was basically trapped by a person much larger and stronger than me. 

It was all a lifetime learning experience of learning the ins and outs of kissing another person from both sides of the gender border. I learned my preference was always kissing a woman. As a woman. Especially when gender affirming hormones' gifted me with my own set of breasts to enjoy. Kissing as a contact sport became more fun.

The Lifelong Question

Image from Shifazz
Shamoon on UnSplash. 

During my life, I have had several burning questions. One of which of course was how I ever made the determination I was transgender.

Before we get to the main question, we need to examine several of the other issues life threw at me and possibly you also. The first direct non gendered question I encountered was the Vietnam War. Or, how was I ever going to negotiate serving time in the military, as I risked my life. As it turned out, me serving my military time turned out to be a gender question too because the closer I came to being drafted into the Army, I began to resent the fact women did not have to face the draft also. All in all, a waste of time, so I gave it up. As it turned out my service in the military had far reaching positive consequences for me because among other things, I met the mother of my daughter there. 

Another question arose when I was not so blissfully cross dressing parts of my life away and I wondered if I was the only one with similar gender issues, I was stuck in the pre-internet dark age of having very little public information available to me. It wasn't until I served my time in the Army did I discover there were indeed many so called males who wanted to be femininized into women. The problem became was what was I ever going to do with my new family. Certainly, fathering a daughter had not made me more of a man, No matter how macho I acted. 

The older I became, it seemed the more complex my problems became. In fact, my thirtieth birthday was the most difficult for me to negotiate of all my birthdays. At the place I was in then, I was in deep despair over what decisions I would have to make to survive. What I determined was I needed to find better employment, stop drinking as much and resolve to be a better father. I was a success at finding better employment but a dismal failure at curtailing any of my party life, which included the Halloween parties I was going to dressed as a woman of course. All I really did was procrastinate further on the major question I had which were my gender issues. 

When I began to complicate coming out into the world as a transgender woman, I first had to determine in my own mind if I was indeed trans. Once I did, I needed to figure out who I would tell. Since most of my immediate family and closest friends had passed away, the list I had accumulated was very short. First to tell was my daughter, my only child and I suffered long and hard with if I should tell her at all. My reticence was rewarded with relief as she accepted me without question and still wanted me to be involved with my grandchildren's lives. I also questioned coming out to my only brother because I knew his in laws were religious right-wing bigots of the first degree. We both went our separate ways over a decade ago. 

The more life progressed, the tougher decisions seemed to be because there was more to lose. Another primary example was my job which I had worked very hard to be successful. I knew the company I worked for would never accept a transgender manager, so staying put was out. Fortunately by this time, I was old enough to be within reach of taking my social security retirement. So I just retired and started gender affirming hormones. 

The lifelong question of why me mostly answered itself. I played the odds throughout most of my life and was for the most part successful. For better or for worse, I was able to hide my true gender feelings until I could safely transition. Along the way, I also found I may have never had the chance to decide my gender anyway. My Mom had suffered through several still births before me in the late 1940's and had taken the DES medication. DES as I have read flooded the womb with estrogen and has been linked to the possibility of causing  transgender children. Who knows? 

Having all these major questions in life is just another facet of being human. Some questions are more difficult than others. 

Never Going Back

Archive image. Liz on left.

Once I started down the road to living my dream as a transgender woman, I found I could never go back.

I am sure it all started the first time I viewed myself in my Mom's clothes and makeup in the mirror so many years ago. All I knew was something clicked inside me and I enjoyed the process immensely and couldn't wait to do it again. Going back to my male self became increasingly difficult. 

It stayed a problem the older I became as I began to be better with the makeup and fashion choices I could find. I even went as far as shaving my legs when I was young to get rid of the hated hair which came along with my unwanted puberty into a testosterone poisoned body. Still I persisted living a secret yet powerful life in the mirror as a girl. Through my often clownish makeup, I could still see my authentic feminine self peeking at me and I loved her. 

Over the years, practice made perfect and in many ways I was able to cover up my male body and present well enough as a woman to try out the world. Even though I took many bumps and bruises along the way, I persisted and small victories helped me to want to never return to the male life I never really wanted. Every now and then I was able to be successful in the world as a novice cross dresser. Still not understanding I was so much more than wanting to just look like a woman. I wanted to be a woman. Cross dressing was a welcome bridge to getting me to the big picture of my life, my desire to be a trans woman. Once I came to the point of wondering just where I fit in with my big picture in life, then I needed to see if I could make all the needed sacrifices to get there. All of my "secret" adventures as a transgender woman could cost me all I had worked so hard on in my male life. If discovered, I could lose my marriage, family, friends and jobs. As you can tell, a lot to be considered.  

During that time, destiny kept setting in and deep down kept telling me I could achieve my ultimate gender dream. Every blind corner I turned and every step I climbed on my path was showing me the way as I carved out a new life as a transgender woman. All of a sudden, my doubts started to disappear I was succeeding more and more when I sought to flip my male life to female. I even began to go to the same venues I went to as a guy with little to no problems. When I did, deep down I was terrified of losing my life as I knew it but on the other hand, I knew I was never going back. There was no way.

By the time I decided I was never going back, my decision was made so much easier by several things. Including unconditional acceptance by my daughter, the very few friends I had passing away and not having a job to worry about (since I was able to retire) made my decision so much easier. Even my very stubborn old male self could see no future and he faded away as I took the final steps to completing my gender transition. I even was able to solve my marital situation the hard way when my un-approving second wife passed away and I unexpectedly became involved with a very supportive third wife who loves me for who I am. 

I believe pushing forward and never quitting was something I learned from my parents. I am sure they would have never envisioned their teachings turning out this way with me.

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. 

  

Bonding with Yourself

 

Club Diversity Image. Columbus, Ohio

As strange as it may seem, it took me many years for me to fully bond with myself as a transgender woman.

For years I wondered if I was a woman or a man. Everyday was like groundhog day when I woke up in the morning. Some mornings I felt more like a girl and others as a boy before the reality of my existence set in. No matter how gender fluid I felt that day, I needed to be ready to compete in my unwanted male world. I wish I could say the competition just made me stronger as a male but it never did. Most of the time, the competition just made me want to head home and cross dress as a girl. Plus, I was put into an even deeper frustration place when my brother was home and I didn't have any privacy to try on my feminine wardrobe. 

Bonding was difficult when I was not allowed into the feminine world at all and was destined not to until much later in life. In the meantime, I struggled from one gender struggle to another, All the time, hiding my authentic self from everyone in the world. I suffered so much, I needed all the help I could get to maintain my life as a man and still have any sense of stable mental health. Especially when I was diagnosed with having Bi-polar depression. If you are not familiar, I suffered from terrible highs and lows. When I was up I could do anything. Including transform myself into an attractive woman and when I was down, all I wanted to do was lay in bed and sleep and try to drown out my gender issues with alcohol. Finally I was diagnosed by a therapist and was prescribed medications to help me out.

As we all know, the medication has not yet been invented to relieve the pain and tension of having gender dysphoria. Even now I suffer from dysphoria when I wake up in the morning and look at myself in the mirror. After all these years, I have learned to take the good along with the bad and take the middle road. It has been a good coping mechanism for me. Along with those mechanisms, I learned other ways to structure my life so I could finally bond with my myself. When I did, I found I was a stronger human because I had the chance to experience life from both sides of the binary gender spectrum. Since it is the rare individual who can claim to be all male or all female in the gender spectrum, I was able to find my special place where I could exist in society. The question always was, was society ready for me or any other transgender woman or trans man.

I quickly discovered most of the world did not care if I was trans or not. They had lives to live and were busy doing it. On the rare occasions I did encounter a negative transphobe, my strong personal bonds gave me the confidence to survive. 

Again, bonding my unwanted male self with my stronger, more natural female self took me years to complete. Mainly because I did not have the courage to admit who I was to my true self. Once I did close the gap, my long awaited bond was complete and I could move on in life as a total person as a transgender woman but never forgetting the man who helped get me here. A topic for another blog post. 

There is Always a Transition

 

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Jessie Hart

In an expansion of yesterday's post, today, I am beginning a post on the extra transitions we go through in life. Many are relatable to everyday life, some are not. Everyone goes through changes or transitions. For example when and if they ever become parents.

My biggest transition came when I crossed the gender frontier from viewing myself as a cross dresser I could possibly live without to a fulltime life as a transgender woman. My transition also came along when I was negotiating raising a daughter, building my career and attempting to outrun myself. Life became very busy as I struggled to find myself. I resorted to therapy to try to balance my mental health. Along the therapy path, I was diagnosed with a Bipolar depression disorder to add on to my gender dysphoria which was dominating my life. Through medication I take to this day, I am able to control my depression and my gender dysphoria became much better when I finally decided to fully leave my gender closet. 

As I lived on, maybe I should have taken up the motto, "Later is Greater" as I took my time exploring the possibilities of living a totally femininized life. My excuse is I wanted to make sure I had it all right before I risked it all and left my male self behind. Eventually, I learned from all the trips I was making out the door of our house, doing the best I could to blend into the world as a woman, transgender or not. Then, another transition was facing me head on. It was the great leap from being an experimenter to being a doer or practitioner of being feminine. I took years of watching and learning to understand what my second wife was telling me when she said I didn't know anything about being a woman. Not only was she right, she did did her best to hold me back from learning what she was talking about. There was no way she wanted to show me much about what truly being a woman was all about. Instead, she persisted in calling me the "Pretty, pretty princess."

Her failure to help me just pushed me farther and farther towards my next transition which was a huge one. The more I settled on a feminine look and style I liked, people I previously didn't know began to recognize me and I was forced to begin to build a whole new life as a trans woman. Primarily it meant I needed to communicate with the world with tools which were totally foreign to me. Trying my best to develop a softer feminine sounding tone was a real challenge along with adjusting to a society of women where passive aggressive behavior was the rule. There were too many times I suffered when I didn't perceive exactly where the attack on me was coming from. Instead of usual male frontal attack I was used to, I needed to start watching my back. Communication with the world was a huge part of my next gender transition. 

After I thought I had the communication and appearance transitions down, seemingly there was another challenge awaiting me at every turn. Who knew it could be so difficult to cross the gender divide? I was often frustrated when the smallest details would trip me up, not to mention the big ones such as the ill advised use of water balloons as breast forms. The balloons worked well enough until one exploded on me one night in a venue I often went to. Fortunately, I was on my way to the woman's rest room when it happened and it was empty. I was able to clean up,  quietly finish my drink and leave with no one noticing me, I was wearing a loose fitting top so no one saw or mentioned the one breasted wet woman on her way out of the venue. Needless to say, my next investment was silicone breast forms. 

As I near my seventy fifth birthday. transitions are harder to come by yet more meaningful These days, I mostly just present as old. Plus, my ultimate paranoia of having to go to assisted living and having my gender attacked looms large. As I always say, I need to do my best not to dwell on the future and live in the present. 

None of us control the final transition, no matter how much money or power we have. It is up to any higher power you believe in to make it happen..   

Trans Acceptance

 

Liz on Left, Daughter on Right.

Today, my wife Liz and I are heading north to Dayton, Ohio for a family birthday party. The party is for my youngest grandson and my daughter's father in law. 

The get together of my daughter's extended family has always been a different experience for me, as a man or a woman. Per norm, my visits as a man were ego driven with battles with my son in law in particular. They were nothing as compared with any other macho activities I faced with the family.

When I completed my male to female gender transition, I wondered how I would be accepted. If at all. It turned out as my daughter led the way, the rest of the family followed. As most of you regular readers know, my kid was wonderfully supportive from the very beginning. However, as her family expanded to three grandkids for me, what would they think of my gender issues. Spoiler alert, all three took my transition in stride and my oldest grandkid even came out as transgender before "they" left high school. They (chosen pronouns) were always leaning that way, so I was not really surprised.    

As time and events went by, my feminine self was still chosen to stand up in front of a temple and actively participate in one of the bar mitzfah ceremonies since my daughter converted over to the Jewish faith. Her decision led me to a whole other level of acceptance I never knew existed. From the Rabbi, to cousins I never knew before, I was accepted as an equal person. No one cared.

Now when we make the hour trip to the birthday party, I have nothing but good feelings. At the least, transgender acceptance as a person helps my gender euphoria, at it's best I get to see my trans grandchild again. Plus, I get to moderately dress up for my first wife who usually attends as she is the mother of my daughter. Recently she gave me a complement which literally left me speechless. She mentioned how good I looked and how far I had come along. Now I feel bad, I couldn't come back with anything else than a mumbled thank you. She went way back with me to the Army and she knew I was a cross dresser before we got married.

Since now I am close to the oldest person in the room, never in my wildest dreams did I ever think I would ever become a matriarch.   

Is Being Trans all About You?

Image from Caroline Hernandez on UnSplash

 As I was embarking on a struggle with my second wife concerning me coming out as a transgender woman, we encountered plenty of problems. It was  during this time, she was fond of telling me my gender issues were not all about me.

Ironically, for the most part she was right. As I ventured more and more into the public's eye, all I thought about was the next opportunity I would have to go out as a woman. Then, when I had to go out as my boring, unwanted male self, I would become upset and get mad when I tried to internalize my thoughts. I have written before about the vacations I ruined when all I thought about was how I would spend them as a woman. 

Worst yet, I was jealous of the fact she had the body and life I wanted to have. I wanted her curves and soft skin and wanted her to make love to me as another woman. Which for the most part never happened. The whole process carried over into my life as a cross dresser or novice transgender woman. When ever I went out into the public, I felt as if every eye was on me. Which for the most part, was not the case. I found most of the public was just going about their everyday lives and could not care less about me and my issues. It took me years to learn I could just blend in for the most part into a feminine based society and basically just disappear

First, I had to work my way around the fact my male ego still controlled the way he wanted me to look. He wanted me to dress to thrill, which just turned out trashy and attracted unwanted attention. It was quite the learning experience and took awhile to accomplish because of one big reason. I wanted so badly to be a pretty woman but just couldn't accomplish it primarily because of my testosterone poisoned body. As far as anyone had ever told me, my legs were the only feminine part of my body I had to work with and my wife was no help because she never helped or complimented me on anything I did. Once again saying my attempts to be pretty were all about me.

When I could not disagree, I just became more frustrated and the pressure was on to do better as a femininized person...with or without her. It was at that point, I did my best to escape the house without her knowing and see the world through the eyes of a transgender woman. I was modestly successful and when, on the other hand, when she discovered what I was doing, huge fights happened. Fights, I never won, because I knew she was right. I was risking everything we had built to experience a new exciting but scary world. After I figured for sure I was indeed transgender, the pressure on me really began to build. On one hand, I suddenly could see a dream I wanted my entire life may be accessible but on the other, I would have to lose everything I had worked so hard for to grab it. It seemed life was so unfair but I could hear my parents telling me, no one ever said life had to be fair and I moved on.

Sadly, my wife passed away before I faced my truth with her and she knew it more than I did. On more than one occasion following a big fight she told me why did not I do us both a big favor and transition. For some reason, I followed the male way out and tried again and again to internalize my feelings until I was intensely unhappy. It seemed being trans was all about me until I finally came out and accepted myself.

When I did accept myself as transgender, I was able to see the world from a different viewpoint and learned to love the world and others more deeply than I ever had before.

Young and Dumb

 

Banquet image with Liz on left. 

I often wonder how wise I was when I decided to follow my gender path to becoming a full time transgender woman. In many ways, I am referring to the good old, if I knew then what I know now, would have I done it.

The short answer is most certainly I would have tried my best to follow the same path because I had no choice. Either I transitioned or I died. I made it so simple even the most extreme transphobic person could understand.  

Transgender or not, we all go periods in our life when we are young and dumb. Fortunately, most of us live through this process and learn from our mistakes. This is especially true for transgender woman or trans men as they go through an assimilation process leading to living as their authentic selves . In many blog posts, I document more than a few of my fashion and makeup  mistakes when I first started my journey out of my dark gender closet. It wasn't until years of experimenting with my makeup did I seek out professional help which happened at a cross dresser - transgender mixer I happened to go to. I put my ego aside and volunteered for a professional to redo my makeup. He did a tremendous job and even explained what he was doing so I understood as he went along. I was very impressed with the results and basked in the praise I received from others I met. I went from a casual believer in the power of makeup to a total devotee.

Even when I was young and dumb, I tried to conduct myself with some sort of grace and decorum. I made sure I distanced myself from the other trans woman who was flashing others at the Andy Warhol show we went to in Columbus at The Ohio State University as well as making sure I did not abuse the rest room privileges other cross dressers did at a gay bar we went to. Leaving the toilet seat up and urinating all over the toilet in the women's room was certainly not cool and was nothing I wanted to be associated with. It wasn't too long after that when the sign went up on the door...real women only.

On the other hand, I still did quite a few dumb things which could have gotten me into trouble when I was in my formative cross dressing years. I drove way too much after I consumed vast amounts of beer was my main sin as well as how I dressed when I first came out into the world. My trashy fashion sense was just screaming look at me when the best policy was just to blend in with the world. My other problems I was lucky to escape happened when I ignored my new personal security needs as a transgender woman. No longer could I fall back on my departed male safety privilege and I needed to watch where I parked and what I wore around certain people. I was bailed out of one close call by my second wife and another time, I was able to buy my way out of trouble with two men I encountered on a dark urban sidewalk when I was leaving a gay bar.

I always have been a believer in that I have always had some sort of a guardian angel looking over me and she was certainly helping me out during my self destructive coming out days. I am sure, many times she was shaking her head and saying not again. How I was driving in those days alone many times could have resulted in a very serious injury. 

As with anything else, if you are transgender, life has given you extra layers of existence to work your way through. You need to deal with life's normal problems along with a whole new set of others which often are completely unexpected. Crossing the gender border can often be brutal at the hands of the public which chooses not to support us at all. Which we will find out again with yet another major Supreme Court decision coming up soon. Too many people didn't make it through the young and dumb period of their lives and are now old and dumb. 

Strong Women Role Models

Hand Beaded Transgender Hair
Barret from Liz T Designs on
Etsy 

 I am speculating most transgender women or even trans men have experienced at least one or more strong women in their lives.

For any number of reasons, women have been forced to be strong and carry the load for weak men. For many, their first entrance into true womanhood comes with having children. With current economic conditions the way they are, the days of the old fifties version of Mom staying home to raise the kids and take care of the house is long gone. To barely make it financially, both partners have to work.

Problems then arise when the man still wants to follow the old outdated male standards of doing very little around the house to help out. 

By now, you may be asking what does this have anything to do with being a transgender woman. With me, at least, it means a lot. My Mom worked out a deal with my Dad in the sixties. If she went back to work as a school teacher and used her college degree, my Dad would help her out with hiring a part-time housekeeper. Even with the help, Mom had a lot to do with two sons in a very male orientated family. Even though I admired my Dad for being a self made man coming out of the Great Depression and WWII, I had more on hands experience with my Mom who was very headstrong. Who knows, maybe that influence with her had more to do with me being transgender than anything else. Later I was to learn my gender issues ran deeper than one person outside of myself.

Even so, I still searched for the perfect woman to model myself after. I wanted to appear as the confident women in the world I saw moving around in their lives. The older I became, the more I learned the perfect woman did not exist and many women were hurting themselves attempting the be a successful person in the world as well as on the home front. Not to mention, the overwhelming problem of appearance. Until recent times, aging has not been kind to most women who among other things suffer from extended menopause. 

All of these factors contribute to why I have such a high opinion of strong women and how I think the world is changing quickly as many more young women seize the new opportunities in the world around them while young men play video games. 

With all the changes, it is important to figure out how a transgender woman can fit in at all. Certainly, we have to be a better woman to do it at all. Which means understanding all the layers of a woman's life. That is once of the reasons some women resist letting trans women play in the girls sandbox at all. As my second wife always told me in no uncertain terms, I needed to earn my way in. Maybe that is why I never considered her a strong woman role model for me at all. My Mom on the other hand, was a strong role model for me. From how she applied her makeup to how she battled me for my future, I appreciated all she did for me. Including of course, birthing me. She remained my role model even though she rejected me when I came out as a transvestite to her. She immediately said she would pay for a psychiatrist which I rejected. Since I didn't have a mental health problem because of my gender issues. 

We never mentioned my desire to change my gender the rest of her life but even so I decided to adopt her first name as my legal middle name when I transitioned and legally changed my name. It was the biggest honor I could think of for all the things she did for me. The most relevant thing she did for me was to show me what a strong woman was and how to be one. A trait I would really need as I followed all the ups and downs of following a new gender path.

It is ironic to me, the strongest women I know like Liz or Kim have very little idea of how much they have helped me along and the most frustrating part is I don't think I can ever repay what they have done for me. 

Who knows? You might be an offspring of the very few strong women like my daughter. She had to became an ally for her trans child and was then able to take advantage of helping her child at an early age. Maybe your Mom realized your authentic gender self and became an ally rather than the cruel opposite.  If you didn't, you were forced to do what the rest of us did. Study strong women close up and do your best to join their ranks. I was fortunate enough to be able to work professionally along side several strong women who I learned from. The women seemed to combine strength and humility seamlessly to forge a successful business career. 

There are so many variations on how to become a successful strong trans woman it is difficult to mention them all. We all need to the do the best we can to force our way into a world where sometimes we are not wanted.

Owning Who you Are

Image from the Jessie Hart
Archives.

During Pride Month, it is extra important to to own who you are. Just as much as it is anytime but Pride may give you the little extra confidence to get by. 

To a large part, confidence in yourself, plays a huge role in you being able to own who you are as a novice transgender woman or trans man in the world. For me, it took many setbacks before I gained the confidence in myself to enter the public's not so accepting world. Just learning the basics of fashion and makeup was a major undertaking for me since like so many of you, I was starting from scratch. Slowly but very unsurely I was able to learn the basics enough to get by. In order to do so, I needed to learn to blend in with other women and not try to be sexier, which was a dismal failure. Stuffing a male, testosterone poisoned body into an ultra short mini skirt or dress just didn't work anywhere except for shock value at Halloween parties. 

Once I began to develop a slight amount of confidence in myself, I still learned the hard way that the sky was not the limit when I came to exploring a new life as a transgender woman. In one venue ( a  TGIF Friday's) I found myself becoming a part of a small diverse group of strangers who knew nothing of my old male life. The group was a mixture of a lesbian and her friends which included a beautiful exotic  dancer who drew the interest of a big bearded guy who owned a motorcycle and managed a lumber yard just down the street. Against the wishes of the group, he shocked everyone by proposing to the wild dancer and found himself in a short lived ill fated marriage. Ironically, I was the only one who showed him any sympathy in the group and we became close, before he moved on with his motorcycle to another job. The whole episode gave me confidence in the fact that men were not as off limits as I thought they were. Even though they were not knocking my door down to date me.

I found out quickly my sexuality did not change as I transitioned from male to female and even was enhanced when I learned all the attention I could get from other women. Most importantly, I did not need the validation from a man to give me the confidence to be myself. Even though I was prepared to see if there was any sort of a sexual spark between the authentic trans me and men, there just wasn't. I was busy owning who I was and she was doing a quality job during the process. As it was, the process led me down many different paths. Many turned out to be good and others were dead ends but my new found confidence helped me to continue to search.

Owning who I was also meant forcing my old, unwanted male self into the closet where my authentic gender self lived for years just existing by cross dressing in front of the mirror. Of course, he put up quite the battle before losing and nearly wrecked my mental health on the way. With the help of a key group of women friends and a loyal, dedicated therapist, I survived on my gender path and eventually thrived. I just had to muster up more courage than I thought I had to do it. To those of you who would ask why I would risk so much to transition, I can only say the process along the way felt so natural and saved my life. 

Some would argue I am less trans than the next person because I waited so long to come out in my life. That is ridiculous because I always knew I had gender issues but did not grow up in an easy time to express them Plus, I would not give anything to have missed out on certain moments of my male life, such as my daughter. Who has led me to having three grandchildren I love very much. So you can see why I don't consider my entire male life to be a waste of time because I learned so much from it. 

On the other hand, switching gears after being deeply embedded in a male world wasn't easy. The process took me many years before I could come up to speed in a new world which was and is constantly changing for women, transgender or not. In fact, it could be argued, catching up is more difficult for a trans woman because we have to start from scratch and often be better in the world than other women just to survive. Having the confidence to own who you are is the only way to do it. 

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.