Was there Ever a Plan

Image from the JJ Hart
Archives

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

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

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

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

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

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

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

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

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

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

Trans Woman in the Sisterhood

 

JJ Hart on left out with Friends.

I write often concerning my gender transition into transgender womanhood. 

Sometimes I wonder if I emphasize the complexity of doing it. Securing a place for me in an unwanted male world seemed to be so simple. Men have just a few power bases to interact with as they proceed through life. Such as money, or athletic prowess. Plus many males never have the chance to grow into manhood at all and never mature into quality human beings. 

Women face the same hurdles. Many females never make it  to womanhood. Which is a socialization process. Transgender women face additional obstacles during their journeys to be accepted into the sisterhood. As my second wife always told me, I did not really know the gender processes cis-women go through and she was right. I had not earned my right to be there...yet. It was not until I made it out of the mirror and into the world did I begin to learn what she meant. In many ways, she forced me to learn it on my own without her help. She was much wiser than I was but I was stubborn and determined to learn on my own about what being truly accepted into the world of women meant.

First of all, I needed to discover women operate in a parallel universe than men and somehow I needed to slide behind the feminine curtain and learn from other women how their world was run. I discovered that just like men, there were the alpha women who once they accepted you, you were in. With women, the difference was they were much more layered than men. Take appearance as an example. While I started out obsessing on how I looked, other women around me were noticing how I acted. I needed to walk a thin line with my communication efforts with women. On one hand, I was the quiet observer of what was going on but on the other hand, if I was too quiet I was coming off as too aloof or worse yet, bitchy. In the end, I was able to walk the communication tightrope and survive in a new exciting world as a transgender woman.

The biggest surprise I continued to have was how layered the whole experience was and is. Take conversations about children as an example. Women who have birthed kids share a special bond with other women who have done the same. I needed to interject my daughter and grandchildren experience on occasion without going too far. I felt the entire process femininized me and kept me behind the gender curtain. Being apart of the group was good. 

After awhile, being in the sisterhood had it's rewards. I mostly socialized with two or three cis women all the time which kept any potential problems from materializing. I was able to be protected from being a single woman out by herself and learn about the life I wanted to live in the meantime. One evening at a time, I was earning my way into my own level of transgender womanhood. Many times the process was scary. Such as the evening I went to a pro-football game with friends but the offer was too good to turn down no matter how frightening the situation was. Since it happened when I was first climbing away from my dark closet into the world. 

In so many ways, I owe several women friends whom I always say helped me more than they will ever know. They ushered me into being a trans woman in the sisterhood. 

Ironically, it was only the beginning as I needed to keep building on the feminine experiences I was having. A prime example was when I moved in with my wife Liz in Cincinnati. When I did, we started to attend small meetup groups with total strangers which added to the layer of meeting and being accepted by other people. The entire process for the most part was very positive and a great way to immerse myself even farther into the sisterhood. 

Engineering the Envioronment

 

Image 
JJ Hart.

As I transitioned into an increasingly feminine world, I faced many difficult issues.

I was keeping very busy with all the new sights and sounds I was facing. It was all so exciting while at the time, all so scary. Here I was trying to survive in a new gender world I so desperately wanted. Basically, with no training as I was only a very serious observer of the world of women and was never allowed behind the invisible gender curtain. 

I found out quite early I needed to engineer my own environment. Mostly, as I said, I was flying blind and needed all the help I could find. I was immersed in losing all my old male privilege's. I survived losing a good portion of my intelligence and learned how to be mansplained on many levels along with changing how I viewed my own personal security. Instead of thinking I was safe in unlighted dark spaces, I began to look for safer well lighted areas. All lessons cis-women learn at a young age. 

Once I learned I could basically dress to present properly with other women where I was going, I began to engineer more places to go to test my future into transgender womanhood.  Sometimes I was successful and other times I wasn't, mainly because I chose the wrong venue to go to. For example, bookstores were more gender friendly to me than redneck bar venues where single women rarely ventured anyhow. It took several hard earned lessons such as having the police called on me before I learned my lesson and stayed in more friendly environments . Again, experiencing what cis-women already knew. 

Ironically my journey took me to the spot some call the impostor syndrome. It occurred at all times and without notice. Such as during girl's nights out and other times when I was succeeding in living in an exciting new world. It was frustrating when the feeling slipped in which was telling me I should not be there at all. Ruining the good time I was having. 

The whole process forced me into pursuing and engineering whole new levels of my gender existence. Once I thought I had controlled everything I needed to learn to live my life as a transgender woman, something else arose to prove me wrong. Communication as a trans woman with the rest of the world who were primarily other curious women became a strong focus of mine. If I could communicate properly with other women, I had a leg to stand on to survive in my dream life, without it, I had nothing' and the time and effort I had previously put in would go for nothing. 

I was never an engineer in anything else I tried in life so all of this was new and different for me. I was also a bit of a quitter when it came to finishing a project. Completing my journey into transgender womanhood was easily the most difficult and extensive project I had ever contemplated finishing. All along the process just felt so exciting and natural, I had the best and worst times of my life as I kept on going until I reached my dream goal.

Finally, I learned the environment I was in could be trans friendly for me.  Hopefully, in the new world we are facing in the future, we can maintain it.

Outreach the Easy Way

 

Out with my wife Liz
on left.

Last night, I took Liz and her son out to a steak house for her belated birthday dinner. She is a big fan of a good steak. 

To show you how popular the place is, we needed to wait for an hour for a table. There were not even any seats in the waiting area, so we had to wait outside on a solid metal seat. Fortunately,  the weather was unseasonably warm and dry so all we had to do was watch the other customers come and go. By doing so, I was able to notice the amount of fancy pickup trucks in the parking lot. A fancy pickup truck in my mind will forever tell me the driver is a fan of the new president I dearly dislike so I wondered if I would face any negative feedback from being transgender in the restaurant.

Once we finally made it into the venue, the pressure was on to see what everyone else thought of me. My fears proved to be unfounded. Even though the other people in the lobby had nothing else to do but to people watch, nobody zeroed in on me. I was essentially invisible to the world which is what I wanted. Men, women and children ignored me as they fidgeted, all waiting for a seat.

To be sure, it was not always this easy for me. I went through years learning the art of makeup and fashion I needed to transition out of a male world and into a feminine one. I was stared at the least and laughed at the worst when I went out to eat. All along I was a woman on the inside just waiting to get out. I was in my own version of gender heaven and hell. It all paid off when I have experiences such as last night but sadly I still have scars from unpleasant past experiences. 

By this time, you may be thinking I am a person with a huge trans ego problem. My second wife was fond of  telling me my femininized life was not all about me. She in most senses was not wrong, I was going all out to be the best cross dresser or novice transgender woman I could be and I needed to watch the room and other people around me to judge how I was doing. There simply was no room for anything else in my life on most days. 

It took me years to learn to relax and enjoy my new transgender womanhood as I was too busy still trying to read the people around me. Last night was one of those rare evenings I could relax mainly because I felt I looked nice, sounded confident and even felt physically better which all contributed to a fun evening. A good night of transgender outreach to all those pickup drivers who saw us portrayed as monsters during the previous election. As I look to the future while I process my past. 

What did I wear? My The Ohio State University sweatshirt, jeans and tennis shoes to blend in with all the other Ohio State fans in the venue wearing their fan gear. However, I did step up my hair and makeup with eye makeup, foundation and lipstick. So I wasn't a total plain jane. 

Whatever it took, I needed to blend in with the masses at the steakhouse and I did, they were not interested in me which was good. Outreach invisibility at it's finest.

What I Really Learned at Halloween

Kenny Eliason image from UnSplash.

 Sadly, since I have lived over ten years as a full-time transgender woman, Halloween has become just another day to pass out candy to any kids who may come by the house. The neighborhood is becoming older and we don't have the influx of kids we used to have years ago.

Regardless, I still have fond memories of when I went all out for Halloween. I used the experience as a testing ground to see if I could actually go out into the world as a woman and live. Throughout the month, I have focused on several Halloween adventures I had. When I first started, I thought dressing sexy would validate myself as a woman. Then I started to tone down my "costumes" all the way to going to the last party I remember dressed in feminine business casual attire which I was used to presenting in the upscale malls I was going to. 

The party itself was sort of a who's who of invitees held at a real live Victorian mansion in a restoration district in the town I lived in. I received my invitation because I was a fairly well known radio disc jockey in town at the time and happened to know the couple putting on the party. I knew immediately what I wanted to wear and just needed to decide who I wanted to invite to come with me. I knew my first wife was not into Halloween and wouldn't care if I invited someone else to go with me, so I invited the news-woman where I worked to go instead. An example of how easy going my wife really was. I always thought if I told her I was leaving for a month for gender realignment surgery, it would be fine with her. So the stage was set to be out and about as my authentic self. No playing around with a "costume", I wanted to be mistaken for the real deal.

Since there are no pictures from the party, my outfit consisted of a business suit, heels and blond shoulder length wig. Needless to say, my wife was not surprised but my date was completely. Mainly because of my shaved legs and how well I walked in the heels. When we arrived, thankfully, parking spots were not a problem and at the door, a coffin with a real skeleton greeted us . The mansion was really decorated well and we found a seat. 

Predictably, as the night went by, no one knew who I was and I blended in as a woman who arrived late from work and did not have a chance to find a costume. I was having a great time, when another couple came up and said how impressed they were with the way I looked and they thought I was a woman. Furthermore they were leaving soon to go to another party and wanted to know if we or I wanted to go along. Even though I was extremely flattered I turned them down but not before I found out who they were. The couple was a young congressman and his wife, leaving very soon to go back to Washington, DC. So I guess I destroyed any chance I had at a political career. 

What I really learned that Halloween was I could step out into the world as my authentic feminine self and survive. Very much worth all the time and effort I had put into to being a girl over the years. And, as far as the news-woman went, she never said a word.  

I guess you can say with out a doubt although the thrill is gone for my Halloween, the day more than any other one in my life served a wonderful need when I did not have any other outlet.

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.  

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

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

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

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

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

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

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

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

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

It is Fall and Time for Halloween

 

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

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

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

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

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

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

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Intimidating Women

Library of Congress 
image from 
UnSplash.

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

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

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

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

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

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

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

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

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

 

When Every Night is Girls Night

Grae Phillips is still active
on Facebook if you want to 
see more. Or just keep up. 

I know I make a big deal out of my second huge transition, when I mentally moved from being a serious part-time cross dresser into being a novice transgender woman.

Sometimes I feel as if I am putting myself on some sort of a gender pedestal when I write about not considering myself a cross dresser anymore. If it comes off that way, I don't mean it to. On occasion, the written word gets in my way. Getting back to the cross dresser versus transgender statement I made, I think in my case, it was a matter of me judging my own life. Originally, as I was working my way through my early years of admiring my girl self in the mirror, I knew it could never be enough. There had to be more. I was so tired of cross dressing for one day and then two or three days later wanting to do it again. 

As I always mention, all of this occurred back in the pre-internet information era when any news and contact with like minded gender individuals, be they transvestites or transsexuals, was very difficult and rare to come by. This was even before the barrage of talk shows led by the late Phil Donohue who interviewed female impersonators such as "Grae Phillips", all the way to transvestites seeking approval from a doubting world. It was quite a bit for me to sort out. But I did. I knew I could never be as beautiful and talented as Grae but I could reach the standards of most of the transvestites I saw on my television. There was hope for my future after all.

As I progressed into meeting more and more diverse cross dressers or the women known as the new transgender group I began to think what it would mean if I went all the way and every night became girls night. In other words, a time when I would never have to go back to my old male self and live. Deep down I knew there would have to be some sort of line drawn in the sand if I did. As much as I loved all the fun of the newness of applying makeup and picking out clothes, I wondered what would happen when the newness wore off and I needed to settle into the daily routine of the transgender womanhood.

It turned out, I had nothing to worry about. I settled into my new feminine routine as if I had always should have been living this way. I found I didn't have to do much special on many days such as most cis-women do and then again still have the fun of dressing up for special occasions. It was true, once I jumped the gender border from cross dresser to transgender, I could experience what life could be like if every night was girls night.  

The Prom Gown

Image from Joeyy Lee
on UnSplash

Years ago, I received a prophetic statement from an unknowing doctor when our family was on vacation in Canada. 

When we were not out fishing with Dad, we played football on a hard-packed lot behind the fishing camp with a bunch of local kids. Being the budding football star I never was, I decided to try to play running back and was actually successful bulling my way through the opposing boys on the other team, for awhile. On a play I would learn to regret, I was picked up and thrown down on my shoulder and suffered a broken collar bone.

I say regret primarily because my Dad was not amused about having to interrupt his vacation to take me to a hospital for treatment. At the hospital, I had X-rays taken and was diagnosed with a broken collar bone. I was seen by a doctor and had my shoulder bandaged up in a sling and was told it would heal on it's own. Leaving only a tell tale bump which showed it had ever happened. Then the doctor said, since I would not be wearing any prom gowns in my future, it would not matter anyway.

I thought at the time, wait a minute! What if I wanted to wear one of the beautiful gowns I had seen on women in my future. What then. I think that comment hurt worse than the actual breaking of the bone. Plus, when I did go to proms and was stuck in an ugly tuxedo, I always looked at the girls around me for any tell-tale bumps to show a collar bone break. I never did see any. 

Along the way, I had several other instances of my feminine aura shining through. I have/had a nephew who from an early age developed a very unsavory attitude towards life which sometimes carried over to me. It started with my politics clashing with his right wing bigotry and going from there. On several occasions, he secretly complimented me by saying I threw a football like a girl. He even said one time when I bought my new Porsche Boxster, I had bought a girls car. Like I said, he was trying to hurt me but was secretly making me feel good. I could not wait to be the attractive blond woman in a sharp sports car.

There were other times when I was called feminine when I was doing my best to be a macho man. Several times at work, I was called "Ma'am" out of the clear blue sky in the middle of a normal conversation with a customer. Looking back, I think it was my feminine aura slipping through my male fence. 

Even though it took me years to realize my dream of living as a transgender woman was much more than living as a part-time cross dresser, I realized there were several tell-tale signs along the way. Maybe the doctor was trying to tell me someday I would want to actually wear a beautiful prom dress which showed off my collar bone break bump. Or my evil nephew would go on to having his own insecurities to deal with. I have not seen him for over a decade, so I don't know or care. He would probably just say he was right about calling me a girl. 

It turned out there were many people who saw through my disguise and at the least knew I wasn't who I was desperately trying to be. A stable, non toxic, productive man. I failed miserably and all I ever wanted was to be the one wearing the beautiful prom gown.   

Calling me a woman was the ultimate compliment. 

A Cajun Night Out

Ohio River Pride Image
of Author JJ Hart

Recently I passed my seventy fifth birthday. To have a mini celebration, my wife Liz took me to one of our favorite restaurants which happens to be a Cajun food place called the "Swamp Water Grille." 

Even though we live miles and miles away from Cajun country, the chef/owner of the venue studied down in New Orleans and his food is incredible. Before I could get to the food, I had to go through the usual steps most women go through to get themselves ready. Since we just finished watching the Ohio State - Iowa college football game and the venue is quite casual, Liz and I decided to wear our Ohio State University sweatshirts. In addition, I added a close shave, foundation, contouring and lipstick and was ready to go after I brushed and tied back my hair. 

As I prepared, I realized I was putting the effort in to be invisible in the venue but I wasn't. For some unknown reason, I went first to the hostess stand to put our name in on the wait sheet. The first thing which happened was the hostess gave me a big smile and complimented me on my glasses so I was not so invisible after all. She was obviously of the younger generation which does not have a problem with transgender women or men so I felt warmly welcomed to the venue. Not to mention feeling a little relieved of my anxiety I was experiencing. I was further confused because I had been at the venue before with no problems what so ever. It is just a sample of the anxiety I live with. 

From there, it was clear sailing and no one seemed to notice me at all. They were all so busy with enjoying their food, friends and surroundings they did not have time for me. The only person who we were dealing with was our server who addressed us as "ladies." Which is wonderful of course. I went through so many years of disavowing my true authentic self, I don't think I will ever tire of being referred to in the feminine tense. 

As we finished our wonderful dinner and drinks, it was time to bring the evening to an end and we headed to the car. Ironically, I felt the benefits of being largely invisible to the world as an older transgender woman while at the same time being very visible to myself. It seemed everyone of my senses were heightened as I waited for someone to stare at me and say something negative. I guess no matter how successful I am in my relatively new life, I will always experience the stress and tension of be confronted in my life.

In the meantime, a little (or lot) of great Cajun cooking helped me to experience a huge dose of gender euphoria. The best gift I could have ever experienced.
    

What If?

 

Marci Bowers

As I spent all the years as a very serious cross dresser, I dreamed of perhaps becoming a transgender woman and what it would be like to live a feminine life.

For many, many years I was my own worst enemy as I learned the parameters of what I needed to work with. First of all, I needed to play catch up with all the girls around me who were already experimenting with makeup and fashion. I remember vividly back in the mini-skirt days how the girls in my class would not so shyly sit and cross their legs to tease all the boys. Little did they know, the affect they had on several boys such as me. I wanted to be them and wear the skirt and panty hose and tease the boys.  I was so envious of the stories my wife told me of how she would roll up her skirt when she went to school and was out of sight of her Mom. 

I always wondered what if I could ever escape the mirror and experience life the same way she did. Of course I did not and had to set my own course. A course with no guidance or peer pressure on how I looked. What if I could live as a woman remained an illusive dream. To keep my frail mental health balanced, I tried to improve my presentation on my own  As I am fond of saying, I experienced quite a bit more error than trial as I slowly learned to express and embrace myself as a novice transgender woman. To add to my excitement, my wife and I purchased our first computer and I was able to learn about other transgender women in the world. 

One of trans women I learned about and was suggested to me by a reader (thank you) was renowned sex change surgeon Marci Bowers. Even though I knew I would never consider gender surgery for myself. Just reading Bowers journey gave me hope for my future.  My fondest desire her story would pave the way for an easier gender transition for the rest of us. 

I followed my new found confidence by exploring more and more as I tried  to carve out a niche to build my dream life. Even though I was rejected on many occasions, I still managed to climb the steep slope towards my transgender dream which was coming into focus. The main discovery I made was if I was myself, I could actually have the opportunity to live on into trans womanhood. If I did, I knew the risks were great and I was jeopardizing years of male life I had sacrificed to build up. 

Still I learned I had to follow my inner soul and see what if meant to me. Since I had worked so hard to climb dual gender mountains in my life, it was time to jump and head for a hopeful safe landing.  Even though I could never hope to be as accomplished and attractive as an Marci Bowers, I discovered just enough people valued me as my authentic self, I could survive. These were the people who never knew my before person and I was starting all over with. 

Even though I was still doing the pushing, they were the ones doing the pulling me into my new world. Proving what if was possible. 

The Sixty Four Crayon Box

Image from Leisy Vidal on UnSplash

I view gender in light of all the recent attacks  on the transgender community from a certain political party here in Ohio not called the Democrats, as a big box of crayons. The whole shameful process just shows how little the Republicans care to know about the trans community,

Rather, if they like it or not, almost all humans fall on some sort of a gender spectrum. It seems, men have fewer crayons to pick from because of their innate insecurities concerning their own gender and or sexuality. Which is a whole separate subject.

I know when I began to color in my own life, I needed the big box of crayons because I did not fit the male mold I was in. Whatever the world thought of me, I needed more out of my life than a restricted male existence. Instead of viewing myself as the round peg being forced into the square hole, I started to see myself as a multi-colored individual with many new gender frontiers to explore. My journey was destined to take me far past the rather quick romance with all the pretty fashion, all the way into a in-depth dive into what a life as a transgender woman would be all about. As I was busy coloring my future, I found I needed different colors to enable me to express myself more completely.

Examples were plentiful. Such as when I looked the part of a woman, how was I ever going to communicate as one. I was so busy coloring, I needed a whole new box of crayons to keep up with my life I was attempting to balance between two genders. To further stereotype the whole process, I quit using all the drab and darker colors and began to use the lighter more vibrant ones as I lived more and more in a femininized world.

The more I went to diverse transgender mixers in nearby Columbus, Ohio, the more I learned about others who were coloring in their gender lives too. I was able observe everyone from those who had almost completed their new lives, all the way to those who were working with broken crayons and severely struggling. All of it was an extreme eye opener for me because I was so naïve when it came to the transgender or LGBTQ world as a whole. Normally what happened was, I took everything in and ended up going back home and thinking about it. A solitary pursuit since I did not have anyone to talk to about it except for the occasional therapist. 

Therapy produced mixed results when several I went to did not want to discuss or see my colored design of who I truly was. It wasn't until I sought out one of the rare gender therapists back then who told me the truth. Basically, she said my picture was beautiful and there was nothing I could do about wanting to proceed on my path to transgender womanhood. I wish I would have listened and started to change my life back then but I was stubborn and hung on to my part-time male existence which at the least, paid the bills. 

As transgender women and men, we really need the extra courage to keep coloring our pictures. For example, in my case, if my health holds up, I will be on gender affirming hormones the rest of my life. Hopefully, I will need another sixty four box of crayons as my life expands as a transgender woman.

 

Man, I Feel Like a Woman

Shania Twain

 Maybe you saw country star "Shania Twain" as she hosted the 2024 People's Choice Country Awards. 

If you did, you probably remember when she sang the iconic song "Man I feel Like a Woman.". The song meant quite a bit to me for a number of reasons. The main one of course was I did feel like a woman, not to mention I would have given anything to have her appearance. 

The song was popular during the time I started to find and patronize two small lesbian bars near where I lived. One was a very rigid lesbian biker bar and the other was a much more mellow atmosphere where I happened to know one of the bartenders as my male self. Even though I was begrudgingly served in the biker bar, I always sought to poke the bear. I discovered the easiest way to do it was to play Twain's song on the juke box. For some reason, the owner and other patrons resented me even playing it. I found it to be great fun until I came in one night and the music machine was completely turned off. From that point forward, I took the pressure off  and just started to go to the other small lesbian bar where I was welcome.

In the other bar, I was able to learn many of the nuances of the lesbian community and figure out where I fit in, if at all. In my jeans, boots and makeup I discovered I was closer to being a femme or lipstick lesbian and found I drew the attention of the very serious bull or butch lesbians. I even was heavily induced into singing karaoke by a huge woman in a cowboy hat. Since I am a terrible singer, I tried to let her take the lead and I quickly left the bar shortly after singing. The only thing I heard her say was my voice was lower than hers. I never saw her again.

On the other hand, a super butch who was on his way to becoming a full fledged transgender man just happened to be my first dinner date with a guy. He later told me how scared I was,  he was right. 

Through it all, I still did feel like a woman and did appreciate the acceptance I gained from the lesbian community. I never had to try to adjust my sexuality and was validated as my new emerging self without needing a man and all the potential problems which came with it. On the other hand, there were a few men I did feel a connection with just enough to wonder how the other half lived. At the least I knew I would not have to operate on the gender fringes forever if I had to. 

Needless to say, I will never achieve the appearance standards of a Shania Twain but most other women (trans or not) will not either. Plus my womanhood was achieved in a different way than most cis-women. None of it was my fault and I did the best I could with what I had to work with. And, in the end result, I do feel like a woman.  

  

The Ultimate Challenge

Vacation image from Kansas
by JJ Hart

I am biased but I think changing how you live to reflect your authentic gender self is one of the toughest things a human can do. 

Perhaps you noticed I said reflect your gender tastes not change them. I believe our transgender selves are already determined and we are attempting to sync them up to our extremal selves the world can see. The path varies for most of us but the final goal is always the same. Sadly we have many obstacles in our way. 

One of the main ones is trying to overcome the effects of testosterone poisoning which gives us the hated male characteristics we did not ask for. I remember hating all the changes which were happening to my body and how the changes would effect me when I attempted to cross dress in front of the mirror. All I knew was my life was changing for the worst and I did not want it. Much later on when I became much more serious about my femininized presentation in public, my goal was to hide my broad shoulders and the angles of my body with new fashion. 

It turned out, testosterone poisoning and new fashion were the least of my problems as I continued along my path to the ultimate challenge of living as a full time transgender woman. There were so many times I never thought I was going to make it. I had so much baggage to sort through as a man as I had acquired over the years. Since I had spent so long doing my best to build my life, then I needed to decide what to do about my family, job and friends. Leaving me between the gender rock and a hard place. Often I did not know how I was going to find my way out of my predicament. Was I still a man, or a woman and what about my long standing sexuality.

Obviously, the ultimate challenge was to sort through all my issues while I was still attempting to live my so called normal life as a man. I ended up trying to live a little at a time as a trans woman until it began to feel so natural I never wanted to go back. Slowly but surely I was proving to myself I had been born feminine and just forced into the wrong gender by some sort of a cruel twist of fate.

It was around that time, I found I was not alone and began to discover other challenges on my path to transgender success. I learned from others around me about their own successes and failures or triumphs and purges. Often my own feminine wardrobe would be gifted by an acquaintance's giant purge. In fact, my first set of expensive silicon breast forms were gifted to me. The breast forms were a real step forward from what I had ever had before and would help me to present better so I would not be discovered as a man.

As Paula wrote in and commented: "I don't know if we ever get over that fear of being found out, of being exposed and ridiculed. I think this is much more about how we see ourselves than how others see us, I look in the mirror and see all my history, the Dan Dare chin and the prop forward shoulders, others just see a late middle aged woman who happens to be on the tall side."

Thanks for the comment and as I am fond of saying, these days I present as old. Since the genders have a tendency to merge together later in life. I am also happy to have made it to the place I have in my life but as I near my seventy fifth birthday, I know the ultimate challenge is yet to come.  

Complacency

 

Summer Image with padding.
JJ Hart

As I did my best to transition from male to female there were many times I experienced moments of complacency.

It happened slowly enough as I kept throwing lifelines to myself so I could survive a life burdened with gender dysphoria. To add insult to injury, I was not gifted with feminine external attributes to help me along as I initially tried to make it in the world as my authentic inner self. Disguising my testosterone poisoned body was a total learning experience. Angles needed to be changed into curves using everything from pads to balloons to foam. Anything it took to perfect my image and avoid complacency. 

The main problem I had was I could not avoid all the years I had lived as a man. The male trip was never easy for me to learn and even a more difficult time to forget. I had survived and even flourished and now I was trying to give it all up and for what. To live as a woman which became an all encompassing goal. I would practice the best I could walking and moving as a feminine person. Even to the point of being called "Ma'am" when I was at work as a man. I figured it was because I projecting a feminine "aura" to the world and resolved to add the idea to my accessories when I was out in the world as a novice cross dresser or transgender woman. 

I started to project very strongly that I was a woman to any stranger I was interacting with. Along with looking them in the eye, I was able to be accepted for the first time as the person I wanted to be but I still had to guard in not letting up my guard and not slipping back into any of my old male ways. Just one time walking like a linebacker or not paying any attention to my new feminine communication skills could essentially ruin my whole day. It did not matter how much time, effort or money I put into my appearance, if I forgot who I was, nothing mattered. For years, my entire existence was still so fragile until I put in the years and work to tip my gender balance.

I can't say, even today I don't experience moments of complacency. It is easy when the cis-women my age and younger are for the most part very casual in their appearance. Ironically, when I see a woman in heels and hose in the grocery store dressed to the nines, my "trans-dar" goes up and I want to take a closer look. Perhaps the person could be part of the transgender or cross dresser sisterhood. 

Through it all, complacency or not I have never forgotten how the differences in female fashion is and was one of the fun parts of transitioning. No longer was I confined by the drab and boring male fashions. I had forever admired how the woman around me had the freedom to express themselves through fashion and now I could also.

On another topic, I attended two other LBGTQ support group virtual meetings recently. The groups moderator is a trans man and does a good job of keeping everyone involved. The group is very diverse and I was surprised to see a couple of the transgender participants seemingly have partially de-transitioned over the years. Plus I learned the Veterans Administration has finally approved electrologist visits under their care and my mammogram was approved after four tries. The main problem was the hospital I wanted it done at still had an old chart on me with my dead name so getting a new one was the problem. The VA needed to approve the process and did so my dead name information has been changed on yet another document. Progress is progress I guess.

At least I was not being complacent and stayed the course until I saw results.

Feeling the Pain

 

Image from Eugenia 
Maximova 
on UnSplash.

Learning on the fly all I needed to know concerning my authentic life as a transgender woman often resulted in pain.

The pain, early on mainly materialized when I rushed the process of going out in public as a novice transgender woman or cross dresser. Many times I was reduced to tears following being stared at or even laughed at when I was simply out walking around. I felt the pain for years until I finally realized I was the problem and sought out the reasons why. The main reason was (as I always mention) my male ego was dictating my femininized fashion sense. He was thinking attempting to dress sexy would somehow validate myself as a woman. Of course, it didn't and just made me look ridiculous. On the other hand, when I dressed to blend in with other women, they validated me as a woman.

My frustration and pain increased until I became fed up with the entire process and changed it. My thrift shopping adventures began to change to reflect my new fashion sense. I was held back in many ways by my budget and knowledge of what fashion I was trying to buy. Sizing was an example, as I struggled to find what looked best on my testosterone poisoned body. I did not have the benefit of having any feminine characteristics to begin my journey so trial and lots of error is what I went through. Every time I learned a fashion choice I made  just would not work, I felt the pain return again.

My situation improved when my overall confidence improved to a point where I was able to use the women's changing rooms. When I could afford to go to a mall clothing store, I always checked with a clerk first to see if I was to be accepted so as not to feel the sting and embarrassment later. In the thrift stores I went to, the changing  rooms were not monitored anyhow, so I never had to ask. As I said, when I had the opportunity to try on clothes ahead of time, my improvement rate went way up and my fashion pain way down.

After conquering most of my fashion pain, next up came my paranoia over communicating as a transgender woman in the world. Of course I quickly discovered I had no idea of how women communicate between themselves. I found myself on several different levels when I dealt with the world. Once I figured out I was not "fooling" anyone else and just resorted to being myself, my life improved. One level of woman just did not care and basically ignored me while another level was curious and wondered what I was doing in their world. Overall, I was learning on the fly and had my share of pain such as the one transphobic woman I encountered at a party Liz and I attended many years ago. She was actively harassing me about what my dead name was. She was so evil, the experience still causes me pain to this day.

Overall though, when I compare my transgender journey to others I read about, I suppose I have had it lucky. Even though I had suffered a lifetime's worth of pain when I lost my wife, several close friends and my business in a span of five years, I was able to find new friends and rebound. Mainly because the friends and Liz accepted me as my authentic feminine self. I guess karma was paying me back for a lifetime of wondering what I was doing about my transgender self. All the years of doubting my gender existence came back to be a strength when I quit being a victim in my own life. 

Sure I was transgender but suddenly it became a strength not a weakness and the pain was behind me. 

     

A Spectator in my Own Life

 

Image from Author JJ Hart

There were many times in my life when I felt as if I was a spectator in my own life.

From the first glimpse in a mirror when I cross dressed as a girl, all the way to when I first went out determined to be a woman rather than just look like one, often I was on the outside looking in. Being on the outside was certainly not a great place to be. I literally spent decades of my life worrying about where I actually stood with my gender issues.

Along the way, I grew tired of being the spectator and wanted more inside information on how the feminine system I so admired worked. I discovered the hard way, I was not going to be allowed to learn more until I made the drastic step of increasing my transitioning efforts. Naturally, it was very difficult to do when I was totally immersed in leading a male life which I had become quite successful at doing. Overall, I was becoming the victim when it came to my life as a whole. I kept wondering why me when it came to my desire to live as a transgender woman. I finally had to shake it off and move forward with my gender transition before I lost everything I knew in life. 

It turns out the real culprit was myself.  I was afraid to face my truth and it cost me. I even tried to out run my desire to live as a woman by moving and switching jobs. Once I talked my wife into moving from our native Ohio to the New York City metro area. Then back again a couple years later. Living in different parts of the country was certainly an eye opening experience but did very little to help my gender issues. On the rare occasions it did like the night on Long Island when I went to a transvestite mixer and the hosts thought I was a cis-woman was flattering but did me no good the next morning when I crashed back into my male life. Then my poor wife had to put up with my mood swings.

Still I was a spectator in my own life when I walked down the long hallway in heels to get carded for my true gender to the times I did the family grocery shopping in sweaters, mini skirts and flats, I wondered who was that? It took me years to come to the conclusion the other feminine person was me and she had a right to be here in my life. Slowly but surely, I was building the life experiences needed to cross the gender border but it kept taking me so much time. I kept running into so many road blocks, I thought I was some sort of a gender construction engineer. 

Regardless as time flew by, it was time to put my gender cards on the table to finally determine which gender was going to be the primary provider in my life. What I attempted to do was live as much as I could as a novice transgender woman to see if the lifestyle was for me. Even though initially I did not attempt to do it, the trans life rapidly snuck up on me. Before I knew it and maybe before I was ready, I began to carve out a brand new life as a woman. Quickly I needed to develop feminine communication skills which was difficult for me to do since I was overwhelmingly dealing with other women in my life.

Through it all, slowly I grabbed total control of my life and became a spectator any time I was forced back into my old unwanted male life. In other words, I finally faced my own truth and flipped the ultimate gender script in my life.