Then I Went and Did It!

 

Trans Girl image from
Alexander Grey on 
UnSplash.

I played around for nearly a half a century being a very serious cross dresser. Sounds like a long time, doesn't it!

It was while I was doing it but now it seems like it was a blur. Most of it started with all the problems of sneaking around my home when I was growing up. I needed to use a ton of creativity to hide my cross dressing itself and not to mention the clothes I had accumulated. Somehow, I managed to do it all. Who knows, maybe it all made me a better person? I doubt it but at the least, the process helped me to be more creative with my life.

As I progressed slowly with my makeup art and improving my women's fashion choices by going to thrift stores, I found out I could do more. Then I went and did it by going out and testing the public's reaction to me as a novice transgender woman or at the least a skilled cross dresser. I found, the more I did it, the more successful I was and I felt so natural. To me, feeling natural was the best way I knew I was on the correct gender path and I wanted to keep going. Plus, feeling natural, gave me the confidence I needed to always push my gender envelope and try to do more and more. I even changed the way I viewed my Halloween costumes I was choosing. I started to go away from my trashy woman's look and then tried for a more realistic approach. I searched my brain for ideas which allowed me to try to present as a cis-woman at a Halloween party. Again, I went and did it when I succeeded at two parties where I was actually mistaken for a woman. Which in fact I was just learning I was.

By this time, it was too late to turn back and ignore my gender dreams. I was having so much success building a new life as a transgender woman, I just couldn't turn back. Even my sexuality was not a problem when I began to attract more attention from cis-women than I ever had as a man. I was validating myself as my own type of woman through my years of femininization and it felt so right. Then, I went and did it and jumped into the girl's sandbox and after a few bruises was successful. The claw marks I received on my back I felt were all learning experiences and I stayed and eventually held my own. 

All of this led me to my next transgender step of researching the possibility of beginning gender affirming hormones. Then I went and finally did by making my first appointment with a doctor who I heard would prescribe the hormones if a person was healthy. Thank the Goddess I was and the fun started. Like so many others, I needed to begin my hormonal journey on minimal dose of medication until my doctor and I could see how my body reacted. As it turned out, my body took to the new feminization hormones the way I hoped it would. It was like a big I told you so as my body changed. Inside and out. I needed all the help I could get in the appearance department and I was overjoyed when my facial angles softened and my hair quickly grew to a point where wigs became a part of my past. Luckily, my family history had no male pattern baldness for me to deal with. 

Since my overall appearance was becoming highly androgynous, I was loving it, I decided to give up on what was left of my old male life. I was to the point where none of my male shirts fit my breasts anymore, so rather than buy new bigger ones, I decided to go and do it. Give away what was left of my male clothes and live fulltime as a woman, transgender or not I was ready for the world. 

Since I had taken my time to make certain my gender decision was the correct one, I had no problems of never looking back. Many times now, I wish I had the courage to do it sooner and not have to worry about so many then I went and did its. 

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. 

Trans Girl at Pride Day

 

Pride Flag image from
Jason Leung on UnSplash

Welcome to Pride Month. The only month of the year when the LGBTQ community is celebrated by a portion of the world and hated by others. Sadly, the month brings out all the gender bigots in the world. 

Early on, I had many experiences at various Pride Days with my new circle of lesbian friends. Including non lesbian friends when a meetup group my wife Liz and I were in operated a table at Cincinnati Pride for a couple of years. On occasion, I even felt as if I was the token LGBT person in the group. Regardless, I had a good time people watching all the diverse public which was walking by. I saw everything from lesbians wearing nearly nothing to cross dressers teetering painfully around in their heels and hose. Then, of course there were the drag queens who I almost felt were embarrassing to me because I did not want anyone to think I was part of their culture, I was transgender not a drag queen. My disclaimer is I have nothing against drag queens but my days in male gay bars taught me how unfortunate it was to be mistaken for a queen. 

Plus, I wanted everyone to know how important it was to me to be recognized for being a transgender woman in a sea of other diverse people. Along the way, I felt the Prides I went to started to emphasize trans people and not the drag queens who seemed to get all the attention with their flamboyant attitudes and clothing. Cincinnati in particular a couple of years ago featured a trans woman I don't remember now as their parade marshal. Plus, I started to see many more transgender women and trans men in the crowd along with groups of butch lesbians and gay male "bears". It made for an interesting experience as my preference was to be mistaken for a lipstick lesbian. Or a lesbian who wears makeup. 

Early on, back in our drinking days, Cincinnati Pride always featured an after hours "Pub Crawl" which one year even featured a bus which took us to many gay venues we had never been to before. I had always wanted to live in Cincinnati and this was a great way to experience it, without ever driving because at the end of the evening, we took an Uber to get home. A great time was had by all. 

Of course, Cincinnati wasn't the only city in the region which hosted a huge Pride celebration. Before I moved to Cincy, I lived within a half hour of Columbus, Ohio. Columbus, as I said, had a LGBTQ celebration which rivaled all the others in the state. This time I went with my new circle of lesbian friends including Liz and two others. Similar to my Pride experiences in Cincinnati, the drag queens became less of an influence and better yet, I could relax and enjoy myself. That night for some reason, we ended up in several straight bars without any problems. 

These days, Pride has really expanded. In the local metro area alone, there are four separate celebrations going on this year. Sadly, with most, after the celebrating has died down, the same old problems exist for transgender women and men in the community. Big corporations who support Pride go back into their closets and I assume wait for the push back from the gender bigots. 

At any rate, it is refreshing to see the public media support for our community. Even if it is temporary.

Enjoy your Pride month no matter where you are in your gender transition! That includes all of you who identify as cross dressers. You never know when all of that may change. It happened to me.

Transgender Stairsteps

Image from Reinaldo Kevin
on UnSplash

As I progressed through life, the idea of me being transgender took up more and more space. 

When it did, I had to create my own steps to arrive at the next level and negotiate all the many stop signs which impeded my progress. For awhile, I was so engrossed in my own appearance, my second wife called me the "Pretty, pretty princess." Mainly because she did not use much makeup and was not very girly herself. I did get my revenge on the occasions we were going out and she had to ask for my assistance with her makeup. It was all I could do to not say something like did she all of a sudden need the "Princess's" help but I didn't.

Little did I know, presenting the best I could as a cross dresser or novice transgender woman was just the beginning. As I was attempting to learn as much as I could about the next step I was stonewalled by my wife who did not want me to go any farther as a trans woman. Not to mention my male self, who was doing his best to derail my gender journey the best he could. It was obvious, he wanted nothing to do with giving up any of his power over me. 

With or without either my wife or my male self, my path was set and I was intent on finding and climbing the next steps towards living as a fulltime transgender woman. Now I shouldn't get  too far ahead of myself because of all the steep stairsteps I still had to climb. The first step was to determine exactly what my gender identity was. Which included my all important sexuality. Since I was planning on living a feminine lifestyle, would I be expected on changing my sexuality as well. This time of my life was very exciting and scary at the same time. When I made it to my next step, I needed to maintain my balance before I could even think about going forward to another.

Once I maintained my balance and was able to look around in my new feminine world, I loved where I was and could not wait to go on. After all, I was showcasing my new skills at blending in with other women as well as experiencing more and more communicating with other women which I went into in yesterday's post. I can safely say my communication experience was one of the most difficult things I had ever done. The next step seemed to be an impossible distance away. Somehow I made it anyways and the next move was seeking out the availability of gender affirming hormones or HRT. I did get approved by a doctor to begin the hormones and the next step was a huge one. Mainly because I had some sort of an idea of the physical changes I would be going through but had no idea of the internal ones.

All of a sudden, I was a different person. I could cry when I never could before as well as undergoing other inner changes. The step of hormones turned out to be worth the wait and all the anticipation. In fact being afraid of heights and climbing too high was worth it also. Maybe it is the excuse I can use to rationalize to myself why it took me so long to realize my transgender life long dreams. 

Before I go, I would like to wish a Happy Birthday to my oldest Grandchild who is graduating from The Ohio State University in December. My Grandchild also happens to be trans and identifies as "They/Them" and I am so proud!

Trans Girl Passing Privilege

 

Witches Ball Image. Tom on
left.

Passing privilege has been one of my biggest gender paranoia's over the years. Many because I did not begin my journey with any feminine characteristics I could see. Testosterone poisoning had essentially ruined my life when it came to establishing passing privilege. 

As I began to add angles to my body along with unwanted body hair and muscle mass, I began to think ever presenting well as a cross dresser / transgender woman would be impossible. In order to make my gender dream possible, I needed to look around at the other women my age and try to blend my style with theirs. The whole process was difficult and I made many fashion mistakes along the way. Even though I did, I managed to survive in the world as a novice transvestite on my own and move forward. Mainly thanks to brief moments of gender euphoria which always propelled me forward. To do so, I learned how important for me it was to blend in with other women. All I knew was, I enjoyed it immensely when other women would take the time to talk and communicate with me as an equal.

Through it all, I learned that even if I was not the most beautiful woman in the room, many other cis-women were not either. Since women operate on a more layered existence than men, there were many other possibilities to be successful in the world other than just being attractive. In fact, being transgender gave me an extra quality to my existence which many women were drawn to. As I crossed the gender frontier into a new feminine world, ironically I found I had more interest from women than I ever did when I was a man. 

Probably, one of the more profound statements I was ever told was when my transgender friend Racquel told me I passed out of sheer willpower. Which I took to mean (again) I was not the best looking woman in the room but went out into the public's eye anyhow. Together, we went to many so called straight venues together and had a great time with very little public push back, Even if I was passing out of sheer willpower, I was doing it successfully. Which was all that mattered. 

It mattered even less, when I was able to expand my small circle of lesbian friends who put the icing on the cake so to speak when it came to passing privilege. We were able to attend several lesbian mixers in Dayton, Ohio at several different venues. Even though I was initially very scared to go, I was quickly put at ease when I found I could blend in with the group in the venue. Sometimes the venue would be gay and sometimes straight which added to the excitement. All I know is one night, I was asked to be a lesbian wing person for my friend who was too shy to approach another woman and ask for her name. I even was able to steal a few kisses on the side one night from another woman I met. Willpower passing was great. 

I don't have enough power to do it but I think "passing" should be changed to "blending". With blending, you have the choice to dress with the other women you are going to be around and you have the choice not to if you like. In my case, I always wanted to do the best I could to enter the world as a transgender woman and blend in with the other women who were going to be around me. On the other hand, I understand also it is a trans woman's privilege to go to the grocery store in her heels and hose to do her shopping. It is all part of the fun of entering the women's world. 

The biggest problem with trans girl passing privilege is the amount of stress and attention put into appearance by the media and the outside world. The competition to look better seems to get stronger with each generation with the internet and social media being the major culprits. When the stress goes up for ordinary women to look better, it follows the pressure to be even better is real for transgender women and their quest to blend in with the public. 

At least now, there are plenty of self help makeup videos to help the novice trans girl along plus several of the big makeup stores offer advice and products too. Many more places than transgender women such I had when I was first coming out. Maybe it all equals out. 

Transgender. Complex or Simple

Is the art of being transgender very complex or simple? It depends on where you are in your gender transition cycle.

Anyway you cut it, femininization is a difficult process and I assume the same is true for transgender men seeking to enter a male world. In my past, I have had conversations with a trans man friend of mine about the trials and tribulations of using the men's room. The process seemed different to me because I had always taken for granted using the men's room and ignoring everyone else in it. I experienced a much different world full of complexity when I started to use women's room. Just making sure I looked another woman in the eye was a challenge, not to mention everything else I needed to remember to survive. 

Of course the biggest complexity was fashion, hair and makeup. Since we transgender women don't have the luxury of growing up feminine, we have a ton of catching up to do. It is often more painful than fun but is something we just have to if we want to ever make it to the simplicity side of our lives. In addition, the complexity of living trans comes full circle when it comes to our emotions. Then emotions lead to our overall mental health, so it has a very deep relationship with our everyday lives. If we are fortunate, we settle into and come to an uneasy acceptance of being our authentic gender selves is the goal. 

None of the conquering of the transgender complexities came easy for me. I needed to work my way through dressing as a teenaged girl in my mind all the way to being able to present to blend in the world successfully. I needed a whole new attention to detail if I was ever going to achieve my lifetime dream of being a fulltime woman, trans or not. It took awhile but I slowly adjusted my life to a much simpler mode which included being feminine. Fashion and makeup became second nature to me as well as the difficult attempts of dealing with the public which meant mainly with other women. 

There were so many serious facets of my everyday such as being to deal with such as what my sexuality was going to be. After all, since I was living as a woman, would I be expected to have sex with men. Since I had never had sex with men, I had no idea of what to expect. Would I have any pleasure, or would I have been doing it just for my own validation. Thankfully, I did not ever have to explore the new frontiers of sex as I found I was still attracted to women and my lesbian women friends taught me it was fine to be so. So the sexuality of my life didn't change and stayed very simple.

Life is complex enough on it's own without adding in the complexities of being transgender, so we face the ups and downs of following our paths. We somehow find we are carrying pocket knives to solve a problem when all I needed was a set of pliers. It was all part of the simplification process. All along I knew women live a more complex lives than men but adjusting our existences to fit was the challenge. Ultimately, I needed to accept the challenge to save my own life. On occasion, the complexities of learning a new gender world in my femininization process became too much and I needed to try to fall back and take a break. However, breaks were short because the more I learned about being a woman, the more I wanted to learn which was aided to a large degree from finally beginning gender affirming hormones. The new hormones simplified my life even further by aligning my inner and outer selves. 

Suffering through all the complexities of transitioning genders turned out to be so worth it for me. The long journey I took led me to a much simpler world I wish I had be able to know years ago.

Dsyphoria is Never Pretty

Image from Jen Theodore on UnSplash.

It was years before I knew what gender dysphoria was all about and what it meant to me.

Essentially what it meant was understanding the depth of how far I wanted to go towards my feminization. I started out innocently I thought, similar to most of you, with explorations into Mom's wardrobe. and makeup. I wonder if she even noticed the fascination I had watching her put on her makeup. 

All along, I wondered what was going on with me and was I the only one who felt the same as I did. On those days, my gender dysphoria ran deep even though I still had no idea of what my future held. I looked in the mirror and saw a male even though on some days I felt decidedly I wanted to be a girl. In fact, if you had asked me then what I wanted to be when I grew up, I would have said a successful woman. Sadly, there were almost no successful transgender women to model myself after, so I internalized my feelings and carved out a very tentative life as a male. In fact painful internalizing became a theme in my life and led to further gender dysphoria.

All of a sudden, as my life progressed and more gender information became available, my dysphoria became more in focus. I could see what the problem still was but I still wasn't in any position to do anything about it except cross dress my life away. I knew deep down, I did not want to harm anyone, especially myself. However, when I still saw my male self in the mirror in the morning, harm still came. The more I attempted to cross dress my dysphoria away, the quicker and stronger it seemed to return just wrecking my mental health.

The only thing which kept me on any sort of a feminine path was when I expressed my female side to myself, I felt so natural. I felt from that reason alone, I was doing the right thing which in turn positioned me in direct opposition with my male self and increased my dysphoria to the max. Because my male self was fighting back with all the tools he had. In those days, he held all the cards, making life miserable for me which sadly I passed along to those people closest to me. I did everything I could to relieve the stress and live a pleasurable life. 

As fashion and makeup became easier for me as far as going out and entering the world as a novice transgender woman but more difficult when I needed to re-enter the world as a guy. My job did not make it any easier because I was in a very male dominated profession. I would do quite a bit of day dreaming of my other life while I was working in my reality. I even was quietly embarrassed when someone would mistakenly refer to me as a woman when I was working as a man. I figured my "aura" was overpowering female on those days and tried to project female more when I was out in the world as a transgender woman. I believe projecting my gender became an important accessory to be added to present successfully. Which I still do.

Still my dysphoria persisted and does to this day. Some days I wake up and sneak a peek in the mirror and see a feminine person which makes me happy. Other days, I see the same old male person I had ever been and become depressed. From there I have learned to take the middle road, or nothing is as good or bad as it seems including my dysphoria. 

At my advanced age, I seriously doubt I will ever be finished with my transgender dysphoria. Since I have an aversion to any extreme facial femininization surgeries, there will be no radical moves to change what I have to face the world. Dysphoria be damned, I will do the best I can.

Transgender Reconnections

 

Image from the
Jessie Hart
Archives

As I followed the path to a transgender transition, I made several important reconnections. 

Little did I know or realize how many twists and turns I would take before I found my truth. Most importantly I needed to realize I was not a man cross dressing as a woman, I was the reverse. A woman trying to make it as a cross dressed man in life. Because of that, nothing seemed to quite fit in my life as I struggled to survive in an unwanted male world. As I attempted to outrun all my problems,  I drank alcohol to excess as well as moved around and changed jobs way too much. I was always running, searching for my transgender reconnections. Sadly, I searched for nearly a half a century before I was able to have any success and connect with my authentic gender self.

During all those years, I was teased with success as I left my cross dressing mirror and slowly entered the world as a novice transgender woman. Along the way, I made all the mistakes I could think of plus some I could not have imagined happening. In my haste to reach the conclusion to my reconnection, I needed to first discover what it was. Through it all, my inner female was screaming at me for more and more attention but my male self did his best to play all his cards and hang on. The game they were playing wrecked havoc with my mental health and I sought out therapy for help. As with anything else, therapy is what you put into it and I went through several very good therapists as well as a couple not so good ones. Then there was the problem of me listening to what they had to say to start with because my male self was telling me therapy was just a waste of time and money. On the other hand, my female self saw the benefits, especially if the therapy process was slowly opening her world at all. 

Sometimes too, reconnections were tantalizingly close. There were so many days or nights when I could relax and enjoy a glimpse of what a life as a transgender woman could be like. The more reconnections with a feminine world I could make, the more natural and better I felt. Probably, most importantly, all of the gender progress I was making was because I believed in myself and my confidence was building. I had escaped the basic confines of the wardrobe and makeup challenges and made it to the one on one communications I was suddenly faced with as a trans woman. It was during this point of my transgender reconnection process I learned the most. Mainly because, I was relaxing and letting my long hidden female self take over. It turns out all those years of having to quietly sit back and watch my male self struggle enabled her to be a better person when she got the chance. 

When I reconnected with my female self, I was able to be a full person again and I knew one of my therapists said it right when she told me there was nothing either of us could go about me wanting to be a woman. If I had followed her advice and set out to discover what my second wife had told me all along, I would have taken the time and really looked into what a women's world was all about. Other than the outward appearances of fashion and makeup. It was the biggest reconnection I couldn't make until I had earned it by actually adopting and living a life as a trans woman. Even to the point of beginning HRT or gender affirming hormones. 

In many ways, the new hormones were the final piece of the puzzle in reconnecting my transgender self to the world. Physically and emotionally I was ready to face the world as a united human being.  

Down the Transgender Rabbit Hole

 

Image from Benoit Baumatin on UnSplash.

Long ago, I sought out a rabbit hole I found I did not want to escape.

In the beginning, I did not go deep into the hole so I could supposedly easily escape if I wanted to. The farther I went, the harder it was to escape even I wanted to. What happened was gender euphoria set in and the entire cross dressing experience became increasingly pleasurable as well as feeling incredibly natural. The problem I faced was how to cover the entrance to my rabbit hole so no one else in my family could discover it. Very early it was easy when I could attempt to borrow select clothes from my Mom's closet which ended when I became too big to wear them. Then I had to rely on my own limited financial resources to buy fashion and makeup accessories. 

For awhile, the pressure to go away and cross dress became so intense I needed to find a spot away from the house to establish another private rabbit hole. I found the best spot in a quiet wooded area next to our rural home. I was able to protect my secret collection of feminine clothes in plastic bags and hope they would be protected enough as well as not be discovered. I did well, because they never were and I was provided another place to go to cross dress. If even for a short period of time. 

The better I became at perfecting the "art" of fashion and makeup, the more I wanted to leave my novice transgender rabbit hole and look around at the world. At first, the world proved to be a very difficult place to be. After too many public failures I was sent scurrying back to my rabbit hole to seek comfort and try to figure out what all I was doing wrong with my feminine presentation. The entire feminization process for me proved to be a difficult one as my entrenched male self fought for his dominance and kept on trying to cover up my rabbit hole with ill advised purges. Very quickly he found out the gender purges I was going through were a complete waste of time and money. 

Once I reached the middle portion of my life, my rabbit hole needed to be expanded from a crossdresser rabbit hole into one large enough to contain a full fledged transgender woman. I needed room for more wigs, shoes and women's essentials to survive in the world. As I was entering a new exciting yet scary world without my white male privilege, the sunlight outside my rabbit hole was at times blinding. Even more so when the world all of a sudden expected me to communicate with them when at the least, I had to order face to face with servers or bar staff trying to take my order. What was a novice trans woman to do? What I attempted to do was make the best of a potential destructive situation. Very early in the game, I came to the conclusion the world knew I was transgender for the most part and those who cared, could just get over it because I was just living my truth.

Of course, once I was able to leave my rabbit hole in my past and live, I had no desire to go back to it's dark confines. Each time I was successful in the feminine world, my male self lost more and more of any control he had left. 

The writing was on the rabbit hole wall when I started gender affirming hormones. I knew I had made the correct decision when my body and mind took to the new hormones so naturally. In addition to all the bodily changes which took place, I cherished the new emotions I felt. Being able to cry for the first time in my life was quite the experience. 

Perhaps, most importantly, was when I discovered the lack of predators I really had when I left my rabbit hole. Of course dealing with the occasional man was a problem but with my circle of lesbian women friends, not so much as they taught me true validation as a person. Once I learned to validate myself, I was freed from my old male rabbit hole for good and jumped into the sunlight.

Poor Executuion equals a Hot Mess

Image from Author, Columbus, Ohio.

More times than I would care to remember, evenings when I went out to explore the world as a cross dresser or novice transgender woman turned out to be a hot mess. 

Particularly frustrating were the evenings or days when I thought I had planned everything out so well. I picked out the perfect outfit and applied my makeup just right and was ready to go. Perhaps my biggest issues had to do with figuring out where I was going to go and when I needed to be back before my wife returned home. Did I have a relatively long time to explore the world, or a short time to visit a few of my favorite venues and be back in time to remove all vestiges of my makeup and attempt to return to my male life. 

In the beginning, big mistakes would appear to ruin my time and turn it into a hot mess. I did not understand because I thought I was doing my best to put my new feminine cross dressed image to the public test. Some of my problems came from taking too many chances and others came from just purely being new to the world. Examples of taking a chance came when I used water balloons as breast forms, knowing full well how fragile they were. Predictably, one broke when I was out in public, making a huge mess in a rest room I was in. The only good thing which happened was, the room was empty except for me and I was able to clean up my mess and exit before anyone else came in.  From there, I learned the hard way to invest in silicone breast forms which I was able to use until I was able to grow my own breasts with gender affirming hormones. 

Other mistakes I would put under the title of ill-advised were the times I was simply having too good of a time and lost track of what time it was. Those were the evenings, I came home and ran directly into my second wife who was not amused. A huge fight always ensued until she settled down days or even weeks later. The whole process was not pleasant and just kept repeating itself essentially until just before she passed away. Finally I decided to purge my trans-feminization self and grew a beard for the last six months of her life. During this time, I didn't know she was as sick as she was and she passed totally unexpectedly and I often wondered if we could have stayed together for any length of time had she lived. All I do know was, I was making a hot mess out of our life because of my transgender issues. 

During this time also, I was desperately trying to catch up with all the small issues a woman has done to live her life. I did so many things such as wedging my heels in sidewalk cracks, which of course destroyed any image I was doing my best to project as a confident well dressed professional woman. 

Through it all, my wife still prodded me on by telling me I still didn't know anything about really being a woman. I wasn't able to learn until later how correct she was. My excuse is I wasn't allowed to play in the girl's sandbox until I earned it. I compare the process to being able to land a job by finally having all the qualifications needed. Until someone gives you the chance to move up, you have to earn your way or you never get the chance. I was always under qualified to play with the rest of the girls until I forced my way in.

Getting there wasn't easy. I needed to find a group of women I could learn from and not be judged at every turn. I also need to locate women who had no knowledge of my previous male self. He was never mentioned and most certainly, I never brought him up. When I did my life became so much easier. I did not have to worry about my transgender execution and hot messes became increasingly a part of my past.

A Night at a Concert

Image from the Jessie Hart Archives

Following the time when my wife passed away, I actually tried to date another cis woman, once.

During this brief period of my life, my old male self was still desperately hanging on to the idea he could still exist at all. At that time, one of my servers came into my restaurant with her very attractive Mother. After several inquiries I found her Mother was single and she would ask if she would go out with me. She did and we started our very short history of dating. 

Right from the start I found she was a bit of a prima donna when we met on a date in downtown Cincinnati. I suggested stopping at a micro brewery for a quick appetizer when she wanted to go to an upscale steak house on my dime. I should have known then she was out of my league but I kept on trying anyhow. In a very short period of time, I told my daughter I was dating again. In response, she came up with two tickets to a local park pavilion near her house. The concert performer was Joe Cocker, so I could not wait to go. I even asked the new woman I was dating if she wanted to go and she initially said yes and the date was on, or so I thought. A couple days later and a week before the concert in the park, she called me and broke up our brief affair. I was slightly shocked but then again not so much as I began to consider what I would go with an extra ticket to see Joe. 

At the time, I was increasingly exploring the world as a transgender woman, so I thought why not take myself on a date in the park. I knew exactly what I would wear .My long silky black slacks with my black matching sleeveless top and black flats for comfortable walking. I then applied my makeup and topped my outfit off with my long black straight wig and I was ready for the half hour drive to the venue. By this time all of this happened, I was becoming very comfortable with my feminine self so I was really looking forward to the evening as it approached. I had spent many a evening being alone with myself. I wasn't very nervous as much as excited by the expectation of having a good time. 

The evening of the concert turned out to be ideal weather wise, a beautiful warm but not too humid Ohio summer evening. I showed my ticket and was admitted to the venue without a problem. Before I went to my seat, I decided to buy a drink and then headed to sit down. Again I experienced no problems with anyone in the venue in my section. I was able to enjoy my drink and relax even further before the music started. I especially enjoyed the silky sensation of my clothes in the summer evening air.

I was glad I went because I had been a Joe Cocker fan since the Woodstock concert days and it wasn't too long following the concert, he passed away and I was still able to be completely enjoy his performance before it was too late.

As far as I was concerned and as selfish as it may sound, the whole exciting evening was more fun for me than taking a woman I barely knew. Plus my experience even further increased my confidence as a novice transgender woman. Even to the point of coming out to my daughter who I told that I enjoyed the concert very much but never added who my "date" was. 

The night at the concert was one of those lifetime experiences I will never forget. It was the last time I ever tried to date as a man and the first time I was ever to seriously explore my life as a transgender woman. Once I did, the more I understood it was the life for me. 

Bad Gender Decisions

 

Image from unknown origin. 

I often wonder if during all the writings I do, as I  describe how I succeeded in living my dream as a transgender woman, do I emphasize the bad decisions I made. 

Needless to say, I made plenty of choices I wished I had back to try again. First of all, I suffered from the same problems nearly all novice cross dressers or transgender women go through. Unlike cis gender girls our age, we didn't have the peer pressure or knowledge to help us be girls or women. We were not invited to the sleepovers where the girls experimented with makeup and clothes and it showed. I equated the whole makeup process to painting model cars when I was growing up. It took lots of practice to get the basics right. In the meantime, as I learned, many times I made bad decisions and came out looking like a clown. This was especially true with the clothes I chose to try to wear. I tried way too long to force my male body into clothes designed for sexy teenaged girls and I paid the price when the mirror lied to me and I tried to go out in the public's eye. 

When I was laughed at in public, I knew my feminine life had to change for the better if I was ever going to be able to survive. I just could not keep coming home in tears after another night out making bad decisions. Certainly. the process was not improving my deepening gender dysphoria. In desperation I sought out help from one of the only known gender therapists in Ohio at the time which was a good decision. The bad decision came when I decided to not listen to what she told me. She told me there was nothing she or I could do concerning my deep seated desire to be a woman. I would have to learn to live with it. If I had not been so hard headed and stubborn, I would have taken her advice and prepared myself for a life as a transgender woman. 

Once I started to really explore the feminine world, I made plenty of bad decisions. The primary example was when I became comfortable in presenting in places such as clothing stores, book stores and malls, I would always challenge myself to do new activities as a trans woman. Activities where I had to face the public and communicate one on one with the world. By doing so, I knew sooner or later I was going to have to challenge myself and use the women's restroom. Nature was calling and I knew I needed to answer the call. 

I started the process innocently enough by using the women's room in one of the bookstores I went to on a regular basis. I would do my best to make sure the room was empty before I went in and took care of my business. I was fortunate in that I read about and knew quite a few basics women follow when they gather in the restroom. I also knew from my experience in the restaurant/bar business women were not always the pristine gender they are known to be but that is another story. As well the other basics I needed to learn such as looking other women in the eye, washing my hands and stopping to adjust my hair and makeup. 

For the most part the only bad decisions I ever made as far as rest room usage was concerned was which rest room venue I decided to use. On a typical night, I would plan to go to my regular venues  plus maybe try out a new place. By this time, I was becoming fairly secure in my presentation to the point I wanted to try to challenge myself. I decided to go to a borderline redneck venue, order a couple of beers and try to use the restroom before I left. Before I knew it, someone had called the police on me and I was told to leave. Which had to be the worst decision I ever made. From there I went back to my usual regular venues and everything was back to normal.

Normal for me was difficult to change. I was so use to pushing my boundaries as a novice transgender woman, I had a difficult time adjusting my life when I no longer had to push so hard. I was enjoying the fact I did not have to face making bad gender decisions to begin with.

Opportunity Knocks

 

Civil War Cemetery image
from the Jessie Hart Archives
 

In my life I have found several really rare times where true opportunity actually knocked on my door. 

As I indicated, the situations were exceedingly rare and required split second decisions on how I was going to proceed. Possibly the first main one happened when I went with the "A" list trans women from the cross dresser - transgender mixer I was at in Cleveland. It was the night I gathered my courage, put on my big girl panties and was able to enjoy a professional makeover at the mixer. The result was I looked better than I ever had in my life and really wanted to claim my spot with the other impossibly feminine women in the room who were planning to continue the meeting with going to gay venues afterwards. At the second venue we went to, for the first time in my life as a woman I was approached by a good looking man who wanted to socialize. Since I was in a city I knew nothing about and with acquaintances who were about to call a taxi and leave, I decided to turn his advances down and leave. I often wonder what would have happened if I had stayed. What sort of opportunity if any, did I miss?

 Most likely, the second opportunity I did take advantage of was when suddenly I decided I had had enough of cross dressing and wanted to follow my gender instincts even further. It was the night I was determined to go out and blend in with a group of young professional women at an upscale bar/restaurant I had frequented several times as my male self. More than anything else, I wanted to see if I could blend in with the group as a transgender woman and enjoy myself. Perhaps what I remember most about the evening was how scared I was as I waited in the parking lot constantly checking my hair and makeup before I gathered the courage to go into the venue. As it turned out, opportunity did knock that night. I enjoyed myself after I could take a normal breath again and I knew my life as a casual cross dresser was gone forever. I needed new horizons to conquer as a novice transgender woman.

As I settled into attempting to find my way as a trans woman in the world, I tried to try different venues and situations to deal with. Some were successful, some were not. The ones which I can remember the most were the times I tested going to more or less red-neck country venues. I quickly discovered I wasn't welcome and moved on quickly but not before the cops were called on me a couple of times. No opportunity to succeed in those places for sure and I never went back.

Perhaps the biggest opportunity which came knocking at my door was when I had the chance to begin gender affirming hormones or HRT. At my age of sixty, I wanted to make sure I wasn't going to harm myself, so I took the proper precautions and sought out a doctor to prescribe the medications I had waited for so long. Fortunately for me my health proved not to be an issue and I was given minimum dosages to get me started. Seemingly, my body took to the hormones like I always should have been on them and new changes started almost immediately. In no time at all, I was moved up to a higher dosage and my new changes took over my body. So much so, I needed to move up my transition timetable when my hair started to take off and grow along with my softening skin and protruding breasts. 

Then, the most unexpected opportunity happened when I met my current wife Liz on line nearly fourteen years ago. At my age and transgender history, I was prepared to spend the rest of my life alone and especially never expected to ever be married again. Opportunity was telling me to never say never and here I am.

I have a very hard head however and many times opportunity had to knock loudly to get my attention. Often because I was stuck with life changing conditions where I could lose everything. I tried to fall back on my inner self and hope for the best and finally I let her lead me the right direction. 

Ownership, Skeletons and Politics?

 

My daughter's favorite saying used to be something to the fact if you have skeleton's in the closet you better make them dance. Which could describe many politicians in Washington DC.

This post however is not another rant on my part about politics. If you follow me at all you know I am solidly behind the Biden-Harris ticket and believe tRumpt and his cohorts want to erase transgender people everywhere. As well as do away with our democracy. But, as I said, this post is not about politics, it's about my life. 

In my case, I spent most of my life trying to change the inevitable. I was transgender and should just relax and make the best of the situation I found myself in. By cross dressing my life away, the only positive I can come up with is all the practice I put into the art of feminine makeup and fashion. It wasn't until I left the mirror and started exploring the world, did I begin to own it. The whole process turned out to be a blur and actually happened faster than I dreamed it would. In other words, by interacting as a transgender woman in public, I was teaching the skeletons in my closet to dance. 

The dance moves became more and more intense when the public wanted to invade my little private world and know more about me. First of all, when I finally moved from the easy clothing stores in the malls I used to shop at and into food venues where I would stop to eat. Then I found myself needing to communicate with servers and bartenders one on one as I was scared to death. At first I tried to mimic the range and tones of the women I was speaking with until I found I could take advantage of feminine vocal lessons at my local Veterans' Administration hospital. Slowly, I gained enough confidence to get by in the world. I was coming to realize I could not change who I truly was, so I better learn to know her better. When I did, I enjoyed the person she was, My feminine inner soul went way past just trying to look good in the mirror and do a better job with my makeup and fashion. I found I could just let her go and I could set back for a change, watch my skeletons dance and enjoy the show. For the first time in my life I did not have to feel guilty about the person I was becoming.

In addition to having less guilt, I was having the time of my life. For the first time, I was making new friends who had no connection at all with my old male self. My small core group of mainly lesbian women friends taught me more about owning who I was than they ever knew. I was validated as a transgender woman through them mainly because they saw me as me. The freedom was remarkable. 

Perhaps I could say I transitioned to my authentic self  not so much because of my friends but on the other hand, I started to own my life and live it with my friends. I was teaching my skeletons all new dances when I let them out of the closet. As always my old male self was resisting losing his grip and it took my wife Liz to send him away. When we first met, Liz barely knew what was left of my former self and she told me she never saw anything remotely male about me. That was it and from then on I went all out to own who I really was. 

See, I told you this was not going to be a political post, Now if you will excuse me, my skeletons are dancing for the public to see.  

Growing into the Problem

Image from Karla Hernandez 
on UnSplash.

 Back in the day when I was growing up as a young gender dysphoric person, I felt I had been able to hide my femininization efforts from the rest of the family.

For years and years, I lived under the impression I was successful. After all, I was doing my best to compete in all the basics I needed to fit with a demanding, unwanted male world. I was born into an extended male dominated family, so there was considerable pressure to conform as one of the oldest sons of three competitive uncles. 

Along the way, my main goal was to properly hide my small but growing collection of feminine clothes and makeup. I used every cent of my allowance money plus money I earned from delivering the local newspaper to rural neighbors. I thought I was successful because I was never confronted by primarily my Mom about what was going on with me. Remember also, this all occurred during the late 1950's and early 60's. Information on gender issues was for the most part non existent and was considered to be a mental illness which was even worse. 

I think now, if indeed I was ever "discovered" as a truthful cross dresser, my Mom who essentially took on the major role of raising my brother and I, just decided I would just grow out of it. Plus, she may have thought I had some sort of fetish for woman's clothes rather than the deeper issue of wanting to be a girl. It could be described as kicking the rock or can down the road just hoping it would go away.

Instead of going away for me, I grew into the problem but it took me years of wasted time and effort to take advantage of my gender growth spurts. I say "spurts" because of the time I took fighting my transgender issues at all. Keep in mind too, I am referring to at over a half century of my life. Quite a bit of time to consider mistakes and successes when it came to accepting and then growing into my considerable gender dysphoria. For me, gender dysphoria could be described as looking in the mirror one day and seeing a feminine face then the next seeing a masculine one. The whole process just destroyed my fragile mental health. At the point, I sought out therapy to help me. Which provided me with various amounts of relief. 

I had one male therapist who told me to ignore the problem, all the way to a gender therapist who told me the truth. I needed to learn to live with being transgender because it wasn't going away. Easier said than done for me because I was too stubborn to listen to the advice I was paying for. 

True gender growth for me didn't really begin until I started to escape my dark closet and began to explore the feminine world. Of major importance was the fact I finally outgrew what I call my cross dressing fashion adolescence. In other words, I stopped trying to dress as a teenager who was able to wear revealing or even sexy fashions. On the other hand, I just looked ridiculous or even trashy. Once I learned to dress for my age and body style, my presentation as a novice transgender woman improved and my new public life improved dramatically. I was growing into my so-called gender problem. I grew so fast, plus with the help of others, I discovered I didn't have a problem at all. 

Once I grew into my "problem" I discovered a wonderful world I had only dreamed of. I was even able to bring a substantial amount of my old male life with me and carefully weave it into a new existence previously dominated by my old male self but then taken over by my new feminine one. She quickly proved to me, she knew what she wanted in life and had learned from all those years of  rejection. She was like I told you so. 

Now I am not sure all the time and effort I took to grow into the problem was worth it. Many times I wish I wasn't so stubborn and had taken the time to listen to my feminine reality and just went ahead and transitioned into a transgender world.  

As always, thank you for following along with all my experiences here on the blog! I appreciate your time!  

My Second Gender Transition

Liz on Left. Image from a Banquet we 
attended. From the Archives. 

 I am a firm believer,  I went through more than one major transition when it came to building a new life as a transgender woman. Many transitions were helped along by friends and others I accomplished on my own. 

One of the biggest I did all by myself was one I mention quite often. It was the night I went to TGIF Fridays close to me. Just going was not so amazing, in fact, I had been to the venue many times as my male self. When I was there, I often was very jealous of all the other women I saw there, many of which were dressed in fashion I could only dream of. 

All of a sudden, I decided to make my dreams a reality and one night I set out on an adventure which I would never forget and would change my life forever. I can't really tell you why but something clicked deep inside me and I decided it was time for me to move away from being a cross dresser and explore my possible existence in a transgender world. The whole possibility terrified me more than anything else I had ever tried before in my life. Possibly because I knew if I was successful there would be no turning back. 

To begin with, I had the wardrobe I needed to wear to blend into the feminine environment I was headed. I knew the Friday's venue I was going to had a very woman based clientele which came every night at approximately the same time from a large mall which was nearby. I knew exactly, who I was trying to blend in with when I chose what I was going to wear. I chose my dressy black pantsuit, black flats, sensible makeup along with my shoulder length honey blonde wig. I felt I looked presentable enough to accomplish my goal of moving into the transgender world I was just beginning to explore. 

Once I came up with a time I could sneak out for a trip into the unknown when my wife was working late, I began the transformative femininization process. Once I thought I looked fairly presentable, I left for the twenty minute trip to the venue. Through it all, I was scared but not as scared as I would be when I arrived at the Fridays. When I pulled into the parking lot, I ended up waiting over a half a hour as I adjusted my hair and makeup in my car's rearview mirror. Once I came to the point where I could barely breathe, I opened the car door and gathered myself the best as possible. After all, I had improved from the point of not being to breathe at all to being able to walk in the front doors. 

Since I managed a similar casual dining venue to a Fridays I knew the setup, Essentially, once I made it past the hostess stand, all I had to hope for was being able to find a vacant seat at the bar. I was lucky I arrived shortly before the rush and there were several seats available. The Fridays I was going to had not remodeled yet so it had two big supports on either end of the bar. I was so scared and so lucky, I was able to get a seat next to one of these supports. I got as close as I could and tried to hide until I was approached by a friendly bartender and order a drink. From that point forward, I knew my life had changed forever. Just existing as a woman among other women in a public setting had removed any idea's of being a casual cross dresser ever again. 

In a moment, my second gender transition had taken place. My first came years previous in my youth when I viewed myself as a girl in the hallway mirror. Plus, deep down I knew the next transition I would undertake would be if I could ever undertake gender affirming hormones or HRT as it was known as back in those days. My visit to Fridays that night jump started my gender future. My problem then became how I would ever be able be able to co-exist with my un-approving wife ever again. She was certainly against being with another woman. Especially if the woman was me. So my second transition was heaven for my inner woman and hell for my wife and my marriage.  

Of course, I was able to transition even further with hormonal therapy and go on to lead a comforting transgender life. Going through the process was always not the easiest and I will always remember how I felt that night at Fridays from trying to hide behind a post all the way to how my panty hosed feet felt in my flats. It was quite the evening.

Trans Crisis Management

 

Image from the Jessie
Hart archives. From the Ohio 
State Student Union. 

Over the years as I went through the process of living my life as a transgender woman, I encountered many instances of crisis management. 

Some of the encounters were funny, some were anything but funny. Several come to mind as I write this post. Probably the most humorous account came at the ill fated expense of a water balloon I used as a breast form one night when I was going out to my regular venues I loved the feel of the balloons. They provided a realistic bounce and even matched my body temperature if I filled them with water of a certain temperature. Of course, as I was doing all of this, I knew how fragile my fake breasts would be. And, a night I remember well, it happened, one of my beloved water balloons broke sending water down my clothes. I was lucky in that I was headed from my seat at the bar to the rest room and had just made it to the safety of the women's room, if it was empty at the time. It was empty and it saved me from any rushed explanations of the water which I caused. The only crisis management statement I could come up with was I was pregnant and my water broke. What really happened was, I gathered my one breast self together and left the venue like nothing happened, then headed home determined to find another form of realistic breasts. 

The next  profound crisis management encounter I remember was one of the worst I ever have had. It happened in another venue I went to regularly. After consuming my usual amount of beer, I naturally needed to innocently use the women's room. When I did, I didn't notice the woman who came in after me and I should have. I saw her and an older woman  I perceived to be her Mom come in the door and pass nearby me at the bar. The older woman wasn't shy about glaring at me but kept on going, minding her own business. I should have known my relaxation would come back to haunt me because when I came out of one of the stalls in the restroom, I was confronted by the daughter. Out of the clear blue sky, she started screaming at me and began her tirade by calling me a pervert. 

At first, my fight or flight mechanisms kicked in and my first inclination was to vacate the rest room. Instead, my inner female kicked in and faced the red faced screaming woman. Somehow during her rant, I was able to learn she ran her own hair dresser salon. When she slowed down, I asked her for a business card so I could pass it along to a very influential local LGBTQ organization and naturally tell them about my negative experience with her. It worked because she abruptly stopped and left the rest room while I not so calmly washed my hands, checked my makeup and returned to my seat. The whole experience taught me to always be aware of my surroundings and other potential problem people in it. 

Of course, these two examples are just the tip of the iceberg when it comes to dealing with our own brand of trans crisis management. From makeup and fashion  struggles when we first come out of the closet, all the way to unwanted government discrimination, we face it all. I am sure all of you have faced your own crises over the years. Maybe going back all the way to being caught cross dressing in your Mom's or sister's clothes when you were growing up. Surviving it all was the challenge while preserving our mental health. Sadly, with the extremely high rates of suicide in the transgender community, too many don't make it. In fact, we just had a local trans musician commit self harm and die last week. 

Crisis management with all of us just needs to be a priority. 

Leaving me For Years

Image from Brock Wegner
on UnSplash

I become a little amused when someone thinks I overnight completed my gender transition from a fairly successful male to a struggling novice transgender woman. 

To put everything in perspective, it took me nearly half a century to figure out my gender issues and how I needed to deal with them. Perhaps you noticed I used the word needed and not wanted because deep down I knew I never had a choice in my life. My gender journey was pre-written for me and I just had to follow the script.

For me it meant dealing with years of extreme gender dysphoria which wrecked my life and several relationships along the way. It was an extreme struggle for dominance from the two binary genders which lived within me. Naturally, even though he wasn't happy or satisfied, my pre-destined male life just didn't want to give up all the male privileges' he had worked so hard to gain. While, on the other hand, my feminine side had to put up with the fact she felt so free and natural when she was let out of my gender closet. 

The struggle left me in a situation for years where I couldn't win. I was in some sort of a gender trench warfare when one side had a little success, the other side would come back to reclaim victory. Battles were won, purges were made but the war went on and on. First I tried to hide in the mirror but that didn't work when I began to escape into the world as a cross dresser. All of a sudden, I discovered I might be actually able to live a dream life as a transgender woman if I worked hard enough to do it. At that point, I sat out to take better care of myself and lost nearly fifty pounds so I could fit into the woman's fashions I so admired. Plus I started to take better care of my skin so my makeup was easier to apply and I looked more natural doing it. 

At that point, I tried to outrun my gender dysphoria the best I could by changing jobs and locations where I lived way too quickly. In a space of three or four years my second wife moved from our home in Ohio to the metro NYC area, back to a very rural area where we heated with wood and finally back home again. All I finally learned was I couldn't out run my problems. They all began and ended with my gender issues. 

Even with all the problems I mentioned, I still did not want to give up totally on my male self. In many ways, the life he had carved out from such a bleak beginning was just too comfortable. What happened then were the years I spent as a novice transgender woman. All of them were scary yet exciting times to live through. 

So no, my decision to leave the male world behind was not an overnight decision. It just turned out he was leaving me for years. 

A Transgender Inch Equals a Mile

Image from Jessie Hart Archives
Civil War Cemetery Cincinnati

Distances are often very blurry when it comes to beginning and pursuing a gender transition. 

The meaning wasn't lost on me when I began to remember what many of my more experienced dating male friends said when it came to discussing their girlfriends. The biggest complaint was when the guys gave in an inch with their women, the women took a mile. 

As I transitioned into the feminine world, often I thought the same thing about my inner girl self. Or, as soon as I cross dressed in front of the mirror, the more she wanted. Specifically, she wanted out of the mirror and into the world. Quite early, it meant making the trip to the mailbox to check to see if there was anything in the box. I so enjoyed the feel of the outside air on my freshly shaved, panty hose covered legs. 

What I discovered was as soon as I made the very short trip out of the door, my girl dreamed of doing more and more in the world. So much so, my entire life was effected to the point I would become very grumpy almost to the point of disorientation when I couldn't cross dress again. The whole process just didn't seem fair because I was doing the best I could with the very limited resources I was able to put together. Fashion was difficult to find for my rapidly growing body but I could manage to buy my own makeup with my very small allowance I earned plus the money I put together from having my own newspaper delivery route.

Through it all, I managed to get by when my inner trans self wanted to take an extra mile when I was giving her an inch. I thought it was some sort of a gender poetic justice when my male friends complained about their girlfriends and I knew exactly what they were talking about when I wasn't outwardly involved with a girl at all. 

It wasn't until much later in life when I could begin to give up more than just an occasional inch to my transgender self and discover all I was missing. More and more I was able to take the extra mile. Even though I was scared (or even terrified) to do it. Such as the first night I went to a "Fridays" bar/restaurant for a cocktail. I ended up sitting in the parking lot for a good thirty minutes checking my makeup before I gathered the courage to go in. Once I did, and began to breathe again, I was able to relax and enjoy myself.

At that point, I was very proud of myself and considered I wouldn't challenge my novice transgender woman for more. After all, I had just given her the mile she wanted and I thought she should be satisfied for awhile. Needless to say, none of that worked. Instead of going to the so-called gay venues she had been going to, she wanted more of the "Fridays" vibe she succeeded in. I found she could become a regular fairly easily by being friendly, minding her own business and above all, tipping well. All of a sudden, a new life was beginning. No matter how scared of it I was at the time. 

Perhaps the biggest transgender inch becoming a mile was when I started gender affirming hormonal treatment. In what seemed a very short period of time, my body femininized as well as my inner self. I was feeling more emotional than ever before in my life as the new hormones took effect. The whole process was close to running a record setting mile. 

All along, my old male self was fighting giving up every inch he could. Not wanting to lose his life and all he had worked for. It turned out, once I went all the way into an new exciting transgender world, he lost the battle and the victory belonged to my stronger half. My feminine self as she took the final mile.

Walking the Transgender Tightrope

 

Image from Johannes Plenio on 
UnSplash

I have never been accused of being coordinated at all which completely held me back when it came to me being able to participate in any sort of athletics except for football which often meant dealing with brute strength. 

Little did I know, I would have to develop my own sense of gender coordination to deal with my gender dysphoria. It turns out the better I became navigating the world as a novice transgender woman, the more balance I would need to survive in life. What happened was, the better I became with makeup and fashion, the more confidence I felt and in addition I was gaining the all important confidence to try more and more exciting yet terrifying experiences as my feminine self. 

Doing the more I could possibly hope for led me to trying to walk part of my life in my old male gender and part in my newer female one. My second wife even approved of a plan where I could have three days a week to leave the house dressed as a guy, go to a motel, cross dress as a woman and basically do whatever I wanted. Then dress back into my boring drab male clothes and come home. It didn't take long for me to become bored with this arrangement and I began slipping out of the house behind her back when she was working. Out of sheer willpower I needed to begin being more coordinated in how I was trying to run my gender conflicted life. There was really only one thing I knew for sure, I loved my feminine side and wanted to do more and more to let her out. 

Sadly, the whole process of trying to balance the two genders fighting for dominance within me was destroying my already bi-polar fragile mental health. I tried therapy and for years had only one therapist tell me the truth...there was essentially nothing I could do about wanting to transition into a transgender woman. I was what I was and I should accept it. Of course I wasn't smart enough to take her advice. I still wanted to save what was left of my long term marriage to my second wife while at the same time exploring what could be possible if I actually had the courage to transition into a fulltime world as a transgender woman. 

Finally, after falling off the tightrope more times than I can say, I could take the mounting gender pressure no longer and tried suicide as a solution. Just before my wife passed away from a massive heart attack, I thought I "purged" for the final time and got down from my tightrope. I grew a beard, gained a bunch of weight and overall was miserable but I gave it my best effort. 

I proved to myself I wasn't coordinated enough to navigate something complex enough as a gender tightrope and moved on to living a life as my authentic self. I am not one for regrets but if I allowed myself one, it would be I would have had the courage to transition earlier in life (before the age of sixty.) I would have saved myself so much time, effort and frustration as I attempted to balance my gender tightrope.