A Zig-Zag Trans Life

Party night at Club Diversity
Columbus, Ohio.

 Maybe I should have called this post I should have zigged when I should have zagged. Or vice-versa.

In many ways, I see all sorts of transgender women or trans men in the same situation. I started at a very young age when I would zig away from my younger brother when we were home alone and I was able to get away from him when I cross dressed by locking myself in the bathroom. Fortunately, I never needed to zag because somehow, he never caught me and told my unapproving parents.

Somehow I thought when I got older, my life would improve. The first thing I learned was my urge to be or at least cross dress as a girl my age would not magically disappear. In fact, it became stronger when I learned it was not just a phase and I began to understand my gender dysphoria better. At that point, I really had to start zigging and zagging just to maintain my fragile mental health. When I was old enough, I even began taking myself to therapists to seek out help. My only main success which came out of it was when I was diagnosed with a bi-polar depressive disorder. It had nothing to do with my gender issues at all. As far as zigging or zagging, I was able temporarily save my marriage and received my money's worth when my gender therapist told me the truth. She could do nothing about me wanting to be a woman. Overall, my desires should not be a problem and I should face my truth. Of course, I wasn't smart enough to follow her advice and resumed all the zigging and zagging. 

It took me years and years to grow up and away from my male self and settle into a life as my authentic feminine or transgender self. By this time, I was growing so tired of all the zigging and zagging I was going through. Even though the whole process was an exciting time of my gender life, I was still becoming fatigued by my life the way it was. Ironically, when I was, I settled into a long term set of appointments with a very understanding therapist. She talked me off the ledge several times and along the way helped me secure gender affirming hormones and the paper work I needed to change all the legal gender markers I could. All of a sudden, I was able to visualize myself living my dream as a full fledged transgender woman. With my daughter's help, we were even able to come up with a new legal name which would reflect my family history and would be easy for my grandkids to use.

Finally all my exhaustion came to an end and I was able to live how I pleased. All the zigging and zagging had worked. All the times I hurried to hide myself away from friends and family, were put behind me. Through it all I learned one difficult lesson. If you can somehow believe in yourself, you can live your best life. Even though you may (like me) take years and years to evolve into your authentic self, the trip is usually never boring as you lead a zig-zag trans life. Overall, it takes a ton of effort to weave your gender issues into a life of family, spouses, jobs and friends. You learn to be forever vigilant in protecting yourself and end up internalizing way too much of your life. It seems the entire process is just ingrained as part of a transgender life as breath itself. We just have to finally zig to get around it. Then zag to adopt your new life as a trans woman.

Time Waits for No One if you are Trans

Image from David Cohen
on UnSplash.

Sometimes I look back at my nearly three quarters of a century of life and wonder how I made it.

Often I think I could have made it easier on myself if I had been able to muster the courage to come out much earlier and live the authentic feminine life I always wanted to live. It is difficult to imagine exactly how it would have worked out, because the world has changed so much for transgender women and men. It is always worth mentioning the pre-internet/social media days when trans people were so much more isolated in their dark gender closets.

Timing always has quite a bit of influence on how anyone is able to attempt joining the world as an out transgender person. As anyone becomes older, they have a tendency to accumulate life experiences, material or not. Families come along for many, making the gender shock of changing genders so much more of a problem. Baggage continues to increase when we undertake better employment and secure better housing. Both of which can be very difficult to give up.

Time keeps on moving, which often is the only definite and when it does, the pressure builds to do something about it. The older we become, the more the reality of our mortality sets it and we lose the recklessness of youth. I was certainly much more reckless when I was younger and tried more self destructive acts such as consuming too much alcohol and driving way too fast. Also, as the pressure mounted, my mental health which was already shaky was put to the test repeatedly. Anything I tried seemed to take me farther and farther away from any potential answers I could think of.  

The problem was I couldn't see the forest for the gender trees. Similar to any other woman, my biological clock was ticking away and the older I got, the louder it became. I tried everything to run from my clock but of course nothing worked. Finally, when I turned sixty, I could take it no longer. On one momentous night after years of struggle I gave up my male self and gave in to living fulltime as a transgender woman. I put all the years of experimentation as a cross dresser behind me, dis-carded the remainder of my male clothes and set out to live my dream. Sure, it was scary but all the preparation I put into the move made it more natural and successful from the beginning. Primarily my inner woman was overwhelmed by finally having the final say in my life. 

At the time, I was viewing the entire process as jumping off a gender cliff and hoping for a soft landing. As it turned out, all my prep time when I was actually trying to play in the girl's sandbox worked well for me because I had a chance to build up a close circle of women friends who helped with the landing and even welcomed me in. 

I knew too, I wasn't getting any younger and if I put off a gender transition much longer, I would likely never have the chance again. I was close to retirement age, had no spouse to worry about, and had a limited amount of family and friends to come out to, so even I didn't have a good reason to stay in my gender closet any longer. 

In my case, for whatever reason, I was able to wait out time to the bitter end and come out positive in the process. I wish now, I didn't wait so long to live as my authentic transgender self and put so much prep work into it but no one goes back and gets a second chance to rewind the clock.  

The Power of Hope as a Trans Girl

Image from Dayne Tompkin
on UnSplash.

Of all the emotions, perhaps hope is one of the most powerful.

Especially, these days when the world seems to be coming after the entire transgender community, hope seems to be a precious commodity. In my case, I learned slivers of hope came in the form of brief gender euphoria, when I glimpsed the girl looking back at me from the mirror. She gave me hope I could keep trying to live my dream. 

Then I was forced back into my mundane drab male life I never really wanted and my hope disappeared. Often for long periods of time before I could cross dress again. I was in despair until I could glimpse my feminine image again in the mirror. Perhaps the worst part was I did not know exactly what I was looking for. More preciously, I did not understand the predictability of my urge to be a girl my age. If I was able to document it at all, it seemed every week at least once I wanted to cross dress and be feminine. Why did the euphoria of dressing not last? It wasn't until much later I would realize my answer was I was more of a transgender woman than anything else. 

In the meantime, I was busy watching the teen aged girls I so wanted to be like. Without being creepy, I noticed how they moved and what they wore. When I did, it gave me hope I could someday live my dream of being a woman. Even though I was a student of the female gender, life kept me stuck where I didn't want to be. Later I began to understand no one gets out of life without trauma and mine was an extension of being transgender. Learning to live with my trauma and still hope for better kept me going along with small periods of gender euphoria.

Initially, I took the easy way out by taking trips to mall clothing stores where everyone could present as anybody as long as their money was green and by going to gay venues where it was easy to get in. Later I learned in the gay bars, anyone was admitted but very few transgender women were ever accepted. Which made sense, the men in the gay venue were there for other men, not one who was cross dressed as a woman. I found the best I could hope for was to be accepted as a drag queen which I wasn't. 

The whole process forced me further into the world and gave me new hope for the future. I expanded my horizons past the mirror and into the life I write about so often. Surprisingly, I felt a new life as a transgender woman was possible so I started gender affirming hormones to allow the process to be easier. New friends who never knew my old male self helped me along more than they ever knew and the nights when I went out to be alone suddenly became to socialize with the world. My hope to achieve my dream was alive and well. 

However I felt about my dream coming together, the more I knew I needed to work harder to make sure it happened. For example, I needed to change as many of my legal gender markers as possible back in those days in backwards Ohio. With the help of letters from my supportive therapist, most of the process was surprisingly easy. 

Overall, the power of hope in my transgender life has been a wonderful influence but not a super power which was easy to find or nourish. The whole process took me too many years to accomplish what I set out to do because I did not have the wherewithal or even the courage to do it. Eventually, I did learn it would take more than just hope to fulfill my life dreams, it took action. 

It was All so Natural

Image from the Jessie Hart Archives. 

Even though I was facing tremendous hurdles as a cross dresser and/or novice transgender woman, everytime when gender times became tough, I kept on trying. Mainly because deep down  I felt so natural when I was cross dressed head to toe as a girl my age.

Although the time I was cross dressed felt so good, the length of time I was able to do it was never enough. Had I had more knowledge back then, I would have realized I was a transgender person. A big difference to me from only being a part-time male who enjoyed cross dressing in women's clothes. As I discovered more and more about myself, I discovered I was a woman cross dressing as a man during the majority of my life. I only knew I was not enjoying or was being fulfilled as a guy. The whole lifestyle never felt natural to me. 

As time went by, I increasingly followed the natural path no matter how difficult it proved to be. More often or not, I encountered very many severe twists and turns. Again, I was encouraged by the natural moments I experienced when I finally encountered the public as a trans woman. It was like the path had big sign boards along the way with directions on how to proceed. Or once I made it to a certain spot in my new gender life, I could set new goals. The example I always use was when I started to progress past just going shopping in clothing stores where they didn't care if I was a man dressed as a woman or not (because my money was green) and began to challenge myself in restaurants where I needed to interact one on one with the serving staff.  

From there, my goals became to refine and test my restroom skills if nature called during one of my longer outings. It was during some of my restroom visits when I  really needed to feel natural and spread my gender wings. I found out quickly I needed to be able to look other women in the eye and smile even though I was very scared. 

Through it all, I lived and was able to move forward towards new enticing goals of living life as a transgender woman. It was during this period of my life when I began to seriously consider moving forward with gender affirming hormones. Sadly, my second wife was very much against any idea of me being on hormones saying if she had wanted to marry a woman, she would have looked for one. In other words, she didn't sign up to live with another woman, trans or not. I loved her deeply and no matter how difficult it was, I tried to honor her wishes until her untimely death after we had been married twenty five years. 

Her rejection of any idea of me moving forward with HRT just put an extra strain on my mental health which in turn, led to a suicide attempt. Following the attempt, I tried yet another "purge" of my feminine wardrobe which of course didn't work. It wasn't too long after my final purge, she passed away very suddenly from a massive heart attack. As I write about often, her death was the ultimate shock to my system because I was always so self destructive there was no way I thought I would out-live her but I did.

When I did, I decided it was time to live my dream of being a full-time transgender woman. I took the natural path and never looked back.  

Afraid to Try?

From the archives. Underground
Railroad House.
Ripley, Ohio.

During my male to female gender transition, there were so many times I was afraid, or should I say petrified to try new things.

Probably, first of all, I was afraid to cross dress in my home at all. Fearing my family would discover my deep dark secret and I would be punished. Even with all the threat hanging over my head, I decided somehow I needed to try to move forward in my femininization. When I did, I felt so natural and felt I was doing the right thing. Regardless of my deep seated fear. 

Anyway you cut it, my fears cost me time and effort in my life. Precisely, all the time I spent attempting to work around other members of my family so it could be my turn to cross dress in the mirror. The amount of time I spent thinking and dreaming of being a girl was ridiculous. Finally the pressure built so much, I had to put my fears aside and dress as a girl. Even to the point of shaving my legs. In the long term, I became better and better in hiding my wardrobe and makeup away from my Mom, Dad and brother. To this day, I do not know how I escaped detection. 

The older I became, the more proficient I became at the art of wardrobe and makeup with what I could accomplish on my very limited income. My presentation as a girl became a very real possibility but not a possibility which calmed any of my major fears. In fact, some of them were even worse. Such as how was I going to be able to live a successful life as a man when I wanted to be a woman. Plus, what was I going to do about the looming chance I would be drafted into the military and sent away to Vietnam and what would I do if I couldn't cut it in college and flunked out. I spent many sleepless nights worrying about those things and more.

More to me happened when I was in college and I started to work my way into being a novice transgender woman. In those days, presentation or appearance was always the main issue since the only time I was really out was Halloween parties. Only being out once a year put a tremendous strain on me until I couldn't take it any longer and began to sneak out of the house dressed as a woman. Initially at night in lonely places before I knew the threat of doing things like that and jeopardizing my personal security. In the meantime, I still remember vividly the first time at night when I caught my reflection in a nearby store window when I was seriously thinking about going into a nearby book/magazine store and shop for a book.  I did not because my fears got the best of me and I was overwhelmed. 

It wasn't until much later when I was able to conquer those fears and come out into the world as a transgender woman but it wasn't without complete panic attacks on occasion. The one I remember the most was when I was thinking of making the jump from serious cross dresser to transgender woman in the parking lot of an upscale sports bar/restaurant I had been to many times as a man. I must have sat in my car for a half hour looking at myself in the mirror trying to gather the courage to go in. I don't know now how I did but I somehow put my fears behind me and went in. By doing so, my life changed forever for the best. I thought.

What really happened was, I set off a new round of fears because my male self (as well as my second wife) were digging in against me becoming anymore of a trans woman than I already was. While I was sure HRT or gender affirming hormones was my next step, my naysayers were against me. All of the process added to my fears of ever transitioning full time which increasingly my mental health was telling me was the only way to proceed. 

All of my new fears even took a back seat to my new everyday life as a transgender woman. At this time, the world was so new and different as I was learning so much as I built a new life. I hated for the old embedded fears to hold me back but they did. No matter how far I had come, the farther I had to go. Major issues such as finances, family, relationships and even sexuality had to be decided before I could move one.

 Fortunately, I put my fears behind me and conquered each of  my major conflicts as they arose. Victories equaled more confidence to achieve the transgender life I had always dreamed of. When I looked back, most of my fears seemed to be so petty. They certainly weren't at the time and became major mileposts on my gender journey.

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.

On the Transgender Precipice

 

Image from Wira Dyatmika on
UnSplash.

As I followed a winding, difficult path to my dream of living as a fulltime transgender woman, I took years to climb the gender mountain.

Just one of the problems was  I was afraid of heights. The higher I climbed the rarer the air became because I had never been in all the situations I encountered. As I entered the world as a trans woman, there were so many situations I never expected to happen. I knew women led multi layered lives but not to the extent I encountered. Initially I thought if I had conquered all the fashion, hair and makeup basics, I had it made in the world. Needless to say, I was wrong. 

Even though my male self contributed to me feeling petrified as I climbed, I kept going. As I decided to leave the male gay venues I was going to and try lesbian and straight bars, I really needed to climb to a new level to survive. When I reached a new level, I paused to look around and see what I had accomplished if anything. What I did accomplish was a degree of acceptance from the venues I went to. Except for one evening when three guys kept playing "Dude Looks Like a Lady" on the jukebox over and over again, I begrudgingly held my spot and became an accepted regular in several places. As I did, my view of the world as a transgender woman became clearer and clearer. My gender dysphoric fog was clearing and increasingly all I could see was a future life living as a woman. 

At the same time, I was still a regular at the diverse mixers in Columbus, Ohio where I met a total range of people from cross dressers to transsexual women who were headed for gender realignment surgery or a sex change as it was known back then. By meeting and learning from all these people, I was able to chart my own path to my transgender precipice. 

The two main things I remember are how desperate I was for information on my gender issues and how scared I was of receiving an answer. Was my therapist right and I could do nothing about my feminine desires? If so, I had reached a precipice in my life and I needed to make a decision which would change my life forever. Of course my spoiler alert is, from my gender view, I could see a wonderful if not difficult future ahead as a trans woman. What happened was, as I built a new circle of women friends who never knew me as my past male self, I kept pushing and pushing myself to the edge of my transgender precipice until I fell down the cliff. 

Unknowingly, for the most part, I had set myself up for a soft gender landing. I gave away the remainder of my male clothes and set out to quit climbing and live a new life. What a relief it was to stop expending all the energy I was using to live two gender lives. The process exhausted me and ruined my fragile mental health. My friends helped me through this difficult time of my life more than I can ever say.

With my fears of gender heights behind me, I met my wife Liz and she helped me seal the deal and live my life as a transgender woman. That was fourteen years ago and we have been happy ever since. I don't think I could have ever envisioned I would meet up and marry another woman in my long life but I did. I guess the fog on my mountain was hiding my future.  

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.  

Teamwork makes the Dreamwork as a Trans Woman

Girls Night Out, I am on the bottom far left.

Similar to so many other cross dressers or novice transgender women I have heard from, they dream of enlisting a cis-woman to aid in their appearance.

I was included in having a similar fantasy. All the way to the point of begging my fiancé to completely dress me as a woman if I rented an out of the way motel room for privacy. Sadly, for me, she agreed and she did do her best to dress me as the woman of my dreams.  I say sadly for two reasons. The first being I did not see that much of an improvement over what I was able to do for myself since by that time I had practiced in the mirror myself for years. The second reason I say sadly came years later when I was facing being drafted into the military and being sent off to Vietnam. At the time she pressed me to tell the draft board I was gay to be deferred from going. Even though I didn't and don't have anything against the gay community, I knew I wasn't gay and wasn't going to lie to escape military service. The end result was she ended up breaking the engagement when I went off to the Army which I learned later was the best thing which could have happened in my life to that point.

As you can tell, I didn't have anyone to enable my teamwork work from any sort of a dream work. One of the problems I was having was working my way through exactly what my gender dream. I was still years away from facing my reality of being a transgender woman. So I suffered alone with my gender dysphoria before I was able to break out of my gender closet. It wasn't until much later when I discovered the beneficial beauty of having cis-woman friends who accepted the new transgender me for who I was. When I let it happen, my dreamwork began to flourish. 

Quickly I began to learn the world from the aspect of being an invited participant in girls' nights out. I was invited along to several different groups of women. All the way from married women to younger girls still in the dating pool. Neither mattered to me because I was learning so much about living a women's life with no men around. Even though when I went out with the younger group, I found how it was to be the decidedly older and less attractive woman in the group. Again, it didn't matter as I flattered and happy to be invited to begin with. 

This was an exciting time of my life when all of a sudden my dream of living a life of a fulltime transgender woman seemed to be so reachable. Being included and  embraced by the women I met was the difference. We went to birthday dinners together, went to parties with each other and of course used the rest room together, All of which turned into the ultimate bonding experience as a new trans woman.

Was I scared? Sure I was but the embraces I received within the group quickly put me at ease so I could enjoy myself and gain confidence in the new feminine person I was creating. It turned out I did not have much creating to do because once my feminine soul hit the world, she flourished. 

Even still, being in a women's world and experiencing their teamwork, did make the dream work happen for me. I was a better person for it once I left my gender dysphoria behind. My mental health improved as well as everything else in my life once I left my male self behind.

Being Afraid to Try

 

Image from Jas Min on UnSplash

Since it took me nearly a half a century to fully leave my dark lonely gender closet, I have to assume there was an extraordinary amount of fear which was holding me back.

As life progressed for me and I became more and more entrenched in a male lifestyle I never really wanted, it was harder and harder to let go. I had a family and spouse who I loved plus a job I was progressing in. So it was not an easy decision to give it all up. 

It all finally came down to what my wife told me after one of our gender based arguments. She told me why didn't I man up and become a woman if I was so enamored with the idea. Had I followed her advice, I would have saved both of us so much turmoil over the years to come. By now, you know the story. I was stubborn and tried to live with one foot in the male gender world while at the same time learning if indeed I could live as a transgender woman. 

Through it all, even since I was taking small steps in my gender journey, the fear of not being able to make it as a full time transgender woman kept creeping back into my life. My scope became so much larger than just admiring myself cross dressed in a mirror to attempting to try the world in costume as a woman during Halloween parties. What kept me going was I felt so natural as my feminine self and then wanted to experience more and more. 

I write extensively about my experiences as a novice transgender woman. Even if I was petrified to try new experiences in the world, I pushed myself to still do them as my age was catching up to me. I wasn't getting any younger and all of a sudden, family and close friends around me began to pass away. Making my mortality even more of a reality than my gender dysphoria. Finally, when I reached the age of sixty and was exploring my life increasingly as a trans woman, it was time to act and put my fears behind me. Realistically, I knew I wasn't going to have a better chance to transition so I better do it. Setting all my fears aside and living in a feminine world turned out to be the best move I could make. I lifted a ton of weight from my shoulders when for the most part, my life restarted again. It was around this time when my new gender affirming hormones (HRT) were starting to change and control my body. Along with developing breasts and softening skin, my whole world softened and I felt emotions I never knew I had.

Now, I am so glad I wasn't afraid to try. My only disappointment is I waited so long to do it. Fear finally turned out to be a powerful motivator for me as it turned potential panicked situations into  successes. Rest rooms were a prime example of success or failure. 

This blog itself is another example. Way back when I was given the idea to write about my new experiences in this world, I didn't even know what a blog even was. Now with well over seven thousand posts and four million hits, it is time to stop and thank all of you for taking your time to stop by Cyrsti's Condo to visit. I have always embraced and enjoyed your participation and all I can say is I am humbled and flattered. 

 

Saving my Own Life

Image from Alysha Rosly 
on UnSplash
 

 
I make no secret of my Bi-Polar mental condition which went undiagnosed for a good part of my younger life. 

Ironically, it was my first gender therapist who connected the dots and determined my condition when I told her I often spent days struggling to even get myself out of bed. I just thought I was riding the waves of gender dysphoria  which kept me so depressed or elevated when I was experiencing brief moments of gender euphoria. During this time of my life, I was far from being the easiest person in the world to live with. At the least, I was prescribed medications which evened out my moods. The meds also helped me sort out my gender issues and finally figure out one mental issue had nothing to do with the other. In fact my gender dysphoria was not a mental issue at all but instead an organic one. Had I listened to my therapist, she was trying to tell me all of that but I was unwilling to listen. Primarily because at the point of my life I was in, I was still a novice transgender woman and didn't know if I could live my dream life.  There were still too many gender bridges to cross such as telling family, friends and bosses I was transgender. 

The furthest I had come at that point was telling approximately five close friends and spouses I was a transvestite. A long way from living as a transsexual with all the resultant rules I would seemingly have to follow Such as major gender operations, moving away and then starting all over again. To make matters worse, I hadn't even thought much about my sexuality. Would I suddenly desire men sexually? I was overwhelmed with all the big questions and just continued my life as a very serious cross dresser. At the least, I was able to work on my presentation as a woman and go from there.

Even though, my solution was far from perfect, I was saving my life the only way I knew how. The problem kept reappearing when I started to go out more and more behind my second wife's back. When I did, I fairly quickly began to build up a robust life as a transgender woman. Every step I took, the more natural I felt when I could never see how I could go back to living a male life. The whole process created tremendous pressure on my already fragile mental  health. I became increasingly self destructive, all the way to an unsuccessful, ill advised suicide attempt. Essentially, from the point of suicide, I purged most of my feminine belongings and even grew a beard to prove to my second wife I could do it. By doing so, I was intensely unhappy for the short time she lived until passing away from a massive heart attack. I often wonder what would have happened with us had she lived.

Following the tragedy in my life, over a short period of time, I regathered myself and refocused  on a new feminine life. I quit dwelling on death and began living a preferred life as a transgender woman. By doing so, I was all of a sudden needing to quickly learn more than I ever imagined about my new life. Throwing out or giving away all my male clothes was at once liberating and  on the other hand, very scary. I had never purged my male self my entire life and he resisted. 

Regardless, scary or not, the process of a gender transition saved my life. Over a space in time, my mental health has stabilized and with the help of gender affirming hormones, for the first time in my life, my body and mind are beginning to mesh. The entire process took me a lifetime to figure out but as I always say, it all was so worth it. 

One Gender Size does Not fit All

Image from Grae Phillips 
on Geraldo television show.

 If the truth be known, all the way back when I was a kid struggling to understand what gender I was on any given day, I would have been known as gender fluid. 

Of course, gender fluid was a term which hadn't been invented yet. Anyone who was interested in cross dressing was branded as being a transvestite and even worse labeled as being mentally ill. In the middle of my gender vacuum, even I knew well enough I was not mentally ill just because I wanted to wear makeup and dresses. I hid my desires and hoped for the best, which mostly came when I was left alone to cross dress and admire myself in the full length hallway mirror at home. Most of all, I was trapped and could do nothing about it. Keep in mind, all of this was happening in the information "dark ages" before the internet and social media. The gender underground I was interested in came mainly from the pages of Transvestia Magazine and Virginia Prince. Even I knew the pages of the "National Enquirer" and other predecessors of Faux News who sensationalized cross dressers were not to be trusted.

Then came the barrage of so called reality television talk shows including, Donahue, Springer and Raphael. All of whom seemed to be pushing the theme of cross dressing husbands Except for the impossibly beautiful and talented "Grae Phillips" who put everyone else to shame. All of these shows probably did little or no good for my gender dysphoria except for publicizing the fact there were cross dressers of transvestites of all kinds at all. All I knew was I desperately tried to watch or tape every show I knew was coming up from my "TV Guide". My wife was trying to tape her soaps and I was trying to tape my talk shows and both kept us busy. Even though I still had to watch my shows in private attempting to learn anything I could about the outside world.

I did learn once again. my gender size was unique and did not fit all. In fact, I still felt out of place when I started to attend my first cross dresser - transvestite mixers here in my native Ohio. I discovered there were so many different levels of participation from transsexuals headed for gender surgeries down to the weekend cross dressing hobbyists.  For some reason, I was not part of either group and once again my gender size was not fitting in. The problem was, all of this happened before the transgender terminology was introduced. When it was and I started to have access to my first computer, I was able to research the term which was unknown to me. Suddenly I knew what had been missing my whole life, a gender size which fit me and I set out to discover more about being transgender. For me, it meant being part of a gender description which was somewhere in-between the spaces I had been in previously.

Even though my gender size did not fit all, finally I was able to locate my own niche to thrive in. Life became fulfilling, scary and exciting at the same time. I found out I was fine being who I was all along and it felt so natural. I was home. 

Transgender Pressure Cooker

Image from Jeshoots.com. 

When someone writes or says something about me being a transgender woman being a choice, I have to laugh. 

I'm sure those of you who have gone through life the way I have with gender issues would agree. Primarily because we have given up so much to cross the gender frontier. Primarily, I am referring to losing family, spouses, employment and gender privileges to transition. Just losing male privileges alone is a major issue. Very quickly I discovered I lost a portion of my intelligence when by accident I became involved in a conversation with several men. I found I was not respected in their world until I finally got tired of being ignored and left the group. Then I began to not speak much until I was spoken to until I began to gain more confidence. 

When I began to be successful, the pressure to be even better as a transgender woman started to increase. For several reasons, my fragile mental health became worse as I started to try to live a life situated between the two main primary genders. In other words, I was stuck in a gender fluid universe I did not want to be in. Living one day as a man and the next as a transgender woman, nearly killed me.  It became so bad I needed to make a conscious effort daily determining what gender I was going to be that day. How was I walking and talking were just a few of the many gender considerations I was going through as the pressure kept increasing. 

All of a sudden, I was able to establish a whole new identity as a trans woman. I was talking to other women and building a small circle of friends which taught me so much about the world I so much wanted to be a part of. I kept going because the process became so natural to me and very soon the main source of pressure came from having to return to what was left of my male life. Even thinking about going back caused me stress and added pressure. 

Finally, I knew I had no way around it and never really had a choice with my life. As a gender therapist told me so many years ago, there ultimately would be no choice for me if I was a transgender woman. Sadly I did not believe her and stubbornly went on to fight a losing gender battle for years before I gave up and faced my gender reality. By doing so, I tried very self destructive measures including suicide and excessive alcohol abuse before I started to live my truth. 

I had no choice and needed to give up all the pressure I felt to transition into a feminine world before it all literally killed me. Thank goodness for all the friends and family I had who helped me through my difficult pressure packed days. The more good days I had with them led to my belief I could live my gender truth full time. Ultimately transitioning was similar to sliding down a hill towards a steep cliff for me. I had others around me who took the pressure off and made the landing a soft one.  

Transgender Ego Revisited

Image from Chloe (I think)

 Recently I received a comment from Amara concerning a post I did in 2011!

Unfortunately she was asking about a dress in a picture I used back then. I didn't know the answer for her. Plus I really don't know where the image came from. Back in those days, I didn't always give credit where credit was due. Which I regret now.

Some other regrets I have now looking back was the ego I needed to deal with when I first came out as a novice cross dresser or transgender woman. I know for certain if I looked back at the overall subjects the blog covered, they were overwhelmingly centered on how I looked. Sadly, I suffered because I was still operating under the impression my male self thought I should look. And, how his ego was effected by how my trans self was treated. 

To make a long story short, her (my) experience wasn't always pleasant and I came home in tears It seemed the mirror was lying to me at every turn. Finally I went back to my cross dressing basics and changed my perspective on going out in the public's eye. As much as I hated to do it, I needed to admit my second wife was right about how I looked. Instead of being the "pretty, pretty princess" as she put it, I needed to learn to tone my look down so I could blend in with other women in the world. 

Ego-wise my outlook changed from emphasizing how my old male self thought I should look in public. Going from worrying what men thought of me, all the way to being able to better interact with the other women I met. Which became very important because the majority of people I met and interacted with were other women. I learned from them women have ego's too, just different from men. A couple times I learned the hard way not to interact too closely with another woman's man or boyfriend and  then needed to treat the claw marks in my back. 

I became a quick learner when it came to dealing with a new transgender world. In my girl's nights outs in learned how the women treated each other with no men around and then how they interacted when men were added in the evening. The change was dramatic. 

As much of a change as my feelings today versus 2011. I can't imagine or put into words all the changes I have gone through. Before I wrap up this post, I did manage to find the dress and image Amara was referring to. Just guessing but I wonder if the person was a candidate in a womanless beauty pageant which used to be prevalent in society and the South before the fervent anti-transgender attacks. Even though I wish I could say I would or could even wear that dress in the photo. it is certainly not me and never was. No matter how hard I tried.

As always, thanks to Amara and all of you who take the time to read and comment to all of my posts. Your input makes my efforts so worth while.   

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.

Be Passionate

Image from Ian Schneider 
on UnSplash

When someone questions why I transitioned genders during my life, the main thing I want them to know my decision was not a choice. It was something I needed to do to save my own life. In that sense, I was selfish.

Perhaps, more importantly, the passion I needed to make it down my extremely bumpy, sometimes dark and gloomy gender path, I found I needed an extraordinary amount of inner fortitude to make it. More than I have ever used before in my life. In fact, I'm fond of pointing out, all I really wanted to be in life was a woman, not a doctor or lawyer. 

From that point forward, I knew I needed to follow a difficult path to achieve my feminine dream. To add insult to injury, I started from point zero with very few so called natural feminine appearances to help my cause. In other words, I had a long way to go to approximate looking like a girl and then later on as a woman. Plus, I needed to endure the onset of puberty and all the unwanted male changes testosterone poisoning was making to me. The whole process took an extra amount of passion to conquer by knowing deep down I was doing the right thing. Every time I suffered any sort of a set back, I needed to somehow pick myself up and get back in the game. Something I fought against doing in my male life. When anything bad happened to me, I knew I could run to my closet for a dress and makeup and everything would be all right. But what if I was already in a dress and makeup when the bad happened, what was next? 

What was next, was the chance to do my life better as a cross dresser or novice transgender woman. Being a novice trans woman was such a change for me over cross dressing, it required a whole new passion and learning curve. So many times, I found myself completely in over my head with no clear way on how I was going to find my way out. Somehow I did and knew I was on the right path. To define it more precisely, when I was a cross dresser, I felt as if my main goal was to look good as a woman and when I perceived myself as transgender I needed to be a woman...move better as one and communicate better in the world.

None of the process was easy for me, some of it still isn't to this day. Changing fifty plus years of striving my best to live as a man was difficult to change. More importantly, when the changes did occur with extended girls' time out with my friends happened, I craved more and more time with them. For the first time in my life, my passion was paying off. I remember vividly a Pride I went to in Columbus, Ohio with Kim, Nikki and Liz when we visited many gay and straight venues. With my tolerance to alcohol, I was having a great time and never wanted the evening to end.

I think now, what my friends may have seen in me was my passion shining through and it may have rubbed off on them. At least I hope so. 

These days, I do my best to lead with a smile when I see the world and hope for the best.

Saving my own Life

 

Image from the 
Jessie Hart Archives

As I began to transition into a transgender life in earnest, the more and more I knew I was saving my own life.

As I mentioned in yesterday's post, all the obstacles I conquered on the gender path I was on just made my entire life more complex. Every time I met a stranger and established myself as a transgender woman to them was a new exciting time but not one which had it's share of fear. After all, I was losing all my well secured male privileges I had worked so hard to have. As a guy, I knew how to react to almost any situation negative or not. As a trans woman, I was in a different world and still had so much to learn. When I was first confronted with losing part of my so called intelligence in a group of men I somehow found myself in, I knew then my life had forever changed. I discovered the men just wanted to ignore me and my thoughts on what they were discussing.

In order to save my life, I needed to adopt what the other women in the world around me were doing. In many ways, they ignored men the same way men ignored women and it became very evident to me why the two main binary genders had a difficult time communicating. I was lucky because after my male upbringing, I had many of the tools to understand what men were really saying. While, at the same time viewing their comments from a woman's viewpoint. Even though the whole concept seems so easy for me to grasp now, back then, I really needed to understand which side of the gender fence I was on since for the longest time I tried to live in both a female and male world.

Soon, I found myself in a gender pressure cooker. On one hand, I had all the male positives to live by which I had learned to expect. On the other hand, the new and exciting (but scary) feminine side of life was increasingly opening gender doors for me. Since I was beginning gender affirming hormones, my world became a softer more sensitive place to be in. The ripping and tearing of my reticence to make a final decision on how I was going to live was slowly but surely destroying me. I was stuck in a gender world never never land which I would not wish upon my worst enemy and I needed to get out and save my own life.

It's no secret what decision I finally made. With the help of several close women friends, I donated all my men's clothes to a thrift store and never looked back. I equate the entire process with jumping off a huge cliff, then having a soft landing in a feminine world. It was difficult, yet it saved my life by making life fun again while at the same time restoring my mental health. 

Saving my own life never felt so good.    

Joining an Inclusive New Club

Girls Night Out Image, I am on the
first row far left.
From the Jessie Hart Archives

 In many ways, this is just an extension of yesterday's post concerning transgender love affairs. 

In the post I mentioned indirectly when I was finally able to play in the girl's sandbox without having to deal with un-due harassment or even scorn. In my post yesterday (and often) I mention how difficult I had it dealing with my second wife dealing at all with me as a novice transgender woman. She was having nothing to do with the process, even though she knew from the beginning of our marriage I was a cross dresser. In no uncertain terms did my wife show my emerging feminine self any encouragement what so ever. She wasn't going to help me join an inclusive new club.

I accepted her ideas on my gender because we both agreed being married to another woman wasn't anything my wife ever signed up for. At that point was when I decided to go it on my own and find out if indeed I could carve out a life in a new gender world. Slowly and very unsurely, I found out I could make it as a member of a new club. Game changers as well as the occasional bouts of gender euphoria helped me along. Examples included the successful Halloween parties I went to. Compliments were easy to come by when people told me how good I looked as a woman. For the longest time, I didn't realize the true extended compliment was how good I looked as a woman, who was really a man. None of it mattered as I made my way along a path to becoming a fulltime transgender woman.

Overall, I am proud of all the work I put into joining a new very exclusive club. To begin with I faced the necessity of learning all the basics of makeup and fashion. Starting from point zero, compared to other girls, catching up was difficult. Especially when I really didn't have much of a feminine body to begin with as well as having a very non-approving male dominated family. More than anything else gender confusion reigned supreme in my life.

What I don't mention enough is the feedback I received later in life from other women when I transitioned. I get the idea from other trans readers I hear from, sometimes acceptance is not so hard to come by but is such a powerful tool when it comes to a transgender transition. We all know, women live a different more layered existence than men and a life which takes no small amount of work to learn. If you do learn the intricacies of what if being offered to you when you are invited to women's only spaces, you will know you have made it into an inclusive new club. Once you are there, chances are, you will never have to go back to an old unwanted male life.   

I will forever remember the  women who helped me along in my journey and opened their worlds to me. Being able to exist on my own in the girls' sandbox or club was something I never thought I could do on my own.

They will never know all they did for me. Even to the point of saving my life. It was the major spark I needed to discover my true sexuality and live as I always dreamed of.