Come Out Swinging

 

Image from Chase Li
on UnSplash.

Often, I write about running home to dress in my skirts and put makeup on to hide the failures I was feeling as a male.

My plan worked well until I discovered I was advancing so far and so quickly as a novice cross dresser or young transgender girl, I was unknowingly destroying my hiding place. Someone turned the light on in my closet and suddenly I had nowhere to go. I needed to come up with a plan to come out swinging or I was doomed. In addition, I still had to be very careful not to be caught and end up in a psychiatrist’s office declaring me mentally ill. Then I would really have nowhere to hide.

The better I became at the art of makeup and dressing myself, the more I needed to consider what I was doing and wondering if I should come out swinging at all. The problem continued to be, I was building more male privileges in the life I was living. My life was like shadow boxing myself as I sought out answers. Like most of you, I was risking a lot as I came closer to pushing all my life’s chips to the center of table and betting it all on the fact I was a transgender woman all along.

Then I went into my highly recommended experimentation years of my life. In order to have any sort of an idea if I wanted to live as a transgender woman, I needed to walk a mile in my new high heeled shoes. Those were the scary yet exciting nights when I escaped the gay venues I was going to and began to attempt to establish myself as a regular in lesbian and other straight venues I was used to going to as a man. When I did, I discovered I needed to make another transition from serious cross dresser to transgender woman exploring the world. To my amazement I was successful when I went to venues such as TGI Fridays and socialized with other professional women. Maybe I did not have to swing so hard after all to escape the dark confines of my gender closet.

To be sure, I still had setbacks when I came out into such a different world, but I had enough gender euphoria to realize I could live out my dream if I worked hard enough at it. At first, I suffered from the “what I thought a feminine life would be” syndrome. I was trying to put all those years of closely watching how women lived into actual practice without paying my dues in the world. While I resented the fact, no one would let me see behind the cisgender woman gender curtain, I was becoming a victim which did me no good in the short or long term. So what if I did not understand what I was doing wrong, I just had to figure it out and do better.

One of my major problems was solved when I finally came to the conclusion I was never going to be accepted as a cisgender woman, but I could find my own version of womanhood on my own path. That is when I started to wear only one wig, settled on one name and began to build a new serious life as a transfeminine person in the world. As I settled into a new life, I found that many people (especially women) appreciated my honesty in a world of fake people. I was surprised at all the female attention I received and was relieved I did not have to attempt to change my sexuality.

The more I changed, it seemed the more I stayed the same as my long hidden feminine soul took control finally. I was dealing with life on a one-to-one basis for a change without having to swing away all the time just to survive. As HRT hormones entered my life, it was just another example to me of what took me so long. My body took to the gender affirming hormones flawlessly and I was off to yet another transfeminine adventure. My age and hormonal status led me down a new road of dealing with confrontations, no more could I try to macho my way through trouble, I needed to take the feminine path and try not to get into a situation I could not get out of before it happened. Or no more swinging away for me. I needed to use my brain for a change.

As I have pointed out in previous posts, I was never a good athlete and could never hit a curveball when I tried to play baseball. I finally took it all to heart and quit trying to hit a curveball altogether and settled into watching the boys play baseball (and girls too) when I did not have to play. I was tired of banging my head against a hard gender wall and ended up where I always should have been as a transgender woman. I just wish I had not been so stubborn when I was doing it and had shed my male self-long before I did.

 

In Over my Head

Image from Alexander Mass
on UnSplash

In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  

The Blues

 

I have not been ashamed over the years to document my struggles with depression, which was finally diagnosed as being Bi-Polar by a gender therapist I was going to years ago. Fortunately, the therapist was the first of several who did not try to connect the dots between my mental health issues and my depression. Saying one caused the other.

What was happening was, when I got the blues, I was down for days, not wanting to even get out of bed. Having said that, I was able to break the depression on occasion by cross dressing and going out into the world as a novice transgender woman. Breaking the hold of the blues was often very brief when I needed to return to the very mundane male world I was stuck in.

In addition, I was doing very little to help myself. I drank heavily, not considering how much of a depressant alcohol was and my favorite music to listen to was the blues. Regardless of my gender issues. As you can tell, outside of the Bi-Polar medications I was taking, I was doing very little to help myself. With or without the help I received, I managed to make it and eventually thrive rather than just survive. Regardless of my second wife calling me the “pretty, pretty princess”, I still took a lot of pride in my feminine presentation. The better I looked, the fewer blues I needed to conquer in my life because for once, I was doing something positive for myself.

When I needed the Veteran’s Administration’s health care in the worst way, they really came through for me. I was going through hard times when my restaurant closed financially and could not afford my medications when one of my employees suggested turning to the VA for help. It was about this time too when the VA approved gender affirming hormones for veterans so I could help myself on two fronts by making an appointment. It turned out that what I needed was an appointment with a therapist for both of my issues. My depression and my gender issues. By the pure luck of the draw, I was assigned to a therapist who had knowledge of my depression and my gender dysphoria. I was going into my first visit thinking I would have a difficult time explaining how my Bi-Polar depression had nothing to do with my gender outlook.

I never had to connect those imaginary dots with my new therapist. She had a good understanding of the needs of the LGBTQ community and what it meant to me. Once again, all the paranoia I had built up was wasted and my depression meds as well as my HRT meds were approved. It was the help I needed when I needed it at the lowest part of my life.

Regardless of all the good news I discovered, I still had to translate all of it into my real life which was changing dramatically. I was going out more and more testing out my interactions with the public. Building a new life was as difficult as I had imagined and the struggles I went through sent me back into the blues when I thought I would never make it as a transgender woman. To be completely feminized by no one else but me turned out to be a daunting task because I was starting from near to point zero. Very quickly, I quit being a victim and turned the tables on my male self who was fighting for survival, but not before I tried various self-destructive things such as trying to kill myself. The blues were literally trying to kill me.

In my limited understanding of both issues, I fought for my entire life, both depression and gender dysphoria could be caused by chemical imbalances in my brain. So, I had no real chance to battle them. I was born to a high-risk birth rate mother in the days when the medication DES was routinely prescribed. DES supposedly flooded the uterus with estrogen hormones which could have affected my future gender issues. Of course, now I will never know if my lifetime of struggle to fit in with males was doomed to begin with and now depression is widely believed to be caused by a chemical imbalance in my brain which I think I inherited it from my mom. One way or another, I feel fortunate to live in an era when medications are available to treat my depression.

In many ways too, the blues are an outlet I miss in my interactions with today’s world. As the mid term elections rapidly approach, I am preparing myself for the barrage of anti-transgender propaganda from the Republican party here in Ohio. Knowing what to expect won’t make it easier for me to survive. As always, I will just have to. With or without the blues because every little thing is going to be alright.

 

 

Confidence is your Main Accessory

 

Image from 
Jon Tyson on UnSplash.

Some assume I have reached the point of life I am at, through very few challenges.

The truth is that I faced many challenges along my very long gender journey to living fulltime as a transgender woman. I write about many of them often. As I look back, the one main challenge I faced was having the confidence to move forward to my strong dream. Perhaps the earliest confidence I needed was when I walked down our long driveway dressed as a girl to check the mail. Hoping someone would notice the girl in a miniskirt out of the house on a winter’s day without a coat. Then hoping no one would see me and somehow report me to my parents. Nothing ever happened, so I gained the confidence to keep doing it.

The problem was, there were only so many trips to the mailbox I could take to feel good about my cross-dressed feminine self. Here I was taking all that time and effort to feminize myself and having no outlet except the mirror. I was frustrated in my little closet which I had no idea of how to escape from. I was like a caged animal, I knew I wanted out of the cage, I just didn’t know where to go when I escaped.

As the years passed by, I traded going to the mailbox with a yearly trip to a Halloween party. Even though it took me years to get it right, I finally figured out how to figure out a “costume” which helped me to build my confidence that I could present well enough to get by in the world as a woman. My goal always became to be mistaken for a woman in a costume, not as a man dressed as a woman and I achieved it. From there, my problem became Halloween only happened once a year, and what would I do the rest of the year about my growing gender dysphoria. My final decision was a simple one, if I had the ability to do it. I would have to manufacture my own reasons to sample the world as a novice transgender woman and see if I had the same positive feedback I received on Halloween. I discovered most of the world did not care about how I was dressed, and I gained the confidence to do more.

I made it to the point where I began my “bucket list” of things to do as a transfeminine person. Or could I do other things that women do in their everyday lives and succeed. Every time I did something such as taking myself out to lunch, or negotiating a bookstore and buying a coffee, I checked them off my bucket list and proceeded to move on to more difficult interactions with the public.

Of course, not everything I did was a success. I was told to leave a venue I thought I was a regular in one night when three drunk guys thought it would be fun to play “Dude Looks Like a Lady” on the jukebox over and over again. Initially it hurt me, until I got my confidence back and found another venue right up the street. My success was complete when the crew of the place I was asked to leave found me one night. They told me the manager who told me to leave was fired for drug abuse and they wanted me back. Retribution was mine as well as a real boost to my confidence. It felt good to be wanted as their token transgender woman.

Even so, to this day, I wonder why my confidence is so fragile. In September, my wife Liz and I are taking another bus tour. It’s our fourth one, and this time we are traveling from Ohio to Boston and then up into New England by train. Even though, I have never had any real problems with anyone else on the trip before, in the back of my head I still worry about some right-wing woman questioning my gender and ruining my trip. I am sure I am just paranoid and should be worried about catching Covid again and ending up in another hospital. Which is how our last vacation ended up. Hopefully I can get an updated vaccine just before we go. Which will build that part of my confidence.

The only way I know to build your confidence is to keep being yourself and improving your presentation as a transgender woman or cross dresser if you prefer. Perhaps it will always be fragile like mine is and it is something we always will have to deal with. One thing is for sure; you cannot build it by hiding yourself away. Expect some setbacks and keep moving forward as you are building a new future. It is a huge step forward. Having nice fashion and applying beautiful makeup is wonderful but it all means nothing if you do not have the confidence to pull the picture together. Humans are like sharks and they will know something is wrong if you let them.

 

 

In Over my Head

 

Image from Wilhelm Gunkle
on UnSplash.

As I thumbed through my new feminine workbook, I sadly discovered there were no chapters on what to do if I got in over my head. In my well-built male world, I had been able to figure out strategies on what to do in times of duress. I could choose to stand and fight, try to bluster my way through, or just run from the problem.  None of which was available to me anymore on the gender path I was on.

Even though I was blessed with a healthy male body which was slightly bigger than the norm, I had hated the changes testosterone made to it when I had no choice but to go through male puberty. Very quickly, I grew past the sizes of my mom’s clothes I was trying on and had to find other ways to build my wardrobe on the very limited budget I was on. My newspaper route money, along with the small allowance I got for helping around the house, just didn’t go far. Still, I was able to sneak out of our rural home under the pretense of visiting my grandma who lived downtown and do some shopping for makeup and hosiery. I just remember how incredibly overwhelming the makeup selection was and how much I was over my head with my selections.

After I was able to smuggle my purchases past grandma and my family, then I needed to work earnestly on how to apply the makeup I bought and not look like a clown. After looking in the family mirror and feeling like a clown in drag, I knew I was in over my head and just had to find a way out, or in as it turned out. I wanted out of the male world and into a feminine world. The mirror was wearing off, and I needed to improve my presentation, or I was doomed to forever occupy a male spot in the world where I knew I was not in over my head. The white male privileges I was building up were just too easy to not take advantage of. Ironically, all the good I was accomplishing in the world with my family, friends and job was frustrating me because, deep down, I did not want it.

What was happening was my frail mental health was being destroyed by all the gender ripping and tearing I was going through. One day I was a successful man and the next I was working to present my self as a woman was very destructive to my everyday existence because the whole process took me back to my gender fluid days when I was a kid. Back in those days, no one knew about the gender fluid term, or used it which put me in over my head before I even really started in life. Remember, I grew up in the pre-internet dark ages when anyone who cross dressed was considered mentally ill. At least I knew, even though I might be alone as a transvestite (another term from the dark ages), I was not mentally ill.

I barely survived the dark ages when I did learn there were actually individuals like me who wanted to dress as women. I would be remiss if I did not mention Virginia Prince and her Transvestia publication at this point. It was my lifeline to the cross-dressing world and opened my closet for the first time. When the light came flooding in, at first, I was blinded, and it was difficult to find my bearings. My first transvestite-crossdresser mixers I went to left me more confused than ever before. I knew I was in over my head when I saw and occasionally chatter with a few of the ultra-feminine women who I could see no masculine traits at all and on the other hand, I knew I was innately more feminine than many of the cross dressers I met. So, I left with more questions than answers.

I was caught in the same place for years as I explored the world looking for myself. Surely, along the way, I found myself in over my head as I transitioned but I kept going anyhow. Too stubborn to quit and waste the new feminine privileges I was working so hard to gain. To use another example, I threw myself into the deep end of the gender pond before I had learned how to swim. I gave myself no choice but to make it. Fortunately, all the mirror time working on my presentation as I wanted to be like the beautiful cross dressers I saw in Transvestia came back to help me. If I could present myself to blend in with the world, it gave me one step up to make it as a transfeminine person.

I certainly was in over my head enough to earn my right to play in the girl’s sandbox, and fill out my gender workbook.

 

Transgender-When Life Throws you a Curve.

 

Image from Chu CHU on UnSplash.

It’s baseball season as we head down to the “dogdays of summer” around here in Cincinnati. As I have mentioned many times, the gender gods allowed me to take my passion for sports with me when I transitioned from male to female. This year, I have been completely emotionally immersed in the Cincinnati Reds professional baseball team. So much so, sometimes I feel guilty about my involvement.

Overall, though, life threw me a real curveball when it came to sports. For several reasons, athletics helped me to keep the bullies away, since I was doing “boy” things. As I played, I found I could not hit well at all, primarily a curveball and resorted to running home to my dresses and makeup to feel better about my failures. And I did, which solidified my deepening idea I should have been a girl all along. Dressing in my pretty feminine clothes certainly felt better than crying in the shower after I committed a key error or struck out to end the game.

As time went on, I faced the reality of non-athletes everywhere, life had thrown me a curve ball I just couldn’t hit. Somehow, I just needed to adjust and become the fan I am today and quit being a victim. I think perhaps it was my Army duty which took any idea of self-pity away from me. So what if my draft number was twenty-three, I would just have to enlist for three years to make the best of it. Plus, the entire routine of basic infantry training took any idea of being a victim away from me. At least I was not one of the guys crying on the night bus to Ft. Knox in the middle of a Kentucky winter. Somehow, I would have to make the best of a situation I did not want to be in.

It turned out, that idea carried right over into my gender dysphoria. The older and more experienced I became as a transgender woman, ended up clashing with my increasingly successful male life. Life had thrown me a gender curveball, and it was not fair but the problem was mine to deal with.

Initially, I kept striking out on my path to transgender womanhood. I was woefully unprepared for the world I so desperately wanted to enter. The path was quite dark with many bumps and curves, so I needed to be careful with the high heeled steps I was taking. Perhaps the most important problem I faced was when I was completely outed as a man in a dress was quickly going home and attempting to figure out what I was doing wrong. Was it my fashion, or my makeup, or what?

This time I refused to be fooled by a gender curveball and hung in there until my life began to change for the better. Slowly, I was being accepted as my true transfeminine self in the public’s eye. I was not hitting any home runs yet, but I was making contact with the public and was successful.

Incredibly to me, the more contact I was making, the more I needed to make. In particular, women were curious what I was doing in their world and drew me into conversations which were uneasy for me in the beginning. Life was throwing me curveball after curveball, and I became halfway decent at making contact with the strangers I met. I think too that after the public met me, more than a few of them reacted to the fact that I was a person who was living with their truth. Then I needed to catch up and respect myself for living my truth. Which was difficult for me to do for years.

Ironically, at that point, I went to work for a company which would not accept any of their successful managers being victims. I carried their training over into my real life and was better prepared for any and all setbacks I encountered. I began to see my supposed setback in life just could be a positive if I made it one. Not so much different than when I went to Army basic training wondering how I was going to make it without my cross-dressing crutches.

After immersing myself in the world of cisgender women, I came out as a better person. Certainly, well rounded in how the two main binary genders interact with each other. I could not ever make it as any sort of an athlete, but it turned out I could as a transgender woman. A journey I came to respect many times along the way.

 

The Only Constant is Change

 

Image from Brad Starkey
on UnSplash

In life it seems, the only constant is change. Especially for transgender women and transgender men. As with most of you, my life of change started quite early when I started exploring my mom’s foundation drawer. To make matters worse, I then started raiding her makeup collection.

As I viewed myself in the hallway full length mirror, little did I know what a long trip I would embark on to battle my gender dysphoria. My male self was strong and put up quite the battle when all along my feminine self was plotting how she could win the war. All he could do was resort to typical male actions and reactions such as internalization of the gender problems all the way to completely running from them.

Change became reality when I started running from my problems by changing jobs and moving my family several times. My first move took my wife and I from our native southwestern Ohio home to the radically different environment of the New York City metro area. I was naïve and thought moving to a more liberal area of the country would provide me the opportunity to pursue my growing serious cross dressing “hobby.” Nothing of the sort really happened except a couple of times. The first of which was when I made the journey out to Long Island to attend a cross dresser – transgender mixer. I was so successful that I was carded at the door to prove I actually was a man.

The other example was a Halloween party I was invited to by a fellow manager of the restaurant I managed. Somehow that night I managed to escape the criticism of my second wife who wasn’t going with me anyhow and dress the way I wanted to. I chose my favorite wig, short dress and heels and slipped out of the house. Away from the unapproving prying eyes of our landlord. The evening turned into my dream scenario when I found I was going with several other tall and sexually dressed women as I was. The ultimate camouflage was I fit right in. My successes fueled my ego and pushed along my changes. For the first time in my life, I began to believe I could achieve my ultimate dream of living as a transgender woman. If I was fooling the world on these evenings, why couldn’t I do it more.

In the short term, my male ego hurt my ability to change. Being briefly accepted as a woman only pushed me on for more change. Leading to huge fights between my main feminine gatekeeper (my second wife) and myself. In typical male fashion, he oversimplified the gender problems with the same old results. It was time to run again and move from NYC back to a different part of Ohio. This time, to a very rural area along the Ohio River. Surprisingly, change came easily to me in this rural area of Ohio. I was able to cross dress and do the grocery shopping as well as other trips.

Still, change haunted me and I felt the need to find a job in Columbus, Ohio where I had been successful in the past in the crossdresser-transgender community. I felt if I could go back there, I could again fit right back in.

This move or change ultimately led me back to my hometown which was close to Columbus. I had come full circle with my changes which led me to finally face my gender reality. I was and had always been a woman at heart and had made my own way down difficult paths to find her. Plus, I was so tired of running all the time, so I did not have to accept the only constant being change. The only constant was my whole life as a male was a lie, and I had to do something about it.

I ended up taking advantage of all that I learned the years I was a novice transgender woman and using the lessons to make my transition more flawless. For once, I was changing in place as I threw my mirror out the window. I started using the public as a mirror to see how well I was presenting as a transfeminine person and went on to live my life.

For me, the final straw which ended my ill-fated male life was when I changed my life for good and started HRT or gender affirming hormones. I could not believe all the changes I went through and how good they felt. I know all people go thru changes in their lives but not to the extent most transgender persons do. It is certainly a difficult journey and not recommended that you take the path I took.

You Make a Terrible Woman

 

JJ Hart on left. New wife Liz on right.

As I was initially coming out of my intensely lonely and dark gender shell, I dealt with quite a bit of guilt. Especially when my wife called me a terrible woman. I initially thought she was referring to my looks, which she told me she wasn’t.

My second wife was also fond of telling me coming out was all about me which as I look back on it, she was right. My transition was all about me, and I was completely immersed in it. Every time she even made the slightest move to interact with me, I shunned her as I was scared, she was just going to be negative. To be successful, I needed to do it alone it seemed.

I am sure the progress my wife saw in my overall presentation made her feel insecure about the future of our marriage. No matter how guilty I felt about the journey I was taking without her, deep down I knew I had to stay on my path if I was ever going to have a chance to achieve my dream of living as a transgender woman. Which my wife was dead set against.

As I progressed on and on the guilt grew, I was having. Here I was jeopardizing a good marriage, family and job just to wear women’s clothes and makeup. My problem was, I was still refusing to accept the truth about myself. In other words, my desire to be a woman in any sense of the word ran much deeper than just looking like one. When my wife told me I made a terrible woman because I hadn’t paid my dues past looking like one, I knew somehow, I needed to set out to learn what she was talking about, regardless of the guilt involved. To survive, my transition had to be just about me, and I stubbornly pushed forward.

The problem was, the more guilt I felt, the worse my mental health became. I did not know who to listen to, the world at large or the person I was closest to. The world at large was slowly coming to accept me as a transfeminine person while my wife was as standoffish as always about my progress. What she did not know was I was making the strides needed to prove I was not a terrible woman and in reality, a fairly likeable one. Or at least I was trying to.

Time marched on, and my guilt increased to the point where I committed suicide or tried to. When I failed, the entire self-harming episode left me with further problems with my guilt and mental health, so I sought out therapy. Fortunately, I found a good therapist who understood depression and the transgender community, and my life began to improve again. My therapist told me it was alright to feel guilt about the gender transition process and sometimes you must leave loved ones behind so you can live. Beyond all of that, she taught me extreme gender dysphoria was difficult to deal with and before long, our in-person meetings at the Veteran’s Administration were between her and my authentic self. What a relief!

My guilt subsided as my joy increased in my life. Sure, I still had rough spots to contend with, but with my overall knowledge of the world and what to expect, I knew I had finally overcome my fear of actually “making” a terrible woman. In reality what happened was I had the chance to live my way through what my wife told me and in addition. I was not making anything. I already was a transgender woman and had always been. I was just guilty of trying to hide it and internalize it too long. Surely, it was all my fault, and I never had the chance to apologize to her because of her untimely death from a massive heart attack at the age of fifty. I wanted to show her I had paid my dues in the world, and, at the least, I hoped we could be friends. Actions speak louder than words and I know she would never back off from saying I made a terrible woman and in turn at least like the new me.

In life, we rarely have a chance to make a second impression, and it has been nearly an impossible one for me since most of the people I knew as a man (that mattered) had passed away. I needed to concentrate on the new acquaintances I met as a trans woman who never knew my old male self who in his own way had passed on also. Since I did not have a difficult time making and keeping friends in my new life, I must not have been a terrible woman after all.

Out in the Testosterone World

Hair by JJ Hart, Beret hand beaded
by "Liz T Designs" 

Just a short post today as I just returned from braving a testosterone heavy environment. More precisely, it was time to get the oil changed in our car, which was slightly overdue. By the time I was done, I wished I had a dime for every tattoo I saw on the completely male staff.

For some reason, any trip to a male dominated (such as auto workplace) has always caused my gender dysphoria to flare up. Even after all these years that I have been out as a transgender woman, I still feel the same trepidation. Which makes me feel even more frustrated with myself.

This morning, as I pulled the car into the next available bay to be serviced, I cannot be sure, but I think the manager called me the dreaded “Sir”. But, as the work progressed, he became increasingly nice to me. I never know if it is the result of age privilege but at least he never called me “Sir” again. Very soon I was on my way to my next stop which was the coffee drive thru for wake-up drinks for my wife Liz and I encountered yet another young man at the drive thru window who was at least honest with me. I asked him how he was doing, and he said he was looking for a cot to lay down on to take a nap. I just looked at him and before I could say anything, he quickly said what I was thinking. He was working in a coffee shop, stop and get a cup to wake up.

One way or another, we made small talk, and I was again on my way, this time back home and he had acted as if nothing was wrong with how I was presenting as a transgender woman.

At least, the short trip out this morning into a potentially difficult world built my confidence up that I could do it again when my wife Liz and I go on an extended vacation to New England in approximately a month. A vacation which will challenge me in many ways including restroom privileges.

The end result of this morning was, I need more public adventures into potentially difficult situations to enable me to build the all important confidence I used to have when I was spending more time in the world.

  

Deadly Serious

 

Image from Nicholas COMTE
on UnSplash

Looking back at my long (50 year) gender journey, I wonder now how I became so deadly serious as I considered myself more than a casual cross dresser.

I came a long way from just experimenting with my mom’s clothing to where I am today. As I live fulltime as a transgender woman. Many days, if I have the time to even think about it, I wonder how I went about connecting my dots during my travel from the male to female gender. But, before I go any farther, I should mention two things. First of all, I have nothing against cross dressers, as I spent too many years being one to attempt to put myself up on any sort of gender pedestal. Secondly, I don’t consider myself a female in the strictest sense of the word. That is why you might notice I use the transgender or transfeminine word more frequently. In addition, I strongly feel the woman word (and man) are both socialized terms as many females or males never make it to being true women or men. Now, since I got all of that out of the way, what does that have to do with being deadly serious about anything. Not much, but I always like to clear the air.

In my life, I can only remember being deadly serious about two things, the first was following an often-vague path to my own version of womanhood and the other was Army basic training. In the Army, your secondary MOS or job classification is infantry which means I received the same training as everyone else who were going to Vietnam for a very uncertain future. So, the bottom line was, I took my military training deadly seriously. Just in case I needed it later. Fortunately, I never did. Naturally, pursuing my feminine path was destined to be just the opposite.

It seemed, the more I tried to do as a novice cross dresser or transgender woman, the more I wanted to do. I forced myself away from the easy gender experiences I was trying, into a true interaction with the world and my challenges became much more serious but not quite to the deadly stage. I think the reason was, I was still experimenting with people as strangers. Not like somebody I would see more than once. I was naïve and thought people would not remember me for what I was, a man in drag or a dress. When other people began to see me repeatedly it was good for both of us because I needed to up my presentation game and quit changing wigs every time I went out. To succeed in the new world I was creating, people needed to see I was deadly serious about being accepted in the new mainstream venues I was going to when I gave up on going to the gay venues I tried.

More importantly, I lived through all the bumps and bruises I suffered as I silently fought back against the gender bigots I faced. Some of which were not so silent as I attempted to enter the so-called women only spaces such as restrooms. One night, I was called a pervert by an irate cisgender woman before I backed her down. She was the one I had to threaten with LGBTQ sanctions on her business if she did not leave me alone. Which she did.

The more comfortable I became in my transgender world, the more deadly serious I became about doing more. Soon I was to the point where I was like a runaway train heading down a one-way track as my manhood was coming to an end. One of the final acts of severing what was left of him came when I was approved for and started gender affirming hormones or HRT. My body took to the new hormones flawlessly to the point when I wondered why I hadn’t been on them all along.

The reason was relatively simple, as the changes from the HRT would preclude me from going back to the male life I had worked so hard to establish. Would I be deadly serious enough to risk all I had built up such as a long-term marriage, a family and friends plus a very good job which I could have never transitioned on.

Finally, after years of introspection, I made the decision to go as far as I could without surgery into a transgender life. With all I had to lose at the age of sixty, I decided “playtime” was over, and it was time to be deadly serious again and never look back as I had reached my dream of living in a transfeminine world.

 

Buckle Up!

 

Alpha Gatekeeper Hope
Who Let Me In!

If you are a transgender woman or trans man and you have been transitioning along your gender path for any length of time, you know there are plenty of highs and lows to prepare for.

I know on my gender journey; I have had to buckle up for many rough roads ahead. I have many examples I write about often such as being told to leave one venue I started to go to when I decided to leave the gay bars behind and go to mainstream straight venues. I went home in tears like when I was laughed out of malls by groups of teenaged girls when I first attempted to go out in public. For a long time, I never thought I had a chance of living my transgender dreams at all.

Deep down, something told me to fasten my seat belt and keep trying to succeed. You see, the problem was all along in my life, if something went wrong, I ran to my skirts and put on makeup to make it go away. In these cases, I had nowhere to run, so I had to get it right. I was in a corner, and I couldn't get out without a lot of work. It turned out to me, the whole process was a labor of love, and I felt good going forward on my gender path. The problem was I was still quite naïve about what I was facing and thought success could be found if I just was able to present properly as a woman. To try the new world out I was in, I went to all sorts of different situations. Examples were when I went to a downtown festival and an outdoor concert just to see if I could. Following painstakingly applying my makeup and choosing just the right clothes, I managed to be successful at both, and my confidence soared.

When I did, my frail confidence was shattered again when I learned the world was curious about me as a transfeminine person. It meant I would have to really buckle up and do more than trying just to look like a woman, I needed to communicate like a woman. All of that turned out to be harder than it sounds (no pun intended). I found out quickly that women operate on a different wavelength than men. Men use a more simplified straight forward approach to communicating with each other and other women. On the other hand, I discovered I better refine my listening skills, plus be aware women communicate with each other on non-verbal wavelengths. Also, eye contact with other women became very important too, if I was ever going to be allowed to play in the girl’s sandbox by the alpha female gatekeepers.

As with anything else, I needed to allow practice to become perfect if I was ever going to succeed at reaching my goal of living as a transgender woman. To do it, I needed to forget my unreachable dream of being able to present so well as a woman that anyone would ever think I was cisgender. To begin with, testosterone poisoning had taken all of that idea away from me. I needed to re-buckle up my expectations and know the best I could do was follow my path as a woman from a different background. To succeed, I needed invitations from cis-gender women to their girls’ nights out so I could observe and learn how other women acted when men were not around. Naturally, I needed to put what was left of my male ego behind me when I had to buckle up and attend several of these meetups. My primary example came one night when I was invited along with a group of servers where I went to, to another upscale venue to party. They were all young and attractive and immediately were surrounded by attentive males, leaving me by myself and my drink. I learned a powerful lesson that night why certain attractive women tend to hang out together.

I was fortunate as I traveled my gender journey, I had key alpha females to help me with my seatbelt. As an example, I have added the picture of “Hope” who ironically gave me hope for my future dreams. She was the first bartender I ever met who went out of her way to be kind to me, all the way to introducing me to her lesbian mother who I stay in touch with to this day. Hope led the way for me to be accepted by others and thrive in the girls’ sandbox, and I will never forget her for it.

My main message is, no matter how many bumps and bruises you may suffer along your own gender journey, just try to securely fasten your seatbelt and make the trip as interesting as possible. Just remember, not many are able to make the same journey and achieve their dreams of living as a transgender woman.

 

 

 

Low Risk...High Reward?

 

Image from Jayson 
Hinrichsen on UnSplash.

There are many things we do in the gender universe which represent a low risk, high reward effort.

For example, under the cross-dresser umbrella, we have the far-ranging participants who go from wearing panties under their male clothes, all the way to those who fully dress as transfeminine women in their spare time. At the least, there is more risk to the cross dresser who is fully dressing in feminine fashion and makeup than the person who simply needs to pull his pants up to cover his panties. At some point too, one must consider if wearing women’s clothes is simply a fetish or is there more to it. Which carries even further into the world of sissies and such which involves men who fantasize about forced femininization.

In my case, even though I deeply felt the pleasure of hose on my shaved legs, or other beginning thrills such as looking at myself in the mirror, deep down I knew there was so much more to what I was doing about my developing gender issues. I knew too, if I was ever caught with my clothes and makeup on, there would be no rewards, just risks, so I needed to be very careful. All the way to the point of never wearing panties under my male pants at school and on rare occasions dreaming about a woman forcing me to cross dress at all. Ironically, I talked a woman into dressing me head to toe as a woman only one time and I ended up thinking I could have done it better myself. The risk of telling her did not equal any reward at all.

The risks and rewards proportionally grew greater together as I grew older and my male life began to grow. Many times, without my feminine one who was still stuck in her mirror. It was in the Army of all places, when I first came out to a small group of friends that I was a transvestite and much more than the fully cross-dressed woman they were able to see at a Halloween party. Naturally, it was a huge risk to take because the Army could have taken measures to discharge me. The reward did come when I was able to finally feel the relief of telling someone else my deepest secret and no one cared.

The further reward of coming out of gender shell was the fact my first wife was in the group of friends I came out to. Our marriage then led to the greatest reward of my life…the birth of my daughter who supports me to this day.

As my male world kept expanding and threatened to take over my transfeminine experience, I was going through a wonderful period of great discoveries in my life. Those were the days when I first discovered the transgender term and what it meant to me. For the first time in my life, I found a community which I belonged in. I was too much woman for the average low risk cross dresser and too little for the risk it all world of the transsexuals who were headed for gender realignment surgery.

I was so comfortable in my new place in the world, I was prepared to take bigger and bigger risks. Much to the chagrin of my second wife who had no problem with my cross dressing but was totally against any thoughts of starting gender affirming hormones and living increasingly as a woman. Every time I went out to explore the new feminine world I was creating, I was risking my twenty-five-year marriage. Because I chose to lie to myself for many years of denying who I really was, I ended up making us both miserable.

My excuse was I knew I would be losing a great marriage, a substantial job and many hard-earned male privileges if I threw all my cards into the middle of the table and came out into the world as the person I was always meant to be. Finally, the choice ceased to be mine as I embraced my new feminine self. My wife had passed away, I reached the point where I could retire from my job, and I was eager to check out the world of female privilege. It was all a huge risk, but I had to take it as I was nearing the age of sixty and I figured I was near a now or never moment in my life.

I had never been a gambler of any sort, but I wished I had the courage to make the move I made earlier. One thing is for certain; you can never rewind your life to make up for past mistakes. You just have to do the best that you can of your past to plan ahead for the future risks you will have to take.

 

 

No Easy Way Out.

 

Image from Peter Fogden
on UnSplash.

When I had grown used to escaping my male problems by dressing in front of the mirror in my small stash of girl’s clothes and makeup the best I could, then I forgot my problems. It was an effective way to find a way out.

Before I knew it, I was digging myself a hole I would have a difficult time getting out of. As always, my main problems came from my refusal to accept my gender issues. I would cycle through the same old issues such as cross dressing until I relieved all the pressure I was under as my male self. Then knowing the relief would only last a couple of days.

Occasionally, I thought I would find the way out of my gender shell by trying the infamous “purge” which would finally do away with my feminine self altogether. Of course, we all know purging was no escape either as in a very short time, my urge to cross dress would flood back in again. All of this resulted in depression I struggled to control.  Years flew by before I was diagnosed as being bi-polar by a gender therapist I was going to. The diagnosis helped me to understand why I would sometimes want to do nothing but stay in bed. Fortunately, I was able to find a medication to help me that I was able to tolerate, and to this day, my depression is under control. Plus, having my bi-polar under control allowed me to separate it from my gender issues.

It became extremely important when I was matched up with a therapist from the Veteran’s Administration who controlled my gender affirming hormones. One thing I did not need was a therapist who connected my dots wrong and left me no escape. What I mean is, if I was matched with a therapist who thought my depression and gender issues were connected in any way. As with other things I excessively worried about, the therapist I ended up being matched up with never connected my dots wrong, and my HRT and depression medications were always kept separate.

Escape finally came slowly when I began to take control of my own life. I went down a huge rabbit hole I had been ignoring. As I left my old gender closet and explored the rabbit hole as a whole new person, I discovered the world I had only dreamed of as I began to live as a transgender woman. I also found many new layers of a feminine life I knew nothing about. I went from creating a fictional trans woman to a real person as I explored the world. The real person I became had to be able to communicate with the world at large. As with any other worlds I ever discovered (such as the military) being a transgender woman came with a whole new set of rules I could not escape.  

As my confidence increased, so did my success in building a new life. I so badly did not want to escape at any costs, I risked all my male life such as family, friends, and employment to live as a transfeminine person. I was putting on the line such as the benefits of hard-earned male privileges, a long-term marriage and a good job. All to follow my feminine dreams. It turned out, I learned many lessons when I was attempting to escape the rabbit hole I was making for myself.

Some would say it took a lot of courage to do what I did. While others would think I was nothing but a fool. I would say neither is the case because in order to live in this world at all, I knew I would have to make changes to escape. By the time I needed to make the final transition decision, I was nearly sixty and it had been weighing heavily on my shoulders for years. By then, I took all my so called “practice” time and became a transgender woman on a mission.

I escaped all excuses and rabbit holes I explored on my way to living my dream. Becoming my true self in a woman’s world was incredibly difficult to do. Just when I thought I was conquering the road I was on was being successful, I learned I was only just beginning and there were many obstacles to come. I was lucky enough to be able to negotiate everything by having wives to women friends to help me on the way.

If I had given up the fight and given in to the true desires I was having, I would have never had to think I had no way out.

 

Hormones in my Life

 

Image from Mitch
on UnSplash.

This morning, as I changed out my Estradiol hormonal patches, I briefly paused to consider the magical changes HRT has meant for me.

My thoughts were formed yesterday when I wrote a short chapter in my book I was writing on my life that my daughter bought for me. As I remember, the question of the week for me was how I responded to changes to my body over my life. I started by writing about how bad I felt when my body began to form angles when I went through male puberty. It was long ago, but I still remember my disappointment. This was way before the time of puberty blockers for young transgender boys and girls. Not that my parents would have approved of blockers for me anyhow.

I followed up my ideas on male puberty with what had happened to me since I was fortunate enough to be approved for gender affirming hormones and I could experience a second puberty in my life, this time, one I wanted. Even though I was attempting to overcome all the damage testosterone did to my body, I could not fix most of it. I was stuck with broad shoulders and a big male torso which served me well to keep bullies away but did little to help me to present well as a transgender woman.

On the positive side, the new HRT meds were able to soften the harsh angles of my face and soften my skin, so I could use less makeup. I also found I had no male pattern baldness, so my hair grew so well one of the first things my daughter did was treat me to a hair styling and color at her upscale women’s beauty salon. Another case of being totally out of my old male environment and loving it. After my fear went away. At that point, I was loving my new life.

My new life as a transfeminine woman took on a new meaning as I adjusted to my new body. Gone were the old days of blustering my way through life with my male body. In were the days of being more in tune what was my body telling me from newly sensitive breasts to a developing transgender woman’s’ intuition, I was really changing. By intuition, I mean I needed to develop a sense of anyone who was going to potentially threaten me with any harm. Much of the new development was not much of a problem because I was going through so many other internal changes anyhow. The easiest way to explain it is, my world went from the harsh realities of being male, all the way to the softening universe of being a woman.

Also gone were the days of me attempting to macho my way through any situation. From being able to admit when I was cold, all the way to planning ahead to any potentially dangerous situations, it all presented me with a new world to consider. All because of two little Estradiol patches I applied twice a week. It was magic to me how well and how fast they worked. It was as if my body was waiting for the HRT meds my entire life.

It is not often that I have the opportunity to slow down my everyday life and consider the benefits of being approved for gender affirming hormones. I needed to go to a physician back in those days which were relatively difficult to find. On one hand I had seen the health problems other transgender women had gone through when they went the route of unsupervised hormones. Since I was near the age of sixty at the time, I did not want to risk any health issues and fortunately, there weren’t any. Even though I do not remember the exact year I started HRT, I remember I took my first dosage which were pills with my future wife Liz on New Year's Eve. From there, I progressed to higher dosages and eventually to the patches I am on today.

Which brings me full circle to the meaning of this post. With or without the hormonal medication I am on, I would still identify as transgender. HRT just helped my external presentation in the public’s eye. And, if you are considering hormones, you don’t need them to be you either. If you do, make sure you seek out a doctor to help you to know all is well before you make the jump.

For me, the HRT process was the final point of knowing I was doing the right thing by jumping off the gender cliff I was on. It sure made the landing softer.