Ditching Good with Better as a Trans Girl

 

Archive Image
from Witches Ball
Tom on Left.

Ditching good with better has always been a difficult obstacle in my life. 

I always blame my parents for my feelings on doing the best I could on anything I tried. Nothing I did was good enough. If I got B's they should have been A's was a prime example. Even though I was an above average student, I don't remember ever being told I was doing a good job. I think now, their influence carried on with me in every facet of my life, including when I was a novice cross dresser and budding transgender woman. 

It all started with my appearance as a girl. When I was younger and before I went through any testosterone poisoning at puberty, it was much easier to look like a girl. But just looking like a girl was never good enough, I wanted to be a girl and enjoy their life. Or at least as I perceived it to be. I guess my parents attitude was rubbing off on me. At the time, all I could really do to further my looks was to over achieve with my meager allowance and take on a rural newspaper route. Between the two, I could sneak out to the store and buy the occasional wardrobe item or makeup I could experiment with. I was doing my best to ditch my good with better as a trans girl during my early age. If I had given the same effort to everything else I tried during that time, at the least I could have received better grades and my parents would have been pleased. 

On the other hand, my parents in no way would have been pleased if they had known I had issues with my gender. I shudder to think what would have happen to me if they had discovered me dressed in my feminine wardrobe and makeup. At the least, I know I would have been sent to a therapist during a time when even being a cross dresser was considered a mental illness. I never wanted to even consider what the worst could be. Perhaps since we were not particularly religious, Christian conversion therapy would not have been in my future. The only thing I know for sure is, I would not have had any understanding at all. All along I did the best I could and was able to hide my cross dressing with the world. How I don't really know.

The older I became, good certainly did not become enough. A prime example would be the Halloween parties I went to when I was first testing the world  I started with just trying to be a sexy sleaze of a woman thinking I would receive some sort of a validation. Several parties later, I grew more bold and wanted to see if I could be mistaken for a real woman, so I wore my business attire and then waited for reactions. Overall I was received well with strangers who did not know me mistaking me for a woman who did not have a chance to dress up for the party. I was discovering better was always best when it came to how I presented as a transgender woman in the world, under the cover of Halloween or not. 

All of my experiences led me to establishing myself in a new feminine world. I needed to try very hard to do away with all my old values to do it. My whole world became a concentration of new friends and life. In my own way, I needed to be better than the world to succeed in chasing my dream of living full time as a transgender woman. Sure I needed to look the part but suddenly I needed to be the part which meant moving and communicating as a woman. 

Ditching good for better in my transgender world was one of the best moves I ever made. By the time I was medically cleared to begin taking gender affirming hormones or HRT, I was more than ready for the results. Almost instantly I knew I made the right decision.  Since my parents have long since passed away, there is no possible way for me to communicate to them they were right. For all the wrong reasons. Their resistance  to giving me any positive feedback early in life made it easier for me to find my own path in the world as a trans woman. A place where good was never enough for me.  

Gender Expectations

Image from the JJ Hart
Archives

As I progressed through my gender transformation, I had so many expectations.

All I really wanted to be when I grew up was a woman but I had no idea of how I was going to achieve my dream. Unlike most of the major professions available to me, there were no schools I could apply to to be femininized. I just wanted to find my passion and follow it. 

To do it, I finally had to be free of the mirror and join the world. Even when I discovered that, I had to often snatch defeat away from the jaws of victory. Or I was defeating myself by going exactly the wrong way with my women's fashion, hair and makeup. At the rate I was going back then, there was no way I was ever going to exceed, or even make it, to my gender expectations.

Another problem I encountered was the complexity of the new life I was trying my hardest to live. Every time I turned one corner it seemed I had another blocking my way. I began to see life as a series of walls I needed to climb. For example, if I couldn't learn to communicate with the world, how could I ever hope to bring my dreams to life. Many times as I journeyed out into the world, I was flying blind not knowing what to expect. The whole process was at once scary yet exciting. It took me many evenings out on my own to establish myself in venues I wanted to be secure in. At the time, I was doing my best to separate myself from the gay bars I was going to where I did not enjoy being treated as a drag queen. 

It was very difficult at first to be accepted as a single transgender woman in the sports bars I was going to. Often I resorted to using my cell-phone as a prop to fend off anyone who thought I was going to be alone for any length of time. It was during this time when I started to meet a trans woman friend of mine and socialize in many venues I was fearful of going into by myself.  There seemed to be an extra amount of security when I was with a friend. When we were together my gender expectations were satisfied because I was allowed to relax and be more social in the world.

From there I transitioned into having my lesbian friends and had a chance to really blossom. All of a sudden, I did not need a man to validate my existence as a woman and they helped me climb another big wall towards achieving my dream. My experiences at lesbian mixers, roller derby matches and even professional football games helped me to come out of my gender shell fast. By doing so, I needed to free my long dormant feminine inner being so she could help me to become a new person. She gladly did so and took off tons of pressure from my gender expectations. If I did not know what to expect, she did and took charge and maybe most importantly gave me the chance to build a quality trans person. I had the rare second chance in life to learn from my mistakes as a cross dresser and a man.

I finally ran the string out and had seen all I needed to see as a transgender woman and couldn't wait for the gender affirming hormones or HRT I was approved to take to take further charge of my body. All my expectations had been exceeded and there was no way I could have dreamed of coming this far in life the first time I slid into hose and a bra when I was a kid. 

I don't completely know why I made it but I sure am happy I did. Along the way, my gender expectations were often confusing to me and impossible to explain to others. Even though internalizing my feelings was brutal, good therapy helped my mental health. Even more so if I had listened to my gender therapist years ago who told me there was nothing either of us could do about my desire to be a woman. Of course I was stubborn and did not listen. If I had, my gender expectations may have really changed for the better much earlier in life.

There is Always a Transition

 

Archive
image
Jessie Hart

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

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

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

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

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

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

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

Transgender Shape-Shifting

 

Image from the Jessie Hart Archives

Changing your unwanted testosterone damaged male body into anything which remotely resembles a female is very challenging. 

In order to be a gender shape-shifter you need to become a perfectionist down to the smallest detail. Plus, seeing as how most of us transgender women got a late start in our transitions, we spent quite a bit of time playing catch up to other genetic women our age. We did not have the peer pressure or Mom's influence to steer our way into the public's eye.

Some would argue also, we trans women had to be better than the average woman to survive. We had to be on point with our makeup, fashion and accessories to look good and in addition were able to still able to blend in with a society of women who increasingly did not seem to care how they looked.

Finding the middle point of presenting well in your cross dressing shape-shifting experience was difficult to say the least. Even so, some of us would consider the process of presenting as a woman as a labor of love. In my case, I was fond of haunting all my local deep discount clothing stores until I located just the right fashion item or accessory. I remember the thrill I felt when I finally summoned the courage I needed to use the changing rooms to see in fact if I had found a "treasure" to add to my wardrobe. 

Then there was the problem of learning how to put my shape-shifted self into motion. No matter how I looked was any good if I still walked like a linebacker and communicated as a man. I remembering working long and hard on discarding my male walk the best I could and picking up the unique movement of a woman. It was difficult for me because I was still working and living a portion of my life as a man and needed to be careful not to cross over the gender line at the wrong time. Even though I secretly loved to be called "ma'am" when I was working as a guy, I still needed to be very careful to maintain my carefully crafted male image. 

I came to the point where shape-shifting became too much for me to handle and I finally tried to be approved for gender affirming hormones to aid the process. I was helped along by the knowledge I had taken my femininization process along as far as I could without the aid of medical help. Since I never was the beneficiary of any natural help with my feminine appearance, I needed all the assistance  I could find. I discovered help when I started HRT under a doctor's supervision. My skin almost immediately began to soften which helped my facial angles soften which also allowed me to use less makeup and look more natural. In addition, my hair growing to the point of not needing to wear a wig anymore, along with growing my own breasts were just the beginning of my advanced search into being a gender shape-shifting human. 

Of course my final test, was how the public was responding to the new transgender woman me. For the most part I received positive feedback by getting no feedback at all. I was able to blend in with the world as my preferred authentic self and take a major step towards being happy in life. All along I was stuck in my dream of wanting to be a woman, or come as close as I could. It was all because I finally discovered my gender was coming from between my ears and not my legs.

Looking back on a shape-shifting life was certainly easier than living it on occasion when I think back on all the failures I went through to arrive where I am today. Supposedly learning from failure is the best way to progress in life and I believe it.

Trans Girl in the Big Easy

 

Mardi Gras woman by 
Jeremy Brady on UnSplash. 

For those of you who may not know the "Big Easy" is a nickname for the city of New Orleans. 

Since I live in far away Ohio, a trip to the Big Easy was and is a special undertaking. During my long life I have been fortunate enough to have been there two times. Once as a cross dresser and once as a transgender woman. Naturally, my visit as a cross dresser came way before my arrival there as a trans woman. 

To go as a cross dresser in many ways required much more work than my second trip. One of the big reasons was I needed to hide the fact I was taking a very small stash of feminine clothes, a wig and makeup from my second wife and I was flying down there. Which meant I had limited space to plan for as far as my luggage was concerned. I am amazed now how I was able to pack and hide my essentials from the prying eyes of my wife but I did.

I was going to New Orleans for a AFTN Network reunion. AFTN stands for the American Forces Thailand Network which I was a broadcaster for when I was in the Army back in 1972. The reunion itself was well attended and once I was there I needed to figure out how I was going to escape my friends, apply my makeup, put on my clothes and discover a venue to go to. I was lucky when my friends decided to call it a night not long after dinner and I was on my own. So shortly, I made my way out of the hotel into the hot and humid Big Easy night. Melting down and saving all my makeup was not making my night life any easier. 

I finally found my salvation in the form of an air conditioned gay venue. In the venue I was able to see several impossibly feminine and beautiful transgender women. So much so, I did not think they were drag queens. As I enjoyed myself immensely and all too soon my time was up, I needed to find my way back through the night to my hotel room where the air conditioner struggled to keep up with the summer temperatures of New Orleans. From there, the next day was made up of memories made in Thailand and it was off to the airport for the return trip to Ohio. 

Similar to the trip down, I was able to hide my extra cross dressing wardrobe from my wife when I unpacked when she was not around. I had a great time at the reunion and even discovered another transgender participant at the festivities. She was very shy and I did my best to open lines of communication with her which naturally I wished I could have as there would be no more reunions.

My second trip to New Orleans was on a bus tour to "Mardi Gras" many years later with my current wife Liz. The extended time we spent on the bus which seemed as if it would go on forever was more than made up for with the party excitement. Our hotel turned out to be a classic restored property within walking distance of the famous Bourbon Street district. Looking back, I would not do it again but on the other hand, since I did it, I would have not to do it again. 

Highlights of the evening we spent at the huge party was when we discovered a food venue we could get into just a block away from the main event and enjoyed a light dinner of appetizers and sandwiches. More importantly, by this time in the evening, we had access to a single stall women's bathroom on the venue patio we were sitting at. Still being restroom shy at the time, I waited for the line to disappear before I went in the tiny space to take care of business. The problem was, I had been in better "Porta Potties" than this restroom. It reeked of sewer gas and I quickly finished, washed up and left. When I opened the door, a line of women had formed and the first woman was glaring at me. I simply smiled and said good luck to her and returned to our nearby table. The only other stop of note we made was to the supposed oldest gay venue in New Orleans. On that night at least, the place was full of male gay "bears" along with a few scattered cross dressers in their mini skirts and heels. 

As the evening wound down, it was time for us to return to our hotel and rest for the evening, knowing it was a great time but not one we would likely be making again. 

Now we are looking at the possibility of going back to the Big Easy during hopefully not during the summer months on our own so we are free to go to the spots we want to go. Finances and health permitting we hope to do it again.

Good Together

 

Image from Columbus, Ohio
from the Archives.

As I grew into expressing my authentic self, I felt the pressure of attempting to placate what was left of my male self while I was increasingly living as a transgender woman. 

Increasingly, I felt as if I was living with a stranger when I tried to express my male self. He was fading quickly into my past, much quicker than I thought possible. Who was this man who controlled my life for so long? It took me so long to have the courage to figure it out. As I always point out, the answer was an easy one. I never was a man cross dressing as a woman, I was a woman cross dressing as a man. Once I figured it out, my life became so much easier. 

Sadly, my male and female sides never were good together. My second wife was fond of teaming up with my male self against my femininized insecure self. When she needed help the most, it was extremely difficult to find. Fortunately, I was stubborn enough to mentally tell them to go to hell. Mainly, because I felt so natural when I was following my transgender instincts. 

Instincts led me to improving my natural presentation as a woman including fashion and make-up arts. Maybe as I improved, my wife and male self became more and more scared. Somehow they saw me glimpse my reality and they did not like the future they saw. Specifically, the very few nights, my wife actually went out to eat with my femininized self, she made it painfully obvious she did not like me. More than anything else, her attitude hurt my feelings since I had attempted to dress down to meet her standards of wearing jeans, boots and sweaters. My next step down for me was to wear no makeup at all which would have defeated the purpose of going at all. Essentially, I gave up on any idea of us co-existing as women of any type. We were never good together. 

All I really wanted was an even break, or so I thought. The more I ended up exploring the world as a novice transgender woman, the more I wanted to do. Eventually, I could take it no longer and took the only way out I had. I went the gender affirming hormone route and decided to pursue a life as a trans woman and the rest of the story is relatively easy. The more life I lived, the more I felt more relaxed and good together with myself. 

Life was good again as I had come full circle from the dark days of death and gender dysphoria. 

Transgender Whirlwind

 

Early Archive 
Image. Jessie Hart

Looking back, there were certain decades of my life which seemed to shoot by faster than others.

When we hit the new century, my life seemed destined to speed up without me even knowing it. First, my Mom passed away, leaving my elderly Dad by himself and before he was diagnosed with dementia. Fortunately, my suddenly smaller family bonded together to take care of Dad. My brother and sister in law took care of all his meds and my wife and I fed him. The situation worked well until the very sad day when he needed to go into assisted living. If you are not familiar with Dementia, it is a very sad and ugly disease which towards the end robs the patient with all of their integrity, making them a child again or worse.

Then I used my inheritance to buy a restaurant which after a good start hit the skids when the town I was in was deeply affected by a severe economic downturn. My whole move was similar to pushing all my chips to the center of the table in a poker game and hoping I would win. Which I didn't. Regardless of all of that, life was dealing me death cards right and left. To begin with, I lost nearly all of my few close friends to cancer then in 2007 I lost my wife of twenty five years to a massive unexpected heart attack. I was in shock and ended up taking the only sure route I could to saving myself, falling back on my feminine self. In her, I took solace and knew I could make it through my dark times. 

The problem I had was, I needed to catch up with my fashion, makeup and everything else it would take me to present in the world as a transgender woman. The best part was I was all by myself and could basically do whatever I needed to achieve my goal. Which was seeing if I could indeed jump the binary gender frontier and see if the grass was greener for me. The more I explored the world, the more I discovered I could indeed carve out a new life, if I wanted to bad enough. 

During this time, which would have been around the year 2010, my life was moving towards being a whirlwind of transgender experiences. I equated it to sliding down a wet hill towards a steep cliff which I had no idea of steep and long it was. What I did not realize at the time, I was losing all of my male privileges and starting to panic. Still I persisted until I learned what female privilege meant to me. Finally I learned being a trans woman meant so much more to me than having doors opened by men. It meant freedom of expression for me. My inner female finally had her chance to live and was taking full advantage of her opportunities. Even still, it seemed every day, I was facing the differences in life I had only dreamed of. All the way to going to male dominated spaces and seeking service which was something I had to do to live the existence I wanted.

Even though life finally did begin to slow down and I became more and more comfortable with my life as a transgender woman, there were still surprises. Since I had survived the gender transition whirlwind, the surprises were easier to overcome. Plus, seeing as how I had survived all the dark years of death I went through in my life, I became more appreciative of the life I was still living. Especially since I was able to transition at the same time.

A Vocal Trans Girl

 

Image from Brooke Cagle
on UnSplash

The other night when we went out to eat, I needed to order what I wanted food wise loud enough to be heard above the noise of a busy restaurant. 

That meant projecting the best I could, my feminine voice to match my appearance. So many times in my past as a transgender woman and or serious cross dresser, I thought I had done a great job with my makeup and fashion only to destroy it all when I opened my mouth to talk. I could see the surprise in the other person's eyes when they discovered something was not quite right with the picture I was presenting. 

For the longest time, I tried to avoid talking to people all together. It seemed to be a good idea until I realized when I refused to talk, I was just coming off as being mean or standoffish...if I was lucky. Or worse yet, I was coming off as a bitch. So to preclude it from happening was I needed to improve my communication skills with the public. Mostly other women, since men had a tendency to leave me alone. At the least, I had only one gender to deal with as I was testing the world as far as my communication skills were tested. Initially, to sooth the panic I felt when I dealt with other women, I attempted to mimic their voices, which worked to an extent until the conversation became too intense. When it did, I was on my own to see if I could be the total package as a transgender woman in the public's eye. 

All was good, or so I thought, until I decided to go farther and farther in my femininization. I started with attempting to look close to the same as far as the wig I wore and the fashion choices I was wearing. No more trashy style as I attempted to blend in and build the woman I wanted to become. The whole process at time became too intense for me as people around me wanted to know more and more about me. Basically, what was I doing in a woman's world? To answer them, I needed to learn to communicate as a whole new person. I needed to put my straight forward often blustery male communication behind me and be more careful on how I chose my language. 

In order to aid in my vocal trans girl process, I even attempted feminine vocal lessons from an expert the Veterans' Administration assigned me. Of course my "coach" and I worked on how I formed my words but also more importantly addressed what I was saying. I learned the words women used more often to communicate what they are trying to say. During the course of my coaching, I had weekly homework I needed to work on diligently so I could do well the next time I went in for my vocal coaching. My goal was to attain all the extra communication knowledge I could from the help and move back into the world and try it all out. It has been difficult for me to judge how effective the vocal program was but I felt every little bit helped in my quest to communicate as a vocal trans girl.

Plus, I would be remiss if I did not mention the biggest gender flip of all, the switch from male active aggression to female passive aggression. The change to me meant, I needed to be more careful in how I chose any words I perceived to be negative when used with another woman. Which also meant, I needed to be on the outlook for hidden meanings when I was addressed by other women. Especially being told I was attractive...for a man dressed as a woman. 

Overall, I think being a vocal trans girl has been the most difficult part of transitioning for me. Since I was always shy, slipping back into being more or less and introvert was easy but not satisfying. I enjoyed the challenge of putting together the final big piece of my gender puzzle which was communication. Once I did, life became much easier when I could stand up again for my gender self. 

All my efforts at the least helped me to show other women who for whatever reason did not view my presence in their world as a negative and they helped me to succeed more than they ever knew. 

A Breath of Fresh Air

Out to eat with my wife Liz on the left.

Even though we are among the millions of other Americans stuck under the infamous "Heat Dome" and temperatures near one hundred, last night I was able to take a breath of wonderful fresh air.

To do it, I needed to get out of the air conditioned house long enough so Liz and I could make the short trip to our favorite Mexican restaurant. Fortunately, the venue's air conditioning was working fairly well and we were seated under a ceiling fan. So we were comfortable even though the place was very busy. 

For the evening out, I chose a lacy pink and black top I have not worn in ages. Along with my dark blue leggings with tennis shoes so I was very much at ease. It was also fun to shave very close and apply a light foundation coat of makeup before I did my eyes and contouring finally finishing up with lipstick before I brushed back my hair. My goal, which I think I achieved, was a soft feminine look. I helped myself by clipping my hair loosely in the back, allowing long straight strands to fall on both sides on my face. The whole effect, served to lengthen and femininize my face.  

At any rate, the most important part was how the public perceived me. Even though I wasn't dressed in the shorts and light dresses the other women were wearing around me, I thought my flowing outfit fit in well. It helped too I was with my wife Liz and her son who has accepted me since he was a teenager. I was set up for success. 

The best part was, no one gave me a second look and I was able to feel as if I was the "normal" woman out into the world. Even little kids ignored me. Along the way, I did have the opportunity to pause in my mind and think back to all the work it took to come to this point of gender acceptance in my life. All the times I was stared at or worse as I tried to make my way in a new uncertain world out of the mirror. In many ways my dreams were answered. All it took were years of struggle to finally achieve the success I found last night. 

After we finished our drinks and dinner, the three of us decided to try a different venue the next time we go out. Which presents another challenge when I present to the world. Plus, I know both my wife Liz and I need to get out of this house and everytime we do, it seems to improve our mental health for any number of reasons. Every time I am "ma'amed" at the table automatically adds to the tip and sends my brain soaring.  I was last night and the tip reflected it without the server (a man) even knowing why.

Perhaps the best point is the resultant gender euphoria I felt after we arrived back home and into the next day. Today I still feel the pleasure of finally arriving more or less where I wanted to be years ago when I was a confused kid. Of course I know there will still be many challenges ahead in my gender journey, I feel satisfied so far with my long term progress. I even call the transgender process, working at my craft. It is the only way I can look at all the gender changes I needed to make to jump across the gender border to see if the grass was indeed greener. For me it was and I decided to never turn back into an unwanted male life. 

Nights such as last night are always a re-enforcement of all the work and effort I put into my transition.  I need all I can get. 

My Wheel had a Flat Spot

Date Night with Liz
from the Archives.

I am fortunate to have lived a long life (so far) as I am looking at my seventy fifth birthday coming up this fall. 

When you live a long life, often you are able to see many things come full circle to fruition. On the other hand, especially when you are leading a transgender life, you discover your circle or wheel may have developed flat spots. You could be moving along in life when all of the sudden flat spots show up to derail you. 

After discovering gender euphoria, at the same time I began to day dream my life away until I could cross dress and admire myself in front of the mirror again. So, no matter how hard I tried, getting back on track in a male life I never really wanted was very difficult. At that point, I held nothing but resentment at the flat spots in my life. Why couldn't I be like everyone else in my small circle of friends. Since being similar to the rest of the crowd, I needed to find away around it. At first, I survived my dark gender closet by cross dressing as often as I could, dreaming I appeared as a pretty girl. The older and more sophisticated I became, the more I needed to put effort into smoothing out my flat spots which could provide me with quite the gender jolt. 

I am not proud of the fact of the amount of sneaking around, all the way to out and out lying I needed to do to try to live a life as a transgender woman which I was finding more and more about. For the most part, I thought I was becoming quite agile at dodging the flat spots which came along in my life when all I wanted to do was run and hide behind my skirts and dresses. Each time, I found I wasn't quite as good as I thought I was when my wife caught me cross dressed again. 

As it turned out, regardless of the hell I put our marriage through, I indeed was in the middle of coming full circle in my quest to lead a feminine life. There were so many times when I was stuck in a flat spot of my wheel, I did not know how I was ever going to get out of it. My lowest point came when I tried a suicide attempt years ago with pills and alcohol. From that low point forward, my life began a slow trajectory forward and upward as I was forced to see who I truly was. Fighting to maintain a male life which wasn't worth it increasingly did not matter anymore as I femininized myself everytime I saw a flat spot coming on. 

I realize having flat spots in life is a human experience we all have to go through but (I'm biased) and think we transgender women and trans men have more than our fair share to deal with. Especially when it comes to having accepting families and friends. Or losing successful jobs and other male privileges. You name it and many of us have had the chance to lose it during the flat spots in our life as we struggle to come full circle. 

The older I became, the closer I came to seeing what a full circle could look like to me. Plus I had the feminization effects of HRT working miracles on my male body. I had been through a lot and was excited to see the work I had put into my flat spots behind me. 

Little did I know, I actually hadn't put all my flat spots behind me after all when I started to look ahead to my end of life options. Needless to point out, I am worried about my future but my goal now is to be positive about anything which may happen.

Trans Girls Dreams

Trans Ohio Archive Image from
the Jessie Hart Archives.

There were plenty of times when I thought living a transgender life was going to be impossible. 

All the days of staring into the mirror cross dressed in women's clothing come back to haunt me. As well as my poor attempts at the makeup arts when I turned out looking like a clown. Who knew being a woman was going to be as difficult as I was making it. But it was and took me years of work to come close to getting it right. 

Dreams of course can come during the night or day. As I was day dreaming my life away about being a girl/woman, I also tragically had the problem of dreaming of being a beautiful girl during my dreams. All my dreams, day or night, did was frustrate me even further. Most of the time, all my dreaming did was trigger my severe gender dysphoria. My cross dresser mirror visits were not doing any good and I couldn't see a way out of my gender issues. All the time shattering any hope I ever had of living life as a transgender woman. 

It turned out I was being a drama queen in many ways and was giving up a dream I really wanted way too early. What happened, all of a sudden I began to learn makeup and fashion skills so at the least I could survive in a world of women. It was a slow process to be sure but if I was ever going to achieve my trans girl dream, I just had to do it. Plus when I survived, I felt so natural and was elated at my progress. Perhaps my ultimate goal could be within reach after all. From then on, I still had a huge amount of work to do. As I delved deeper into the women's world I so admired, I then had to decide if I wanted to go all the way or not. Was the grass really greener on the feminine side? Again and again, I found it was as I tackled issues such as vocal training and just overall life surviving in the world as a trans woman. As I progressed, the light at the end of the tunnel turned out to be sunshine and not the train. 

Since I started my journey with no obvious feminine characteristics, I had a long way to go. I started my path by trying out Halloween parties initially dressed as a trashy woman, all the way to presenting as a professional woman at others. So I could see if I could indeed present as a realistic woman. Finding out I could led me to believe my trans girl dream could indeed be realized. At that point, my life became a blur as I attempted to live as both a man and a woman. All my attempts did was create a tremendous amount of pressure on me and essentially wrecked my mental health. With the help of a good therapist as well as several good friends, I was able to survive and once again re-direct myself towards my dream. Once I felt I was back on the right track, I started gender affirming hormones following an approval from my doctor and there was no looking back for me. 

I never considered I could make it as far as I have when I was the kid staring longingly into our full length hallway mirror at home so many years ago. Even though there were many rough patches along the way as I battled my gender dysphoria, along with waiting until I was in my early sixties to out myself to the world as a transgender woman, I still somehow made it. 

I guess the old saying is true, if you don't dream it, it will never happen. My dream of living a feminine life was the only goal I could think of when I was young and someone asked me what I wanted to be when I grew up. Of course. I could not say a woman and ruin any life as I knew it, so I lied and said a lawyer or something more popular with my parents. I am sure many of you can relate to my story. 

Finally, after more failures than trials my trans girl dreams came through and somewhere within me there is an inner child who is rejoicing. 

Then I Went and Did It!

 

Trans Girl image from
Alexander Grey on 
UnSplash.

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

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

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

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

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

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

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

Owning Who you Are

Image from the Jessie Hart
Archives.

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

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

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

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

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

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

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

Trans Girl Passing Privilege

 

Witches Ball Image. Tom on
left.

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

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

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

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

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

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

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

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

Trans Girl in the World

Downtown Cincinnati archive
image. Ohio River in the
background.

Recently, the day came when my wife Liz and I were able to get out of the house and run a few important errands. Of course it was also a rare chance to see and be seen in the public's eye. 

The first thing which had to happen was to decide what I was going to wear. Since we were not going anywhere fancy, I did not have to over do it. We were just going to the county treasurer's office to pay our taxes and make a possible coffee shop stop, so I felt my leggings and lightweight lacy top would do, along with tennis shoes in case we needed to walk any distance. The treasurer's office was downtown.   

Since we were trying to beat the rush, we decided to try to get an early start, so I needed to be up early (for me) so I could apply a light coat of makeup and brush then tie back my hair which is due for it's summer trim. Once we arrived at the treasurer's office, we were lucky that the set up for the weekend "Taste of Cincinnati" celebration (which draws over a million people) did not interfere with finding a place to park. 

From there it was a matter of going through the guard screening to get into the building. When we did, the guard called us "ladies" so I was happy. Once we arrived at the office we were looking for, the clerks who waited on us were as predictably detached as I thought they would be, so I did not encounter any stares or pushback from anyone. The worst part of course was actually paying our tax bill before we were on our way. 

On the way back home, we decided to just use the drive thru at our favorite coffee shop and spend even more money we didn't really have but we managed to order a light breakfast and coffee and be on our way.

As I often write about, we just don't get out much, so even such a mundane trip was interesting. I often have the chance to relax and reflect on how far I have come as a transgender woman. It wasn't so long ago I would have been petrified to make the short trip I made this morning.

Since we are entering the Memorial Day weekend and I am veteran, I will have my usual post coming up reminding everyone to remember the true meaning of the holiday.

In the meantime, thanks always to all of you who have followed along with all my experiences. Your participation makes it all so worthwhile.

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.

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.

Flashing a Trans Girl

From the Archives. Club Diversity
Columbus, Ohio.

Before you think I am preparing to write a post about me "flashing" another person. No my skirt was not too short or anything else on that occasion. I was wearing my typical fall fashion, boots, jeans and sweater. 

In truth and as boring as it may seem, the only person  who was flashed was me and I don't think anyone else noticed. At least, I hoped not. As it was, my flash occurred just after I increased my dosage of gender affirming hormones. On the evening in question, I was out doing what I normally did, trying to enjoy myself with a drink at one of the venues I regularly went to. 

Suddenly out of the clear blue sky, I felt my face flush and I felt as if I was internally combusting. As I attempted to slyly look at the patrons around me, I was surprised and please to note, no one was rushing towards me with a coat or blanket wanting to put out the flames. Then, as quickly as it came on, my first hot flash as a transgender woman was over and I went back to my drink. I can not say the whole experience was as unpleasant as much as it was unexpected. Up to that point, my gender affirming hormones had ushered me into the second puberty of my life...a feminine one. 

While I could not go back and totally erase all the unwanted benefits of my first puberty which I called testosterone poisoning, my new HRT could help me into a new world. As my breasts and hair grew, my skin softened, along with my facial contours. Not having to wear wigs anymore as well as using less makeup helped my feminization in the public's eye as well as giving me a new found confidence. What I missed the most was having anyone to talk to about my second puberty. When I did bring up the facets of changes I was going through, my female friends just said welcome to their world. Little did they know how long and how much I wanted to be in their world. 

Up to the point of my flash, I had never cried in my life, even during the passing of both of my parents. The best way to describe the new me who could cry was when my testosterone was driven down, the hard edges were taken off my life. All of a sudden, my first good cry occurred one evening when a thunderstorm rolled through my Ohio town and I quietly mourned the loss of my male self. I took no real pity and for the first time, I was able to understand the difference between a good cry and a bad one.

As you can imagine, I was elated with the results of my second puberty in life which did not occur until I was in my sixties. Even though, if I had it all to do over again and transition earlier, I would not have wanted to miss out on the times of accomplishment and fun I had carved out as my old male self. He had taken me a long way in life on a basically successful journey which gave me highlights of having a daughter who supports me to this day, all the way to living with wives/women who helped me unknowingly be a better transgender woman. 

In a nutshell, very few humans have the opportunity to go back and try again. By going through a second puberty and flashing myself, I had the rare chance to not screw it up and be a better person. While I consider my hot flash learning experience as one of the top moments in my life, I also consider the process part of my passage into my unique womanhood. Not unlike having a mammogram. I am just glad, no one else noticed I was on fire one minute and reaching for my coat the second because my thermostat was broken and I was freezing. All part of my second puberty.

See, I told you this post wasn't going to be part of a sensual flash in anyway. Sorry! 

Transgender Reconnections

 

Image from the
Jessie Hart
Archives

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

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

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

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

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

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

Down the Transgender Rabbit Hole

 

Image from Benoit Baumatin on UnSplash.

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

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

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

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

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

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

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

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