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.

It's Complicated

Image from 
Alexander Grey
on UnSplash.

To begin with, I would like to mention a comment I received from "Pammie". In essence she challenged my daughter and son in law's idea of me earning a "Mother's Day" title. Pammie is the mother of four and I completely understand her position. I simply said, I did not seek out the title and I was not bragging. Being bestowed with what I consider the highest honor possible is amazing and I cherish it .Thanks for the comment which brings me to the subject of this post.

Anyway you cut it, being transgender is the ultimate in living a complicated life. It's no wonder many "civilians"  in the world don't understand what a trans person is when we often don't understand it ourselves. I know it took me years to come to a conclusion I was transgender and what it meant. Obviously when I did come to the conclusion I had been avoiding all my life, I needed to explain I was transgender to those closest to me. Destiny seemed to follow me once again (as it so often did) when I was completely accepted by some and totally rejected by others. More precisely, my daughter came out as a fierce ally and on the other hand, an embarrassing rejection from my only sibling, a younger brother. Essentially, he sold me out to appease his right-wing religious in-laws. I knew it was coming, so I moved on and haven't seen him in over a decade.

The problem is each gender's life is considered to be a given to the lucky majority who never question it. To the unlucky minority who for whatever reason we don't often know, we are stuck trying to determine which gender we are. Even to the point of accepting a relatively new term called "gender fluid." If the term had been around during my youth, it would have solved so many issues I went through. All the days I woke up wondering if I was a boy or a girl could be put behind me. 

Then it comes to the basic point of telling other humans of our plight, it becomes very complicated. How do you even attempt to explain your transgender needs to an elderly parent such as I did, or a family worth of offspring who have always viewed you a certain way. A way you carefully crafted all those years to hide your deepest darkest secret. You are not and never were the gender you appeared to be. I know life throws you many unexpected challenges and I am biased but I can't think of anything else which is so complicated to explain. 

Years ago, when my daughter was struggling with her oldest child coming out as transgender to her. One day she said to me how did I know I was trans and then answered her own question by saying I had always known. Which was true, I had always known something was different about me. I just didn't know how to express it. It seemed to be so unfair to me when I needed to address my complicated issues surrounding my gender which my friends did not have to face. 

Over the years and especially when I started blogging, I did expect push back on my transgender ideas but have received relatively few. One of the best comments I can recall when a person called me just another old guy on hormones. I received quite a  chuckle from that. I laughed because once again I had encountered another person who did not understand how complicated our lives are. Most don't understand it is a life time of effort to transition into another gender. For example no one understands in order not to back track on how I perceive myself as a transgender woman, I need to be on gender affirming hormones for life.

Of course I would be remiss if I didn't mention the end of life situations trans people face. I am fortunate to have several transgender allies in my life so I don't have to worry about having my gender questioned at death. One way or another, the entire death process represents the complicated life we face. 

Earning Motherhood

 

Liz on left with me preparing to celebrate
Mother's Day with her son over a Margarita.
Photo by AJ Trumble.

To be clear, I never have asked for the honor of being called "Mother" from either one of my off springs. 

I have a daughter of my own who means the world to me and a step son who I love very much. I met him when I met my wife Liz and was accepted into his world immediately with no questions asked. 

My daughter started the Mother's Day ball rolling last year when I received a small gift and a Happy Mother's Day for the first time from her. Truthfully, I was brought to tears by the thought. I was forever finished with Father's Day. 

I consider the title of Mother to be the ultimate compliment and as I said, not one I take lightly. I also think being referred to as Mother represents a total erasure of all the years of testosterone poisoning and an unwanted male life I went through. It means to me, my immediate family sees me as a full fledged trans woman. I even respected my own Mom enough to use her first name as my middle name when I legally changed it. Even though she never approved of my gender transition. Even to the point of being a relatively harmless cross dresser or transvestite. Back in those days, neither one of us knew the depth of gender issues. I considered Mom to be a product of her generation (WWII/Depression) and moved on after her death. 

Needless to say, most of my gender journey was never easy and represented many roadblocks along the way. I can only say, I never expected to arrive where I am today. Maybe I should come up with another book and call it "From the Mirror to the World...A Transgender Journey." 

We shall see.

Being a Transgender Victim

Image from University of Cincinnati
Trans Seminar.  

It is difficult not to play or be the victim if you are transgender. 

It is always easy to think why me and resort to various escape mechanisms such as in my case, running home and cross dressing in my dress when anything went remotely wrong in my frail male world. Making the varsity football team just wasn't as important as trying to look like a cheerleader in my mirror at home. 

Many years went by before I grew out of being a victim. Perhaps I made my biggest strides in Army basic training when I had no where to run and hide behind my feminine feelings. Ironically, my intense introduction to man hood would in turn enable me to be a better transgender woman in the future. Or as my second wife used to tell me, be man enough to be a woman. For the longest time, I had no answer to what she was telling me. To begin with, I had no idea of how I would support myself as a trans woman and at the same time, I was still very inexperienced as a woman. I had a ton of learning to do. 

As I finally was able to escape the confines of my male existence, I fell back heavily on his new found idea of never being a victim. When I initially was going through all the trials and tribulations of attempting to present convincingly as a woman, many times I was a dismal failure. The easy thing to do would have been to be a victim and blame the world but I chose the other path and kept going back to my cross dressing drawing board and try again. By doing so, slowly I was able to learn what I needed to get by.

By not becoming a victim, I was able to look the world in the eye and learn to communicate one on one with mainly women in public. Very quickly, I was able to see in their eyes what their perception of me was. Mostly I found the majority of women knew I was transgender and were curious what I was doing in their world. By the time I reached that point in our interaction, there was no turning back and I was in so deep I could not back out and hide at home or in my car. Most importantly I learned to stand my ground and learn a new feminine life. Of course there were many new rules I needed to observe and accept before I could move on but I did. The whole process was not without setbacks and many times I needed time to rest before I re-entered the fray cis-women call life. I had learned from my work experience, women have the tendency to form cliques unlike the teams men form, so I knew once I was accepted by a women's clique, I had it made. Just getting there was the issue.

As I widened my search in the venues I frequented, destiny enabled me to be successful. By pure luck, one of the bartenders who always waited on me set me up on a date with her lesbian Mom and we became close friends  and remain so to this day. Then, one night another woman sent me a note down the bar and we became friends also and the three of us were inseparable for years.

Probably, my most chance encounter of all came when my current wife Liz answered my "ad" on a dating site and we have been together for nearly fourteen years now. She came along on-line after having to put up with an incredible amount of trash. For some reason, I refused to become a victim again and kept trying.

Being transgender is a difficult situation to find yourself in. As I always point out, trans is NOT a choice but being a victim is and it is a difficult burden to overcome. 

Transgender Closure?

Image from Nick Bolton
on UnSplash.

 Sometimes it seems as if closure to a transgender woman never comes.

In the very early days in the mirror as I cross dressed, I thought I had reached closure when gender euphoria kicked in when I admired myself. It did until the pressure built to cross dress again and again. Predictably what happened was, I became so frustrated with the process of moving back and forth between the male and female binary genders, I decided to purge (throw away) all of my feminine belongings and go back to a male life. The problem was, deep down I knew purging was not going to solve my transgender issues. Plus very certainly, I was getting no closure and I would always go back to the mirror.

Through it all, I was very naïve and thought closure was around every corner as I continued along my gender path. It turned out, all the small victories I celebrated had nothing to do with winning the war and having any closure at all. The prime example I can recall came when I decided to transition from a cross dresser to a transgender woman. When I was beginning to be successful, I thought I finally had it made when something came along and changed my mind. Foremost among life changing closure experiences occurred when I learned what my second wife warned me about. I really had no idea of what a woman went through in life and I had to learn before I could be accepted. 

I needed to lose my impostor feminine syndrome on several levels. Even though, I couldn't have things such as periods and pregnancies, I had other problems to deal with as a transgender woman to pay my dues. Primarily, losing all my male privileges was what I gave up first to join the world of women. I didn't expect any special privileges to be let in, I just wanted to be given the chance to let my feminine inner soul flourish in the world. She waited nearly a half a century to live and had learned a lot. Even still, I was viewed with a certain amount of mis-trust by several women who I think thought I could run home and go back to my old male life. There was no easy way to prove to them I had given all my male clothes away and there was no turning back for me. 

Once I broke down gender doors thanks to the help of certain close friends, I was able to enjoy more and more activities such girls nights out without impostor syndrome setting in. Finally, I was feeling more and more closure from my old male life. In many ways, I had insulated him from myself altogether. Even more so when I started gender affirming hormones and started to feel the full effects. I started to understand aspects of a woman's life such as emotions all the way to simple things such as the influences such as temperature changes on the body. Suddenly, I discovered women were not just being sissies when they said they were cold all the time except when they were having hot flashes which I went through also. 

As I was going through all the changes in life hormones sent me through, closure set in and I knew there was never going to be any going back. It took me awhile to realize the closure I was attempting represented the most intelligent decision I ever made with my life. I didn't have to worry about any more impostor syndrome because I knew I had paid my dues. 

Now the closure I need to look forward to is doing whatever I can to insure my final years are as smooth as possible. Much of it will be out of my control so I will just have to do the best I can try to pay it forward with organizations such as the "Alzheimer's Organization." My Dad passed from a very ugly case of Dementia years ago, so I hope I won't have to put my loved ones through the same thing. The rest, however is mainly out of my control with no chance at closure. 

Poor Executuion equals a Hot Mess

Image from Author, Columbus, Ohio.

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

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

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

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

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

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

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

Trans Girl Secrets

Image from Ben White 
on Unsplash.

Secrets became a very important part of my life at a very young age.

It all started when I viewed myself in women's clothes  in front of the mirror for the first time. I realized my life would never be the same again. Plus I also knew my desire to be a girl would not be well received by my family at all. It was in the late 1950's and early 1960's when cross dressing was still considered to be a crime where I lived near Dayton, Ohio. In those days any sort of gender dysphoria was thought to be a mental illness. Even then, I couldn't see the act of cross dressing in women's clothes to be an act of mental illness. 

What happened then was I needed to go into a dark secretive closet, I would not come out of completely for a half a century. Along the way, I included very few outsiders in my secret. Four or five to be exact. I did not even include myself in my secret. What I am referring to is the fact I wanted to do much more in my life than just cross dress as a girl, when in reality, the reverse was true. I was a woman cross dressing as a man the entire time and I was indeed transgender after all.

Predictably, one secret leads to another and another and in my case led to lies being told later on. My dishonesty came when I refused to admit to myself who I really was and took out my frustration on those closest to me. I became a very unpleasant person to be around when my gender dysphoria was at its worst. Even to the point of me losing a job because of what I was going through. It was like I was setting myself up for failure at every turn in my life as I waited for more and more people to discover my secret. 

The longer my secret was hidden away and on the other hand, I was desperately trying to discover a new feminine world as a transgender woman, the heavier my secret became. I attempted to hide all my transgender activities from my second wife and was reasonably successful. I say reasonably because I would do more and more as a trans woman until she caught me and the gender battle between us would continue. She was wiser than I was when at one point she told me to just leave her and live a life as a woman. That made her the second woman in my life who I should have listened to when they told me the same thing. The first was my gender therapist years before. 

Sadly, my male self was not ready to give up the strangle hold he had on my life and encouraged me to do the male thing and try to ignore and internalize all my struggles. Of course in the end run, the only thing which happened was the pressure just kept on building as I managed to keep my secret. However, no matter how hard my male self tried to protect his domain, he was slowly sliding down a cliff of no return. Finally, with the help of several close friends I made the gender leap of faith. I gave away all of my male clothes, started gender affirming hormones (HRT) and never looked back. 

Perhaps the best part of not having to protect my secret and not live a lie was my new friends never knew my old male self at all. My inner feminine soul was finally free to live her life. When she did, she became the third woman in my life to tell me the same thing.

The only secret I really ever had was I was never really a man at all. 

A Night at a Concert

Image from the Jessie Hart Archives

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

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

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

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

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

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

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

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

It Has Never Been a Sprint

 

Image from Marcus
Spiske on UnSplash

A transgender life is never a sprint, it is a marathon. 

From the first time we slide on the hose and view ourselves in a mirror, we never believe the gender journey we have started would last as long as it did. Initially for me, I was on a very short term program when I would cross dress as a girl one day and live off the proverbial buzz until I could follow my dream and cross dress again. 

I wonder now if I had known the journey I followed would have so many bumps in the road and would have lasted so long would I have still done it. On the other hand, I was never a sprinter and a marathon was a closer match to my personality. Plus, there were milestones along the way which kept me going. Very early on, I knew I needed much more than just the feel of women's clothes to propel me forward. There just had to be more than just looking like a girl, I wanted to do more and be a girl. I knew the journey would be difficult and maybe impossible but I needed to keep trying. 

First of all, I needed to learn the basics of feminine appearance so I could safely explore the world as my new exciting self. With no help and very little money, I haunted the thrift stores trying different wardrobe items which were very inexpensive until I finally began to see improvement. My sprint during the time in my life when I was experimenting more and more was exhausting. The one thing which was evident to me was I was on my own. To win or lose was my passion but first I needed to see away around surviving a stint in the military where I could not express my feminine self. Fortunately, I could fall back on what my male self had taught me about internalizing my feelings. During my three years of military service, I managed to survive without cross dressing except for one notable Halloween party which led to me coming out to a few friends of mine as a transvestite. Included in the group of three was a woman who was to become my first wife and the mother of my only child. This brief sprint set the stage for me coming out to others in the future. 

For awhile, I was over confident about others accepting my authentic self until a conversation with my Mom brought me back down to earth. She soundly rejected me and I was off I pursuing my gender marathon again. Even with the set back, I had plenty of energy to move forward. Move forward I did, regardless of living with an unapproving wife. I needed to hide nearly all of what I was doing as I ran my next sprint. 

By this time, my sprints were becoming more defined as  I was increasingly discovering my dream of living a fulltime life as a transgender woman just could be a reality. Next up on my sprint were gender affirming hormones and making the decision to never look back where I had come from as a male and plan ahead a life as a transgender woman. 

The only constant I found on my gender marathon was change. Every time I thought I had it made in the process, something came along to disrupt my thinking. It could be as minor as being mis-gendered in the world or so much more now as I reach the twi-light of my life. Now making it to the finish line of my gender marathon in the best shape possible is my main goal.