It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Gender Shape Shifter

 

Witches Ball Halloween
Image,

For years I obsessed with  the idea I basically was  just a shape shifter between my male and female selves. 

All of this coincided with the time I spent as a very serious cross dresser. Basically, all if my idle thoughts were grounded in my feminine appearance. Time I wished I could get back. As my feminized presentation became better, the more I felt more than just a shape shifter. Especially when I began to explore the world as a transgender woman.

My gender ideas were changing primarily because I quit thinking I was fooling the world and began to know I was living as my authentic self. So if the other person was a transphobe and did not like me, it was their problem, not mine. My mind had made a difficult yet important shift when I began to believe in myself. 

At the same time, ironically, my shape shifting became easier. I became more comfortable in the world and at the same time more confident. I found confidence to be my main feminine accessory. Much more so than my favorite jewelry, heels or wigs. Looking another in the eye was much more important when I used the women's room and other places I needed to communicate. Without confidence, I might as well just stayed home and watched television with my miserable male self. I was not shape shifting any longer, I was me.

When I did, I found I was so much happier and I wanted to push the feminine envelope I was living farther and farther. It was all good, until all of my actions put me on a collision course with my second wife who never approved of any ideas of me transitioning any more into a transgender world. I had put myself firmly between the rock and the hard place when it came to my gender issues. To attempt to survive, I did the best I could to live out my dual life I was living. I would over achieve in my work world as a man, then at the same time try to explore the world as a woman.

The more in-depth I became living a dual life as an accomplished shape shifter, the more pressure I felt to do something about it. In the meantime, I was doing things such as shopping for my wife's Christmas gifts as a woman. When I was successful, I was encouraged to do more and more as I suddenly began to feel secure in the world. 

Finally, I came to the point when I cross dressed as a man, I felt foreign as if I was shape shifting again and wanted no part of it. Happily, by that time I was able to try gender affirming hormones which femininized me even further. I enjoyed the effects so much, it was an easy decision for me to never go back to my male world. Being free of gender shape shifting was quite the enlightening experience. 

Transgender Guilt

Image from Civil War Cemetery
Cincinnati, Ohio.

 For many years I felt guilty about having my gender issues.

After all, I felt so alone in my desire to leave my male self behind and live in a feminine world. Not only was I alone, I even was scorned when I tried to express my desires. As I grew through the stages of being a weekend cross dresser into a novice transgender woman, I waited for the guilt to go away or at the least diminish. It never did. In fact, my guilt increased. 

Factors arose such as what would I tell my daughter and my wife, all the way to how I would manage to support myself and my family when it seemed I could lose everything if I transitioned. Selling my life out to be a woman seemed at times to be such a selfish idea and I felt guilty. So much guilt, it stressed me out so badly it wrecked my already fragile mental health. I would not have wished my gender problems on my worst enemy and even a bigger problem I had was there were few people I could even talk to about it. 

Sure, I had a therapist, but even then I felt guilty of sacrificing my masculinity and talking about my inner feelings. I had a gender storm inside me I could not get out and I was stuck between a cruel rock and a hard place. The reason was I was trying to live in both of the main binary gender worlds. For three days, I was learning if I could exist in a feminine world and in the next three days I had to go back to my boring male world. On the extra day, sometimes I lived in both genders, at least in my head. Of course doing all of this did nothing to relieve the guilt I felt on how I was living my life.

The more I lived my life between the genders, the more I could see what was coming. I was lying to myself when I tried to tell myself my inner woman was winning the contest for my soul. When I was spending my three days experiencing life as a trans woman, I felt more alive and excited about my future than even before. At the same time, I still felt the doubt creeping in about if I could make it at all. Perhaps freedom from guilt was on the horizon if I could just make it. So, I kept trying different things to enhance my future.

As I always point out, my male self pulled out all the stops and threw in guilt as one of the main weapons to keep the status quo he always fought for. As he fought, he made sure he brought up all of the fond memories of the time we spent together. 

Finally, his efforts proved to be to no avail as I started to put together a new life as a transgender woman. It turned out he could not compete with my truth, I had always been destined to be feminine. It was an unfair fight, guilt or no guilt. I could take the battle no longer and gave in before the stress literally killed me. I will forever remember the night when I gave in to my feminine side and decided to research if I was healthy enough at the age of sixty to undergo gender affirming hormone therapy. Which would signal a point to me which I could never to back to life as a man. 

From that point forward, I was able to give the remainder of my male clothes away along with the guilt they carried with them. I moved forward to legally changing my name and all the identification documents which could be be legally done in my state and with the Veteran's Administration. I was doing my best to put all the transgender guilt as far as I could into my rear view mirror. 

Why Me?

Image from Emily Morter on UnSplash.

I can't remember how many times in my life I have thought of the idea of why me? Why did I have to have all these gender issues.

It wasn't until much later in life did I learn it was OK to be different and in fact sometimes I preferred not being part of what was called "normal." Then I learned nearly everyone had their skeletons in the closet and many people just were able to make the skeletons dance better and faster. These days, we often see many public figures whose skeletons ran out of gas and are exposed. For some reason, I even feel sorry for some of them because they needed to hide their so called problems for so long. Mainly because I suffered so many years in my own gender closet.

Plus, as I negotiated the complex path I followed to living my ultimate dream of living life as a woman, there were still many times I questioned all I was doing. On one hand, my job choice was proving to be successful while on the other hand, my self destructive self was trying to destroy it all. I was having huge why me moments. In other words, I was being a complete victim. Over the span of my life, I ran and hid behind my skirts and dresses anytime I encountered any rough patches in my male life. I always figured I never wanted to be a part of the male world anyhow, so it worked well for me to hide. 

In time, the pressures in my life increased and finally I needed to stop thinking why me and face them head on. The major issue I needed to face (and did not) was rather or not I was much more than a causal weekend cross dresser and in fact a novice transgender woman. At that point, I decided to find out if I was indeed a trans woman. It was then, I began to explore the world in any way I could to see if my gender skeletons could still dance with the best of them. At the same time I was dancing, my why me began to fade away. I had no more time to wonder why I had gender issues when so many seemingly did not. I found their closets were just deeper and different from mine. 

Then, I started to embrace my transgender status as a positive. Very few humans ever have the opportunity to explore and live in both binary genders, male and female. All of a sudden, when I was out in the world, I could see and understand all the games the genders played around me. I even knew I was succeeding when virtual strangers I met would ask me questions concerning their spouses or boy friends as if I would know. Which often I did. I just hope they took my advice as free advice and took it with a grain of salt. 

As you can tell, probably being a victim was a bigger issue for me earlier in my life versus the why me question I was always falling back on. The process took all the courage I could muster to overcome my problems. Ironically, hiding behind my skirts and dresses became the focal point of my new found confidence in the world. When I was able to dress to blend in the world as any other woman, my skeletons cheered me on. Since I had always been a terrible dancer, I never danced in the world but just kept it in mentally. 

One way or another, why me was becoming why not? It was time for me to take the gender issues I was born with and run with them. No more wondering what my life would have been like if I was born into a world the men around me faced. I was similar to a big piece of clay which was just waiting to be worked into a new unique human. Why not?

Better Together

Outreach Image from Trans Wellness Fair

Slowly but surely I came to understand I was battling  the two binary genders in my life. Of course the main problem was I was born male into a very male dominated family. My inner feminine soul faced an uphill battle from the very beginning.

The older I became, the bigger the gender split or dysphoria grew within me. The problem became, I did not understand what was happening. All I knew was I cherished my very limited time I had alone so I could explore my feminine self. Back then, all I really knew was I had very separate personalities. Deep down, I didn't know why but some days I could live a male existence. Then on other days, all I wanted to be was a girl or woman.. It was during those days, in many ways my male self became emotionally abusive to myself.  He couldn't come to any sort of acceptance to what was going on.  I suppose these days, I would be described as being gender fluid. 

Through it all, life went on until I began to accept the fact I was gender dysphoric and needed somehow to deal with it.  Initially, my he decided to go down the typical male route of trying to ignore a problem hoping it would go away.  Of course the problem never did go away until I faced it. Also initially, I tried to explain away my love of everything feminine by thinking I was a cross dresser and/or I was just a guy with a different hobby. The entire thought process bought me a little more time but that was it. Deep down I knew I was much more than a cross dresser but I was afraid to accept it .

Fear of transitioning into a transgender world without the aid of any surgeries ruled my life. I tried my best to explore the world as my feminine self which took up most of my spare time. Anything I still did as a guy, I wondered if I could do as a transgender woman. This included the most macho events I was doing such as sporting events, after all, there were more women there, why couldn't I be there also? 

Slowly but surely I came to the point of appreciate the fact I was able to experience both sides of the gender border. I came to the understanding of why women and men don't understand each other on many levels. Basic communication between women became a priority for me. Very quickly, I picked up on the fact women use non verbal communication between each other and employ major uses of passive aggressive behavior rather than the direct approach men use. Many times, it took a good amount of time for the claw marks on my back to go away. 

Learning the basic differences of gender turned out to be very beneficial for me. In addition, I learned how I could still use some of the hard earned male knowledge I brought with me. Initially I lived with the idea, I wanted or could have anything to do with my old male self who was so unwanted. However, not everything thing I did in my life was a waste of time. Even though I was bringing a ton of baggage with me into my male to female gender transition, I still needed to take the time I needed to to live a more beneficial life as a trans woman.

As I was able to actually finally transition and when I did, I was better together when I was able to utilize both of my my male and female selves but it was a huge battle to get there. He won a few battles but she won the war.

Sexuality .The Great Divide

Image from Jack Lucas Smith
on UnSplash

 It is no big secret men are more insecure in their sexuality than women. Many to the point of being toxic in their approach. I think the toxicity is the reason for the uptick in violence against all women, transgender or not. 

When I transitioned out of my old unwanted male world into a new scary exciting feminine universe, I wondered if my sexuality would or have to change. For me, it meant giving up on my long held belief I was NOT a gay male. God forbid if I wasn't . Somehow I never the connection of dressing up as a girl with wanting to be with a man sexually. Even to the point when I finally understood I wanted to do more than just look like a woman, I wanted to be one. To be honest, the sexuality scared me more than anything else about my MtF gender transition. Could I have been wrong my entire life about my attraction to women? 

Very early in my transition I was "coached" by friends such as Amy on how to practice being with a man by using a banana. While I appreciated the advice, I never really decided to think about a banana the same way again. Plus, since I was living a whole new lifestyle, who was to say I needed to live it a certain way. After all, there were many lesbians I knew who would disagree with me or anyone about  needing a man to validate their existence. Since so many had told me I shouldn't or couldn't change my gender, what was one more idea to shatter. 

Still, I wasn't sure on how to proceed when I decided to leave the fragile world of men who were secretly struggling with their own sexuality and build a new one for myself. It meant entering a time of experimentation for myself. First I searched high and low on dating sites for a man who happened to live close by and wanted to try to date me. To put it mildly, I failed miserably when I was completely upfront about being transgender. Almost all of them saw me as only a fetish sexual object. They wanted to skip the dating aspect of meeting me in a public venue and go straight to a motel room. When I refused, most all of them would have nothing to do with me.

On the other hand I discovered women did not feel the same way about me. Curiosity I believe led most of the women I met to find out more about me when I went out to many different venues. It all made my life fun and exciting again. Of all people, I found many accepting lesbians who I could socialize with. As I always say, they taught me so much about being a woman who could stand on her own. Once again, my sexuality became secure again without having to make any drastic changes.  No bananas for me except to add to my ice cream sundaes. When I was with my close knit group of lesbian friends, I could watch the fragile world of men from afar as I relied on my  previous experience as a guy to let me in on what they were feeling. Which was probably the biggest reason men didn't trust me. I knew too much. 

By living a transgender lifestyle, I was able to observe the sexuality of both of the primary binary genders. I came away knowing I made the right decision. Destiny led me the right direction. I obviously nothing against the male gay community but it just wasn't for me. I was correct in believing women were the most secure gender when it came to accepting any variations in their sexuality and men are the most fragile.

Men are From Where?

 As we attempt to cross the gender border from one side to the other, we certainly suffer from a lack of much training at all.  We had no understanding of which planet we trans folk came from to begin with. 

Partially because most of us didn't have the benefit of having an understanding mother or sister who participated in our progression into the feminine world. We never were able to indulge in girls only sleepovers where clothes, makeup and other girls activities were discussed and acted upon. Thus, when we actually began to have the chance to live in the world we always dreamed of, we had no idea of how to do it. The only ideas we had were from the outside looking in. 

The whole void we stepped into all of a sudden left us (as novice transgender or cross dresser persons) in a spot which was difficult to conquer. Many of us, including me, went through my feminine teen years which I never experienced in the public's eye. When I did stuff my overweight male body into tight female clothes designed for teen agers, many times I was laughed at when I attempted to go out in public. I found out the hard way my mirror only told me what I wanted to see and the mirror only reflected what my old male self thought was appropriate to present well in public. I was very stubborn in my approach so it took me awhile to realize to survive as a transgender woman in the world, I needed to be able to communicate with all other women. As I did it, I keenly felt the problem I had having no previous training growing up as a girl. Naturally, all the time and effort I put into surviving in a male world were a waste of time.

Perhaps, the biggest hurdle I faced when I transitioned from male to female came when I tried to communicate with other women. Quickly I learned the value of non verbal communication. Which is one of the reasons men and women sometimes misunderstand each other. Ironically, it was much later in my transition when I was finally was invited behind the gender curtain to truly experience how women communicate. I was warned by my wife one time when we had a fight, she told me I made a terrible woman and it had nothing to do with just appearing as one. So I set out to learn what she meant.

It took awhile but lessons were learned. An example was when I knew I had arrived as a trans woman when I was approached by a man in a venue. Instead of looking at him, I looked at the bartender (woman) who was looking back at me in essence to leave the guy alone. It was the first of many communication lessons I learned when it came for me to communicate with other women.

Other painful lessons came when I was involved with other women who I thought accepted me. They smiled and were overall nice to me until when I turned around and they had their claws in my back. Learning the new world of passive aggressiveness would prove to be difficult for me to adjust to. Of course I was used to the more forward aggression men deal with when engaging each other. I had no training in any of this public interaction as a transgender woman so I had so much to learn. 

Perhaps you remember the book "Men are from Mars-Women are from Venus". In my gender explorations I found the book to be true on many levels. Starting with and including communication. As a trans woman, I brought a totally different outlook to the binary gender standoff. I was flattered when women friends of mine asked me to explain what their men were thinking. 

At that point I wondered if the binary genders had a planet, why didn't we transgender people because we occupy such an unique position. Many ancient societies used to recognize us as special. We need to find our way back there again. We just have to be trained to do it. 

Owning It.

 

Image from the Jessie Hart
Archives

Long ago I learned the hard way the power of owning my public appearance as a novice transgender woman or very serious cross dresser. 

I was tied too closely to my mirror and didn't realize until it was too late how it could lie to me. Examples included how the mirror told me I was an attractive woman who could go anywhere just to be bounced almost immediately by the public. Many times I would come home in tears wondering where I went wrong. Finally I came to the conclusion I was putting my feminine priorities in the wrong place. In reality my mirror was not in my house but was in the public's eyes. When I learned to dress to blend in with the other women around me, I began to own my existence as a transgender woman. No longer did I have to worry as much about being laughed at in public. 

Also, when I owned my life as a trans woman, I gained the all-important confidence I needed to follow and improve my right to exist in the world. If someone had a problem with me, it became their problem, not mine. The biggest pressure I faced was needing to communicate with the world as my transgender self. Suddenly the process went way past how I sounded into what I was saying. Owning the new gender world I was in meant learning to operate on an entire new spectrum involving an internal look at how the two main binary genders (male and female) communicated. Quickly I learned why men and women couldn't connect on the basics of communication. I learned also both genders put up a sort of invisible barriers when it came to talking to each other. Ironically, I began to be asked by each gender why their spouses or partners didn't understand them. 

I truly didn't find out why I had a key insight into both genders until I was allowed by other women into their world of life and communication. I learned the power of non-verbal communication as well as the seismic power shift between the genders. Basically the process is very simple. Men deal with power systems such as money and athletics when women deal with a more passive aggressive world. I was fortunate in that I was aware of how women formed smaller cliques (not teams like men did) and reacted passively aggressively to those with power. Such as management. When I was in my male management days, I learned the hard way if I wanted something done with my female staff, first I had to sell it with just a few key women on the staff.  Dealing with an alpha female was much different than an alpha male in more than the obvious ways. The ways I needed to learn if I was ever allowed to completely be welcome in the women's sandbox. I needed to win over the alpha females first.

I made it when I paid my gender dues and was able to own my life. The confidence I live with now is but a side benefit.

Trust the Process

 

Image from
UnSplash

Over a very long life of considering and attempting a MtF gender transition, I went through many highs and lows. 

On occasion more lows than highs as I went through the process of trying to balance both of my primary binary genders. In other words, I did plenty of inadvisable things which came back to haunt me. I was fortunate in that I didn't experience bodily harm on a couple of occasions when I was in  places I should not have been as a novice transvestite or cross dresser. Where? On a dark, late night urban city street to name a specific one. I did get stopped one night and was lucky I got out of it by just giving five dollars to a couple of panhandlers who clearly wanted more. Through all of my mistakes I just had to trust the process.

Seemingly the process was I had to pay my dues before I was rewarded with any positive feedback as a transgender woman. All the times when my second wife essentially made fun of the way I looked, just made me try harder to work on the many facets which went into a more convincing image as a feminine person. I knew I had made strides when she had to ask me to help her with her makeup on special occasions. I had trusted the process and kept on working hard and it worked for me on those occasions. Even though she had given into my makeup expertise, my wife still didn't give me an overall approval rating in how I presented. 

The farther I made it along in my transgender journey, the more trust I needed to put into what I was attempting to accomplish. All in all, I was trying to build my way into living a dream and I had so much to lose if I had failed. I say often, because one of the reasons I kept going was I felt so natural as my feminine self. When I did feel natural, it was easier for me to blend in with the public and overall present better to the world. I was rewarded when I was able to spread out from the gay venues I was going to and made my way into becoming a regular at several straight, mainstream sports bars I always enjoyed as a man. In them I was able to enjoy my favorite teams along with a big cold draft beer without any problems. When I was recognized as a regular. Probably the hardest prize to attain was my restroom privilege. As you beer drinkers know,  beer doesn't last long with you and being able to use the women's room (again without complaint) was huge.

Trusting the process also gave me added confidence in myself. Even though on occasion I was still petrified, I still was able to interact with the world and learn to enjoy myself. I finally made it to the point of feeling there was nothing wrong with me and if someone else had a problem, it was theirs to deal with. 

As I look back on trusting the process, for me, being allowed to begin hormone replacement therapy medications involved the most trust for me. I needed to trust the medical community the meds would not hurt me and move on from there. I was fortunate in that the process worked for me and I loved the results. By the time I tried HRT I was used to taking chances with my gender transition and hoped I could go even farther. To living my life fulltime as a transgender woman.