Halloween and Gender Breakthroughs

Halloween
Image from
the JJ Hart
Archives. 

Back again we go to Halloween and the effects it had on me as I developed into a novice transgender woman.

Very early on I learned when I cross dressed head to toe as a woman for a Halloween party, I would be cut out of the male club and my male friends would ignore me. Very early signs of losing any male privilege I had built up over the years. On the other hand, I was not ignored by many of the other women I knew from before who took the time to comment on my shaved legs and "costume." Both were small but definite signs of what I would face in the future if and when I decided to enter the public as a transgender woman. 

Over the years, my tastes in Halloween "costumes" changed from just wanting to be slutty, all the way to trying to present myself as a cis-woman would at a party. Plus I needed to overcome any fears I had of going to the party as a woman and mostly giving up on having a traditional good time partying with friends I had known for years. Again, just a small dose of what it would be like to cut all ties with my old male life and start all over. 

Everything began to change when my "costumes" began to evolve. One party in particular stands out in my mind. It happened when my second wife and I were living in the metro New York City area and I was managing a food location. It just so happened I was invited by one of my assistant female managers to go with her and several of her friends to a Halloween party they were going to. Without hesitation I said yes and wondered how I was going to explain it away to my wife. She never was into Halloween much and turned out she did not much care so I set out to put together an outfit for the evening. I decided to go semi-sexy (or try to) and chose my short mini dress, heels and dark wig for the evening. Off I went into the great unknown of not knowing where I was going and with whom.

It turned out, where I ended up first of all was at the house of my manager and to my pleasant surprise I learned all of her friends who were going were all tall attractive women dressed approximately the same as I was. As I walked into the room where they all were waiting, you could have heard a pin drop as they all looked me over from head to toe. Once they realized who I was, off we went to the real party which was being held at a small bar near to her house. The first thing I thought of was how far was I going to have to walk in my heels but the distance was not too bad and I was on my own cloud nine. I mean, here I was with three other women my height dressed the same way headed for a party. I was scared but excited by the time we arrived at the venue. Once I got to the bar and had a drink or two I started to calm down and learned another couple of gender break throughs. 

The evening turned out to be my first ever girl's night out because I was able to blend in so well with the other women I was with and I learned the power of being able to blend in with the feminine world. The second big breakthrough I learned was how to handle being approached by a man who perhaps did not know he was talking to a transgender woman. I was even asked to dance by one man. Finally, I learned single women of a certain age have a tendency to mark out their own territory when it comes to attracting male companionship. Once we all arrived in the venue, I was left very much on my own. 

I did not know it then, but all of the gender lessons I learned would come back to help me later in life. So much more than an empty comment about how good my shaved legs looked. As my second wife kept trying to tell me, I hadn't paid my dues yet to be considered a good feminine person. Trans or not.   

Transgender Instincts

Image from Atich Bana 
on Unspalsh. 

 First, I need to apologize for missing a post yesterday. I went to my primary provider at the local Veterans Administration clinic for my semi-annual checkup. While  I was there, I was able to receive my flu and Covid vaccines at the same time I was having my blood labs completed. By the time I had stopped and picked up lunch on the way home, I was pretty much ready for a nap and just laid down. By the time I woke up, I had ran out of time to do a post at all.

The visit itself was very mundane and I did not receive any negative responses at all and was never called "Sir." So I chalked it up to a win. In the past I wasn't so lucky and thought about reporting a couple people there for their transphobic behavior. For whatever reason, things have changed for the better. 

Now, onto instincts we have to develop as transgender women or trans men in order to survive in an often hostile world. Especially true for trans women. It seems we have to be on point at all times with our appearance just to get by and appearance is only the beginning. We need to move smoothly like a woman and learn to communicate one on one with mainly the other women we meet. I know I was petrified when I first was trying out the world as a transgender woman. Then, on a totally heightened level were the aspects of conquering and feeling comfortable in women's only spaces such as rest rooms. Which always is a topic for another blog post. Except when it came to the times when I was stuck in line at a restroom  and needed to make polite conversation with other women. 

These days, having your instincts about you as a woman, trans or not, is more important than ever before.  Depending on where you live, outspoken gender bigots have made our business their business. Plus as we transition into the feminine gender world, we need to be careful when it comes to our personal safety. In particular ignoring dark, deserted places such as sidewalks and parking lots. In particular, all things cis-women learn from a young age. Of course, I needed to find out the hard way about my own safety issues and was lucky I did not find myself in more serious harm than I did.

Sometimes, I feel interacting with the world as a transgender woman has meant developing a sixth sense. For me, my hearing improved as I strained to hear what someone else may be saying about me behind my back. From then on it is my decision on what do next. Recently, I have decided to stare the person down and even challenge them. I have spent too many years living to do anything else. 

Our instincts are powerful basics in our lives and changing genders brings a huge challenge. We have to start all over and learn our lives again. Being transgender women or trans men just brings a bigger challenge. On the other hand, learning to play in the other genders sandbox presents a unique challenge in life which very few humans will ever realize. 

Hopefully, we all can make the best of it and go though a safe and stable gender transition. 

Becoming Me

Image from the 
JJ Hart
Archives. 

As I bridged the gender gaps in my life to survive, I did what I perceived to be cross dressing as a woman in my family's mirror. 

Slowly I began to learn the makeup and fashion tricks the girls around me used to look their best. At times it seemed I was attempting the impossible as puberty set in and my body began to go through many unwanted male changes. Like it or not, I was stuck with testosterone poisoning and I would somehow have to get use to living with it. I was becoming a me which was very much unwanted. 

As I got by in life, I learned to camouflage my broad shoulders, and torso (among other negatives) and try to emphasize my positives, even if I needed to do it with feminine style padding in all the right areas. Since I was told I had good legs at the Halloween parties I went to, naturally I tried to emphasize my legs when I dressed. 

Sadly it took me many years to learn the truth about myself. Yes, it was true I was a cross dresser but not the way I always thought I was. In no way was I a male cross dressing as a female, all along I was a woman cross dressing as a man. Once I arrived at that point in my life, suddenly everything began to be so much clearer. I just wish I could have come to the realization so much earlier than I did. I always use the excuse to myself the world itself held me back in the pre-internet years before very little was being published or researched about gender issues. In fact, I still remember in my youth the news stories about the police rounding up and arresting men dressed as women. How could that be? 

Still I persisted and remember vividly the night I dressed up in a mini skirt, panty hose, heels wig and makeup and headed to a nearby gay bar when my wife was away. I was so scared and once I got there and was admitted through a locked door, I only had one drink and left before I even relaxed and I never had the opportunity to go back before the owner died and it closed. Even still, my adventure that night helped me to become the transgender person I wanted to be. At that point, the problem still was, I did not totally know who I was, or face up to her yet. But I was diligently working on the problem by researching my feminine life. 

To do the research, I needed to risk everything and leave the safe surroundings of the mirror and enter the world. I started with going to more gay venues and becoming quickly disillusioned when they all thought of me as a drag queen. Lesbian bars were better but I did not find true acceptance until I became brave enough to go to straight places. There I could watch my sports, drink my beer and become accepted as a regular fairly quickly by the staff. I minded my own business, tried to be friendly and tipped well and was in. Even though I knew they knew I was transgender. it did not matter and along the way I think it even helped me. One way or another, I was taking giant steps towards being me and I knew there was no way I could ever go back.

Perhaps the biggest step I ever took on the gender path to being me was when I started on gender affirming hormones. After being approved by a doctor, the changes occurred quickly.. In addition to the external changes such as breasts, hair and skin, I experienced internal changes also. My emotions changed as well as my whole life just softened. The entire time of gender adjustment was one of the most magical times of my life. 

Overall, the discovery of who I really was as a transgender woman was a terrifying yet exciting journey. One I don't regret taking, once I faced up to her, I was so much happier.   

The Prom Gown

Image from Joeyy Lee
on UnSplash

Years ago, I received a prophetic statement from an unknowing doctor when our family was on vacation in Canada. 

When we were not out fishing with Dad, we played football on a hard-packed lot behind the fishing camp with a bunch of local kids. Being the budding football star I never was, I decided to try to play running back and was actually successful bulling my way through the opposing boys on the other team, for awhile. On a play I would learn to regret, I was picked up and thrown down on my shoulder and suffered a broken collar bone.

I say regret primarily because my Dad was not amused about having to interrupt his vacation to take me to a hospital for treatment. At the hospital, I had X-rays taken and was diagnosed with a broken collar bone. I was seen by a doctor and had my shoulder bandaged up in a sling and was told it would heal on it's own. Leaving only a tell tale bump which showed it had ever happened. Then the doctor said, since I would not be wearing any prom gowns in my future, it would not matter anyway.

I thought at the time, wait a minute! What if I wanted to wear one of the beautiful gowns I had seen on women in my future. What then. I think that comment hurt worse than the actual breaking of the bone. Plus, when I did go to proms and was stuck in an ugly tuxedo, I always looked at the girls around me for any tell-tale bumps to show a collar bone break. I never did see any. 

Along the way, I had several other instances of my feminine aura shining through. I have/had a nephew who from an early age developed a very unsavory attitude towards life which sometimes carried over to me. It started with my politics clashing with his right wing bigotry and going from there. On several occasions, he secretly complimented me by saying I threw a football like a girl. He even said one time when I bought my new Porsche Boxster, I had bought a girls car. Like I said, he was trying to hurt me but was secretly making me feel good. I could not wait to be the attractive blond woman in a sharp sports car.

There were other times when I was called feminine when I was doing my best to be a macho man. Several times at work, I was called "Ma'am" out of the clear blue sky in the middle of a normal conversation with a customer. Looking back, I think it was my feminine aura slipping through my male fence. 

Even though it took me years to realize my dream of living as a transgender woman was much more than living as a part-time cross dresser, I realized there were several tell-tale signs along the way. Maybe the doctor was trying to tell me someday I would want to actually wear a beautiful prom dress which showed off my collar bone break bump. Or my evil nephew would go on to having his own insecurities to deal with. I have not seen him for over a decade, so I don't know or care. He would probably just say he was right about calling me a girl. 

It turned out there were many people who saw through my disguise and at the least knew I wasn't who I was desperately trying to be. A stable, non toxic, productive man. I failed miserably and all I ever wanted was to be the one wearing the beautiful prom gown.   

Calling me a woman was the ultimate compliment. 

Feeling the Pain

 

Image from Eugenia 
Maximova 
on UnSplash.

Learning on the fly all I needed to know concerning my authentic life as a transgender woman often resulted in pain.

The pain, early on mainly materialized when I rushed the process of going out in public as a novice transgender woman or cross dresser. Many times I was reduced to tears following being stared at or even laughed at when I was simply out walking around. I felt the pain for years until I finally realized I was the problem and sought out the reasons why. The main reason was (as I always mention) my male ego was dictating my femininized fashion sense. He was thinking attempting to dress sexy would somehow validate myself as a woman. Of course, it didn't and just made me look ridiculous. On the other hand, when I dressed to blend in with other women, they validated me as a woman.

My frustration and pain increased until I became fed up with the entire process and changed it. My thrift shopping adventures began to change to reflect my new fashion sense. I was held back in many ways by my budget and knowledge of what fashion I was trying to buy. Sizing was an example, as I struggled to find what looked best on my testosterone poisoned body. I did not have the benefit of having any feminine characteristics to begin my journey so trial and lots of error is what I went through. Every time I learned a fashion choice I made  just would not work, I felt the pain return again.

My situation improved when my overall confidence improved to a point where I was able to use the women's changing rooms. When I could afford to go to a mall clothing store, I always checked with a clerk first to see if I was to be accepted so as not to feel the sting and embarrassment later. In the thrift stores I went to, the changing  rooms were not monitored anyhow, so I never had to ask. As I said, when I had the opportunity to try on clothes ahead of time, my improvement rate went way up and my fashion pain way down.

After conquering most of my fashion pain, next up came my paranoia over communicating as a transgender woman in the world. Of course I quickly discovered I had no idea of how women communicate between themselves. I found myself on several different levels when I dealt with the world. Once I figured out I was not "fooling" anyone else and just resorted to being myself, my life improved. One level of woman just did not care and basically ignored me while another level was curious and wondered what I was doing in their world. Overall, I was learning on the fly and had my share of pain such as the one transphobic woman I encountered at a party Liz and I attended many years ago. She was actively harassing me about what my dead name was. She was so evil, the experience still causes me pain to this day.

Overall though, when I compare my transgender journey to others I read about, I suppose I have had it lucky. Even though I had suffered a lifetime's worth of pain when I lost my wife, several close friends and my business in a span of five years, I was able to find new friends and rebound. Mainly because the friends and Liz accepted me as my authentic feminine self. I guess karma was paying me back for a lifetime of wondering what I was doing about my transgender self. All the years of doubting my gender existence came back to be a strength when I quit being a victim in my own life. 

Sure I was transgender but suddenly it became a strength not a weakness and the pain was behind me. 

     

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine. 

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. 

Affirmation

 

Recently I had a very important reminder of my initial affirmation as a legal female in the world.

It came several years ago when I decided to have as many legal documents as I could changed to reflect my authentic feminine self. One of the major documents I needed changed was my Ohio driver's license. I made sure I acquired all the name change documents plus a letter from my therapist to insure I did not have any problems. The process was scary but exciting because among other things, I needed the picture ID of the license so I could vote. 

It just so happened my license was due to expire just ahead of the all-important election coming up in November so it was important for me not to procrastinate until the last minute so I can cast my vote against tRumpt. 

In many ways, being able to renew my license symbolically was similar to renewing my gender vows with myself. As far as completing the process, it was easy this time because I was already in the system as female and no one questioned me. Probably the most difficult part was having my picture taken because of all the insecurities I feel when it comes to my appearance. For the morning I chose one of my most feminine tops, applied a foundation, eye makeup, lipstick, blush and tied back my hair and was ready to go. I arrived early and only had to wait approximately fifteen minutes before being waited on. 

Even though I knew the process would be nearly painless, for some reason I was still suffering from needless paranoia. I was able to put it all behind me and reaffirm  myself as a legal transgender feminine person. 

Next stop is my upcoming mammogram appointment which is in the process of being scheduled now. I consider mammograms as a slightly unpleasant rite of passage I need to go through since my maternal grandmother died from breast cancer years ago.

Affirmation is good.

It is NOT a Choice

Image from Alexander Grey 
on UnSplash

I still get aggravated when someone says being transgender is a choice.

Realistically, why would I have ever chosen to live the life I am living. Would I have made the choice to give up everything I worked so hard to achieve just to put on a dress, makeup and heels and attempt to live a feminine life. All the material benefits I had acquired as part of my life as a white male privileges disappeared for good, if I wanted them to to or not.

Suddenly, I learned the hard way what it was like to have my personal security threatened as well as being mansplained when I attempted to insert my feelings on a topic I knew quite a bit about. Quickly I discovered many examples. I nearly found out the hard way, if I dressed too provocatively at a mixer, I would be cornered and harassed by an over bearing transvestite admirer. In an instant, I learned how it would be to be a helpless woman being overwhelmed by a much larger man. Not a pleasant experience and it was not all of my lessons. One night when I was blissfully minding my own business on a dark city sidewalk, I was approached by two sketchy men wanting a handout. Fortunately, I still had a lone five dollar bill for them and they went on their way. From then on my new feminine common sense began to grow and I started to develop the gender protective sense all women acquire as part of their life experiences.

None of what I was experiencing was a choice and not part of me being validating  myself as a woman. All I needed to know was I had no choice but to follow my path if I was able to look myself in the mirror and know I was doing the right thing. Coupled with the natural feelings I was experiencing, my supposed choice was made. 

I knew over a span of time, I would learn to deal with being mansplained was something I just had to deal with as a transgender woman. I will never forget the day I had to sit in a tow truck and be subjected to being bored when the driver was telling me how the truck worked. Finally, I gave him my best blond act until he finished all his rock bottom explanations. On one of my few dates with men, quickly I found I knew nothing about subjects such as sports and politics.

Why would I choose to be something as difficult as being a woman? My entire life became dedicated to proving the world wrong. I could carve out and experience a new life as a transgender woman and thrive. But again, I needed to prove all the naysayers wrong. The only natural feminine attribute I started with was my brain. Which for some reason, kept telling me I was doing life completely wrong because I was living it as a male instead of my more natural female. Finally, all the pressure to change and all the stress to explore the world as a trans woman. I was living in a world of alternate facts which was increasingly too complex to handle. I came to the point where I felt as an impostor when I went out of the house as a man. Can you imagine that? Feeling as an impostor when you attempt to live as your birth gender. It happened to me.

All the process proved to an outsider is gender issues are not a choice. During the process none of us understands, we are born into system we never asked for. The path is often a bumpy one with plenty of curves and stop signs. We have to wait our turn before we move on. 

For any number of reasons, the true number of transgender women and trans men may never be known. One thing is for sure, there are many more hidden transgender individuals waiting to take their turn and enter the world. Regardless of all the negative publicity we receive, transgender people have been around forever and will remain a part of the human experience. After all, we don't have a choice.

Down but Not Out

 

First Girl's Night Out.
I am on the bottom row, left.

There have been many times during my transgender journey which I have felt down.

However, a little voice in my head kept telling me to keep going and if I did, I could achieve my dream of living a feminine life.  I write many times (mainly for those of you who are still new to the transgender or cross dressing world) how I was ridiculed intensely when I first tried to explore the public as a woman. After being laughed at, I always headed home in a hurry and tried to go back to the drawing board to try to determine what I was doing wrong. It took me awhile to figure out I needed to get past my male ego of what a woman should look like and into blending in with the rest of the female world. The mirror and my head turned out to be powerful opponents. 

I need to stress, it took me years of being down to turn my learning curve the opposite way and turn my frown into a smile when I was out in the world. Along the way, I needed to adjust my thinking on how I was accepted. I needed to realize I would never be the most attractive woman in the room and begin to fall back on my personality to get along. I was transgender and different but so what I was a good person. When I accomplished being at the least friendly to others, I began to be accepted into small groups of acquaintances who accepted me for my true self. In one of the venues I became a regular in, I have vibrant memories of a group of five diverse women and even a few men who I could set in with and have a beverage. 

It all proved to me I was resilient and could survive most things, including my growth as a transgender woman. Even though life was about ready to deal me several severe setbacks I was not expecting, I could make it. 

When life did hit me with setbacks, they were sledgehammer type blows. It seemed life was fond of giving me setbacks such as my wife passing away along with most of my best friends. It nearly finished me off when I had to close my restaurant I worked so hard to buy. More or less, I was left with my house, two dogs and an old car to re-erect my life. 

The old saying the darkest hour was right before the dawn was true for me  I was down but I had one huge card up my favorite blouse's sleeve. Since I was so far down why not start all over again as my dream self. My inner female had always been strong enough  to fight for her existence, so why no let her have it. Karma was on my side also, as it was about this time the Veterans Administration  health care system which I was already a part of suddenly approved the use of gender affirming hormones for transgender veterans. I only needed approval from a VA therapist to start the program. It turned out I was with Dr. C. my therapist for over ten years and she worked miracles for me.

Maybe it was because I was able to outlive a suicide attempt and years of self destructive behavior that I was able to come full circle in my life and end up on my heels. I was down but not out and discovered people in the world who could and would step up to accept me as my authentic self. Even though I needed to make the effort first. Which for me was very difficult. In the end, the whole process made me a better person.

Gender Anxieties or Paradise

Image from Cacique 
Nacimento on'
UnSplash

During my gender transition, all the way to today, I have experienced my share of anxieties.

Early examples revolved basically around the way I looked when I was cross dressed in my very limited feminine wardrobe. I kept telling myself I was OK when I with my cross dressing and I was for a couple of days before my gender anxiety returned. Making me difficult to live with. Paradise was fleeting and hard to find. 

Much later on in life, when I began to try out the public's perception of me, the whole process was anxiety ridden. When I used to shop till I dropped in clothing stores, my feminine life was easy because everyone was just interested in selling me something. Or I was in thrift stores where the clerks barely looked at me at all. Maybe because they were used to waiting on cross dressers? Very soon I came away with feeling no anxiety at all when I shopped so I felt I needed to challenge myself further. I needed to see if it would ever be possible to live my dream of being a full-time transgender woman. It was close to this time also when I began to seriously challenge the world as a woman at various Halloween parties I went to. Most of them happened when I was married to my first wife who knew I was a crossdresser  when I married her, so there were no surprises when she saw the "costume" I settled on. 

Even at Halloween, I experienced growth with my gender issues. When I dressed trashy, early on, I was treated the same way but when I decided to see if I could present as a business woman at the party, I was treated with more respect and even surprise at my true gender. Little did I know at the time when I dressed as a woman, I was presenting as my true gender. Very quickly I learned, Halloween was never enough and I needed to express my authentic self as a woman more than once a year. When I did, I began to do more of the household grocery shopping as a novice transgender woman as well as haunting the antique malls and bookstores for the perfect gift for my wife. Anything to take me out of my male comfort zone. When I was successful I was in paradise and when I failed, of course the opposite occurred and  I was sent back to my gender drawing board to re-think my plans. Could I ever make it to my dream the way I was heading. 

Spoiler alert, I could and did make it. Somehow and through the help of therapy I was able to work my way through a large amount of my gender anxiety. My therapist helped me to realize there was absolutely nothing wrong with my transgender desires. Which was as close as she could come to telling me I should proceed with my dreams. Paradise was reachable if I wanted to pursue it farther and I had already accomplished most of the hard work. I had established myself a foothold in the world as a transgender woman and it felt so good and natural, so what was I waiting for.

The answer to what was I waiting for was the outside chance my male self would finally get on board with my decision. He didn't and hung on to the bitter end. In fact he tried to ruin my transition all the way to when I was medically approved to begin gender affirming hormones or HRT. What happened was, the HRT changes were so dramatic, even my male self needed to finally give up and go away. He finally did, leaving most all of my gender anxiety behind and replacing it with a lifetime of feeling freedom such as I had never felt before. 

I had paid my dues and it was time to move on.

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. 

Do We Have a New Neighbor?

 

Image of Porsche Boxster. 

Similar to so many of you, I struggled for years trying to figure out how to get out of my house without the neighbors noticing.

I was unfortunate in that I lived in a medium sized city on a very busy street. On the other hand, I was lucky my house was ancient and had many doors which I could escape out of if I was just trying to escape for a quick walk. Once I was able to cross the busy three lane street in front of the house, a quiet neighborhood awaited me with limited chances for even seeing anyone. 

From my walking adventures, I very soon wanted to get to my car and drive. At the same time, I needed to be ultra careful I didn't get caught by my second wife or any of her friends. The problem was, one of the only deals I made with my wife who knew I was a cross dresser was I could never leave the house and here I was doing just that. Plus, I had the additional problem of being seen at Halloween parties cross dressed by several friends who could connect the dots if they saw me again. Needless to say, the whole process was risky. 

For the longest time, I was able to park my car on a side street and hurry into it's temporary safety without being noticed. At least I hoped so. From there, I could leave the town in head out on the interstate where I could tease truck drivers in my mini-skirts which somehow validated me as a woman. Finally, I grew bored of truck drivers and concentrated on improving myself as a new novice transgender woman. I had issues such as moving and communicating in a new world, I needed to work on if I was ever going to be successful in achieving my gender dreams.

Still I was reckless in my quest to not be discovered by my neighbors. My prime example is the new car I was able to buy with my restaurant monthly bonus money which happened to be very successful. I had always wanted a new Porsche following my days in the Army when I was stationed near the company's headquarters in Stuttgart, Germany. I was able to afford a low end (for a Porsche) Boxster which I dearly loved. By buying the car, any ideas of driving a car the world would not recognize went out the window. Very early when I finally took ownership of the car, my thoughts turned to being the blond behind the wheel of a fancy sports car. 

I couldn't take it any longer and ended up compromising on the how's and why's I was going to drive my dream car as my dream woman. I started by cross dressing as far as I could except for my wig, Putting the top down and heading out of town. I needed to not wear the wig also because I was afraid of it blowing away in the air when I was driving. Very soon I found out how popular the car was when the first night I drove it to the lesbian bar I always went to. As soon as I arrived and ordered my first drink, another woman walked in and loudly said, who does the car belong to? I want a ride, so out the door I went wig and all to show off my dream. The woman was thrilled, as was I and my wig stayed put.

By this time, I didn't really care what anyone thought about me and I enjoyed being the blond in the Boxster for as long as I could before my restaurant went under during a huge economic downturn it could not survive. Sure I had the negative responses I had anticipated but it was increasingly not important as I was living my truth. As far as the neighbors went, they moved away and the new tenants basically either did not know me at all or did not seem to care what I was doing. Which was exactly the way I wanted.