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.   

Running Against the Tide

Sarah McBride is running for the United States House of Representatives from the state of Delaware. Sarah grew up in Wilmington, and currently represents fifty thousand of her neighbors. Despite her impressive background in community service, one thing sets her off from all others seeking a seat in the House of Representatives, she is transgender.

Even though she is an example of a person going way past being transgender and just being her, she takes it to a whole other height when transgender people are under attack at so many levels by a certain political party I will not mention. At the least, she is an inspiration to the rest of us. 

Just last night I was watching the Texas-Georgia college football game and was unpleasantly surprised when a commercial for Republican Senate candidate Ted Cruz popped up on my television in far away Ohio. As luck would have it, Ohio and Texas have very competitive senatorial campaigns going on. I would estimate over ninety percent of the anti Democratic candidate ads on television involve false transgender claims. Which are brutal and false. Last night I was enjoying a game when the same commercial popped up with only the names had changed. It was a stark reminder that a major player such as an Elon Musk or Peter Theil are aligned against us. I forgot to mention they are both billionaires capable of buying off huge portions of the federal government such as politicians and supreme court justices. 

Enter Sarah McBride, a light in the end of the tunnel which is not the train. Many more pro-LGBTQ political candidates are running in this year's crucial election. As a group we must put our differences behind us and our future in front of us as we must identify and vote for the proper path forward. Sarah McBride is proof it can be done as she is favored to win her race. We need to make sure she is only the beginning.    

 

How Far will You Go?

Image from UnSplash.

I have always viewed my transgender journey as a series of upward steps. A few of the steps were short and easy to take, while others were the opposite. The steps seemed to be impossibly steep and dangerous to proceed. 

Early steps were thrilling and even exciting as I snuck behind my family's back to cross dress in front of the mirror. Even so, the risk of discovery was anything but easy because I was risking so much. In those days, discovery meant a trip to a therapist who knew nothing about gender issues and even worse being treated as if I was mentally ill. 

At that point, looking ahead, I probably knew deep down, things would not get any easier with my gender issues. But, time would tell. As I progressed during my life, it suddenly became obvious  my gender issues were not going to go away. In fact, they were only to become much more serious. Mainly because my male life was becoming so much more serious too. Once I made it through my military service, I settled in to raising my new, small family which I hoped somehow would make me more of a man, while deep down I knew it would never be the case. I wondered how far I would have to go to carve out a good life. 

Fortunately, I was able to even though the trip was difficult, I made it by deciding I would go as far as I needed to go to satisfy living as my feminine authentic self. Initially, I had several major hurdles to conquer. Such as, did I want major surgeries which were much rarer and expensive back in those days as well as how my sexuality would play out as my new self. 

Since I did not have any insurance to cover the surgeries, paying for them was out of the question so I moved on. Next was my sexuality. Since I had absolutely no experience in sexual time with men, I did not know how it would go. It turned out, I did not need to experience much time with me, I never had to move on from my sexuality with women. I was becoming a transgender lesbian. 

Of course, the further I progressed in my new world, the more I had to lose as far as family, friends and employment. I needed to prepare to lose it all if I needed to. I needed to determine if it all would be worth it. In my case, all the years of fear and struggle proved to be worth it. Thanks to my lesbian wife Liz, I was accepted for who I was. 

To arrive here, I did not have to go through extensive operations and change my sexuality. I have always thought gender was between the ears and not the legs so it did not matter to me. I guess it proves how diverse the transgender community is, if we allow it to be. None of the "I'm more trans than you" syndrome which is hurtful to us all. Especially now, in a political environment which is setting out to erase the trans population, we ALL need to be united and not divided behind a bunch of archaic labels, such as cross dresser and transsexual individuals. 

Regardless of the label, we all had to decide how far we want to go to satisfy our gender urges. Or sadly, how many risks did we want to take to change our life forever. It all proves how we never had a choice in who we are as transphobes seem to think we do. How far you go is entirely a personal decision which takes a lot of work and trial and error to accomplish. It' all depends how in depth you want to go. For example, the night I went out to see if I could meet and blend in with other single women on their own turf and survive. I did make it and knew I could never go back to the life I had before in the mirror. I wanted to go more in-depth. 

From then on, I needed the confidence to do it.

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. 

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me. 

It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.   

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Intimidating Women

Library of Congress 
image from 
UnSplash.

During my life, surprisingly so, I have encountered many intimating cis-women. 

Probably the most intimidating of all was my Mom, a dynamo at a mere five foot two inches tall.  From early as I can remember, we clashed on many different issues probably because we were so much alike. On the girl side, I was fascinated from a young age when I watched her skill with makeup and hair. I could only dream of ever duplicating her prowess. Of course I would never get the chance for her to ever see the fashion skills I finally developed as the daughter she thought she never had. 

As I grew up, my intimidation of girls of all kinds increased. I was so jealous of their ability to dress in pretty clothes and wear makeup continued. In addition, I was so shy, I was afraid to communicate with girls at all. So my problems continued to get worse. I never had the chance to circle back to where I began. All the time I was cross dressing in front of the mirror, it was a very solitary, lonely experience as I craved the peer feedback other girls my age had to work with. 

The older I became, the more I admired women who were stronger and spoke their minds. You might say I was intimidated in the most positive ways by strong women. I was even attracted to them to the point I chose one for my second wife who I was married to for twenty five years. Even though she knew I was a cross dresser from the very beginning, somehow I secretly thought she would help me with my on-going quest to be a feminine person. She never really did help me much and very much resisted any ideas I had I was a transgender woman. 

Perhaps I am attracted to strong successful women because I wish I was one. I so admired the women managers I worked with because of all the extra skills they had to use to be successful. Most if not all of them had families to support at the same time they worked a full-time job. I was in the restaurant business and some of my best kitchen managers were women who dealt with macho kitchen crews. 

Being a transgender woman, I think sometimes I intimidate other women. Sometimes they seem to melt with kindness such as the hostess last week when my wife Liz and I went out for my birthday dinner. She was beside herself to make sure we were satisfied with our experience. As I can remember, intimidation on my part of a guy was when I was shopping at a grocery store years ago for the families groceries. In those days, a fashionable woman who had the legs wore an oversize sweater with flats and a mini -skirt, so I did on that day. As I chose our food, I tried to contain my fear in checking out, I found I was wrong.  As it turned out, the store was nearly empty and only had one check-out lane open with a woman cashier and a male bagger. 

It turned out, I really intimidated the bagger, he blushed and stuttered when he asked me if I needed help taking my bags to my car. I looked at the cashier and him when I said I didn't and she gave me a slight knowing smile. I wondered then, if she knew I was transgender at the time or not. Regardless, it was quite the experience. 

It wasn't until I transitioned into a feminine world as a trans woman did I fully understand all the nuances of what it takes to be an intimidating woman. For example, some women use their heels to begin the process. Heels give a shorter woman a height advantage to be able to compete with the men in their world. Plus, these days, more and more young women are becoming educated to give themselves an extra advantage in the world. 

It turns out, in my life, intimidating women are becoming the norm as the future is female.