No Participation Awards for a Trans Woman

Image from Brett Jordan 
on UnSplash.

As I traveled up my very long gender path with all its stop signs, I realized there were no awards for just participating coming my way. In fact, just the opposite was true.

Every time I was able to cross dress in front of the family mirror and not get caught, I experienced major gender euphoria but no awards because I knew I would just have to go back to my boring male life which I wanted no part of. Since my feminine self was deeply hidden from the world, there were no awards when I mastered a certain make up look or did not run my panty hose. On the other hand, I could expect some sort of gratitude when I achieved good results as a boy. I hated the total imbalance of the system I needed to live under with no available choices coming my way soon.

It wasn’t until much later in life did, I began to experience any participation awards at all. In the very beginning after trips to the big malls I was going to, even on the nights I was laughed at and scorned for my appearance, I felt at least I had tried and needed to go back to my cross-dressing drawing board to come up with ideas about what I was doing wrong. After setting aside my stubborn ideas of trying to dress sexy like a teenaged girl, and dressing age appropriate I was able to blend in with the ciswomen around me and not cause any undue attention to myself. I gave myself a bigger reward when I reached that major milestone in my life back then as a part-time cross-dresser.

Then, I became frustrated because it seemed the awards began to become harder and harder to come by as I started to overachieve as a transfeminine person seeing the world for the first time. Those were the days of trying to overcome a portion of my guilt for sneaking out of the house dressed as me by trying to do things which helped the household such as grocery shopping or better yet, trying to find my wife a garden gift at one of the nearby antique malls I went to. She was a huge gardener, and I thought an occasional gift would please her but probably pleased me more because it helped soothe my guilty conscience and gave me an imaginary award to put up on my mantle. I wish I could say I had a lot of awards, but they were very difficult to come by. Plus, my collection would be destroyed every time my wife caught me out of the house, and I became discouraged and decided to purge all my feminine belongings only to have to start all over again. Until I realized purging was fruitless and my desire to be a woman ran too deeply than just having the clothes, shoes and wigs that I had collected.

Overtime, with all the purges I attempted, I became better at keeping key items of my wardrobe I would need if (ha-ha) the urge to be a trans woman hit me again. I was not the sharpest tack in the box and still had not realized being trans was apart of me and would never just go away.

In the meantime, I continued to go out at night in the world and collect my participation awards as I learned what it really meant to be myself. To do so I needed to leave the gay bars behind that I was frequenting where they only thought I was a drag queen and try out the real world for a change where at the least I could be accepted as a woman from a different past. To do so, I needed to hitch up my big girl panties and do a deep, scary dive into the world I wanted so desperately to be in. I was growing increasingly tired of living a lie as a man and wanted out. In the beginning, I still took what I thought was the easy way out. By going to venues, I frequented often as a man and had wondered how it would be to live it as a transgender woman. It also helped that I was able to see how single women were treated in the straight places I was considering going. The last thing I wanted to do was to feel unwanted or afraid being a single woman in a venue full of couples.

After much thought and caution, I tossed my misgivings aside and considered what was the worst that could happen. My frail ego would be destroyed, and all my participation awards would be destroyed was my first thought. Then, I relied on all my new-found confidence as a transgender woman to succeed at my first big moves in straight venues in the world around me. To my amazement, I was treated well in my new world, and no one laughed at me or treated me with disrespect as I left my unwanted male privileges behind to learn what all the female privileges were all about.

I learned immediately one of the benefits was just being treated nicer. Even to the point where I was invited to staff girls’ nights out when the bartenders were concerned, I was lonely. Which I was. Better yet, one bartender set me up with her single lesbian mom whom I remain friends with to this day. Ten years later. There would have been no way that I could have made friends as easy as I did as a woman than I ever did as a man. A major reward for all the years of work I had put into succeeding on my gender path to my dream.

Another major reward I have received over the years comes from all your comments and feedback to my experiences. Originally, the idea was to write a blog (before I even knew what was one) to help others with similar gender differences so they could learn from them. Thanks to you, the idea has grown way past my expectations.

Thank you!

 

 

  

She Was Living Rent Free in my Head

 

Image from Nathan Dumlao
on UnSplash.

It took me years to realize that I had a tenant living rent free in my head all along.

I should have known from day one when I was going through my mom’s clothing that she was here to stay. In fact, she increasingly demanded more and more space in my head to justify her life as a cross-dresser or transvestite as we were called back then. I would need to wait several years for the transgender term to even become popular in our gender diverse society.

Also very early, I realized that the small closet I gave her to exist in just was not going to be enough. When she succeeded in expressing herself in the world in the smallest of occasions, she wanted to increase her space in my head. Prime examples were the days in school during study halls when I should have been actually studying. But I wasn’t as if I was having too much fun envying the girls around me who I desperately wanted to be like the next time I had the rare chance to be by myself and cross-dressed as a pretty girl in the mirror. And I realized I did not want them sexually as much as I wanted to be them physically and mentally.

It was during that portion of my life that I completely did not have any idea of how much rent-free space my evolving trans woman needed for her share of my head. Now I want back all the time my male self-spent fighting her for my life as I lived it. The gender ripping and tearing was certainly no fun, as both genders in my head fought for their right to survive. For awhile I tried the old male fallback of just try to ignore my number one problem in my life and she would somehow just disappear. When, in fact, the opposite was happening. The thrill of putting on a dress, hose and makeup would go away, and in its place, I would have a deep-seated feeling of just doing what was coming to be just natural for me. It was increasingly evident that I would need more space for my rent-free tenant to operate in as she went out to explore the world as a novice transfeminine person.

Following more than a few rough patches when she was going out in the world, my woman began to understand the sacrifice of her male ways it would take to survive. She became more serious and began to work on the basics such as presenting herself convincingly in the world. I went on a crash diet and succeeded in taking off enough weight so I could go down a size or two in the world of women’s fashion and I could find and wear stylish clothes for a change. Along with that major move, I began to take extra better care of my skin. Using a good moisturizer following every shave. Which paid off by not having to use so much foundation makeup and I could look so much more natural as if I was not trying so hard to look like an attractive woman. The trips I started to make to the department store makeup counters for guidance certainly did not hurt my progress either.

I was learning the hard way that I could not cut any corners if I was to be successful in my quest to present successfully in a world of curious ciswomen. I needed to give my rent-free tenant the opportunity to expand her space in my head and the finances to do it. I would be spotted a mile away as a man trying to be a woman if I used cheap makeup and did not do my best to shop for (and try on) clothes that fit me and even flatter my testosterone poisoned figure that I could do very little about. I did learn from my observations of the ciswomen around me that there were women of every shape and size that I could copy from and be successful. Which gave me the positive energy to carry on and pass as a trans woman friend of mine said, “Out of sheer will power.”

Even though the progress of my rent-free tenant was not moving along as fast as she wanted, there were still major obstacles in my way to deal with. Such as what would happen to my twenty-five-year marriage, my relationship with my daughter and the problem of finding a new job as a trans woman in the world. To be sure, all were major obstacles to deal with, so my tenant would have to be patient as she was beginning to understand she was the only tenant left in my head with any power. My male self was just going through the motions of life to keep a job and the outwardly show of male privilege in my life.

Finally, it was time to go on gender affirming hormones and allow my tenants to switch places. My previous rent-free tenant had earned her right to live as the dominant person in my life and my male self was left to pick up the pieces. I should say baggage more than pieces, because that is what he left me to consider in my new feminine life as a fulltime transgender woman. It was difficult to do, but I was able to keep several of my main male building blocks of my life such as my will to succeed and a deep-seated desire to bring my hobbies with me such as my love of sports. Which I learned was alright when I made ciswomen friends with the same passion for sports that I had built up over the years of my life.

While I certainly would not recommend a life like mine to anyone. Letting someone live rent free in your head for all those years was never easy. Perhaps, the only positive was, having all that time to learn the world as a trans woman gave me a stable basis to work from. That is my excuse, and I am sticking to it.

 

 

The Original Witches Ball as an Up-and-Coming Trans Woman

 

JJ Hart.

Back in the day, the Cincinnati area used to host what was called the “Original” Witches Ball around the Halloween season of course. It was called “The Original” because several copycat dances had sprung up attempting to copy the success of the first one.  Of significance to me was the ball that year was actually the third date my wife Liz and I had been on. Our first two dates had been to a drag show and a Renaissance festival, so another themed date would fit right in until we got to know each other better.

Perhaps the highlight of the witches’ ball was the venue itself. It was in a huge vintage Victorian house which had been expanded in the past to include an auditorium with a balcony and stage. For the evening, I thought I would go all the way in black with a hand-picked outfit guaranteed to be fun and just a little on the sleezy side. I went with a short black sleeveless minidress with black panty hose, a sequined net shawl and black heels. Since I was not quite to the point where I could style my own hair and wear it, I decided to wear a long curly black wig I had purchased a long time ago. For the party, we were even able to reserve a nearby hotel room so we could get ready and spend the night without having to worry about driving since it was within walking distance.

As I was to discover later in the evening, the only mistake I made in my outfit was the high-heeled shoes I chose to wear. As the night wore on, so did the strain the shoes put on my feet. Fortunately, I was able to kick them off at key places in the venue which had carpeted floors. I guess you could say I paid the price for fashion the night of the witch’s ball. Other than that setback, I had a wonderful time with Liz enjoying the entertainment on the main stage. The costume contest (which I did not enter) and all the exotic belly dancers who performed during the evening in another part of the venue.

All too soon the party was over, and my head was still spinning over all the wonderful costumes I saw, all the vendors with their merchandise and even getting an introduction to the “Captain Jack Sparrow” impersonator who complimented me on my “costume.”

I was hoping the alcohol I consumed would dull the pain in my feet for the walk back to the hotel in my heels, but it didn’t and off came the heels and on came the sidewalk in my panty hose for the short walk back. For all the fun I had, the brief pain was worth it. Little did I know at that time, I would be able to return to the witches’ ball in the future in a much bigger role as a behind the scenes organizer. And Liz and I would be able to cement our relationship with other entertaining dates.

It turned out that the witches’ circle Liz was already part of when I met her wanted to try to take on the huge task of organizing and putting on another annual ball. The first thing they needed to do was negotiate a rate for the same venue, which was crucial for the success of the event. Since I enjoyed being part of the group putting together another ball, I was given the opportunity to set up a vendor’s table to sell cookbooks and other crafts the group had put together. The fact was not lost on me that I had transitioned with all of them from a transgender woman to just another integral part of the group. Or circle that it was referred to.

 We only managed another couple of balls in the original venue it had was so uniquely designed for. Old and spooky to start with, it was simply ideal for what we wanted it for but the newer future places just did not come up to its standards of uniqueness, and the attendance began to decline. I did add an image showing what I did wear to the last of the old-style Cincinnati Witches Balls. I chose my black silk pants with a red sequined sleeveless top with my own hair this time around topped off with an oversized black hat you can’t see in the picture. Furthermore, I learned my shoe lessons this time around and wore a pair of sensible flats. The only positive I got from researching where we could have our next event was being invited to visit possible venues. Many of which were in Cincinnati brew pubs which meant I could sample some good beer.

These days, the Witches’ Ball event still hangs on in a vastly smaller form as it is held now only in a local bar. I, however, will always remember what the event meant to me. I was able to express myself for the last time in a hyper-Halloween atmosphere where I attempted to dress as a sexy woman and this time with a date who would become my wife later in life. From then on, I transitioned male to female into a world I had only dreamed of and any work I did on the ball was from my new viewpoint. Not to mention, I really appreciated the lack of special attention I received just because I was a trans woman in a group made up primarily of ciswomen and a few men.

I would have never thought just going to such a special venue for an outstanding event would lead to such far-reaching circumstances for me. It proved once again how life can be a strange but wonderful set up of possibilities which are there for you if you can ever set out to achieve them. For many of us that is the problem which hurts us in life. If it is something you can’t overcome.

Thanks for reading along and adding your comments. It makes it all so worthwhile for me!

 

 

You Never Know until You Try

 

Image from Leo Visions
on UnSplash.

You never know until you try was drilled into me as a kid by my WWII generation parents whenever I was facing a potential difficult situation. Little did they know, their insistence on me trying to do the improbable would come back to haunt them in a very different way. Back in those days (in the 1950’s) gender issues were referred to as mental illness and any reference to their eldest son being mentally ill would have been frowned on, so I was stuck wondering if I was really a boy who wanted to be a girl.

The only thing I knew to do was to keep cross-dressing in front of the family’s full length hallway mirror. Imagining I was one of the pretty girls I desperately wanted to be. At the time, I had no idea my gender issues would last the better part of fifty years and take up huge portions of my life. Not that I could have done anything about it if I had tried which I did a number of times when I purged nearly all my feminine belongings swearing never to pick them up again. I was stuck being a male and somehow, I needed to make the best of it. Like so many people I knew with gender issues, purging never worked. The pressure built until I could take it no longer and again, I was accumulating women’s clothes again and wearing them.

At the least I tried to go back to mentally being male full-time and failed miserably at it. All I knew was when I was not thinking about getting out of my dark, lonely gender closet, I was not happy at all and when I at least tried to be me in the mirror it took the pressure off. Even if it was only for a while. At the same time, I was acutely aware that I was doing the best I could to see if I could improve my appearance as a pretty girl. How I never got caught doing all of this, I will never know, and I even resorted to taking plastic bags of clothes and makeup into the neighboring woods so I could escape the prying eyes of my slightly younger brother and family.

My mentality of never knowing you could do something until you try really came to the forefront when I was drafted into the Army during the Vietnam War. Instead of taking the two-year plan with a ticket to Southeast Asia, I took a chance and signed up to try to get a job I wanted in the American Forces Radio and Television Service. With a lot of luck and the help of a congressman whose radio station I worked for, against all odds, I got one of the sixty job slots in the Army for AFRTS. It turned out the whole process turned my life around and taught me that anything could be possible. If you went out of your way to try. Probably the most valuable lesson that I could have ever learned as I looked ahead at my path to becoming a successful transfeminine person. If it had worked for me once, why couldn’t it do it again.

As I set out to leave my gender closet behind and improve my life, I know I took on a journey I would not readily recommend to others. When I started to leave the mirror and join the world as a trans woman, I used a tool that I had already used effectively as a man in my previous life. It was alcohol, and I knew I could use it to build up much needed courage to be in the world as a transgender woman and not get myself into more trouble as I was presenting as a single woman in an establishment which served alcohol. Gay, straight or lesbian, it did not matter. I found I could get by if I stayed out of the redneck leaning venues. I was also well schooled in the artform of driving while buzzed from all my days in the Army when I did all the driving. More than anything else, this was back in the days before the major crackdowns on drunken drivers, so I was safer, and in NO WAY do I recommend what I did.

Also, what I think is tougher these days than when I was intensely lonely and looking for companionship is the world of on-line dating. When I was seeking a date, I played both sides of the gender coin, because I was in the unique position of being a transgender woman who favored lesbians. Looking back, I think I got the most attention from men seeking men dating sites. But just knowing that the amount of trash I would receive was at its best humorous and at its worst, a disaster because I refused to meet anyone in a public place which was not of my choosing. I was stood up more times than I would care to count or remember because my life was destined to change forever when I met my future wife Liz on a woman seeking woman dating site.

Liz responded to my picture saying I had sad eyes which was entirely possible at that time of my life. Amazingly, she lived relatively close to me in a town (Cincinnati) that I had always admired. From there, I began to become involved in her friend’s girl’s nights out and I was able to do more to learn what was behind the gender curtain than I had ever thought possible. The entire on-line dating world for me proved again you never know what you are going to get until you try.

These days again it is more problematic to find someone online with all the scammers out there, but destiny can never find you if you never venture out of your dark lonely closet and light up your path to a brighter future.

I wonder what my deceased parents would think now of what they taught me so long ago.

 

 

 

Letting the Light Into my Trans Closet

 

Image from Sahin Kalijii
on UnSplash. 

Growing up, I had what I considered to be a very dark and escape proof gender closet.

I was part of the pre-internet/social media generation so I could not find the latest online tutorial on improving my makeup skills. And of course, I could not run to my mom or girls’ peer group for any information either. I was stuck with no light in my closet all by myself it seemed.

I stayed that way for years until gender pioneers such as “Virginia Prince” began to shine her faint light into my closet. I had little to no knowledge that individuals such as me even existed in the world. Once I did, I was very relieved I was not the only transvestite as Virginia called us then in the world and I set out to meet others. Before I could open my closet door even a little, I had to convince my second wife that it would be OK to do it. She had known from the beginning of our relationship that I was a cross-dresser but did not like it when I began to let others know of my so called “hobby.” It actually marked the beginning of me opening my closet door to the world and proclaiming I was a transgender woman, not a part time man putting on a dress and makeup.

Along the way, another problem I had was deciding when to take the chance to open my closet door and to which person. I did myself no favors when for the most part, I tried to internalize all my feminine feelings which made me an impossible person to get along with when I was looking in the mirror at my male self and hating what I saw. All the times I ventured out of my closet only to have to hurry back in was wrecking most of my life as I knew it. Not to mention the life with my wife who I envied because she was a ciswoman, and resented because she would not let me explore a feminine side which was trying to see the light of day.

I found my male self-had installed a powerful spring closer on my closet door which was designed to keep me in. Deep down he knew his part of my life was in danger every time I was able to escape the closet and get out into the world. I felt so enlightened and natural when I did, I never wanted to return to my male life and all its drudgery. I was so sick of wearing the same old collection of ties to work every day when better/brighter fashion choices awaited me in my closet at home.

I discovered that the more I outfitted my closet with brighter lights and bigger mirrors, the more I wanted to test my new fashions, wigs, and makeup in the world. Away from my mirror which had the tendency to lie to me. I can’t tell you how many times the mirror told me I looked great only to be rejected quickly in the public’s eye. It took me years to realize that I was expecting too much on just looking like a ciswoman, I had not yet paid my dues on becoming myself and then having the ability to relax and enjoy myself even more.

It helped me too when I began to venture further away from my closet as my confidence as a transfeminine person began to grow. To get there, I needed to be able to look another woman in the eye and communicate one on one with her about the world around us. Men entered the picture too but briefly since most of them did not want to have anything to do with me anyhow. More and more, I did not have to scramble back to my closet following a bad day or night out into the world because I was doing better in my feminine life. All my male could do was sit back and helplessly watch as his hold on me slipped away and all he ended up being was a provider because of his good job.

I arrived at a point when I needed to expand the small dark transgender closet, I had always lived in. It all began with me having to accept who I really was and had much more to do than just expanding my closet for all the feminine clothes I was buying. I was making a huge lifestyle choice that I had spent way too long deciding to make. All of this moving things around in my life led me all the way to leaving my closet totally behind and looking for a transgender house to live in. I had taken my time (decades) to make my decision, and it occurred to me that I had taken too much time but by then there was nothing I could do about re-winding the clock. I took the good and lived on until I was able to carve out a new transfeminine life.

As I look back, it does not seem possible to me that I have come from the lost, lonely boy staring longingly at himself dressed as a girl in his closet’s mirror to the person I am today. But none of would have been possible had I not been able to embrace the help of several key ciswomen around me to make it happen. I wonder what would have become of me if I was not able to meet them. On the bright side, stepping out of my closet (as scary as it was) enabled me to meet all of them to start with. So, destiny was on my side as my life went full circle from a dark closet to the bright existence I live with my wife Liz now. I was just fortunate as my hunches that everything would work out if I stayed on my gender path. I just had the super strong hunches that they would.

Thanks very much to all of you who read and interact with my writings. All comments are always welcomed!

 

A Special Kind of Crazy

 

JJ Hart

In my youth and even later when I was struggling with my deep-seated gender issues, the thought entered my mind that I may just be a little crazy to think that way. I even went as far as telling others I was not the well-adjusted person they thought I was.

Looking back now, I think I was just preparing in my own way to tell others I met that I wanted to be a woman. Which I never did for decades when it became obvious to strangers I met at cross-dressing, transgender socials I went to that I wanted to be feminine, or I would not have been there.

The first time that I told anyone that I liked to wear women’s clothes was after a Halloween party I went to in the Army of all places. Weeks later, over way too much good German beer, the topic came up with friends about how realistic my “costume” was, all the way to my shaved legs. Since I was among a few very close friends, I took a big chance with risking the remainder of the time I had in the Army and told them I was a transvestite (the term used back then) and I liked to dress as a woman. I said nothing about being crazy, and I just liked to do it.

Of course, at that time in my life, I was busy running from the fact of how deep my gender issues went. I was hiding the fact from myself that no I was not crazy, I just wanted to be a transgender woman in the days when the term was first being used. “Running” for me back in those days meant changing jobs and locations frequently to keep my mind off what I was truly running from, my gender issues. Even with all the moves I was making, I could not outrun my life and occasionally the term “crazy” snuck into my thought pattern.

To compensate, I began to do “chores” which I considered feminine in nature such as doing part of the grocery shopping for my wife dressed as a ciswoman. When I succeeded with no problems, I started to feel so natural that I continually wanted to do more. So, I began to combine my grocery shopping adventures with new visits to big shopping stores to pick up small items I could afford such as a pair of panty hose, or new makeup. Amazingly, no one bothered me or shouted, “There is that crazy man in a dress.”

As the years went by, I learned that the ciswomen around me did not think I was crazy. They thought I was more curious than anything else as they wondered why I would leave the men’s club to play in their world. Ironically, as they were taking care of their curiosity, at the same time, I was learning from them. I had always envied girls (then women) so much as I followed them from afar, and now I had the chance to go back behind the gender curtain and learn first hand about the pluses and negatives of a ciswoman’s life and did I want to be a part of it or was I just following a crazy path off a cliff.

I learned quickly that I was following the right path, no matter how crazy it seemed at the time. The more I explored the world as a trans woman, I found the more exploration I needed to do but that was OK with me because again, my life for a change did not feel forced and so natural because I was not fighting to be something I was not…a man. All of a sudden, my life made sense and a was a special kind of crazy, a transfeminine person. At that point, I knew I would have to lose for good all the formidable white male privileges I had earned over the years. Even I was surprised to say “buh-bye” to all privilege I had built up.

Not all benefits I had living as a man were so easy to give up such as part of my intelligence and my personal security. I did not have many interactions with men one on one, but I learned the process of letting the man take the lead in most all situations. Especially when it came to sports, where I knew a lot about what was going on. The other privilege or benefit I needed to give up quickly was when it came to my personal security. I was not prepared for the world I was facing now in which I was fair game for any toxic man. I was fortunate to have escaped injury a couple of times when I broke the rules that ciswomen grow up with such as not finding your self in a compromising position on a dark city street all alone. I thought at the time, I was crazy to do it and never did it again.

Most recently, the craziest thing I have done is to let my precious Estradiol prescription run nearly all the way out. In fact, I am down to my last applications of patches this week as I am waiting for another refill which I have been notified is coming today. I have written in the past a couple of times about the paranoia I felt when I had a recent appointment with my endocrinologist who prescribes my HRT medications. It turned out that that all my crazy paranoia about the far reach of the orange felon in the White House rejecting any ideas of me receiving gender affirming care through the Veterans Administration would ever happen again. Instead, I received a prescription which will last me through another year until our next appointment.

Once again, it was proven that I am a special kind of crazy which I wish I had learned to embrace earlier in life. It would have made life so much richer just knowing I had the chance to experience life on both sides of the binary gender border.

 

 

 

 

 

Courage or Something Else?

 

Image from Miquel Bruna
on UnSplash. 

Recently, I have exchanged a few comments with a reader named “Janie” and we somehow got into the subject of being courageous in our male to female gender transitions. Also, on occasion, I get someone calling me courageous on how I decided to follow my path to leading a transfeminine life.

The problem is I never considered myself courageous as I tried and tried to establish myself where I could blend in, in a world of ciswomen everywhere. Here are two examples, the first coming from “Janie.” When she said she wished she had the courage (and I am paraphrasing) to come out as a full-fledged transgender woman as a teenager. On the other hand, I wished I would have had the courage to follow my instincts and come out of my closet when I was honorably discharged from the Army and had very little male baggage to think about. I was still becoming established in the working world, had no children yet and a future wife who did not seem to care what I did. I would never again have that sort of opportunity to live a life as my authentic self without waiting on the world to catch up.

It turned out that I still had a lot of living to do before I could find my way up my path to being a fulfilled transgender woman. Sure, there were plenty of opportunities to overcome when I was petrified to try to overcome my male self and enter the world of women, but I never thought I needed an extraordinary amount of courage to do it. I always reserved that amount of praise for war heroes and first responders who ran towards danger, not away from it. I was not running towards danger; I was just doing what I had to do to survive.

Ironically, the world evolved around me when it came to gender issues over the years. You may remember when the film “Tootsie” came out and gave a realistic idea of what ciswomen go through in the world through the ideas of a man (Dustin Hoffman) living the experience. Sadly, the new look into the genders did not last until today when coming out into the world possibly did take a lot of courage after all. Lives could be wrecked when you would not be fully accepted as a trans woman with your spouse, your family, your friends and your employment. Especially today when the orange Russian asset in Washington DC is leading the charge against us for no real reason.

Getting back to the task at hand, the something else when it came to the courage question, as I said, came down to pure survival. Not some sort of a hobby of putting on a dress and makeup to attempt to look good as a woman. The problem was that I knew at a very early age just looking at my girlish image in the mirror was never going to be enough to satisfy my gender desires. I simply wanted more. To live like the girls around me I so envied in school. An idea which would come back to heavily influence my life in later years. I fought my feminine instincts hard, which ended up doing nothing more than potentially destroying my mental health and my life as I led a very self-destructive life. It seemed everything my male self-had built up, I needed to try to tear down. I would not have wished what I went through on my worst enemy. So, I set out to do what I could to save myself.

During those days of discovery, I learned firsthand the idea of having persistence over any idea of having courage. Survival became my goal in life as I set out to build a feminine lifestyle from scratch. Deep-down, the idea kept coming to me that I was doing the right thing, no matter how painful it might turn out to be. In fact, I went all the way back to my childhood, so I knew it was more than just a temporary rush of gender euphoria as a trans woman when I was accepted in the world. I was surviving as me with little or no courage needed. Just a liberal amount of fear on the occasions when things were not going so well like when I had the police called on me for using the restroom of my choice. It was my own fault for being in a redneck venue I had not taken the time to set up being a regular yet. Then I never had the courage to go back.

I will never try to speak for “Janie” or anyone else who regularly reads my work, but on my end, no matter how much I did not respect the work my male self-did for me over the years there are certain things I would have really missed if I had followed my instincts and come out before I had the chance to build any sort of a life. I would have missed the once in a lifetime opportunity to have a wonderful daughter and a loving wife which I was with for twenty-five years until her untimely death. We had many good times, interwoven with the bad caused by my gender issues. I don’t know if I would have ever had the courage to ever totally leave her and wished she could have been around to experience my growth into a mature transgender woman. Of course, now, I will never find out.

As you can tell, I really don’t believe courage had that much to do with my development as a transfeminine person. On the other hand, a heavy dose of persistence mixed in with the ultimate need to survive allowed me to make it to where I am today. I know I am basically just dealing with semantics anyhow so the only thing that matters is how you survive. With or without HRT or any gender surgeries or with extensive work it does not matter as long as you are happy and thriving.

Thanks to “Janie”, Christine and all of you who have taken the time to comment on my topics. Without all your input, my work would not be worth it.

 

 

 

 

 

 

Stopping when You are Ahead

 

JJ Hart. Girls Night Out.
I am top left. 

Somehow, I never learned to stop when I was ahead when I was growing up. Or, as my parents always said, I tried when I was given an inch, I always tried to take a mile.

That whole idea really manifested itself when I began to explore my gender desires and start to cross-dress in my mom’s clothes. As I perceived myself to be successful with one new look, I always wanted more very soon. I could not stop when I was ahead and kept on pushing the boundaries of danger when I cross-dressed at home in the bathroom. Even if my brother was home too. I was risking what I had of the young male life I thought I needed to protect.

Somehow, my guardian angel was looking over me as I never got caught as a kid with my cross-dressing activities and I simply wanted more than I could get most of the time such as a nice, fashionable wig. Rather than the Halloween store wigs I was stuck with. Due primarily to financial constraints. During this time of my life, I was stuck with just being able to dream of what my life could be like when I grew into a more complete transfeminine person. It turned out to be a long (decades) away from coming true. Take wigs for example. When I finally arrived at the point where I financially could afford it, I went overboard on haunting the local wig stores around me looking for just the right wig which I thought would be the perfect addition to my hair collection to allow me to present better in the world. As I did it, mostly all that I accomplished was acquiring quite the collection of potential drag clown wigs which I did not have the patience and/or knowledge to take care of.

At that point, I could not stop when I was ahead or behind my quest to be at least an attractive woman. Every time I experienced the least little bit of gender euphoria when I went out in public, it fired me up and encouraged me to do more. Unfortunately, that meant taking extra chances with my actions and ultimately my safety. I needed to learn the hard way what ciswomen were raised to know about not putting yourself into potentially dangerous situations. I barely lucked it out when I escaped situations with no harm to me, so I essentially did not have to stop when I was ahead as a trans woman. I just had to be wiser when my male privileges were stripped away such as the personal security privilege men inherently have.

As I emerged as a wiser novice transgender woman, the reality of what I was attempting set in and I could not stop. Even if I was ahead. I began to set up a stairstep approach to my male to female feminization process which would I hoped, give me a more in-depth look at a woman’s life behind the gender curtain. Which I had spent countless hours thinking about. I started to consider all the things I wanted to discover as a woman that I had dreamed of as a man which led me to set up my own transgender mental bucket list of things to do. Basically, I set up activities at levels of difficulty. So, when I accomplished one I did not have to stop and move to another. Using the women’s room was a prime example of sliding behind the gender curtain and using a women’s only space. I knew a little of what to expect from my days as a restaurant manager when I needed to monitor how the women’s room was kept for problems I could encounter. Not starting from scratch helped me to survive in my new world with cis women.

Fortunately, I spent much of my time in the world successfully as I learned the basics of how ciswomen live. By doing so, I simply could not quit and kept on trying new things. My bucket was quickly being worn out by the challenges I was facing. Mainly by meeting the number of women who showed interest in me. I have always thought they were just curious about what I was doing in their world and was I living my life the best I could in the girls’ club. In my case, I was different and hopefully presented the best of the two main binary gender worlds as I socialized with many different women who seemingly were happy to see me.

By this time in my life, I simply could not stop what I had started as far as chasing my femininization process. It involved doing a deep dive into how women communicate and compete with each other, among other important things. Probably, communication was the most difficult aspect of my transition to learn. For the first time in my life as a transwoman, I needed to listen closely and completely to what was being said to me for hidden meanings and nonverbal cues. Then, as far as competition as a woman was concerned, I needed to learn that women compete just as hard as men. Just on a whole different spectrum of passive aggressive actions and reactions. Believe me, I learned the hard way a number of times when I made the wrong move and needed to watch my back from a smiling face who was out to get me.

Once I succeeded in learning all of my feminine lessons, my confidence was at a all time high. Especially with the small group of lesbian friends I had build around me by sheer luck. They ended up protecting me during my fragile times I was learning the final ropes of what it would take to round myself out as a transgender woman. By this time, my inner self could take over after being buried all those years and end up running my life’s goal that she always had a hand in. After waiting all those decades to live, she no longer had to stop while she was ahead. She was home and I was a whole person.

 

 

 

My Gender Workbook was Blank

 

Image from Marcus Winkler
on UnSplash. 

Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook. Of course, the problem I had doing it was I had absolutely no help. No mother or peer group pressure to tell me if I was doing right from wrong when it came to cross-dressing myself as a girl or applying makeup.

Ironically (as I said in a recent post), knowing my mom the way I did she would have been against me shaving my legs and wearing makeup as early as I did as her secret daughter. I was only trying to get a head start on writing my own gender workbook and trying to catch up with all the girls around me who also were sneaking around wearing makeup and wearing panty hose.

It was fairly easy for me to make up my own workbook rules when it was just me and the mirror to deal with. No matter what I did as far as my feminine presentation was concerned was accepted by my mirror which kept lying to me and telling me I was a pretty girl. Which was much easier before I hit the curse of male puberty and all the changes my body was going through. I was seeing unwanted growth and angles while the girls I envied around me were getting curves. When I went to bed every night, I dreamed of my life being different but of course it never was. I would not get the curves I wanted until decades later in life when I was fortunate to have good health enough to be able to start HRT or gender affirming hormones.

There turned out to be tons of effort I needed to put into my workbook before I could arrive at the point where I could even think about starting hormones. The shortcuts I kept trying to make never seemed to work and usually got me in trouble. When I did find trouble by trying to do too much with poor fashion choices, finally I gained some sense, rewrote my gender workbook and went on to successfully try to blend in with the world of ciswomen as a transgender woman. Looking back, I think that page of my book had so many erase and start over marks that I could barely read it.

When I really began to get serious about seeing if I could be successful as a trans woman was when I desperately needed my gender workbook to help me, but it just couldn’t because I had not put the time and effort into filling it out. I had never given enough thought to how different the lives of men and women really were. Perhaps you remember the book “Men are from Mars and Women are from Venus” which when I read it, I wondered where trans people came from. I did not know yet we transgender women and transgender men get to occupy a special planet all our own with our unique knowledge of both men and women.

As I first began to mature into a more complete transfeminine person, I sometimes discovered my mental gender notes became overwhelming, and I needed to head back home to go over in my mind about what just happened to me. Good or bad, it did not matter. What was most unexpected to me was the amount of acceptance I received in the new world I was in. I had become used to the glares and abuse I took when I went out of the house in my early days and learned the majority of the world did not care about me one way or another. All the way to those other women who encouraged me to be in their world. Nowhere in my gender workbook did I ever imagine such a thing ever happening to a person like me just trying to find a new foothold in the world as my authentic self after all the years of struggling.

Sadly, there were still times when I ran out of ink to write in my gender workbook, and I attempted to purge everything I had accomplished and go totally back to my old safe male world. As most of us know, purges never work, and before I knew it I was out buying more feminine clothes and makeup to femininize myself all over again. By doing so, I finally came to the point of stopping obsessing over how I looked and settled into just being the person I was meant to be all along. I just did not want anything to do with me being a privileged male anymore, I just wanted to live out the long-held dream goal of mine to live as close as I could to a woman.

Even at that point, my gender workbook was different than other trans women friends I had known when I made the decision to live my life without all the major gender realignment surgeries and facial surgeries the others had gone through. I had two comments which described me the best when a transwoman friend of mine said I passed out of sheer willpower and another which came in on a comment and said I was just another old guy on hormones. Both were right in their own ways, and I wrote a mental note in my workbook that I would never be the prettiest woman in the room, but I could be the nicest. As far as the comment on me being an old guy on hormones, I wondered if the commenter was just jealous and it did not matter anyhow because I had always considered my gender to be between my ears and not between my legs and I had made it through life as far as I did with no surgeries at all, so there was no need to risk damage when I was older.

Also, I was fortunate to have been able to have other ciswomen around me help finish my gender workbook to where it is today. More than they ever knew, they taught me how to validate myself as a trans woman and welcomed me into their world. A major accomplishment in my life.

 

A More Innocent Time

 

Image from Arun Sharma
on UnSplash. 

On occasion, I look back at the early days of my cross-dressing past wistfully thinking those days were the innocent ones of my life before everything began to get more complicated.

In those days, all I needed to do was make sure I did not destroy mom’s pantyhose or stockings and be careful to put back her clothes where I found them. I guess I was successful because she never said anything to me. Using her makeup was much easier because she always kept samples in a side drawer in the bathroom, I could experiment with. At that time, the whole cross-dressing experience seemed to be an innocent game. Except for my deep paranoia about getting caught. Even the paranoia led me to being more creative about hiding my feminine clothes and makeup. What I had of it.

When the reality of serving in the military during the increasingly deadly Vietnam War slowly but surely made its way into my life, much of my innocence began to go away. The stark reality of going without my dresses and makeup for three years of my young life began to set in. After I passed my draft, medical exams and tests there was nothing I could do about it. Because I was not prepared to run to Canada to evade serving in the military. During that time as well as many years after I was honorably discharged from the Army, I continued to be quite naïve or innocent that all I needed to do to survive as a transgender woman in the world was to do my best to look really feminine. These were the days when my second wife and I battled back and forth about how I was cross dressing as a woman. She always thought my makeup was overdone and I was too fond of wearing “girly” fashion for her tastes. I tried to tone it down for the occasions we went out as two women but her expectations of me were so strict that if I followed her directions, I might as well not bother cross-dressing at all.

Even though I lost most of the battles with her about my evolving fashion sense, I won a few wars when she had to ask me for makeup guidance when we were going out to a fancier setting. Revenge was sweet. For a while, life was very routine for us as we both had challenging employment when we moved from our native Ohio to the suburbs of New York City, a real culture shock to us both. I was disappointed when the more liberal attitude I expected in the big city never materialized because we had to rent from an elderly Italian man and his wife who I knew would have never accepted a trans woman in their apartment. Long story short, my wife loved NYC while I disliked it and started my habit of rapidly changing jobs and moving to outrun my gender issues. Undoubtedly, I had entered one of the most exhaustive phases of my life as I tried to balance my growing transfeminine desires with a wife, a job and a family.

By this time, my growing one on one interactions with the public were driving what I had left of my innocence away. I began to realize that I was locked in a life-or-death gender struggle which may be impossible to ignore. What did I do? I exchanged my exhausting job changing for settling down in one great job opportunity, and at the same time begin to explore the new and exciting world of being a trans woman fulltime. For a time, I was fulfilled by both aspects of my new life until I began to be overwhelmed by the speed both my job and me being able to carve out a life as a new trans woman was coming together. I never imagined I would be so successful, and so terrified about what I would do about them together.

I like to refer to the process I was going through as trying to piece together a large, complex puzzle of life. On one hand, I had my male side loving the financial increases he was seeing. Then my female side pushing back to what was more important. Making money as an unhappy man or living a softer more fulfilling life as a transgender woman. Almost daily I struggled with finding the right pieces for my puzzle. All I accomplished was taking all the satisfaction I was feeling from either side as they battled on.

As I faced the new world I was living in, I was determined to be less self-destructive but that did not work either as I continued to do things like go to my restaurant competitors dressed as my authentic trans woman self. I was not that good, and it did not take long for the gossip to get out about what I was doing. Sabotaging all that I had worked so hard to achieve in my career to finally let people know who I really was. I was destroying once and for all my male past and the innocence was gone. However, with the loss of innocence came the deep feelings that I had finally made the right choice and everything I had done in life directly or indirectly had influenced my future. My primary example is fathering my daughter, who over the years has accepted me and I love very much. Without being forced into the Army where I met her mother, I would never have had the experience of my life. I am just fortunate that I was destined to live as long as I have to have the chance to see the pieces of my puzzle come together and have a chance to experience one of the most interesting and scary experiences a human can take. That of course is crossing the gender border from male to female to live on the other side.

I was never good with puzzles, especially my own, and to lose my innocence finishing mine was a real treat.

 

 

More Changes

 

Image from Brad Starkey 
on UnSplash.

More changes are coming to our house beginning today. Thanks to my wife Liz, we are tearing out one of our old bathtubs and putting in a new walk-in shower. Which is perfect for my immobile status and makes it less dangerous for me to take a shower.

You would think, by this time in my life, I would be used to change but it seems I have just become more set in my ways as a senior citizen transgender woman. As with many of you, our gender issues changed us for the first time quite early in life. Mine manifested itself the first time I felt the magic of trying on my mom’s clothes and I worked my way forward from there.

At that time, I labored under the impression my love for feminine clothes would eventually go away but it was something I ended up growing into rather than away from. The older I got, the more skilled I became at acquiring key items in my wardrobe and hiding them away in places even my younger brother would not find. I even increased the number of odd jobs I would do (such as a newspaper route) to augment my meager allowance and allowed me to buy items such as makeup and panty hose which felt so good on my legs I was shaving earlier than probably half the girls my age that were allowed to do. To shave them I had to use my mom’s electric shaver which I needed to carefully clean after every use. Again, somehow, I managed to escape detection as I continued to cross dress.

It wasn’t until my military days that I really began to push for more changes in how I was approaching my femininity. It was a Halloween party I went to when I only had about eight months left to serve that changed everything. For my “costume” I chose a slutty woman’s look to go with my friends looks. Further down the road, during a night of drinking fine German beer, my “costume” came up in a casual conversation with three of my closest friends, including my first wife. As we talked about the amount of time and effort to look the way I did, I finally thought to hell with it, and told the group I was a transvestite (the term of the day) and I liked to wear women’s clothing. Surprisingly, no one cared and life went on normally for me even after for the first time in my life I risked it all and told someone else my deepest darkest secret. I felt like a huge weight had been taken off my shoulders, but my freedom was fleeting because of what I did in the Army. If anyone of my higher ups had found out about my secret, it could have easily caused me to have be put up for a dishonorable discharge with less than the eight months I had left to go. Which would have been heartbreaking with all the changes the Army had put me through.

As I always write about, my newfound freedom to tell anyone else about my ongoing male to female femininization project came to a screeching halt when I tried to tell my mom. She rejected me totally and sent me scurrying back to my closet as far as telling any blood family about my potential transgender dreams. The only close person to me that I knew was my first wife and surprisingly her sister who told no one. I think sometimes by coming out the way I did at Halloween parties was a plea for the public to listen to me and when I did ever transition, no one would be surprised. Surprisingly, I was so macho in my male life, nobody ever did. Including the few people who were still alive years later when I came out. All I got was surprise from the people I knew. The main reaction was that I seemed too macho to ever be a woman. 

All the changes I went through as a novice transgender woman in my thirties and forties were immense as I learned what I was really facing if I followed my gender path to my ultimate goal of living fulltime as a trans woman. I kept being stopped by blind curves and huge Ohio potholes as I learned the hard way what ciswomen must go through to live their daily lives. I had become a social person later In life and desperately needed it to continue when I went behind the gender curtain and emerged a better person. I spent so many evenings planning to be by myself that the loneliness was really getting to me before changes suddenly began to set in. It all started when a bartender at one of the venues I visited often set me up to meet her lesbian mother to have a casual drink where she worked.

We became friends and were able to see each other often until another woman entered our little group and we became a friendly threesome and gathered to watch sports on the big screens. Of all things, the third woman was another lesbian who slid her phone number down the bar to me one night when I was alone and I responded feeling much better about myself.

The most amazing experience I had was yet to come when my future wife Liz responded to an online ad I placed. Predictably, I had to sort through the ton of online responses I received all the way to being stood up on pre-planned meetings with men I met online who I refused to not meet in public. I met Liz on the other hand in one of the sites where I was advertising in a “woman seeking woman” room and she responded to me and kept responding until we set up our first date midway between our homes which were approximately seventy-five miles apart. We went to a drag show then to a Renaissance Festival and fairly soon she invited me to move in with her. That was over twelve years ago, and I surely made the right decision.

With all this social success, I need to point out again how many dues I needed to pay before I was successful. I look at it as a full circle karma payback to all the lonely times I spent after my second wife died along with most of my closest friends. I had nowhere to turn for comfort and was forced to step out of my usual social conditions to look for connections. But that did lead me right back to the old big sports bars I so enjoyed and felt at home in as a man. Again, a full circle social moment. At least, the bartenders would socialize with me if I did not cause any trouble and tipped well. At that time in my life, any interaction was welcome as I went through the biggest changes in my life.

Change is a natural part of life anyway, but it seems we transgender women and transgender men have more than of our fair share of change to deal with. To be sure it is difficult as we pay our dues to live a life as our authentic selves.

 

 

 

 

 

I Always Was a Dreamer

 

JJ Hart

I always was a dreamer and a person who thought why not me if others could do it.

I guess it all started with the parents I had who were from the “greatest generation” or WWII and Great Depression survivors. Ironically, I was taught to think for myself as long as my thoughts did not conflict with theirs. That is why I could never tell anyone in my family of my dream to someday be a woman. I needed to fall back on my default answer that I wanted to be a doctor or lawyer which kept me out of the psychiatrist’s office.

My most difficult dreams were waking up when I was still male and my vision of being feminine was just that…a vision. I had only dreamed that I was the pretty girl I desperately wanted to be. It was then that I started to play the odds that I would not be caught wearing my mom’s makeup or dresses, or worse yet get caught shopping for my own makeup in a downtown store close to where my dad worked as a banker. As luck would have it, I managed to always be clean and dressed back into my unwanted male clothes by the time my parents or my only brother came home from wherever they had been. Even though I had been able to briefly help decrease the gender pressure I felt from cross-dressing, deep down I knew I had other urges and I began to dream of what I was ever going to do about them.

The first problem I had was I had little to no confidence in my ability to present as an attractive feminine being when I tried. I was fond of thinking I looked like a circus clown in drag. And I am sure I did before I was able to come to a basic understanding of how to use makeup. On most occasions, I could only dream of the time when I could look better as a girl in my mirror and I kept playing with the odds I would not be caught and ruin my whole future as I knew it.

The playing the odds attitude helped me considerably when it came time for me to serve in the military during the long drawn out and deadly Vietnam War. Rather than serve the basic two years if I was drafted, I could have a couple other choices such as enlisting for three years and attempting to get a job I wanted to do or even join the National Guard for six years and basically stay out of the war that way. As decision time approached, I made a split-second decision to turn down the guard offer and take the enlistment offer as I hoped I could get a job in the Army that I really wanted. Which was I really wanted to continue my radio DJ career in the military which was nearly impossible to do as the Army only had sixty broadcasters in their entire system. I played with the odds and won and the three years I spent serving my country turned out to be very beneficial to me as I got exactly what I wanted. A slot in the American Forces Radio and Television Service in Thailand, then Germany.

My success in my near to impossible military profession taught me that perhaps I could be successful in my transgender dreams also. Nothing might be impossible if I only kept trying and refused to stop during my gender journey. I was naïve, which was probably for the best because I had no idea of all the stop signs, I would continue to face before I was allowed to play in the girl’s sandbox. I always knew women led a more layered, nuanced existences than men, but I didn’t know how much more different I would have it as a transfeminine person until I tried.

I knew when I started to become successful in my dream to live in a world full of competitive ciswomen, my ultimate goal might have been within reach. My presentation in the world as a trans woman was benefitted from all those frustrating hours, I spent experimenting with makeup when I was younger. The next challenges turned out to be the most difficult ones when the world (primarily ciswomen) wanted to challenge me with their curiosity about what I was doing in their world. I discovered what I already knew from my past that whatever did not kill me just made me stronger from the rare negative interactions I had with other women. I was able to learn valuable lessons on how to look for passive aggressive disagreements and recover along with the claw marks up and down my back.

Another positive was that I rarely had a wishful dream that I was a woman anymore. My feminine dreams just went to the shallow extent of showing me how my life would be if I was more attractive or had the chance of not missing all the days of growing up in the world as the girl I always knew I was. Plus, I knew I must be doing something right because none of my feminine dreams turned out to be nightmares in the real world.

In addition to wondering what my second wife would think of me now as a trans woman who has had a decade or so to fill out her gender workbook, I wonder if my parents would have ever come to accept me either. Or at least recognize the mental seeds they planted in their oldest son who turned out to be their oldest daughter after all. Somehow, the irony is not lost on me how such rigid parents could raise such a child who turned out to be such a dreamer. Somehow, I believe my dad who was a self-made successful man would have come to accept me long before my mom who I tried to come out to and was rejected years before.

Even then, she could not break my spirit or my dreams.