Too Low on the Down Low

 

Image from Ky Nang
on UnSplash. 

I describe my life when I was cheating on my second wife with another woman(me) as being on the down low. Especially when in the early days I was hanging out in gay bars.

On occasion, I feel as if I make the process of transitioning with or without my wife’s support a little too exciting or even fun. I need to make it clear; it was anything but. It all started with a deal my wife and I made which I could go out in the public as a woman, only if I did not do it from our house. I even went as far as renting out motel rooms to apply my wardrobe, makeup and hair as I got ready to go out into the world.

Of course, with my mentality, that was never enough, and I started to break our agreement to never go out cross dressed from the house. The more I did it, the more I wanted to do it. That is when the going on the down low really started as I was sneaking around behind her back as a novice transgender woman every chance I got. I was stuck in life between not breaking our agreement and feeling so natural every time I went out in the world. During my life, I had always prided myself on being very honest, so I was not happy with the way my life was headed when I needed to lie to my wife when it came to explaining what I was doing in my spare time. Or why I was not successful in removing all my makeup when she came home.

The next biggest problem I ran into when I was on the down low was what was I going to do about the women who were approaching me. It was not as if I was being bombarded with romantic advances, but I did have some slight pushes. I felt bad because I never had any intention of ever physically cheating on my wife. However, I had always been a bit of a flirt which carried over from my days of being a male. There were occasions such as the night a man tried to pick me up in a bar after a professional makeover that I wonder what would have happened had I stayed. I didn’t and I will never know as well as what would have happened had I pushed a little harder to get to know a certain man with a motorcycle I was becoming close to.

I guess I had reached the bottom of my down low except for some stolen kisses from my lesbian friends. I internalized my feelings and waited for them to come to me, just like my male days. Then, when my wife unexpectedly passed away, everything changed and at the least I had purged my feminine life the best I could for the last six months of her life as I did not want to lie to her anymore. After she passed, all my barriers were removed and the first thing I needed to do was determine my sexuality. I thought to do it; I needed to go on public safe dates with a couple men I had met. I had a great time with Bob who was passing through Dayton on business, but he was married and lived far away. I did not have to worry about being brought home to mom in our brief relationship.

On the lesbian side of my life, things were decidedly different since I was no longer on the down low. Since HRT had effectively did away with any masculine sexual advances, I needed to learn new techniques. If I was brave enough, I found with the lesbian culture I needed to move slow and let them make the first move. I basically ended up with a group of three women I was close to. Which was all I needed. From the three, Nikki was never a real possibility because she was too much younger than me and I think would have recoiled at the idea of ever having relations with any sort of men (including me) at all. She was just an entertaining drinking buddy. Kim and my future wife Liz were in totally different situations. Both had lived difficult lives and were closer to me in age so they could relate to me being in a rebounding situation from all the death I had went through. In the end, I decided to move in with Liz in Cincinnati and are still together over a decade later, so I made the right move. Although every now and then I hear from Kim.

One way or another, life on the down low was never any fun for me. I constantly felt as if I was cheating on my wife. It was a relief to finally let it go and live my life authentically as a transfeminine person.

 

A Tale of Contrasts

 

Image from UnSplash.

No matter how you cut it, our gender is a tale of contrasts.

From the earliest age, we are forced into rigid gender roles, who for most people, work out quite nicely because they never question their assigned roles. Then there are those of us who just as early in life begin to question our placement on the gender spectrum. In my case, I knew something was wrong, I just could not figure out what. Then, as I became older, I made the discovery every morning when I had to determine what gender I had to be for the day. A jarring discovery to be sure.

Naturally, since I was born male, I needed to own up to the fact I had to do my best to face the world each day as a guy until I could slip behind my own gender curtain and put on women’s clothes and makeup. Early on, as I lived my limited feminine life in the mirror, I thought appearance was my number one goal towards living my gender dreams. It was not until much later in life did, I began to understand how wrong I was. There were many more contrasts between men and women that I ever dared to think about. Mainly because I was viewing how women live only through rose colored glasses as I thought they had easier lives than men.

It wasn’t until I began to pay my gender dues as a transfeminine person, did I begin to see the reality of what I was looking at if I decided to transition. As I was making my way into what I call the girl’s sandbox, I was getting tested regularly to see if I belonged. On some days I was successful and happy and on others, I was getting beat up (or clawed) and needed to retreat before I came back for more. One thing was for sure, all of this testing from other women was doing me good, because I never quit trying.

The main thing I did learn was one that I vaguely knew, women had their own world away from men and had their own alpha’s who ran the show. Once I was accepted by them, the rest of my life as a transgender woman was so much easier. But, on the other hand, the testing process was so much harder because the alphas were so much more wary of me wanting to be in their world. My second wife was an alpha and she made sure I worked long and hard to even try to earn a spot in the sandbox. An example was one of the many times she told me there was so much more to being a woman than just looking like one and it took me years to understand what she meant.

Perhaps the second most difficult part of being accepted in the feminine world was being able to communicate with other women. Out were the days of trying to bluster my way through a conversation and in were the days when I needed to look another woman in the eye and appear to be less threatening. While at the same time having eyes on my back for a passive aggressive attack. I learned the hard away on that to never trust a smiling face completely.

As I learned to communicate with other women, my life in public became so much easier and I could begin to relax more as I was beginning to put my entire feminine picture into focus. I could forget about completely focusing on my looks and movement and could concentrate on being social with the world. Which was important to me since I had always been a socially active person. Plus, as I always mention, men were never much of a factor to me since most of them ran and hid from me completely. Which was OK since I did not really know how to handle them as a transgender woman either.

My life of contrasts was coming to an end when I entered the final chapter with gender affirming hormones or HRT. The hormones were magical when they started their changes on me. I think most people consider external changes such as skin, breasts and hair to be important, and they are but to me, internal changes were more important. In a remarkable short span of time, I became more emotional as my world softened. Making me into a complete person.

I am biased, but I think my tale of contrasts made me into a better human being as I could understand both binary genders better. Since I had lived in both. Plus, after having the chance to live as both, I made the right choice to live as a transgender woman, even though at times, it was an intensely lonely and difficult journey. Which could be another blog post.

Who "Ya" Going to Call?

 

Image from Beth Macdonald on UnSplash. 

For many cross dressers or transgender women, our gender pursuits are very lonely. If you are of a certain age, you remember lonely with a capital “L”.

You remember the pre-internet and social media days when any information on being a transvestite or transsexual was very difficult to come by. This is where I always mention Virginia Prince and her Transvestia publication and how it brought a sliver of light and hope into my dark closet. Virginia was all I had; there was no one else to call. My gender workbook was blank.

From the pages of Tranvestia, I learned of the nearby mixers I could attend and for the first time in my life meet likeminded individuals. I was naïve and thought I could meet others I could call and or meet on a regular basis. Instead, I met many people I did not understand and did not want to socialize with. Either I was too much of a woman for them, or not enough it seemed. I was caught in sort of a “Goldilocks” zone with a blond wig and still no friends to socialize with.  I selfishly wanted someone just like me on the gender spectrum.

Slowly, all of that began to change when I started to attend diverse gender mixers in nearby Columbus, Ohio. I started to come out of my shell a bit and began to meet others who I enjoyed their company which was a great start to finding my way out of the “who ya going to call syndrome”. From parties I was invited to, I actually had people I could call and be invited to come along to excursions such as the Andy Warhol main exhibit at The Ohio State University followed by a visit to a well-known Columbus gay venue I had never been to. I had a great time.

Of course, when I did begin to get out more in the world with or without my new transgender friends, I wanted more. Which left me in a really bad spot with my second wife and my male self who were increasingly putting up resistance to every move I was making. In my own mind, for the first time in my life, I was making progress towards learning if a transgender future was possible. Every step I took was resisted as the other two wanted nothing to do with my progress.

As I continued with building my own confidence as a transfeminine person, my circle of friends began to increase also. I was coming full circle into my own as I was the one setting up our social events and I even quit going to any other mixer in Columbus. Saving my time and money for the monthly lesbian mixers I so enjoyed in Dayton, Ohio. The only problems I still had were coming from my second wife who I loved very much and my male self who kept whispering in my ear was I doing the right thing by just giving all my male privilege away. I did my best to stay in the middle of the gender road while not getting hit by oncoming traffic.

Ironically, I had built such a good wall between my gender selves with my friends, I could not talk to them either. A prime example came when I tried to explain my first hot flash to a good lesbian friend of mine and all she said was welcome to her world. Lesson learned. From then on, I let her take the lead when the conversations became very personal because I knew she had a lot going on in her life, and at least I could be a good sounding board or listener.

I adjusted from moving from the very few male friends I had who had passed away to a very few new women friends who helped me to escape the severe loneliness I was feeling when my wife passed away. In ways they never knew, I was calling a friend and having the best of both worlds. I had reached my own “Goldilocks” zone as my friends were easing my solitude while at the same time, teaching me what it meant to be a woman. Primarily a woman who did not need the validation of a man to feel good about herself. Which was a direct conflict from the old ways of going through genital realignment surgery and then disappearing just to resurface in a new life with a man.

What was left of my sexuality after HRT remained with my lifelong admiration of women, so I did not have to change, which was a welcome discovery. Now, I am so fortunate to live with and have married the only person I need when I am feeling down or even gender dysphoric. I can talk it out with my wife Liz, and she is like I have my own in-house therapist. My problem is opening up after all these decades of closing myself off to the world. I was very good at the job.

 

 

 

 

Creating a New Life

 

JJ Hart, Club Diversity, Columbus, Ohio

As transgender women, we have a unique method of creating a new life.

Obviously, we cannot host a birth ourselves, so we do the next best thing, allowing our inner feminine selves to flourish in the world. For some of us, the process takes a long time. I was referring to myself as a late in life transitioner. Occasionally, I still receive the comment I was not transgender enough to transition. Or why did I wait so long. Comments such as those used to bother me until I grew confident enough in myself to ignore them. We all have our own path to creating a new life. How we get there, and our methods are our own business.

What is lost on most civilians is how difficult it is as we create a new life. Which is even more difficult because we are only bringing out what was always there. It took me decades to discover I had all my gender issues backwards. Life became easier for me when I learned I was a woman all along, cross dressing as a man. As with many or all of you, I set out to convince others of my true self.

At first, I needed to prove to strangers I was so much more than a man putting on a dress parttime or a drag queen in my days of hanging out in gay venues. It was not until I began to leave my comfortable closet and take on the straight world, did I begin to improve my confidence and overall presentation. As I went out, I took my bumps and bruises and invested heavily in my future as a transgender woman. I finally learned it was time to cash in my gender chips and go for it all. Each chip was a unique experience I learned from as I learned how to create my new life.

When I had started to test out the ciswomen gatekeepers and was accepted, I knew I had reached the now or never stage of my life. It was time to face my true inner self and live my truth. The secret of making my trip personal was a scary step. I needed to risk strangers taking advantage of me, or my emotions which had been badly damaged after the death of my second wife. I thought I had effectively shielded myself off to the world as a novice transgender woman, but the opposite happened.

As women have a way of doing, they read the true damaged me and a select few reached out. The main one was my wife Liz who I have been with well over a decade now. Just when I was hopelessly online seeking a date with another woman, she responded to me, and we started to communicate back and forth. Liz, as well as my daughter, were instrumental in me creating a new life. They were powerful feminine role models who I could (and can) fall back on to this day.

In many ways, I could resent being born with gender issues as a problem I did not need, but what good would that do. I would never have had the chance to look deep inside me and create a new life which started with hidden glances in the mirror and morphed into a full-time life as a transfeminine person. I would never have thought it possible.

 

 

Writing your Own Script

 

Image from Prophsee Journals
on UnSplash. 

I never found it easy to write my own script.

Sure, I could blame my gender issues on my problems but not all. I discovered very early in life I did not possess many of the dominate male traits to be a complete success as a man, so where was I to go. For example, I could not blame my lack of athletic prowess on my being a cross dresser. I was just not that good of an athlete. When I was on the football team, I wanted to be a cheerleader. They seemed to be having all the fun while I was getting beat up by a faster and stronger opponent.

Rather than setting out to write a new script as a cross dresser or young transgender girl, I internalized my script which turned out to be the worst move of all. I had nowhere to go or no one to turn to for help with writing my girl’s workbook. No sleepovers with other girls my age for ideas of how to be feminine.

I was stuck. I could not live either life I was in. I made a less than adequate male as well as a cross dresser who had nowhere to go in public. Plus, it would be years before I could go out of my closet and test the world. Once I did, I was very much a dismal failure. My earliest attempts at Halloween glory ended up with compliments on my legs but not much else, and the biggest problem was I needed to wait a whole other year before I could escape my gender closet again. I kept dropping my pen when I was trying to write. All I really knew was I was a male by default. Having been born into a gender I never liked.

On the rare nights I was able to escape and sample the public, often I could not read or follow the notes I had hastily scribbled down. And another problem I had was I was making a deep dive into being a transfeminine person so rarely, I could not remember what I was doing right or wrong. Even still, I did the best I could as I still obsessed with the brief moments of gender euphoria I experienced. Occasionally, I could see my gender dream was possible and I kept on writing. Chapters began to appear such as presenting as a woman with confidence and communicating with the world as a new me.

I was pleasantly surprised when I could read and react to the new chapters and attempt to keep them from invading my everyday life. It was impossible for me to walk around the majority of the time wondering how it would be to experience the world as a transgender woman. I was never good at self-control, and it was showing if I was not careful. Primarily with my wife who knew I was in my gender zone and resented it for the most part. She was too smart to listen to or believe my excuses about what I was really thinking about. As time moved onward, I became better at hiding my writing from her. Or so I thought. In reality, she saw our life slipping away to another woman (me) she could not control. In return, I resented her for being a strict feminine gatekeeper who would rarely let me behind her gender curtain by telling me I was not ready.

She was right. I was not ready at that time, but I was gaining fast regardless of her misgivings. In the midst of many ill-advised moves which jeopardized our long term, twenty-five-year marriage, I was making other moves which were proving I could make it to my lifelong dream of living as a transgender woman. More importantly, I was reading my writing clearly and the results felt so natural.

I also discovered writing your own script could be very messy and selfish to do. Many times, my wife and my male self-ganged up on me with fear tactics on what could happen if I transitioned. Many fights later, I finally prevailed by default when she unexpectedly passed away, leaving me alone with my writings. I cleaned up my mess and prepared to live out the rest of my life as a full-time transgender woman.

I think my lifetime of experience writing a new gender workbook for myself proved to be a worthy accomplishment. Once I understood where it was coming from. There was nothing wrong with me as I learned to navigate a new world I was just getting used too. It just took me awhile to catch up with the rest of the cisgender women who had a head start on me. I just achieved my womanhood from another path which is the topic of another blog post altogether.

 

 

Staring off The Cliff

 

Image from Anton Luk
on UnSplash 

When I reached a point where I saw the real possibility I could live a life of a transgender woman, I found myself staring off a deep gender cliff.

The biggest problem I had was wondering how I would land if I threw caution to the wind and become (as my second wife called it) man enough to be a woman. As I slid down the slippery slope towards my cliff, sometimes I was fearless and other times scared to death. I can’t tell you the number of times I sat in my car adjusting my hair and makeup before I went into a venue. At times, I considered bringing an oxygen tank along in case I hyper ventilated. I did not because I thought it would ruin my outfit.

Another problem I encountered was alcohol. When I drank, I became much more fearless but to get to my arrival, I needed to be brave and walk into a venue to order a drink. It took me awhile to put the alcohol in my rear-view mirror and get on with my life, but I did it.

Along the way, I cannot stress enough about all the bumps and bruises I had when I slid down a very slippery gender slope towards a very steep cliff. I was facing losing everything I knew, owned and loved to be a transgender woman, so I wanted to make sure I was doing my slide right. For the most part, I did good except for impromptu visits from the police after I used the rest room of my choice and another night when I was asked to leave a venue after I was doing absolutely nothing wrong. I mended faster than I thought I would and chalked the experiences up to what I needed to go through to transition in the straight world which I was trying out for the first time.

The main thing which kept me going was the deep feeling I had I was doing the right thing. I had spent too long in front of a lonely mirror to turn back then. I needed to face the cliff and decide how and when I was going to jump because it was becoming increasingly evident to me, I would need to.

After my second wife passed away, I went into another lonely dark period of my life when the only thing I did was go out in the world as a transfeminine person and watch the occasional sporting event with my brother as my old male self. What did happen was, I felt the time I was spending as a man was being increasingly wasted. Even my male self was seeing the beginning of the end to his life.  If my brother did not accept me (which he did not), he would have to go away.

What really helped me to overcome my fear of the gender cliff I was looking at, were the ciswomen friends I was developing. The give and take I felt when I was invited to girls’ nights out or even lesbian mixers was propelling me forward to making the ultimate choice in my life. Ultimately, I started gender affirming hormones under a doctor’s care and made my decision to jump off the cliff even easier to do.

It turned out, my women friends knew me better than I knew myself. They saw no traces of my old male self and helped me with the nuances of living in a feminine world. Many times, all I was doing was going along for the ride. Never had I ever experienced so much about a new world I desperately wanted to be a part of in my life. It all made my fear of jumping off my gender cliff so much easier.

Another example would be, I had taken the time to do my homework and build a solid base before the slippery slope claimed me. I waited for two extra years working at a job I hated to make sure I could retire on Social Security and not have to worry about transitioning on the job. During that time, my gender universe opened a little more when the Veterans Administration health care program I was in approved gender hormone therapy for veterans which gave me access to mental health care and cheaper medications.

It all turned out to be time well spent and came back to help me when I finally made the jump down my gender cliff. My experiences and friends made the landing so much easier. I ended up wondering why I had waited so long doing my preparation.

 

Living the Transgender Reality

 

Image from Brian Kyed
on UnSplash. 

For me, living a life as a transgender woman was much different than my life as a cross dresser.

I mention it because of the comments I receive here mentioning those of you who may be on different phases of your gender journey and are on the gender balance beam. Such as regular reader “Michelle” who commented: That “gender balance beam” you described? God, it brought me back. The confusion, the hope, the guilt, the not-knowing—all of it. And the way you talk about HRT, how your body just... knew? That hit me so hard. I’m still early in my journey, but reading stories like yours gives me hope that it can work out. Even if it’s messy and hard."

Thanks for the comment! Yes, somehow my body knew I had just made the right choice when I started gender affirming hormones under a doctor’s care. As far as the balance beam went, I have never been coordinated enough to stay on any sort of object, but somehow, I was able to stabilize myself several times and live a transfeminine reality.

Backtracking just a bit, this morning I read a thoughtful post on Stanas' Femulate blog which went into how women accept (or don’t) when their men come out to them as cross dressers. In my case, I write excessively on how my second and third wives interacted when confronted with my gender issues.

The entire interaction was a story of contrasts between the two women who never had the chance to meet when my second wife passed away. My second wife knew of my cross dressing before we were married, and it was never an issue for her. Although she never let on, she never liked the feminine version of me at all. The problem arose as it became increasingly evident, I was much more than your average cross dresser, as I increasingly slid towards my reality of being a transgender woman. The problems all of this gender turmoil created were never her fault. They were mine because I refused to face the reality of who I really was regardless of the costs.  She was well within her rights to refuse me any help as I moved towards my gender dream which would not include her, and I understood that.

Now, on to my third wife Liz. I have been with her for over a decade now. In many ways, she is the exact opposite of my second deceased wife. Liz met me online in a woman seeking woman chat room and rescued me from a very dark time in my life. I was falling off the balance beam. After many months of chatting back and forth, we decided to meet up for our first date with a couple of other women at a drag show.

At the time, I was still reluctant to finish my male to female gender transition. I was living a minimum amount of time as a man, and I had not started hormones yet. The reality of transitioning was still sinking in. After a few months of being around Liz, she told me she had never seen any male in me so what was I waiting for? All I needed to do was make a doctor’s appointment and start HRT and within a very short period of time move in with her in Cincinnati. So, I was able to make a clean start as a transgender woman.

As you can tell, during my life I have been blessed to be with several women who loved me and I learned from all three, including my first wife who I saw just last week as she is the mother of my only child. Even though she only knew me as a crossdresser, we still get along.

Any way you cut it, coming out to a woman you are in a relationship with is one of the most difficult realities of being a cross dresser or transgender woman. I think women who accept us are saints for putting up with such a unique set of challenges. What hurt me the most was my second wife agreeing to me becoming the best woman I could become then not liking the feminine person I was becoming. In all fairness to her, I did go through many changes in my reality when I transitioned and she passed away before meeting the true me. I doubt if there was any way we could have stayed together but maybe we could have been friends.

Maybe you can use the old marriage pun: Life is a bitch until you marry one. And change it around to being transgender is a bitch, until you become one. The truth of transgender reality?

 

 

Unlearning LIfe

 

JJ Hart

Over time, I spent so much time and effort unleashing my male past, I cannot remember it all.

As soon as I could think about myself, I knew something was wrong. I just did not know what. Primarily, I did not know I was trying my best to survive in a male world I wanted very little to do with. Perhaps the biggest problem came when it was time to unlearn all the male life I was forced into. I was the proverbial round peg in the square hole, and I did not like it, even though I was rewarded with white male privilege when I was successful.

By choice or not, it seemed I was always fighting myself or the world for my gender dreams or goals. Very early I knew somehow, I wanted to be a woman someday, a deep dark secret I needed to keep to myself. Overall, I was deeply conflicted about where my life would end up because it seemed as if I was on a runaway gender train I could not get off.

A prime example was when I entered male puberty. I watched in shock as my body grew angles, and I needed to walk like a man. I am sure I was a comical sight, but I tried. I did not want to be referred to as a sissy and bullied in school and I was successful. Until it was time to reverse it all. When I left the cross-dressing mirror and entered the world as a novice transgender woman, there was so much to do as I was busy unlearning my male life. First of all, there was that male walk I needed to get rid of. There was no way I could overcome the positive feminine presentation I had succeeded at doing, if I was going to continue to walk like a man. Plus, I had the challenge of doing it in heels.

When I learned to walk in heels, I learned the inherent power of female privilege. Suddenly, my legs looked better, and men paid closer attention to the clicking of my heels. I just needed to match the rest of my fashion to blend in with my shoes. Since I loved my boots, the first thing that I did was try to save up for a pair of nice, heeled boots and find them in my size. Thank goodness for Payless Shoes. For the most part, I did good in my heels except for the time I got a heel stuck in a sidewalk crack in a mall I was walking in and the time I fell on a wet spot in one of my regular venues I was in. I survived and learned I needed to be more comfortable.

Another major gender response I needed to unlearn was to always look another woman in the eye when I talked to her, especially in bathroom situations. Eye to eye contact was normal in women’s rooms and totally not in men’s rooms. The new rules of the “room” I needed to unlearn and relearn if I was to survive as a transfeminine person.

Another major point of contention I write about often, is the difference between male and female aggression. I needed to unlearn the old male aggressive ways of coming right at you. On the other hand, I was clawed many times when I failed to recognize the passive aggressive intentions of a woman I was dealing with. Often behind that smile was a sharp pair of claws waiting to take a shot at my back. I needed to keep my head on a swivel and always be careful when I was dealing with other women in the girl’s sandbox. Lesson learned and I moved on as a better transgender woman.

Finally, all these lessons began to come together in my life, and I started to become a whole human being again. But this time, a human I wanted to be. No more unwanted male who I still needed to fall back on in times of duress. Afterall, I had to live with him for nearly fifty years, so there was some good to remember. I found I could relate to both binary genders better and understand where they were coming from. Of course, men were the simpler of the two genders as I suspected and women were more complex, and they led more layered lives.

None of it mattered to me as my world opened in ways I never imagined. Going to the extreme of unlearning my old life was radical but then again, I was able to make it work in my own way. If you are searching, just be aware everyone’s journey is different but maybe you can make it too if you are careful. There are huge inherent problems when you decide to forsake your male privileges and enter a new gender world.

 

 

It's Just Life...Not a Joke

 

Image from Engin Akyurt on UnSplash.

It took me awhile before I finally came to the point in my gender transition when I gave up and thought the whole process was just life and not some sort of an evil joke.

I had struggled enough through the years when my male self-put up quite the struggle to exist at all. It was as if he was on a slippery slope towards losing his life altogether. To make matters worse as I always point out, my male side’s life was not always that bad. I had a long-term marriage, close friends and a good job to fall back on when I needed it.

Through it all, I thought it was only the draw of the feminine clothes which kept me longing for another trip to the mirror. I did not realize my feelings went much deeper than that. I was feeling life itself. It took me many years and even decades traveling a very curvy and bumpy gender path to realize where I was. Plus, many times, when I realized where I was, I became scared of losing everything. Falling off a gender cliff became a real possibility.

No matter how frightened I became, somehow, I kept on moving forward thanks mostly to the brief moments of gender euphoria I was feeling. The interludes helped me to determine if my dream goal of living a transfeminine life was possible at all. Back in those days, I was immersed in the struggle to present well as a woman and not much else. In fact, when I go back and read my earliest blog posts, I cannot believe how much they emphasize fashion and makeup. It all happened long before I needed to learn the layers of life a woman goes through to live her life. It was like my wife told me be man enough to be a woman. In those days I was not as I made weak attempts to live in both main binary genders.

In the short term, I did not understand what my wife meant as I became semi successful in presenting well in the world as a woman, but I had not paid my dues. I found I would have to wait until my wife had passed away before I could earn my way behind the feminine gender curtain to be allowed in by the ciswoman gatekeepers. It was about that time too when I began to understand my dream of ever becoming a fulltime transgender woman could be possible. It was much more than a hobby or part-time profession; it was my life. Then my realization led me to understand what my wife was talking about. I needed to set off on an all-out journey to live my best life as a transfeminine person. I even needed to understand questions about my own long held sexuality. If I lived as a woman, would I suddenly have to like men sexually? I just didn’t know until I set off to experiment.

Along the way, I did manage a couple dates with men which led to kissing but not much else and I did not feel much of a spark of any kind. On the other hand, I was surrounded by curious ciswomen (including lesbians) who wanted to socialize with me, so I was happy, I had always been a contradiction in terms socially, meaning I always enjoyed company even though I was shy and I could continue to feel that way. My life was beginning to come together in ways that I never imagined possible.

For example, I never imagined I would have been able to enjoy a small closely knit group of women friends who taught me more about life than they ever knew. Without any pressure, I was able to sit back and live vicariously through them and primarily how they lived their lives without the validation of men. It was not too long until they began to invite me along to their lesbian mixers, which I loved. I was even approached by other women and kissed. Which provided me with a huge amount of validation.

With my sexuality and life coming together, I could concentrate on enjoying my life on my new gender affirming hormones or HRT. The hormones went a long way in syncing up my internal and external self. Along with softening my skin and facial lines, my whole world was changing too. My emotions heightened as well as my senses as the world around me was softening. A perfect match to my rapidly expanding social life.

I will never know if waiting so long to transition into a feminine world was worth it or not because I had so many excuses why I never had done it. All I really know is, I did it before it was too late and have never looked back. That’s life.

 

 

At the Gender Crossroads

 

Image from Timelord on UnSplash

Many times, in my life, I have found myself at a gender crossroads.

Of course, like most of you, I learned from the situations I put myself into. As I always mention, the first one was when I needed to leave the comfort zone I had created with the mirror and attempt to live in the world as a transfeminine person. Initially, I was slapped down as people laughed and smirked at me. Until I learned to own who I was, which was a huge crossroad to negotiate.

Over the years, I began to think I had seen everything, but I had not. My main problem was I needed to make the final decision on which way I would go if I was faced with a making a final decision on which gender I would ever live as. Plus, I did not know if I even could live as a transgender woman. I kept searching and learning until I found I was not a man cross dressing as a woman; I was a woman cross dressing as a man.

I discovered also, I would need to transition more than once if I would ever try to make it to my dream life. Primarily when I learned it on the night I finally decided I would quit going out as a cross dresser and change my inner thought pattern. I was fed up with just trying to look like a woman and wanted to feel like one and see as if I could mingle with a group of ciswomen with no issues. I did make it with the other women and crossed another road I knew I could never go back. I mingled and socialized with other women and even used the women’s room with no pushback at all. It was amazing.

The next transition I need to make was when I needed to begin communicating with other women. It was never easy and a complete learning process. It does not take a genius to know women and men communicate on a different level. I knew well how to do it as a man, but I was a total novice as a woman. The first lesson I learned was I had to pause and listen to the other woman I was talking to. As a man, I could often make the first move and hope for the best. With women, I never did and often waited for a passive aggressive response. The real intent behind the smile often startled me until I caught on to the game.

All of it led me to the success I needed to this day to be successful with other women who indirectly try to bully me in their own way. An example was the ciswoman I wrote about in a recent post when she could not adjust to me being a parent not a dad to my daughter. In fact, I had a reader (Michelle) who responded to the woman and my return comment: “You handled it with so much more grace than I probably would’ve. And Liz’s quick response? Perfection. I’m so glad you still got to connect with your daughter and your grandchild, that’s what really matters. The rest is just noise.” Thanks for the comment! The woman was very noisy and was trying to bully me in her own way.

I was just fortunate that both Liz and I had been through similar situations, so we were ready. Somehow, the woman thought she had me over a gender barrel with the dad comment and that was when Liz took over. The woman asked Liz who I was to her and Liz said wife and the woman shut up.

My point it, both Liz and I had been through situations with other women such as her before, so we were able to handle the noise and go across yet another crossroad. By this time, I think there always will be another road to cross as I see my gender dream come together.

As Michelle said, the world is full of noise, and we must separate it into genders to make sense of it. Which would be another blog post altogether. In the meantime, for all of you approaching your own crossroads, try to feel secure on your journey and be careful. Especially these days when depending upon where you live transgender rights of any kind are in danger.

 

 

Just a Gender Detour

 

Image from Belinda Fewings
on UnSplash

After many years of looking back at my life, I began to think of my transgender experience as merely a detour in my life.

The problem was, there are many types of detours ranging from major closures to small delays. I found I needed to be careful with my navigation quite early when I was in the exploration stage of my mom’s clothes. One speed bump could lead me to an impromptu visit with a psychiatrist who knew nothing about gender issues and wanted to pronounce me mentally ill. Even back then, I knew I was not crazy for wanting to be a girl.

As the years progressed, I became increasingly skilled at sneaking around and dodging the detours in my life. Especially, the major ones such as becoming a parent. Even though the whole experience made me extremely proud, it still changed my life profoundly. I remember thinking at the time if it would affect my desire to be a woman but if anything, the birth process enhanced it. I was still in my detour mode, drinking heavily as I tried to find the nearest exit to help me.

To make up for the detours, I began to leave my closet and explore the world increasingly as a transfeminine person. The entire process meant taking chances such as leaving the house dressed as a woman and dodging many speed bumps along the way. It took me many more years before my path began to smooth out and I could see a clear road ahead. However, I still needed to be very careful with what I was doing. I had a long-term marriage and good job to protect among other male privileges. I was stuck between a giant rock and a hard place I needed to detour around. The rock was the better I did with my male life, and the hard place was my female side resented any incursion into her existence. To be sure, a very difficult place to be.

Then there were the times I crashed with my wife and was caught coming home late from one of my nightly gender adventures. A prime example was the night a lesbian was flirting with me and bought me a beer and said she should take me home with her. I was flattered and ended up staying too long and arriving home late. The ensuing fight lasted days after I hit that speed bump. Sadly, there were other times when I crashed on my own by driving an old sports car, which I bought that had the habit of suddenly not starting on occasion. Of course, one night when I was at a gay venue approximately twenty minutes from home, the car would not start. Fortunately, I had planned and left me enough time to call a tow truck and arrive home before my wife did. I had survived yet another close call.

My gender detours did not begin to go away until I started to really be allowed behind the gender curtain. It was after I had placed the gay venues firmly behind me in my rearview mirror and started to prove a fulltime life as a transgender woman was possible for me. The only problem was how fast I should dare to go. In those days, I still had my wife, family and job to worry about. As it turned out, destiny stepped in and showed me the way. Tragically my wife and several dear friends passed away leaving me alone to decide my future.  In addition, my road crew removed other detours such as employment when I discovered I could take my Social Security early and sell collectibles to make ends meet. My final indication I had a clear path ahead was when the Veterans’ Administration health care program approved gender affirming hormones for qualifying veterans. I was qualified and made a big jump towards my gender transition.

By this time, even I could see my detours towards living my dream were coming down, and I was in a now or never situation. I was sixty and had put up with my gender indecisions long enough. I went into a double retirement by quitting a job that I hated and gave away all my male clothes to charity.

Looking back, if I had known all the detours, I would have to take in my life just to survive, I wonder if I would have taken a different path. On the other hand, I was locked into a route I was taking and had no choice. Sure, I would have tried other ways around to get to where I was going. Such as attempting to come out quicker than I did and stop lying to myself. One way or another it is too late now to cry over spilled makeup.

 

 

 

 

 

 

 

 

 

When Being OK was not Good Enough

 

JJ Hart and wife Liz on right at Picnic.

I grew up in Ohio raised by greatest generation parents who lived through WWII and the great depression. Often, they were long on material support and short on emotional backing.

The main thing I remember from my childhood was, nothing was ever good enough. Take school for an example, while I excelled at subjects such as History and English, I really struggled with the Math and Sciences. Even still, I was expected to bring home straight A’s on my grade card every year. I had no excuses, especially when I went to high school where my mom was a teacher. She was pushing me hard for good grades to make it possible to get accepted by a good university.

I guess I became used to the pushing and figured nothing was ever good enough for myself and it carried over into my gender issues. Every time the mirror lied to me and said I was an attractive girl, I did not believe it and had to discover another way to prove it. Very quickly I learned I needed to replace the mirror with the public. Leaving my dark, lonely closet was the only way I could learn if I could ever achieve my dream of living a transfeminine life. It took every bit of courage I could muster to do it but if OK was not enough (by just standing in front of the mirror), I had to force myself into the world.

When I did force myself, it was like I was getting adjusted to a new pair of shoes. At first, I was tight and uncomfortable before I started to relax and began the basics of enjoying myself. I say I began the basics, because at every turn on my gender path, it seemed I was hitting a wall. Those were the times I needed to step back and decide if I was doing the right thing.

Those examples and failures proved to me I needed to keep going. Mainly because I felt so natural when I was pushing the envelope to leave my male self behind and live more and more as a transgender woman.

On occasion, proving OK was not enough and trashing the envelope almost got me into trouble. Mainly when I began to walk the fine line when I lost my male privileges. The most important being personal security. I was out and out lucky and escaped personal harm by men in the world. I wasn’t smart enough or experienced enough to sense the danger zones women are raised around. I learned quickly to park in well-lit areas or to ask for friends to walk me to my car. I did not want to be a statistic.

As I went through the process of living within the same parameter’s cisgender women have to face, I became a sponge of sorts. Nothing I did as I transitioned was ever good enough as my parents’ lessons oddly came back to help me. I was especially attentive when I went out to socialize with my women friends. They never realized what they did for me as I formed my own version of womanhood. In many ways I became a gender hybrid. It was impossible for me to leave decades of living an impacted male existence behind me, so I tried to take the good with me. For example, I was fortunate to have worked around women in the restaurant business for most of my life and I knew the trials and tribulations cisgender women faced in the world.

To this day, I have not shaken the idea of just being OK is just OK. I must be better just to be successful in the competitive world of women. I knew they could be competitive but not as much as I discovered when I finally had the chance to play in the girl’s sandbox. The whole process made me a better person in the long run, but it was surely difficult at times. Often brief moments of gender euphoria kept me going in my darkest gender hours. That was when I needed to provide electricity in my closet to give me the ability to see right from wrong.

Since my parents were my driving force behind my personality, I never had the chance to thank them for what they did. My Mom knew about my gender issues and chose to ignore them, and my dad never knew so I doubt if either would be pleased about their child raising outcome. They never knew how well OK was never enough worked out for me in my life.

 

 

What a Rush!!!

 

Vintage Transvestia Magazine

I encountered a real problem when my cross-dressing urges went from being a real adrenaline rush, all the way down to what I experience now.

I do remember the process did not take so long for me and I should have known then my cross-dressing activities were much more than a harmless innocent hobby I was involved with. If I had the information available to me then which became available later, I would have had an idea I was transgender. Of course, back in those days, the internet had not been invented along with all the social media rooms which came with it. I was in the dark ages of information and was very sure I was alone in the world with my gender desires. I always give credit to “Virginia Prince” and Transvestia Magazine for initially opening my closet door and showing me there were others in the world called transsexuals and transvestites.

During times of depression with my life, I could always fall back to my well-worn issues of Transvestia to lift my spirits. Plus, I discovered groups hosted transvestite mixers in Ohio I could attend with the proper preparation. I was ecstatic! I finally had a chance to meet others like me. Little did I know, I did not get that completely right, but that is another story all together.

In the meantime, I read my brief moments of adrenaline rushes were really called gender euphoria. Regardless of the label, I still had a difficult time controlling mine. Most of my examples come from the time my wife and I moved to the New York City metro area. For some reason, she left me out on my own one night to go to a mixer out on Long Island. Much to my surprise, I had a difficult time being admitted to the mixer by two cisgender women running the door. I asked why I was not being allowed in and they said no real women were allowed and I needed to show them an identification card with a male picture on it to get in. I was shocked and promptly showed them my old male drivers license and had a great time…until the buzz wore off days later. Then, I became mean and difficult to live with because I was feeling sorry for myself because I felt increasingly sure of myself as a transfeminine woman.

About that time, Halloween rolled around again which gave me an excuse to leave my closet and explore the world as a trans woman. This Halloween, I was getting better at “costuming” to present well as a woman and not to thrill as a cross dresser. Again, I was able to be out on my own because my wife was not a fan of Halloween and by pure chance, I ended up in the middle of a group of cisgender women all as tall as I was and dressed about the same way. Again, I had a great time and was even asked to dance by a man who I wondered knew about me.

All I knew was gender euphoria was great, until I crashed and burned. Then I always slipped back into my usual gender dysphoria problems. It seemed I needed the constant reassurance of me being able to present well as a transfeminine woman just to get by. Which was no way to live.

In order to live, I needed to make difficult life changing choices such as exploring the world increasingly as a feminine transgender person. I needed to weigh the difficulty in what I was doing with my life with what would happen if I was discovered. To accomplish my dream, I began to make small mini “bucket lists” of things I needed to do, most to just see if I could and increase my gender euphoria or adrenalin rush. Surprisingly, very quickly again my bucket lists did not provide much euphoria but in their place, a deep sense of stability in my life. For the first time in my life, I even felt I could be happy as a person. Whatever I was doing as a transfeminine woman, I was doing it right. Or so I thought.

Naturally I was afraid to make the final move to sever all ties with my male self. I found myself wasting precious time as I was able to expand my own new world as a woman of my own making. I had successfully gone through transitions from innocent cross dresser, all the way to full time transgender woman with bumps and bruises I had earned along the way. But I learned from them and moved on to a better life. If I only lived once, I wanted to live what was left as a woman.

Sure, my initial doses of adrenaline did help until everyday life came in and rescued me. Now I have smoothed out my life with fewer peaks and valleys of euphoria and when I do experience the negative gender dysphoria, I am able to live with it much better.

 

 

 

What Did I Miss?

 

JJ Hart at her first Girl's Night Out

Often, I am sad when I see a group of young girls playing. All too often, I wonder what I missed when I was growing up.

I then remember all the times in school when I was forced to play with the other boys and not join the girls’ group to learn what they were up to. Essentially what I missed was the chance to fill out my own gender workbook.

Since I believe women are socialized and not birthed, the early interactions of the girls robbed me of getting a head start towards my own unique womanhood. So, my gender workbook remained mostly blank for years, until I could claim the experiences, I needed to begin to fill it out.

Ironically, as I write about often, the greatest majority of my first interactions with the public came with other women. Then, I did have a chance to start to catch my gender workbook up as the other women indirectly (and directly) shared the pluses and setbacks of their times growing up and passing the gatekeepers into being treated as a woman, not just a female. At the time, I was so afraid of testing out the gatekeepers to see if I could be admitted that I never tried. Instead, I hid my desires, until I was sure I could make it. Still, it was very difficult to make it because of my continued shyness around strangers which was compounded by my transfeminine life. There just were not many like me in the world to pave the way.

As I began to pave the way, I needed to smooth out my journey. First, I had to figure out a way to properly dress my testosterone poisoned body so I could present well as a woman. To do so, I needed to become a regular at all the area thrift stores, as I shopped till I dropped for just the right fashion piece to add to my growing wardrobe. Once I did that, I could continue building my own path to maybe discover what I had missed not growing up as a young girl.

Surprisingly, as I began to be invited to special girls’ nights out, I began to learn I was not missing out as much as I thought. I discovered what I always had thought was true. Takeaway the talk of sports and business which men talk about and add in softer subjects such as family and friends, and I could indeed survive the new world I was in and not sit around like I was a hermit. I needed to hit a middle point of being interested in the conversation and adding in just the right amount of conversation. Such as, I found I could still talk about my daughter and grandchildren and still be relevant to the rest of the group.

What I was doing was skipping ahead in my workbook to sections which would include usage of the women’s restroom. I learned the importance of looking another woman in the eye when I met her because I could on the new side of the gender border I was on. My workbook said I could and should to survive and even thrive. I knew I had made it to some sort of a gender promised land when I was asked by other women to make the “sacred” journey to the rest room.

Even with all this happening, I was still frustrated by all the sections of my workbook which were blank. Deep down, I knew I could never reclaim the early years I had being forced into the male square hole I was in when I knew all along, I should have been in the round female hole. Perhaps the most frustrating part of the whole process was, the more I was forced into the male side, the more I was rewarded into acceptance. I refused to throw away my transfeminine workbook anyway and just hid it during times when I was forced into the Army during the Vietnam War.

For some reason, my workbook always resonated with me as I went through the down times. It was my shining light when I needed it to be. I just overcame the beginning chapters which were missing. My path to womanhood would just have to be different and in many cases more difficult than the average cisgender woman. I had to be better just to survive in a new world I was just learning about since I was not allowed to learn about it early in life. As I watched the other girls around me, often my jealousy grew because I never had the chance to wear pretty clothes or gossip with the other girls.

I learned my gender workbook was fragile too and could be changed or corrected at any time when I had misread certain situations. Which I write about often. I just stored the information away for use later. I am still adding to my workbook to this day.

 

 

Build the Plane before You Fly It.

 

Image from Miquel Angel
Hernadez on UnSplash. 

Early in my life I learned to build my gender plane before I tried to fly it.

When I was simply admiring myself in the mirror, life was easy, or so I thought. I could apply my makeup and put on my mini-skirt and journey to the mailbox, hoping the neighbors would not see me. Through it all, the mirror lied to me and said I looked wonderful even though I did not even have a wig. Even still, I kept going. Mainly because we lived in a very rural area and no one saw my mailbox adventures.

I suppose, during those days, I was merely experimenting with clothes and makeup, the same way any other young girl would do. The problem was, I had no one in my peer group to criticize me and help me to learn what was correct with make-up and fashion and it showed. I was attempting to fly my gender plane before it was fully built. The mirror never did any of it for me. It was simply there to tell me how good I looked.

It was not till much later in life, did I begin to replace the mirror with public feedback when it came to early adventures going out in the world as a transfeminine woman. I vividly remember all the nights I quickly returned home wiping the tears away after being followed by someone and laughed at. Mainly from teenaged girls. Somehow, I needed to keep taking my plane back to the drawing board to attempt to see what I was doing wrong. The good news is, I did begin to figure it out. I was dressing for the wrong gender. Trying to please men, when I should have been trying to please women. Out went the sleazy, ill-fitting clothes. Replaced by more sensible clothes as I did my best to cover my male poisoned body.

It worked as I began to blend into the world, as I gave myself the chance to experience my reality for a change. I was similar to the Wright Brothers during their first flights; I was not going far but I was doing it. During this time, my flights grew dramatically longer. I was finding my way out of the clothing stores where all they cared about was my money, all the way into restaurants where I had to interact with staff on a one-on-one basis. I was discovering how well my plane was built or not. Surely, I was still experiencing my ups and downs, but I was having more of the positive side of life.

The problem was, on my male side, he was still having success in his world with a very successful job. So, he wanted no part of helping to build a new gender plane. I was forced to build around him. Which made for a very shaky foundation. Especially for my already frail mental health. It hurt me deeply when I was flying high and he brought me back to earth with a crash. He even took me as far as an ill-fated suicide attempt.

In the short, and long term, I survived him and continued to build my plane, every time I thought I was done, there was more to do as I studied the nuances of living a transfeminine life. Adjusting to being passive aggressive alone to other women was a big adjustment, not to mention the communication issues I faced in the new world I was in. Other women were very curious about me and wanted to know what I was doing in their world. Very soon, my air space became very crowded with new people, mostly all women.

Many times, starting all over in life became a major challenge for me. I needed my plane to provide me with a better view of what was really happening in my life. I had too many fake, mean people to beware of. Even after all these years, my plane was still very fragile. Before I moved ahead any further, I just had to build in the inner strength I needed to pursue my dream of living fulltime as a transgender woman.

To accomplish my dream, I needed the friends I had found in my new life to do it. I always mention the Liz’s, Kim’s and Nicki’s of the world who helped more than they ever knew. It was all of them who finished building my plane more than I did and I will be forever grateful for them coming together to save me.

Growing up, I built plenty of model cars to look at and even race, but nothing helped me to prepare for the greatest building experience of my life. A gender transformation project which took me decades to complete. In fact, I am still working on it to this day even though I have been fully out for over a decade now. There was more building than I ever thought possible to start all over again with my life.

 

Catching Up

 

JJ Hart, Hot Summer Day.

This morning was a day to catch up and run errands.

Because of the continuing heatwave we are under here in Southwestern Ohio, I needed to get an early start. For example, it is nearly ninety degrees (F) before eleven AM with heavy humidity. So, by early I meant the pharmacy I was going to did not open till nine o clock. Plenty of time for me to have a leisurely morning as I got ready. By getting ready, I did not mean I had to go to any elaborate means to do it. Basically, all I needed to do was shave closely, apply moisturizer, makeup and brush my hair. I figured the least which would happen to me was I would see two different people in drive thru’s.

Of course, I was wrong because my second stop involved an up close and personal interaction with a coffee shop employee who was taking orders outside the window since the equipment had broken down in the heat. It turned out all my built-in paranoia of meeting strangers was unfounded for at least today.

First, the guy at the pharmacy had the personality of a cardboard box and could have cared less about me. And, as far as the girl I interacted with personally with the second drive thru went, she was very nice to me, and I felt as if I was welcome.  Especially since she knew I (assumed) I was transgender. Whatever the case, I felt good as I headed home before the traffic became worse again.

Speaking of going out, my wife Liz and I’s trip up to Dayton, Ohio during the upcoming Fourth of July weekend is rapidly approaching. My daughter is having a graduation celebration for her family. My oldest grandchild graduated from Ohio State last winter and is coming home from hiking the Appalachian trail before she takes a job in Maine this fall. In addition, my youngest grandchild is graduating from high school, and her husband is receiving his MBA. The event is being held outside, so I need to plan accordingly. I have picked a very feminine top to go with leggings and flats so I can be appropriately feminine without going overboard.

It does not seem possible, but the next big event is Liz and I’s big trip to New England in the fall. Just like that, another summer will have gone by. At my age, there is no way I should be wishing time away. As my mom was fond of saying, age is like a roll of toilet paper, the closer to the end you come, the faster it goes. As with most things mom told me, she was right.

It seems, no matter how small the public interactions are, when I am positively impacted, the better my life is. It is like charging up my gender battery. I constantly need it. Such as the positive interaction I had today.

Painting a Picture

 

Image from Vinicus Amix
Amano on UnSplash.

During my life, I have never been accused of being an artist. In fact, I would mess up drawing stick figures.

The best thing I could do was connect dots. Which I needed to do quite often in my gender conflicted life. Basically, the main dots I needed to connect were, was I a boy or a girl. It ended up taking me far too long to finally connect those dots and attempt to draw my gender picture.

When I began to experiment with makeup, I learned the basics of facial artwork and even I could make myself look better in the mirror. Mainly, though, I struggled along until I summoned the courage to request a makeover from a professional makeup person at one of the transgender-cross dresser mixers I went to. He did a miracle job and transformed me into a woman who I only had dreamed of. Most importantly, he was able to explain to me what he was doing in a step-by-step format that even I could understand. I looked so good, I was invited along by the “A” listers, as I called them when they went out to explore other venues after the mixer was over. I even got the last laugh over all of them when a man tried to pick me up in a venue we were in, and they were not.

Sadly, the success I felt from the mixer did not last long when I had to go back to the real world, I was a part of. When I did, I became mean and nasty to my wife and others around me. All the way to almost losing jobs because of my attitude. No way to paint a picture. Somehow, I needed to get better before I self-destructed my life.

I hung on until I did get better when I had the chance to leave my closet more than once a year for Halloween parties. I was aided by the fact that my artwork with makeup and clothes continued to improve until I looked better than some sort of a circus clown in drag. I simply had to if I was ever going to have the chance to live my dream. Through it all, it did occur to me how difficult the process was going to be. I was painting two pictures at the same time, one as a transfeminine woman. One as a successful man. The stress of doing so nearly killed me. Being a man was easier because of all the white male privileges I had gained but being a transfeminine woman felt so exciting and natural when I painted her.

By the time I had gotten this far, I found I had painted myself in a corner. I could see the finish line for a change, while at the same time, I had a wife I loved, a family I loved and a good job to protect as a man. Decisions, decisions were wearing me down. Primarily because it was so frustrating to me to have worked so hard throughout my life to paint two pictures, only to have to finally choose between the two. What I did was let the public choose which picture they preferred. Since my transgender woman had an unfair advantage, she won the contest easily. She got to start all over again and learn from all the mistakes her male counterpart made and go from there. Time and time again, the public picked her.

Putting the finishing touches on my feminine portrait proved to be easier said than done. First, I needed to come out of my closet to what was left of my blood family. I received a 50/50 reception when I was accepted by my daughter and rejected by my brother. By this time both of my parents were deceased. Predictably, both coming out events were scary and quickly resolved. My daughter wondered why she was the last to know while my brother did not have the courage to stand up for me to the rest of his extended family. We have not spoken now in over a decade. Sad but true, he never wanted to see my finished portrait. Conversely, my daughter and I are closer than ever.

But then again, are our portraits ever finished until we die. Shouldn’t we always be making small upgrades the best we can? Plus, age should put us in a better position to do it. Sure, painting two completely different gender portraits at the same time was difficult and at times required tons of skill to keep one hidden. But somehow, I was able to gain the artistic skill to make it happen.

The powerful draw of an overwhelming dream was all the motivation I needed to become a better artist and provide the background I needed to live a life as a transgender woman.

The Big Risk

 

Image from Joshua Rawson Harris
on UnSplash.

When you jump from one of the main binary genders to the other. In my case of course it meant leaving all my hard-earned male privileges behind and move into a largely unknown world.

The risk was tremendous the farther I went along. Mainly because I was accumulating an increasingly amount of male baggage. Such as family, house and good job. At the same time, I was perfecting my transfeminine appearance, which encouraged me to move forward in the world. To be sure, I was involved in being tested with a double-edged sword. Or which way should I go? I spent many wasted hours trying to obsess over my future, which was still very vague. At that point I did not even know if I could even exist in a fully transfeminine world. On nights I was accepted by the public, gender euphoria told me I could. Then, on the nights I was rejected by the public, I thought there was no way I could ever live my dream, and it would remain just that…a dream. A dream which never would go away. 

Through it all, the idea of risking all my existence remained with me and naturally scared me to my bones. I was hiding away my biggest secret and even though I did internalize it well, it was a drain on my mental health. Which is a side story I tell often because it is something I think more transgender women and trans men can learn from. At least I hope so.

Something else, I don’t think the average person understands about us, is this is not a casual joke to us, and we just cannot stop putting on a dress on a whim. We are ready to risk it all to live an authentic life as our true selves. Free from our closets. The problem was at the end of a day out, most of us must go back to our old unwanted male selves (or female selves for trans men). For me, it was always a heart-breaking experience as I tried desperately to maintain my male façade for my wife and work.  The only alternative I had was to attempt to live part of my life as a trans woman and the other half as a macho man. It tore me up.

The entire process just became worse and worse when I began to carve out an all-new life in a feminine world. The more success I felt, the less I wanted to go back to my old life and began to research the prospect of living my lifetime dream. In fact, all I can remember all I really wanted to be when I was young was, I wanted to be a woman. Which of course, I needed to keep to myself. I was miserable as I felt as if I was the only boy in the world who felt that way. It took me years to learn I was not the only male in the world who wanted to be female and was prepared to take the risk to do it.

I was able to find a couple of real live acquaintances who took the risk, almost, so I could judge what it meant for me if I decided to follow in their footsteps. I say almost because one the transsexual women I knew was a very attractive retired firefighter in Columbus, Ohio and had a very good pension to live on. The other trans woman I knew was even more attractive in her own right and a very accomplished electrical engineer and would always find a job. I had a good job but not one which would carry over to a gender transition. So, I had much more to consider, not to mention neither of the women I mentioned were in a serious spousal relationship and I was. Right in the middle of a twenty-five-year marriage. I would later come to know how similar yet drastically different our transgender community is.

The pressure I was feeling to take the final risk continued to build. Aided by the success I was having in dealing with the public, I was encouraged to take the final risk in my life. At this point, destiny stepped in to show me the way. My two major stopping points were my second wife and what I would do for an income after I transitioned.

My wife tragically died, leaving me with one to speak of to object to me leaving my old life behind and beginning a new one. Then, by that time, I was in reach of being able to retire on early Social Security income plus what I could sell online. In many ways, the lightning did come right before the rain for me and then the sun came out. When it did, I could see my dream life had arrived and I could live how I wanted to.