Showing posts with label cross dresser. Show all posts
Showing posts with label cross dresser. Show all posts

Thursday, July 24, 2025

No Easy Way Out

 

JJ Hart doing Trans Outreach Work. 

Like many of you, I struggled for years to escape my dark, lonely gender closet.

As I beat my head against the closet walls, I stared longingly into the mirror, dreaming of the day I would find an easy way out. As I did, it became increasingly evident to me that there would be no such escape from my dominating male self. He would make life miserable for years because of my indecision.  One day I wanted to be a boy and the next I wanted to be a girl dictated how I lived.

After years of despair over my gender dysphoria, I began to see a sliver of light in my closet when I briefly opened the door to look out. At first, I was getting the door slammed back into my face when I went out in public. Too many people were laughing at me to my face or worse yet, I could hear their comments behind my back. I was sent home early many nights in tears, wondering what I was doing wrong with my feminine presentation. Following intense introspection, I discovered what was wrong. I was letting my old male self-make my fashion decisions and dressing for men instead of women who were for the most part controlling my destiny as a transgender woman. Without the support of women, I would have never made it out of my closet at all.

Even as I learned my lessons on presentation, I still found there would be no easy way out of my closet. I discovered the more walls I scaled on my path to transgender womanhood; the more walls would appear to challenge me. Mainly because I was out in the public eye so much more, and I was challenged to find the proper wig to wear all the time as well as find better fashion to augment my wardrobe. There was no way I wanted to wear the same outfit day after day when people began to recognize me. To offset the extra attention, I needed to increase my visits to area thrift stores to find bargains I could afford, and more importantly, fit me. I was obsessed with outdoing myself when it came to my feminine presentation.

It turned out, the public was noticing as I lost nearly fifty pounds and started taking better care of my skin. If I behaved myself in the world, and was friendly, I crossed the line into communicating with other women. Of all the walls I needed to climb, communication skills were the hardest to scale. The change was dramatic because I needed to change my communication from direct male to indirect female as I learned women often talk with their eyes. Thus, I needed to get better in looking another woman in her eyes when I talked with her. Often doing it as a man was a threatening option, while doing it as a woman was not optional. I needed to learn to do it. By doing so, often I could see what they thought of me. Did they think of me as a woman or sort of a man seeking admittance into their world.

Mostly what I received back was curiosity. What was I doing in their world? And I think they understood my interest in being admitted to the girl’s sandbox went far beyond just putting on a wig, dress and makeup. One way or another, the process was extremely challenging and kept me guessing every night about what I was going to experience because some nights I was tired of climbing walls. I kept looking for the last one to climb, but found I was not even close. Mainly because the gender club I was seeking to join was so complex. On the other hand, the process of totally leaving my closet and male privileges behind was still quite scary and I needed total confidence in what I was doing before I made the final jump.

My introduction to HRT or gender affirming hormones gave me the confidence I needed to keep going. Suddenly the hormones helped me to sync up my external feminine self with my internal one. It was the final shove I needed to get out of my closet and live a new life as a transfeminine person. It turned out there was an easy way to escape if only I possessed the inner strength to look for my truth. Once I did, my fragile mental health improved, and I set my sights on enjoying my family more since a huge weight had been lifted off my shoulders. In the end, it was all worth it, but it was never an easy trip to go on, or I could find no easy way out.

 

 

 

 

Wednesday, July 23, 2025

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.

 

Tuesday, July 22, 2025

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.

Monday, July 21, 2025

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.

 

 

 

 

Sunday, July 20, 2025

Can You Ever Enjoy the Ride?

 

Image from A. C. on UnSplash.

Lately, it has occurred to me how often I did not pause to enjoy my gender journey.

Perhaps it was because for the longest time I experienced very little gender euphoria for two reasons. The main reason was, I was never raised to feel any joy in my life. Nothing was ever good enough. So, when I entered the world as a novice cross dresser or transgender woman, life was very tough. The other main reason was, I was approaching my life from the exact wrong way. Deep down I knew when my “buzz” went away so soon from merely dressing up in feminine clothes in front of the mirror, I was doing something wrong. I did not know then my gender issues ran much deeper than just a love of fashion and makeup.

Before I knew it, I was in a vicious gender circle in my life when I needed to dress up rather than wanted to. There was a huge difference. When I needed to cross-dress, I had the tendency to take more chances and jeopardize my life as I knew it because I knew there was no way my parents would ever understand how their son was really their daughter. Plus, there were many other distractions too, such as not being able to afford my own wig until I was well into my college years. I hated running around with a towel on my head fantasizing that I had a full head of luxurious girls’ hair.

There was always something I was reaching for which ruined my present enjoyment. Such as a better dress, shoes or makeup which could help me look better as I had neared an impossible ideal of attractiveness. Facing my reality of appearance when the only feedback I had was in the mirror. As we all know, the mirror has a tendency to lie to you if you are not careful, and I needed a way to test my presentation as a transfeminine person in the public’s eye. Easier said than done, when I was busy living my own down low in a male life I was frustrated to be in anyhow.

Very quickly, I learned the mirror had been lying to me as I was rejected by the public. To succeed with my dream, I needed to pause my life and attempt to find out why I was having all the problems I was having. Almost immediately, I determined I needed to get my male self out of the way. He was dictating how my fashion presented itself and it was all wrong. For any number of reasons trying to dress sexy in the wrong places was getting me into trouble. My guy was dressing me for other guys when I should have been dressing for other women. Once I figured out, I was not a teen aged girl, my public life became decidedly better.

So much better, I was even able to enjoy several of the solo nights out I went on to be by myself. Even though I knew I was a transgender woman, I was just being me, and the public (amazingly enough) was accepting it also. My mirror even came back into play, and I used it more often in places such as women’s rooms to adjust my hair and makeup.

Life then began to roll on very fast. All the way to the point I was having a difficult time keeping up. I was learning so much about the feminine side of life, it was too late to turn back then and more and more, I was discovering how much I loved this new side of life I had always dreamed of.

Also, my life was reaching a new level of complexity as I was shutting down the male side and giving full access to my female side who had waited so long to be free. My problem was I was still trying to live part time in both genders as I transitioned, and I was afraid of what would happen when I lost all my male privileges. Finally, my mental health could take it no longer and I had to jump off the gender cliff I have written about.

As I jumped, the ride down was scary but fun in its own way, not unlike a big rollercoaster at an amusement park, the ride up in many ways was worth the ride down. All the fear and terror I had experienced when I had come out to a close family disappeared when I was accepted by my daughter and my wife Liz and a warm set of relief sat in. I could not wait until I could get back in public and live my true existence out of the closet. I was creating my own universe for a change and not relying on someone else to do it.

I began to build my own female privilege and thrive in it. It continues till this day and is the topic for another day. In the meantime, I often try to pause my life and enjoy where I am in my life.

 

 

Saturday, July 19, 2025

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.

 

 

Thursday, July 17, 2025

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.

 

 

Wednesday, July 16, 2025

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.

 

Tuesday, July 15, 2025

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?

 

 

Monday, July 14, 2025

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.

 

 

Sunday, July 13, 2025

Painting Myself into a Corner

 

Image from UnSplash.

I was always an adequate house painter and not much more.

Possibly my biggest problem was ever finishing a project. Every time I would start, I got bored and quit before the project was done. There were even times when I would unknowingly paint my way into corners. Little did I know, all of this would carry into my life as a cross dresser and later a transgender woman.

Like many of you, I started experimenting with my mom’s clothes which I became attracted to at a young age. It was most likely a carryover from watching mom (and admiring) put on her “face” or makeup as she called it. I wanted to see how the whole girl package worked for me. At that point, I began to place myself in danger of painting myself in a corner I could not get out of. The corner I am referring to is being caught and facing irreplaceable damage to my life as I knew it in a male dominated family. As the oldest son, I was expected to carry on a macho tradition.

The problem was of course I did not want anything to do with male tradition because I was enjoying my alone time cross dressing as a girl so much. I worked onward on my feminine artwork, as I sought to buy my own makeup and pantyhose from my allowance and newspaper route money. Then I experimented with my limited time until I became a little bit better and did not look like a clown in drag. I was slowly finding my voice as a transfeminine woman.

The more I discovered, the more I risked painting myself into a corner. When I was in the corner, sometimes I paused to look around for a reality check. An example was the night I was in one of my regular venues dressed to fashionably blend in with the rest of the women and I needed to discover if I wanted to escape the corner I was in at all. It turned out I loved the real me and wanted more time out of my closet. I was beginning to learn who I really was, but it turned out I would have many more corners to paint myself into. Such as settling into one new person and not changing each time I went out into the public. I was shocked how quickly people remembered me; I needed to wear the same wig as a start to solidify my future in the world as a transgender woman. In a way, the experience was boring because I was always enjoying my newfound ability to shop in wig stores for the so-called perfect hair after waiting all those years to do it.

Another of the major corners I painted myself into was how I ended up just pursuing the basics of communicating with an all-new world. I never expected people (particularly other women) would ever want to talk to me as a woman because they rarely wanted to as a man. My guess is the women were just curious about me wanting to be in their world, or just I did not threaten them anymore when they let me behind their gender curtain.

In many ways, my decision to undertake gender affirming hormones was me painting myself into a corner was the biggest risk I had ever taken. Undertaking HRT was my own ride or die. Either I made it as a transgender woman with the help of hormones would preclude me ever going back to a male life I never asked for, or I would have to find another way out. Spoiler alert: I was fortunate when I cleared the medical screening, I needed to begin what I considered to be lifesaving hormones, and I flourished. My decision could be compared to a gender insurance policy. I was making sure I was successful when I finally synced up my inner and outer selves.

Today, I have put down my paint brush and concentrated on living my life as a supported transfeminine person. Sure, I confuse some people with how to refer to me, but that is their problem not mine. They need to be educated to the world anyhow. Transgender women and transgender men are not their enemy, but their ignorance is. I filled my world with acceptance from a loving world and watched many other people paint themselves into their own corners. I took many risks along the way to do it and out of sheer will power to do it.

I have felt the depths of loneliness, all the way to having a new family all my own (except my daughter of course, she was always there). I don’t think I would recommend such a unique human journey to anyone else, but it was anything but boring.  As a painter, I have finally come close to finishing a project.

 

 

 

 

Saturday, July 12, 2025

Did I think Life Would Turn Out this Way

 

JJ Hart.

Did I think life would turn out to be this way, I would have said NO!

In the earliest days of just exploring my mom’s clothes and admiring myself in the mirror, I never thought life would have become as complex as it did. For years, I thought my cross-dressing urges were an innocent hobby which hurts no one. I was entertained and it was all that mattered in my selfish world.

Little did I know, all I was going through was just the beginning of my life I would have to adjust to if I was going to survive. I was embarking on what turned out to be a very unique life as I had the opportunity to live life in two of the main binary genders.

To put it all together on a timeline, I was in my thirties when I first read the term transgender for the first time, and I thought I had finally found a term which described me. Or, at least put words to my gender dream of possibly living a transfeminine life. Up to that point, I had only experienced the other gender variant people I met at various mixers I went to. When I attended the mixers, I met everyone from cross dressers in cowboy hats barely covering their masculinity all the way to impossibly feminine transgender women who were on their way to surgery. I certainly did not think the mixer I went to would turn out that way. I was expecting to attend, meet people like me and come away with new answers about myself. Of course, it did not turn out that way, and I came away with more questions than answers afterwards.

Primarily, I found myself on a sort of a gender balance beam. I was very clumsy and became well versed in playing both sides of the gender spectrum. At times I was good at my games and at times I was very bad, and I suffered. Through the bad times I needed to keep my eye on my gender dreams, be selfish and do the best I could. Perhaps the worst part was, I still did not know how any of it would turn out.

It was only when I managed to escape my dark, lonely gender closet and explore to learn if my future transgender dreams were possible at all. I was in a long-term marriage with a woman I loved, in a successful job and outwardly living a good male life. Why would I want to sacrifice any of the white male privileges I had earned. I did not think on occasion that I ever could.

What changed everything for me was the further I went on my journey, the more natural I felt. I began to think more about my life was meant to be this way. When I was selfish in my gender choices and I did my best to be a chameleon with my life. These days, I would be known as being gender fluid. Another term not known in those days, instead I thought of myself as an androgynous person. Especially when I started gender affirming hormones or HRT. What happened was, I really started to play with fire then. I had given myself a loose timetable until I made the final transition from male to female but could not keep it when the changes to my body became much more noticeable than I had ever imagined.

I never had thought in a million years, my life would turn out this way and I needed to arrive at a point where I needed to be selfish again and give up on my male self. My longer hair, softer skin and budding breasts were giving me away. It was time for a change. In fact, way past time for me to face the inevitable, I should have been living a transfeminine life all along.

All the torment and balancing acts I put myself through were no more than tormenting myself needlessly. Perhaps the final clue was how quickly my body took to the new feminine hormones. There was no negative to the process at all and the calm I suddenly felt led me to feel I was in the right place.

So, no, I never thought I would be in the spot I am in today. I am living as a transgender woman with a wife who supports me totally. The only slice of life I lost was my brother’s acceptance which was overcome by my daughter’s. It has been over a decade since I have spoken to him and truthfully, I haven’t missed our interaction. I am sure I had a few lucky breaks along the way, but for the most part, I think destiny was leading the way. Along with my stubbornness to continue my journey. It does not matter as it all worked out.

 

 

Friday, July 11, 2025

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.

 

 

Thursday, July 10, 2025

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.

 

 

Wednesday, July 9, 2025

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.

 

 

 

 

 

 

 

 

 

Tuesday, July 8, 2025

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.

 

 

Monday, July 7, 2025

Trans Girl on the "Down Low"

 

Image from Josh Withers
on UnSplash.


According to Wikipedia, down low is basically an African American term for gay cruising of other men. For this post, I am going to use it in another sense.

First of all, I need to take you all back to when I first considered my down low to be as I cheated on my wife. But I was doing it by cheating on her with another woman, which happened to be me. Of course, nothing made what I was doing right but I could not stop doing it as it had a powerful draw on me. Those were the exciting days of leaving the gay bar scene behind me and begin exploring the world of straight bars as well as lesbian venues.

Very soon, my success turned to failure as I began to feel guilty about lying to my wife about what I was doing. I tried my best to rationalize my thoughts because after all, I was having no physical contact with anyone. Male or female so I could not be accused of cheating, but I still was. The reason was, I had made an agreement with her that I could go out in public several days a week. Providing I never left the house cross-dressed. It was a sacred promise she never forgot and one I could not keep once I began to develop a transfeminine life.

Very soon, I felt as if I was still on the down low every time I snuck out of the house dressed as a woman. As I was basically doing as much as possible. The reason was, I was learning so much about the feminine world I had always dreamed about, I could never turn around and go back to my male life.

It was more exciting to stay on the down low until I could figure out what to do about the life I was leading. In fact, I because the more I experienced the new world, the more natural I began to feel as I was able to put the image I always saw in the mirror into motion. In many ways, I began to feel so natural as a transgender woman, it was difficult to ever return to being a man at all. I had to consciously tell myself I still was a part time man when I worked. So much so, I was beginning to be called ma’am when sir would have worked for the occasion. Still, I was secretly overjoyed when it happened.

Sadly, through it all, my marriage really suffered. Mostly because I was and am a very honest person and hated lying to my wife about what was really going on with me. Often, I learned when I lied one small time, I would have to lie more often to make up for it. An example was one year when we took a week for vacation and headed north to try to escape the heat. About two days into the vacation, I became increasingly mean and irritable because I really wanted to be spending my time traveling as a woman. Finally, my poor wife had had enough and asked me what was wrong. I lied again and internalized my feelings enough to get by, and we could eventually enjoy ourselves. Deep down, I hated myself for it.

Life began to finally slow down for me as I reached certain milestones in my transfeminine life. I was beginning to communicate with the world and started to feel much better about myself and at the same time my down low activities slowed down also. At least to a point where I could control them. It was around this time too, when my wife’s health began to really decline. It did not know it then, but she only had approximately six months to live. For some reason, I decided to go on a major purge and throw most of my feminine things away and went all the way to growing my version of a beard. It turned out, I did the best I could for the remainder of her life.

When she passed, of course I was tragically shocked and lonely, so I reached inward. The beard went away quickly, and I was able to restock my clothes and makeup. In no time at all, my inner feminine self was coming to my rescue. I began to retrace my steps I had taken as a novice transgender woman, and reestablished myself fairly quickly in the venues I was a regular in.

I was totally freed from the down low experiences from my past and could concentrate on going out to being alone. In other words, I wanted to be around other people. I just did not want them approaching me.

It worked in the short term until I began to socialize with and started to build a small circle of friends who knew nothing of my previous self. I never had had to go on the down low again.

 

 

Sunday, July 6, 2025

There is always One.

 

Event Venue where party was held.

There is always one person who does not know how to or wants to keep their mouth shut around my wife Liz and me.

I am referring to my night of affirmation I referred to in yesterday’s post. Everything got off to a wonderful start as we found the venue a little early and chose a seat in the shade as we enjoyed a pre-dinner drink. Plus, I found my daughter, son-in-law and middle grandchild quite easily. So, I was ready to relax and prepare for a fun filled evening without having to explain myself and my gender choices.

It turned out that I relaxed too soon because after my mother-in-law sat down beside me to once again question my health. Even though I am not very mobile, I have been very fortunate so far to escape any major health problems. That is when things began to get very interesting in the question department. My mother-in-law’s sister promptly sat down in the empty seat beside her and started asking me questions.  That is when the “fun” started.

First, she assumed I was my daughter’s mom, I think.  My assumption of her was she was an older lesbian. It turned out assumptions are like rear ends on people; everyone has one because we were both wrong. I told her I was my daughter’s parent when she said I was her father. Then she could not shut up and waded in further into my personal life. Sitting on the other side of me was my wife Liz and the woman promptly asked Liz if I was her husband. Liz quickly said no, I was her wife. Liz handled it beautifully and the woman moved on, I thought.

By this time, I thought the woman would have learned her lesson and just shut up, but I was wrong. She was one of those people who just can’t leave well enough alone, and it seemed I was the target until she became bored. Obviously, she had no knowledge of our family’s recent history. She was ignorant of the fact that one of the quests of honor last night was also transgender and was there with their partner also.

Then, my first wife showed up and grabbed a seat at the table and I became involved with talking to her. She is the mother of my daughter and will always have that bond, plus she does have some contact with my brother’s wife who rejected me for being transgender so long ago. There was a lot to talk about so I could ignore the woman who probably see she was being ignored by them. But not all the way.

The photographer began to round up the family for pictures after dinner. To start, he asked for the men to gather. My new friend? Looked at me for a second to tell me it was my turn for pictures until I glared at her and did not move. Obviously, she had not learned, and I waited for the photographer to call for the rest of the family to come up for pictures.

Regardless of what she thought, there were pictures taken I should be able to pass along later.

All too soon, Liz and I’s evening at the celebration was over and I did get to see and talk to my transgender grandchild before they take off for their new job in Maine. That was the important part and any dealings I had with anyone else faded away. Hopefully the woman left with a new understanding of the gender spectrum and even better learning how to keep her mouth shut around us. But I doubt it.

The best part is my daughter, and I have pledged to get together more often for breakfast in the future. Without the prying negative comments of an opinionated person who does not know what she is talking about. I don’t think she was a true transphobe, just a person who did not know enough to keep her mouth shut. Obviously, I have had all the right to be called a parent instead of a father and for her to recognize it. Whether or not she ever realizes it, it will be up to her. If she does, I hope I have played a small role in helping to change someone else’s life, who really needed it. I have to say it was difficult not to be negative with her and I was not. Which put me in a transgender educational position I did not anticipate being in. As my affirmation day proved to be much more by helping the public view of transgender population having families and life’s like so many others.

Some people just can’t seem to say no when faced with discussing situations they know nothing about.

 

 

 

 

No Easy Way Out

  JJ Hart doing Trans Outreach Work.  Like many of you, I struggled for years to escape my dark, lonely gender closet. As I beat my head a...