Showing posts with label retirement. Show all posts
Showing posts with label retirement. Show all posts

Wednesday, January 14, 2026

My Gender Timing was Everything

 

Image from Danny G
on UnSplash

For me, timing was everything when it came to completing my male to female gender transition. Plus, there was no way possible to think I would take nearly a half of century to do it.

The problem was, I never considered the extra layers of a ciswoman’s life rather than what a man had to go through to live. Just having to put up with a man in a relationship would have been enough for me to drive me into a lesbian relationship. Although I never really understood why more men don’t want to accept trans women because we understand so much about the way they think because after all, we had to live as a man for a while. But that is a long, drawn-out story to be saved for another time.

In many ways, timing comes down to everything when you decide to jump out of your closet and enter the world. Just a few things to consider are what would happen to you if you were out as your authentic feminine self and ran into someone you know. It happened to me one time long ago when I was married to my second wife. I was happily following my shopping routines in the small Ohio town we lived in when I parked in a parking lot, slid out of my car and right into the on-coming face of my wife’s boss. As I panicked and headed the other way as fast as I could, all I could hope for was he did not recognize me in my wig, makeup, mini skirt and matching leotard top. Fortunately, as I got a quick glimpse of his face, he showed no reaction to me at all.

I thought the experience was behind me until a week or so later, we were invited to a party at their house. At the party, her boss casually brought up how he had seen this big woman at a big box store he was shopping at the other day.  As I ignored the comment the best I could, I saw my wife suddenly glaring at me from across the room, and I knew what she was thinking. It was me; her boss saw that day. It took me a long time to live that one down because I was never supposed to leave the house as a trans woman unless I was somehow supervised.

Timing kept me living on the edge with my job too. What if my “hobby” of being a cross dresser was discovered? I knew I would not be able to function the way my male self-had all his life. I was stuck between the rock and the hard place on several personal fronts. I was becoming increasingly dependent on my lessons I was teaching myself as a woman and keeping my personal life together. All I could do was keep on working towards my dream of living as a transfeminine person. As I progressed along my often-rocky gender path, all I could do was look for a quick exit. But I found out, exits were as rare as on a long-deserted interstate highway.

It was not until I reached my mid-fifties, did I begin to see the faint out-lines of a possible gender exit ahead for me. All I needed to do was time my male exit correctly so I could cover the main living basics such as spousal support (or nonsupport), a job to support name changes, all the way to all the identification forms I would need such as a new driver’s license. For me, the name change was the most challenging because I needed to go before a very conservative judge I even knew before as a man. Surprisingly, he just smiled and approved my paperwork and name change and the rest was basically easy. So timing on that exit went smoothly with no roadblocks.

Other exits were not so forgiving for me. Such as what was I going to do about a job at that time. I had just closed my restaurant and was essentially broke, and I needed to find a job fairly quickly to support myself. I guess timing was everything and I took an easy exit into a job that I hated. I took the job anyway and managed to keep it for the couple of years I needed to work to claim my early retirement and keep myself afloat by selling vintage collections that my deceased wife and I had put together over the years. During this time of my life, there were other main detours which were difficult to navigate.

That was when my current wife Liz stepped in along with a huge push from destiny to erase any doubts in my mind that I was making the right decisions. I can not forget to mention this was also the time when I was able to begin HRT or gender affirming hormones and take another smooth exit away from my old male life. Putting him in my rearview mirror was the best move I had ever made in my life. I had a new me to go with my new name, and I was ready to go by the time I hit the age of sixty-two. I did not even have to revisit another job exit and just totally retired and moved in with Liz. Where I still am nearly a decade later.

Timing was everything for me, and even though it took me longer than I ever expected to reach my dream, the trip was worth it and I managed to even stay on a very rocky gender road full of roadblocks without wrecking.

 

 

 

Saturday, December 16, 2023

At the Crossroads

Image from the
Jessie Hart Archives

As I continued along my gender path to living as a fulltime transgender woman, I arrived at several crossroads. 

The first of which was finally deciding I was transgender at all. For years I considered myself nothing more than a very serious cross dresser. Perhaps the biggest positive aspect of staying a cross dresser was my wife knew of my gender pastime before we were married. She even grudgingly bought me gifts such as woman's clothes. In fact, we had a separate gift exchange at Christmas every year especially for my feminine self. 

On the other hand, my wife was totally against any idea of me being trans, saying she didn't want to live with another woman. I had no comeback for that argument since she did marry my male self. Still it did not stop me from exploring ever further the feminine world I thought I wanted to live in. As I did my explorations, the process felt so natural I just had to keep going. At the crossroads I decided I was indeed transgender and I was pursuing a lifestyle not just participating in a hobby. From the point forward my life changed and I had many new decisions to make.

Decisions such as how would I even structure a totally new life in a woman's world. Along the way, I learned the possibility of living as a trans woman meant so much more than just doing my best to present well in the world and blend in with the public. What would I do about the three "F's" as I called them, or family. friends and finances. At the time, I didn't have the answers to many of the questions so I kept searching. Of the three challenges, I decided to come out to my family first and see how it went. When I did, I received a fifty-fifty split in return. By this time in my life, my close/blood family had been reduced to two people. My daughter and my slightly younger brother. As it turned out, my daughter was very supportive and my brother was just the opposite. I tell the story often how I gained a family with my daughter's in laws and lost my brother's family at nearly the same time. Sadly, it all happened over a decade ago and things have never changed.

The next step I needed to consider at my crossroads was what would I do about what friends I had left from my old male life. Again, sadly, I had very few close male friends and had lost most all of them to death in a very short period of time. So I had very few friends to tell. No worries since I had never been able to make since seemingly I kept pushing people away my entire life because of my gender issues. I thought the fewer friends I would have to tell, the better off I would be. 

On I went at my crossroad when I came to the third "F" which was finances. I obsessed on what I would be able to do to support myself. I had built myself into a successful well paying job which I knew would be impossible to transition genders on while I worked it. What did work in my favor was my age. I was close enough to to retirement age to consider taking an early retirement. Which meant all I had to do was work a couple more years and then not have to worry about transitioning on the job. 

What ended up happening was, I painted myself into a corner I couldn't get out of. The pressure grew so intense as I tried to live both as my old male self and my new feminine self. It literally tried to kill me before I said enough was enough. One night as I sat alone and pondered what I was going to do, I finally decided to do the right thing and give up totally my old male self and live as a transgender woman. 

From that point forward, I felt as if a giant weight had been lifted off of my shoulders. I had made the correct turn at the gender crossroads and was able to move on with a new life. I waited for the paint to dry in my life and gently learn to live as my authentic self.   

No One Way is Correct

  Image from Gabor Kaputi on UnSplash.  Even though we transgender women and trans men often follow similar gender paths to get to our goa...