Showing posts with label trans woman. Show all posts
Showing posts with label trans woman. Show all posts

Tuesday, June 11, 2024

Did I Get it Right?

Out to eat with my wife Liz on left. 

I make no secret of the amount of major moves I needed to make to how I arrived to live my life as a transgender woman. Now at my advanced age of seventy four, I wonder if did I get it right.

Of course like most of you, I needed to give up much more than my unusual white male privileges to transition. Along the way, there were marriages/ spouses, friends, family and job losses to deal with. In other words, many sacrifices to make to follow my gender path. In other ways, destiny and years enabled me to transition to a feminine life. My one big deterrent was my relationship with my second wife who in no uncertain terms was telling me she did not want to live with another woman. In fact she made it abundantly clear she didn't like my woman self at all. Except when she needed help with her make up. What could I say? She was correct when she said she didn't sign up for all the gender issues she was now dealing with in our marriage. 

Most of you know she died suddenly from a massive heart attack. The tragedy freed me up to do my own thing. My own thing turned out to be I quickly turned to my own woman for comfort. I discovered almost immediately, I got it right as I was having the time of my life as I explored a new world as an out transgender woman. 

I also found I got it right when I discovered other women in the world who would accept me without having any knowledge of my old male past. When I did, I was able to really begin to live a new life of my dreams. I also did it right on how I was able to raise my daughter who ended up being one of my biggest supporters to this day. However, I didn't get it right with my brother and his in-laws who roundly rejected me. Sadly, by this time, most all of my very few real friends had passed away so coming out to many people was not a problem. 

So, by waiting so long to complete my male to female gender transition worked out right to me plus, even though I was not enjoying my old male life anymore, I still took advantage of the male privileges I would lose. It finally got to the point it was ridiculous to continue a life anymore split between the two major binary genders. The stress and tension became too much for my mental health to sustain and I tried alcohol to solve my gender problems.

I did it right and stopped drinking as much as I did before I permanently injured my body and when I moved to Cincinnati to live with my future wife Liz. Liz encouraged me to permanently leave my male life behind and live fulltime as a woman with her when she told me she never had seen any male in me at all. Even when I was trying to be.

Finally, I really did it right when I was medically cleared to begin taking gender affirming hormones. My body accepted the changes easily and I loved them. So all in all, I did it right when I decided to transition into a full time transgender woman. Destiny was leading the way the whole time and the only mistake I made was when I tried to get in it's way.



Monday, June 10, 2024

Then I Went and Did It!


Trans Girl image from
Alexander Grey on 

I played around for nearly a half a century being a very serious cross dresser. Sounds like a long time, doesn't it!

It was while I was doing it but now it seems like it was a blur. Most of it started with all the problems of sneaking around my home when I was growing up. I needed to use a ton of creativity to hide my cross dressing itself and not to mention the clothes I had accumulated. Somehow, I managed to do it all. Who knows, maybe it all made me a better person? I doubt it but at the least, the process helped me to be more creative with my life.

As I progressed slowly with my makeup art and improving my women's fashion choices by going to thrift stores, I found out I could do more. Then I went and did it by going out and testing the public's reaction to me as a novice transgender woman or at the least a skilled cross dresser. I found, the more I did it, the more successful I was and I felt so natural. To me, feeling natural was the best way I knew I was on the correct gender path and I wanted to keep going. Plus, feeling natural, gave me the confidence I needed to always push my gender envelope and try to do more and more. I even changed the way I viewed my Halloween costumes I was choosing. I started to go away from my trashy woman's look and then tried for a more realistic approach. I searched my brain for ideas which allowed me to try to present as a cis-woman at a Halloween party. Again, I went and did it when I succeeded at two parties where I was actually mistaken for a woman. Which in fact I was just learning I was.

By this time, it was too late to turn back and ignore my gender dreams. I was having so much success building a new life as a transgender woman, I just couldn't turn back. Even my sexuality was not a problem when I began to attract more attention from cis-women than I ever had as a man. I was validating myself as my own type of woman through my years of femininization and it felt so right. Then, I went and did it and jumped into the girl's sandbox and after a few bruises was successful. The claw marks I received on my back I felt were all learning experiences and I stayed and eventually held my own. 

All of this led me to my next transgender step of researching the possibility of beginning gender affirming hormones. Then I went and finally did by making my first appointment with a doctor who I heard would prescribe the hormones if a person was healthy. Thank the Goddess I was and the fun started. Like so many others, I needed to begin my hormonal journey on minimal dose of medication until my doctor and I could see how my body reacted. As it turned out, my body took to the new feminization hormones the way I hoped it would. It was like a big I told you so as my body changed. Inside and out. I needed all the help I could get in the appearance department and I was overjoyed when my facial angles softened and my hair quickly grew to a point where wigs became a part of my past. Luckily, my family history had no male pattern baldness for me to deal with. 

Since my overall appearance was becoming highly androgynous, I was loving it, I decided to give up on what was left of my old male life. I was to the point where none of my male shirts fit my breasts anymore, so rather than buy new bigger ones, I decided to go and do it. Give away what was left of my male clothes and live fulltime as a woman, transgender or not I was ready for the world. 

Since I had taken my time to make certain my gender decision was the correct one, I had no problems of never looking back. Many times now, I wish I had the courage to do it sooner and not have to worry about so many then I went and did its. 

Sunday, June 9, 2024

Gender Puzzles

Image from Norbu Gyachaung 
on UnSplash

At what age can we act as if we understand our gender issues or dysphoria? Or will it forever be a big gender puzzle.

I suppose I can say, I never really understood exactly why something clicked with me the first time I tried on my Mom's clothes. The whole process caused me to finally understand I put so much into a process of dreaming of a feminine life which turned out to be so big, yet so small. The big view of course was having the success to go forth and conquer a sometimes negative world who was not used to gender explorers. The small view was thinking of all the pieces of the puzzle which allowed me to break out and break free in the world as a transgender woman. Just trying to remember all the facets of living as I do right now sometimes is very intimidating to me. 

Often, I just have to go back to pieces of the gender puzzle I was able to piece together so I could get a glimpse of how the final picture may look like.  I should have saved my energy since I am still putting together the puzzle. Since I don't have the patience for puzzles anyhow, it never mattered to me.  Through it all, the key word was outrageous since I never knew exactly what I was ever doing as I blindly followed my gender dreams. First I had to learn to not be outrageous in my dress and fashion and dress to blend with other women in the public's eye. Not what I thought I looked good as. I could also not be overstated or outrageous in how I acted. Again not to invite unwanted attention to myself. As a male I never liked crowds, so I had to learn all over how to conquer all my fears when I was out in the world with all my male/white privileges stripped away from me. So, outrageous to me at that time in my life was knowing I could indeed make it in the public's eye as a transgender woman.

Then I was back to the damn puzzle. It seemed when I was successful at piecing together one piece of the gender puzzle, I just could not figure out the next piece. Just when I thought I had made it, I was rudely awakened by a gender bigot telling me how much farther I had to go. My biggest example was the night when my wife Liz and I were at an lesbian Valentines Party. At one point, Liz left me alone for a couple of minutes to go get something to eat and in that brief time a lesbian TERF attacked me. She rudely asked me what my "real name" was and was extremely hard to dissuade from attacking me any further until Liz came back to save me. It taught me how far I still had to go in life since I essentially "raised" around accepting lesbians and was na├»ve when I was confronted.  I found in my new life I was young again and never too experienced to learn.

I was fortunate to finally having the basic resources to piece my life's puzzle together. I learned I could step into the feminine universe briefly then make my way into the larger universe of women eventually. All the nights with friends at the diverse mixer/parties I went to in Columbus, Ohio helped me to see and interact with all levels of the transgender and LGBTQ communities. By doing so, I learned where I belonged with my ongoing puzzle issues. I just knew I was excited often with how my journey was progressing. The problem I was soon experiencing was one which many other of you trans women have. What to do concerning  an unaccepting spouse. Sadly, too many marriages reach the end of the line when the gender rock meets the hard place with a trans spouse when the pressure becomes unbearable.

For the first time in my life, I had to have the patience and resilience to put my gender puzzle together. Now I am down to the final pieces as I reach the final stages of my life. All I can hope for is to pass on to the other side as painless as possible and I hope you are as successful with your gender puzzle as I managed to be. 

Friday, June 7, 2024

Last Chance

The Ohio State Student Union
with Brutus Buckeye

In  a recent post, I discussed the problem of waiting through years of cross dressing before I could finally transition into fulltime transgender womanhood. 

Then when I came out, I faced certain people who somehow didn't think I was deserving of the transgender title because I took so long to do it. Of course in my usual way, I thought to hell with them, we all are different in how we are able to transition. In most cases, the younger trans people who were saying all of this, had no knowledge of the conditions we faced in our younger days before the internet and social media. Our closets were potentially darker and more lonely than the days after the internet. 

Enough complaining, reality set in for me as did my age. All of a sudden, all those years I spent supposedly preparing myself to come out of my closet had taken me to the age of sixty and I was facing a now or never proposition as far as undertaking my final transition. In addition, I had never worked on anything as hard as I had to cross the gender border to see if the feminine side was indeed greener. Slowly but surely, I found the grass was greener and I was much happier there. Once I did, my age became a major consideration. Being sixty meant I had more life behind me than ahead, so I had to act. Being the original great procrastinator I was, I needed to change that aspect of my life  and do something about my overwhelming gender issues. 

It all happened one night when I was sitting alone in one of my favorite venues pondering my future when a clear thought came to me. The thought was so simple, I wondered why I did not think of it before. Enough of my drama queen existence.  It was time for my male self to go completely away and I could live in the greener feminine grass for the rest of my life. Plus, the doors of destiny were opening for me so I could. First of all, I was single and did not have an unapproving spouse to worry about. Secondly, I felt I was ready appearance wise to present well enough in public to get by. And finally, my Veterans health care system was starting to approve basic care for trans veterans so I could take advantage of low cost gender affirming hormones which I had long dreamed of taking. As you can tell, I had no real reason not to change my life. I was even old enough to consider early retirement so I didn't have to worry about coming out on a job.

Once I decided my course was clear, now it was a now or never moment I had to act on it. In my mind, I had connected all the male to female gender transition dots I could, so it was time to quit running from my truth and start a new life. As the hormones feminized my body inside and out, I found I had made the right decision. It was my last chance to live my dream and I better take it. I guess I was fortunate in that my choice was crystal clear. I had been transgender all my life and at the least I had lived long enough to live a life immersed in both binary genders. It certainly was not the easiest way to live and I would not wish it on anybody but at the least, my life was never boring. 

Boring or not, I needed to play all the cards I had and take the last chance I had to live my dream. Thanks to a small circle of women friends, who helped me more than they ever knew, my last chance gender gamble was a good one and I made it a success.    

Wednesday, June 5, 2024

Owning Who you Are

Image from the Jessie Hart

During Pride Month, it is extra important to to own who you are. Just as much as it is anytime but Pride may give you the little extra confidence to get by. 

To a large part, confidence in yourself, plays a huge role in you being able to own who you are as a novice transgender woman or trans man in the world. For me, it took many setbacks before I gained the confidence in myself to enter the public's not so accepting world. Just learning the basics of fashion and makeup was a major undertaking for me since like so many of you, I was starting from scratch. Slowly but very unsurely I was able to learn the basics enough to get by. In order to do so, I needed to learn to blend in with other women and not try to be sexier, which was a dismal failure. Stuffing a male, testosterone poisoned body into an ultra short mini skirt or dress just didn't work anywhere except for shock value at Halloween parties. 

Once I began to develop a slight amount of confidence in myself, I still learned the hard way that the sky was not the limit when I came to exploring a new life as a transgender woman. In one venue ( a  TGIF Friday's) I found myself becoming a part of a small diverse group of strangers who knew nothing of my old male life. The group was a mixture of a lesbian and her friends which included a beautiful exotic  dancer who drew the interest of a big bearded guy who owned a motorcycle and managed a lumber yard just down the street. Against the wishes of the group, he shocked everyone by proposing to the wild dancer and found himself in a short lived ill fated marriage. Ironically, I was the only one who showed him any sympathy in the group and we became close, before he moved on with his motorcycle to another job. The whole episode gave me confidence in the fact that men were not as off limits as I thought they were. Even though they were not knocking my door down to date me.

I found out quickly my sexuality did not change as I transitioned from male to female and even was enhanced when I learned all the attention I could get from other women. Most importantly, I did not need the validation from a man to give me the confidence to be myself. Even though I was prepared to see if there was any sort of a sexual spark between the authentic trans me and men, there just wasn't. I was busy owning who I was and she was doing a quality job during the process. As it was, the process led me down many different paths. Many turned out to be good and others were dead ends but my new found confidence helped me to continue to search.

Owning who I was also meant forcing my old, unwanted male self into the closet where my authentic gender self lived for years just existing by cross dressing in front of the mirror. Of course, he put up quite the battle before losing and nearly wrecked my mental health on the way. With the help of a key group of women friends and a loyal, dedicated therapist, I survived on my gender path and eventually thrived. I just had to muster up more courage than I thought I had to do it. To those of you who would ask why I would risk so much to transition, I can only say the process along the way felt so natural and saved my life. 

Some would argue I am less trans than the next person because I waited so long to come out in my life. That is ridiculous because I always knew I had gender issues but did not grow up in an easy time to express them Plus, I would not give anything to have missed out on certain moments of my male life, such as my daughter. Who has led me to having three grandchildren I love very much. So you can see why I don't consider my entire male life to be a waste of time because I learned so much from it. 

On the other hand, switching gears after being deeply embedded in a male world wasn't easy. The process took me many years before I could come up to speed in a new world which was and is constantly changing for women, transgender or not. In fact, it could be argued, catching up is more difficult for a trans woman because we have to start from scratch and often be better in the world than other women just to survive. Having the confidence to own who you are is the only way to do it. 

Tuesday, June 4, 2024

Life in Her World

Image from the Jessie Hart

Once I was preparing to live as a transgender woman, I needed to figure out what to do with my new life. . 

As it turned out, even though I had worked for years to figure out my ultimate gender puzzle, I found I still had a long way to go. When everything ceased to be in my mind and into the world, I faced the formidable task of rebuilding my life as a trans woman and leaving my male past behind. The first major problem came from my old male self accepting any of the idea at all. He kept reminding me of all the risks I would be taking if I transitioned. What would happen to my family, friends and employment if I entered my new exciting world. What I did for the longest time was attempt to live with one foot in one gender and one foot in another. Of course, my less than wonderful idea did not work and the pressure to move into her world fulltime became unbearable. I finally realized I did not have a choice and  I just had to complete my transition. I emphasize I had no choice because some transphobic individuals think I did. I would like them to live just a small time in a transgender life to permanently change their minds.

Another problem I had was the longer I lived in my new trans life, the more routine it became.  I found myself slipping back into my old male bad habits which were long gone. When my white, male privileges disappeared, I had no where to turn when life turned the tables on me. A primary example came on the occasions when my personal security was threatened as a novice transgender woman just learning the world. I discovered I could not just bluster or bluff away problematic situations which arose in the world. In many situations, like every other woman,  I needed to work hard to distance myself from the problem and try to learn from it.  Every time I slipped back into male mode, I was rudely reminded of what I did and quickly adjusted.  

Just moving around became a priority for me. I needed to unlearn the male walk and talk and learn to try to flow like a woman. I practiced everytime I could until I thought I had achieved a basic successful walk so I would  not look like a line backer in a dress. The whole process became easier when I finally realized I needed to put my male self away and adopt the feminine one forever. Without totally knowing it, I had moved away from my cross dressing days into a life in her world as a transgender woman. As far as talking was involved in the process, I write about the feminine art of communication often. As a male my habit of frontal aggression needed to go away as I found myself in a world dominated by passive aggression. All too often, I suffered the pain of claw marks on my back when I thought I knew what another woman was thinking or doing. Instead of making the first move in situations, I learned to lay back and let the other woman make the first move and then go from there.

Life in her world then became a question of how confident I had become. I came to realize even though another woman realized my path was different than hers, I still could be accepted as an equal. When I reached this moment of confidence, my life changed forever and I knew I could live the life I always dreamed of. In her world where I always belonged. 

In order to do so, I needed to finally trust my inner feminine soul to take over and run my life. She did a wonderful job since she had waited so long to do it. I was able to become a well rounded person in her world.

Saturday, June 1, 2024

Transgender Stairsteps

Image from Reinaldo Kevin
on UnSplash

As I progressed through life, the idea of me being transgender took up more and more space. 

When it did, I had to create my own steps to arrive at the next level and negotiate all the many stop signs which impeded my progress. For awhile, I was so engrossed in my own appearance, my second wife called me the "Pretty, pretty princess." Mainly because she did not use much makeup and was not very girly herself. I did get my revenge on the occasions we were going out and she had to ask for my assistance with her makeup. It was all I could do to not say something like did she all of a sudden need the "Princess's" help but I didn't.

Little did I know, presenting the best I could as a cross dresser or novice transgender woman was just the beginning. As I was attempting to learn as much as I could about the next step I was stonewalled by my wife who did not want me to go any farther as a trans woman. Not to mention my male self, who was doing his best to derail my gender journey the best he could. It was obvious, he wanted nothing to do with giving up any of his power over me. 

With or without either my wife or my male self, my path was set and I was intent on finding and climbing the next steps towards living as a fulltime transgender woman. Now I shouldn't get  too far ahead of myself because of all the steep stairsteps I still had to climb. The first step was to determine exactly what my gender identity was. Which included my all important sexuality. Since I was planning on living a feminine lifestyle, would I be expected on changing my sexuality as well. This time of my life was very exciting and scary at the same time. When I made it to my next step, I needed to maintain my balance before I could even think about going forward to another.

Once I maintained my balance and was able to look around in my new feminine world, I loved where I was and could not wait to go on. After all, I was showcasing my new skills at blending in with other women as well as experiencing more and more communicating with other women which I went into in yesterday's post. I can safely say my communication experience was one of the most difficult things I had ever done. The next step seemed to be an impossible distance away. Somehow I made it anyways and the next move was seeking out the availability of gender affirming hormones or HRT. I did get approved by a doctor to begin the hormones and the next step was a huge one. Mainly because I had some sort of an idea of the physical changes I would be going through but had no idea of the internal ones.

All of a sudden, I was a different person. I could cry when I never could before as well as undergoing other inner changes. The step of hormones turned out to be worth the wait and all the anticipation. In fact being afraid of heights and climbing too high was worth it also. Maybe it is the excuse I can use to rationalize to myself why it took me so long to realize my transgender life long dreams. 

Before I go, I would like to wish a Happy Birthday to my oldest Grandchild who is graduating from The Ohio State University in December. My Grandchild also happens to be trans and identifies as "They/Them" and I am so proud!

Friday, May 31, 2024

Trans Girl Passing Privilege


Witches Ball Image. Tom on

Passing privilege has been one of my biggest gender paranoia's over the years. Many because I did not begin my journey with any feminine characteristics I could see. Testosterone poisoning had essentially ruined my life when it came to establishing passing privilege. 

As I began to add angles to my body along with unwanted body hair and muscle mass, I began to think ever presenting well as a cross dresser / transgender woman would be impossible. In order to make my gender dream possible, I needed to look around at the other women my age and try to blend my style with theirs. The whole process was difficult and I made many fashion mistakes along the way. Even though I did, I managed to survive in the world as a novice transvestite on my own and move forward. Mainly thanks to brief moments of gender euphoria which always propelled me forward. To do so, I learned how important for me it was to blend in with other women. All I knew was, I enjoyed it immensely when other women would take the time to talk and communicate with me as an equal.

Through it all, I learned that even if I was not the most beautiful woman in the room, many other cis-women were not either. Since women operate on a more layered existence than men, there were many other possibilities to be successful in the world other than just being attractive. In fact, being transgender gave me an extra quality to my existence which many women were drawn to. As I crossed the gender frontier into a new feminine world, ironically I found I had more interest from women than I ever did when I was a man. 

Probably, one of the more profound statements I was ever told was when my transgender friend Racquel told me I passed out of sheer willpower. Which I took to mean (again) I was not the best looking woman in the room but went out into the public's eye anyhow. Together, we went to many so called straight venues together and had a great time with very little public push back, Even if I was passing out of sheer willpower, I was doing it successfully. Which was all that mattered. 

It mattered even less, when I was able to expand my small circle of lesbian friends who put the icing on the cake so to speak when it came to passing privilege. We were able to attend several lesbian mixers in Dayton, Ohio at several different venues. Even though I was initially very scared to go, I was quickly put at ease when I found I could blend in with the group in the venue. Sometimes the venue would be gay and sometimes straight which added to the excitement. All I know is one night, I was asked to be a lesbian wing person for my friend who was too shy to approach another woman and ask for her name. I even was able to steal a few kisses on the side one night from another woman I met. Willpower passing was great. 

I don't have enough power to do it but I think "passing" should be changed to "blending". With blending, you have the choice to dress with the other women you are going to be around and you have the choice not to if you like. In my case, I always wanted to do the best I could to enter the world as a transgender woman and blend in with the other women who were going to be around me. On the other hand, I understand also it is a trans woman's privilege to go to the grocery store in her heels and hose to do her shopping. It is all part of the fun of entering the women's world. 

The biggest problem with trans girl passing privilege is the amount of stress and attention put into appearance by the media and the outside world. The competition to look better seems to get stronger with each generation with the internet and social media being the major culprits. When the stress goes up for ordinary women to look better, it follows the pressure to be even better is real for transgender women and their quest to blend in with the public. 

At least now, there are plenty of self help makeup videos to help the novice trans girl along plus several of the big makeup stores offer advice and products too. Many more places than transgender women such I had when I was first coming out. Maybe it all equals out. 

Wednesday, May 29, 2024

Doing What is Right


My wife Liz on left. Mother's Day this year.

During several high profile jobs I worked at, doing what was right was drilled into me by my superiors.

Even though it took me many years to finally realize I needed to do it, I came out of my gender closet and started a new life as a transgender woman. As I write about often, I am haunted on how much better my life would have been if I had come out earlier and did the right thing.

I should have known and if I had listened to my instincts, I would have done it. As it was, everytime I cross dressed as a woman I felt so natural and something was trying to tell me something big was wrong. It is no wonder, I struggled with my mental health and had anger issues when now I take all I was going through into consideration. Sadly, the person who bore the brunt of my frustrations was my second wife. Mainly because we had made a deal I could cross dress as much as I wanted as long as I kept it away from our home. I was even allowed to spend the money to go to a motel to get ready for a trip on the town if I wanted to. As it worked out, even that was not enough to satisfy my gender desires. Essentially what happened was I became better and better at my presentation skills and when I did, I enjoyed myself more and more.

As it turned out, we were similar to runaway trains on the same track. I was headed towards gender affirming hormones (HRT) and she was completely against them. Saying hormones broke the agreement we set up when we married. She was right and I ended up between the rock and a hard place before she passed away. Once again it seemed I was back to point zero again in my life but this time, I could not go back to cross dressing in front of the mirror. I was too far along towards my lifelong dream of living in a women's world to ever go back. Still, I had the problem of doing what was right and sticking with my promise to never leave the house as my transgender self. I became desperate and began to break that promise regularly which inwardly I was ashamed of.

Overall, my guy self still had enough influence to try to stop my slide into womanhood by putting up the same old barriers. Barriers such as internalizing all my feelings and trying to ignore my mounting mental health problems by drinking way too much until I could take it no longer and I went out to pursue my other new life as a trans woman. Then tried to be home before my wife and hide the whole evening from her. In the short and long term, my plan never worked because in part it was so difficult for me to remove the makeup I so painstakingly applied. I think now, most of the time she knew when I was out sneaking around and just made the decision not to press the issue.

Deep down, on my end, I knew I needed to press the issue. When I was out living my best life as a transgender woman, I couldn't go back to a life as a guy I never asked for. Doing what was right just seemed to be the fair and natural thing  to do. 

Now, if my story ended there, it would have had a happy ending but it didn't. Approximately six months before she passed away, my wife and I had a massive fight about my part time life as a woman and I decided to make one last ill-fated attempt at quitting my feminine life and purging most of my belongings. After nearly six months into growing a beard and gaining an immense amount of weight, as I tried to quit doing what was right, my wife passed away after twenty five years of marriage. Leaving me on my own to finally do what was right.

I did and decided I was not getting any younger and had followed the proper "prep" work to allow my feminine soul to take control. She did and without indicating any "I told you so." She took over my life life with goodness and control. I will forever wonder what would have happened if I had let her take over sooner because she was clearly doing the right things with my life. 

Tuesday, May 28, 2024

Time Waits for No One if you are Trans

Image from David Cohen
on UnSplash.

Sometimes I look back at my nearly three quarters of a century of life and wonder how I made it.

Often I think I could have made it easier on myself if I had been able to muster the courage to come out much earlier and live the authentic feminine life I always wanted to live. It is difficult to imagine exactly how it would have worked out, because the world has changed so much for transgender women and men. It is always worth mentioning the pre-internet/social media days when trans people were so much more isolated in their dark gender closets.

Timing always has quite a bit of influence on how anyone is able to attempt joining the world as an out transgender person. As anyone becomes older, they have a tendency to accumulate life experiences, material or not. Families come along for many, making the gender shock of changing genders so much more of a problem. Baggage continues to increase when we undertake better employment and secure better housing. Both of which can be very difficult to give up.

Time keeps on moving, which often is the only definite and when it does, the pressure builds to do something about it. The older we become, the more the reality of our mortality sets it and we lose the recklessness of youth. I was certainly much more reckless when I was younger and tried more self destructive acts such as consuming too much alcohol and driving way too fast. Also, as the pressure mounted, my mental health which was already shaky was put to the test repeatedly. Anything I tried seemed to take me farther and farther away from any potential answers I could think of.  

The problem was I couldn't see the forest for the gender trees. Similar to any other woman, my biological clock was ticking away and the older I got, the louder it became. I tried everything to run from my clock but of course nothing worked. Finally, when I turned sixty, I could take it no longer. On one momentous night after years of struggle I gave up my male self and gave in to living fulltime as a transgender woman. I put all the years of experimentation as a cross dresser behind me, dis-carded the remainder of my male clothes and set out to live my dream. Sure, it was scary but all the preparation I put into the move made it more natural and successful from the beginning. Primarily my inner woman was overwhelmed by finally having the final say in my life. 

At the time, I was viewing the entire process as jumping off a gender cliff and hoping for a soft landing. As it turned out, all my prep time when I was actually trying to play in the girl's sandbox worked well for me because I had a chance to build up a close circle of women friends who helped with the landing and even welcomed me in. 

I knew too, I wasn't getting any younger and if I put off a gender transition much longer, I would likely never have the chance again. I was close to retirement age, had no spouse to worry about, and had a limited amount of family and friends to come out to, so even I didn't have a good reason to stay in my gender closet any longer. 

In my case, for whatever reason, I was able to wait out time to the bitter end and come out positive in the process. I wish now, I didn't wait so long to live as my authentic transgender self and put so much prep work into it but no one goes back and gets a second chance to rewind the clock.  

Monday, May 27, 2024

The Power of Hope as a Trans Girl

Image from Dayne Tompkin
on UnSplash.

Of all the emotions, perhaps hope is one of the most powerful.

Especially, these days when the world seems to be coming after the entire transgender community, hope seems to be a precious commodity. In my case, I learned slivers of hope came in the form of brief gender euphoria, when I glimpsed the girl looking back at me from the mirror. She gave me hope I could keep trying to live my dream. 

Then I was forced back into my mundane drab male life I never really wanted and my hope disappeared. Often for long periods of time before I could cross dress again. I was in despair until I could glimpse my feminine image again in the mirror. Perhaps the worst part was I did not know exactly what I was looking for. More preciously, I did not understand the predictability of my urge to be a girl my age. If I was able to document it at all, it seemed every week at least once I wanted to cross dress and be feminine. Why did the euphoria of dressing not last? It wasn't until much later I would realize my answer was I was more of a transgender woman than anything else. 

In the meantime, I was busy watching the teen aged girls I so wanted to be like. Without being creepy, I noticed how they moved and what they wore. When I did, it gave me hope I could someday live my dream of being a woman. Even though I was a student of the female gender, life kept me stuck where I didn't want to be. Later I began to understand no one gets out of life without trauma and mine was an extension of being transgender. Learning to live with my trauma and still hope for better kept me going along with small periods of gender euphoria.

Initially, I took the easy way out by taking trips to mall clothing stores where everyone could present as anybody as long as their money was green and by going to gay venues where it was easy to get in. Later I learned in the gay bars, anyone was admitted but very few transgender women were ever accepted. Which made sense, the men in the gay venue were there for other men, not one who was cross dressed as a woman. I found the best I could hope for was to be accepted as a drag queen which I wasn't. 

The whole process forced me further into the world and gave me new hope for the future. I expanded my horizons past the mirror and into the life I write about so often. Surprisingly, I felt a new life as a transgender woman was possible so I started gender affirming hormones to allow the process to be easier. New friends who never knew my old male self helped me along more than they ever knew and the nights when I went out to be alone suddenly became to socialize with the world. My hope to achieve my dream was alive and well. 

However I felt about my dream coming together, the more I knew I needed to work harder to make sure it happened. For example, I needed to change as many of my legal gender markers as possible back in those days in backwards Ohio. With the help of letters from my supportive therapist, most of the process was surprisingly easy. 

Overall, the power of hope in my transgender life has been a wonderful influence but not a super power which was easy to find or nourish. The whole process took me too many years to accomplish what I set out to do because I did not have the wherewithal or even the courage to do it. Eventually, I did learn it would take more than just hope to fulfill my life dreams, it took action. 

Sunday, May 26, 2024

Trans Displacement or an Impostor?

Image from Tengyart
on UnSplash.

Sometimes, even when I am successful living the life of a transgender woman in a space I had always could ever dream of, I wonder if I am merely an impostor.

Am I taking the place of another cis-woman who could be living in my place? And did I deserve to be there. Then, I come to my senses and think no, all of that is crazy. Instead of taking another woman's place, I was replacing a man who did not approve of his lifestyle at all and wanted to change it. The only displacing I was doing came at the expense of myself.

I certainly paid my dues learning what I needed to do to complete the process. My life was made up of too many blind corners to count. Once I conquered one blind corner, seemingly another would magically appear. Many, I had no idea of what I needed to face to move forward. When I did become relatively successful in my quest to change my gender, perhaps the cruelest joke at all came along. It happened when I began to suffer what is called "impostor syndrome" or ending up in the middle of a girls night out party feeling as if I was out of place. Finally, I overcame my reservations and was able to enjoy myself. I deserved to be there as much as the next woman and I was not displacing anyone. 

Sadly, there were more blind corners than I can remember but I managed to keep my life together and proceed as fast as I could. I still had too many self destructive moments. Mostly, when I did all I could to try to out myself and ruin all I knew of my male life. I drove too fast and drank way too much and even went into the restaurant I managed cross dressed because I thought I could get away with it. Long story short, I didn't and I put my very good employment in jeopardy. I wasn't satisfied going to the established venues I was going to out of town and wanted more and more. All along, I was doing more and more and didn't realize it. I needed to learn all the nuances of being a successful transgender woman in the world but wasn't patient enough to do it. Mainly, my communication skills in all the various worldly situations I could put myself in needed improvement. 

It was frustrating when I thought life was good and the idea of me being a gender impostor snuck in. Why was I out in the world trying to be a woman in a space inhabited by cis women. Many of whom did not appreciate my being in their world. I developed a thick skin over time and finally decided the women who did not like me for no apparent reason (other than the obvious) had problems of their own which did not include me. Once I developed my thick shell, my confidence as a transgender woman increased and life was better.

After a lifetime of experience, I made it out of my own head and into the world. When I did, I was able to put any ideas of trans displacement behind me. In no way was I an impostor and I had earned my position as a woman as much as any other cis-woman. Females aren't women at birth and they are socialized into the experience the same as I was. I just happened to take another path. One of which often gave me more insight into life because I lived a life on both sides of the gender border. I even found myself giving advice to other women on how to communicate better with their men. I was flattered and any idea of me being a gender impostor began to disappear. 

At the same time, I finally stopped encountering any idea of displacement and went on living my dream life I never thought I would ever get to. It was always my impossible dream to live as a woman (trans or not) and I began to ignore the naysayers. Life became more livable and pleasurable and all imposters turned out to be other women in my world.

Friday, May 24, 2024

It was All so Natural

Image from the Jessie Hart Archives. 

Even though I was facing tremendous hurdles as a cross dresser and/or novice transgender woman, everytime when gender times became tough, I kept on trying. Mainly because deep down  I felt so natural when I was cross dressed head to toe as a girl my age.

Although the time I was cross dressed felt so good, the length of time I was able to do it was never enough. Had I had more knowledge back then, I would have realized I was a transgender person. A big difference to me from only being a part-time male who enjoyed cross dressing in women's clothes. As I discovered more and more about myself, I discovered I was a woman cross dressing as a man during the majority of my life. I only knew I was not enjoying or was being fulfilled as a guy. The whole lifestyle never felt natural to me. 

As time went by, I increasingly followed the natural path no matter how difficult it proved to be. More often or not, I encountered very many severe twists and turns. Again, I was encouraged by the natural moments I experienced when I finally encountered the public as a trans woman. It was like the path had big sign boards along the way with directions on how to proceed. Or once I made it to a certain spot in my new gender life, I could set new goals. The example I always use was when I started to progress past just going shopping in clothing stores where they didn't care if I was a man dressed as a woman or not (because my money was green) and began to challenge myself in restaurants where I needed to interact one on one with the serving staff.  

From there, my goals became to refine and test my restroom skills if nature called during one of my longer outings. It was during some of my restroom visits when I  really needed to feel natural and spread my gender wings. I found out quickly I needed to be able to look other women in the eye and smile even though I was very scared. 

Through it all, I lived and was able to move forward towards new enticing goals of living life as a transgender woman. It was during this period of my life when I began to seriously consider moving forward with gender affirming hormones. Sadly, my second wife was very much against any idea of me being on hormones saying if she had wanted to marry a woman, she would have looked for one. In other words, she didn't sign up to live with another woman, trans or not. I loved her deeply and no matter how difficult it was, I tried to honor her wishes until her untimely death after we had been married twenty five years. 

Her rejection of any idea of me moving forward with HRT just put an extra strain on my mental health which in turn, led to a suicide attempt. Following the attempt, I tried yet another "purge" of my feminine wardrobe which of course didn't work. It wasn't too long after my final purge, she passed away very suddenly from a massive heart attack. As I write about often, her death was the ultimate shock to my system because I was always so self destructive there was no way I thought I would out-live her but I did.

When I did, I decided it was time to live my dream of being a full-time transgender woman. I took the natural path and never looked back.  

Thursday, May 23, 2024

Not the Only One

My Transgender Friend Racquel
from Texas

This is really an extension of yesterday's post. During the post I mentioned the times when I discovered there were actually others who shared my cross dressing dreams. In fact, they even had a label back in those days, we were called transvestites. 

In my post I even mentioned the "Transvestia" publication which I came to cherish so much. I was so amazed to see a nationwide network of like minded individuals. In a short period of time, I discovered a side group of sorts called the "Tri-Ess" organization for strictly heterosexual cross dressers who met in nearby Columbus, Ohio for socials or mixers. Columbus was only approximately a half hour from my home and I just had to check it out.

When I did, I was able to meet a smaller, diverse side group who had private parties in an exclusive Columbus location. As I became a part of this group, I really found how I was not the only one. The only issue I had was, deciding what exactly I was. I knew from experience I was much more serious about being a cross dresser than many of the others I met at the mixers. On the other hand, I still wasn't sure if I was as serious as a few of the transsexual women who were headed for gender realignment surgery. Or sex change as it was known back then. I still had too many huge gender decisions to make before I could ever make such a life changing choice. 

In the short term, I decided to align myself as close as I could with the transsexuals as I attempted to learn as much as I could about their lives. I only really knew two, so contact was very rare plus on most occasions my second wife was with me so I needed to be careful about how I acted. 

As the internet and social media came into play, the potential of knowing I was not the only one in the world with gender issues literally exploded. Along with the internet came a new understanding of the different layers of gender life. As I said in yesterday's post, the term transgender became increasingly known here in Ohio, which as always behind the East and West coasts. As I studied it, the more I was convinced transgender fit my status in life and I felt better for a short amount of time. I say a short period, because in no time at all, I was striving to be a better trans person and learn more and more about myself in the world.  

What I did learn was, even though I found others who shared my gender issues or even gender dysphoria, there were not many. In fact, before she moved to Texas, my friend Racquel was one of the few women in the LGBTQ world I stayed in contact with and Racquel often joined in with my lesbian friends when we partied. 

Recently, partially because of my mobility issues, my transgender outreach has been limited to my writing as well as virtual diversity meetings with the local Cincinnati Alzheimer's Association. As well as the occasional speaking engagement thanks to a friend in the trans community. When I am able to participate in an outreach, particularly to young people, I am able to see I am far from being the only one with gender issues and it feels good.  

Wednesday, May 22, 2024

Gender Boxes

Image from the Jessie
Hart Archives.

When I was very young, my parents did what so many others do. They constructed a gender box and forced me into it.

As I grew up, I had no choice. I was a boy and was expected to do boy things. Even to the point of receiving gifts on Christmas I did not really want. My primary example came one year when I secretly wanted a doll or kitchen set and I received a BB Gun instead. I was the opposite from the "Ralphie" character in the "Christmas Story" movie. For you that don't know, Ralphie wanted a BB Gun in the movie in the worst way.

 As I grew and began to gain confidence in cross dressing as a girl, my gender box became smaller and smaller.  On most days, it was a struggle to just exist in the world as I knew it. The worst part about it was I never had a choice. It was like I was a round peg being driven into a square hole and being told to like it. I didn't like it and my struggles led to a worsening of my gender dysphoria and mental health. Perhaps the worst part about my situation in those days was I had no one to talk to about it and knew no one with similar gender issues. I was so alone in my little gender box.

As I struggled forward in life, I discovered there were others who were in their own gender boxes and struggling with similar problems also. I like to refer to those days as my "Virginia Prince" and "Transvestia Magazine" days. First I could not believe there were so many other cross dressers in the world and they even had a regular publication I could subscribe to. Looking back, I think "Transvestia" came every two months and I could not wait until I received my new issue. Just reading and gazing at all the other pretty transvestites in the issue made living in my box a bit more bearable. Especially when I learned there were regular "socials or mixers" being held in a location I could actually drive to. I was dazzled when I went to my first mixer and saw all the different people who attended. All the way from weekend cross dressers to transsexuals' heading for gender surgeries. 

Even seeing all those different people in their own little boxes did not help me with mine. Deep down I knew I still didn't fit in with most of the cross dressers I met because I was way more serious and certainly not with the transsexuals because I wasn't serious enough. So I remained in my little box, mainly trapped until the transgender term made it's way into the mainstream consciousness in Ohio. Once I heard or saw transgender, I knew it described me better than anything I had ever seen. Finally, I could take a big marker and write proudly transgender on my box.

From there, it was a matter of connecting the dots and removing the box altogether from my existence. Of course, learning to live a new life as a new gender was a major process and not one which was to be taken lightly. To make matters worse, sometimes I tried to jump into new gender boxes and missed my step and had to retreat to try again. Even still, life had taught me by this time, nothing was going to be easy when it came to escaping being pounded into the square hole I was in but when I did, I could be happy. 

I was fortunate in that I lived long enough to escape my gender box and enjoy a new world as a transgender woman free from many worries I used to have. The process was difficult but worth it.  

Saturday, May 18, 2024

Flashing a Trans Girl

From the Archives. Club Diversity
Columbus, Ohio.

Before you think I am preparing to write a post about me "flashing" another person. No my skirt was not too short or anything else on that occasion. I was wearing my typical fall fashion, boots, jeans and sweater. 

In truth and as boring as it may seem, the only person  who was flashed was me and I don't think anyone else noticed. At least, I hoped not. As it was, my flash occurred just after I increased my dosage of gender affirming hormones. On the evening in question, I was out doing what I normally did, trying to enjoy myself with a drink at one of the venues I regularly went to. 

Suddenly out of the clear blue sky, I felt my face flush and I felt as if I was internally combusting. As I attempted to slyly look at the patrons around me, I was surprised and please to note, no one was rushing towards me with a coat or blanket wanting to put out the flames. Then, as quickly as it came on, my first hot flash as a transgender woman was over and I went back to my drink. I can not say the whole experience was as unpleasant as much as it was unexpected. Up to that point, my gender affirming hormones had ushered me into the second puberty of my life...a feminine one. 

While I could not go back and totally erase all the unwanted benefits of my first puberty which I called testosterone poisoning, my new HRT could help me into a new world. As my breasts and hair grew, my skin softened, along with my facial contours. Not having to wear wigs anymore as well as using less makeup helped my feminization in the public's eye as well as giving me a new found confidence. What I missed the most was having anyone to talk to about my second puberty. When I did bring up the facets of changes I was going through, my female friends just said welcome to their world. Little did they know how long and how much I wanted to be in their world. 

Up to the point of my flash, I had never cried in my life, even during the passing of both of my parents. The best way to describe the new me who could cry was when my testosterone was driven down, the hard edges were taken off my life. All of a sudden, my first good cry occurred one evening when a thunderstorm rolled through my Ohio town and I quietly mourned the loss of my male self. I took no real pity and for the first time, I was able to understand the difference between a good cry and a bad one.

As you can imagine, I was elated with the results of my second puberty in life which did not occur until I was in my sixties. Even though, if I had it all to do over again and transition earlier, I would not have wanted to miss out on the times of accomplishment and fun I had carved out as my old male self. He had taken me a long way in life on a basically successful journey which gave me highlights of having a daughter who supports me to this day, all the way to living with wives/women who helped me unknowingly be a better transgender woman. 

In a nutshell, very few humans have the opportunity to go back and try again. By going through a second puberty and flashing myself, I had the rare chance to not screw it up and be a better person. While I consider my hot flash learning experience as one of the top moments in my life, I also consider the process part of my passage into my unique womanhood. Not unlike having a mammogram. I am just glad, no one else noticed I was on fire one minute and reaching for my coat the second because my thermostat was broken and I was freezing. All part of my second puberty.

See, I told you this post wasn't going to be part of a sensual flash in anyway. Sorry! 

Friday, May 17, 2024

Mansplaining a Trans Girl

Woman being 
mansplained by Al Eimes
on Unsplash .

First, mansplaining to me is a highly insulting way to communicate with women and one I tried my best not to do before I transitioned into the world of a transgender woman. 

In fact I think I went out of the way to not mansplain anything to the women I worked and lived around. I hope now it wasn't noticeable and I was coming off as dismissal. Regardless, I did my best until I was admitted behind the gender curtain and was able to see how the female half lived. 

The problem was, I took so many years to get to the point of being allowed to look behind the curtain and play in the girl's sandbox. So I never quite understood what the mansplaining fuss was all about, until it slapped me one night in a regular venue I was accepted in. What happened was somehow I became part of a small group of men discussing a topic I knew a lot about, like sports. I was still new to the system and tried to interject my thoughts into the conversation. Just as I would have as my male self. To my surprise, I was rudely ignored by the men and I quickly left and went on my way. The whole process was another of my life changing moments when I was transitioning. 

I didn't know what I was expecting since I had seen mansplaining all my life from other men around me when they interacted with women. Why would I be any different? Well, I wasn't and the better my presentation as a transgender woman became, the more I was talked down to. It was like I had lost most of my intelligence and all my life time experiences in addition to other male privileges. 

Quickly I learned to play the game of being a dumb blond, which I was most of the time back in those days. A prime example came one night when my car broke down and I had to call a tow truck. As luck would have it, a well meaning policeman showed up to help and between the driver and the cop figured out the best route to get my car home without even asking me. I was infuriated until the whole evening declined even farther when the tow driver started to explain to me how his wrecker worked. on the ride back Finally, I relaxed and started to ask him questions about what his wife packed him for dinner and why were wheels round. (Just kidding.) But I tried to make the questions of my status as a woman for him which was obviously very low. 

Maybe I should have been happy I presented so well that I lost a main part of myself forever. I learned how women are really treated and prepared myself for other gender lessons. The main one I write about often is the loss of personal security I witnessed up close and personal when I transitioned. I learned to park in the most well lit and safest places I could with the shortest walk to wherever I was going, to name one important point. For the first time in my life, I was the prey when I was out in the public's eye and it was quite the change.

Slowly but surely on the rare occasions I needed to communicate with a man, I learned to draw from my personal experiences and understand where he was coming from. I waited for him to come to me and interject my ideas when I could as a transgender woman. By doing so, I was able to build my confidence back up in public. 

Today when I am mansplained, I take it with a grain of salt because I know there are plenty of women who reverse the process with their communication with men. I remember several nights when I was fine with talking to the woman in a couple I didn't know and having it all change in a flash when he started to show any interest at all in me. There was no womansplaining going on as I instantly knew where I stood. It also never took me long to understand all the non-verbal cues women use to signal each other. 

 It is one of the reasons both binary genders have such a difficult time of communicating. Upper level understanding of the genders is one of the rare benefits of being transgender and should be embraced. When you can do it, you truly have the chance to advance as a human. 

Thursday, May 16, 2024

On the Transgender Precipice


Image from Wira Dyatmika on

As I followed a winding, difficult path to my dream of living as a fulltime transgender woman, I took years to climb the gender mountain.

Just one of the problems was  I was afraid of heights. The higher I climbed the rarer the air became because I had never been in all the situations I encountered. As I entered the world as a trans woman, there were so many situations I never expected to happen. I knew women led multi layered lives but not to the extent I encountered. Initially I thought if I had conquered all the fashion, hair and makeup basics, I had it made in the world. Needless to say, I was wrong. 

Even though my male self contributed to me feeling petrified as I climbed, I kept going. As I decided to leave the male gay venues I was going to and try lesbian and straight bars, I really needed to climb to a new level to survive. When I reached a new level, I paused to look around and see what I had accomplished if anything. What I did accomplish was a degree of acceptance from the venues I went to. Except for one evening when three guys kept playing "Dude Looks Like a Lady" on the jukebox over and over again, I begrudgingly held my spot and became an accepted regular in several places. As I did, my view of the world as a transgender woman became clearer and clearer. My gender dysphoric fog was clearing and increasingly all I could see was a future life living as a woman. 

At the same time, I was still a regular at the diverse mixers in Columbus, Ohio where I met a total range of people from cross dressers to transsexual women who were headed for gender realignment surgery or a sex change as it was known back then. By meeting and learning from all these people, I was able to chart my own path to my transgender precipice. 

The two main things I remember are how desperate I was for information on my gender issues and how scared I was of receiving an answer. Was my therapist right and I could do nothing about my feminine desires? If so, I had reached a precipice in my life and I needed to make a decision which would change my life forever. Of course my spoiler alert is, from my gender view, I could see a wonderful if not difficult future ahead as a trans woman. What happened was, as I built a new circle of women friends who never knew me as my past male self, I kept pushing and pushing myself to the edge of my transgender precipice until I fell down the cliff. 

Unknowingly, for the most part, I had set myself up for a soft gender landing. I gave away the remainder of my male clothes and set out to quit climbing and live a new life. What a relief it was to stop expending all the energy I was using to live two gender lives. The process exhausted me and ruined my fragile mental health. My friends helped me through this difficult time of my life more than I can ever say.

With my fears of gender heights behind me, I met my wife Liz and she helped me seal the deal and live my life as a transgender woman. That was fourteen years ago and we have been happy ever since. I don't think I could have ever envisioned I would meet up and marry another woman in my long life but I did. I guess the fog on my mountain was hiding my future.  

Wednesday, May 15, 2024

Transgender Reconnections


Image from the
Jessie Hart

As I followed the path to a transgender transition, I made several important reconnections. 

Little did I know or realize how many twists and turns I would take before I found my truth. Most importantly I needed to realize I was not a man cross dressing as a woman, I was the reverse. A woman trying to make it as a cross dressed man in life. Because of that, nothing seemed to quite fit in my life as I struggled to survive in an unwanted male world. As I attempted to outrun all my problems,  I drank alcohol to excess as well as moved around and changed jobs way too much. I was always running, searching for my transgender reconnections. Sadly, I searched for nearly a half a century before I was able to have any success and connect with my authentic gender self.

During all those years, I was teased with success as I left my cross dressing mirror and slowly entered the world as a novice transgender woman. Along the way, I made all the mistakes I could think of plus some I could not have imagined happening. In my haste to reach the conclusion to my reconnection, I needed to first discover what it was. Through it all, my inner female was screaming at me for more and more attention but my male self did his best to play all his cards and hang on. The game they were playing wrecked havoc with my mental health and I sought out therapy for help. As with anything else, therapy is what you put into it and I went through several very good therapists as well as a couple not so good ones. Then there was the problem of me listening to what they had to say to start with because my male self was telling me therapy was just a waste of time and money. On the other hand, my female self saw the benefits, especially if the therapy process was slowly opening her world at all. 

Sometimes too, reconnections were tantalizingly close. There were so many days or nights when I could relax and enjoy a glimpse of what a life as a transgender woman could be like. The more reconnections with a feminine world I could make, the more natural and better I felt. Probably, most importantly, all of the gender progress I was making was because I believed in myself and my confidence was building. I had escaped the basic confines of the wardrobe and makeup challenges and made it to the one on one communications I was suddenly faced with as a trans woman. It was during this point of my transgender reconnection process I learned the most. Mainly because, I was relaxing and letting my long hidden female self take over. It turns out all those years of having to quietly sit back and watch my male self struggle enabled her to be a better person when she got the chance. 

When I reconnected with my female self, I was able to be a full person again and I knew one of my therapists said it right when she told me there was nothing either of us could go about me wanting to be a woman. If I had followed her advice and set out to discover what my second wife had told me all along, I would have taken the time and really looked into what a women's world was all about. Other than the outward appearances of fashion and makeup. It was the biggest reconnection I couldn't make until I had earned it by actually adopting and living a life as a trans woman. Even to the point of beginning HRT or gender affirming hormones. 

In many ways, the new hormones were the final piece of the puzzle in reconnecting my transgender self to the world. Physically and emotionally I was ready to face the world as a united human being.  

Tuesday, May 14, 2024

Down the Transgender Rabbit Hole


Image from Benoit Baumatin on UnSplash.

Long ago, I sought out a rabbit hole I found I did not want to escape.

In the beginning, I did not go deep into the hole so I could supposedly easily escape if I wanted to. The farther I went, the harder it was to escape even I wanted to. What happened was gender euphoria set in and the entire cross dressing experience became increasingly pleasurable as well as feeling incredibly natural. The problem I faced was how to cover the entrance to my rabbit hole so no one else in my family could discover it. Very early it was easy when I could attempt to borrow select clothes from my Mom's closet which ended when I became too big to wear them. Then I had to rely on my own limited financial resources to buy fashion and makeup accessories. 

For awhile, the pressure to go away and cross dress became so intense I needed to find a spot away from the house to establish another private rabbit hole. I found the best spot in a quiet wooded area next to our rural home. I was able to protect my secret collection of feminine clothes in plastic bags and hope they would be protected enough as well as not be discovered. I did well, because they never were and I was provided another place to go to cross dress. If even for a short period of time. 

The better I became at perfecting the "art" of fashion and makeup, the more I wanted to leave my novice transgender rabbit hole and look around at the world. At first, the world proved to be a very difficult place to be. After too many public failures I was sent scurrying back to my rabbit hole to seek comfort and try to figure out what all I was doing wrong with my feminine presentation. The entire feminization process for me proved to be a difficult one as my entrenched male self fought for his dominance and kept on trying to cover up my rabbit hole with ill advised purges. Very quickly he found out the gender purges I was going through were a complete waste of time and money. 

Once I reached the middle portion of my life, my rabbit hole needed to be expanded from a crossdresser rabbit hole into one large enough to contain a full fledged transgender woman. I needed room for more wigs, shoes and women's essentials to survive in the world. As I was entering a new exciting yet scary world without my white male privilege, the sunlight outside my rabbit hole was at times blinding. Even more so when the world all of a sudden expected me to communicate with them when at the least, I had to order face to face with servers or bar staff trying to take my order. What was a novice trans woman to do? What I attempted to do was make the best of a potential destructive situation. Very early in the game, I came to the conclusion the world knew I was transgender for the most part and those who cared, could just get over it because I was just living my truth.

Of course, once I was able to leave my rabbit hole in my past and live, I had no desire to go back to it's dark confines. Each time I was successful in the feminine world, my male self lost more and more of any control he had left. 

The writing was on the rabbit hole wall when I started gender affirming hormones. I knew I had made the correct decision when my body and mind took to the new hormones so naturally. In addition to all the bodily changes which took place, I cherished the new emotions I felt. Being able to cry for the first time in my life was quite the experience. 

Perhaps, most importantly, was when I discovered the lack of predators I really had when I left my rabbit hole. Of course dealing with the occasional man was a problem but with my circle of lesbian women friends, not so much as they taught me true validation as a person. Once I learned to validate myself, I was freed from my old male rabbit hole for good and jumped into the sunlight.

Sink or Swim

Image from Trans Wellness Event.  Jessie Hart Archives.  Many times when I first entered the world as a new cross dresser or femininized mal...