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

Sunday, July 17, 2022

Lessons Learned

"Club" Photo Courtesy Cyrsti Hart 

Years ago there used to be a venue in Dayton, Ohio called "Celebrity". It was a huge converted super club which I happened to patronize a couple of times when I took a date to a prom. 

Years passed by and I advanced my feminine technique far enough I couldn't wait to make the short trip to return. When I did make it, I was fascinated with all the opportunities.  The club featured a wide variety of gay men to drag queens to cross dressers and the occasional sprinkling in of "admirers" or those men who desired men dressed as women. 

Perhaps the earliest lesson I learned was how different I was from the drag queens who frequented the venue. While many were totally attractive there were just as many who came off as caricatures of cis-women. 

Through it all, I was intrigued by the attention I received from the occasional admirer. Mostly they wanted me to shoot pool with them. Probably so they could watch me navigate the table in my short tight mini skirt I was fond of wearing. Back in those days I felt trashy or so called sexy clothing was the way to validate myself as a woman. Plus everyone told me I had great legs, why not take advantage in the way I felt. The problem arose when I had to learn to wear the mini skirts. I found out one night first hand when a man insisted I watch their game when I refused to actually play. He pulled up what amounted to no more than a bar stool for me to perch on during the pool match. It only worked for a short time until I became uncomfortable and moved on. 

All in all the whole experience left me mostly confused. I was in the early stages of realizing I wasn't looking from attention from a man but loved it when it came from a woman. It was rare there were any other lesbians in the venue so I had very few opportunities to find any other women to attempt to interact with. 

Celebrity Signage

There were a few other cross dressers and/or transgender women who frequented the venue. Many of them were from a Dayton group who were decidedly unfriendly. So I left them alone. Another lesson learned. Just because others shared my desire to be feminine didn't mean their attitudes changed for the better. 

Most likely the highlight of going to the venue had to do with using the ladies room. When I did, I was fairly sure the décor hadn't changed since my prom date did years before. For whatever reason, the experience made up for my other resentments. after all  she was the one who was able to wear the beautiful dress and wear the fresh corsage. 

The whole experience helped me to grow past the initial steps of coming out in a feminine world. Little did I know then how many more there were to come.  

Tuesday, July 12, 2022

Such a Day

I have written numerous times on how I am retired and don't live a particularly active lifestyle. All of that changed yesterday. Seemingly the heavens ganged up on me and made sure everything came about on what would have been a lazy Monday. 

Photo Credit Jessie Hart

Everything started when I learned the closing paperwork on the final property I owned in my past was put off until later in the day. Four o clock to be precise. On the plus side, the timing gave my partner Liz and I a chance to stop in one of favorite villages on the way to the town my property was in. Plus, as luck would have it, yesterday was also the birthday (15) of my youngest grandson, so we could all meet for lunch. The village we were meeting in is known for it's liberal background and pro LGBTQ stances so I was looking forward to seeing my daughter and grandson while we enjoyed a light lunch. 

From there Liz and I had time to do a little shopping in a couple of the shops she has enjoyed going to over the years. Since the village is approximately an hour and a half drive from our house, it's not as if it is an easy trip to take. 

Another pleasant surprise was another small town along the way was having a real live gas war and we were able to refill our tank for nearly fifty cents a gallon less than we paid that same morning when we left. 

Even though we were taking our time, we still had plenty of time to waste once we arrived in my ex home town which over the years was ravaged by de-industrialization and has yet to recover. As we "toured" all the old places I remember were still there and nothing much had improved. Regardless of all of that, time seemed to be moving so slow as I approached a situation where I knew I would be forced to face my former life as a cross dressing man. I also knew it was past time to do something about it and cut my final ties to my past. 

As we walked into the title office where the paperwork was to be handled, I felt as if I was moving in slow motion. I did manage to pull my drivers license out of my purse without dropping it on the floor and not stutter. Having that success, it was time to be mis gendered and get on with the process of signing a ton of paper work. 

Fortunately I had my gender warrior with me and she forcefully corrected the buyer or the paperwork clerk when they tried to call me "sir". Ironically the major memories the clerk had of the building I used to own was the Christmas decorations my deceased wife used to obsess on every year. It was difficult for me to have to relive the memories of her and explain to the buyer why he has found so many garden articles in the building I used to own.  My wife also had a major love of gardening.

In seconds which seemed like hours it was all done and I finally had my check.

For some reason, Liz wanted to stop at Wendy's and try a strawberry Frosty so I had to brave a decidedly conservative public again plus use the ladies room. Which I was able to do relatively unscathed meaning I survived with just a few stares.

As we headed home, I decided to treat Liz to a dinner at our favorite restaurant. Exhausted, we finished a great dinner and a margarita and headed home. 

It was such a day, my past has finally been physically severed. Now it's even a better chance to build a better future.  

Thursday, June 30, 2022

Parental Guidance

Can you imagine your transgender life if years ago you had the benefit of positive feedback from your parents? 

Photo from Noah Busher
on Unslash, Not of the author.

Most certainly it didn't happen with me. My parents  of the "greatest generation" age group did not have the knowledge tools and/or the emotional background to handle a gender dysphoric child. You have to remember also I was born in 1949 which lends a reference to the time period I am referring to. I can't speculate on what my Dad may have thought since I never had the courage to tell him. As I have mentioned many times, the only time I told my Mom was when I was out of the Army and she told me they would help me with psychiatric care. I found the whole idea to be totally wrong and distasteful to me because not long ago I had come out to a few close friends as a transvestite. I found the experience to be totally liberating and the last thing I wanted to do was go back. In typical form, the night we talked was the last time Mom and I discussed my gender issues the rest of her life.

So I can't even imagine having the opportunity to have been "Daddy's little girl" Or being able to play in my Mom's makeup without the fear of being in trouble. What if I was allowed to receive the doll I wanted as a gift for Christmas instead of the hated BB Gun. Furthermore what if I had benefited from the guidance a mother can offer to a daughter growing up. Could I have separated the good from the intense pressure I am sure I would have encountered as Mom wanted me to conform. It was bad enough as a cross dressing  boy. I am sure the grass would not have been always greener on the other side of the binary gender pasture. 

The other day when my daughter and I were enjoying breakfast, she asked me if I had always known I was transgender. I told her, from all indications yes. The problem was the knowledge of the term or even the invention of the word itself was far from being a household term when I was growing up. The whole idea was so foreign to me it took years to figure out yes indeed I checked all the transgender boxes and finally I had found something which I felt as if it fit me. 

I don't really know why but even with her complete acceptance I still am slightly shy when she asked me questions concerning my gender issues. Possibly it is because a portion of me still doesn't pull back the macho man curtain to her and let her see the true me. One of the remnants of what my Dad taught me. 

These days I am so envious of the transgender youth who are fortunate enough to have understanding parents. Some to the point of even being willing to move to areas of the country which are more transgender friendly. This extends to all the sympathetic spouses who are willing to transition with their loved ones. 

Definitely positive parental guidance should be praised and cherished.     


Wednesday, June 29, 2022


 What are friends for? Right? As far as transgender individuals are concerned, friends mean quite a bit. 

Many of us go through a portion of our lives when we desperately seek out "replacement" friends to help us with how we look or even how we move as we attempt to live as our authentic selves. I remember many times in the blog when others have mentioned how badly they needed a cis woman to do their makeup. Over the years I found I was mostly self taught which sometimes showed until I learned how to not look like a clown. I say mostly because on a couple of occasions I did take advantage of a free makeover. Even then with my ego, I had to "face" the makeup person with absolutely no make up and more importantly try to understand exactly what he was trying to tell me about applying makeup.

Years before I sought professional help, I did beg my fiancé to help me totally cross dress as a woman. It turned out to be one of the most exciting times of my life yet one of the worst decisions I ever made. Later on I had to endure a very messy breakup with her before I went into the military. She told me to tell them I was gay and not be drafted or we were finished. It turns out she was holding my cross dressing desires against me. The wonderful end to the story is getting rid of her was one of the best decisions of my life. 

These days there are many ways to seek out help with cosmetics. Depending upon your finances, there are larger makeup chain stores to help you. I say finances because naturally, they will try to sell you many products. Some of which you may not need. 

Girls Night Out Photo. Courtesy Jessie Hart 
I am bottom row far left. 
Of course there are many other ways friends can help you down your path to living as your authentic self. I was fortunate to find several close cis women friends early in my transition when I was going out to be alone. In other words, I was desperately lonely so I still went out as my authentic self to enjoy what I had of life. Also I had recently gone through the loss (death) of my wife and several close friends, so I felt what else did I have to lose. 

My new found friends helped me to find life again and more importantly accepted me as my authentic self. As with most everything else in life, time moves everything in a circle if you live long enough. In my case I was able to finally replace the few long time friends I had acquired as a cross dressing man with equally as close friends I could socialize with. Being social again brought my life back to a place I could ever imagine.  

Transitioning certainly means more than coming out to family. No matter if you are able to find new friends through local LGBTQ groups or wherever, establishing a new world as your authentic self is often key to a healthy existence. 

Sunday, June 26, 2022

Transgender Bravery

 Some individuals call a transgender persons path to achieving living as their authentic self with terms such as bravery or even courage. Over the years I have been more likely to refer to me following my path as one of bravery rather than courage.

Courage I rather use to describe service members and/or first responders. It takes real courage to do what they do. On the other hand it takes bravery to take the first steps out of our tightly closed gender closets. For some, including me when the unbelievable pressure began to weigh on me, I just had to take steps to relieve the gender stress. If I didn't I would be nearly unbearable to be around. In fact my wife became quite adept at knowing what I was feeling and why. Most of the time all of it was a good thing except when I was suffering extreme gender dysphoria. She naturally became upset when everything she was doing was never enough. Sadly it never was. No matter what she did to give in to my cross dressing urges, she always drew the line at any suggestion of me being transgender. 

What happened was I increasingly pushed my gender boundary which led to possible discovery by family friends. When I was emboldened to do it, I guess you could say I became brave enough to leave the house and attempt to live a life as a transgender woman. An example was the night she was working and under the cover of darkness, I took off in my favorite oversize cuddly sweater, leggings and boots to take it a local Christmas light display which needed to be enjoyed on foot. The entire evening proved to be very successful as I even enjoyed a cup of hot chocolate I was brave enough to stop and order.

Then there were all times I gave up on the male gay bar venues I was being rejected in and started to explore going to larger straight venues. Sure I was scared but I wanted to see if I could be accepted as my new authentic self. As a began to go down this new path I needed to be very brave to have any success because I was scared to death. 

So, all in all I will accept the bravery comment. Mainly because I think it shows what I needed to go through to arrive at where I am today. There were so many times I thought living life as a full time transgender woman was definitely an impossible dream. During my brief time in the military during the Army drills we went through I learned what courage could be about. I learned to think courage was an intangible which showed up (or didn't) during times of great duress.  

Whatever you decide to describe yourself as, courageous or brave, basically we are dealing in semantics. Your transgender journey is yours alone and will never be described as an easy one.  

Saturday, June 18, 2022


 My experiences with therapy started years ago. So long ago I barely remember when. However I do remember I built up the courage to tell my first therapist (a man) that I liked to cross dress as a woman. I remember too he basically glossed over my admission and began to write me prescriptions for such mind altering medications of the day such as Prozac and Lithium.  I don't remember much about the

Jessie with Brutus Buckeye

side effects of Prozac but I know I didn't like or tolerate Lithium well at all. Through it all, the medications didn't have an affect one way or another on my cross dressing. Plus, I felt the doctor must have felt worse talking about it than I did, because he never brought it up again.

Around that time was when I picked up my small family and began to move to various places around the country trying desperately to out run my gender problems. Following a year and a half stay in the NYC Metro area, we bounced back to our native Ohio, to a largely rural area along the Ohio River.  Near that time was when I began to seriously explore the world as a cross dressing woman. My wife knew of my cross dressing desires but never approved of me going out from our house which happened to be in a very rural area. Of course, the more I snuck out the more I wanted to. Which led me to being on a collision course with being caught by her. Every time it happened a huge fight between us took place. One time after a particular nasty altercation, I volunteered to schedule an appointment with a therapist who specialized in gender difficulties or dysphoria, I believe I discovered her information in an issue of "Transvestia" magazine. To do it at all was quite a task because of where she was located an hours drive north of us in Columbus, Ohio. 

Ironically she was a successful trip for all the wrong reasons. Fairly early in our visits, she told me there was no way she could help me with being a cross dresser or transvestite as it was known back in those days but she could help me with the vicious mood swings I was going through. In other words, she was the first therapist to diagnose my Bi-Polar disorder. Through it all, every visit I managed to take, I was prolonging the inevitable next fight with my wife. So all in all, my experience with this therapist was a success. At least the next time I was caught out and about cross dressed by my wife I could say I was trying to do something about it.

My next experience with a therapist came years later when I began my care under the Veterans Administration health care system. One of the main reasons I sought out their help was because I was severely financially challenged and unable to purchase my Bi-Polar medications on my own. Of course in order to be prescribed through the VA I had to be seen by a therapist. This was near the same time my wife had passed away and I was considering starting hormone replacement therapy, so in essence invisible doors were beginning to open for me since this was all in the early days of the VA accepting HRT work also. 

I was really fortunate. The therapist I was assigned is still with me today. A near impossibility in the VA system as I know it. More importantly too, she was willing to listen to me and accept the fact my transgender issues were completely separate from my Bi-Polar issues. She kept me on the medications which had been a success for me in the past and approved me for HRT meds. Fairly quickly she became one of the most important people in my life.

I am aware I could be the exception to the rule when it comes to therapy and many transgender persons resent the idea they need therapy before they can start HRT.  I know also several trans persons who either had a difficult time finding a therapist who deals with gender issues or being able to feel comfortable doing it. 

Hopefully if you have sought out therapy you have been successful finding one who helps you with your gender dysphoria or any other issue you may have,   

Wednesday, June 15, 2022

Transgender to the Core

 When I was first beginning to open my cross dressing closet and see what the world had to offer, one of the main questions I was asked was when did I know I was transgender. Overall it seemed like a simple question that wasn't. 

Photo courtesy Jessie Hart 

First of all, the basic answer to the transgender question is I have been trans since birth. In fact though there are so many layers to this question. In order to answer it, I would have to attempt to explain the differences in being a cross dresser versus being transgender. To me, I spent the majority of my life cross dressing. Mostly as a man which totally confused most who bothered to care enough to inquire into my gender issues. It was difficult to explain why I was so sure I was never really a man, I was just going through the motions. Even though I attempted to balance all my gender issues for over fifty years, I became very adept at fooling the world. Sadly I was mainly only fooling myself. 

For some reason, in my mind something snapped and I decided when it was time to move on from being a cross dresser. To me, the major difference was doing my best to look like a woman versus exploring the world to see if I could follow my dream and live full time. 

As I went down this gender path, it became increasingly evident I could live full time as a transgender woman, Why? Because I sought out and found a small group of women friends who accepted me for who I was. Through the entire process, deep down I felt so natural. I have written a number of times of how a huge weight was lifted from my shoulders. 

These days, I don't get asked questions concerning my gender much to not at all. I think it is because I have become so comfortable as my authentic self. I don't have anything to prove to anyone and if they don't accept me, so be it. I'm also fortunate to nearly always having my partner Liz by my side. In ways she doesn't understand she runs interference if I happen to encounter anyone negatively questioning my gender, 

As you can tell, I don't have any easy answers for anyone who wants to positively question my gender journey. It is confusing enough to try to explain my idea of why a cross dresser and a transgender person differ. In fact, there were many times when I started what I referred to as my second transition to a trans woman, I was wondering what I was doing. I had so much to lose such as family, friends and jobs. What kept me going through this difficult time was the transgender journey I was going through felt so natural. That alone kept me going.

So if you are thinking of transitioning and have major questions to answer, my only advice is to listen to your inner self. It will tell you if you are transgender to the core. 

Tuesday, June 14, 2022

Missed Time

 One of the major portions of my life I missed out on were when  the parts of my gender dysphoria were  doing battle with each other. Many times my attempts to cross dress as a man totally disrupted my life. I became mean and nearly lost jobs because of my attitude. Ironically, I followed the same pattern over and over again. The internal pressures would build to express my authentic feminine self until I had to find a way to relieve it. I guess the definition of insanity being doing something over and over again while expecting different results applies to me here. 

Photo from Jessie Hart
Over the years also, I built up a strong resentment because I couldn't and didn't live the same lifestyle as the other cis women around me. A prime example was not being able to be given a doll at Christmas for a gift when I disliked the boy gifts I received. Plus at Christmas dinners, I wanted to be the girl in the black velvet dress with white tights and patent leather flats. Not the restrictive shirt and tie I was forced to wear. Not to mention my crew cut or burr haircut. 

Finally I learned there was nothing I could do about the gender pressure I was feeling but to give in. I had paid my dues trying to be a man and it was time to take my chances and establish my life as a transgender woman. From that point forward the pressure of trying to live in both binary genders was released and I felt a giant weight had been lifted from my shoulders. 

Even with all of the new found gender freedom, I still was resentful of all the girl time I missed growing up.  Take applying makeup for example. I suffered because I didn't have the input from my Mom or other girls my age when It came to the art of applying makeup. I struggled through until the times I was actually able to take advantage of a professional makeup artist who was able to produce magical results with what he had to work with. That's right he because I had the best results from a male. 

Then there was the whole dating ritual scene. I was very shy to the point of being afraid of girls and was totally envious of their lifestyle. It wasn't until years later, I found girls had it just as hard as boys, just in different ways. It turned out the gender grass was not always greener on the other side of the binary. Even still none of that helped me when I finally did start dating. Once again I was trapped admiring my dates appearance in all the places we went to. Especially the proms I went to when I was stuck in a restrictive tuxedo when my date was able to look so nice and colorful in her dress,

As we grow older and are fortunate to to be able to live our dreams, it's a total waste of time to dwell on the past unless you are learning from it.  As I wrote earlier in this post, neither primary gender has an easier life than the other. I am just greedy and would like back a portion of the energy I missed out on. How my life could have changed. 

On the other hand, I would have missed out on what turned out to a frenetic lifestyle when it turned out I was just passing through so many people, places and cultures. Finally I was able to shed myself of my former toxic male self. From then on, my missed time was not as important because I was building new ones as my authentic feminine self. 

It all felt so natural to me as I knew playing in the girl's sandbox was where I belonged all long.

Wednesday, June 8, 2022

Gender versus Sexuality

My post yesterday barely touched on the idea of changing your sexuality when you change your gender.

My own over simplification of the process is sex comes from between the legs and gender comes from between the ears. Of course your idea maybe different.  Mine comes from the experiences I went through. In other words, once I went through the process of joining the world as a new transgender woman, all of a sudden I had to figure out what I was going to do about my sexuality. Was I going to attempt to continue to try to date women or try the brave new world of dating men. 

By the time all of this was occurring, I was in my early sixties and was aware (even prepared) to go through the rest of my life alone. However, I was not prepared to stay in my house and not go out and socialize again. Those were the days I was desperately alone and went out to be alone as I called it. These were also the time I went on line to explore the then new dating sites. Predictably I had to weed

On Line Dating 
Photo, Jessie Hart

out tons of crazies as I explored what was out there. "Out there" meant mostly guys who either wanted to wear my undies, treat me as a fetish object or just not show up at all where they were supposed to be. By now you are probably thinking trash in equals trash out. Ironically only most of that was true because I did find my long time partner Liz on line. 

Plus, there were other quality men I did encounter. Several I did manage to meet in the public venues I frequented and enjoyed my times with them. Including my first dinner date with a transgender man I knew. Mostly the dates went as far as good night kisses and a bit of fairly aggressive groping. Far enough I had to wonder what would come next. Or, would this be the time I would lose my "other virginity" to a man. For whatever reason nothing ever happened. To this day one of the men remains friends to me on social media to this day.

The guy I "would have/could have" gone much farther with never tried to do anything else with me but talk. You regulars who read my writings regularly will recognize him as the "motorcycle guy". He is the one I met in one of my regular venues. He came in with a small group of friends who came to accept me as one of their own. He was a big bearded guy who rode a beautiful classic motorcycle. I used to fanaticize about riding on the back of that bike with him. None of that ever happened as he went through a very quick (one week) marriage and often I was the only one who took the time to talk to him We got along very well until all of a sudden he found another job and moved from the area.

With him went the last chance ever, I would spend any real time with a guy. Early on, I was just looking for validation from being accepted as a woman but when the validation came from other women, I found I didn't need a man's approval anyway. Not that there aren't quality guys out there but as any cis woman will tell you they are often very difficult to find. 

As my life has progressed I found my sexuality never changed, but a good person is a good person regardless of their gender.  

Sunday, June 5, 2022

We Got Mail

 Yesterday I wrote a post on what would have happened if I had never transitioned and received several interesting comments, one from Medium the other from Google. The first comes from Jas Martinez:

"Interesting thing about transitioning, like most life changing decisions we first have to get to a place where a change or decision needs to be made. We can look back and be sad we waited for whatever reason. But why be sad? We weren’t ready to transition if we were we would have done it. I should had gone to college, I should have moved west instead of the south, I should have not gotten married the last time and transitioned instead. Shoulda , coulda, woulda is a waste of time. Why we do these exercises of the mind is beyond me, maybe it’s to remind ourselves the fear we had back then was just that fear of uncertainty. We had to arrive in a place in time when the fear of not transitioning was greater than the fear of transitioning. Fear the greatest motivator to do or not do something." 

Thanks for the comment. Indeed, fear is a powerful motivator. I so remember all those days when the primal "fear or flight" idea ruled me during my earliest days of coming out. 

The second comment comes from Connie:

"What if I hadn’t made the move to transition? I’d still be the miserable man I was. No, actually, I’d still be the miserable excuse for a man that I was.How many times have we said that we wouldn’t wish this [gender dysphoria] on anyone? We can repress, suppress, even try to regress it; but it will forever be a part of us. It can be a vacuum, if we let it, sucking from us precious time and energy – a jealous mistress, if you will.

To the outsider, our transitioning may seem to be a giving-in to some sort of mental illness or salacious lifestyle. Some will say that God made man and woman, individually, and that he makes no mistakes. What these people don’t realize – and could never fully understand – is that we, as transgender people, do not need to be told those things, as we will have spent so much time and energy considering those “theories” before making the decision that transition is the right thing to do.

Doing the right thing for oneself does not have to be a selfish act. What can be more selfish is to allow the dysphoria to sap time and energy that could be directed toward loved ones and other positive life endeavors. The trick, I think, is to be as patient with others as we would hope they would be with us. We can never forget that the transition process is not ours alone. Everyone else in our lives must go through a transition along with us. We, of course, have the advantage of having had a lifetime to prepare for it. Not allowing others to adjust at their own pace would be quite selfish, indeed."

Great point! Often it is so difficult to not understand why others aren't so quick to adjust to a transgender person. Especially when adjustment is mistaken for rejection. 

Saturday, June 4, 2022

What If?

 For some reason this morning I was thinking of what would have happened if I had never completed my gender transition from a mildly successful man to a full time transgender woman.

First of all I suffered from extreme gender dysphoria which essentially meant I went through much more dysphoria than I did feeling the gender euphoria which did happen on rare occasions and kept me going. Naturally, my life became increasingly miserable before I made the final decision to live as my authentic self. Much of the misery came from the almost daily mental gyrations I put into what I was going to do concerning my gender issues. 

Liz on right. Photo Courtesy
Jessie Hart

I found not only was I capable of over thinking nearly every problem I have, I could really overthink a gender transition. To the extent of attempting self harm when no solution seemed possible. Now I wonder how I ever could have ever been so blind. Even a poor transition to a feminine world just had to be better than the darkness of death.

One of the main problems I had with changing genders had to do with the perception I was being selfish. As my wife was fond of telling me, she didn't sign up in our relationship to be with another woman. In addition to her, I worried about what other family and friends would think about me. 

Finally, the whole burden was more than I could stand. In a bittersweet way I lost nearly everyone close to me and really only had my daughter and brother to come out to. I through caution to the wind and was accepted by my daughter but rejected by my brother. Suddenly I was aware I had to be selfish to survive. If someone such as my brother thought my whole gender transition was a choice, a phase or worse yet some sort of fetish he was wrong and that was his problem. 

As I thought back, I know now how much I would have missed in my life if I had never completed by trip across the gender frontier. Initially, the trip itself was exciting and terrifying. The farther I went the more I knew I made the right choice. Especially when I learned I could begin hormone replacement therapy. 

Then there were the people I met. I was helped along by more than a few women who showed me the way into their world. My daughter Andrea, my partner Liz and close friend Kim are but a few who come to mind.

In short I am so happy I finally made the jump from not so casual cross dresser to full time transgender woman. I am sad I waited so long and missed so much more life while I suffered. 


Friday, June 3, 2022

Peaks and Valleys

 I used to think crossing the gender frontier was similar to negotiating a maze when you have a series of walls to negotiate. Now I think the entire journey may be similar to climbing very steep hills and then completing the return trip down. The reason being is the severity of what we are attempting. After all, changing ones gender is one of the most difficult journeys a human being can undertake. 

Photo by Hu Chen on Unsplash

As we climb our first hill or even mountain, many times we face the possibility of losing our family, friends and even jobs.  Many times it seems as if we are barely hanging on as we leave lives we were living in often comfortable yet non authentic lives to begin a whole new existence. 

In my case I can understand the idea of holding on to my birth gender for dear life. In fact I worked hard to achieve a quality male life. I had a very good job, fathered a daughter and was honorably discharged from the military. I did many of the guy things everyone did and effectively hid my desire to live a feminine life from everyone I met. So again, it was difficult to let it all go.

Another problem I had with being in the valley once I started my gender transition was being able to see where I was going. Many times I couldn't see the forest for the trees when I was learning a whole new way to live. I found all those years I spent being a cross dresser turned out to be a waste because the entire experience was so shallow. I found the hard way when I started to explore the world as a transgender woman there was so much more to the process than just looking the part. I learned quickly I needed to allow my inner feminine self. I found I had to work surprisingly hard to climb another mountain and establish a whole new feminine personality. Which turned out to be a labor of love. What happened was the more I was out exploring the world as a transgender woman, the more the world (primarily other women) wanted to interact with me. They didn't know it but many times I used them as examples of how I wanted myself to become. My partner Liz put it best when she told me very few people have a chance to re invent themselves totally. Don't screw it up. Which actually I added in to her original comment. 

Over the years I have been fortunate in the number of friends I have found who helped me establish gender base camps as I climbed the mountain peak I am on now. I have copied more than a few and have cherished knowing some of the others. I was so afraid of losing what was left of my male self until they helped me through. 

We all have our own peaks and valleys to negotiate when it comes to our gender journeys. I hope yours goes as smooth as possible,  


Saturday, May 28, 2022

It's a Calling

 On Saturday mornings Liz and I normally watch the CBS morning news show. If you are not familiar, CBS wraps up the show with a musical act. This morning, I noticed the musician refer to her music as a calling of sorts. 

Of course very quickly my mind wondered to being transgender. When was I called to the transgender side of humanity.

My Gender was Calling
I wasn't Listening.
Photo Courtesy Jessie

Was it when I first heard the term in the late 1970's or early 80's, as I vaguely remember. Looking back I do know the terminology resonated with me. Maybe now I had found a label which described my gender dysphoria. I was discovering sadly once again I didn't fit once I began to explore the transvestite mixers I was beginning to attend. In other words, I knew I really didn't fit in with most of the cross dressers in the room and I wasn't ready to think of myself as a full fledged transsexual, as they were known in those days. These were the individuals who were prepared to change everything in their life to change their gender. It was recommended then people who went through a sex change undergo the surgery, then move away and start a completely new life. I was frustrated. I thought I was making huge strides towards understanding my 

gender issues but the end result was once again I was the round peg being pounded into a square hole. Ultimately, being transgender solved my label problem. 

Through all of the early years, the more I explored my gender roots, the more I knew I felt more natural in the feminine world as a transgender woman. More than ever I knew my gender calling was learning how to stop cross dressing as a man and live as my authentic self.

Of course if I was listening, there were plenty of other desperate calls from my authentic self. I can go all the way back when I was exploring my Mom's clothes and makeup as well as purchasing (then hiding) my own "collection." I did manage to learn my new, thrilling feminine image in the mirror was only a stop gap measure. My true calling was I was actually trying to be the girl. Not just wear the clothes which allowed me to look like one.

Over the many years, I tried to ignore my gender calling by pursuing  a frenetic life. Aided by moving all over, changing jobs and drinking way too much. Needless to say, none of my attempts worked. The more I tried to fight my urges to be a woman, the worse I felt. Even to the point of trying self harm several times.

These days I am selfish. I want all the time and energy returned to me that I wasted chasing a male existence which was foreign to me. 

Would of, should of, could of been listening to my true calling all those years. I was so stubborn, I just couldn't hear or face the truth of my true calling as a transgender woman. 

Wednesday, May 25, 2022


 This morning on a couple of my social media accounts, I noticed two transgender women thinking about reversing all the time and effort they had put into transitioning into the feminine world. To coin an old term, I was in "shock and awe" they would even consider such a move. 

Looking back I began to think of why I moved forward through the dark days of my own MtF gender transition. All the days I was stared at, laughed at and even singled out for pictures. I have written many times concerning the times I returned to the safety of my own home and collapsed on the bed in shame. Somehow, each time I was able to pull myself together and try to improve my feminine presentation.

Transition Picture
Jessie Hart

Through it all, I searched deeply internally for signs I was doing the right thing. The stakes were high. The possibility of losing family, friends and a great job was a huge burden. Surely, many times, the thought of going back to living exclusively as a male was a wonderful proposition. No matter how many times I tried to "purge" myself of my feminine clothes and makeup, in a short period of time I couldn't help replacing my "supply" and starting again. My over-riding thought was I would find the magical clothes and become so good at makeup I would become the beautiful, attractive feminine being I dreamed of being. Of course it never happened the way I dreamed it would be. The best I hoped for was I did become better at choosing better clothes and I did become proficient at applying my makeup. Even though I did receive help on occasion by being courageous and subjecting myself to a makeover at a transvestite mixer I attended. The makeover led to a magical evening on the town.

It was evenings such as the makeover night which led me through quite a few really dark times during my transition to the full time feminine world. Deep down I knew I could accomplish the easy part which was perfecting my appearance as a transgender woman. Later on, I was to discover the harder part was to learn all the layers to exist in the world. Life in the girl's sandbox for me provided several miserable outcomes until I learned how to play the game. 

During this time, as I was doing all my gender "soul searching" one thing kept me going towards my transition during the dark days. When all else failed, the fact remained I just felt more natural in the feminine world as a transgender woman. At the same time I was able to establish a fun, tight knit group of new friends who accepted me as my autunitic self. In a comparatively short period of time I was able to put any thoughts of cross dressing as a man behind me for good.

Unless you are the rare person who has tried a gender transition and found for whatever reason the whole exceedingly difficult process wasn't for you, I can't imagine going back. Life can't be much fun on a gender roller coaster like that.     

Friday, May 20, 2022

A Rare Event

 For me, gender euphoria is a very rare happening. Of course it is the opposite of the gender dysphoria I have lived with most if not all of my life. Just a guess but I think I can trace the beginnings of my gender issues to the days when as a youth, I made exploratory searches into my Mom's clothing and makeup. Somehow someway I realized just clothes didn't make the girl. The urge came from much deeper inside. So I pursued my urges. 

Jessie and Liz

Over the next half century I met with much more gender distress than euphoria. The days of being stared at, laughed at and made fun of felt as if it would never end. Following a steep learning curve of gender knowledge it finally did and I was able to assume a life as a full time transgender woman when I was in my sixties. Which gives you some sort of an idea how slow a gender learner I was. 

The amount of time and effort expended makes it all more worthwhile. Last night was an example.  

Liz and I attended the only transgender - cross dresser monthly social we ever go to anymore. It is fairly close and is held in a venue where we enjoy their food and service. Overall sound levels were low so we could easily hear each other speak. 

Perhaps the best part was the other attendees were respectful and entertaining. I was able to enjoy my time.

By enjoying my time, it was nice to be able to converse with other transgender woman (mostly, except for Liz) and to learn more about their lives. As the evening progressed I felt even more comfortable in my role as a transgender woman. Perhaps this rush of gender euphoria is just coming from being able to get out into the world as my authentic self. Being able to just walk in and out of the venue without being stared at was a gender victory of sorts. It was also vindication of all the years I worked to get to this point was worth it after all. 

Unfortunately, financial considerations tied in with the ever increasing effects of rising inflation are making our public trips less frequent. Actually one per month. 

Perhaps the rare occasions of being able to be out in the public's eye is one reason my gender euphoria is so powerful and wonderful. Also I suppose you can't have one end of the gender spectrum without the other. 

Thursday, May 19, 2022

Is It Time for Pride?

 With all the negative publicity and legislation regarding all transgender women and men, it may be no better time for all the Pride celebrations to take place. Several days ago, I wrote a post on the various Pride events around me and received a couple well thought out comments in return. 

Two of which I thought I would share with you. The first comes from the UK and Paula:

" With the situation we find ourselves in, both here in the UK and on your side of "the Pond" it feels to me that it is time for Pride to go back to being a protest! I am Chair of Croydon Pride, we expect around 10,000 attendees this year, I want them all to now about the attempts to limit the rights of first Trans people, and if "they" get away with that then LGB as well.

Photo courtesy Paula Godwin
Of course putting on an event for that number of people costs money, sometimes our budget frightens me! We couldn't do it without the money from sponsors and the stall holders, but we have to make sure
that those same sponsors have no influence over the program, the speeches, or and campaigning. It's not always easy, and not all Prides manage it. We have fully commercial Prides in Manchester and Brighton, London is a political mess ~ the essence of Pride these days seems to be with the smaller ones like my own Croydon event. I'll admit I do feel uncomfortable with some of our attendees ~ drag, bondage, puppies play etc. but if I'm going to campaign for inclusion then I too need to be inclusive!"

Great point Paula! I also believe it is time to be "out", loud and PROUD!

The second comes from Connie:

"Pride without dignity seems to be the bugaboo that keeps me away from Pride celebrations. Sure, I'm proud of who I am (finally), but I have also learned that being overly prideful about it is not in my best interest - nor would it be in the best interest of the whole lgbtq+ community. I am just not an in-your-face kind of person, and I don't
Photo courtesy Connie Malone

enjoy experiencing things or people all up in my face, either."

Thanks to you Connie. I agree with the "Pride without dignity" phrase. I assume so many have been oppressed with their lives for so long, they go overboard when they have the chance to express themselves. 

"Here in Seattle, we have a separate Trans Pride parade and event a couple of days before the main Pride Parade that takes place on the last Sunday of June. If I were to attend any event, it would be the trans one. I would probably consider, for a minute, wearing a tight dress and high heels if I did, too. ;-)"

Thank you Connie and I am sure many of us wish we could take advantage of having our own separate Transgender Pride event. 

Here in Ohio with the heavily leaning republican presence attempting to pass anti Anti LGBTQ legislation, I feel it is time for the democrats to step up their Pride presence. I am sure too that too many would be against politicalizing the process. The time is now to step up and out if you are out of the closet and can do it. If not, take the opportunity to consider your future and vote the right way to support it.

Sunday, May 15, 2022

Achieving a Transgender Goal

 Similar to other human beings, we transgender folk follow a long path to hopefully discovering our  true selves. 

Even though we face a difficult and often cruel journey to arrive where we are heading, others are not immune from going through similar yet different struggles. It is my belief that even though cis women and men are just born female or male they have the chance to hopefully grow in life to be quality women and men. I see the same struggle with transgender women and men as they grow into their authentic selves. 

Connie and I used to refer to them as "trans nazi's" back in the day. They were the ones who seemingly held the number of gender surgeries you had or didn't have against you. More than likely another version of "I am more Transgender than you" movement. How sad is it any of us have had to go through anything like it. 

Early Cross Dressing Picture
Jessie Hart Collection

My earliest remembrances go back to my first visits to "transvestites' mixers" in Cleveland and Columbus, Ohio. Out of all the different types of cross dressers in the room, the ones who perhaps influenced me the most were the ones I called the "A" Listers. The attendees who were impossibly feminine and attractive. Unfortunately, they were the biggest bitches in the crowd. I didn't want to act like them, I just wanted to look like them. With the help of practice and a timely makeover, I finally earned my right to go out with them and party after the mixer was over. 

Slowly but surely, I was achieving a transgender goal I didn't really know I had. Ironically, I never did fit into a niche group there either. I wasn't one of the "A" listers, nor was I a so called run of the mill  cross dresser. Finally, the term transgender came along to save me. I found my niche. 

Overall though, goals are difficult to achieve for many transgender women and men. We have huge hurdles to overcome when we come out to friends and family. Many times, those same friends and families don't understand they have to transition also. Rarely do we stay the same as we make the journey across the gender frontier. Hormone replacement therapy alone takes awhile to fully set in so transitions are far from complete when a trans person comes out. 

Then there are the gender surgeries. All the way from breast enlargement, to facial feminization, to gender realignment it's often a difficult and painful path to take. It takes a special friend or family member to understand and follow one through such a drastic journey.

Perhaps the most cruel goal of all is the conscious desire to forsake any gender privilege you may have built up over the years living as your non authentic self. Depending upon your age, you had potentially accrued the so called right and knowledge to live a certain way. I was to the point in my life when I had earned the hated "Sir" word. If I was deserving or not. 

I'm fortunate in that I have been able to achieve my transgender goals but I have had plenty of help along the way. I can't forget any of them.   

Saturday, May 14, 2022

Not a Choice

 This morning I was watching the news and came across a story about the average everyday person and choice. What the reporter didn't really ever say was for most things in life, we don't really have a choice. If we like it or not, choices are increasingly being made for us. By now you are probably thinking here comes another rant concerning politicians coming after transgender and even women's rights as a whole. But you are wrong. You all know my positions on the anti LGBT legislation sweeping the country. I would have to be Caitlyn Jenner not to. 

Jessie Hart Collection

What I am referring to is our lack of choice we feel as we transition our gender. Male to female or female to male, it doesn't matter. Normally we go through stages of despair and denial which has led the best of us to "purge" and throw away all the items we have acquired from what would become our authentic selves. My example came from when a close acquaintance of mine decided to purge his "collection" of feminine items. I was gifted a whole box of makeup, wigs and breast forms. Ironically, it wasn't so far before that when I did the same thing. 

During my purges I was sure I still had a choice and could quit the pesky idea I wanted to  be a girl. The feeling was so enlightening, for a week or so. Not being the sharpest tack in the box, I finally learned  my feminine desires were not going to magically disappear simply by throwing away my "collection" of feminine articles. Through it all I was slowly learning my true gender was not a choice and it was not the gender I was trying so hard to live as.

Maybe I shouldn't be so hard on those who don't understand why are living our choice to be our authentic selves. Female or Male. After all they were fortunate to grow up not having to question which gender they were. I will forever remember the lonely mornings when I woke up questioning why I was still a boy following dreaming I was a girl. Resentment  ran deep during those days. Why couldn't I have a choice on the gender I wanted to be?

Of course, gender choices during the 1950's and 60's were even more rare in those days than they are now. In other words, they didn't exist for me. I needed to learn any other method I could to depress my gender dysphoria. I resorted to sports and cars to basically just get by and hide my true gender from family and friends. 

Somehow, I bided my time until I could finally fully transition to a full time transgender woman. During the decades I experienced the highs and lows while living my life in a perpetual gender flux. Through it all, I wish I could impart on all of those considering a gender transition it is not a choice. Although I know the biggest problem can be convincing family and friends why you need to make such a radical move. 

It was never a choice. We just didn't know it.   

Saturday, May 7, 2022

Friday's and the Transgender Woman

Many of you know I have a history degree and consider myself an amateur historian of sorts. Along the way I have developed a deep respect of the historical past being able to predict the future. Somewhat similar to building blocks.

Many of you also know I have written several times about what I consider to be my first night out or history as a transgender woman, rather than as a cross dresser. The difference to me was, it was the first time in my life I was getting the chance to see if I could actually exist in a feminine world. If I was successful I felt I could actually move forward with my dream of living full time. 

In order to try, first I needed a venue to try it in. I had unsuccessfully tried in a number of gay venues and discovered I was only being viewed as yet another drag queen. Far from my goal of being seen at the least as a transgender woman. During the same period of time, a chain of casual bar/restaurants was being invented in NYC and Texas. They were called Friday's and were nearly the first to welcome, attract and serve single women. Before Friday's all bars were essentially were for men only. 

I came up with this information from a television show on food service on the "History Channel". I was instantly attracted from two angles. The second being I built a thirty plus year as a manager in the commercial food business. I ended up working everything from fast food to large casual dining food

operations. The first (and most important) reason was a Fridays in the Dayton, Ohio area was where I first went to see if I could be successful in blending in with and living as a single woman. In this instance, blending in with other women just getting off work from a neighboring up scale mall.

By now, you may recognize how the rest of the experience played out that night. Even though I was scared to death, I did my best to dress in feminine professional attire to blend in with all the other cis-women I knew would be frequenting the venue a little later from when I arrived. To this day I remember the black pants suit, flats and shoulder length blond wig I wore for the evening.

From my experience working in similar concepts, I knew once I made it past the hostess stand and to the bar, I stood a fairly good chance of being served and hopefully accepted. 

To make a long post relatively shorter, I was accepted. I wasn't laughed at by anyone and even though as terrified as I was, I was able to drink two drinks before I made my escape. Most importantly I was still afraid because deep down I knew I had touched a nerve and could possibly live my ultimate dream...a life in a feminine world. I loved it!

Of course Fridays went on to spawn a whole genre of spin offs.  But I will forever be grateful to one of the originals which helped me on my way to a life as my authentic self.

Friday, April 29, 2022

It's Prom Time

 Spring has finally sprung around here and with it comes prom season in the local schools. With prom comes most every young novice cross dresser or transgender girls dream of being the lovely girl in the fancy dress enjoying a night out. Excluding those who write cross dressing fiction, dreams are all the envious boys will experience.

Photo by Amy Kate on Unsplash

Way back in the day, I ended up going to my high school's junior prom one year followed by actually going to two proms (with the same girl) my senior year in high school. It was because we actually went to competing high schools. So all in all, I was able to experience too much prom for my own good. Ironically I had to spend my own hard earned money on something I was so envious of. Instead of me being restricted to a tuxedo, I had to present a corsage and purchase dinner for my finely dressed prom dates. 

The only positive I could see coming out of the whole evenings was for the first time I was actually going out with girls. Leading up to that point, I was so shy and confused about my own gender, I still could barely talk to girls at all. I continued to place them all high up on an impossibly high pedestal. The pedestal included being jealous on my end of a date in a pretty formal with professional makeup and hair. So badly I wanted to be her. 

The closest I ever came was years later when the supper club we went to eventually closed and changed into a gay venue. It took awhile but at least finally I made it into the same rest room/powder room my date went to. A small victory to be sure but at the least a small amount of satisfaction of the fact finally I was making strides in the right gender direction.

Today, from the outside looking in, times seem to be better for an increasingly larger number of young transgender girls. Every now and then I read about a trans girl being elected to her schools' homecoming court etc. Plus there doesn't seem to be the social pressure for actual prom dating. I remember how my first date was set up through in betweens.  In other words friends of the girl who turned out to be my first date set her up with me because they knew I didn't have a date .Being so far removed from the school scene these days I can't even speculate on current proms.

I do know an increasingly number of LGBTQ organizations around here are organizing "adult proms" for those who for whatever reasons never had a chance to go to a prom. Plus I know of a couple of places locally who deal in used discount prom dresses for those who need them. 

The closest I have come to needing anything remotely formal to wear was several years ago when my partner Liz and I attended a holiday performance of the Cincinnati Symphony Orchestra I think I was as scared going to the performance as I was so long ago on the first prom. For the evening I managed to pair a long flowing pair of black pants I owned for awhile with a black sparkly sweater top I located in a thrift store, belted at the waist. A beaded small black purse completed my outfit.    

Hopefully, during this prom season you can do something such as attending an  adult prom to see what if anything you missed.