Reaching Out for Truth

 

Image from Jen Theodore
on UnSplash.

As I transitioned into my form of transgender womanhood, first I needed to find my own truth. In order to do it, I was placed in a dilemma. 

The dilemma was I needed to make sure my gender journey was taking me in the right direction. I needed to make a huge life changing decision so I needed time and experience to make certain I was taking my life in the right direction since essentially I was risking everything to do it. In other words I needed confidence. 

Gaining confidence proved to be a fragile thing to find. I would have it following a successful day out away from the mirror as a novice transgender woman when I seemed to do everything right. My makeup, wardrobe and wig were on point and I even carried myself fairly well. I was building the life I always had dreamed of and seemed to be within reach until the next time I went out and everything crashed and burned. Either I did something very unrealistic and was laughed at or my overall appearance just wasn't right. Whatever the problem was, my fragile confidence was shattered. And, as we all know, confidence is our most powerful accessory. Humans are similar to sharks, if they perceive something is wrong with you, chances are the other human could act on it. A big turning point for me was when I arrived at the point where I did not care what anyone else thought of me. 

Actually, let me re-phrase that. I did not care what men thought of me because for the most part they had all felt as if I was from another planet anyway and wanted nothing to do with me. On the other hand, I did care what other women thought about me. Since I needed other women's acceptance to exist in the same world they were in, I needed their approval. In order to survive, I needed to be honest to myself which in turn, made me honest to them. I was not hiding anything. I was upfront on what I was trying to achieve which was to give up my old life as a man. Very quickly I learned I appealed to more women as a friend than I ever had as a man. I thoroughly enjoyed my learning curve as a transgender woman and wanted to build on my truth even more.

Even still, on occasion, I was still having issues with living my truth. My biggest hurdle to conquer was myself. I was the last to know my truth because I hid it all so well. To my everlasting shame, I even lied excessively to my second wife about what I was really doing while she was working at night. So, by osmosis, I was lying to the two closest people to me. Something I am certainly not proud of. However, I am proud of the fact I did reach out and grasped my truth during my long life. 

It took me long enough to do it. I struggled for over fifty years as a cross dresser and went through so many stages of attempting to figure out who I really was. I was so much more than a man who liked to wear women's clothes, I wanted to be a transwoman wearing women's clothes. Once I learned this major truth about my life, finally everything came into focus. 

Into One Club and Out of Another

 

In the Women's Club. I am on the bottom row
to the left.

As I transitioned into transgender womanhood, I learned how quickly I could be pushed out of one gender club and make my way into another.

The first club I was quickly rejected from was the good old boys club which I was tired of anyhow. I quickly found many of the gender stereotypes were true. My primary example was and is when I am in a conversation with a man, I seemingly have lost a good portion of my intelligence. In many ways, I was expecting it because of the way I had seen many men around me in my life treat women. I wanted a change in the worst way.

Of course leaving one club and being accepted into another was not going to be the easiest thing I had ever done. As I set my course into the world of women, initially I was met with little resistance except for two key people in my life. Along with my second wife who hated the idea, of course my male self was dead against it also. He was the one who was getting kicked out of the club.

One of the first aspects of being accepted into the woman's club I learned was to look for the hidden knife behind the back trick. All of a sudden I was in the world of passive resistance. Some women did not like the way I looked or acted all the way to resented my presence in the club all together. Rather than tell me to my face, they worked behind my back to drive me away. I came away from the learning experience with many claw marks on my back. I considered it all as a initiation experience into a new exciting world where all I wanted to do was play in the girl's sandbox. What I never counted on was how complex the new world would be. I knew women were much more complex than men but slipping behind the gender curtain and living my dream proved it.

I fought hard to keep my dream from becoming a nightmare. First there was the problem with learning how to dress myself so I could stand a chance of blending in with the other women in the world. Then there was the problem with learning how to go with the flow, or practice moving like a woman and last but not least, there was the problem of learning to communicate with the world in my new club. The more I progressed with all of this, the more I did not want to be forced back into the male club because the pressure was constantly there. Going back meant leaving all the gender struggle behind me and regaining all the male privileges I had lost when I entered transgender womanhood. 

Somehow, I always managed to keep my dream alive and no matter how beneficial going back seemed to me at the time, maintaining my hard earned membership in my new club was more important to me. I had served my time in an unwanted male existence and had no desire to return. So I continued to spend time in my new club as a transgender woman and learn the benefits of living an authentic life. 

I never really missed the benefits of living in the male world.  Then I needed to set out on the complicated process of telling all of those who thought I was still in the male club, I was not and please listen to the reason why. Some people and family I was successful with and some I was not but none of it kept me from trying. My main goal now is to keep my membership in good standing in the transgender woman's club.

What I Really Learned at Halloween

Kenny Eliason image from UnSplash.

 Sadly, since I have lived over ten years as a full-time transgender woman, Halloween has become just another day to pass out candy to any kids who may come by the house. The neighborhood is becoming older and we don't have the influx of kids we used to have years ago.

Regardless, I still have fond memories of when I went all out for Halloween. I used the experience as a testing ground to see if I could actually go out into the world as a woman and live. Throughout the month, I have focused on several Halloween adventures I had. When I first started, I thought dressing sexy would validate myself as a woman. Then I started to tone down my "costumes" all the way to going to the last party I remember dressed in feminine business casual attire which I was used to presenting in the upscale malls I was going to. 

The party itself was sort of a who's who of invitees held at a real live Victorian mansion in a restoration district in the town I lived in. I received my invitation because I was a fairly well known radio disc jockey in town at the time and happened to know the couple putting on the party. I knew immediately what I wanted to wear and just needed to decide who I wanted to invite to come with me. I knew my first wife was not into Halloween and wouldn't care if I invited someone else to go with me, so I invited the news-woman where I worked to go instead. An example of how easy going my wife really was. I always thought if I told her I was leaving for a month for gender realignment surgery, it would be fine with her. So the stage was set to be out and about as my authentic self. No playing around with a "costume", I wanted to be mistaken for the real deal.

Since there are no pictures from the party, my outfit consisted of a business suit, heels and blond shoulder length wig. Needless to say, my wife was not surprised but my date was completely. Mainly because of my shaved legs and how well I walked in the heels. When we arrived, thankfully, parking spots were not a problem and at the door, a coffin with a real skeleton greeted us . The mansion was really decorated well and we found a seat. 

Predictably, as the night went by, no one knew who I was and I blended in as a woman who arrived late from work and did not have a chance to find a costume. I was having a great time, when another couple came up and said how impressed they were with the way I looked and they thought I was a woman. Furthermore they were leaving soon to go to another party and wanted to know if we or I wanted to go along. Even though I was extremely flattered I turned them down but not before I found out who they were. The couple was a young congressman and his wife, leaving very soon to go back to Washington, DC. So I guess I destroyed any chance I had at a political career. 

What I really learned that Halloween was I could step out into the world as my authentic feminine self and survive. Very much worth all the time and effort I had put into to being a girl over the years. And, as far as the news-woman went, she never said a word.  

I guess you can say with out a doubt although the thrill is gone for my Halloween, the day more than any other one in my life served a wonderful need when I did not have any other outlet.

Set Her Free

Image from JJ Hart

Throughout my long life, which included fifty years of being a cross dresser, I could feel the stress and tension of not freeing my inner girl.

It all started innocently enough with trips in front of our family mirror in clothes I had borrowed from my Mom. Of course that all ended when I outgrew her sizes and I needed to strike out on my own to find fashion which fit. With my meager allowance and money I made from delivering newspapers to the neighborhood, I managed to get by and buy a few items to add to my wardrobe which then I needed to carefully hide away from my family.  Somehow I survived and my life as a male set in, no matter how much I did not want it to. 

The gender stress and tension continued over the years and even became worse with every success I had when I tried to set my inner self free. It finally became evident my entire gender life was backwards, I was not a man cross dressing as a woman, I was a woman cross dressing as a man and it was no wonder I was feeling the confusion and pain. I would not have wished the mental anguish I felt on my worst enemy. I found being transgender was far from being a choice and somehow I needed to set her free.

The problem was, I needed to face the same set of hurdles transgender women and trans men face. Such as family or spouses, friends and occupations. The longer you go in life, the more gender baggage you acquire, the more you have to get rid of. Or figure out how much you can keep. My prime example always is how I was able to maintain my love of sports when I fully transitioned into transgender womanhood. I had help when I learned the women around me loved sports as much as I did and I felt right at home. It was easier to set my woman free. 

Finally, I arrived at the point where I could take it no longer. I ended up living more time as a trans woman than I did as my old male self. So much so, I was feeling totally out of place in a male world as a guy and would have rather attacked it as a woman. Plus I still had the age old problems of doing my best appearance wise as a feminine person. I began by losing nearly fifty pounds and taking better care of my skin on a daily basis and worked my way forward from there. Through days of trial and error, I was able to arrive at a point where I could provide a reasonable attempt at presenting as myself on a regular basis. The key was to settle in to what myself should look like which meant stopping doing things such as switching wigs on a regular basis. Finding who I was proved to be the key to setting myself free.

Once I did manage to set my dominant self free, she did all the rest. I learned to keep my old male self out of the way and let her go. Among other things, she picked my friends and lover and opened the door to a life I never thought possible.

It was like she was saying I told you so and should have done it sooner. 

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.  

Connections through Isolation?

 

My wife Liz on left
from the JJ Hart Archives

When I finally began to be successful in my femininized public pursuits away from the mirror, I was content to be alone in the world.

By being alone, I didn't have to face any communication problems with anyone else I faced. Essentially, I just passed through their world quickly and was gone. I did not want to know them better and have to challenge myself into interactions with strangers. Ironically, my idea did not last long as I was increasingly thrust into public interactions as a transgender woman I did not want. In the beginning, I just was not ready to look another person in the eye and risk ridicule.

I learned quickly, my public interactions would be overwhelmingly with other women. Initially, I interacted with clerks in clothing stores who were mainly interested in helping me with my money, except for the few who wanted to help me with my fashion. It did not take me long to realize what was going on and then move on. 

I began to stop and eat lunch to extend my shopping trips which meant ordering from a menu with a server and/or bartender. I found sitting at the bar made for a more personal experience unless the staff was very busy with other patrons and I could try out speaking with others as a trans woman. Very soon out of forced habit, I found myself relaxing more and even enjoying the experience. It was like I was completing a long lost part of my new personality as I left the mirror and entered the world. It was a challenge and I grew to love it. I discovered also many more women than men wanted to know more about me. Women were curious while men were scared of me it seemed and I loved it. 

Along the way, when I first began to communicate I tried to mimic the voices I was hearing from other women and try to repeat doing it until I thought I was doing it right. I even took voice lessons for awhile to improve my vocal presentation for my transgender womanhood.

Still, after my second wife passed away, I was extremely lonely. Not only was I facing finding another person I loved at the age of sixty, I also had the added pressure of doing it as my new version of my authentic feminine self. I was prepared to spend the rest of my life by myself. Little did I know I would not have to. Initially, when I went out to supposedly socialize and find new friends, I was going out to be by myself. If my gender was never challenged I would have taken the easy way out and would simply go back home to my two dogs. 

If it wasn't for a bartender at one of the venues I had become a regular in, I would have remained in the social rut I was in. One night not long after I arrived, she served me my first drink and quickly asked me if I would be interested in meeting her single lesbian mother. Of course I said yes, and a friendship  started that has continued over ten years till today. She is the woman who took me to the NFL Monday Night Football game. A very scary experience which cemented my arrival as a full-fledged transgender woman in the world. But that wasn't all that happened at my favorite venue. Another night, as I sat alone to be by myself, another woman came in to pick up her to-go order. While she was waiting, she slipped a note down the bar to me asking if I was interested in having a drink sometime. I said yes and the three of us ended up having a great time the next couple of years as we watched sports, drank too much and had fun at lesbian mixers. My two new friends ushered me into a world I never thought I could go.

Against all predictions, my connections through isolation worked very well for me. My new friends which included my wife Liz who also identifies as a lesbian, all helped me into my own important version of transgender womanhood. Destiny was certainly helping me during this period of my life.  

Seraching for Me

Image from Selcuk S
On UnSplash.

Ironically, during my life I have spent too much time searching for who the true me was.

Naturally, I am referring to finding the springboard I needed to determine which gender I was. When I was younger, I made the habit of waking up in the morning wondering if I was a boy or a girl. I was very gender fluid for years before I decided which gender direction was the correct one for me. The problem was I needed to put on my gender blinders and attack the world daily as a male. Something I never wanted to do.

It turned out the springboard I needed to find out the me I was looking for was still a long way in coming. I still needed to cross or follow many paths before I found me. More precisely, I had parenthood come into my life as well as many challenges such as military service, marriages and just life in many ways. I was constantly searching for my gender by going out and exploring the world to find out if I could ever achieve my dream of transgender womanhood. The journey was so difficult when I experienced negative feedback From stares and giggles, all the way to people singling me out for pictures, I did it all before I made a better effort to blend in with the rest of the world.

All in all, I found just being me was going to be much more complicated than I ever thought possible. It all started for me in the days when I always thought the grass was always going to be greener for me on the feminine side of the border. I discovered, even though my trip across the border was terrifying at times, on the other hand I felt so good and natural, I knew there could and would be no turning back. No matter how easy it would have been. At times, I was even a bit jealous of men who had never experienced any gender issues and were able to live out their lives enjoying male privileges. It all just was not in the cards for me during my life.

Just me, turned out to be so much more. I am a parent, a grandparent and a spouse to a supporting wife. In other words, I am so fortunate to be surrounded by people who care for me. Plus during my life I have been able to take an in-depth dive into how both main binary genders operate. What really breaks my heart is when one of the bigoted transphobic political commercials comes on with all it's lies. I want to tell the haters that even though I am a transgender woman, I have a life not so different from theirs. I am just busy being me.

Perhaps the problem is, since my life turned out to be more complex than the so-called norm, so people don't want to understand or care. 

By this time in my life, I have learned being just me will have to be good enough. I have worked too long and hard to give it up now. From having a gender fluid lonely youth to finding my true self in trans womanhood, I think I have been fortunate to end up where I am. Plus, I will continue to advocate for all transgender women or trans men such as my transgender grandchild with their whole life ahead. There is so much to do. Maybe I can just be a positive example to another novice transgender person still living firmly in their closet. Who knows? Maybe you can be next to escape and live as your authentic self.

Passing the Big Tests

 

Image from Shifaaz Shamoon
on UnSplash.

Throughout the years, I found out I had time after time when I needed to "pass" or present well as a feminine person in key situations.

Probably, there are too many to remember but here are a few I recall besides the major one I always write about. It was when I went out to see if I could exist in a world of single professional women in a bar/restaurant I went to as a guy. I really wanted to see if I could make it from the other gender side I had always dreamed of. I wanted to be the other women so badly and now I found I could actually do it. Of course from that point forward, my life changed and I could move forward on a different gender path. 

Forward had it's own set of challenges. One aspect I was really successful at was accomplishing two things at once such as going to the grocery store. By doing so, I was accomplishing a task which most women do again as my feminine self. From there I was able to expand my horizons to other venues such as antique malls where I could admire myself in the old mirrors and at the same time shop for a gift for my second wife. The effort was especially valuable around the Christmas season. 

All along, my experiences were adding to my overall confidence in my new exciting life. Even though, I did not really approve of or buy into the concept of passing, I did approve of blending into the world as part of my transgender womanhood. I was cherishing the time I spent in my new life and increasingly hating any of the time I needed to go back to my old male ways. I was fascinated with how quickly I was adjusting to my new feminine ways. The entire process proved to me I should have been living this way all this time.

Still, I had big tests to pass. It seemed I was going back to school and everytime I passed one test, there was another to go. Another one I just went through was having a mammogram. As I wrote yesterday, mammogram day was upon me again and the nurse could not have been nicer. She asked me about my family history with breast cancer and we went on from there without any invasive questions. She was much better than the nurse last year who acted as if I was some sort of bother.

To arrive at the point I am today, I needed to pass the communication test. There was a time when I would be shy and reluctant to look another woman in the eye when I was talking to her. With quite a bit of practice and trial and error, I found myself enjoying the interaction with other women. I have passed the gender test.

Of course life will always present other challenges around blind corners. I just hope I am up to the challenge, especially when someday I know I will have to face off with a transphobic person. In the mean time, I will do the best I can to pass the big tests when I can. It all continues to be so different than back in the male days when I could simply try to out bluster the other guy. Over the years, I have had so many knives I have pulled out of my back from other women, I think I am ready for more claw marks.

It's Mammogram Day

 

JJ Hart, image from Columbus, Ohio.

Once a year, my doctor puts in a request for a mammogram screening for me. Mainly because breast cancer runs in the family. My maternal grandmother died of it back in the 1950's when I was quite young. 

If you have never experienced a mammogram, there is some minor discomfort involved but nothing major. In fact, I consider the whole procedure to be a rite of passage of sorts for me into my own transgender womanhood .Even though I have a difficult remembering for sure, I think this is at least my sixth or seventh mammogram. So by now, I have a very good idea of what I am facing. 

For the most part, I have been met with an inclusive caring staff and have had only only one experience with an unpleasant nurse who asked me vague questions about if I had any work done down below. Like it was any of her business one way or another. She was border line evil and happily I have never seen her again. Anymore questions like that and I would have had to report her.

I am going to a new, closer hospital today for the test and I will be interested to see how it goes. Plus it could be my last breast test because of my age. My Doctor said no one gets them anymore past the age of seventy five. So I guess when you get old, you are on your own. Regardless, I am hoping for a clear mammogram today since my blood work did not come back so good. I have an appointment with hematology coming up in mid November. Even though I want to worry about it, I am trying my best not to build any un-necessary bridges to jump off of before I need to. 

I know this is a short post but I need to get ready to go here fairly soon. It's a fairly rapid procedure, so I should have most of the results back today.  

Turning Your Gender Corner

 

Image from the JJ Hart Archives.

As I made my way towards coming out of my closet and living as a transgender woman, I found I had many corners to navigate.

At first the corners were easy to take on but then became progressively more difficult as I moved closer to my impossible dream of escaping my male life. Through out the fifty years I lived as a serious cross dresser, it seemed I spent too much time researching to see if a life as my authentic femininized self was even possible. What was I going to do about a disapproving group of family, friends and bosses. All corners I needed to see around and judge what was next. 

At times, a few of the corners were more frustrating than others. My primary example always is when I spent years thinking my appearance as a woman (trans or not) was the all important driving factor in how I lived. There was so much more to being a woman than just how I looked. Appearance did open or close many doors but it was only the start. Also, as the internet began to have an impact in my life, I started to research more and more about what the new transgender term was all about and how did it define me. Initially, I thought it did because when I went to transgender - cross dresser mixers I did not mix well with the transvestites and leaned towards the transsexuals in the groups. I was somewhere in between and it was evident to me I had many more corners to turn before I discovered where I wanted to be.

Looking back, during that time in my life, I was gender fluid but had no way to express it. 

As I did begin to aggressively pursue my gender path, I needed to put all the labels behind me and try to determine if my dreams were indeed reachable. Right or wrong, I began to slip out of the house when my wife was at work to live an entire whole new existence as a woman. To do so, there were many blind corners I needed to face, Perhaps the biggest one was when other women wanted to strike up a conversation with me. I found they would start innocently enough with a small compliment on a facet of my wardrobe such as ear-rings and move on from there. Fortunately, most of the conversations were innocent enough as most of the women just were curious about what I was doing in their world. After the first shock of having to communicate in a brand new world, I actually turned the corner and began to appreciate the attention I was getting. I never had that amount of attention from women in my male life. The roles were reversed because I was receiving little to no attention from any of the men I met.  

Even though sometimes we follow similar paths as transgender women and trans men, the gender curves and corners are vastly different. We all have spouses or girlfriends who provide various levels of support or push-back. Often the push-back leads to mental health stress all the way to suicide attempts. 

Through therapy, often turning the gender corners you face may be easier. I know in my case, a mixture of going out on my own to start a new life along with therapy to do away with the old one worked for me. 

Now, at my age of seventy-five, I have come to realize the gender corners I will have to face will always be there as I face the possibility of advanced elderly assisted living. It all seems just a part of the problems we face as transgender women and trans men. 

Halloween and Gender Breakthroughs

Halloween
Image from
the JJ Hart
Archives. 

Back again we go to Halloween and the effects it had on me as I developed into a novice transgender woman.

Very early on I learned when I cross dressed head to toe as a woman for a Halloween party, I would be cut out of the male club and my male friends would ignore me. Very early signs of losing any male privilege I had built up over the years. On the other hand, I was not ignored by many of the other women I knew from before who took the time to comment on my shaved legs and "costume." Both were small but definite signs of what I would face in the future if and when I decided to enter the public as a transgender woman. 

Over the years, my tastes in Halloween "costumes" changed from just wanting to be slutty, all the way to trying to present myself as a cis-woman would at a party. Plus I needed to overcome any fears I had of going to the party as a woman and mostly giving up on having a traditional good time partying with friends I had known for years. Again, just a small dose of what it would be like to cut all ties with my old male life and start all over. 

Everything began to change when my "costumes" began to evolve. One party in particular stands out in my mind. It happened when my second wife and I were living in the metro New York City area and I was managing a food location. It just so happened I was invited by one of my assistant female managers to go with her and several of her friends to a Halloween party they were going to. Without hesitation I said yes and wondered how I was going to explain it away to my wife. She never was into Halloween much and turned out she did not much care so I set out to put together an outfit for the evening. I decided to go semi-sexy (or try to) and chose my short mini dress, heels and dark wig for the evening. Off I went into the great unknown of not knowing where I was going and with whom.

It turned out, where I ended up first of all was at the house of my manager and to my pleasant surprise I learned all of her friends who were going were all tall attractive women dressed approximately the same as I was. As I walked into the room where they all were waiting, you could have heard a pin drop as they all looked me over from head to toe. Once they realized who I was, off we went to the real party which was being held at a small bar near to her house. The first thing I thought of was how far was I going to have to walk in my heels but the distance was not too bad and I was on my own cloud nine. I mean, here I was with three other women my height dressed the same way headed for a party. I was scared but excited by the time we arrived at the venue. Once I got to the bar and had a drink or two I started to calm down and learned another couple of gender break throughs. 

The evening turned out to be my first ever girl's night out because I was able to blend in so well with the other women I was with and I learned the power of being able to blend in with the feminine world. The second big breakthrough I learned was how to handle being approached by a man who perhaps did not know he was talking to a transgender woman. I was even asked to dance by one man. Finally, I learned single women of a certain age have a tendency to mark out their own territory when it comes to attracting male companionship. Once we all arrived in the venue, I was left very much on my own. 

I did not know it then, but all of the gender lessons I learned would come back to help me later in life. So much more than an empty comment about how good my shaved legs looked. As my second wife kept trying to tell me, I hadn't paid my dues yet to be considered a good feminine person. Trans or not.   

It is Fall and Time for Halloween

 

I have heard Halloween is the national holiday for cross dressers everywhere.

I know it was for me as I could not wait for the trees to change colors and the temperatures to dip so I could plan my "costume" for the season. I was fortunate when I began to learn so many feminine basics thanks to my Halloween experiences. Such as, the first night I went out with friends to a late night showing of a silent movie in a beautiful restored theater in Columbus, Ohio. The primary lesson I learned was to either get a close parking spot or wear comfortable footwear as my heels began to bother me very shortly into the evening. Regardless, I had a great time in my short mini dress and I was disappointed when I did not see anyone else cross dressed (that I know of) and the night went by so quickly. My friends we went with did not even mention my shaved legs. I remember thinking it was going to be a very long year before I again could challenge the world as my feminine self.

Back then, my self was very under developed. The mirror still had a hold of me and I really had very little knowledge of where I truly wanted to go as I researched the gender world. Would the mirror be my home or could I succeed as a novice transgender woman. In it's own very important way, Halloween helped to point me in the right direction. The first parties I went to, I simply tried to dress sexy as my "costume" and took the easy way out. I was seeking validation as a woman  essentially by doing a form of drag, which never worked for me. For the most part, I was left alone by other men and women. It took me several parties to understand what I was doing wrong. 

From there on out, I started to attempt to tone down my "costume." For example, one year early on in my transition I wore all black. Starting with black flats, black tights and sweater. I paired it all with my short black skirt, long blond wig and topped it off with a black beret hat. I tried it all out at one of the big dance clubs Halloween party in town and was enjoying myself immensely until a person in a mask came up to me and said I know who you are. Initially I was a mixture of being scared and devastated some one could see through my "costume" so easily I did manage to laugh and say who was I and the person said I looked just like my Mom. Then I realized who he was and he went on his way. It turned out I grew up near him in the rural neighborhood where I lived. Even with all of that I had a great time and was saddened that Halloween only came around once a year.

It turned out there were many other lessons to learn from the cross dressers national holiday as I was going to find out. One of the biggest ones was when I realized how rare it was to find another possible "non civilian cross dresser" in their own "costume." Again, I was feeling alone in the world. Another one was there was no way I could wait another year to venture out into the world as my authentic femininized self. At the same time of my Halloween adventures, the internet became a part of my life and I was able to research terms such as transgender to see if they fit me. I found there was so much more to learn. 

There were more Halloween parties where I continued to learn from too. I haven't forgotten my pledge to share them also since for the most part, they had such a profound effect on my life as a novice transgender woman. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.   

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Intimidating Women

Library of Congress 
image from 
UnSplash.

During my life, surprisingly so, I have encountered many intimating cis-women. 

Probably the most intimidating of all was my Mom, a dynamo at a mere five foot two inches tall.  From early as I can remember, we clashed on many different issues probably because we were so much alike. On the girl side, I was fascinated from a young age when I watched her skill with makeup and hair. I could only dream of ever duplicating her prowess. Of course I would never get the chance for her to ever see the fashion skills I finally developed as the daughter she thought she never had. 

As I grew up, my intimidation of girls of all kinds increased. I was so jealous of their ability to dress in pretty clothes and wear makeup continued. In addition, I was so shy, I was afraid to communicate with girls at all. So my problems continued to get worse. I never had the chance to circle back to where I began. All the time I was cross dressing in front of the mirror, it was a very solitary, lonely experience as I craved the peer feedback other girls my age had to work with. 

The older I became, the more I admired women who were stronger and spoke their minds. You might say I was intimidated in the most positive ways by strong women. I was even attracted to them to the point I chose one for my second wife who I was married to for twenty five years. Even though she knew I was a cross dresser from the very beginning, somehow I secretly thought she would help me with my on-going quest to be a feminine person. She never really did help me much and very much resisted any ideas I had I was a transgender woman. 

Perhaps I am attracted to strong successful women because I wish I was one. I so admired the women managers I worked with because of all the extra skills they had to use to be successful. Most if not all of them had families to support at the same time they worked a full-time job. I was in the restaurant business and some of my best kitchen managers were women who dealt with macho kitchen crews. 

Being a transgender woman, I think sometimes I intimidate other women. Sometimes they seem to melt with kindness such as the hostess last week when my wife Liz and I went out for my birthday dinner. She was beside herself to make sure we were satisfied with our experience. As I can remember, intimidation on my part of a guy was when I was shopping at a grocery store years ago for the families groceries. In those days, a fashionable woman who had the legs wore an oversize sweater with flats and a mini -skirt, so I did on that day. As I chose our food, I tried to contain my fear in checking out, I found I was wrong.  As it turned out, the store was nearly empty and only had one check-out lane open with a woman cashier and a male bagger. 

It turned out, I really intimidated the bagger, he blushed and stuttered when he asked me if I needed help taking my bags to my car. I looked at the cashier and him when I said I didn't and she gave me a slight knowing smile. I wondered then, if she knew I was transgender at the time or not. Regardless, it was quite the experience. 

It wasn't until I transitioned into a feminine world as a trans woman did I fully understand all the nuances of what it takes to be an intimidating woman. For example, some women use their heels to begin the process. Heels give a shorter woman a height advantage to be able to compete with the men in their world. Plus, these days, more and more young women are becoming educated to give themselves an extra advantage in the world. 

It turns out, in my life, intimidating women are becoming the norm as the future is female. 

 

Becoming Me

Image from the 
JJ Hart
Archives. 

As I bridged the gender gaps in my life to survive, I did what I perceived to be cross dressing as a woman in my family's mirror. 

Slowly I began to learn the makeup and fashion tricks the girls around me used to look their best. At times it seemed I was attempting the impossible as puberty set in and my body began to go through many unwanted male changes. Like it or not, I was stuck with testosterone poisoning and I would somehow have to get use to living with it. I was becoming a me which was very much unwanted. 

As I got by in life, I learned to camouflage my broad shoulders, and torso (among other negatives) and try to emphasize my positives, even if I needed to do it with feminine style padding in all the right areas. Since I was told I had good legs at the Halloween parties I went to, naturally I tried to emphasize my legs when I dressed. 

Sadly it took me many years to learn the truth about myself. Yes, it was true I was a cross dresser but not the way I always thought I was. In no way was I a male cross dressing as a female, all along I was a woman cross dressing as a man. Once I arrived at that point in my life, suddenly everything began to be so much clearer. I just wish I could have come to the realization so much earlier than I did. I always use the excuse to myself the world itself held me back in the pre-internet years before very little was being published or researched about gender issues. In fact, I still remember in my youth the news stories about the police rounding up and arresting men dressed as women. How could that be? 

Still I persisted and remember vividly the night I dressed up in a mini skirt, panty hose, heels wig and makeup and headed to a nearby gay bar when my wife was away. I was so scared and once I got there and was admitted through a locked door, I only had one drink and left before I even relaxed and I never had the opportunity to go back before the owner died and it closed. Even still, my adventure that night helped me to become the transgender person I wanted to be. At that point, the problem still was, I did not totally know who I was, or face up to her yet. But I was diligently working on the problem by researching my feminine life. 

To do the research, I needed to risk everything and leave the safe surroundings of the mirror and enter the world. I started with going to more gay venues and becoming quickly disillusioned when they all thought of me as a drag queen. Lesbian bars were better but I did not find true acceptance until I became brave enough to go to straight places. There I could watch my sports, drink my beer and become accepted as a regular fairly quickly by the staff. I minded my own business, tried to be friendly and tipped well and was in. Even though I knew they knew I was transgender. it did not matter and along the way I think it even helped me. One way or another, I was taking giant steps towards being me and I knew there was no way I could ever go back.

Perhaps the biggest step I ever took on the gender path to being me was when I started on gender affirming hormones. After being approved by a doctor, the changes occurred quickly.. In addition to the external changes such as breasts, hair and skin, I experienced internal changes also. My emotions changed as well as my whole life just softened. The entire time of gender adjustment was one of the most magical times of my life. 

Overall, the discovery of who I really was as a transgender woman was a terrifying yet exciting journey. One I don't regret taking, once I faced up to her, I was so much happier.   

Connecting the Gender Dots

 

JJ Hart, from
the archives.

Many outside of the LGBTQ community, or more precisely the transgender community, think connecting the dots between male and female is as simple as putting on a dress and makeup.

One of the problems is, in order to  walk a mile in our transgender shoes, you have to learn to tie the laces first. Very few people have the patience or understanding to do it. The complexity of gender scares most people off. They think gender is cut and dried but is the opposite. 

Even those in the community have a difficult time connecting the dots and don't realize that even if we have similarities as trans women or trans men, we have just as many differences. Obstacles such as male lives, spouses and sexuality face us as the next dot to connect becomes bigger and bigger or worse yet out of reach.

During my male to female transition, many times, connecting the dots seemed downright impossible and I would never be able to move ahead in my life. My primary problem was my spouse and my male  self were standing directly in my path to gender realization and they would not move or give up their spot in my life. What I did in the meantime, was fall back into a more realistic journey to the next gender dot. An example would be when I began to get out of the non challenging mall shopping experiences and into actual interaction with the public as a transgender woman. 

Many times, the dots would totally fool me when I totally had a mis-conception of what a woman's life would be like. For some reason, I did not think I would be the one whose personal security would be challenged or my intelligence would be diminished when I jumped the gender border into trans womanhood. I was wrong in my judgement and needed to rapidly rethink my path to another dot. Of course I always knew women's lives were much more complex than men's but I did not really know until I succeeded in connecting my dots. 

The frustrating part of my whole experience was two-fold. The first part was I needed to accomplish it on my own with no help and the second part was everytime I thought I had accomplished something, immediately it seemed I needed to accomplish another milestone or dot on my gender journey. It was not until I was accepted in a small tight knit group of women friends did I really begin to make progress in the world. I learned through them, I could validate myself in the world as a trans woman without the help of much of the public, including men. Connecting these dots made my life fun again and so liberating. 

I can not begin to completely describe my experience connecting my own dots because they could be so much different than yours. The one thing we may have in common is, in order to have success in the world, you have to summon the courage to put yourself out there. Of course the problem these days is the concern for your personal safety. You have to be very careful, be aware of your surroundings as any other woman would and connect your dots the right way.       

 

Building a Dream

Image from Moreno Matkovic
on UnSplash

 Similar to many of you ,my journey to building a dream took me many years.

As I am fond of saying, over a half a century of construction. A long time when you think about it. At first the steps were obscure and very shadowy as I snuck behind my family's attention to cross dress in front of the mirror. I did not know much about what I was doing, or the tools to do it so I looked as if I was clownish, most of the time. As luck would have it, the mirror often lied to me and gender euphoria set in, before I even knew what it was and what it meant. All I really knew was how at night when I slept, I dreamed of being a girl and was sad when I woke up and needed to face the same old male world.   When I was able to escape into my feminine world, I felt so natural and exhilarated, I just couldn't stand to go back.

The years flew by and I was able to learn more and more about the femininization process I was facing. At the same time, small glimpses of what if slipped into my mind. Or, what if, someday I could make living as a woman trans or not part of my reality. As I did, the reality of building a transgender dream became increasingly difficult. Partially because, at the same time, my male life was becoming increasingly successful and it became  harder and harder to give up what I had built. Still I moved ahead as the feminine forces within me were so powerful.

Since it is coming close to the Halloween season around here, I would be remiss if I did not mention how going to Halloween parties dressed as a woman did not help me build my dream of perhaps being a full time woman some day. Back in those days, the term transgender was still in it's infancy and I did not know how it fit me. All I knew was, I worried and stressed for months ahead of Halloween about what my "costume" would be. Predictably my outfits started out slutty and evolved into going to parties dressed as business professional to see how many people would notice I was a guy at all. Overall, I had several meaningful experiences at Halloween which provided quality building blocks I could use when I seriously began to enter the world as my authentic self. As promised, I will write more about them as Halloween comes closer.

In the meantime, I was having more and more opportunities to learn I was so much more than a man who wanted to look like a woman. I even received a  comment from "Paula" across the pond in the UK concerning a blog post I wrote on the subject:

"I often think that the moment of realization that you are a trans woman rather than a cross dressing man is the Biggy! After I accepted who I am everything else that followed was just a natural consequence of that initial revelation. After I had accepted that I was in fact a woman it was perfectly logical that I would want the world to experience me as such, so I went full time. As I wanted to experience the fullness (as much as possible) of life as a woman it was perfectly natural to get medical help, leading first to hormones and then surgery. All of those decisions were the natural consequences of that first understanding that this is who I am not something I do."

Thanks to Paula and all of who comment! I could not have put it better. 

As it was, I kept on building until I formed a solid foundation to finally achieve my dream. It was never easy but on the other hand, building something worthwhile never is.  All the lonely nights I spent going out just to be alone come to mind as well as the occasions I was shunned or even laughed at. At that point my dream seemed to be so far away. Deep down I knew I was doing the right thing and kept on building. It turned out happiness was just a build away. 

When Every Night is Girls Night

Grae Phillips is still active
on Facebook if you want to 
see more. Or just keep up. 

I know I make a big deal out of my second huge transition, when I mentally moved from being a serious part-time cross dresser into being a novice transgender woman.

Sometimes I feel as if I am putting myself on some sort of a gender pedestal when I write about not considering myself a cross dresser anymore. If it comes off that way, I don't mean it to. On occasion, the written word gets in my way. Getting back to the cross dresser versus transgender statement I made, I think in my case, it was a matter of me judging my own life. Originally, as I was working my way through my early years of admiring my girl self in the mirror, I knew it could never be enough. There had to be more. I was so tired of cross dressing for one day and then two or three days later wanting to do it again. 

As I always mention, all of this occurred back in the pre-internet information era when any news and contact with like minded gender individuals, be they transvestites or transsexuals, was very difficult and rare to come by. This was even before the barrage of talk shows led by the late Phil Donohue who interviewed female impersonators such as "Grae Phillips", all the way to transvestites seeking approval from a doubting world. It was quite a bit for me to sort out. But I did. I knew I could never be as beautiful and talented as Grae but I could reach the standards of most of the transvestites I saw on my television. There was hope for my future after all.

As I progressed into meeting more and more diverse cross dressers or the women known as the new transgender group I began to think what it would mean if I went all the way and every night became girls night. In other words, a time when I would never have to go back to my old male self and live. Deep down I knew there would have to be some sort of line drawn in the sand if I did. As much as I loved all the fun of the newness of applying makeup and picking out clothes, I wondered what would happen when the newness wore off and I needed to settle into the daily routine of the transgender womanhood.

It turned out, I had nothing to worry about. I settled into my new feminine routine as if I had always should have been living this way. I found I didn't have to do much special on many days such as most cis-women do and then again still have the fun of dressing up for special occasions. It was true, once I jumped the gender border from cross dresser to transgender, I could experience what life could be like if every night was girls night.  

The Prom Gown

Image from Joeyy Lee
on UnSplash

Years ago, I received a prophetic statement from an unknowing doctor when our family was on vacation in Canada. 

When we were not out fishing with Dad, we played football on a hard-packed lot behind the fishing camp with a bunch of local kids. Being the budding football star I never was, I decided to try to play running back and was actually successful bulling my way through the opposing boys on the other team, for awhile. On a play I would learn to regret, I was picked up and thrown down on my shoulder and suffered a broken collar bone.

I say regret primarily because my Dad was not amused about having to interrupt his vacation to take me to a hospital for treatment. At the hospital, I had X-rays taken and was diagnosed with a broken collar bone. I was seen by a doctor and had my shoulder bandaged up in a sling and was told it would heal on it's own. Leaving only a tell tale bump which showed it had ever happened. Then the doctor said, since I would not be wearing any prom gowns in my future, it would not matter anyway.

I thought at the time, wait a minute! What if I wanted to wear one of the beautiful gowns I had seen on women in my future. What then. I think that comment hurt worse than the actual breaking of the bone. Plus, when I did go to proms and was stuck in an ugly tuxedo, I always looked at the girls around me for any tell-tale bumps to show a collar bone break. I never did see any. 

Along the way, I had several other instances of my feminine aura shining through. I have/had a nephew who from an early age developed a very unsavory attitude towards life which sometimes carried over to me. It started with my politics clashing with his right wing bigotry and going from there. On several occasions, he secretly complimented me by saying I threw a football like a girl. He even said one time when I bought my new Porsche Boxster, I had bought a girls car. Like I said, he was trying to hurt me but was secretly making me feel good. I could not wait to be the attractive blond woman in a sharp sports car.

There were other times when I was called feminine when I was doing my best to be a macho man. Several times at work, I was called "Ma'am" out of the clear blue sky in the middle of a normal conversation with a customer. Looking back, I think it was my feminine aura slipping through my male fence. 

Even though it took me years to realize my dream of living as a transgender woman was much more than living as a part-time cross dresser, I realized there were several tell-tale signs along the way. Maybe the doctor was trying to tell me someday I would want to actually wear a beautiful prom dress which showed off my collar bone break bump. Or my evil nephew would go on to having his own insecurities to deal with. I have not seen him for over a decade, so I don't know or care. He would probably just say he was right about calling me a girl. 

It turned out there were many people who saw through my disguise and at the least knew I wasn't who I was desperately trying to be. A stable, non toxic, productive man. I failed miserably and all I ever wanted was to be the one wearing the beautiful prom gown.   

Calling me a woman was the ultimate compliment.