Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

 Back when I managed a prominent casual dining/bar venue, we had two women who would frequently come to our bar after finishing their round of tennis. 

Of course, I always noticed and was jealous of their short tennis outfits. I immediately put acquiring some sort of a tennis outfit on my cross dressing to do list. Since I had always admired short mini skirts and dresses on women, finding a short mini white dress to wear as the primary part of a tennis outfit was a priority.

As luck would have it, I found the ideal dress at a women's clothing shop in a mall I always went to. Once I had the white dress, I discovered the rest of the outfit would be fairly easy to put together. I ended up finding an inexpensive pair of white tennis shoes and socks to go with the shoes. The only problem I had then was what I was going to do about the hair on my legs. 

Even though my wife knew I shaved my legs on occasion, she was not overjoyed when I shaved. Primarily because she worried, I was up to no good when I shaved my legs, and she was right. On this occasion, I could not wait to show off my legs and new tennis outfit in one of the malls I always went to. Before I went to the mall, as always, I needed to create the time to do it away from my wife's disapproving eyes. I waited until she was working a day shift, and I began the fairly intense process of shaving my face and legs. 

Once I completed the shave and applied my makeup and hair, I was ready to test out my new tennis look outfit on the world. Immediately, I felt the thrill of my shaved legs in the short white dress I was wearing. So out the door I went into the world. As I arrived in the mall, I noticed my supposedly admiring public was primarily made up of retired men in the mall just to walk and admire the view. Since I was the view, I wore a pair of sunglasses so I could watch their reaction to me without being obvious. It worked and I could see them staring at the tall blond in a tennis outfit.

As I saw it, I received all the pleasure from tennis without putting in all the work. Now all I needed to figure out was how to hide my extra women's clothing. On this occasion, I used a little used closet and hid my new treasured outfit among a set of my old male clothes I never wore. 

For a change, my ideas of how to come as close as I could to learning for myself how a woman would feel in a tennis outfit came together. I could show off my legs and have fun doing it. Plus, I could cross another item off my transgender bucket list. Quickly, I was off to another quest. 

The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

The longer we live as transgender women and trans men, often we find many aspects which represent a double edged sword. 

One of the edges of the sword has to be the duress we feel when at first we arrive in public for the first time. To make matters worse, we have no peer group to help us out of the mirror to be judged by the harsh eyes of the world. No one to tell us we looked clownish as we tried the makeup arts for the first time. I can't tell you how many times I hurried home in tears following being stared at at the least, or laughed out of a venue at the worst.

From it all, I learned to develop a thick skin and always go back to the drawing board as quickly as I could to help solve any presentation problems I might have had. Even when I was doing it, the cross dresser drawing board was certainly difficult to figure out. What happened was, I used the very brief moments of gender euphoria I earned and moved forward attempting to tightrope my way along the sharp edge of my sword. I was risking ridicule at the least and the loss of family, friends and employment at the worst. Failure as a transgender woman was a very real pressure.

Once I began to learn how to present in public more effectively as a transgender woman, I began to use my sword more effectively.  Then the world became much more comfortable for me in my quest to live my femininized dreams. In addition, my makeup arts became better as well as my use of hair to enhance my appearance. 

It bares mentioning also, going through the overall transgender experience, made me a more resilient person and set up to battle the more challenging times we face. I learned in my research transgender folk have always been around and always will be, no matter who tries to erase us. Battling the sword all these years helped me be more secure in my transgender identity. 

In all fairness to my sword, it started out very dull. I worked long and hard to sharpen it by going out in public which was the best indicator of my progress.  So I took all the good and bad and did the best I could with it. All my interaction with the public included the dark evenings when red-necks repeatedly kept playing "Dude Looks Like a Lady" on the juke box in a venue where I was a regular. Since management at the time would not support me, I left to find another venue and took my money elsewhere. I was rewarded months later when an employee from the venue I was discouraged from coming to, found me in another venue and invited me back. To make matters even better, the manager who would not back me up was fired for drug use. Excluding a stray bigoted woman in the woman's room, I never had any further problems there again.

Once my gender sword swung back into doses of gender euphoria, I began to appreciate all it had done for me. Transgender womanhood was finally mine to enjoy when I learned I was not a quitter and was in my transition for the long haul. 

Trans Girl at Black Friday

Woman Shopping on UnSplash.

As I advanced on my feminine path to transgender womanhood, at certain points I needed to do more and more traditional feminine activities which cemented my claim to be a trans woman.

One of those was joining all the women in the world who were out and about shopping for the bargains bright and early on "Black Friday" or the day after Thanksgiving. My second wife for years was part of the crowd and made sure she was one of the early shoppers. 

Of course, I always wondered what the attraction was to go out and battle all the crowds, except for saving a little bit of money. Finally,  many years of wanting to shop with my wife as another woman came to an end but suddenly, on the other hand, I had the chance to shop on "Black Friday" as a woman by myself. Along the way, my second wife became the assistant manager of a large bookstore and of course "Black Friday" was one of their biggest days. So, I knew in advance she would have to work and I arranged my schedule so I did not. 

On the morning of shopping, I was excited as I prepared myself for a morning I had only ever dreamed of. First I did all the shaving preparation, including face and legs. I needed to calm down before I dressed in my favorite bulky sweater along with my best denim skirt and comfortable flat walking shoes. Then I began the more crucial part of applying my makeup and wig after I had calmed down...somewhat. After I reached what I considered to be a good presentation which would blend in with all the other women shoppers I would encounter, I gathered my courage to leave the house and head to a nearby upscale mall which I was very familiar with.

Unbelievably, in a very crowded parking lot, I found a space close to one of the entrances. As I checked my makeup and hair for the final time, I thought back to all the times I wondered what it would be like to shop with the other women on "Black Friday" and here I was and into the mall I went. My initial reaction was one of calm because no one was watching me, they were on a mission to find the best bargains and complete their shopping lists to bother about a transgender woman in the crowd. 

Since I wasn't really there to shop anyhow, I just browsed a few stores and bought a few small gifts for my wife before my shopping came to an end. After all, I had accomplished my goal of experiencing "Black Friday" shopping up close and personal as my authentic self. It was another item I could check off of my transgender woman bucket list.

Time flew by and  I needed to be back home to change back into my old boring male clothes to go to work, I needed to bring my dream day to an end earlier than I liked. 

Possibly the biggest lesson I re-learned that exciting day was the power of blending in with the rest of the women around me. As long as I could accomplish looking similar to everyone else, I could present well enough to get by. My first Trans Girl at the "Black Friday" shopping experience was certainly worth it.

Trans Girl in a Wig Store

 

JJ Hart Blonde Look.

Perhaps I should say trans girl in as many wig stores as she could find. 

Once I arrived at the point where I could even afford a nice hairpiece, I was like a kid in a candy store. So many styles of wigs to choose from and so little time to try them all on. I wish I could say I quickly became better at the process of choosing my crowning glory. Sadly, similar to the rest of my outfits or fashion, I was going too trashy to blend in with the women in public. I was telling myself since I needed to overcome a large head and body, I needed large hair to do it.

Also, to find a wig store I had not been to, I needed to drive long distances. Primarily from my medium sized hometown which had no stores which specialized in wigs all the way to Dayton or even Cincinnati which had several. 

Once I made the trip, I needed to learn several of the shop owners were not really interested in how I presented in new hair but were very interested in how much I had to spend. The owners could not do much to direct me in the proper direction of what I needed to look better as a transgender woman. Being fair to them, my male ego was in the way, telling me how to choose because he thought I would look better. Many times, I ended up buying what I today call clown wigs which were guaranteed to get me recognized or clocked as a cross dressed man. The wigs were good for Halloween and not much else.

All in all, the choices were bewildering. I felt as if I was back in my beginning days in the makeup department when I was attempting to figure out what product I wanted to try. In the wig store, I had to choose a color of hair I wanted, style I wanted and even which hair I wanted, human or synthetic. The possibilities were endless. 

In the beginning, my default color was always red or auburn before I started to shift away to other shades. For years I rotated between dark colors and blond which became my favorite. I was enjoying the changes in my appearance until I needed to settle down into one look when people began to recognize me. No more changing my name with my wigs. Settling down was difficult but something I needed to do as I followed my path to transgender womanhood. 

Through the magic of gender affirming hormones and good genetics, I arrived at the point where I did not need to wear a wig at all. In fact, one of the best gifts I had ever received came from my daughter when she provided me with a visit to her own upscale beauty salon. Even though  the experience was terrifying at first, I ended up loving it and could not wait to go back. Almost immediately I understood why cis women spend so much time and money at their salon. 

Most certainly, I cannot overstate the importance of hair to our outfits and fashion as transgender women or cross dressers. Hair demands all the effort we put into it. 

Ditching Good for Better

 

JJ Hart with Ohio River.

As I made my way along my gender path, I was always looking to go from just good to better. 

I always wanted to present better as a girl my age all the way to moving like one and even doing my best to act like one. I did my best to be a keen observer of what the feminine gender around me was doing at all times.. If they were wearing mini-skirts, so should I was a prime example.

Sadly, I was hindered by my meager financial situation until I grew older and could afford more fancier accessories such as clothes and wigs. Even still, nothing was stopping me from pursuing my gender dreams of living as a woman. If only I could. That is where my path became more and more important. For example when I finally broke out of my closet and did all my own shopping, I learned the hard way what looked good on me and what did not. From there I could build on to my success and go from good to better.

I became especially good with my feminine business attire wardrobe. At thrift stores I managed to find a black pant's suit which paired nicely with heels or flats and my should length blond wig. I even had a wool full length coat to go with it for the winter time when I went shopping. For the warmer times of the year, I found a lime green business suit with a shorter skirt which I paired with pastel green opaque panty hose and matching kitten heels. I found I went from good to better either time of the year and presented relatively easier for the first time in my life. Gender euphoria at it's finest.

All of my fashion advances did not prepare me for face to face encounters with other women in the world. Chance encounters with store clerks were easy until I began to stop at restaurants to eat. I needed to order from a menu while at the same time doing my best to sound like another woman just having lunch away from her job. Until I gathered the confidence to practice it, the entire idea of talking like a woman was once of the most difficult things I had ever attempted.  I even went as far as going from good to better by taking vocal lessons to usher me into my transgender womanhood. 

I often think I inherited my drive to always do better from my parents. Nothing was ever good enough for them. If I had received a B in a class, why did not I get an A was the routine I grew up with. Imagine the irony my parents would have felt when they found I applied the same thought pattern to a gender issue they were very against. All I ever wanted was to be a woman, transgender or not and needed to work very hard to overcome my male bonds to do it. Plus I always felt if I was going to be successful as a transgender woman, I would have to try harder than the average woman to succeed. 

So along the way, I needed to not accept good and kept trying to achieve being better and better as a transgender woman. I wonder what my parents and my second wife would have thought of me now. Hopefully they would be happy for me, since I have arrived at the place I have always wanted to be in life. If I had done it sooner, I would have undoubtedly been an easier person to live with. 

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. 

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.  

What Now? More Steps???

Image from Henri Pham
on UnSplash

As I view my progression into a transgender lifestyle, I see it as a series of steps. In other words once I arrived at one step I needed to look around and see what was coming next. 

It all started innocently enough after I discovered I could wear certain items of my Mom's wardrobe and admire myself in the mirror. After that step, I found I wanted to shave my legs, put on hose and a mini skirt I found at school and head outside to check the mail at our house. I knew I was hooked and needed to figure out what was next in my life. 

The next step was very difficult to come by as I mentioned in yesterdays post., I needed to acquire the makeup and then learn how to use it. My next step upwards did not actually come until my college days when I was able to buy a wig I loved for a girlfriend I had, then keep it when we broke up. Finally, I could complete the total makeup and hair step and I loved it. It was around that time when I became brave enough to attempt to express my feminine side at Halloween parties. Immediately I began to learn new lessons from the experience such as how I was separated from all the male friends I had when I was cross dressed as a woman. I was excluded from the club.

From that point onwards I needed to decide if I wanted to be excluded from a club I worked so hard to be a part of. It was a huge step in my life when I decided I should and would give up my male past and go forward as a transgender woman. Little did I know, when I made the decision, so many steps were to come. Such as when I began to enter the world as a woman, I needed to concentrate on so much more than just look like one. I compared the process with taking a mirror image and then putting it into motion. I needed to concentrate on femininizing my movements and then undertaking the biggest challenge of all, communicating one on one with the world. Which meant mostly women since most men had the tendency to leave me alone because their sexuality was threatened. 

My steps then came quicker and quicker the more I tested the world. Confidence came when I successfully negotiated one step after another and was ready to move on. At times the process was not easy when I thought I was moving too fast. I paused and began to consider how much I had to lose if I continued on the path I was on. I was on a collision course with the reality of my true gender. My next step just had to be gender affirming hormones or HRT. Fortunately I sought out medical and therapeutic help and was approved for the hormones. A huge step as my what now was answered. My body took to the hormones easily and I was able to flourish. 

Finally I ran out of steps and excuses and decided to give my male clothes to charity. What now became the future and it was time to live a life as a transgender woman. 

Sitting Pretty

Image from JJ Hart.

It never took me being a genius to figure out my appearance as a woman would cost me much more than my male self ever did. 

I started out my feminine life innocently enough as I began to save my meager allowance to buy a few articles for my girl wardrobe. I even took on a rural newspaper route to add a few dollars every week to spend on whatever I wanted. The problem was, finding my way to a store where I could attempt to spend my hard earned money. 

Our family home was actually in a rural area outside of town and I needed to figure some sort of an excuse to make it into town by myself because all I had was my bicycle. I figured out the answer which came to me when I was asked to go in town and visit my Grandma. She just happened to live very close to the downtown area and probably would not resist any attempts on my part to go downtown alone. I knew also, there were several stores downtown which sold makeup as well as other feminine accessories. So close but so far.

Predictably Grandma didn't and I had free reign to go shopping on my own. Then, the next biggest hurdle came along when I had to actually go into a store and shop for any makeup I found that may be suitable. The first time I was brave enough to shop for my own makeup, I was panicked and just wanted to buy something and get out of the store. Another problem was my Dad worked a short distance from where I was shopping and if I was caught, I would have no answer to why I was buying makeup. He never did catch me and the only hurdle I needed to face was the clerk who would be checking me out with my purchases. 

I was able to visit Grandma and do my shopping with no problems except for my extremely limited financial resources. Even though I managed to buy appropriate makeup, panty hose and even shoes, there was no way I could ever afford a suitable wig. For years, the wig of my dreams was just a fantasy of mine. Even so, time flew by and I managed to survive, even with my gender issues. It wasn't until I was out of the military did I realize how much sitting pretty would cost me. 

Dressing head to toe as a woman still proved a challenge for me to afford. Most of my needs would be met by going to thrift stores in our area. By doing so, I was able to find fashion "treasures" which were added to my growing wardrobe. While the thrift stores were cost effective for me, so many other aspects of cross dressing myself were not. Due to the size of my feet, thrift stores were out and I needed to shop retail. The whole process of adding new makeup, accessories such as purses and jewelry was a challenge because for the most part, my wife had control of the family finances. Through it all, going to a wig shop and buying a wig was still very difficult and frustrating. What I mean is, once I was able to put together a quality outfit, I was still struggling with having a wig to finish off my look. 

Finally, my financial situation improved to the point where I could afford a quality wig but then I needed to figure out which wig I could buy. Initially, I was like a kid in a candy store and picked out the wrong wigs which made me look like a clown. Through all my fashion errors when I was out in public for the first time, I finally was able to buy the correct wig which fit me well and framed my face correctly. It turned out the wig was the final piece of my presentation puzzle. 

For the first time ever, I was able to do my best and sit pretty as a novice transgender woman. 

Then I Went and Did It!

 

Trans Girl image from
Alexander Grey on 
UnSplash.

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

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

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

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

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

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

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

Transgender. Complex or Simple

Is the art of being transgender very complex or simple? It depends on where you are in your gender transition cycle.

Anyway you cut it, femininization is a difficult process and I assume the same is true for transgender men seeking to enter a male world. In my past, I have had conversations with a trans man friend of mine about the trials and tribulations of using the men's room. The process seemed different to me because I had always taken for granted using the men's room and ignoring everyone else in it. I experienced a much different world full of complexity when I started to use women's room. Just making sure I looked another woman in the eye was a challenge, not to mention everything else I needed to remember to survive. 

Of course the biggest complexity was fashion, hair and makeup. Since we transgender women don't have the luxury of growing up feminine, we have a ton of catching up to do. It is often more painful than fun but is something we just have to if we want to ever make it to the simplicity side of our lives. In addition, the complexity of living trans comes full circle when it comes to our emotions. Then emotions lead to our overall mental health, so it has a very deep relationship with our everyday lives. If we are fortunate, we settle into and come to an uneasy acceptance of being our authentic gender selves is the goal. 

None of the conquering of the transgender complexities came easy for me. I needed to work my way through dressing as a teenaged girl in my mind all the way to being able to present to blend in the world successfully. I needed a whole new attention to detail if I was ever going to achieve my lifetime dream of being a fulltime woman, trans or not. It took awhile but I slowly adjusted my life to a much simpler mode which included being feminine. Fashion and makeup became second nature to me as well as the difficult attempts of dealing with the public which meant mainly with other women. 

There were so many serious facets of my everyday such as being to deal with such as what my sexuality was going to be. After all, since I was living as a woman, would I be expected to have sex with men. Since I had never had sex with men, I had no idea of what to expect. Would I have any pleasure, or would I have been doing it just for my own validation. Thankfully, I did not ever have to explore the new frontiers of sex as I found I was still attracted to women and my lesbian women friends taught me it was fine to be so. So the sexuality of my life didn't change and stayed very simple.

Life is complex enough on it's own without adding in the complexities of being transgender, so we face the ups and downs of following our paths. We somehow find we are carrying pocket knives to solve a problem when all I needed was a set of pliers. It was all part of the simplification process. All along I knew women live a more complex lives than men but adjusting our existences to fit was the challenge. Ultimately, I needed to accept the challenge to save my own life. On occasion, the complexities of learning a new gender world in my femininization process became too much and I needed to try to fall back and take a break. However, breaks were short because the more I learned about being a woman, the more I wanted to learn which was aided to a large degree from finally beginning gender affirming hormones. The new hormones simplified my life even further by aligning my inner and outer selves. 

Suffering through all the complexities of transitioning genders turned out to be so worth it for me. The long journey I took led me to a much simpler world I wish I had be able to know years ago.

Down the Transgender Rabbit Hole

 

Image from Benoit Baumatin on UnSplash.

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

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

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

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

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

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

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

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

A Night at a Concert

Image from the Jessie Hart Archives

Following the time when my wife passed away, I actually tried to date another cis woman, once.

During this brief period of my life, my old male self was still desperately hanging on to the idea he could still exist at all. At that time, one of my servers came into my restaurant with her very attractive Mother. After several inquiries I found her Mother was single and she would ask if she would go out with me. She did and we started our very short history of dating. 

Right from the start I found she was a bit of a prima donna when we met on a date in downtown Cincinnati. I suggested stopping at a micro brewery for a quick appetizer when she wanted to go to an upscale steak house on my dime. I should have known then she was out of my league but I kept on trying anyhow. In a very short period of time, I told my daughter I was dating again. In response, she came up with two tickets to a local park pavilion near her house. The concert performer was Joe Cocker, so I could not wait to go. I even asked the new woman I was dating if she wanted to go and she initially said yes and the date was on, or so I thought. A couple days later and a week before the concert in the park, she called me and broke up our brief affair. I was slightly shocked but then again not so much as I began to consider what I would go with an extra ticket to see Joe. 

At the time, I was increasingly exploring the world as a transgender woman, so I thought why not take myself on a date in the park. I knew exactly what I would wear .My long silky black slacks with my black matching sleeveless top and black flats for comfortable walking. I then applied my makeup and topped my outfit off with my long black straight wig and I was ready for the half hour drive to the venue. By this time all of this happened, I was becoming very comfortable with my feminine self so I was really looking forward to the evening as it approached. I had spent many a evening being alone with myself. I wasn't very nervous as much as excited by the expectation of having a good time. 

The evening of the concert turned out to be ideal weather wise, a beautiful warm but not too humid Ohio summer evening. I showed my ticket and was admitted to the venue without a problem. Before I went to my seat, I decided to buy a drink and then headed to sit down. Again I experienced no problems with anyone in the venue in my section. I was able to enjoy my drink and relax even further before the music started. I especially enjoyed the silky sensation of my clothes in the summer evening air.

I was glad I went because I had been a Joe Cocker fan since the Woodstock concert days and it wasn't too long following the concert, he passed away and I was still able to be completely enjoy his performance before it was too late.

As far as I was concerned and as selfish as it may sound, the whole exciting evening was more fun for me than taking a woman I barely knew. Plus my experience even further increased my confidence as a novice transgender woman. Even to the point of coming out to my daughter who I told that I enjoyed the concert very much but never added who my "date" was. 

The night at the concert was one of those lifetime experiences I will never forget. It was the last time I ever tried to date as a man and the first time I was ever to seriously explore my life as a transgender woman. Once I did, the more I understood it was the life for me. 

My Second Gender Transition

Liz on Left. Image from a Banquet we 
attended. From the Archives. 

 I am a firm believer,  I went through more than one major transition when it came to building a new life as a transgender woman. Many transitions were helped along by friends and others I accomplished on my own. 

One of the biggest I did all by myself was one I mention quite often. It was the night I went to TGIF Fridays close to me. Just going was not so amazing, in fact, I had been to the venue many times as my male self. When I was there, I often was very jealous of all the other women I saw there, many of which were dressed in fashion I could only dream of. 

All of a sudden, I decided to make my dreams a reality and one night I set out on an adventure which I would never forget and would change my life forever. I can't really tell you why but something clicked deep inside me and I decided it was time for me to move away from being a cross dresser and explore my possible existence in a transgender world. The whole possibility terrified me more than anything else I had ever tried before in my life. Possibly because I knew if I was successful there would be no turning back. 

To begin with, I had the wardrobe I needed to wear to blend into the feminine environment I was headed. I knew the Friday's venue I was going to had a very woman based clientele which came every night at approximately the same time from a large mall which was nearby. I knew exactly, who I was trying to blend in with when I chose what I was going to wear. I chose my dressy black pantsuit, black flats, sensible makeup along with my shoulder length honey blonde wig. I felt I looked presentable enough to accomplish my goal of moving into the transgender world I was just beginning to explore. 

Once I came up with a time I could sneak out for a trip into the unknown when my wife was working late, I began the transformative femininization process. Once I thought I looked fairly presentable, I left for the twenty minute trip to the venue. Through it all, I was scared but not as scared as I would be when I arrived at the Fridays. When I pulled into the parking lot, I ended up waiting over a half a hour as I adjusted my hair and makeup in my car's rearview mirror. Once I came to the point where I could barely breathe, I opened the car door and gathered myself the best as possible. After all, I had improved from the point of not being to breathe at all to being able to walk in the front doors. 

Since I managed a similar casual dining venue to a Fridays I knew the setup, Essentially, once I made it past the hostess stand, all I had to hope for was being able to find a vacant seat at the bar. I was lucky I arrived shortly before the rush and there were several seats available. The Fridays I was going to had not remodeled yet so it had two big supports on either end of the bar. I was so scared and so lucky, I was able to get a seat next to one of these supports. I got as close as I could and tried to hide until I was approached by a friendly bartender and order a drink. From that point forward, I knew my life had changed forever. Just existing as a woman among other women in a public setting had removed any idea's of being a casual cross dresser ever again. 

In a moment, my second gender transition had taken place. My first came years previous in my youth when I viewed myself as a girl in the hallway mirror. Plus, deep down I knew the next transition I would undertake would be if I could ever undertake gender affirming hormones or HRT as it was known as back in those days. My visit to Fridays that night jump started my gender future. My problem then became how I would ever be able be able to co-exist with my un-approving wife ever again. She was certainly against being with another woman. Especially if the woman was me. So my second transition was heaven for my inner woman and hell for my wife and my marriage.  

Of course, I was able to transition even further with hormonal therapy and go on to lead a comforting transgender life. Going through the process was always not the easiest and I will always remember how I felt that night at Fridays from trying to hide behind a post all the way to how my panty hosed feet felt in my flats. It was quite the evening.

It's Game Day

 

Red Wig Image from the 
Jessie Hart
Archives and the game...

Recently, the Cincinnati Reds kicked off their latest professional baseball season. Opening Day is a big deal here complete with a parade and sell out crowds at the game. 

As a guy, I somehow managed to secure a ticket or two to the game because the company I worked for knew I was a huge sports fan and it was their way to keep me happier. As a transgender woman, I also managed to go to a few games but never opening day. As I aged, the problem became when I was unable to walk long distances to get to the ballpark and had nothing to do with me worrying about being accepted by the other fans in the stadium. Plus what remained of seeing the whole sporting experience in person as a woman just reinforced the fact I could take my love from one gender to another. 

I was lucky when I found and was accepted by a small group of women who were passionate about sports also. We regularly gathered at sports bars to watch our favorite teams play while we drank quantities of good cold draft beer. Good times were normally had by all, even though our teams lost. Perhaps the best part was, since I was part of a group of other women, no one questioned my gender at all. I had my validation as a person I so desperately sought. 

With one of my friends (Kim) a friendly competition developed over which professional football team we were fans of. Her family is from Pittsburgh, so naturally she is a Steelers fan which collided head on with me since I am a Cincinnati Bengals fan. Along the way, we became so close she invited me to go along with her family to a Monday Night Football game in Cincinnati. All of a sudden, I realized what such a major deal going to a real live National Football League game was when it came to my gender transition timetable. For most of my life, I wondered what it would be like to attend a game as my authentic transgender self and all of a sudden, the time had come. 

Back in those days, I had not started gender affirming hormones yet so all I had to wear was a barely fitting wig Kim and her daughter Hope had always seen me in. Hope was a bar tended/server at one of the venues I became a regular in and initially set up a meeting between her lesbian mom and I. Needless to say, I was terrified yet still excited to take another major step along my gender path. The door to my closet was opening faster than I had ever dreamed it would. Once I made it to the stadium, it was dark which helped my presentation and I went through the initial stadium security check points with no problems and my confidence began to build. We made it to our seats and no one gave me a second look, so I was happy. After all, everyone had paid a premium price to watch a football game, not a stray transgender fan in the stands. 

The only perceivable problem I was going to have was how much I could drink. I didn't want to chance going to the women's room if I could help it but I couldn't risk having to go during the long road trip home if I had to. So I compromised and just had two beers and made only one trip to the rest room where nothing happened. I got in, took care of business, washed my hands and got out. 

Per norm, the Bengals lost to the Steelers that night, so I took some abuse from the others in the group. Little did they know how just going was a complete victory and confidence builder for me and to this day, I can't thank Kim enough for including me.

These days, the Cincinnati Reds have a young exciting team who are fun to watch and my dream is to build myself up to the point where my wife Liz and I can see a game or two this summer. 

The Blue Coat

Image from the 
Jessie Hart
Archives...

Many years ago I frequented a wholesale coat store which seemingly carried an endless inventory of women's coats including many in my size. Which was rare.

I used to make the store a regular stop on my circuit of favorite places to haunt looking for a coat I could not afford. Even at the store's sale prices, finding one would still be a struggle.  One day I was there was an extra special day when I saw and then slipped into a powder blue wool lined three quarter length coat. Once I tried it on, it was lust at first sight. It seemed to fit in perfectly with my honey blond shoulder length wig I was so fond of. 

The problem I had was one of the usual ones many of us encounter as novice cross dressers or transgender women have, And, where is the money coming from for our new fashion discoveries and would the new fashion really be worth it in the long run. At that time, I was still struggling to hide any extra money I could from my wife who was a trained book-keeper and kept track of our finances. If I was going to my usual thrift store, it was easy to hide my limited expenditures from her and not be afraid of making a huge fashion mistake. If I did, I could simply take the item back and let someone else make the same error without losing much money in the process. 

This time though, as much as I wanted to, I couldn't leave the thoughts of how great it would be to be able to buy the cherished blue coat. In desperation, I kept going back to the store and then modeling it in front of one of the many mirrors. At one point, I wondered if I was parading the coat so much that someone would finally notice me and tell me to buy the coat or leave it alone. Luckily, that never happened but on the other hand I was never able to get together enough cash to purchase the blue coat and make it my own. Plus I had no idea where I would be able to hide it where my wife would never notice.

During this point of my life, I was completely entranced or obsessed with looking like a woman. Particularly a well dressed professional transgender woman in a mall or restaurant. My wardrobe at the time included a black silky pantsuit I loved as well as a pale green jacket I paired with a matching mini-skirt and kitten heels. Those were the days of colored opaque pantyhose and I even managed to find a pair of hose which also matched my outfit perfectly. 

Ironically, when I look back to a decade or so ago when I started this blog thanks to urging on from friends such as Connie, I can't believe how much I have changed. In the early days, I still believed being a success as a potential transgender woman was just looking the part. As I progressed I learned I was so naïve and I was looking ahead at so many layers of learning what it really meant to come out as my authentic feminine self. Leaving the mirror behind and entering the world was terrifying and extremely challenging at the same time. All the years I spent studying the women around me helped but I discovered it was only the beginning. 

Through it all though, I still remember how much I wanted that blue coat and wonder if I would have continued to cherish it as much as I did in the beginning for years. Or, similar to so many other lustful encounters in my past, it would have lost it's newness and just fade away.    

Never Give Up

Image from Amin Rk 
on Unsplash

 Similar to so many transgender women or men, I live a fragile existence. Or I should say for the most part I lived a fragile life as a cross dresser.

These were the times I was fighting totally any feelings of being feminine. Naturally, my ingrained male self fought the entire idea completely. Several times when I was caught cross dressing in front of the mirror, I gave up and decided to "purge" (or throw out)  almost all of my feminine belongings. I say almost because every time I stopped purging, I stopped just short of throwing out my favorite wigs or dresses. I guess deep down inside I knew I would need the clothes or wigs again. And I did because I never gave up on my dream to live as a fulltime transgender woman. 

By never giving up, I had several obstacles to overcome along my gender path. Everyone goes through tough times in their lives and looking ahead, I could see many more on my horizon. Mainly because, I was far from a natural when I looked at myself in the mirror. How could I ever turn a rather gruff bearded overweight man into a presentable trans woman. 

First things first. As soon as I could the beard had to go along with the weight. The first part was easy but the weight wasn't. Fortunately, I was able to cut back on a few fattening items and let my still robust male metabolism do the rest. In no time at all, I was able to lose nearly fifty pounds which helped completely in finding women's fashion in my size. At the same time, I started to concentrate on my skin. After shaving, I made sure I used a good moisturizer to aid in the process. I learned how much better my foundation looked on my face when I cared for my skin, plus by shaving daily, I was exfoliating my skin very effectively. In my case, along with practicing "extreme" shopping methods for fashion, I was able to do better in presenting my feminine self to the world. I suppose you could say, the whole process was a labor of love.

On occasion, I am amused when someone thinks my gender journey into trans womanhood was an overnight success. They never saw or understood the "error and trial" methods I went through when I first began to explore the public as a novice cross dresser or transgender woman. The most important moral to the story is I never gave up. No matter how difficult and bumpy the path became. Why? 

The easy answer is no matter how hard life became, deep down I knew what I was doing made me feel so natural. I felt if I lived long enough, I could leave my old male self behind and finally live in the world as a trans woman. 

Destiny proved me right and I was able to fit into a life in the world, I had always only dreamed of. I learned the hard way to achieve any goal in life, you never can give up.

It's All About the Hair

When I was very young the thought of ever being able to afford a nice, quality wig was the impossible dream. Since I was forced into the fashionable boy haircuts of the day ( a short burr or crew cut), I couldn't even begin to approximate having girls hair when I dressed up. I can't even remember wearing a towel around my head to look more feminine. Somehow, I made do until years later I was able to buy the first wig of my dreams, a sleek shoulder length blond hair piece I loved. In fact I think I bought it originally for my first fiancé and then managed to "inherent" it from her when we broke up. Something like you keep the ring and I will keep the wig. Definite priorities, right?

After I maintained ownership, that hairpiece managed to travel with me around the country when I was able to hide it in my baggage. I learned to be very skillful as I packed a small "collection" of women's clothes with my regular wardrobe. Now, as I fast forward several years to another time in my life, I found myself with enough freedom and financial resources to try and buy several ill advised wigs. I conservatively estimate I bought ten in a years time and of which, only two should have been worn in public. 

Finally, after I started hormone replacement therapy, my own hair quickly grew to a point where I could follow my daughter's lead and go to her salon and have it styled. At that point I felt I was truly making serious advances in my MtF gender transition. I loved fixing my own hair but it was an experience having to learn to take care of the back of my head also. No longer did I just have to rely on turning a wig head around and brushing it out. Paula, from the "Paula's Place" blog wrote in and commented on her similar experience:

Photo Courtesy 
Paula Godwin

"I note your comments about acting, there was a moment when I abandoned the use of a wig, for the first tie I felt as though I wasn't in costume and wasn't playing apart. I was dressing as a woman, I wasn't pretending to be woman, I simply was a woman, I was me. Additionally that was when I first started to understand that in all those (oh so many) preceding years I had been playing a part ~ I had been pretending to be a man. Now I could start being me instead of playing the part society expected of me."

Thank you Paula. I agree with your comment on so many levels. The blessings bestowed on me from being able to undergo HRT therapy among other things accelerated my hair growth and I was fortunate not to have any vestiges of male pattern baldness. 

The "costume" comment resonated with me also. Very quickly, being able to do away with wigs and wear my own hair helped me with my gender dysphoria. In other words, I was able to settle in physically to being my authentic self. 

I too was able to convince myself that all those years of being a cross dresser, I had it all wrong. I wasn't cross dressing as a woman. I was fooling myself and was cross dressing like a man. 

  

Wigging Out

 Recently I wrote a post which detailed a few of my trials and tribulations I experienced with wigs before I was able to grow my own hair to a feminine length. Ironically, one of the first things I noticed was all of the sudden I had to somehow see the back of my head to check out my hair. No more easy out by using a wig head and stand. 

I received plenty of responses by readers who commented on their own wig experiences. Including Monica who currently is up to owning five wigs. I am sure at my height of "wigging out" I owned many more than that, so I understand the attraction. After all, wigs are a natural extension of our makeup and seemingly (at least for me) there was always another wig which would take me to the promised land and I would become the attractive feminine person I always wanted to be. Plus, I feel I was attempting to overcome the days of financial challenges when I couldn't afford much at all when it came to a hairpiece. 

It turns out, I wasn't alone when it came to being a struggling novice transgender woman on the search for the best possible hair. As has happened many times over the span of our lives, Connie and I share quite a similar history:

"At the age of 34, I was married with two young daughters. We’d just bought a house, and I was anxious to fix up the unfinished basement to make an office for my part-time business, as well as shelving for storing all of those seldomly used things, such as holiday decorations. I’d already put a door with a lock on it for my office, and then, late one night, I started organizing things on the shelves. When I got to the Halloween box, I took a peek inside. There it was: that black wig, along with all sorts of makeup. Now, I had worn that wig a few times on Halloween before, but it had been part of a monster-type of costume when I had. On this night, though, it brought back every memory of my feminine-self. I took the whole box, along with an old mirror that was in the basement, into my new office and locked the door behind me. Doing the best I could with what was available, I put the wig on my head and made up my face. Looking at myself in the mirror, I remember whispering, “You can do so much better than this.”

Photo Courtesy Connie Malone

Money was a little tight after just having had bought a house, but it was probably more on my mind to rebuild a feminine wardrobe and accessories as cheaply as possible out of my renewed guilt. My wife had a basket full of makeup that she’d given up on, so I could easily take what I needed from that. I ordered a dress, a pair of heels, and some undergarments from the Sears catalogue, which I could discreetly pick up at the store’s will call. A new wig, though, was more difficult to find without, I thought, outing myself. Somehow, I discovered that K-Mart sold wigs, so I got what I determined to be the best one that was available at the time. It was brown in color, just as my mother’s wigs were, and somewhat contemporary in style (as contemporary and stylish as one might expect to find at K-Mart, anyway). I remember shunning the blonde wig, at the time, as I thought it to be “overdoing it.” I bought that wig, along with a set of wrenches as an attempted cover, and thus began my return to the pursuit of womanhood."

Thanks for the comment! It's amazing to me how the slightest trigger object can lead us back into fond memories of our feminine pasts. Mine was a long blond wig I fell in love with and managed to buy for my then fiancé. She wouldn't wear it but of course I would. That hairpiece managed to stay with me for many years. Even surviving my time in the military and several ill fated "purges" I attempted when I resolved myself to never cross dress again. That really worked out! I haven't cross dressed as a man for nearly a decade. 

I can't make the point enough. I am so lucky to have been able to grow a full head of hair. Now I have to get back to a salon and let a hairdressing professional take care of it. Before it begins to appear as if I have been wigging out.  

Material World

 This actually was posted in 2021 in Cyrsti's Condo but is still relevant today:

And, as Madonna would say, I am a material girl. Then again, don't all of us have to be one way or another? Unless you are living off the grid and probably aren't reading this at all. 

Picture after first hair appointment
Credit: Cyrsti Hart

Actually, I am a very basic transgender woman. Give me a comfortable pair of jeans or leggings, add a tank top and tennis shoes and I am happy and secure as the transgender woman I am. Ironically as basic as I am, I still dress more femininely than my partner Liz who is a cis gender woman. Meaning she was assigned female at birth.

Backtracking a bit, when I first began to explore the feminine world in public, I was much more materialistic. All my accessories such as jewelry, purses, shoes etc. were so much more important to me. All my attention to detail worked too when I was complimented on my appearance by other women. 

All went well until I really started to transition, aided by the effect of hormone replacement therapy. One of the first changes that happened was I was fortunate and my hair really started to grow. So much so that my daughter gifted me my first visit to her upscale hair salon as a birthday present after I had come out to her. The visit remains in my mind as one of the most exciting yet scary experiences of my life as I crossed the gender frontier. Having to walk the "gauntlet" of women who had nothing else to do but to watch and judge me was amazing pressure to say the least. 

I learned too, it was a material world when all of the sudden I was paying to have someone else take care of my hair. My old twenty dollar haircuts at a barber shop were long gone. Also when I was going out, I had to learn there was a back to my head also. All those years of wearing a wig had spoiled me. Of course I could simply turn the wig around on it's stand and brush it out. 

Another of the main problems I faced as I MtF gender transitioned was the cost of trying to maintain two wardrobes. Along the way I was biased because shopping for the feminine side was so much more fun and satisfying. Once I settled into my feminine natural role and quit cross dressing as a guy, of course the costs went down.

I suppose it could be argued we all live in a material world. Transgender women may experience it all in such a unique way. which is nothing different in our overall experience. Once I decided to take the total leap of faith and transition into my authentic feminine life it was as if a giant weight had been taken of my shoulders. I was so tired of fighting my gender dysphoria. 

Finding myself in a material world was well worth it.