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.

Now What? An Adventure in Sexuality

 

Way back when, even though I was trying completely to transition into a transgender woman, I had never given much thought to any potential changes in my sexuality. I couldn't see myself being with a man except if he was validating me on his arm as a woman. All of those thoughts changed when I met the guy and his bike. For you purists I think he owned a classic Indian Bike. 

I'm sure through out the years I had some sort of tunnel vision about my feminine appearance. Even though I wanted male validation from how I looked, I could never imagine really being with a guy.

Of course gender and sexuality are two separate terms. For simplicity, gender is how your perceive yourself as a woman or a man (or somewhere in between.) Sexuality is which of the binary genders you wish to have sex with. Again allowing for desiring both genders is a possibility. 

Somehow growing up wanting to be a girl rather than just look like one didn't allow me the idea of being sexual with my own gender. Looking back at my high school and early college years though, I think I did have a crush on one my closest male friends. A crush which would forever remain a secret. 

As life progressed and I interacted with my second wife while cross dressed as a woman, I had a  chance to experience what gender life would be like from the feminine side. On one of the trips we made together to a transvestite mixer we decided to stop at a tavern for a drink before we went. As we sat at the bar, a guy parked his Harley motorcycle by the front door and ended up sitting down next to my wife. He ended up having quite the conversation with her and ignoring me. So much so I wondered if she would end up leaving with him to ride on his bike. Of course I was helpless to do anything and let her take control of the situation. It was a feeling I would never forget when she didn't go anywhere with him. Ironically, years later I would another interaction with a man and his motorcycle of my own.

I have written how quickly I arrived at the "now what" moment with him too. He was as sensitive as he was gruff looking and totally validated my desire to be a woman. I remember wishing at the time I didn't have a wear a wig (and had my own hair) so I could beg a ride with him. But the wig I wore just didn't fit that tight. I could only fantasize what it would be like to ride with my hands around his waist. But a fantasy would all it would ever be with him.

Later in my transition, I did have a few other opportunities to date other men. In fact one of my first dinner dates with a guy was with a trans man friend of mine. A couple other dates went relatively well but overall I had a difficult, even miserable time finding a date with a man. On the other hand it seemed I was finding my interest from women was reaching a all time high. At first it confused me until I learned to relax and enjoy it. I have written in depth about my success (to this day) with lesbians. On the other hand I was able to befriend several women and their husbands too. I suppose being a gender hybrid has it's advantages.

To this day, now what never became a reality as I have never been with a man. Years ago I had a cis woman friend of mine who said get a banana and practice. Rumor has it, I did just in case. Or should I say "Justin Case". I only know Justin wasn't riding a motorcycle. 

Inspiration is Fleeting

Or is it? Every morning when I wake up, I do a quick self examination of my body to see what hurts the most, or at all. Very quickly I then move on to thinking about the blog and what I have written about in the past. Every now and then, I come up with a former experience from years ago in my past.

Plus every once in a while, I am able to find a picture to aid in the story. An example is this picture from a decade ago in 2010.  Somehow, I was able to come up with my own version of primitive photo shopping on my cell phone. I did it by taking my picture in a mirror so I could see myself as I did it. My goal was to take a picture to add to my profile on the multiple dating sites I was exploring. 

The hair in the photo was a wig of course. Ironically my hair currently is as long and nearly as wavy if I add a liberal amount of mousse after I wash it. 

It's also taken me nearly a decade to grow my own breasts which were comparable to the forms I wore back then. Of course I am fortunate to have been able to undergo hormone replacement therapy at my age.

So, inspiration for a blog post is fleeting when I am well over 6,000 posts written for Cyrsti's Condo.

One good thing about the picture is, it is the one my partner Liz saw and decided to respond to me because I had "sad eyes". At that point in time I did. 

It was taken before I found a circle of accepting friends who helped me transition and gain a whole new level of inspiration.
 

What Came First...the Wig or the Name?

Recently, I wrote a post here in Cyrsti's Condo about my early cross dressing days when I would on occasion change my name to match (in my noggin) the spirit of the wig I was wearing. For example, I had exactly the wrong wig choice for me when I bought this big curly platinum blond wig. When the mirror lied to me and I wore it, I would change my name to "Roxie." I had so many other names back then I forget most of them. Most importantly though, I was successfully and needlessly confusing anyone I met when I foolishly tried to change my persona. After all, how many cross dressers were they meeting? I certainly wasn't accomplished enough yet to present feminine consistently.

I managed to confuse Connie and a few of you when I wrote this post. Here is her (Connie's) comment and her own story:

"LOL Forgive me, but I'm laughing at your mistakes, too. Naming yourself according to the wig you were wearing! I think that the name of the first wig I got by mail order was "Sultry." I may have felt a little sultry in it, but I was far from being that way, I believe now. :-) I learned, pretty fast, that gay bars were not necessarily the friendliest places for a trans woman.

Then, again, I also learned that they could be too friendly, when I was hit on by a very large drag queen one night. I was with two cross dressers, who did nothing but laugh at me, as the drag queen moved in on me with a vengeance. It was all I could do to resist the unwanted attempts of molestation and grinding against my hip as I sat on the stool. This is not one of the occasions for which I can look back and laugh, but it was definitely one from which I learned some things - about myself, as well as others. My first solo trip out was about six weeks after I had ventured out of the house to attend a cross dresser meeting for the first time. It was a trip to a grocery store across town to do the shopping for Thanksgiving dinner. 

I've always done the grocery shopping in our house, so there was some level of comfort in doing something that was routine to me. While sorting through the pile of frozen turkeys, a woman asked me how big of a bird I thought she would need for her large family. From there, after a rather long chat, I ended up writing out my cornbread stuffing recipe for her. Later, when I requested some cheese at the deli counter, the woman there responded with: Oh, that voice! Your voice is so...so...sultry...I love it! No, I was not wearing my Sultry wig, but I do think I was making a rather cheesy attempt at feminizing my voice. :-)"

You should have not resisted the drag queen! She may have changed your outlook on life! :)

Trial and Error

Over the past decades I have learned the hard way there is no easy way for most of us to feminize ourselves and face the public. I can't tell you how many times I was brought to tears by people snickering at me.

What happened though was I developed a thick skin while I learned to take better care of my own. Also ironically the more harassment I received, the more determined I became to present better in public as a woman. The more I progressed, the more natural I felt and over an extended period of two things happened. Probably the most important was gaining all an important confidence. More and more any resistance to me from the public was their problem, not mine.

Equally as important and a factor which took me years to research was how far reaching my possible transgender leanings went.  All of a sudden, I decided to throw my easy cross dressing trips shopping out the window. Even I learned clerks in stores didn't care who I was compared to how green my money was and easy trips to quiet book stores didn't really challenge by goal to be more feminine.

Finally I decided I had to take steps to establish myself as more than the occasional cross dresser if I was ever to explore if I could ever live full time as a transgender woman.

Here was my method as I have written about before here in Cyrsti's Condo. First I had to try to take a realistic look at what I wanted to accomplish. Little did I know how quickly I could establish myself after I quit doing dumb things like basically changing my name to match new wigs and going to gay bars looking for acceptance.  An example was when I dressed to match all the other single professional women that first night when I slid into an upscale bar stool at a Fridays outside of a close by busy mall. Make no mistake, I was scared to death! I still remember what I wore and each and every emotion like it was yesterday. Basically I wore a black pants suit with flats. With my restaurant/bar experience, I knew once I made it past the hostess stand with no problems all I had to worry about was finding a seat at the bar.

To make a long story short, I ended up becoming a semi regular at the venue and was treated well over the years.

Of course others have different yet similar experiences. Let's check in with Connie:

 "I must say that this is certainly the time for 2020 hindsight! :-)

There's so much more for a trans woman to change than just her clothes. If only it were that simple for most of us. When one becomes uncomfortable with what had once been her comfort level, pushing a few limits is then necessary. Although there are copious amounts of information and anecdotal stories that are readily available, we all must subject ourselves to some personal trial and error, if we expect any change. Learning to laugh at one's own mistakes, and to celebrate the successes, is a change for the better."

So true! Thanks!

From 2010

By accident I just found this ancient picture of me from all the way back in 2010. Again in one of my favorite wigs.

The more I started to go out to the same places though, the more I found the need to settle down to one basic look. The public needed to see me the same way to give me positive feedback in my Mtf gender transition.

Some of you long time readers of the Cyrsti Condo blog may remember.

We Got Mail

I received two great comments about the Cyrsti's Condo post yesterday which primarily revolved around accepting compliments and hair. The first came from Paula across the pond in the UK:

"I found that it was only when I abandoned the wigs that I began to truly be me, before that I was always playing a part, maybe it was two different parts, but still playing acting. When I could start wearing my own hair it became real!

I think the thing about compliments of common to a lot of Trans women; we were programmed like men, we were expected to give compliments not to receive them, it goes against all our conditioning to simply accept the compliment and say "Thank you".

Excellent points Paula! As I wrote before, I was exceedingly bad at attempting to buy the right wigs. For the most part, I was either trying to go more blond or with more hair than I could pull off. 

Now, let's check in with Connie:

"I was once told by another trans woman that I would never be able to transition successfully because I wear wigs - no better than a "professional cross dresser," she said. Having a good head of hair is definitely a luxury for a trans woman, but it's certainly not a necessity. I know that I am, at least, more of a lady than she is, and some people may be no better than a "professional bitch," I suppose.

I receive compliments on my hair from time to time. Some may not know that I'm wearing a wig at all. A friend I've known for five years did not realize that I wore wigs until just a few weeks ago. She had invited me to spend a girls' weekend with her at a nearby casino, and I must admit that I accepted the invitation with some trepidation. I was flattered that she felt accepting enough to be sharing a hotel room with me, a trans woman, not to mention that she also felt safe enough to be doing so. I wasn't sure how I was going to conceal all of the causes of my dysphoria, including my bald head, and her touting the wonderful pool and spa that we could use did not help. I finally told her that I don't swim because of my wig, and I don't think she thought any less of me for wearing one.

It's been years since anyone has seen my bald head. Even I will spend as little time as possible looking at it. If it's not a wig on my head, there's almost always something covering it - whether it's a turbine or just a towel wrapped around it. I will sleep in a wig if there is a chance that someone may see me. I did it with my friend in the room, and I even left my eye makeup on for good measure. Everything else was covered up, too. ;-)"

Thanks Connie! I think Stana of Femulate  blogging fame is another transgender woman  who does an excellent job with her hair and shows having your own hair is not a necessity for a successful Mtf transition. In fact it sounds like one of those "I'm more trans than you" statements. 

I'm sure too, since I have opted not to have any genital surgery some would think I am no better than a professional cross dresser too. Regardless, I have decided to do the very best I can! 

The picture to the right is one of me in one of the few wigs I bought I really liked.

Off to See the Wizard

Or...at least off to attend another Veteran's Administration transgender support group meeting.

It will be interesting in a sense if I can relay what I learned at the Trans Ohio Symposium. Including feminizing vocal sessions and free wigs and breast forms. As I wrote before, with the increasing numbers of woman vets the VA is seeing now, wigs and breast forms aren't so surprising.

Hopefully, the meeting will be attended too by the person who always complains about the VA not doing more for it's transgender veterans. Basically, you can get help with HRT and not much else, such as surgery. I can hear her now...she doesn't need breast forms, has already bought a wig, so where are the make-up classes???

Regardless, I think I am going to wear my tight jean style leggings along with one of my new lightweight gauzy tops for the trip.

Plus, in case you are curious, the car is back and no (Connie) it isn't old enough to have the the side "wing" windows. It's a warm day though, time for the "270" air conditioning.   Roll down two windows and drive 70 miles per hour. I may have to wear my hair pulled back today!

Wiggy?

Of course, the best way to ruin the wonderful outfit and make-up look you have carefully crafted, is by having a less than attractive wig.  Back in my wig days, I am sure I tried all the wrong wigs before I settled on a couple I wore quite a bit. The one I wore most was a long straight blond wig, which I actually have a couple pictures of to pass along.  (Circa early 2000's))

I am far from the expert to ask but I know I always washed my wigs in baby shampoo and was careful to make sure the caps were dry and they were properly brushed out before I wore them again.

Another friend who knows much more about wigs than I wrote in to pass along her ideas:

FABULOUSCONNIEDEEMay 16, 2018 at 1:17 PM

I might add that, as far as wigs are concerned, a good, moderately-priced wig will last just as long as an expensive one if it is properly maintained. All synthetic wigs will wear out and start to frizz at the tips after some time. Just as the fibers in clothing break down, wig fibers will, too. Imagine how long a T shirt might last, if worn every day (I hope you'd have to only imagine that). A cheap one from Old Navy might not hold up well to the everyday wear and the washings it would require. A good shirt will fair much better, but not any better than a designer T shirt.

I have a wig on my head about twenty hours of every day. I usually wear a worn-out one to sleep in, as I am too vain to be seen with my naturally bald head. I am fairly active during the day, so I literally glue my wig to my bald head. I started doing that after an incident where a low tree branch grabbed the hair off my head while I was getting out of the car in front of a busy Starbucks. The glue residue takes about a week off of the life expectancy of my wigs, but it's a small price to pay for the security. Normally, a wig will last six weeks for me before it starts to frizz and lose it's soft texture. Of course, I would recommend having two of the same style, and to rotate them between washings. When I can afford to do so, I keep a third wig to wear for special occasions, and then put it into the daily rotation after about 10 wearings. I usually wash mine every 5-7 days of wear. Putting product into a wig will make it dirty faster, and perspiration is a texture killer.

The wig style I am wearing these days is $60.00 when on sale. Ten dollars a week is a bargain when compared to keeping ones real hair colored, cut and styled. I'd gladly pay more to have my own real hair, but it was not my fate (damn testosterone poisoning).

BTW, use Woolite to wash your wigs. It's much cheaper than wig shampoo.

Thanks Connie and if anyone else would like to share their wig story, please make sure you send it in!

I might mention I finally found the salon location of the woman I want to cut my hair and she donates twenty percent back to a prominent transgender organization here in Cincinnati.  Now I have to get up the courage to go and do it. Back in my wig days, I also lost my wig to one of those pesky tree branches. Didn't do much for my confidence!

Historical Blond

Ironically I ran across two pictures in one day which illustrated my "blond days."

The first is a picture of a person in a wig very reminiscent of one of my first "real wigs."  For some reason, one of the beauty parlors I used to walk by all the time had a wig in the window (between all the ultra short conservative wigs) which looked just like the one on the left.

I was in love but could not figure how I could ever build up the courage or the funds to buy it.  Through a complex series of happenings finally I was able to convince my then fiance to buy it and then I "appropriated" it.  All of this process occurred in the early 1970's when I was still in college and looking dead ahead at being drafted into the Army.

I called the process years later a common one for a vast majority of cross dressers I knew.  Wasn't being the blond "bombshell" everyone's ideal?  Can't speak for "everyone", but it was mine. I ended up keeping the wig much longer than my fiance who dived on me when I went into the military.  (True Love?)

Years later, in the picture you see to the right was blond wig I literally wore out as I was solidifying myself as a feminine person. (Before, I would spend a week as a blond, the next as a redhead, etc.)

Ironically, deep down, I knew that my hair color (blond or not) should be tied in to my complexion not fantasy. Especially, if I was to be successful in my quest to live in a feminine world.

Now of course, since I have "inherited" all of my real hair, I'm able to play in the "real hair" world of women.  Essentially, dark hair in the winter and lighter in the summer. Through the miracle of hair colors I'm able to go back to my roots (and color them). My natural air color before the gray sat in was nearly black but I have a heritage of red heads from my Mom's side of the family.

Somewhere admist all of that though the old blond love affair still exists.