Under Twinkling Holiday Lights

Image courtesy Clifton Mill 

In my past, when I was progressing down my very difficult gender path and leaving my old male self behind, I began to try to experience new and exciting things. 

Part of my plan was to experience activities I enjoyed as a man and experience them as my new feminine self who was enjoying the time in the public's eye. Keep in mind she did not  know how being in public would work at all. She had so little time having done it. 

One of the activities my second wife and I enjoyed doing on a regular basis was taking the short trip to a vintage working grist mill It has become famous in the area for it's Christmas decorations To put it all into perspective, the venue says there are four million lights although I don't know who is patient enough to count them all. None of that mattered to me as I planned for my chance to experience life as my authentic self which was becoming much more than an impossible dream. At the time, my second wife had not passed away as yet and I was very much sneaking around behind her back when I cross dressed as a woman and left the house. I arranged my work schedule to have a rare Friday night off, knowing she would have to work because she was in retail as a manager of a major book store. My plan worked to perfection and in the holiday season hustle and bustle she indeed had to work. She knew all along of my cross -dressing desires but drew the line at me going public as my feminine self. 

As the time went by, I needed to plan what I was going to wear for this all-important evening. I needed to plan for the weather and for my comfort at the same time. I knew the parking situation at the Mill was not the best and I would need to walk a distance to see the lights and holiday displays. For the evening, which turned to be an ideal mid-December, chilly winter evening. The moon and stars were out and I was ready for the magic which was coming my way. But first things first, I had to choose my warmest, fuzziest sweater, leggings and comfortable boots which were suitable for walking. After putting on my clothes and makeup I thought I looked the part of an upscale woman out for a night at the Mill. Little did I know how wonderful the evening would turn out to be. Under the sparling stars and twinkling Christmas lights I finally would have the chance to live as the feminine transgender person I always felt I could be. 

Of course, the first obstacle I needed to conquer was the fairly simple task of stopping and waiting in line for a much-needed hot cocoa with marshmallows. Once I reached the front of the line, I was so nervous, I could barely order. I summoned every ounce of my courage to tell the woman behind the counter and in a low voice ordered my beverage. I was happy and my confidence grew when she smiled at me, took my money, and gave me my drink, and she even wished me a Happy Holidays.  From then on, I had to make a conscious effort to slow the evening down because I was moving so fast and not enjoying the moment as much as I should. From then on I slowed down and enjoyed being in the public's eye as the feminine person I always wanted to be. To celebrate, I even splurged and stopped at another concession for hot cocoa. 

What I remember the most about the whole experience was how heightened my senses were. The lights were brighter and twinkled even better than before. The only thing missing was a visit from Santa Claus himself. He was scheduled to appear later, much to the joy of all the kids in the crowd. In the meantime, I was able to shop the Mill's gift shop but could not buy anything for several reasons. The main one being having my wife questioning what I was doing there in the first place without her.

Before I knew it, I had seen all the animated attractions, plus the Santa doll display. All in full view of an accepting world which was a first for me. From that point forward I had the confidence to do more and more towards exploring the world as the person I always wanted to be. When I had the chance, I started to do the rest of my Christmas shopping as a transgender woman. I look back on my trip to the Mill as the beginning of a wonderful lifetime transformation. I discovered I could be me no matter how difficult the path may prove to be. Discovering the basic differences, the binary genders deal with was a major path to follow.

In many ways, the excitement of the first evening under the holiday lights would be a wonderful beginning to the life I was always destined to live. It was never as easy as walking among the crowds of people un-noticed sipping a hot drink, it was enjoying the totality of being myself. Which would become so increasingly complex as the years progressed in my life. All in all, the holidays lights were a wonderful, even magical beginning to a better life. Without knowing it, I was giving myself a wonderful holiday gift my inner self was wishing for. 

Sadly, time was up too soon and I had to head home to beat my wife there as well as take all vestiges of my makeup off my face. I knew one thing; I couldn't wait to experience such a fun night out again.  

Fear as a Motivator

 

Image from Amanda Jones
on UnSplash

Most of the time I can't remember the number of times I was paralyzed with fear as I pursued my gender path from a serious cross dresser to novice transgender woman. 

Examples include nights I sat in my car sitting in fear trying to figure out if I would go into the venue at all. Some decisions were easy such as entering gay venues but others were much more difficult.  Along the way also I made poor choices on which venues I was trying to go into which caused me to have more fear in the future. Mainly when I tried to visit redneck-ish places to see if I could present well enough to be accepted. The end result a couple of times were not good when I had the police called on me. I learned my lesson and was much more selective on where I went. It worked and the power of my fear was ultimately rewarded when I discovered venues where I could relax, have rest room privileges and become a regular patron.

There was a time when I considered the rush I received when I conquered my fear was a primary reason I cross dressed at all. Of course I finally realized fear was not why I wanted so badly to be a woman. The entire process went much deeper than all of that. What it did do was encourage me to go farther down my gender path. I set up goals I wanted to achieve. When I considered fear as a factor in future cross dressing decisions, it soon was reduced to just being nervous. Ironically, being nervous still sticks with me to this day. I need to push myself to certain restroom decisions because years ago, choosing the women's room was the primary reason I became a target of the public. By years ago, I mean the last time I experienced any restroom problems was nearly three decades ago but then again I am still nervous even though I know my way around the etiquette of using the women's room.  

Eventually I began to understand fear and used it as a powerful motivator. When I was considering not going to a party or a new venue I use fear as a reason to move forward. Of course now since it is rare I go anywhere without my wife Liz, we make a couple which keeps most transphobes at bay. 

Since I am mentally predisposed to having anxiety, I still have a tendency to worry about things such as me being mis-gendered again at my upcoming colonoscopy. Even though I keep thinking if that is all I have to worry about, I really don't have any issues at all...relatively speaking. I better begin to worry about the results of the exam as well as the unpleasant prep process I will have to go through before hand. 

It has occurred to me also, maybe I should have done a better job separating fear with excitement. My earliest days of exploring the world as a transgender woman were very exciting and the fear on occasion was a powerful motivator to conquer the gender anxiety in my life and move on. Plus, overcoming my fears gave me the all important confidence to move into a transgender life.  

Owning It.

 

Image from the Jessie Hart
Archives

Long ago I learned the hard way the power of owning my public appearance as a novice transgender woman or very serious cross dresser. 

I was tied too closely to my mirror and didn't realize until it was too late how it could lie to me. Examples included how the mirror told me I was an attractive woman who could go anywhere just to be bounced almost immediately by the public. Many times I would come home in tears wondering where I went wrong. Finally I came to the conclusion I was putting my feminine priorities in the wrong place. In reality my mirror was not in my house but was in the public's eyes. When I learned to dress to blend in with the other women around me, I began to own my existence as a transgender woman. No longer did I have to worry as much about being laughed at in public. 

Also, when I owned my life as a trans woman, I gained the all-important confidence I needed to follow and improve my right to exist in the world. If someone had a problem with me, it became their problem, not mine. The biggest pressure I faced was needing to communicate with the world as my transgender self. Suddenly the process went way past how I sounded into what I was saying. Owning the new gender world I was in meant learning to operate on an entire new spectrum involving an internal look at how the two main binary genders (male and female) communicated. Quickly I learned why men and women couldn't connect on the basics of communication. I learned also both genders put up a sort of invisible barriers when it came to talking to each other. Ironically, I began to be asked by each gender why their spouses or partners didn't understand them. 

I truly didn't find out why I had a key insight into both genders until I was allowed by other women into their world of life and communication. I learned the power of non-verbal communication as well as the seismic power shift between the genders. Basically the process is very simple. Men deal with power systems such as money and athletics when women deal with a more passive aggressive world. I was fortunate in that I was aware of how women formed smaller cliques (not teams like men did) and reacted passively aggressively to those with power. Such as management. When I was in my male management days, I learned the hard way if I wanted something done with my female staff, first I had to sell it with just a few key women on the staff.  Dealing with an alpha female was much different than an alpha male in more than the obvious ways. The ways I needed to learn if I was ever allowed to completely be welcome in the women's sandbox. I needed to win over the alpha females first.

I made it when I paid my gender dues and was able to own my life. The confidence I live with now is but a side benefit.

A Night at the Orchestra

 

Cincinnati Symphony Orchestra

Admittedly, my life as a music fan had leaned towards the classic rock genre. The closest I had been to a concert venue was years before when I went to a Halloween late night silent movie horror show dressed as a shabby prostitute. Now...

When I began to seriously date and live with Liz (now my wife), she expanded my horizons since she was a fan of all sorts of music including the classic and or orchestral scene. It turned out, she wanted someone to go with to see the Cincinnati orchestra's holiday concert. Without thinking of all the ramifications, I quickly agreed to go with her. 

The ramifications I am talking about were back in those days, I was still very much a novice as a public transgender woman. Plus I didn't have anything to wear to an event which ranged from semi-formal to formal. To find something to wear on a very limited budget, I set out on the improbable task of finding an outfit in a thrift store. Amazingly, I did find a black, very sparkly long dress which I could wear with a fringed shawl and for better or for worse I was ready to go. I finished off my black formal look with black tights and comfortable black flats for walking. Once my outfit had been decided, the toughest part was yet to come. 

Getting there was a different story. As I remember, public transportation was available for us to come close to the Music Hall where the performance was to take place. As always my limited mobility issues were a problem as we needed to arrive as close as possible. Plus, by using public transportation we could save money also as Cincinnati has a street car which runs close to the front of Music Hall but it didn't run late enough to help us in the return journey. What we did was decide to do was hail a taxi cab to take us to our next stop. Once we had the logistics of arriving and departing the concert, I needed to concentrate on the paranoia I was feeling about facing the public as a transgender woman in a totally foreign situation. 

Very soon, it was time to attempt to put my fears behind me and enjoy myself. Regardless of my fears, I think most of the public at the concert were in their own worlds and not mine. When that realization sat in, I was able to be impressed by the musical concert. It certainly was not all about me. 

The next stop for our evening was going to be a bit more difficult. First, we had to negotiate a crowd of people attempting to hail a cab. Our second stop or venue was approximately ten or more blocks away and was a place we had been to before so I felt comfortable ahead of time. We had a great time again and all to soon it was time for the trip home. Since we did not want to drink and drive, we ended up taking an Uber ride home. 

After the concert experience I had, I considered it one of the most defining experiences of my novice transgender life. I learned I could put my fears behind me and live a life I had always dreamed of. Overall, I had a great time and experienced a night I will never forget and for the year put me in a first- class holiday state of mind.

Supporting Cast

I'm on left with Nikki and Kim
on right.

There was no way I could have pursued my male to female gender transition as quickly and as thoroughly as I did without help from my women friends. 

Having said that, it is important to note I had already made it to the point in my transition when I could present rather well as a woman in public. In other words, I had paid my dues learning to dress to blend with other women in the venues I frequented. When I went to upscale malls, I went with my nicest professional business woman attire and then I would wear my jeans, boots and sweaters going to my sports bars or lesbian bars. To me at the time, the entire process was great fun and presented me with yet another facet of being feminine. 

After I had learned from all of my mistakes (or most of them), I was able to learn so much more about going even further towards my dream goal of living as a full time transgender woman. By pure chance I ran into two other women in the sports bars I was frequenting and we became fast friends. One of the main things I learned was I didn't need a man to validate my existence as a transgender woman because my two friends just happened to be lesbians.  Along the way, we drank a lot of beer, cheered on our favorite sports teams and had a great time. I think the evening I remember the most was when I was asked to be Nikki's wing person when she was trying to get a conversation started with another woman she admired. I agreed to try If you are wondering, I failed at my attempt to set Nikki up for success. It turned out to be my only attempt ever to act as a wing person at a lesbian mixer. All of that happened back in 2015.

Of course too, there was Liz who I met on a on-line dating site under "woman seeking woman" categories. She too identified as a lesbian, so I had quite a bit of experience on some of her thought patterns involving men. With her, my supporting cast just became stronger. At the time, I was in the last stages of still attempting to maintain some sense of having a male life. Very quickly, we formed a bond which included a first date to a drag show and a New Years Eve date when I first started my hormone replacement therapy medication. At the time, she very much sealed the deal on me transitioning further. I knew I was on the right path. 

I kept on putting off going full-time as a transgender woman long enough until Liz finally told me she didn't see any male in me at all and why didn't I leave him behind. I did and started a ten year relationship which culminated just over a year ago with us getting married. Throughout the years, she has been my supporting cast.

Plus I can't forget my daughter's input on my life. She has accepted me from day one. Even to the point of giving me my first hair styling appointment to her salon for my birthday. Which is a post for another time. 

To all of my supporting cast, I love you all.

Burning Bridges

 

Image from Marcus 
Clemens on UnSplash

Yesterday as I sat waiting for my wife Liz at one of her doctors appointments, I had a chance to pause and reflect back on my long and often difficult transgender journey. 

First of all I marveled on how I was accepted as me. Not necessarily as a woman or a man but as just me. The whole process to arrive took me over fifty years of my life to get here. A place where I could feel secure and relax with just being my authentic self. Then I started to think of how many bridges I torched to get here.

My main problem was my old entrenched male self. Even though he never wanted to be a part of my life at all, once he did, he never wanted to give up what he earned. So he fought completely to maintain his edge. He had an edge in what I like to call the "three F's" or family, friends and finances. He had built all three and was able to maintain a great job to support his other interests. In the meantime my feminine self was doing all she could to break out of the confines of the closet she was in.  She went as far as starting small and large gender fires designed to sabotage his very existence. 

The biggest bridge she tried to burn was the financial one. What happened was I began to stop at venues close to and even part of the places I was working at during the same period of time. My thought pattern was, they wouldn't recognize my feminine self as my male self. I was wrong and they did. Leading me to all kinds of potential embarrassments if anyone told my wife they saw me. The prime example of it almost happening one night was when the disc jockey (who also worked for me as a cook) played "Dude Looks Like a Lady" immediately after I showed up. Fortunately, my wife didn't notice anything but I most certainly did. I knew then, the world knew I was a cross dresser. 

Deep down, I thought if my deepest secret was discovered I would be relieved and I would have the chance to live the transgender life I had always dreamed of. Sadly I still had too much to lose such as the first two "F's" or family and friends. It wasn't until much later, when my friends and family started to pass away and I reached an age when I could retire on Social Security did I finally see a path forward to leading a transgender life. 

What a relief it was yesterday to know I had reached a point in my life when I didn't have to be so self destructive.  No more severe mental illness or thoughts of self harm. I could sit and be reassured I wouldn't have to burn any bridges anymore. 

Success equals More Success

Image from the Jessie Hart
Archive 

In an extension of yesterdays' post which mostly concerned  the success I experienced  when I began doing a portion of the grocery shopping cross dressed as my feminine self, I decided to go further.

If you were wondering, I chose grocery shopping to sooth my guilty conscious because I was sneaking out behind my wife's back while she was working and I needed to find a way to knock out two birds with one stone. Help her with the shopping and help me with my gender issues. It worked well and I needed more to do. When the Christmas holiday season rolled around every year, I found I could again put my new feminine cross dressing skills to the test by doing all my shopping as a woman. 

Since my wife and I were vintage antique buffs, going to several area antique malls became one of my favorite ways to find the perfect gift. Again I was able to multi task when I explained to her what I was doing in my spare time. Ironically, the malls were a perfect alternative to all the other clothing malls I was used to. The all important store mirrors I was used to were replaced by antique style vanity mirrors which I could catch a glimpse of myself to reassure me I was an attractive woman. Along the way, I was able to find the very special gift for my wife and sometimes even my brother. In the meantime, the malls never questioned my presence so I was free to browse on my own with no interference. 

I was so successful and the process felt so natural, I expanded my shopping into several upscale regular malls in the Columbus, Ohio area.  Of course, when I did, I needed to upscale my appearance to match the other women I would encounter. Much different than the antique malls I was going to. The whole process was fun and presented me with a whole different challenge. The places I was shopping at were upscale garden stores because my wife was a huge gardening enthusiast. Just like the mall experiences I had always had, it seemed no one cared about my gender, just my money so I challenged myself to do more. I always wanted to do more so I began to stop at different venues to grab a bite to eat. Interacting one on one with servers and/or bartenders helped me out of my gender shell I lived in. It worked and I was able to achieve more in my cross dressing life than I ever thought I could.

Even though I was successful in my shopping trips, I was still too shy to ask for help moving a large item I wanted to my truck or SUV. I found quite a bit about feminine privilege's when one night when I was dressed in my favorite black pant's suit, heels and blond wig. I then found an oak bookcase I wanted to give my wife but couldn't figure out how I would get it to my vehicle.  Problem solved when I gathered enough courage to go up to the check out counter and buy the piece of furniture, suddenly I was approached by two young men to move it. I was so relieved and flattered no one questioned why I couldn't move it myself. Once I got it home, in the garage, after I had changed out of my clothes, I slid it out of my vehicle and covered it up with old blankets. I made my wife swear she wouldn't look under the blankets and at Christmas she was overwhelmed with the gift which matched the oak roll top desk we bought together. 

From then on I was emboldened to do all my holiday shopping as my novice transgender woman self. I am certain my feminine side did such a better job doing the gift shopping, she deserved to do it all. Success equaled more trust and success.   

Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Going Back

Image of Liz on left and Daughter on right
from the Jessie Hart Archives.

 Recently I read a rather sad post from a person who was giving up her gender transition and going back to her original life. 

Even though I consider myself very fortunate in how my gender path turned out, I could understand the facts the person mentioned when it came to her new life. Among other things, the person related experiences which have haunted many of us following a transition. Such as having problems with loneliness, finances etc. So many transgender women are stuck in their houses, often with just having a computer to provide any contact with the outside world. This de-transitioner was older and provided a picture which showed a very presentable senior woman. My heart broke when I saw her image, I just can't imagine going back after putting so much work towards accomplishing a goal. Perhaps it is because I tried so hard and risked so much when I crossed the gender frontier. Plus, possibly for one of the few times in my life when I ever set specific goals, I was able to achieve what I set out to do. 

One of the major differences I saw when I read the post was how I approached the gender goals I was attempting to accomplish than most others. One of the examples was how I approached on-line dating services. I went all in with three or four services with the usual results of receiving tons of trash back in the process. I tried everything such as woman seeking woman to man seeking man. Amazingly, when I was giving up, some how I ended up meeting my current wife Liz who lived within driving distance in Cincinnati, a city I had always loved. That happened over ten years ago and it all started with a date to a drag show. As an aside, Liz identified as a lesbian witch so I was intrigued. 

In addition, the lucky move I made to create a new social life came when I decided to not go to anymore male gay venues and decided to go to the sports orientated big venues I was used to. I figured if I was going to risk being discriminated against, I might as well go to a place where I could enjoy myself. The gay bars aggravated me because I was always treated as a drag queen. What I don't recommend is the amount of alcohol I consumed along the way. On the other hand, I ended up meeting several other women in the venues who became friends. 

Very quickly, going back in my transition never had to be an option. By the time I decided to go all the way as a transgender woman, I knew my daughter would support me as well as Liz and my small circle of friends. As I made the final slide down the gender slope my landing turned out to be very soft. Even still, my heart goes out to those who are considering going back. Perhaps the whole experience could be thought of an ultimate experience which failed. Or maybe, they just wanted their old male privilege's back. 

Then again reversing my life again would be unthinkable because I would be so unhappy. I am afraid the person who did decide to go back would never be happy on either side of the binary gender border.