Taking the Gamble

Photo Courtesy
Jessie Hart

 I have never been good at or desired to be good at any form of gambling. However taking a gamble was completely the case when I decided to play my gender cards and transition into a transgender woman. 

Since it took me nearly a half a century of being a very serious cross dresser, I had plenty of time to consider my next move before I made it. Over the past, I have given more than a few examples of my many failures attempting to break out of my gender closet, as well as successes also. One of my examples of success was the night I was by myself in Columbus, Ohio attending a party at a transgender friends house. For whatever unknown (now) reason, I decided to go all in black. I wore a pair of shorts which were not short with black tights, flats and a black sweater. A dark wig completed my outfit. I looked at myself in the mirror and decided my looks were attractive enough without going overboard and out the door I went.

Once I arrived at the party, I found everyone on the patio because it still was a warmish fall evening and found I had dressed appropriately for the evening. After awhile, a single woman approached me who I presumed to be a lesbian. Our conversation moved along smoothly until we decided to leave for awhile and go to a well known large lesbian venue in the nearby downtown area. I gambled and said yes since I knew my way around Columbus and could return if I needed to. Later on in the evening, we went on our separate ways and I never saw her at any other parties.

Another time I gambled in the opposite direction and didn't go/stay with a guy in a bar in Cleveland, It happened after I submitted myself to a professional makeover and couldn't believe the change, It was so dramatic I was invited to tag along with the transvestite groups "A-Listers" or the self perceived prettiest cross dressers. They were shocked when a man approached me to stay and play pin ball with him. I was flattered but told him no because I didn't know if he knew the gender truth about me and if something negative happened, I didn't know the way back to the hotel where we were staying. I left forever wondering what would have happened if I gambled and stayed. 

Overall, the biggest gamble I ever took was when I came out as a transvestite to a few close friends in the army. This was way back before the so called more liberal LGBTQ "Don't ask Don't tell" days in the military. I worked in a very public job as a radio disc jockey position in Stuttgart, Germany. I could have lost it as well as being dishonorably discharged if the wrong people found out. Which they never did. I went on to marry one of the friends I came out to and she is the mother of my beloved supportive daughter. My gamble really paid off.

These are just a few of the gambles I took in my life. I do believe if you don't take some gambles you won't get ahead in your life. Plus just living pushes you into taking gambles. Regardless, I always tried to play my cards the best way I could. 

Pushing too Hard

Jean Skirt Look
Back in the day

Over the many years I spent trying to find my way into a feminine world, often I was guilty of pushing too hard. A primary example was when for once I was able to put my cross dressing act all together. In other words I was able to walk without falling in sidewalk cracks plus I felt my makeup, outfit and hair all looked as good as possible. I felt good and the whole experience was a positive one. 

The next time I went out I thought I would build on the last experience but didn't quite do it. In those days I was still validating my life as a cross dresser or transvestite by what men thought of me. It wasn't until much later when I learned it was so much more important to me to be judged and validated by other women around me. So, to make a long story short, I went overboard in my dress, makeup and especially hair. The end result was similar to a matador waving a red cape at a bull. I stood out like a sore thumb wherever I went. In addition, many times I was thrown back to square one and had to start all over with how I dressed myself. 

It took awhile of tough loving my feminine self but I finally learned all my trashy outfits and crazy wigs weren't working, I finally settled into a more or less everyday persona of who I would eventually become on an everyday basis. I substituted too short and tight mini skirts for more proper yet flattering jean skirts and I used flowing fun blouses/tops to help disguise my all too hated male figure. In essence I ended up killing two birds with one stone. My appearance was still on the cutting edge of having fun without going so far I was attracting unwanted attention.

Also around that time was when I quit pushing so hard and began to relax on most fronts. Now I could pay more attention in rounding out more of my total self. The way I moved, the way I talked began to come together, From then on pushing harder was out and a new confidence was in. I even settled on the same wig which I nearly wore out. 

Through it all though I don't want to give the idea that anything was a pushover when it came to my gender transition. It was just like I could start on starting on settling more of the more mundane problems I was experiencing. One of which was not so mundane was using the women's restroom which is a topic I revisit fairly often in my posts. It is no secret I like to drink beer and beer doesn't stay with you long so I had to use the women's room frequently. Often it was the ultimate answer to how I was presenting as a transgender woman. I found in many venues other patrons would draw the line and complain if I needed to pee. Having the cops called on me was a decidedly unpleasant experience

Another small thing I did to try to normalize being a single woman in a hetero bar was to use my cell phone as a prop. I would sit down, order and act like I was texting someone else to join me. As you can tell I was trying every little thing I could to make it in feminine world and earn my right to play in the girl's sandbox.

When I quit pushing so hard, the easier it became. 
      

Girls Night Out

Girls Night Out #1 
I am on the left.

As I was first attempting to survive in the feminine world without the "Ha-Ha" moments Connie mentioned in a recent comment on my :Ah-Ha" post, I craved any opportunity I had to join a women's night out. In a relatively short period of time I was fortunate and was invited to four, One of which was even a bachelorette party which sadly was cancelled. Two of the remaining invites were with a group of cis women friends I became close to until similar to many women they got married and moved away from the group. Children were involved also.

Perhaps the most exciting was my first invite because I had no idea of what to expect seeing as how there were going to be a couple other women attending who I didn't know. How would they accept a transgender woman? The answer was one didn't seem to care and the other rejected me quickly.  

My first issue was what to wear of course. I wanted to appear as attractive as I could without over-dressing the other women. As you can see in the picture, I think I achieved the desired effect. My second issue was what would the conversation be when no men were present and again how would I fit in. The whole process (per norm) turned out to be just a whole lot of worry about nothing. Most of the conversation dealt with family and children so I just inserted my daughter's examples when I could. During the space of the evening I even forgot to worry about my voice. Everything must have worked out fine because shortly after the first night out, I was invited to another before I moved away with Liz to Cincinnati.

Perhaps the most surprising girl's night out occurred when I was invited by a group of servers from one of the venues I was going to on a regular basis to join them for a get together at another trendy venue. I was terrified when I said yes. How would I react to going with a group of younger, more attractive women to a venue I had only been to a couple of times. This time there wasn't much conversation because of the amount of guys the rest of the group attracted. It turned out to be like I was almost invisible as the night went on. Lesson learned.

As far as other lessons learned, I discovered no new earth shattering gender secrets when women gather.  Naturally, it was no big surprise when the younger women I was with got their flirt on with men and forgot about the group all together. Even though all of that happened I was pleased I survived the evening without doing anything gender ignorant.

Overall, all of the girls nights out I was invited to were fun and learning experiences. I was happy to accept the invitation. 

  

A-Ha Moments

Beaded Trans Hair Piece by
Liz T Designs 

 This is an extension of several recent posts I have written about  my gender transition but few of them were about a-ha moments along the way. I guess you could call them rare moments of gender euphoria before I ever thought of such a phrase which I of course didn't invent. 

The first a-ha moment I had was early in life when I realized dressing up as a girl wasn't enough. Being a girl was the best idea. There was no way I could know this was the first indication I was transgender and not a cross dresser. 

Fast forward several years of gender struggle, my next moments of gender euphoria could all be wrapped up in all the Halloween parties I went to. Through them all I learned the power of dressing as a woman was real and I loved it all. Especially the parties when I was mistaken for a well dressed woman not in costume. More on those parties when I spotlight Halloween in my October posts.

In essence Halloween taught me there was a chance I could pursue farther the idea of living my life in a feminine world and survive. 

Finally Halloween became just another day for me and I moved on to other a-ha moments came when I decided male dominated gay venues weren't working for me. I became quite frustrated when I was treated like a drag queen or when I was completely discriminated against for simply being myself. When I learned I could frequent large sports bars or the occasional small lesbian bar and be much happier.  Often I learned the hard way I could live in the world and play in the girls sandbox. The more I did it, the more I wanted to do to expand my knowledge of being an out transgender woman. Which in itself was a true revelation.

About this time a-ha moments came fast and furious as I learned the hard way how to exist and communicate with other women. For the second time in my life woman's fashion took a back seat to more important functions such as establishing myself as a brand new feminine person. All of the sudden I was completely immersed with communicating with the world as a transgender woman.

Perhaps the biggest a-ha moment in my transgender life came when I started hormone replacement therapy. For once I was syncing up the inner woman who I strongly felt needed to live with my external testosterone poisoned exterior self. In a short period of time, my breasts and hair grew wonderfully along with a softening of my skin and features. Perhaps most surprisingly were the changes to my emotions. I became decidedly less aggressive when dealing with world. I guess you could say HRT softened my world.

Of course there are many other a-ha moments which may come along in your life such as passing a mirror and noticing a woman looking back at you. Hopefully your positive moments out number your negative ones.  

Living the Dream

 

Photo Courtesy
Jessie Hart

For so many years I lived with what I thought was the impossible dream. That dream of course was wondering if I could ever live a life as a full time transgender woman. Although for the longest time I didn't see how I was ever going to make it to my goal, slowly but surely I kept moving towards it. 

I like to say I was a serious cross dresser for fifty years of my life. During the half century I made a few strides in makeup and fashion only to find myself headed back to the cross dressing drawing board time and time again. The only positive aspect of the experiences were I tried to learn from each one. What worked and what didn't. Every positive gave me hope for the future. 

Along the way I have written concerning the gender maze I found myself in. I felt everytime I achieved one goal and turned the corner, I found another corner to deal with. Almost all with no positive intervention from any other person. Even though my wives knew of my cross dressing activities, they were rarely participants. And, if the truth be known, many times I didn't want to follow the ideas of what a woman meant to them. Even to the point of trying my best to dress to blend when and if we ever went out together as girlfriends. Examples were when my second wife and I used to journey to Columbus, Ohio to eat at a LGBT friendly restaurant. It got the point of me wearing jeans and a sweater and she (my wife) still didn't like the way I looked. Deep down I knew I was struggling to find my feminine identity and I stayed on course with what I wanted to wear. 

Slowly but so uncertainly my small successes added up and my dream of living full time became more than a distant reality. After the fewer and fewer setbacks I had, I righted the gender ship and realized yet again how natural my feminine side felt. When I went out as a novice transgender woman I felt the world was in the right place and I even went as far as feeling out of place when I went out as a guy. 

Finally even I could not deny it any longer, I was meant to live as a transgender woman. I started hormone replacement therapy and started to transition my exterior as close as I could to match my feminine soul. It all worked so well and I was left no alternative to living my dream. The hormones fueled the fire which burnt my final bridge back to any male life I had left. 

After I made the commitment to giving away all of my male clothes, a new voice inside of me was asking what took so long. My only answer was I was stubborn and wanted to hang on to whatever white male privilege as long as I could. Most certainly giving it all up was one of the best decisions I ever made.

My biggest lesson from my lifetime of experience is, not trying at all is the biggest disaster.

Trans Dar?

Photo Courtesy Jessie Hart

 Trans Dar to me means recognizing another transgender woman. All of it seems so simple but it is not. 

First, you have to decide if your transgender instincts are correct. An example occurred when I was arriving I saw another woman who arrived just ahead of me for our recent transgender - cross dresser group dinner. She was well dressed in a summer dress with low high heels. More than likely, if I had just been coming to the venue on a regular night, I may have not given her a second glance. But she was by herself and she set off my Trans Dar. She beat me to the table and later I found she was a self professed cross dresser. 

Approaching another transgender person for me has never happened. Back when we used to shop regularly at a couple grocery stores I used to see on occasion a couple of women I perceived to be transgender. The most I did do was try to get a closer look to see if I could be correct if she was another transgender woman. On occasion I wished I had the courage to speak to them but I didn't. The main reason was I was afraid I could be wrong. How rude would it be for me to try to strike up a conversation with a stranger for no specific reason. 

Another reason for not approaching another transgender woman is many don't want to be read as trans and approached. Normally anymore I am in my own little world and would be really surprised if I was ever approached. Also I would have to examine what I was doing wrong with my presentation as a feminine person to blend in with the public. Which is something I didn't always do.'

I am sure when I went to many venues such as grocery stores or big box stores, I was the one who didn't blend in my tight short skirt with heels and hose. I was the one who went to a mall in a tennis outfit I put together. Which did get quite a bit of attention from the old men who were exercising in the mall. It all led to a heightened sense of Trans Dar whenever I saw an overdressed woman in a store where nearly all women dressed very casual.  

Whatever the case, Trans Dar is a difficult topic which does it part to keep our transgender community apart. I go back to the example of the cross dresser I met for the first time the other night. If it wasn't for the dinner, I would have never had the chance to meet her. 

To start with, we transgender tribe members are an exceedingly rare part of society and need all the companionship we can get. Sadly Trans Dar is not the way to do it. 

Count Your Change

Photo by The DK Photography 
on Unsplash 

 I vaguely remember the days when I used cash to purchase my needs. Those were the days I used to accumulate quite a bit of change. On the other hand, my wife was a bookkeeper and kept track of all of our finances. 

About that time was when I started to explore the world as a novice transgender or an experienced cross dresser and needed feminine clothes. Which was easier said than done. First I had to decide where to go for the best deals and better yet to try to figure out which size would fit me and flatter my masculine figure. 

Money was hard to come by as I attempted to put together a feminine wardrobe. Not only did I have to sneak out, I had to slowly accumulate the money to shop without my wife wondering where the cash was going. 

About that time is when I really discovered thrift stores. In the stores, I had the freedom to shop to my heart's content without anyone to bother me. I could also purchase clothes at bargain basement prices which I could experiment with. Fashion attempts could be kept at more of a minimum thanks to thrift store shopping. Also, once I learned what I could wear I could go to a more upscale clothing store and buy a similar fashion item. 

It was about this time when I learned the etiquette of using the changing rooms. Of course at the beginning I was very paranoid about even asking to try clothes on. As time went on, I hitched up my big girl panties and asked for access to the changing rooms. I am happy to say I never received any negative feedback about using the women's changing rooms. Nothing from the clerks I encountered and nothing from other women. I don't know what would happen today with the advent of "Karen's" or self entitled people who take it upon themselves to police others. Plus, today I always have Liz with me to "clear the way" for any potential negative circumstances.

My fashion life has become so much easier now that my male past is behind me and I don't have to worry about maintaining two wardrobes. I have only my full time feminine clothes to worry about. And currently my biggest problem is rediscovering all my fall clothes. Most of which still fit since my size hasn't changed that much. Along with my eyes which I had recently checked. I still have the beginnings of a cataract in one eye which doesn't require surgery yet. So new glasses will soon be my new fashion update. 

Even though I use my bank card for almost everything I buy, I don't have to count my change anymore to buy my clothes. Plus one thing I forgot to mention was on line shopping . Liz is a huge fan but I am not so much. Having to return something because it is the wrong size is such a hassle. I still appreciate going to a store and shopping. 

Time in a Bottle

 

Photo Courtesy Nickolas Horn
on UnSplash

With all due respects to Jim Croce who wrote the song "Time in a Bottle", I decided to title this post by the same name.

The bottle I am referring to is the alcoholic one. I grew up in a home where my Dad used alcohol regularly so it wasn't much of a surprise when I became of age I started to drink alcohol also. Along the way, I developed the habit of being able to hold my liquor well. If my friends and I could somehow get around the age limits to buy it. As with any other potential vices, we found ways to do it. 

By the time I got to college I was well versed in drinking with everyone else. Even if I was still underage due to Ohio's liquor laws. I guess you could say I was ahead of the curve when it came to alcohol.

Then came the military. Of course my time in basic training took me away from any drinking activities as did my time in Thailand. Due to the lack of drinkable beer. But then came the exact opposite when I was sent to Germany who really take pride in their quality beer and wines. Very quickly I acquired a taste for our locally produced beer and a few wines.

Fast forward to what any of this had to do with being transgender. As most of you probably know, alcohol often brings out the best or the worst in a person. People often become braver in many areas of their lives. Ultimately liquor enabled me the courage to first come out as a transvestite to my friends after a Halloween party. Which could have gotten me into any number of problems in the pre "Don't ask-Don't tell" era of the military. Here I was coming out in plain view to a few of my friends and risking a less than honorable discharge. All because of alcoholic infused bravery.

All of this turned out to be just the beginning. I tried to come out to my Mom after a night of drinking and was soundly rejected. But I kept trying. 

When I first started to try out the world as a feminine person, the bottle proved to play a major role in the process. When I gathered the courage to stop for lunch, I would always order a beer to steady my nerves and later give me the courage to try out new and exciting venues. Of course the further I went, the further I wanted to go. 

As I went further and further into the feminine world, I chose large sports venues and small lesbian bars as my favorite places to go. It was very difficult for me to conquer the fear of rejection I was feeling and my use of alcohol helped me. Even though it was only beer I was drinking, I was emboldened to continue. After a period of time, it was difficult for me to separate my desire to become a transgender woman with my desire to drink.

Finally I came to the point I didn't need it. About that time I had a scare concerning my liver so anymore recreational drinking was over. Without hesitation, my time in a bottle was over. Plus, I didn't need to find the courage to live the way I had always dreamed of, as a woman. I had arrived and now my alcoholic consumption is approximately two beers a month.  

From the Gender Ledge

 

Photo Courtesy
Jessie Hart

In many ways, this is an extension of yesterday's post. Along the way I mentioned and showed a photo of a guy looking over a steep ledge. My comment was I was at the ledge looking over the edge when I was considering moving away from my old cross dressing male life and moving to a full time existence as a transgender woman. 

Naturally, I was terrified of leaving behind a fairly successful life as a man with a good job, friends and family. I had to prepare myself to lose almost everything I had worked so long for. I had reached the magical moment when white males become privileged citizens by default. On the other hand, I was near retirement age so wouldn't have to worry about finding a new job as a transgender woman. On another hand, sadly, almost all of my close friends had passed away and my parents had long since passed on. All of a sudden the ledge didn't look so steep.

Still remaining were the normal everyday hurdles we face in life. I had to consider even the smallest details of life. For example, I would have to go into male dominated spaces as a transgender woman. Another aspect was how would I present myself to the world everyday. No longer would I have to stress compulsively on how I looked. Thanks to hormone replacement therapy, my whole make up routine was shortened to a point when I only needed a light application of eye make up and lipstick if and only if I was going out. I was always fortunate in that my hair grew on it's own to a point where I didn't have to wear wigs.

I won't sit here and try to tell you jumping off the ledge was easy. Often the landing was bumpy and uneven. The only words of wisdom I would have are to try to stay loose and flexible. Always assume new changes are right around the corner. Just when you thought you had everything figured out. Like when I went with Liz to get my ears pierced. She got her smile on when I protested slightly when the pain hit. For all of you considering piercing your ears don't think it is painful because it is not. I am just a huge baby when it comes to any kind of pain. 

I can't say enough how important it was to me to have formed a strong support group around me when I decided to jump off the ledge. I can't thank them enough. I was able to find them by taking the steps to put myself out in the public's eye. On the other hand, all of them were open minded enough to embrace me as a friend and as a transgender woman. They made my gender landing much softer.