Afraid to Try?

From the archives. Underground
Railroad House.
Ripley, Ohio.

During my male to female gender transition, there were so many times I was afraid, or should I say petrified to try new things.

Probably, first of all, I was afraid to cross dress in my home at all. Fearing my family would discover my deep dark secret and I would be punished. Even with all the threat hanging over my head, I decided somehow I needed to try to move forward in my femininization. When I did, I felt so natural and felt I was doing the right thing. Regardless of my deep seated fear. 

Anyway you cut it, my fears cost me time and effort in my life. Precisely, all the time I spent attempting to work around other members of my family so it could be my turn to cross dress in the mirror. The amount of time I spent thinking and dreaming of being a girl was ridiculous. Finally the pressure built so much, I had to put my fears aside and dress as a girl. Even to the point of shaving my legs. In the long term, I became better and better in hiding my wardrobe and makeup away from my Mom, Dad and brother. To this day, I do not know how I escaped detection. 

The older I became, the more proficient I became at the art of wardrobe and makeup with what I could accomplish on my very limited income. My presentation as a girl became a very real possibility but not a possibility which calmed any of my major fears. In fact, some of them were even worse. Such as how was I going to be able to live a successful life as a man when I wanted to be a woman. Plus, what was I going to do about the looming chance I would be drafted into the military and sent away to Vietnam and what would I do if I couldn't cut it in college and flunked out. I spent many sleepless nights worrying about those things and more.

More to me happened when I was in college and I started to work my way into being a novice transgender woman. In those days, presentation or appearance was always the main issue since the only time I was really out was Halloween parties. Only being out once a year put a tremendous strain on me until I couldn't take it any longer and began to sneak out of the house dressed as a woman. Initially at night in lonely places before I knew the threat of doing things like that and jeopardizing my personal security. In the meantime, I still remember vividly the first time at night when I caught my reflection in a nearby store window when I was seriously thinking about going into a nearby book/magazine store and shop for a book.  I did not because my fears got the best of me and I was overwhelmed. 

It wasn't until much later when I was able to conquer those fears and come out into the world as a transgender woman but it wasn't without complete panic attacks on occasion. The one I remember the most was when I was thinking of making the jump from serious cross dresser to transgender woman in the parking lot of an upscale sports bar/restaurant I had been to many times as a man. I must have sat in my car for a half hour looking at myself in the mirror trying to gather the courage to go in. I don't know now how I did but I somehow put my fears behind me and went in. By doing so, my life changed forever for the best. I thought.

What really happened was, I set off a new round of fears because my male self (as well as my second wife) were digging in against me becoming anymore of a trans woman than I already was. While I was sure HRT or gender affirming hormones was my next step, my naysayers were against me. All of the process added to my fears of ever transitioning full time which increasingly my mental health was telling me was the only way to proceed. 

All of my new fears even took a back seat to my new everyday life as a transgender woman. At this time, the world was so new and different as I was learning so much as I built a new life. I hated for the old embedded fears to hold me back but they did. No matter how far I had come, the farther I had to go. Major issues such as finances, family, relationships and even sexuality had to be decided before I could move one.

 Fortunately, I put my fears behind me and conquered each of  my major conflicts as they arose. Victories equaled more confidence to achieve the transgender life I had always dreamed of. When I looked back, most of my fears seemed to be so petty. They certainly weren't at the time and became major mileposts on my gender journey.

Being Afraid to Try

 

Image from Jas Min on UnSplash

Since it took me nearly a half a century to fully leave my dark lonely gender closet, I have to assume there was an extraordinary amount of fear which was holding me back.

As life progressed for me and I became more and more entrenched in a male lifestyle I never really wanted, it was harder and harder to let go. I had a family and spouse who I loved plus a job I was progressing in. So it was not an easy decision to give it all up. 

It all finally came down to what my wife told me after one of our gender based arguments. She told me why didn't I man up and become a woman if I was so enamored with the idea. Had I followed her advice, I would have saved both of us so much turmoil over the years to come. By now, you know the story. I was stubborn and tried to live with one foot in the male gender world while at the same time learning if indeed I could live as a transgender woman. 

Through it all, even since I was taking small steps in my gender journey, the fear of not being able to make it as a full time transgender woman kept creeping back into my life. My scope became so much larger than just admiring myself cross dressed in a mirror to attempting to try the world in costume as a woman during Halloween parties. What kept me going was I felt so natural as my feminine self and then wanted to experience more and more. 

I write extensively about my experiences as a novice transgender woman. Even if I was petrified to try new experiences in the world, I pushed myself to still do them as my age was catching up to me. I wasn't getting any younger and all of a sudden, family and close friends around me began to pass away. Making my mortality even more of a reality than my gender dysphoria. Finally, when I reached the age of sixty and was exploring my life increasingly as a trans woman, it was time to act and put my fears behind me. Realistically, I knew I wasn't going to have a better chance to transition so I better do it. Setting all my fears aside and living in a feminine world turned out to be the best move I could make. I lifted a ton of weight from my shoulders when for the most part, my life restarted again. It was around this time when my new gender affirming hormones (HRT) were starting to change and control my body. Along with developing breasts and softening skin, my whole world softened and I felt emotions I never knew I had.

Now, I am so glad I wasn't afraid to try. My only disappointment is I waited so long to do it. Fear finally turned out to be a powerful motivator for me as it turned potential panicked situations into  successes. Rest rooms were a prime example of success or failure. 

This blog itself is another example. Way back when I was given the idea to write about my new experiences in this world, I didn't even know what a blog even was. Now with well over seven thousand posts and four million hits, it is time to stop and thank all of you for taking your time to stop by Cyrsti's Condo to visit. I have always embraced and enjoyed your participation and all I can say is I am humbled and flattered. 

 

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.

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.  

The Fear Factor

Fear Image from Alexandra Gorn
on UnSplash

No matter how you identify in the transgender community (or beyond into the LGBTQ world) fear on occasion dictates what you are able to do when you go out in the world.

I'm referring to the all encompassing terrifying paralysis you feel when you think you have been able to dress your prettiest and put on your best makeup to go out the door as a novice transgender woman or transvestite / cross dresser. I mention the different labels because they matter to so many in the community.

Of course, in my case, fear of discovery was always a part of who I was. What if the small world as I knew it discovered my deep dark secret of wanting to be feminine. What if my parents found out I rather have the baby doll on Christmas rather than the BB Gun I was gifted? I knew my life would immediately change for the worst and most certainly I would lose my small circle of friends. I felt my overall paranoia was well deserved.

Through all the fear, I managed to keep moving forward. I slowly learned how to dress myself in my chosen gender and became relatively proficient at putting makeup on. During that time I was lucky in that I only had to answer to the mirror. There was no one else. I am sure if my Mom had ever caught me she would not have taken the time to help me be more convincing as a girl. I would have been in for appointments to therapists who back in those days had no idea of how to deal with a transgender client. Many still don't.

Fear was my first and only companion for years as I came out into the world. I can remember how scared I was when I decided to leave the gay venues I was going to and try to make it in the real world of straight places. I don't know now how I did make it but I did. Slowly but surely I was able to use my fear as a motivator and it became one of my best accessories. I think now it pushed me on to be better and improve so I could convince the world I belonged. To this day, memories of past rejections keeps me on my transgender game. Even though I don't put all of the time and effort into my appearance that I used to, I still have the motivation to look better than the average cis-woman who for the most part does nothing when she goes out in the public's eye. I am fortunate in that I have been able to undertake hormone replacement therapy and it has provided me the feminine basics to get by. Such as my own hair, breasts, hips and softer/smoother skin.  

Since anxiety of all kinds has had a tendency to rule my life from many different angles other than just being transgender, I have been able to develop my own set of coping skills to survive. For instance, now I have learned not to be shy in public and be proud of who I am.  It helps to combat the basic fear I have always had of strangers as I was always naturally shy around people I didn't know. I remember a class I needed to take in high school where I was required to be up front at a podium and give a prepared speech. Yes I was scared but I made it through it and the entire process taught me a valuable lesson that I could make it if I tried. Sort of how I was afraid somehow I wouldn't make it through Army basic training so I tried harder and made it. Lessons learned which I used when I began to go out in public as a woman scared to death. If I could only make it the first time, I could make it forever. 

Of course forever turned out to be an elusive term because it took me many more tries to fail before I was successful in my overall presentation as a transgender woman.

After I developed my coping skills and gathered my courage, the fear factor turned out to be beneficial for me.