Putting Yourself Out There as a Trans Girl

 

Image from Sasun Bughdarian
on UnSplash.

Putting myself out there in public was probably the hardest thing I ever have done in my life.

Most of the time I was in a high-risk-high reward situation as I tried and failed miserably at presenting myself in public as a novice transgender woman. I kept on working until I put myself into the low risk-high reward category when I finally was able to pass reasonably in the world I discovered was run by ciswomen if I ever wanted to succeed. I was so far away from the world of cross-dressing/transgender parties and socials I kept going to, I was learning so much more every time I did it. I was on thin ice on my gender path and I knew it. I just hoped the ice would hold my weight. Even though I was on a crash diet to be able to purchase more fashionable clothes and look better. It was questionable. 

All along, I knew there was no way I could go halfway and make it to my dream of living fulltime as a transfeminine person. Trying to live a life stuck between two genders was no way for a person to live and when I did, the gap between the two genders was too much to overcome. My mental health suffered and I was very self-destructive and had to do something about it. The last thing I wanted to happen was that my gender dysphoria would doom my life as I knew it.

In the meantime, I did the only thing I knew how to do which was continuing to hide my cross-dressing from the world behind a wall of male macho intentions. Again, it was so hard to hide my truth that much later in life I was surprised that no one had guessed my dirty little secret when I finally cracked my gender egg and made it out of my closet for good. Another problem happened as I had to keep building a successful male life, I never wanted, I knew some day soon I would have to tear it all down and start all over again. Internalizing and putting that day off, just hurt me more as I continued to put myself out in the public’s eye.

By doing so, my risk situations leveled out to a point where they almost balanced each other. I was in the ultimate high-risk situation of losing essentially my whole life but at the same time conquering the higher risk of being able to carve out a new and exciting feminine life from scratch. It seemed to me that every corner I went around on my new path had different obstacles to take on as I was intimidated by the complexities of the ciswoman’s world I so badly wanted to live in. As I left the male world I wanted nothing to do with, it seemed nothing was easy to do as I had to learn everything I could quickly if I ever wanted to survive. The worst part of it was, I wanted just to keep running back to the privilege of the male life I had given up but just could not.

So, I kept putting myself out there to make a lot of bad mistakes on the way to my own form of womanhood. Like ruining hours of prep time getting ready to go out, only to discover I was moving like a linebacker in drag when I did it. Or the time when I had everything down when I went out and promptly got my heel stuck in a sidewalk crack and almost fell down. I made it to the point of being so paranoid about going out, I kept on wondering if I would ever be able to put my feminine self in motion for the world. Even though it was difficult to do, I kept forcing myself back out and getting better in my overall presentation. Making it less of a high risk that I could do it. Since I had already been laughed out of venues in the past, what was the worst that could happen to me.

Ironically, my path took me another direction right into the worse than could happen experience when I was almost molested by two men when I was alone on a dark city street and I was lucky to get out of it by giving them my last five dollar bill. It was too close for comfort for me, and I almost learned the hard way what ciswomen are raised to know about the dangers of toxic men. I started to always plan to ask for a transgender man friend to walk me to my car after that. I know I mention that experience a lot but it is my way of always warning you that when you go behind the gender curtain and transition, you lose your male privilege of personal security so be careful when you go out because it is certainly a different world for a trans woman.

For years, I kind of just drifted along in the female world learning what I could to increase my knowledge until I learned too much and found I could never go back to the male life I had before. Almost all the risk on not doing it suddenly became extremely shallow to me as the why’s I should not transition started to fade. I had put so much time and effort into my womanhood, what I was waiting for.

I had even survived the worst moments of my male life when almost everyone around me passed away, leaving me tragically lonely and sad. The only bright light I had to fall back on was the knowledge that my strong feminine self was always there for me and it would be extremely low risk to reach out and ask for her help. Even to the point of helping me find a new social circle to hang out with.

I stepped out of my dark closet again and was fortunate to find a small circle of diverse friends I could socialize with and even grow into my new HRT hormonal changes with. I stepped out of my social box and utilized the so-called straight venues I was already a regular in, along with a transgender woman friend of mine and against all odds found new friends who all happened to be lesbians. From there, I even took the risk of going online to the trashy dating sites and tried my hand at attracting someone else. At that point, what did I have to lose. After a very low-risk, high gain deal, my future wife of over fourteen years contacted me. We clicked and have been together ever since, so I am still enjoying the results of my low risk move. But I must stress, none of that success would have been possible without my determination to put myself out there and try.

Certainly, I failed quite a bit, but from failure came learning and I made it thank goodness.

As always! Thanks for reading along and all of your comments are welcome.

 

 

A Destination or a Retreat into Trans Womanhood

Image from Brian Wangenheim
on UnSplash. 

As a youth, all I did when I failed at a male task was to seek the reassuring feelings of my feminine clothes and makeup. I knew then I would not have the male world I hated for a while.

The pattern continued with me into adulthood and was even expanded to include a better sense of wardrobe and makeup as I ventured into the world. But then it started to slowly reverse as I started to blend in with the ciswomen around me. Increasingly, I was feeling better about the progress I was making as a serious cross-dresser and wanted to do more as I moved towards being a transgender woman in my mind. Even though I was still extremely lonely as my feminine self, I was starting to embrace the unique person that I was. Afterall, how many people get to experience both sides of the primary genders in their lives.

On occasion, I even reverted to appreciating all the male privileges I had learned after a particularly brutal day of exploring the world of cross-dressing. Early on there were many I needed to go through as I continued to pay my dues to get to my dream of possibly living my life as a transfeminine person. Not a man.

Even though mixing genders was beginning to have a bit of normalcy for me, I came to the point where I would not recommend the journey to just anyone who was not totally committed to it. My mental health, which was already frail at the time, did not take easily to the journey ahead and it suffered. Again, sending me back to the comparative safety of the only other life I had learned to live successfully when I was competing as a man in the world.  At that point, it was difficult to tell if I was on a trans destination or a male retreat. The only thing that kept me going down my path was the deep sense of satisfaction or gender euphoria I felt when everything was going better when I interacted with the world as my true authentic self. Free and out of the closet for a change.

It took me years of experimentation in public, as I set up my own personal bucket list of what I perceived to be the real-world ciswomen had to face in their lives. I figured out why I would want to go there if I could not make it. In other words, I kept challenging my feminine self to do more and more such as do more than just spend very little time in public just walking around or shopping in easy venues such as women’s clothing stores where your money overcomes any reaction to your possible gender when it came to testing myself. I certainly then was setting myself up for a possible transgender destination in my life as I worked my way through my bucket list.

As with anything else in life, all I had learned about being in the world was not all positive and I found myself deeper into my quest to cross the gender border and complete my male to female femininization project. I learned the hard way to try to not get myself into questionable safety situations that women know not to get into that do not bother men. It seemed the gender universe was testing me on certain nights such as the one I needed to fend off negative advances from a much bigger cross-dresser admirer at a party I was at with the help of my second wife. Something I never bargained for as I went around a blind corner on my gender path. It was easier to think about erasing all my male privileges such as safety but harder to learn what to replace them with.

I do not think I ever did replace my new lack of intelligence with the cismen I interacted with as I was mansplained more times than I cared to remember by men of questionable intellect. Such as the tow truck driver I was forced into a conversation with one night when he was towing my car home. I had to sit there, and act interested when he had to tell me all the workings of his truck. Like I cared when all I wanted was to get home safe and sound. Which I did. All the bucket lists in the world did not prepare me for the reality of living a feminine life, but even still, I was loving everything I learned behind the gender curtain. If I was ever a girl scout, I would earn merit badges like what to do if your car breaks down when you are by yourself and the first person who stops to help is a sheriff. Who would not listen to me when I was trying to explain to him and the tow driver the easiest way to my house. I finally just gave up.

It soon was becoming obvious to me that I was no longer retreating behind my dresses and makeup to cover any vestiges of a male life I wanted to cover up. Instead, my full-fledged female life was a complete destination. A destination I wanted to do more than anything I ever had done in my life. There would be no more retreating back to my male world. No matter how easy it would have been to do it because he had always kept a comfortable home for me if I ever wanted to return. Much to his disappointment, I continued my feminine destination into the world of HRT gender affirming hormones which separated me farther from ever hiding again in my old unwanted male world.

HRT was certainly the end for any thoughts of ever returning to my old male self because I felt to increasingly natural when I took them. It was as if my body was telling me what took so long as my external self-synced up with the woman, I always saw myself to be. It just took me years to get there. Which was the tragic result of me not listening to myself.

Thanks for reading along on a few of my trials and tribulations of my gender journey. I hope yours is much smoother. Any comments are always appreciated.

 

 

How Halloween Benefitted Me

 

Image from Jennifer Marquez
on UnSplash. 

In the recent past, I have written a couple of stories about my Halloween experiences but there were more which taught me valuable lessons about the possibility of following my gender path.

Such as the time I was able to set up a training trip down to my company’s headquarters in Lexington, Kentucky to coincide with my favorite time of the year which was Halloween. In those days, the fashion rage was very much into fake leather, and I could not wait to show off my new faux leather mini skirt and matching top at a Halloween party. To get ready for the trip from Ohio to Kentucky I needed to find private time away from my wife to pack two sets of clothes. One for my male presentation at the company headquarters and another for my so called “costume.” Somehow, I was able to find room in my suitcase for makeup and a wig, and I was ready to go. The lessons I learned on that trip were that I could indeed pack effectively for two genders.

Once I arrived in Lexington, the next problem I faced was figuring out where I was going to go to show off my new “costume” in public for the first time. Luckily, the hotel I was staying in had several different publications in the lobby I could look at to see if I could find any parties that may be close by. I did, and then had to try to find them, after I was cross-dressed and ready to go. I was nervous as I put on the only pair of black panty hose I brought with me and put on the padding I needed to work with to provide a feminine figure. Next came my makeup and a resurrection of my wig following its time in my suitcase put on my heels and I was nervous and ready to go.

Probably, the biggest challenge I was going to face was going from my room to the elevator then worrying about facing anyone else as I went down to the hotel lobby. I should not have worried because I did not see another person until I arrived at the entrance and the ones I did act like I was not even there. Then, I was off to find the venue I was looking for in a city I was not familiar with at all. Back in those days, there was not such an invention as a GPS to help me along but somehow, I did find the first big venue I was looking for. Lesson learned. Try to find out where you are going before you get there. On the other hand, I had a powerful motivation to get out of my closet and see if I could survive in a straight world of Halloween party goers as a novice trans woman.

When I arrived at the entrance to the venue, they were checking identification at the door and surprisingly, no one reacted to the person in costume as a woman with the obviously male I.D. My hand was stamped and in I went to an unknown experience which might change my life as all the other Halloween experiences had done.

As I walked in, the venue was already packed, and I needed to find my way to the bar for a drink and the closest route was across the dance floor. I took a chance and made my way through the couples dancing and up to the bar. Once I ordered my drink and was served, I started back to a relatively uncrowded part of the club to enjoy people watching along with the feel of my “costume.” It was then that I learned the lesson of what it was like to be a ciswoman in a crowded venue with potentially toxic cismen who could not keep their hands off of my rear. I have never been pinched and touched so much in my life as I made my way back to one of the rare open seats I could find. Lesson learned again as I headed off to another venue to experience more of my evening before it was time to return to my hotel in my faux leather outfit.

I did find one other place which was having a party, so I decided to make it a night by stopping in there also. The second venue on was far less crowded and mellow than the first one and I was relaxed and had the confidence from my first experience to go right in. I was met by a friendly checker at the entrance and again no reference was made to my male identification which was probably due to the magic of it being Halloween.

One thing I did not do was stick around in either place for their costume contest because I was so insecure about myself. I did wonder if I did join the contest and somehow won if all the men who were fondling me would have been properly shamed but probably not. All they pinched was foam rubber anyhow and I went on my way with another powerful lesson learned about how ciswomen are really treated. I wondered if I had not been wearing any protective padding would I have bruised the next day.

The biggest problem I had was coming down off of my gender euphoria rush to effectively teach the company management classes I was supposed to teach. I did not make the trip to Lexington very often and was never able to spend a Halloween evening there again. When I went, I was often stuck going out with groups of other male managers to strip clubs where I did not really want to go. While I admired good female bodies, I never had the urge to go any farther. I was always the first to leave the strip clubs which made for a clearer head in the morning from no alcoholic hangover.

Without the benefits of many Halloween experiences, I am sure eventually I would have made it to my goal of living a fulltime transfeminine life, but it would have taken me longer. I would have not had the “A-Ha” moments I had from Halloween when I was able to see why women are able to exist in the world the way they do, and I will never forget the lessons I learned from my favorite holiday.