Sink or Swim Time

Image from Jeremy Bishop
on UnSplash.

Coming off all my new and exciting Halloween adventures, it was time for me to decide if I was going into the deep end of my gender pool to see if I could sink or swim for my life.

One way or another, I knew I could not wait another full year to leave my closet and explore a feminine world which I had barely learned anything about. What I learned was that I loved the femininization process and wanted to know more. I loved the process of learning to apply makeup properly and the feel of the clothes, but even more the fact I was just a little closer to living my dream of how a ciswoman really lived. To accomplish it, I would have to keep swimming in my pool of life. Especially when I was in over my head.

I caught myself in the deep end too many times when I did not know what I was doing in the early days when I was struggling to blend in with the world and essentially disappear to most of it. In the shallow end of the pool, I discovered most strangers did not care about me anyhow as they went about their everyday lives. It was the deep end where I ran into problems. Since I always considered myself a quality student of the women around me, I quickly found how little I really knew about where I wanted to go as a novice transgender person.

It was not until I learned how complex a ciswoman’s life was as compared to a cisman’s did, I figure out how far I would need to swim to make it to my dream. To make it, I needed to become a long-distance gender swimmer while I stayed in the deep end. To stay where I wanted to be in the pool, I needed to fight back all the fears I had of stripping myself of the male life I had tried so hard to build up and start all over again. To make matters worse, I was highly insecure about if I could ever make it to my goal at all. You have probably heard the old saying that you must dream about something to do it and I was having a difficult time even dreaming about my own unique path to womanhood. At the time, and into the future I knew I could not afford any expensive gender surgeries so I would have to go the distance on my own out of sheer will power as a transwoman friend once told me.

The only things that kept me going were the deep sense of feeling natural when I was following up on my feminine instincts and an even deeper sense of gender euphoria any time I succeeded. Maybe I could make it after all and be more like my transgender woman friends I so admired at the diverse parties I was a regular at in nearby Columbus, Ohio. I figured they had made it in the deep end of the gender pool and so could I. Plus, every party I went to seemed to teach me more about the life I was expected to live as a trans woman without any gender realignment surgeries. Which separated me out from most all the other accomplished transgender women I met in Columbus.

From there, I left the gay venues I was relying upon for socialization and ventured into the straight bar scene I mention so much. It was all part of treading water in the deep end of the gender pool until I figured how I was going to make the next move. Either give up and go back or keep on swimming. Along the way, I became tired of all the effort I was putting into my new life as a transfeminine person until new energy came along to keep me going.

I cannot say I was not in danger of drowning if I did not vigorously keep swimming towards my dream goals in life. My already strained mental health was already causing me to be very self-destructive and a danger to myself, so I was in a bad place to be if I was in the deep end of the pool struggling to figure out my future. To make matters worse, nearly everyone I was close to in my life passed away within three years of each other leaving me in shock and nearly all alone. Somehow, I found the inner strength I needed to stay afloat until I was able to reach out to a whole new set of women friends who enjoyed my company. Above anything else, they saved me from drowning while at the same time teaching me the fine points of being a woman. I tried to thank them, but they never understood and we continued to have fun together.

Included in the group was my current wife Liz who met me in an online dating site against all odds when I was in a lesbian woman seeking woman group. It turned out we lived semi close together and were able to correspond online until our first date at a drag show. We have been together nearly fourteen years now and married for the majority, so I consider that a great success story which makes up for all the down times I suffered.

If you are considering a swim into the deep end of your gender pool, make sure that you are sure you want to give up everything you may have to not turn around and go back. It is never easy and each of us has their own particular path to follow and you need to claim your successes when you have them. Gender euphoria is often brief and fleeting for those of us who have not been blessed with many natural feminine characteristics. We just have to work harder to even stay in the pool and take everything we are given to stay afloat.

I have had several recent comments from readers who are in despair because they have nothing to work with as a novice transgender woman or cross dresser but do have several understanding ciswomen who accept them to fall back on. A great way to study the fact that all women are different and more than a few might be closer to you when it comes to shapes, sizes and personalities than you think.

As I always say, I hope you can find your own path on the way to your own personal gender freedom. Thanks for reading, and commenting!

 

 

  

I Did Not Just Wake Up This Way

 

Image from We Vibe Toys
on UnSplash

I get a sense of amusement (mixed in with a little frustration) when someone thinks I just woke up one day and decided to put on a dress and makeup.

I don’t have much energy to keep explaining how my gender dysphoria has always been a part of me and one I did not ask for. My frustration sets in when some time ago, an acquaintance from the transgender community I met proudly told me she had never been gender dysphoric in her life which I had a hard time believing since she finally went through the extensive gender realignment surgeries.

Then, I began to think did she or even me know the true definition of gender dysphoria. So, I went to look it up from a well-known online dictionary and here is what I came up with: “ a state of severe distress or unhappiness caused by feeling that one's gender identity does not match one's sex as registered at birth.”  I felt that my acquaintance simply did not know the meaning of the words.

Immediately it made sense to me because that is the way I felt growing up wondering if I was a boy or a girl. The only thing I knew for sure was the way I was born and how it affected my life. Perhaps the worst thing was that if I did not understand the way I was with my gender mix-up, how could I possibly expect anyone else to understand it either. So, I headed down the worst path ever and tried to internalize all of my feelings. Internalizing left me with only one way out. Which was to attempt to cross-dress myself in front of the mirror as a girl, away from my perceived dominant male gender.

As many of you know, cross-dressing in secret behind the back of your family is never easy as you have to sneak around and plan every spare moment to do it. It was something I would not have wished on my worst enemy. Why couldn’t I just have been a so-called normal boy like all if my friends seemed to be. Then reality set in as I realized again, I was not “normal” to many people and would have to live with it. Living with it became increasingly more complex as I matured as a serious cross-dresser into an even more serious transgender woman. I evolved into needing more than just admiring my feminine self in the mirror and wondered if I could do it in the world too. Before I did, I needed to gather the courage and confidence to do it. Which was very difficult for me to do because I just did not wake up and lose all the insecurities I had in my life. Many of which involved me ever being able to live as a woman, trans or not.

As I always mention, my early days in the world as a novice transfeminine person were not easy until I developed the tools in dressing myself and learning the basic makeup arts so I could blend in with the ciswomen around me. After many failures in the malls, I finally knew I had made it when the teen girls who used to notice and harass me began to leave me alone and concentrate on their own developing socializations into women. Which was the same path I was on. Just from a totally different direction, but it was taking me awhile to wake up and realize it.

One of the reasons was that my male life kept getting in my way. He needed space to continue to work on his marriage, help care for a daughter, and work on expanding to a growing successful career. Nothing too remarkable for most cismen, but very difficult for the average transgender woman trying to build her life at the same time. The worst-case scenario happened and the two binary genders within me began to compete for space at the same time. It was like the old days of waking up wondering what gender I was going to be any given day and the stress to my overall mental health was building more than I can say. I became very self-destructive as I finally thought I was not strong enough to handle the life I was given.

Somehow, day to day, I put my life together trying to remember who I was that day until I was fully able to try to disguise my true feminine self to the world. While, at the same time presenting myself as my “normal” male self. I ended up covering my feminine tracks so well that no one expressed to me that they knew all along when I finally emerged into my transgender world. They were all surprised that I never showed any signs of the true journey I was on with my gender.

When I finally woke up to the fact of who I really was, it was as though a tremendous weight had been lifted from my shoulders. I did not need my “Two C’s” so much anymore to get me by in the world. I was gaining the confidence I needed so I did not need as much courage as it took previously to carve out a new life as a woman and blend in with all of the ciswomen around me in their world. Saying that I was overjoyed when my life was coming together would be an oversimplification as age-old questions for me were starting to be answered. The main one was that I had been living my life backwards for decades causing conflict. Regardless of what society told me, I was never a man. I was a woman trying my best to lead a male life. For the most part I was successful, which made matters worse as my genders clashed for survival.

All along, I just wanted the battle to end so I could live my life in peace. I had my feminine side telling me how natural her life felt when she was allowed to live it. While at the same time, my male side was questioning why I would ever give up all the male privileges I had gained over the span of my life.

I chose the natural path which led me to a happy feminine life over the materialistic life which had only brought me stress because I was in the wrong place. Waking up was the best thing I ever did.

Thanks so much for reading along with my transgender experiences. Hopefully they can help you to understand yours too! 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.

 

 

 

 

 

Not Just a Visitor

 

JJ Hart from my Parttime Life.

When I began cross-dressing at a very early age, I learned I was so much more than a casual visitor to my femininity.

I knew because the feelings of wanting to be a girl just did not go away when the clothes came off and I needed to quickly return to my old male world. I was very resentful that I needed to return to being male because I had no choice in the matter to do it. Nothing seemed to help the way I felt except planning for the next time I could be alone and be the feminine person I wanted to be.

As I grew up, I did not grow away from my feminine instincts and desires, I grew into them and decided to gather the courage and leave my closet to see if I could make it in a world of ciswomen where I always wanted to be. Sure, I was scared when I first faced the world, but it was a natural progression for me if I was ever going to make it to my dream of living a transfeminine life. Following the initial clownish attempts, I made to present myself to the world, I settled in and learned how to present myself properly in a world dominated by the very women that I had put up on a pedestal early in my life.

Ironically, the two women that I chose to be my primary role models were the two women who tried to stop my transition the most. The first was my mom who was a very dedicated and popular schoolteacher who ran a very successful male dominated family from behind the scenes. Long before she passed away when I got out of the Army, I sat down with her and told her of my desire to be a woman. She quickly rejected me and said she would pay for a trip to a psychiatrist. Which was exactly what I did not want to hear because recently I had come out to a very small group of friends in the Army that I was a transvestite and was accepted. There was no way I was going to let mom push me back in the closet, so we never mentioned the subject again.

My second wife presented me with an entirely different challenge to my identity. She knew from the start of our relationship I was a cross-dresser but soundly rejected any ideas of me going forward into the transgender world of women. I had to respect her promise that she did not sign up to live with another woman, and it was the cause of many fights over our twenty-five years of marriage before she suddenly passed away. Regardless of all the negative feedback I received from both of them, I learned close up what it meant to be a strong independent woman in the world. While at the same time maintaining a family relationship. If I could ever be half the woman, they were, I could be successful.

Now, let's get back to that darn pedestal I put women up on for as long as I did. It took me years of trying to cross the gender border and being allowed to experience what was going on in the girls’ sandbox to do it. But when I did, I was finally able to destroy what was left of the pedestal I had built so many years before. When I was out in the world as a transgender woman, I learned the separate paths that cismen and women take. Since I had already learned the hard way about the male path, my next big challenge was to adapt it to the strong feminine world I was trying to survive in. One of the main things I learned was once you were out of the men’s club you were totally out for being a traitor and not following the fragile rules that men had set up over the years. Especially the ones that included any reference to their sexuality.

Women, on the other hand, were much more sympathetic to my cause. All the way to guiding me into women only spaces. There were very few times when I was completely rejected by ciswomen as I tried to be in their world. Probably the biggest reasons were they were curious about what I wanted there, and I was not up to no good as I was just being my authentic self all the time. Much more than being a part-time visitor. I knew from my experience as a man that women were much more in tune for BS from the world than men and embraced me when I did not have any of that negative aura around me as I was just the true me. Which I had taken years to experience.

It is no surprise to me that some think I am not trans enough to write about my experiences because I have never gone through any of the major gender realignment surgeries. Long ago when I could not afford any of the major surgeries, I decided I could live without them because my gender was between the ears and not between the legs. So, I set out to discover the best I could do to still live a complete life in a world of ciswomen everywhere. I ended up putting years into my pursuit of learning a new life, but all the work was worth it because I was able to carve out a new feminine life from the remints of a successful male life. Proving I was so much more in the world than just a part-time visitor into the world of women was certainly a challenge but with help I was able to do it.

I had the fork in the path long ago, when I had to decide to end my part-time infatuation with being a girl into the fulltime version of living the dream that I always wanted. Then I put my two and two together and hit the jackpot. I ended up winning my own personal lottery by finally listening to myself and doing the right thing.

Thanks for reading along! Any comments are always welcome!

 

 

Living Rent Free in my Head

 

JJ Hart. First Beauty Salon
Image

Living rent free in my head quickly became the motto of my feminine self.

It all began when I was very young exploring my mom’s clothes and makeup then expanded from there. Very early on, I gladly gave up the space in my head to a new and exciting person. Anything to escape the unwanted male prison I was living in. I did not like the day-to-day life I was forced to live as a male but could do nothing about it.

In the meantime, I was busy making space in my closet for a new person who was very demanding. She had to have clothes, and makeup to the best of my ability. And the problem was, I had to hide all of her from my family and friends because discovery would have been disastrous. As back in those days, any sort of gender dysphoria was considered a mental health issue. A place I certainly did not want to go.

As I matured into a more established cross dresser, there were several times when my closet experienced severe ups and downs when I needed to expand or limit the size and space I was working with. Perhaps, along the way, you have heard me refer to the term “purging” which means to throw away all your feminine items and resolve to go back to living a stress-free male life. For me at least, it never worked and just caused me to develop more stress later when I did not take care of the other inhabitant who was living rent free in my head. Always after purging, I found myself coming back stronger and better than ever when I remodeled my small closet into a more organized version to who I really was.

Who I really was became a very difficult answer for me to consider in my formative years coming out of the closet. Basically, the only constant I knew was I felt very natural when I was in my feminine mode and I felt a much deeper draw to it than just the thrill of wearing woman’s clothes. I did not know how I would get to a more transfeminine experience but just knew I needed to try. The problem was my male life kept getting in the way by throwing up obstacles such as military duty, marriage and jobs in my way. As much as I was fond of the woman living rent free, she was incapable of paying any of the bills which were coming my way after I got out of college and the Army.

Until I could go further in my feminine explorations, and hard as it was for me to do, I just had to back off most all I was trying to do for my ever-demanding transgender self. Once the term became popular and I could read up on it, the more trans made sense to me. So, I slapped the label on my other person living rent free in my head as it made sense to me and made me come closer to understanding the person I really was. As some wise person once said, you need to understand the problem before you can do anything about it. But before I could go any further, I needed to research what exactly I was getting into if I entered the world of ciswomen everywhere.

My world of exploration began in gay venues where I was just treated as another drag queen and even discriminated against on occasion. I quickly said enough was enough and I gathered my courage to attempt to establish myself as a regular in a few of the straight venues I had visited regularly as a man. I always had wondered when I was male what it would be like to go in several places, I was a regular in as a woman and finally I got the chances to try. I was overjoyed when I was successful in my attempts and quickly found myself in a world I had only dreamed of.

When I was doing all of this, I pretty much left my old closet behind completely as I stepped out into the bright lights of the world. After I accepted the fact, I would never be accepted in the world as a ciswoman, I set out to prove I could make it as a woman on my own terms and I did. I discovered I just had to live with my truth and most of the world would just be curious about me or just not care. All I was looking for was an even break for my rent-free person, and she got it. In fact, she got more than she ever bargained for as in a relatively short period of time, she was carving out an entirely new life as a transgender woman. My new woman friends knew I came from a different place than them but did not care.

It was a joyous occasion as all of them helped me to close my old closet for good and what about that rent-free person that lived there? She took over my life, saved the good through out the bad and overall constructed a new life for me that I had never dreamed of. As I suspected, she was not a squatter in my closet after all, she was the real deal all long and all the attention she demanded was paid back to me totally when the time came for pay back. In addition, she was nice and gentle about my male to female femininization project by telling me I had it all wrong. I was a woman hiding as a man for most of my life.

I was stubborn and shame on me for not realizing and reacting to my truth for as long as I did. But once my person in the closet took over with the addition of a few HRT gender affirming hormones, she was on her way to a freedom she would never have to give up again.

Hey you! Thanks for reading along and or commenting. Anything you do is appreciated and I hope if you are stuck in your closet, you can find your way out too.

 

Peeling Back my Gender Layers

 

JJ Hart with "Brutus Buckeye"
In the Ohio State Student
Union. 

Following the awakening I received from the numerous Halloween parties I went to “costumed” as my authentic feminine self, I needed to determine the complex path I would take so I could survive in the world.

What I ended up deciding on was a layered effect as I learned the ropes of the feminine universe I had only dreamed of living in. Like many of you, I started slowly with trips to my closet’s mirror, cross-dressed as what I thought was a pretty girl. In essence, the mirror provided me with my first layer to build from. Since putting on mom’s clothes was a relatively easy thing to do, I needed to concentrate on wearing her makeup which was not. No matter how hard I tried at applying makeup, I somehow ended up looking like a rodeo clown in drag. Adding this layer of expertise to my attempts to be pretty were intimidating before I started to see improvement.

Once I started to believe I had mastered the makeup arts part of my new life, I needed to add a new layer and set forth to do more about doing what I could to counteract the testosterone poisoning of my recent puberty. Since there was nothing, I could do about certain aspects of my body, I needed to do better in hiding them to the world when I started to leave the closet and explore. Those were the days of crash dieting and hunting through many thrift stores for just the right fashion item I could not live without. Mirror worship came back to help me during this layer of my life when I could honestly tell myself if an article of clothing really flattered me or not. I needed to get out of my teen cross-dressing fashion years and into a more realistic look I needed to blend in with ciswomen everywhere.

Blending in brought a whole new layer to my gender existence. To my relief, women had more of a tendency to embrace who I was becoming in their world, while cismen everywhere shunned me for leaving their club.  It all was an extension of my life as a man because I had never had much of a liking being around other men anyhow. I guess it all was a precursor to the person I was destined to become as a transgender woman. Probably, more than anything else, the Halloween parties I learned from helped me to be a success during this layer of my life when I was allowed to learn the basic differences between the two main binary genders. And landing squarely in the middle of both until I decided once and for all which direction my life would take. Should I take the easy way out and stay a very serious cross-dresser or follow my instincts and achieve my dream of living a transfeminine life.

To do so, I would have to add layer upon layer to my life by taking the old male building blocks I had used to get me by and use them as a foundation to build a better future. Little did I know what I was getting myself into as I was going past the princess-appearing layer of my life. For once, I was going to have to not listen to what my parents said about me when I approached any project I took on. To put it bluntly, they always told me I “half-assed” everything that I did just to get by. To advance through the gender layers that I wanted to, I knew I could not take the old approach to life I had always taken or I simply would not make it to my dream. It suddenly looked as if it was getting closer and closer to becoming a reality.

Before I just set all the male privileges I had learned aside, I needed to see what I was getting myself into. What would I really face as a fulltime trans woman if I ever decided to cross the gender border. I was selfish and wanted to see if I could peel back all the diverse patterns of life a ciswoman goes through before I went down her path. I was lucky in that all the right gender doors opened for me as I learned the ropes of being a woman in a supposed male dominated society. To do it, I needed to learn to leave the male domination behind me and learn a whole new society which existed for and about women. But I needed to earn my way in from all the gatekeepers in my way. I learned it was not going to be easy.

It did not help that initially I was so timid when I presented myself the keepers of the feminine world and it took me the “two C’s” to overcome it. The “two C’s” I speak of are courage and confidence. I needed the courage to think I was ready for my next gender layer and the confidence to do it. Somehow, I needed to get back out in society and prove myself all over again and carve out a totally new life as a trans woman for myself. I needed to keep reminding myself that yes, I was different, but what was wrong with that. I would never be a ciswoman but my socialization as a woman came from a whole different world you would not understand unless you lived it. Surprisingly, the gatekeepers let me in and I decided right then that HRT or gender affirming hormones should be in my future to provide a major kick forward in my transition femininization journey. I had done most of the hard work peeling back the layers I needed to learn if I wanted to do it and now it was time to take the easy hormonal way towards my future. I say easy because my body took to the hormones like what took you so long and all the changes seemed so natural.

The main thing I learned along my gender path was the number of layers I would have to peel back to achieve my goal. I knew going into it that nothing would be easy, but nothing prepared me for what I was about to face. Once I did face my reality that I was feminine all along, it was clear sailing to my dreams.

As always, thank you very much for reading along and I hope my experiences can help you along your gender paths. Comments are always appreciated.

 

A Halloween Political Decision

Image from Nice M Nshuti
on UnSplash

This is the second in my month-long series of Halloween decisions I made during and after the parties I went to.

This party took place in a wonderfully restored Victorian Mansion in my hometown where I worked as a radio disc jockey. Just to get an invitation was impressive to me as I struggled to come up with a “costume” to wear. Ironically, by this time in my life I had almost went full circle in my choices of what I was going to wear. I had long since gone from my slutty/trashy woman look all the way to a more moderate less clownish woman with my “costume.” I could still try to be sexy without going overboard as most ciswomen around me were doing on Halloween.

I finally decided to go full circle and see if I could wear something so authentic that the normal party person would not recognize me as a guy at all. I thought it would be the ultimate chance to test how far I had come as a transgender woman in the world on a low risk-high reward Halloween evening. Once again, my wife did not want to go with me, so I ended up with the news girl at the radio station as my companion for the evening.

I discovered I was off to a good start as my companion for the evening marveled at my “costume.” I chose to be a professional woman, just getting off from work and coming to the party to test my newfound freedom in the world. For at least one night.

When we arrived and found a parking place, I loved how my heels clicked up the sidewalk as my “date asked me how long I had practiced in the heels to wear them as well as I did. I just told her longer than it took me to shave my legs and apply my own makeup, so she left me alone after that. As far as asking any further questions about my skills dressing as a woman. Fortunately, it was a beautiful warm evening for Ohio in October, so I did not have to worry about any sort of jacket, sweater or coat as we made our way up to the mansion’s front door. The whole house was beautifully decorated for Halloween, complete with a vintage wooden coffin complete with a real skeleton.

I was met at the door by the hosts for the evening who like my “date” marveled at my male to female transformation. With the good start I was having, I immediately started to relax in my new surroundings and enjoy looking at the other costumed visitors. I was just about ignored as I did manage to blend in as a professional woman until later in the evening when a couple arrived and started to talk to us. It was just after a little bit of conversation that they told me, they did not recognize me as a man at all, and my “costume” had worked. My mind was shooting fireworks of joy when they told me that and it even went on to new heights when they even asked me to leave with them and go to a different party.

By this time, I had recognized the couple who were very active in politics and was on their way to Washington due to a recent election victory. So at least I knew who I was dealing with and if it had been just up to me, I would have said yes and went to the other party with them. But it was not just up to me since I had driven and I needed to get my “date” back home, so I had to sadly make a split-second decision and say no. Either way, I was very flattered by the offer and who knows what I would have encountered as my feminine self at the other party. We stayed on at the original party for a while had a couple more drinks and headed back to the house where I needed to reluctantly return to my old male life for what I thought was going to be another year. Always maintaining the “what if” ideas if I had continued with the politician and his wife, Maybe I could have gone to Washington also.

Another good thing that happened with the Halloween party I went to was, it was the first time that I ever thought/proved I could make it in the world as my true feminine self. Plus, I knew I could not wait another year for Halloween to roll around for me to live as a novice transgender woman again. If I had made it one night as a professional woman in the world, there was no reason I could not do it again. I just had to take matters into my own hands and do something about my gender dysphoria which was helping to wreck my mental health.

The evening was also more proof I had done the right thing for a change when it came to testing the strength of my male to female femininization project. I found I was coming along faster than I thought and I could never go back to living the totally male life I had before I tested the gender waters at the Halloween parties I went to as a cross-dresser. It was as if I had found a giant search light on my gender path and suddenly, my life made more sense. It was so much deeper than anything I thought it could be.

That is why not going out with the politician and his wife maybe cost me a chance at more fun and even enlightenment about who I really was. But on the other hand, I did the right thing by my wife and my date if she did not want to go early and end my evening. I felt better about it in the years to come. Even though, I wonder what would have happened if I had made the other decision. Most likely nothing and the memories are better than the actual experience.

Another reason Halloween will forever occupy a special place in my soul and there were several other evenings I will try to pass along before the actual holiday. Thanks for reading along and commenting!

 

  

The Season to Party as Your Feminine Self

JJ Hart
Cincinnati Witches Ball

It’s October, the season to party as your feminine self with no repercussions if you are lucky and have the chance.

In my case, Halloween parties that I gathered the courage to go to provided me with tons of valuable information I would use later in life. For example, I learned that just going to parties dressed as a trashy woman did not do me much good and when I went dressed to blend in with the other women around me, I was much better off.

My best Halloween evening ever happened to me when I was living in the New York City suburbs running a well-known fast-food chain restaurant and just happened to receive an invitation from one of my ciswoman assistant managers to a Halloween party that her and her friends were going to. Eagerly, I accepted and started to plan my “costume.” I immediately knew from my past Halloween adventures that I wanted to dress provocatively like many of the women do, while not going overboard and not appearing clownish. Since I already had the minidress, long wig and matching heels to go along with the dress, I knew what I was going to wear.

In all fairness to my second wife, she was not into Halloween and all the costumes that came with it, so she was alright with me going by myself although she highly disapproved of what I was wearing. As I was putting on my heels and makeup, she merely said be careful and out the door I went to a new adventure as I chased my feminine spirit.

Since I was relatively new to the area where I lived in New York, I had to navigate the streets in my truck as I wore my heels for the first time. I managed to do good and did not hit anything and anybody and made it to my manager’s house intact. Of course, I was beyond nervous as I found a place to park, adjusted my hair and makeup in my mirror and went up to her front door. When she opened the door, I was shocked and pleasantly surprised to see the friends of hers which were going to the party were all tall very attractive ciswomen with whom I could blend in with easily. When they saw me, they all grew silent until they realized I was not all I seemed to be. Out of pure luck, I had stumbled into a cross dressers dream of being around like-minded women for a Halloween Party.

From there, we wasted very little time leaving her house and heading the short distance up a couple of blocks to the neighborhood bar where the party was taking place. I was in heaven when I heard my heels clicking along with the other women as we walked the short distance to the venue. But it was just the beginning of a fantastic evening, I will never forget. It was like my first girls’ night out and I did not realize it.

It turned out, the venue we went to was smallish and dimly lit which was good for a novice, nervous cross-dresser like me out for a Halloween adventure. What I did not anticipate happening was being left alone by the other women I went with as they split up and began flirting with men they already knew. What I did was grab a seat at an unoccupied table so I could rest my feet. Somehow, I managed to go to the bar and order my own drink and head back to the table without attracting the attention of any of the other women I came with. However, I did attract the attention of an older cisman who sat down beside me at the table I was at.

I almost panicked when he offered to buy me another drink or wanted to know if I wanted to dance but I managed to say no to both since I had no idea if he knew I was not all I seemed to be and did not want to lead him on. At the same time I was flattered by all the attention I was getting, and my gender euphoria was soaring. I felt as if I belonged and fit in nicely in the venue I was in.

About that time, my new female acquaintances came looking for me telling me that they were leaving for home. All too quickly my Halloween dream evening ended, almost. On my way home, I drove past my restaurant and saw a stray car still in the parking lot. Ignoring for a second how I was dressed, I pulled through the parking lot and noticed one of my grill cooks in his car. By this time, I was emboldened by my earlier experiences in the evening and asked him if everything was alright. He said he was fine, and we ended up talking for a short time. During which he complimented me on the way that I looked and precisely about my legs.

Sadly, the glow of my evening was beginning to fade, and I needed to face the fact I had to return to reality and head back home. I walked away in my heels with new life/gender lessons I had learned for the first time. Primarily it is every woman for themselves when it comes to intermixing with men who maybe interested in you. Any loyalty fades quickly away. I also learned that under the right circumstances I could use the cover of Halloween to lip behind the gender curtain and see what was on the feminine side. Most importantly, I liked what I saw and wanted to experience more without having Halloween to help me.

When I returned to work the next day, I was interested to see the reaction from the rest of the crew and my boss over my “costume” the evening before. Overall, outside of a few knowing smiles from my boss and manager, life went on as normal with no questions asked so I was encouraged that my evening in heaven did not hurt my career, Halloween had given me the best of all possible gender worlds for at least one evening. I had to just figure out how I could have more without waiting another year.

 

Like the Bulb which Refused to Go Out

 

Image from Christian Dubovan
on UnSplash.
 

Years ago in another life, I bought a small corner tavern in an 1860’s era brick building in my hometown with a friend of mine.

My dad aptly called the bar the place flies did not have to stop when they flew through and I had to agree. But his criticism did not stop my friend and I from trying to make it the best tavern we could. When we were bored, we started to look around in all the saved junk that ancient bars accumulated and found a vintage, part wooden beer sign we could not wait to put up, even though that brand of beer did not exist anymore.

Amazingly, the sign had an ancient filament light bulb that still worked, so we used it and it kept on working for years. Later, I began to think of that bulb and how it could describe my gender conflicted life. No matter how hard I tried, my inner gender feminine light just would not go out. Not even a three-year stint away in the Army from the external expression of me being a cross-dresser could put it out. In addition, when I was honorably discharged, I found I needed to replace my inner gender bulbs with ones of a greater wattage to illuminate my dark, lonely closet.

Brighter bulbs helped to illuminate my feminine image in my closet mirror and helped me improve my makeup art as well as determine what clothes would be the right ones to wear. My new visions of myself helped me to speed up the cross-dressing experience and I just wanted to have more. That is when I began to take chances by going out into the malls and shopping centers close to my home. It did not make matters any easier as I learned how far I needed to go to successfully blend in with the ciswomen around me. Instead of displaying a small/dim bulb to succeed, to get to where I wanted to go, I needed a brighter bulb to display myself if I was ever going to make it as a successful transgender woman

At first, I was just using my light to interact with clerks and salespersons until I built up my confidence to do more. I was moving past my early days of Halloween exposure to the world as a trans woman and I was scared to death because for once I did not have the, “well I am wearing a costume” excuse to fall back on if I experienced any pushback for my cross-dressing in public. I was not up to no good, all I wanted was for my light to shine brightly in the new exciting world I was in. Unfortunately, in my early years, you might say I was a dimwit when my light bulb flickered and I thought it was going to go out. Those were the dark days of “purging” or getting rid of almost all of my feminine belongings and pledging to myself that I was going to turn the light off for good, put it all behind me and go back to where I was as a successful man.

As I said, those were the days of being a dimwit because deep down I knew I needed that feminine bulb to survive. No matter how dim it was at the time. Ironically, every time I “purged” I discovered very quickly I would need a much brighter bulb to sustain my life when I returned to my gender reality. Then I started to work hard to see what my new reflection in the world really was as a transfeminine person. I had to be constantly on my toes with my best behavior to do it as I was learning so much from every woman or the rare cisman I interacted with. It seemed as if I had to keep a constant supply of new bulbs handy every time I went out in the world. I always mention the stripping of all my male privileges as the main way which drastically dimmed my new light as a trans woman until I could replace the privileges with the whole new euphoria of being able to exist equally as myself in the girls ‘club I so desperately wanted admission into. It finally became evident to me; to be admitted, I had to find a bigger, better bulb to improve my overall presentation. So, I would never have to start all over again with my feminine life.

After years of experimentation and trying, I made it into the girls’ club where I always should have been in my life. And I put all those years of replacing bulbs behind me. Suddenly, my gender path became well lit like a large city street which I was able to navigate easily. With the help of powerful/magical HRT gender affirming hormones which helped me sync my external selves with my feminine inner self. I really became a whole person with all the gender benefits I had ever dreamed of. My emotions became clearer as I became more sensitive to the world. Among with the usual changes in hair on my head and breast size to my chest. Probably, most importantly, I was able to quit trying so hard with my makeup as my skin softened along my facial angles which made me more passable as a transgender woman. The world questioned me less, so I was able to change out fewer bulbs as I continued to play in the girls’ sandbox for the first time in my life.

The only regret I have is that it took me so long to follow my feminine destiny and live out my truth in life. I wasted too much time and money cross-dressing my life away changing gender bulbs until I got it right. I should have taken the time to write down somewhere the number of excuses I heard from my male self why I should ignore my truth and not try to live a life as a transgender woman. But I did not and the only thing I can fall back on is when my male life was good, it was very good and very bad when it was not. It is the only excuse I have to waste all those bulbs I did over the decades of gender experimentation I did to arrive at my destiny.

Hopefully, you can do the same. Thanks for reading and comments are always welcome!