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.

 

 

 

 

 

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!

 

  

How Difficult Could it Be?

 

JJ Hart

When I started my transgender journey, I was very naïve and I kept thinking how hard it could be to stay on my path.

All I saw was the good side of being feminine with all the girls around me in their pretty clothes and long hair when I was stuck in all the restrictive, boring male clothes and very short haircuts. To make matters even worse, I needed to make sure I kept all of my cross-dressing activities very hidden from the family and friends who would have ridiculed me and called me a sissy boy. The worst thing I could be called in my very male dominated family.

As I said, I was naïve and for years thought that all I wanted from being feminine was looking like a woman, so I obsessed about it night and day. Eventually, I did come closer to achieving my goal while all the ignoring harassing comments from my second wife who rarely wore any makeup at all. On the rare occasions she went out with me, she constantly thought I was going too far with my makeup and hair to the point of calling me the “Princess”. When all I was doing was trying to blend in with the ciswomen around me by overcoming my old male self.  Of course, I felt the criticism was not fair and the evening was ruined. Often before it even got started. From that point forward, the fights started because she did not like the trans woman I was becoming. And I did not understand why.

I think now that she thought I had not paid my dues as a woman yet to claim the socialization title and she was right. I was still stubborn and did not know how I ever was going to have the chance to play in the girls’ sandbox if I did not want it bad enough. I was stuck between two massive changes in my life which would either involve giving up the woman that I loved for one that I was learning to love. How hard life could be was becoming a reality for me like a boulder rolling down a cliff directly at me. It was quickly becoming unbearably hard when I discovered I could indeed see a path ahead of living my life as a transfeminine person.

What happened next was that I began to step away from my wife and essentially live the life she challenged me to live. That is to begin to socialize myself as a transgender woman in the world. I started to meet strangers as a trans woman who never knew me as a man and start all over in a new life. How hard could it be? It was and the whole process scared me to death. I was terrified of being stripped of all my old male privileges and having nowhere to turn if something negative happened to me. How would I be able to react to potentially negative situations in my new life. It turned out I did not have many potentially negative problems, and I was able to grow into my new feminine person with very few problems because most of the world did not care what gender I was. They were too wrapped up in their own worlds. Especially the cismen who were so afraid of their fragile sexuality that they left me alone. Which was fine by me, since I had always had a problem with making friends with other men when I was trying to be one anyhow.

Ciswomen, on the other hand, were much more willing to let me in their worlds and even show me around. Making it less hard to be one of them as I was learning daily how to fill out my life. I always had enjoyed being around women and found I even enjoyed it more when I was made a member in good standing of the girls’ club. Being in the club entitled me to use women’ only spaces such as restrooms which made my life so much easier also.

Most likely, I made some male to female transition issues more difficult than they should have been. Such as when I first came out into the world and thought everyone was looking at me, when they were not. I even went as far as to wear a favorite pair of sunglasses I had to see if anyone was staring at me without them knowing it. They were not, I was relieved and was able to go on with my new life. With new confidence I never had before. Maybe I could achieve my dream after all. It was a scary thought because then I had to start to think about what I was going do with all the excess male baggage I had built up over the years when I was trying my best to hide my true self by being a successful man.

The entire focus of my life changed as I began to consider the new and exciting reality of being able to live out my dream I had wanted since I was a child. I was sad when I could not tell the truth when an adult asked me what I wanted to be when I grew up and I could not say a woman and earn a quick trip to therapy by my parents. At the time, being a woman seemed as far away to me as being a lawyer or a doctor. But at the same time, a dream I really wanted to live.

Along the way, two things were evident to me. One of which was every time I achieved a goal on my path, another would appear for me to consider doing. And the second thing was, every time I began to doubt myself, I would start to feel natural about my journey and it would re-energize me, so I could move forward again. Forward was always good and made me feel better about my life which brings me back to my original point of how hard it could be to cross the gender border. Exceedingly difficult at times to be sure, but excitingly natural as I was doing it.

Wherever you are on your path to a better tomorrow, I hope you can discover your truth and make it in one piece. As always, thank you for reading and comments are always appreciated!

 

When Life Hands You Panty Hose

 

Image from Garin Chadwick
on Unsplash.

As transgender women, we find when life hands us panty hose, we better wear them.

In my case at least, I had an early love of wearing hose after I was able to borrow my mom’s electric razor and shave the unwanted hair off my male legs. Which puberty had gifted me with when I was not looking. Ironically, if the truth is known, I was probably shaving my legs ahead of many of the girls in school I admired so much. I say that because if my mom had the daughter she always wanted, she would not have let me shave my legs and wear makeup as early as I did.

During my early love affair with Hose, I discovered how frail they could be as I ran many pairs of my mom’s collection which she never mentioned to me. Since I was earning a meager amount of weekly income from my paper route, I discovered buying panty hose was within my reach if I could just discover the size and shade which fit me the best. I could go to the corner small department store, gather my courage and be able to buy a new pair of panty hose and an item of cosmetics and still have a little left over to save for my next cross-dressing adventure.

Since I was buying my own supplies, I felt less guilty about searching for clothes in my mom’s wardrobe which still barely fit me as I had less chances of being caught. But the new problem I was having was where I could hide my growing collection of feminine belongings where my family would not find them. Especially, my slightly younger brother. I even resorted to storing my overflow in plastic bags in an old hollowed out tree I found in the woods next door to my house. It was far from ideal, but I managed to have my privacy one way or another.

As I lived my life, I was still in my victim phase of wondering why I was the only boy I knew who was going through all the contortions I was going through to be a girl. Why could not I be “normal” like the rest of my friends. When they were thrown panty hose, they would promptly drop them like some sort of a hot potato. I on the other hand still enjoyed the electric feel of the feel of the material on my legs and how good my legs looked in the mini-skirted fashion of the day. Since I was told I had great legs at Halloween parties I went to, it was the ideal time to show them off with a pair of panty hose that I had just bought at a neighborhood convenience store. By this time, I was a pro at knowing just what I was looking for and always buying it with no problems.

Thankfully, I finally exited my victim phase of life and started to embrace and accept who I was thanks to a lifetime of cross-dressing. Since the term transgender had not been invented yet. By this time, I was entering the 1980’s with mini-skirts coming back in fashion along with the big hair. I loved the fashion of the day almost a much as I loved the old hippie days, I was largely deprived of because of my time in the Army. It was fun when I could look out for and adjust what I was wearing as a transgender woman, so I would continue to blend in with the ciswomen around me. Evolving with the times also involved how I evolved as a transfeminine person because I had a lot of growing to do if I was ever going to make it to my dream.

I needed to go back and accept what I knew so long ago that much more than women’s clothes and makeup defined me as a person. I yearned to be the women I admired so much and had to figure out how to get there. Which involved more than the simplicity of being presented with panty hose and having the chance to wear them. What would I ever do about putting in the effort to live out a life, cross the gender border and successfully exist in the world with other ciswomen. I write extensively about the time it took me to peel back the layers I needed to cross on my gender journey to be allowed to be behind the gender curtain. Where I looked merely opened a few initial doors for me. An example was what happened when I observed I was the only woman in the room who was wearing hose at all. Somehow, fashion had come full circle in front of my eyes and every time I saw a woman wearing hose, I looked closer to see if she was a cross-dresser.

As far as I am concerned now, my hose wearing days are almost over along with most of the women I am around. Sadly, I am into leggings and jeans now more than anything else because I do not go anyplace other than casual venues where I would be out of place if I dressed up so I have come full circle in my life once again. Life handed me panty hose initially and I embraced them totally before I moved on later down my gender road. However, the one fun thing you can do as a woman is embrace certain fashion styles the best you can. You are still not tied to the old restrictive male fashion code which evened to start to change also. Men now are even allowed to wear pink shirts, so who know what is in store for future men’s fashion. On the runways it is not uncommon to see a male model wearing woman’s clothes. Maybe someday, cismen will grow out of their frail sexuality, and the world will change with them.

In the meantime, I will always remember my beginning of a life of a discovery as a transgender woman. Life did not throw me any lemons, but it did throw me panty hose in an egg-shaped package. Which I used as a springboard to move on from there. I managed to proceed through a lifetime of gender discovery I used to come close to my dream. From there, woman friends of mine helped to push me across the line I was dreaming of. I was so fortunate to have had them to help me to yet another electric sensation. The of living an everyday life as a trans woman.

Thanks for reading along and making comments! Your input is always welcome as it helps me grow.

 

 

Is It too Early for Halloween?

 

Early fall Image
JJ Hart

As I look around the neighborhood I live in, I see people putting up their Halloween decorations already.

Then I began to think of the supposed “good old days” when about this time in September that I was starting to seriously consider what “costume” I would wear and how could I maximize its use by going to as many parties as possible. It just did not seem fair to me that I had to wait for a once-a-year party to express my feminine side without the fear of retribution. The worse that could happen to me were the other women at the party asking me who helped me with my makeup and did I really shave my legs for one night.  I was learning a valuable lesson about how curious ciswomen could be when you cross the gender highway into their lane.

Basically, my biggest decisions came as I thought about which theme I would follow year to year if I was going to the same party. And how creative could I be with my “costume” Ironically, my first big attempt at dressing feminine at a Halloween party came when I was still in the Army in Germany, when I was invited by my future wife to go to a hospital’s party. I had a couple of other wild friends who had their costumes already picked out and were coming as various forms of the male and female anatomy. So, I thought it would be an ideal time to fall from my cross-dressing wagon that I had been forced to be on for two and half years and come as a trashy prostitute.

I do not remember now how I got the clothes I needed to complete my outfit, but I was able to put together a short mini dress, long blond wig, hose and heels for a very effective costume. Since I still had approximately six months to go in the Army at the time, I was happy that no one seemed to care that I was dressed as a woman at the party.

When I was discharged from my military duty, and Halloween rolled around, I had a different challenge to face with all the newfound freedom I had. One thing I did was get away from the prostitute look and try to find a way to find a “costume” like what a ciswoman would wear.  In other words, I wanted to go to the party and try to pass as another woman enjoying herself. During the first multi-party Halloween night I went to, I think I did well. I went as one of the French girls I had seen in Paris when I was in the Army and brought the look home with me. I paired a all-black outfit which featured black tights, mini skirt and leotard with my blond wig, red lipstick and topped it all off with black flats and a black beret.

I was having a very good time entertaining myself in one of the big local clubs I went to which was having a Halloween party when a guy in a full mask approached me and simply said “I know who you are.” At first, I needed to recover from his comment before he went on to say, “I know because you look just like your mom!” Then I knew who he was and did not know whether to be flattered or not before he did not say anything else and went on his way. I did know I looked like mom but not that much.

From then on, I began to build my Halloween “costumes” from scratch and only used my many trips to thrift stores to help me with items for what I was going to wear. All I really knew was that I enjoyed my self immensely in my new world as a transgender woman and wanted to see if I could take it past the party scene and into reality. There would be other significant parties I will write about later, for now I had to learn if the build up to Halloween was totally worth it. I learned it truly was because of all the early lessons I would need to learn if I was ever going to decide to try to cross the gender border and live full-time as a transfeminine person.

I also realized that Halloween would be just the briefest thrill in what would be a long life of gender discovery. Would the overall gender euphoria of making it through the parties successfully be worth it when I had to crash back to reality and my increasingly boring male life. Plus, I found it was unbearable for me to just wait a whole other year to experience my feminine side again without me going out in public. I took my gender life into my own hands and began to explore the world in malls and outside in different venues such as bookstores which helped me build my confidence as a novice trans woman.

I went further, quicker than I ever thought I could and forever put Halloweens behind me as a necessity in life and more of a fun pursuit. In its place, I would be trying to carve out a brand-new feminine life of my own. It was the beginning of the most terrifying yet exciting time of my life. Mainly because I was stripped of all my old male protections and had to start all over again in a world where I did not know who to trust. Including myself because everything I knew was changing when I left the good old boys’ club for good and applied for membership in the girls’ club that I had so long waited to join. I was just at a point where I needed to convince ciswomen around me that I was serious and brought different qualifications to the feminine table. I had to suggest I was a woman too but just had been socialized a different way than they had been.

In many ways, Halloween was the earliest part of my socialization process thanks to the early interactions with ciswomen (and men) that I experienced. Immediately, I found that men I had known for years ignored me as a potential cross-dresser or whatever they thought I was. It did not matter. I was out of the club.  While at the same time, women I had known for years were curious about me. Lessons that had carried with me well in the learning years to come.

That is why I will forever miss the early excitement I felt around my early Halloween parties and why I still feel the fun I felt when I see the neighbors putting up their decorations early. Who knows, there may be a person in the family with gender issues also.

 

 

 

 

 

It Was Always a Challenge

 

Image from Dwayne Joe
on UnSplash.

As a boy and onward to manhood, I had plenty of challenges to be sure of. Early on, my challenges were in athletics where I had very little natural ability, except for a passion to play ball of any sort.

On the positive side, my love for sports kept the bullies away for the most part and on the negative side, I lost a lot when I played. In the meantime, my feminine side beckoned and I was challenged even more because once again, I was not blessed with very little ability to present well as a girl. Testosterone tore my body up and produced many results that I did not want such as a bigger body and hairy legs and arms. Not good for a boy who wanted to be a girl as the major goal in her life.

At that time, I did not realize how complex my life would become when I decided much later to pursue the life of a transgender woman. How would I ever maintain a marriage as well as a successful career as a man that I was expected to do, if I wanted to be a woman at the same time. It was the beginning of an intense amount of pressure that I needed to live with as it became part of my permanent baggage when at the time, I was trying my best to minimize my life. Especially when I was in the military and almost everything I owned was being shipped home, on my back or in my duffel bag. I would never be free of entanglements in my life that I had then.

Then, even if I was trying not to add more baggage, life set in when I was discharged from the Army and marriage as well as my first and only child were quickly coming my way. All along I was conflicted about the new challenges I faced, I had set up basic guardrails in my life such as telling my first wife I was a confirmed cross-dresser or transvestite at the time and trying to use birth control which ended up failing on me which I will not go into.

I suppose I had no choice but to accept the new life challenges I faced with parenthood and trying to build a career for her and my small family as I moved along. It was what I was supposed to do, and I was trying to meet the demands of doing it. What I never counted on was the strength of my feminine inner self. She was always demanding more and I was on the verge several times of responding to her call when I had very little other male baggage to deal with. But I did not and went on to struggle with my gender dysphoria the best I could by internalizing it. The only release I ever had was cross-dressing in front of the mirror for my own pleasure as I dreamed how it would be to live a life as a trans woman.

A well-known path out for me became the exciting Halloween parties I could go to in my favorite costume…as a woman of course. The parties showed me I could begin to exist on my own terms as the person I always dreamed of being. If I answered the challenge to do it. If I had the courage to present myself to friends as a woman, could I ever decide to do it as another avenue out of my closet and into the world. While I was at the first Halloween parties I went to, the more I learned of the basics of being in a new exciting yet scary world where I always wanted to be.

I learned quickly that cismen around me would avoid me completely, while ciswomen asked me questions about who did my makeup and how did I gather the courage to shave my legs for my “costume”.  Later on, I used the basics I learned from the parties I went to when I tried to meet the challenge of being out with other women who wanted to communicate with and were still curious why I would want to meet the challenge of being in their world. By this time, I was becoming more confident in my true feminine self that the thrill of going to Halloween parties disappeared.

Just because the parties went away and my confidence increased did not mean that the challenges I was facing went away with it. I needed to face the complexities of living a life as a transfeminine person head on if I was ever going to be successful, I needed to communicate with a world which wanted to know more about me for the first time and it was the hardest thing I ever had to do in my life. It was the time I had always dreamed of when I could finally put the mirror behind me and put the total new me into motion. When another woman came at me with questions, I was there to answer hers and was beginning to be able to ask her questions of my own by looking her directly in the eye and doing it.

The only advice about overcoming the communication challenges you will face in the world I have is to somehow get out of your closet and experience what is going on firsthand. By doing that, you can let your own unique personality out into the world and leave your unwanted baggage behind you if you are a transgender woman or a transgender man. The same rules apply, just in different gender worlds you must live in and react to. If you do not answer your challenges and try your best to get out of your closet, you will make yourself a victim and never do it.

Also, the only warning I have is depending on where you live, know the anti-transgender laws and attitudes you will be facing and plan ahead accordingly. Remember you can not rely upon the old male security privileges you used to have and find yourself in a dangerous situation. Ciswomen are raised to be careful of potentially toxic situations and avoid them too.

You can also use your challenges as a mini-bucket list and move on after you have accomplished one goal. It is a relatively easy way to manage your male to female or female to male transition.

Good luck with your challenges and thanks for reading along. I appreciate you and any comments you may have!

 

The Age of Gender Innocence

 

Image from Nicola Dowie 
on UnSplash.

I used to think that my initial days of cross-dressing were the most innocent days of my life. I was very young and the feel of the feminine clothes on my body and the expectation of seeing myself in the full-length family mirror brought me to the height of anticipation. For the moment at least, I was putting aside all the worries I had of ever being able to live successfully in a male world.

Now, with the benefit of age on my side, I wonder if I was ever so innocent. Sure, I loved all the things about being a cross-dresser such as shaving my legs and wearing panty hose, all the way to feeling all the sensations of being able to wear the same pretty clothes I had seen the girls around me wear. The biggest problem remained was that just the wearing of the clothes was never enough. The thrill I felt of dressing up was guaranteed to only last a couple of days before I could not wait to do it again. Even my young mind knew there was still something wrong.

What was wrong was I was not a cross-dresser at all; I was a transgender woman waiting her turn to live in the world. In the meantime, I would have to depend on the temporary thrills of mirror worship to get me by in life. It all set me on a very long path of gender discovery. Complete with many ups and downs along the way to make the journey either very scary or at least very interesting. It took me years of mirror living before I could ever gather the confidence I needed to finally conquer my fears and go out into the world as a novice trans woman. Of course, there were the on-going challenges of learning makeup as well as shopping for my own clothes on an extreme budget. When I discovered the thrill of shopping at thrift stores, I was able to find clothes that fit me well by having the chance to try them on before I bought them. If I made a fashion mistake when I got it home, it was not such a big deal because it did not cost that much to start with.

Rapidly, my days of gender innocence were fading away as I became more involved in the world of ciswomen. I quickly discovered their world was much more than just the external world of fashion, hair and makeup. Their world was so much more complex than a cisman’s I was not prepared for it. I found I had a lot of work to do to be accepted at all. To prove I belonged there at all, the first step was to prove I was serious about doing it. I would first have to prove to other women, I was not trying to enter their world as some sort of a dare, or that I was not up to something no good. I desperately wanted to cross the gender border and join the girls’ club and leave the men’s club forever. When I was able to, entrance behind the gender curtain opened for me like never before.

It took many times behind the curtain for my innocence to really go away. I needed to battle my paranoia with being shy to start with and then having to communicate on a whole different level before I could relax at the girl’s night’s out I was suddenly being invited to comfortably. And that was not the only one thing I needed to deal with. Such as how I would ever dress to blend with the rest of the ciswomen in the group I was invited to. I certainly did not want to embarrass myself by dressing too much or not enough and finding that special point where I blended right in. My innocence was real, since I was dealing with a world I had never been in before, but the pressure was real because I wanted to make it a success so desperately. I can compare the experience to first dates I went on with women I did not know well as a man. How would I start the conversation and what would I say.

It turned out I did not have to worry that much because the group conversation was easy to follow without men around. It flowed around family basically and the relationships the women were having with their men. I just flip-flopped my past life as a man to one of a woman. Being purposely vague about key issues such as not having the birth of my daughter but I was there when it happened. My communication efforts seemed to work with all but one woman who just glared at me. I ignored her glare and stayed in the conversation and got invited back.

As I experienced more of the world as a trans woman, the more my innocence went away. Sure, I encountered the occasional toxic woman or TERF but with my confidence level soaring I was able to handle most all of them. If you are wondering why I have not mentioned any men, it is because there were so few of them. For the most part, they knew I had left the men’s club and wanted nothing to do with me, Plus, I cannot take all the credit for my success I had a very tight knit group of women friends around me to support me too.

Perhaps the most lesson I learned about gender innocence was the amount of difference there is between the two main primary genders. Basically, I learned that men operate on some sort of a power matrix. When they are challenged, they are less likely to give you a chance unless there is something in it for them. Women, on the other hand, are much more open to the world. Especially when it comes to their sexuality, which is not as frail as a man’s.

As I always say, if you are just starting up your gender path, be prepared for a change in your innocence as you enter the world of your preferred gender. And thank you for reading along as I described mine.

 

 

Just Another Lonely Day

Image from Jarge Johansen
on UnSplash.

Throughout most of my life, I was desperately lonely, as I had no one to fall back on as I explored my gender issues.

Growing up in a rural area, I started with just a
small circle of kids I interacted with and it rarely grew significantly, so again I was stuck with why I felt the way I did about myself. All I knew was I had a difficult time interacting with the boys at all and the girls seemed as if they were some unreachable magical creatures I knew nothing about.  While all of this was happening, all I could do was carve out my own little world where I was a pretty girl in front of the mirror in mom’s clothes and makeup.

Little did I know how those humble cross-dressing beginnings would come back to influence my life later. In fact, forever. As I grew, I became more skilled in using makeup and finding clothes which I could fit into when I outgrew moms. Then, the more I cross-dressed, the more I wanted to. Which did nothing for my extreme loneliness. It seemed to me; I would never find a way out and really did not until I hit my late high school and college days. What happened was, a group of girls at high school learned that a friend of theirs did not have a date to the junior prom and I did not either and matched us up for the evening. After a successful date, I was not so lonely when another friend of mine set me up with a single girl he knew and suddenly, I was a socialite as I entered college. In truth, deep down I was still the deeply conflicted person I always had been.

Amazingly, my early college years were so intense that I forgot about my gender issues for six months or so before they crept back in. When they did, they became as intense as they were before I left for college and stayed that way until they were put on my back burner when the military draft caught up to me when I graduated. For a while I was engaged to a woman I knew from college until she left me just before I was due to report to Ft. Knox for Army basic training leaving me completely alone again. When my fellow soldiers were getting mail from wives and girlfriends, I was getting an occasional letter from mom. At the least, I appreciated her efforts and once again I was back to being used to being intensely alone.

All along I wondered what my military time would do to my gender issues. Would they go away temporarily like they did in college or not was my question. The answer I was looking for did not take long to become evident to me. No my gender dysphoria was not going away and in fact, tools I had learned in the Army just made my dysphoria stronger. For example, I became more confident in myself as I had a better idea of what I could survive and I spent hours of what spare time I had daydreaming of what I would do with my feminine self once I had served my three years.

It was not very long after I was discharged that I gathered the courage to ask my first wife to marry me. Since she was in the Army too with me for over a year, she had witnessed my Halloween party costume at a hospital party we had went to with friends. Plus, my later confession to three friends plus her that I was actually a transvestite and my costume went a lot deeper than it looked. She also turned out later be the mother of my first and only child and the marriage did last several years until I fell madly in love with my second wife.

Oddly enough it was another Halloween party which allowed me to confess to her my deep dark secret that I was a cross-dresser. It turned out that she did not care which was the case for the twenty-five years we were married. Until I began to transition into a transgender woman. Just before she passed away from a massive heart attack. During those years we had our share of good times and bad times somehow, we always made it through, and she never knew how much of a role model she was to me when I went my separate way as a trans woman. Following her untimely death at the age of fifty.

When she passed, I went into a lonely shock I had not felt through the majority of my life. I could not understand why I was having to start all over again in my mid-fifties and search for another relationship. And furthermore, which direction would I take with the gender issues I had during my life. By this time, I was well ahead of my goal to possibly live as a transfeminine person. I had major decisions to make in my life, so I kept on searching for answers. To start with, I tried dating ciswomen again as a man which failed miserably and at the same time, get more serious in my explorations ss a trans woman which I found to be a natural social release for me.

By the time a couple more years of wasting valuable time went by, I was sitting by myself enjoying my new company and I thought why was I not living like this all the time? How stupid could I be not to take advantage of what I had learned in the world so far as a transgender woman. Most importantly, my lifetime’s dream of living as a woman was within reach, and I was not taking advantage of it.

From that point forward I put together a timetable to give away my remaining male clothes and pursue HRT therapy. There would be no turning back from that point forward. I was tired of the gender struggle and loneliness I was enduring. I was afraid if I did not make the change now, I never would have the chance.

You might say I played the odds and they came out in my favor but on the other hand, I researched the odds extensively before I did it.

 

 

 

I Wish I Knew Why

 

 

Image from Jon Tyson
on UnSplash

It has been a while since anyone has asked me when I knew I was transgender. In fact, it was several years ago when one of my grandkids was coming out to my daughter as being trans.

My daughter then asked me if I had always known, true? I told her yes that was true except in the exceedingly early days of my life when I knew something was wrong with me but I just did not know what. As I grew older and I experienced that first magical visit to mom’s clothing drawer did I truly knew what the problem was. I really liked the feel of mom’s clothes and that was only the beginning as I wanted to be a girl full-time sometime in my life. Just the buzz of wearing feminine clothes was never going to be enough. So, I set out on a long journey to see if I could ever achieve my dream.

When I was able to begin to interact with others with gender issues, I found early on that it was not going to be the end to my questions that I thought it could be. For example, I was too much girl for many of the cross-dressers I met and not enough woman for the then called transsexuals I encountered in person at the social/mixers I traveled to. The closest ones initially were nearly a two-hour drive away before mixers were then set up in a nearby central location for me. It was then that I was able to meet others who identified as true transgender women and I fit in perfectly with them. Finally, I began to have answers to my identity as a person.

Of course, I needed to take all sorts of side journeys as I sought out the key to why this transgender world had chosen me. In my research I even came across the theory that the drug “D.E.S” which was given to women with a history of problem pregnancies around the time I was born, could conceivably be linked to a person having= gender issues later in life. Because to ensure the fetus went full term in the womb, the womb was flooded with estrogen to aid the birth process. I thought “D.E.S.” might fit me because my mom had suffered through three still births before I came along. Ultimately, “D.E.S” stayed just as it started with me. Another solution to an extraordinarily complex gender problem with no concrete answers.

Then there was the victim mode I wrote so much about when I went through a poor, poor pitiful me time of my life. I could not understand why I needed to be stuck with all the gender issues I had when no one I knew had them either. To this day, I envy men who have been able to go through their lives as men without the added distraction of wanting to be a ciswoman. Finally, I made the difficult turn considering my overwhelming desire to be feminine as a good thing. Because it set me off from society as a unique person with a look at both sides of the gender border. Removing my victim mentality made all the difference in the world to me as I began to look ahead for the possibilities which laid ahead. Rather than always looking over my shoulder and dwelling on the mistakes I had made.

The more success I experienced when I first was able to carve out a new life for myself as a transfeminine person, the more the wish I knew mentality I had lived with my whole life began to fade away. From that point, I went into my confidence mode because without it, I was powerless to do anything I wanted to do as a trans woman. I found that as long as I held my head high and did my best to be a quality person in the world, the more people left me alone since humans are like sharks. They sense blood in the water, and I was not adding any of mine. Confidence also allowed me to try different things. To judge if I really wanted to jump the gender border and give up living life as a man altogether. Even though it was the most difficult decision of my life, having even a sliver of hope that I could live my dream that propelled me forward to a gender tipping point that so many ask about.

This time, I could tell anyone who asked why I decided to leave a successful male life to take on a decided uncertain one as a transgender woman. The answer I always gave was deceptively easy. I had reached my own gender tipping point where I was living more as a woman (and feeling natural doing it) and less as a man as I was feeling increasingly uncomfortable doing it. By doing as much research as I had, I had given myself no choice as what I should do. When became now and that was the time, I decided to take the next step and pursue gender affirming hormones or HRT to sync my inner mind with my external body the public saw. I knew it was the point of no return for me as my body took to the new hormones magically.

I knew from there that all my explorations as a trans woman pus the addition of HRT allowed me the most powerful female privilege of all. The power to finally be myself. The wish I knew why I was different my whole life was answered with a resounding yes, I did know it all along and refused to face my own truth. I was living a counterproductive life as I was going overboard trying to be successful as a man when I was a woman forced into her shell all the time struggling to get out. The best part was when she said I told you so, as she destroyed what was left of my old male ego.

I finished strong when my why me became a why not as I had the chance to live my feminine truth among the ciswomen of the world.

Thanks for reading along and I hope you will discover your why me in life! Comments from you are always welcomed.

 

 

 

 

It Was Exhausting Waiting for the World

Dustin Hoffman in "Tootsie"

 Over the years, it was exhausting for me waiting for the world to catch up to me.

As I always mention, I was born into the pre-internet and social media years when information about any gender issues was difficult to find. I am old enough to remember the sensationalized reports on television in Dayton, Ohio when the police staged raids on “homosexual” venues and I saw them arrest men dressed as women.

In addition to the negative publicity I was watching, I knew from my limited research from books at the library, that cross-dressing was considered to be a mental illness which I did not feel was true with me. I was not mentally ill, I just wanted to be a girl, and it was simple as that. All it did was put extra pressure on me to never be discovered by my family or my brother in the feminine clothes I had found.

I felt so all alone as a “transvestite” as we were known back in those days until my second wife and I purchased our first home computer. Which opened a whole new world to me including a way to contact others with gender issues such as me. Before that, all I had were the “Transvestia” Magazines I subscribed to and the “Tri-Ess” social mixers I drove hours to get to. I could not believe the world was suddenly at my finger tips when it came to discovering others outside of the “Tri-Ess” community.

All went well, until my second wife caught me in one of the old “AOL” chatrooms having a private conversation with another cross-dresser in a nearby city. I needed to learn quickly on how to cover my internet tracks better if I was ever going to stay out of trouble. The world was not catching up to me as I was catching up to it through the power of the internet. Then 1982 rolled around along with the classic gender movie of all time, “Tootsie” with Dustin Hoffman in the lead role as an actor who lands a soap opera job playing a woman with life changing experiences. For once, there was a film which did not portray a man in a dress as a criminal up to no good and I could not wait to see the film.

With the resultant good publicity which came from “Tootsie” I thought that maybe the puritanical gender ideas of the country would have changed and the public somehow would be more receptive to cross-dressers and transgender folk forever. Of course, I was being naive and over time, the public shifted back to the same old place it had always been…not accepting to people with gender issues like me.

Sadly, I had to go back to carving my own path as a novice transgender woman on my own without the publicity of a movie to help me, including the daytime talk shows which were the new television craze. It seemed to me that every week, one of them featured something about a cross-dresser on their show. In all fairness, some productions such as “Phil Donahoe” tried to present a fair view of our culture while the “Jerry Springers” of the tube just sought to sensationalize us. So, once again, the world had not caught up to me at all and did not help me when I needed to carve out my own life for a change in the world. I did not want another ciswoman thinking she was talking to a future “Jerry Springer” person, and I was real and down to earth. I was just trying to live a normal down-to-earth life like she was.

By this time, I had given up on the world ever catching up with the complex lives that transgender women and transgender men lead. It is why unless you are a very open person and secure in your world, you will never understand where we are coming from. That is fine, you do not have to understand, just do not try to stand in our way as we try to live.

Now I worry that all the fragile transgender rights we had gained under recent presidential administrations in Washington will be erased to an extent it will take decades to ever get them back. Then, I will have lived long enough to go from the “Tootsie” era of understanding to the “Orange Clown’s” world of rejection of our right to even exist. An experience I never wanted to have, and it is even worse here in my native Ohio where the state recently revoked their gender change requirements for driver licenses. So as they used to say back in the day on Top 40 radio stations the hits just keep on a coming.

Every once in a while, I hear rumblings from the regime in Washington trying to do away with my gender care through the Veterans Administration. So far (knock on wood) I have been part of the program for so long, and it is tied to my depression issues I have flown beneath the radar, and I hope others can too.

As a tribe, transgender folk have always existed through time, and if you are just realizing your potential as a trans person, welcome to a scary yet exciting world where you can be yourself. At least you can fall back on the resources you can find on the internet to help you and bring a little light into your dark closet you have been in for so long. Just remember not to let the brightness of your new day blind you to your new reality.

In the meantime, the world has caught up to you in your own way. Enjoy it because you have endured so much to get here.

Thanks so much for joining me in my lifetime of gender trials and tribulations! I set out to help anyone I could, and I hope that is you! All comments are welcome.

When My Tomorrow Became my Today

JJ Hart

My desires to always look like a pretty girl early in life led me to always be a tomorrow person.

 I always thought that somehow tomorrow I could get a real wig, nicer clothes and more makeup which would help with my feminine transformation. I guess you could say that the whole process made me into quite the dreamer as I sat in school and envied the girls around me in their pretty clothes I could not have. At least today but maybe not tomorrow if any of my dreams came true.

Soon I discovered that dreams never came true on their own and would take an enormous amount of work on my part to make a dream happen. Especially once as complex as crossing the gender border to live a transfeminine life. I often wonder if I would have had an ounce of foresight into how difficult I was going to have it; would I have ever undertaken such a crazy path to begin with. One which would completely consume all the spare energy I could use.

The first problem I had to conquer in my feminine life was my often-frustrating attempts to look like a woman and not some sort of a clown in drag at the circus. I found I was setting the bar way too high in my appearance standards as there was never going to be a day when I could match the prettiest women I envied. I just needed to blend in with the rest of the ciswomen in the world just going about their everyday lives. It took me many painful attempts at presenting properly as a trans woman before I got it right and was able to move around in the world without causing any undue attention to myself. When I did, I was happy to stay in the present until my brief gender euphoria went away. As I crashed from the euphoria of living as myself, I was bitter, nasty and tried to take my frustrations out on the world of ciswomen around me. Why could not I be like them and live in their world held me back in mine, so I kept dreaming about the next time I could I could live my dream in the world fully cross-dressed as a woman.

The good part was that all along I was becoming better in my presentation as a woman and was finding it easier to cross the gender border. The bad part was once I did it, I wanted to stay and not go back to the male I was living. It was then that my todays became longer, and my tomorrows seemed further away. My new mentors became the established transgender women I had met at the socials I was going to in nearby Columbus, Ohio. They had crossed border and were living successful lives and I wanted to learn more about how they did it. What I learned was that every trans person’s journey was different and it was rarely ever easy. All I ever knew was that every time I was accepted into their circle, I felt natural and wanted to learn more about them.

As I look back on it, the one thing the mentors had on me was their natural beauty which I never had, so I had to keep putting my tomorrow off until I found out I could do a male to female transformation my own way. Or out of sheer willpower as I had a transwoman friend of, mine tell me in a straight bar we were in one night. By this time, I had given up on any natural feminine beauty I might have and made my tomorrow become my today by using other strengths ciswomen bring to the table when they don’t happen to share the extreme passing gene that some women have. They go on to lead fun and fulfilling lives by tuning out all the demands to be beautiful they hear. That is what I had to do because for sure ciswomen come on all shapes and models and I could certainly find a group I could fit in with. Which in my case, happened to be lesbians.

I was really seeking out the company of lesbians so to speak; I just happened to stumble across their culture at a small lesbian venue I started to go to as well a through a bartender at a big sports bar I used to go to who introduced me to her mom. Through it all, I knew the next step for me was to become more feminine by using HRT or gender affirming hormones. My approval to take the hormones focused my tomorrow so much I could not wait to get there. I changed during the time I was socializing with my new lesbian friends who took me to watch sports as well as big lesbian mixers. I was having the time of my life as my tomorrow was rapidly becoming my today.

Maybe most importantly, my friends helped me to validate myself as who I was really was as the subject of my past life as a man never came up. They did not want to know, and I did not want to bring it up as I was just appreciating my spot in my new present as a transfeminine person.

The final touches in my today came when my daughter accepted me totally and I met my current wife of over a decade Liz. They helped rid myself of any lingering doubts of how I should live my life. Over my gender cliff I went into their soft arms and my gender tomorrow was gone for good.

My only passing regret was that it took me so long to face up to who I was always was as a full-fledged human being. There was no way I should have let it go as long as I did, I should have let tomorrow be my today. I was all wrong as I tried to cross-dress my pain away. My excuse is I was jinxed all along into leading a backwards gender life thinking I was a man trying to be a woman rather than the other way around. That way, I would have never let my todays and tomorrows get mixed up the way they did.

 

 

Being Accommodating...Not Intimidating

 

Image from Billie
on UnSplash.

Being accommodating versus intimidating was very difficult for me as I transitioned from male to female.

It was all part of learning a new feminine world and escaping the male bonds I had suffered so long from. What happened was, I was thrust into a male dominated world in which if I was ever going to survive, I would have to play the intimidation game of life. That way, I could stand a very good chance of keeping the bullies away as I matured. It did not hurt that I developed into a larger slightly above average sized male person (which I hated) but again when I added sports into my life’s mix kept the doubters away from my masculinity. In fact, I needed to play that intimidation card well into life and used it before I transitioned into a transfeminine world. Intimidation became easy to use for me, and I counted it as one of my male privileges even though I stopped short of ever being a toxic male because I respected all women so much. But it worked well with the male kitchen crews I needed to manage in the busy restaurants where I worked.

The problems began with my basic personality outlook I had been forced to live so well when I began to try to join a world which was largely controlled by ciswomen, not cismen as I always thought was the case. Women just found unique ways always to work around males and their drama. And here I was in the middle of a new world just trying to find my way successfully.

I felt it most intensely when I was forced into communicating one on one in the world with other women. I found I was unprepared and initially just tried to keep my mouth shut, which turned out to be exactly the wrong move to make. Here I was trying to make new friends in a feminine world without talking? How was that going to work. It did work. In exactly the way I did not want it to. If I did not express who I was, the other woman I was trying to communicate with just assumed I was being standoffish or in some way stuck up which was the last thing I wanted to do. So, I immediately trashed my male scowl and quiet behavior as a form of intimidation to keep people away and went to a more open form of interaction with the public which invited people in. In many ways, it was one of the most intense and scariest things I ever went through in my life. I was in uncharted territory for sure and even resorted to feminine vocal lessons to help my progress.

And then there was the experience I had with a small girl who startled me in a clothing store I was in. She ran around a rack of clothes and almost hit me and went running back to her mom saying something about a “Big mean woman.” Immediately I was relieved that she got the woman part right but right then and there decided to do more about the old male intimidation factor I was obviously still carrying with me. In no way did I want to go around scaring little kids.

Life went on, and so did I as I started to feel more secure in my new role behind the gender curtain. I learned that many ciswomen were just curious about who I really was in a world in those days dominated by day-time sensational talk shows such as Phil Donahue and Jerry Springer. Here I was. The real deal cross-dresser or transgender woman right in front of them to talk to and know that I was just a normal person like them after all. It all happened because I had the courage to let them into my world and turn my old male intimidation ideas off for good.

Perhaps the most intense topic in the intimidation versus accommodation discussion came from my initial introductions to the women’s restroom. It was the exact opposite from the men in many ways except the obvious. In the men’s room, you were expected to never make contact or acknowledge another man while in the women’s room just the opposite was true when a polite smile or greeting was the proper way to acknowledge another woman. It took me a little bit of time to get used to the change, but I did it quickly because I wanted to earn my women’s room privileges desperately. For obvious reasons, I was drinking a lot of beer.

I see intimidation versus accommodation as just another step in acclimating yourself into the feminine world. But you have to do it right to be accepted. You must be yourself behind the gender curtain you choose without becoming a doormat. As an outsider to transgender men everywhere, my thoughts are it probably is more difficult to assume an intimidation role in a male world. On the other hand, accommodation in the female world I was in was always an easier path for me to take. I just had to understand and react to anyone who was setting up to take advantage of me. I came away with plenty of claw marks up and down my back from unfortunate experiences I had in a new (to me) passive aggressive ciswoman world. I learned often that a smile meant nothing in most situations when another woman was just sizing me up.

In the end, the whole experience just boiled down to very important experiences I needed to learn to finally make it out of my closet and into the world as a transgender person that other people would like to know and often my smile was the beginning of that process instead of my stay away old male scowl. The fun part often was seeing the results from the amount of learning I needed to do in my stubborn head to make it happen.

As always, thank you very much for joining me along my gender path and I hope you gained something from my mistakes. Any comments are always appreciated!