Back Up Plans

 

JJ Hart visiting Key Largo.

Following several near misses as a novice transgender woman out into the world, I began to smarten up and have back up plans when I was in perceived danger. 

After the near misses with security problems on dark streets where I should have never been alone, I hurriedly went home and looked to see if there was anything in my cross dressers handbook which would have alerted me to possible issues. Since I had a beginner's handbook, I found no such warning and because I had been raised male, I went on my way like nothing should ever happen. Well, it did, and I was fortunate to buy my way out of the problem with my last five-dollar bill. From then on, I learned my lesson and never went back there without an escort of some sort. Common sense had set in. 

Many other of my problems early in my public life as a cross dresser or transgender woman came from other less than intelligent decisions, I made on my own which set me up for failure. Such as the night when my second wife and I attended a diverse mixer in Columbus, Ohio. Against her wishes, I wore a very short mini dress with my long blond wig and ended up being trapped and nearly accosted by a much larger and aggressive "admirer" in a narrow hallway of the house we were in. My wife showed up and he backed off, giving her an ideal "I told you so" moment. From that experience I learned how helpless a woman could feel when trapped by an aggressive man. I went home and added it to my back up plans for the future and scribbled it into my mental gender notebook.

Other experiences were less stressful and even more humorous. One I will never forget was when I was tempting fate with wearing water balloons as breast forms. The double-edged sword of wearing the water filled forms was they were very fragile. Especially when I ignored the danger and made the balloons bigger. All went well, until the night one broke while I was out drinking in a venue, I was a regular in. I was lucky, when the mini flood cut loose, I was already heading for the women's room which happened to be deserted.  I was able to clean up, pay my tab and leave without further incident. I did not think telling the staff I was pregnant would have worked. When I arrived home, the water balloon breast forms became history for me, and I saved up for my first set of silicone forms. 

As the years flew by and I became more interactive with the public, I began to fill out more and more of my transgender workbook, complete with backup plans. I learned to be more cautious with my plans, allowing for more of the inevitable problems which would crop up. Even still, I was caught unaware on several occasions. One of which comes to mind when I was innocently chatting with another woman's husband when she went to the restroom. When she returned, in no uncertain terms, she made it clear I was not supposed to talk to him. My back up plan was to quickly leave, and I did.

I learned also, as I transitioned away from the male gender, very quickly I lost all my male privilege too. The old bluster my way through potentially dangerous situations went away. All of a sudden, I needed to look ahead and not put myself into those situations to start with became important. Many times, I needed to think if things could go wrong, they would. Before it was the same for my spousal relationship, I needed to begin coming home earlier so I could take off my makeup and clothes before my wife returned home from her night shift. Most of the time, I did make it, but when I did not, there was hell to pay. 

Finally, when I became freed up to live my transgender womanhood, I could store away most of my back up plans and move on. However, many of the plans I discovered were just part of being a woman anyhow, so I considered them a rite of passage. Other women grew up learning about the gender rules (right or wrong) and I needed to do the same. 

Once Your Eyes are Opened

 

JJ Hart, Club Diversity, Columbus, Ohio

In my case, once my eyes were opened as a transgender woman, I could never close them again.

Perhaps it is because I went through so many trials and tribulations to arrive where I wanted, or even desperately needed to be in my life. Since I had so few natural feminine traits to work with, I really needed to work hard to achieve a feminine presentation. I tried all sorts of ill-fated ideas before I ever got it right. Yes, it was me making the routine cross-dressing mistakes such as attempting to dress as a teen aged girl when I was thirty and had a testosterone poisoned body. All I accomplished was directing unwanted attention to myself. 

 It took me awhile to realize what I was doing, and my eyes were finally opened to what I was doing. The perception I had was I was dressing for men, when in fact, I should be doing the opposite and dressing for the women around me I needed to co-exist with. I learned the hard way, women ran the world I wanted to be part of, and I needed to do my best to get there. All of this meant I needed to keep my eyes open and do the best I could to study the women around me. Or how did the women react to the world around them, good or bad. 

Sadly, blocking my way were women such as my second wife who wanted no part of living with another woman, transgender or not. She was content with letting me learn on my own what women needed to survive in the world. Looking back on it, her process for me was the best way to go because once I learned something in my new transgender womanhood, I never forgot it. Also, magically, once I opened one door to my new life, my eyes were opened to another door. 

As I opened a new door, I knew I could never go back to my old male life which was bringing me down. I felt so good and natural in my new life, there was really no choice to be made. The only problem was what was I going to do with all the male baggage I had acquired over the years. Similar to most of you, I had the usual assortment of spouses, family, friends and employment to deal with. Fortunately, I started my transition process with the person who turned out to be the most accepting of all my family and friends. I am speaking of my daughter and her immediate encouragement helped pave my way to more attempts at telling the world about my authentic self. I ended up going one for two in the family process when I was roundly rejected by my brother and his family. He opened my eyes to what transgender rejection could really be like.

Still, I persisted, knowing I was on the right path and my eyes were not deceiving me. It took me awhile, but I finally gained the confidence to look another woman in the eye and communicate one on one with her. To do so, I needed to not concentrate on how I sounded and instead put an emphasis on what I said. In order to survive, I needed to keep my eyes open at all times because certainly every other woman was not going to be my friend. 

I did keep my eyes open and learned the hard way to keep my head on a swivel. There were many claws I needed to be aware of. Quickly, I was hardened to what the new world was like around me. More and more, I could never go back to the male privileges I had before. Even though, I lost much of my intelligence according to most men and especially lost my personal security, I still wanted more and more of my transgender womanhood. 

You might say, I acquired new 20-20 vision and it was perfect in many ways. It was a long and difficult learning process, but it was the best life I could have ever imagined, and I just felt I had done it sooner. 

Your Personal Best

 

Image from Markus Winkler
on UnSplash.

If you have ever worked in any sort of a competitive industry, perhaps you have heard a phrase similar to keep your eye on the ball.

Many times, in my long journey to being a full-fledged out and about transgender woman, I have wished I paused to remember such a goal. One image comes to mind when years ago I was trying to pump gas into my car at a gas station along the interstate when I was traveling back to Cincinnati to meet Liz before we were actually married. 

To begin with, I was a little flustered, even to the point of panicked when I discovered I did not have much money at all on my debit card and had no cash at all. As I said, I was nearly panicked and ended up pulling up to the wrong pump to try to fuel my car. For some reason, I had chosen a diesel pump and fortunately was having no success in putting the nozzle into my gasoline powered car. As I struggled, a man pulled up nearby and came to my aid by telling me I was at the wrong pump. I profusely thanked him and moved to the correct pump but not before I needed to go in the station and pay. Exactly what I did not want to do. I had no choice due to my mistake and needed to finally go inside and confess my mistake to a clerk inside who had no sympathy for the dumb person making the mistake. 

It was just one of many times, I took my eye off the ball and barely snuck by with a little help from above. Another time I remember was one night when it was snowing quite a bit, but I decided I needed to go out anyhow. With out giving anything much thought, I figured the night would be ideal to wear my new medium heel boots to give my fashion image a personal boost. All was going well until I went into one of favorite regular venues and found a seat at the bar. All along, I was confident I could slide down off the bar stool without falling. It turns out, I was overconfident as I tumbled very a womanly fall to the hard floor. I was lucky and all I hurt was my pride. From then on, the boots remained in my closet when it was snowy or even wet outside. 

Most of the time, when I was pushing the envelope and taking my eye off the ball, it was not because I was trying to do my personal best as a novice transgender woman. Even though I had established "safe" places I could go, I kept trying to go other places where I was not welcome such as the one lesbian bar I kept trying to go to. Unlike the other lesbian venue, I was accepted in (which accepted me), the first place tried to make my visit as uncomfortable as possible. Until I finally just stayed away and gave all my money to the place where I was liked. Once I did that, I could relax and enjoy myself.

I learned also, my personal best was not exploring the limits of where I should go as a transgender woman. It meant staying off dark urban streets by myself, or even unlit mall parking lots. I had not realized yet I had lost my male security privilege and needed to add a whole new level of security to my life.

Through it all, as I made my gender journey, I slowly learned how to keep my eye on the ball and do my personal best. Anything less, and I would revert back to my old unwanted male life and find myself back to where I started. Equally frustrating, was the fact I would have wasted all the time I put into pursuing my goals. I found my path and decided to stick with it.  

Running and Hiding

Image from JJ Hart archives,

I spent over a half of a century in my life running and hiding from the gender issues I faced all of the time. 

First, most of the time I hid my desire to dress like all of the girls around me. Of course, in order to accomplish anything, I needed to suppress any urges I had to be at one as a girl in the mirror. My Mom never knew how much she helped me in my early days of cross dressing. Before I outgrew her, I took advantage of wearing her fashion wardrobe, not to mention her makeup too. Much pressure to hide to be sure because if I was discovered, intensive therapy or worse would be in my future.

Also very early on, I ran to places I thought I would be safe. I hid a collection of clothes and makeup in the woods beside our house in the country. In my own world, I could escape my brother and family and briefly enjoy my small attempt at gender freedom. On other very rare occasions, when my family was not home, I escaped to the bathroom and applied my clothes and makeup which was an ideal time to see myself in the full-length mirror in the hallway.   

As I grew older and my male life became more complex, running and hiding became much more difficult. Plus, I had so much more to lose in my life if I was discovered. The more I ran from my issues, the more pressure I faced. What happened was, after I was freed from the restrictions of my military service, I was able to run harder hoping to free my gender issues even better. I changed jobs and locations frequently trying to outrun my life and for the most part was more miserable than ever before. I moved my small family to the suburbs of New York City, then back again to my native Ohio. Along the way, we lived in an old farmhouse in rural Southern Ohio and back again to urban areas such as Columbus, Ohio.

Sadly, it took me many years to understand all the running and hiding was doing me no good. The problem was inside me and could not be out-ran and was mentally exhausting.  Once I learned the solution to my problems were closer than I thought, my journey to transgender womanhood became clearer but in many ways no easier. I still needed to strip back all the layers of femininity and do my best to cross the gender border. I think now, the communications I had with the world as a novice transgender woman were the most difficult part of the journey. I needed time and effort to overcome the fear I had with looking another women in the eye when we spoke. For the most part, I just wanted to run and hide. 

Every time I did not run, I developed more confidence in myself. In other words, with the help of other cis-women friends I had, I found and embraced my own transgender womanhood. No longer was I stuck in an old male life I never really wanted regardless of all the privileges I had accumulated from just being older and white. 

Running and hiding just became too exhausting and demanding to continue with it. I finally gave into the pressure and began to live in my truth. What took me so long. I still wonder. My male life just wasn't so much fun and successful to continue. I consider myself one of the fortunate humans to escape the bonds my gender roots had confined me with.    

It is NOT a Choice

Image from Alexander Grey 
on UnSplash

I still get aggravated when someone says being transgender is a choice.

Realistically, why would I have ever chosen to live the life I am living. Would I have made the choice to give up everything I worked so hard to achieve just to put on a dress, makeup and heels and attempt to live a feminine life. All the material benefits I had acquired as part of my life as a white male privileges disappeared for good, if I wanted them to to or not.

Suddenly, I learned the hard way what it was like to have my personal security threatened as well as being mansplained when I attempted to insert my feelings on a topic I knew quite a bit about. Quickly I discovered many examples. I nearly found out the hard way, if I dressed too provocatively at a mixer, I would be cornered and harassed by an over bearing transvestite admirer. In an instant, I learned how it would be to be a helpless woman being overwhelmed by a much larger man. Not a pleasant experience and it was not all of my lessons. One night when I was blissfully minding my own business on a dark city sidewalk, I was approached by two sketchy men wanting a handout. Fortunately, I still had a lone five dollar bill for them and they went on their way. From then on my new feminine common sense began to grow and I started to develop the gender protective sense all women acquire as part of their life experiences.

None of what I was experiencing was a choice and not part of me being validating  myself as a woman. All I needed to know was I had no choice but to follow my path if I was able to look myself in the mirror and know I was doing the right thing. Coupled with the natural feelings I was experiencing, my supposed choice was made. 

I knew over a span of time, I would learn to deal with being mansplained was something I just had to deal with as a transgender woman. I will never forget the day I had to sit in a tow truck and be subjected to being bored when the driver was telling me how the truck worked. Finally, I gave him my best blond act until he finished all his rock bottom explanations. On one of my few dates with men, quickly I found I knew nothing about subjects such as sports and politics.

Why would I choose to be something as difficult as being a woman? My entire life became dedicated to proving the world wrong. I could carve out and experience a new life as a transgender woman and thrive. But again, I needed to prove all the naysayers wrong. The only natural feminine attribute I started with was my brain. Which for some reason, kept telling me I was doing life completely wrong because I was living it as a male instead of my more natural female. Finally, all the pressure to change and all the stress to explore the world as a trans woman. I was living in a world of alternate facts which was increasingly too complex to handle. I came to the point where I felt as an impostor when I went out of the house as a man. Can you imagine that? Feeling as an impostor when you attempt to live as your birth gender. It happened to me.

All the process proved to an outsider is gender issues are not a choice. During the process none of us understands, we are born into system we never asked for. The path is often a bumpy one with plenty of curves and stop signs. We have to wait our turn before we move on. 

For any number of reasons, the true number of transgender women and trans men may never be known. One thing is for sure, there are many more hidden transgender individuals waiting to take their turn and enter the world. Regardless of all the negative publicity we receive, transgender people have been around forever and will remain a part of the human experience. After all, we don't have a choice.

Did I Get it Right?

Out to eat with my wife Liz on left. 

I make no secret of the amount of major moves I needed to make to how I arrived to live my life as a transgender woman. Now at my advanced age of seventy four, I wonder if did I get it right.

Of course like most of you, I needed to give up much more than my unusual white male privileges to transition. Along the way, there were marriages/ spouses, friends, family and job losses to deal with. In other words, many sacrifices to make to follow my gender path. In other ways, destiny and years enabled me to transition to a feminine life. My one big deterrent was my relationship with my second wife who in no uncertain terms was telling me she did not want to live with another woman. In fact she made it abundantly clear she didn't like my woman self at all. Except when she needed help with her make up. What could I say? She was correct when she said she didn't sign up for all the gender issues she was now dealing with in our marriage. 

Most of you know she died suddenly from a massive heart attack. The tragedy freed me up to do my own thing. My own thing turned out to be I quickly turned to my own woman for comfort. I discovered almost immediately, I got it right as I was having the time of my life as I explored a new world as an out transgender woman. 

I also found I got it right when I discovered other women in the world who would accept me without having any knowledge of my old male past. When I did, I was able to really begin to live a new life of my dreams. I also did it right on how I was able to raise my daughter who ended up being one of my biggest supporters to this day. However, I didn't get it right with my brother and his in-laws who roundly rejected me. Sadly, by this time, most all of my very few real friends had passed away so coming out to many people was not a problem. 

So, by waiting so long to complete my male to female gender transition worked out right to me plus, even though I was not enjoying my old male life anymore, I still took advantage of the male privileges I would lose. It finally got to the point it was ridiculous to continue a life anymore split between the two major binary genders. The stress and tension became too much for my mental health to sustain and I tried alcohol to solve my gender problems.

I did it right and stopped drinking as much as I did before I permanently injured my body and when I moved to Cincinnati to live with my future wife Liz. Liz encouraged me to permanently leave my male life behind and live fulltime as a woman with her when she told me she never had seen any male in me at all. Even when I was trying to be.

Finally, I really did it right when I was medically cleared to begin taking gender affirming hormones. My body accepted the changes easily and I loved them. So all in all, I did it right when I decided to transition into a full time transgender woman. Destiny was leading the way the whole time and the only mistake I made was when I tried to get in it's way.

  

 

Life in Her World

Image from the Jessie Hart
Archives

Once I was preparing to live as a transgender woman, I needed to figure out what to do with my new life. . 

As it turned out, even though I had worked for years to figure out my ultimate gender puzzle, I found I still had a long way to go. When everything ceased to be in my mind and into the world, I faced the formidable task of rebuilding my life as a trans woman and leaving my male past behind. The first major problem came from my old male self accepting any of the idea at all. He kept reminding me of all the risks I would be taking if I transitioned. What would happen to my family, friends and employment if I entered my new exciting world. What I did for the longest time was attempt to live with one foot in one gender and one foot in another. Of course, my less than wonderful idea did not work and the pressure to move into her world fulltime became unbearable. I finally realized I did not have a choice and  I just had to complete my transition. I emphasize I had no choice because some transphobic individuals think I did. I would like them to live just a small time in a transgender life to permanently change their minds.

Another problem I had was the longer I lived in my new trans life, the more routine it became.  I found myself slipping back into my old male bad habits which were long gone. When my white, male privileges disappeared, I had no where to turn when life turned the tables on me. A primary example came on the occasions when my personal security was threatened as a novice transgender woman just learning the world. I discovered I could not just bluster or bluff away problematic situations which arose in the world. In many situations, like every other woman,  I needed to work hard to distance myself from the problem and try to learn from it.  Every time I slipped back into male mode, I was rudely reminded of what I did and quickly adjusted.  

Just moving around became a priority for me. I needed to unlearn the male walk and talk and learn to try to flow like a woman. I practiced everytime I could until I thought I had achieved a basic successful walk so I would  not look like a line backer in a dress. The whole process became easier when I finally realized I needed to put my male self away and adopt the feminine one forever. Without totally knowing it, I had moved away from my cross dressing days into a life in her world as a transgender woman. As far as talking was involved in the process, I write about the feminine art of communication often. As a male my habit of frontal aggression needed to go away as I found myself in a world dominated by passive aggression. All too often, I suffered the pain of claw marks on my back when I thought I knew what another woman was thinking or doing. Instead of making the first move in situations, I learned to lay back and let the other woman make the first move and then go from there.

Life in her world then became a question of how confident I had become. I came to realize even though another woman realized my path was different than hers, I still could be accepted as an equal. When I reached this moment of confidence, my life changed forever and I knew I could live the life I always dreamed of. In her world where I always belonged. 

In order to do so, I needed to finally trust my inner feminine soul to take over and run my life. She did a wonderful job since she had waited so long to do it. I was able to become a well rounded person in her world.

Mansplaining a Trans Girl

Woman being 
mansplained by Al Eimes
on Unsplash .

First, mansplaining to me is a highly insulting way to communicate with women and one I tried my best not to do before I transitioned into the world of a transgender woman. 

In fact I think I went out of the way to not mansplain anything to the women I worked and lived around. I hope now it wasn't noticeable and I was coming off as dismissal. Regardless, I did my best until I was admitted behind the gender curtain and was able to see how the female half lived. 

The problem was, I took so many years to get to the point of being allowed to look behind the curtain and play in the girl's sandbox. So I never quite understood what the mansplaining fuss was all about, until it slapped me one night in a regular venue I was accepted in. What happened was somehow I became part of a small group of men discussing a topic I knew a lot about, like sports. I was still new to the system and tried to interject my thoughts into the conversation. Just as I would have as my male self. To my surprise, I was rudely ignored by the men and I quickly left and went on my way. The whole process was another of my life changing moments when I was transitioning. 

I didn't know what I was expecting since I had seen mansplaining all my life from other men around me when they interacted with women. Why would I be any different? Well, I wasn't and the better my presentation as a transgender woman became, the more I was talked down to. It was like I had lost most of my intelligence and all my life time experiences in addition to other male privileges. 

Quickly I learned to play the game of being a dumb blond, which I was most of the time back in those days. A prime example came one night when my car broke down and I had to call a tow truck. As luck would have it, a well meaning policeman showed up to help and between the driver and the cop figured out the best route to get my car home without even asking me. I was infuriated until the whole evening declined even farther when the tow driver started to explain to me how his wrecker worked. on the ride back Finally, I relaxed and started to ask him questions about what his wife packed him for dinner and why were wheels round. (Just kidding.) But I tried to make the questions of my status as a woman for him which was obviously very low. 

Maybe I should have been happy I presented so well that I lost a main part of myself forever. I learned how women are really treated and prepared myself for other gender lessons. The main one I write about often is the loss of personal security I witnessed up close and personal when I transitioned. I learned to park in the most well lit and safest places I could with the shortest walk to wherever I was going, to name one important point. For the first time in my life, I was the prey when I was out in the public's eye and it was quite the change.

Slowly but surely on the rare occasions I needed to communicate with a man, I learned to draw from my personal experiences and understand where he was coming from. I waited for him to come to me and interject my ideas when I could as a transgender woman. By doing so, I was able to build my confidence back up in public. 

Today when I am mansplained, I take it with a grain of salt because I know there are plenty of women who reverse the process with their communication with men. I remember several nights when I was fine with talking to the woman in a couple I didn't know and having it all change in a flash when he started to show any interest at all in me. There was no womansplaining going on as I instantly knew where I stood. It also never took me long to understand all the non-verbal cues women use to signal each other. 

 It is one of the reasons both binary genders have such a difficult time of communicating. Upper level understanding of the genders is one of the rare benefits of being transgender and should be embraced. When you can do it, you truly have the chance to advance as a human. 

Transgender Pressure Cooker

Image from Jeshoots.com. 

When someone writes or says something about me being a transgender woman being a choice, I have to laugh. 

I'm sure those of you who have gone through life the way I have with gender issues would agree. Primarily because we have given up so much to cross the gender frontier. Primarily, I am referring to losing family, spouses, employment and gender privileges to transition. Just losing male privileges alone is a major issue. Very quickly I discovered I lost a portion of my intelligence when by accident I became involved in a conversation with several men. I found I was not respected in their world until I finally got tired of being ignored and left the group. Then I began to not speak much until I was spoken to until I began to gain more confidence. 

When I began to be successful, the pressure to be even better as a transgender woman started to increase. For several reasons, my fragile mental health became worse as I started to try to live a life situated between the two main primary genders. In other words, I was stuck in a gender fluid universe I did not want to be in. Living one day as a man and the next as a transgender woman, nearly killed me.  It became so bad I needed to make a conscious effort daily determining what gender I was going to be that day. How was I walking and talking were just a few of the many gender considerations I was going through as the pressure kept increasing. 

All of a sudden, I was able to establish a whole new identity as a trans woman. I was talking to other women and building a small circle of friends which taught me so much about the world I so much wanted to be a part of. I kept going because the process became so natural to me and very soon the main source of pressure came from having to return to what was left of my male life. Even thinking about going back caused me stress and added pressure. 

Finally, I knew I had no way around it and never really had a choice with my life. As a gender therapist told me so many years ago, there ultimately would be no choice for me if I was a transgender woman. Sadly I did not believe her and stubbornly went on to fight a losing gender battle for years before I gave up and faced my gender reality. By doing so, I tried very self destructive measures including suicide and excessive alcohol abuse before I started to live my truth. 

I had no choice and needed to give up all the pressure I felt to transition into a feminine world before it all literally killed me. Thank goodness for all the friends and family I had who helped me through my difficult pressure packed days. The more good days I had with them led to my belief I could live my gender truth full time. Ultimately transitioning was similar to sliding down a hill towards a steep cliff for me. I had others around me who took the pressure off and made the landing a soft one.  

The Biggest Sacrifice?

 

Image compliments of Racquel.

When transgender women cross the gender border into a feminine world, we face losing many things. 

Naturally, we have to consider the three "F's" or Family, Friends and Finances. All major losses in our lives. In fact, they are so important I get a chuckle when someone says being trans is some sort of a choice. If indeed it was a choice to undertake such a radical life change, I would have certainly chosen an easier path. With easier sacrifices. 

In the early years of my life I was predictably naïve when I thought cross dressing in girls clothes was sacrificing just my male existence. It took me years of living, as well as accumulating white male privileges, to learn how much more I could lose. As far as the first two "F's" would go, I was fortunate in my results. I lost all contact with my only sibling, a brother but gained so much more through adding a bigger more accepting family through contacts such as my daughter and wife Liz. Thanks to women such as Kim, I was able to expand my friends into an accepting world of cis women who taught me so much about the life I wanted to pursue. I even had a close transgender woman friend (Racquel) who I would socialize with on a regular basis. Surprisingly, I found I had an easier time making friends as a trans woman than I ever did as a man.  In addition, Racquel and I had more than one interesting adventure at venues when rednecks played "Dude Looks Like a Lady" on the juke box eventually leading to the manager kicking us out that evening and not our bigoted tormenters. She is also the one who said I passed out of sheer willpower. 

As I progressed down my gender path to living more and more as a trans woman, I discovered more and more sacrifices I would have to make. One evening comes to mind when I was first coming out, somehow I found myself in a group of men. I found out quite early not to try to interact at all when I was ignored when I tried to talk and express my opinion. So much for maintaining my intelligence or any workable knowledge as a woman. One male privilege down to be sure but I found the biggest one was yet to come. 

The biggest privilege to lose was my access to personal security. I was always a fairly good sized man and could handle myself well enough to get by. The first time I encountered problems was when I was a cross dresser at a party of my friends in Columbus, Ohio. The attendees were normally very diverse and included anyone from transsexuals to lesbians to men who were cross dresser "admirers." One night I was cornered in my too short mini dress by a huge admirer and needed to be rescued by my highly disapproving wife. In an instant, the damage was done and I learned how easily it was for a woman to be overpowered and compromised by a much larger man. 

The other lesson I learned was the one I mentioned in yesterday's post. It happened when I left a gay venue cross dressed in my heels and hose and ran right into two men on a dark deserted city street. As I said, I was fortunate when I was panhandled for a five dollar bill and allowed to go on my way. These two happenings taught me valuable lessons on keeping myself safe in my new feminine world. All I was really doing was learning what cis-gender women grew up knowing their entire lives. 

So all in all, with a lot of help from the world and friends, my sacrifices turned out to be less severe than the process should have been. And, so worth it! 

 

Ode to Halloween

 

Halloween image from
the Jessie Hart Archive (Tom on
Left)

I have lived long enough to experience Halloween coming full circle.

Early in life I experienced the urge to wear a feminine costume but never had the courage to break out of my gender closet and do it. Plus I lived in such a small rural area, there weren't too many kids to go around and once you were pigeon holed into a certain category with your peer group you couldn't get out.  Examples included friends who were good or bad students as well as those who were always the outstanding athletes in the class. There was never any space for a stray boy who wanted to be a girl.

So I had a deeper reason never, ever express my feminine longings at all on Halloween. On top of all of that, I never saw any other boys who were dressed as girls. No cheerleaders, princesses or any of the stereotypes from the female world. The only time I can remember ever seeing a fellow male in drag or cross dressed was for selected festivals in high school. I was amazed at their male to female transformation. Plus I did hear the gossip concerning another guy in school I didn't really know who was dressed in his sister's clothes for his "costume" as the rumor went. I was so envious!

Once the years progressed and I naturally achieved more freedom to be my own person, I was able to pursue more courageous goals as far as Halloween went. I tentatively used the holiday to sneak out of my closet and explore. Could I dare make it in public as my feminine self. Very early I learned lessons I could take with me for years as I transitioned. I found if I dressed more conservatively at Halloween I indeed could have a chance to present well in the public's eye as a woman. As it turned out, all of this would be just the beginning of what I could learn on my ever rocky gender journey. 

Halloween made it possible for me to understand I could indeed live a life as my authentic feminine self. The only real problem came when I could only experience my terrifying yet exciting new life once a year. I was increasingly forced into the real world to learn my new gender lessons. All of which were made possible by Halloween.

Ironically, the more I learned from my initial experiences, the more I found the lessons would serve me well when I transitioned into a world ran primarily by women. If I could get other women to accept me, the better and easier I would have it. I also learned the hard way the process I would need to go through with men to attempt acceptance. Along the way, when I learned the better I presented at Halloween parties as a woman, the more of my male privileges were lost. Almost instantly, my old male friends began to leave me alone with the rest of the women. 

These days I have gone full circle with Halloween. It has served it's purpose of launching my journey down a path to be a full time transgender woman. So I don't have any need to go to any parties with elaborate costumes. I have done all of that and it is time to sit back and recognize Halloween for all the amazing experiences I was provided.

Mourning your Past

Image from the
Jessie Hart Archives

Is there ever a time when you miss your old gender self? 

Do you miss your old male privileges which seemingly gave you more rights?  Remember the old days when you survived with the myth of more intelligence and less mansplaining in any conversation with a man. While I remember the shock of my first times of interaction with a group of men who essentially were ignoring me, on the other hand I thought somehow I had arrived in the place I wanted to be. I was experiencing first hand the loss of the privilege's I had fought so hard to accumulate in a male world I didn't like. 

No matter how much you enjoy your new life as a transgender woman or trans man, possibly there could be times when you miss the good times? On my end, it is very rare when I miss the "good old days" which weren't so good. 

On a recent interview with a Veterans Life Insurance representative I experienced a brief glimpse into my past when I needed to explain my gender situation with the sales person. For the sake of insurance, since I have not undergone any gender realignment surgeries, I had to tell the person I was still biological a male,  even though I lived as a woman. Through the confusion, the only person who really suffered was my daughter who was rudely interrupted by an insurance call which referred to me as a "he". Since she has a transgender child and a is a fierce ally of the trans community, she was not happy. So I ended up calling the representative and asking what she was doing calling her at all. 

Other moments of surprise and a bit of shock occurred during the times when I had my personal safety challenged. The first time happened during a party I was attending in Columbus, Ohio with my second wife who was strongly opposed to the mini skirt I was wearing. Her fears for me materialized when during the party a huge cross dresser admirer cornered me in a narrow hallway. For the first time in my life, I was made to feel powerless about my body until I was rescued by my wife and he freed me. 

The second major time happened one night when I was leaving a late night urban gay venue on a lonely, dark street in Dayton, Ohio. As I clicked down the sidewalk in my high heels, I was suddenly approached by two men. Again I felt totally powerless and on the edge of panic. That night I was lucky when I was able to use my last five dollar bill and they went away to my relief. From then on, I learned my lesson and always tried to park in close well lit parking lots. The old days of just having more personal security were over but I knew they had to go.

Overall I looked at the whole privilege changing time as a challenge and one I needed to conquer. Through it all, I had no time or will power to mourn any of my past. The only time I have twinges is during football season when I remember a few of the intense past experiences I went through when my second wife (a big fan too) attended all the biggest The Ohio State Buckeyes football games. Admittedly most  were memorable times I would not trade like the birth of my daughter which I was present for. 

Being part of the two binary genders has made me an overall better person. Mourning was just a part of my life as is it is a part of any other life. I view the process as a plus as I tried hard to leave my old male past behind and begin a new life as a transgender woman.    

Gender Side Effects

 

Liz on Left from the 
Jessie Hart Archives

When a human being attempts to cross the gender frontier to live a life as their authentic selves, they naturally undergo many side effects. 

Perhaps the biggest side effect is just having to live as the gender you had always dreamed of living. Quickly you find the grass isn't always greener when you transition. My primary examples include when I suddenly lost a part of my intelligence when I started my life as a transgender woman and when I found out the hard way my personal security most certainly wasn't the same. The entire process most certainly was an eye opening experience. All of a sudden, I was more than the "pretty, pretty princess" my wife called me, I was discovering how a woman really lived. 

Other side effects came when I began to live more and more as my feminine self. Gender discoveries were coming fast and furious and were often as terrifying as they were exciting. My male self did not want to give up all the white male privileges he had won in the world. It seemed just the time he could have been situated to enjoy the positives of his labors, it was all taken away because he decided to live as a transgender woman. Side effects for my male self were all negative. 

When I was able to step back and view the entire gender trnasition experience as a whole, the biggest side effect was the entire process felt so natural. When I was having any of the self doubts concerning moving forward in my transition, deep down inside my feminine soul told me to just keep going and everything would be alright. I just needed to learn my own way how difficult the process would be. It seemed every layer of womanhood I learned would just be scratching the surface of what I needed to learn. How was I ever going to be able communicate with the world as my new self and would I ever be accepted to being able to play in the girl's sandbox as an equal. Just two of the burning questions I was facing day to day as I considered reaching for my dream.

Another huge side effect was the time it was taking me to move forward in the world. For every step forward I felt good about, the were two steps back I needed to worry about. Examples included, what was I going to do about a very non approving spouse and how could I ever live without the fairly high paying job I had worked so hard to obtain. As it turned out, biding my time while I learned more about what being a woman was all about turned out to be a good side effect because I was more prepared when the time came to actually begin my life as a full time transgender woman. By the time my transition fully happened, I don't think I had ever prepared better for anything in my life and I was in my early sixties at the time.

Now I can safely say, the final side effect for me was a positive experience. By transitioning I have been able to live out a lifetime dream and never looked back.