Teamwork makes the Dreamwork as a Trans Woman

Girls Night Out, I am on the bottom far left.

Similar to so many other cross dressers or novice transgender women I have heard from, they dream of enlisting a cis-woman to aid in their appearance.

I was included in having a similar fantasy. All the way to the point of begging my fiancé to completely dress me as a woman if I rented an out of the way motel room for privacy. Sadly, for me, she agreed and she did do her best to dress me as the woman of my dreams.  I say sadly for two reasons. The first being I did not see that much of an improvement over what I was able to do for myself since by that time I had practiced in the mirror myself for years. The second reason I say sadly came years later when I was facing being drafted into the military and being sent off to Vietnam. At the time she pressed me to tell the draft board I was gay to be deferred from going. Even though I didn't and don't have anything against the gay community, I knew I wasn't gay and wasn't going to lie to escape military service. The end result was she ended up breaking the engagement when I went off to the Army which I learned later was the best thing which could have happened in my life to that point.

As you can tell, I didn't have anyone to enable my teamwork work from any sort of a dream work. One of the problems I was having was working my way through exactly what my gender dream. I was still years away from facing my reality of being a transgender woman. So I suffered alone with my gender dysphoria before I was able to break out of my gender closet. It wasn't until much later when I discovered the beneficial beauty of having cis-woman friends who accepted the new transgender me for who I was. When I let it happen, my dreamwork began to flourish. 

Quickly I began to learn the world from the aspect of being an invited participant in girls' nights out. I was invited along to several different groups of women. All the way from married women to younger girls still in the dating pool. Neither mattered to me because I was learning so much about living a women's life with no men around. Even though when I went out with the younger group, I found how it was to be the decidedly older and less attractive woman in the group. Again, it didn't matter as I flattered and happy to be invited to begin with. 

This was an exciting time of my life when all of a sudden my dream of living a life of a fulltime transgender woman seemed to be so reachable. Being included and  embraced by the women I met was the difference. We went to birthday dinners together, went to parties with each other and of course used the rest room together, All of which turned into the ultimate bonding experience as a new trans woman.

Was I scared? Sure I was but the embraces I received within the group quickly put me at ease so I could enjoy myself and gain confidence in the new feminine person I was creating. It turned out I did not have much creating to do because once my feminine soul hit the world, she flourished. 

Even still, being in a women's world and experiencing their teamwork, did make the dream work happen for me. I was a better person for it once I left my gender dysphoria behind. My mental health improved as well as everything else in my life once I left my male self behind.

Opportunity Knocks

 

Civil War Cemetery image
from the Jessie Hart Archives
 

In my life I have found several really rare times where true opportunity actually knocked on my door. 

As I indicated, the situations were exceedingly rare and required split second decisions on how I was going to proceed. Possibly the first main one happened when I went with the "A" list trans women from the cross dresser - transgender mixer I was at in Cleveland. It was the night I gathered my courage, put on my big girl panties and was able to enjoy a professional makeover at the mixer. The result was I looked better than I ever had in my life and really wanted to claim my spot with the other impossibly feminine women in the room who were planning to continue the meeting with going to gay venues afterwards. At the second venue we went to, for the first time in my life as a woman I was approached by a good looking man who wanted to socialize. Since I was in a city I knew nothing about and with acquaintances who were about to call a taxi and leave, I decided to turn his advances down and leave. I often wonder what would have happened if I had stayed. What sort of opportunity if any, did I miss?

 Most likely, the second opportunity I did take advantage of was when suddenly I decided I had had enough of cross dressing and wanted to follow my gender instincts even further. It was the night I was determined to go out and blend in with a group of young professional women at an upscale bar/restaurant I had frequented several times as my male self. More than anything else, I wanted to see if I could blend in with the group as a transgender woman and enjoy myself. Perhaps what I remember most about the evening was how scared I was as I waited in the parking lot constantly checking my hair and makeup before I gathered the courage to go into the venue. As it turned out, opportunity did knock that night. I enjoyed myself after I could take a normal breath again and I knew my life as a casual cross dresser was gone forever. I needed new horizons to conquer as a novice transgender woman.

As I settled into attempting to find my way as a trans woman in the world, I tried to try different venues and situations to deal with. Some were successful, some were not. The ones which I can remember the most were the times I tested going to more or less red-neck country venues. I quickly discovered I wasn't welcome and moved on quickly but not before the cops were called on me a couple of times. No opportunity to succeed in those places for sure and I never went back.

Perhaps the biggest opportunity which came knocking at my door was when I had the chance to begin gender affirming hormones or HRT. At my age of sixty, I wanted to make sure I wasn't going to harm myself, so I took the proper precautions and sought out a doctor to prescribe the medications I had waited for so long. Fortunately for me my health proved not to be an issue and I was given minimum dosages to get me started. Seemingly, my body took to the hormones like I always should have been on them and new changes started almost immediately. In no time at all, I was moved up to a higher dosage and my new changes took over my body. So much so, I needed to move up my transition timetable when my hair started to take off and grow along with my softening skin and protruding breasts. 

Then, the most unexpected opportunity happened when I met my current wife Liz on line nearly fourteen years ago. At my age and transgender history, I was prepared to spend the rest of my life alone and especially never expected to ever be married again. Opportunity was telling me to never say never and here I am.

I have a very hard head however and many times opportunity had to knock loudly to get my attention. Often because I was stuck with life changing conditions where I could lose everything. I tried to fall back on my inner self and hope for the best and finally I let her lead me the right direction. 

Take Your Pleasure Seriously

 

Ohio River image from the
Jessie Hart archives. 

For a gender dysphoric person, the scale seems to be balanced against experiencing any gender euphoria.

 In my case, destiny allowed just enough gender euphoria for me to continue down my gender journey. As I questioned what I was doing, the "why" of it never really came into question. I just knew deep down I was on a process I could not control. It would control me. Deep down inside, regardless of any doubts I may have had dissolved when I felt so natural when I was dressed as a girl. In other words, I was home when I was away from my unwanted heavy male self. 

Still I persisted and tried to find my way in the male universe, I was taking my pleasure seriously when I was dressed head to toe as a woman. I found following one dream (feminine) didn't mean giving up on the other (masculine.) I often wonder, if there was any help available to me back in the pre-internet dark ages would I have had the courage to seek it out. One problem was back in those days we who existed with gender issues were still considered to be mentally ill. Which I knew I wasn't.

The gender unrest I lived through and with was to continue until much later in life. Nearly a half a century to be exact, I gave up any hope of ever returning to a male life and never looked back. Riding a wave of gender euphoria was something I had never experienced before. Living as my authentic self was amazing and even though my male self was still fighting to be recognized. He was to be denied and my life went full circle back to the earliest days of wondering what gender I really was.

By going full circle, I had a lot of ground to cover. In many ways, the world caught up with me. I was able to follow the progression of a term which would describe me and in a very small way enabled me to be a part of a transgender community. Along the way many things changed. Primarily in the terminology which began with what was transgender anyhow and went all the way to the LGBT label which has grown these days to include other letters which includes other communities. Including gender fluid people which on occasion, described how I perceived myself all those years ago. 

During my full circle journey, I learned to take my pleasure seriously. Different than most transgender women and one I don't necessarily recommend, I learned the so called "ropes" of being a single woman (trans or not) in alcohol serving venues. All of the sudden, I found myself in situations where I was the single woman. The positive side of taking my pleasure seriously was when I discovered a small community I could thrive in. The negative side came when I was approached by intoxicated men not in control of themselves. Early on, when I needed some sort of protection, I used my cell phone. Making a big show of acting as if I was talking to another person on the phone who was coming to join me and fill the empty seat beside me. Of course after I gained my small group of lesbian friends, I was nearly completely insulated from the world of men. Also my ideas of sexuality were determined for good. I had way more interaction with women than I ever had as a guy.

Along the way, my new found gender euphoria as I learned to live as a transgender woman began to put my unwanted male life behind me, I had managed to live through the down points in my life and come full circle into a new day. I don't know if the ups have ever equaled the downs but at the least I was never bored.  

Opening Transgender Doors

Image from Nathan Wright 
on UnSplash

What is the old saying, "When one door closes, another one opens." I think the saying is especially appropriate for transgender women or trans men.

Along the way, I have documented several substantial times when I slammed doors during my past and opened new doors. 

Probably the first time I closed a door was when I was going out with a certain set of party friends who ranged from cross dressers to transsexuals who were planning their genital realignment surgeries. I wasn't very interested so much in the cross dressers but on the other hand, I was very interested in the women who were going "all the way." I wondered if I could ever slam the door on the male life I had fought to live and open a new door into a feminine world. 

Luckily I was able to see different sides of the gender coin so to speak. One friend in particular was a firefighter in Columbus, Ohio who was gorgeous and near retirement. So she had the financial risk of a gender transition covered as did the other main transsexual woman I knew at the time. She also was gorgeous and had a very secure job as an electrical engineer. She was so good at living a woman's life, she regularly went on snow skiing trips, spending whole weeks as her authentic self. So, as you can tell, I had lofty role models to try to live up to. I knew they would be difficult to match up to as far as appearance and income plus neither one had a spouse to deal with. I loved my spouse very much and wasn't sure I was able to close the door on my relationship with her. 

Even still, I continued to observe and learn as well as set out to open my own transgender doors. It just took me longer than others to find a path of my own. I know all too many of our gender journey's are similar yet so far apart. It is difficult to leave the first door in our closet and find the other doors in the darkness. Once I was able to find the light and it wasn't the train at the end of the tunnel, I was able to progress quite nicely but not without trepidations. Of course I still had to deal with the usual problems transgender women and men have to deal with when they transition and close the big door. Sometimes closing the door is the easy part compared to opening the doors to different living situations with family, friends and finances. 

I think too many potential transgender folk believe the transition itself will cause the life problems to go away and they haven't thought enough about the all the situations they would have to face now when spouses and/or families want to leave them behind. Not to mention the prospect of losing long term employment and friends. All of the process led to opening very heavy doors and not having much of an idea what the future held. 

I was fortunate when I finally had the courage to open my final transgender doors and face the world. As I did, I could look back at all the times I was petrified to try a new life as a transgender woman. Every time I was so scared it seemed I made it OK which felt so natural and gave me confidence to move forward and look for new challenges. I don't think I ever forgot the two early gender role models I had in Columbus, Ohio so many years before but similar to my male life, I was able to carve out my new life as a fulltime transgender woman so different from theirs.

Even still, I have my doors to open as I face a challenging future with end of life issues. I am still paranoid concerning facing the problems associated with nursing care or assisted living. It will be quite the journey as I face the final door we all have to open and see what is on the other side.

Nonsense?

 

Recently I received this comment from Kendra referring to one of my political posts. Since I am a firm believer in  equal time, here is the comment:

"I am sorry you believe that nonsense about Trump. I am also TG, and I feel none of what you are speaking of. We conservatives are actually a loving caring group of people. Yes, many don't understand the lifestyle, but no one wants to hurt us. Please do not fear us."

Thanks for the comment and the first fact I would like to counter with is I do not fear conservatives and I have often thought of voting for Liz Cheney if she had ever made it on the ballot. To make it clear, I do not consider tRumpt to be a conservative. I consider him to be a threat to our country's security and the basic rights to all citizens. 

Now, let's add in tRumpt calling veterans (which I am one of) losers, bragging about reversing basic women's rights to their own bodies and increasing the national debt four times while he was in office while at the same time pushing through tax breaks for the very wealthy. Plus the biggest one of all, his threat to be a dictator from day one after trying to overthrow the government before (Jan 6th).

Kendra, what I really fear are the transgender citizens and allies who don't realize tRumpt and the paid off SCOTUS is coming after your basic rights. Perhaps you haven't heard of the 2025 blueprint. If you haven't I suggest you research it yourself. 

What I also fear is my hopes for my transgender grandchild's life in the future long after I am gone. At the least I want my grandchild to use the rest room of their choice which is being challenged now in my native Ohio by (yes) a conservative majority in the state legislature. I want them to know I tried my best in any small way to help the transgender and LGBTQ cause. 

I know sometimes I may sound as if I am some sort of a radical left leaning person but I value the counterpoints of having conservatives in the system and I used to have lively discussions when I was in the Army when I was the only once saying at the least Nixon was a crook. 

My deepest desire is tRumpt is never given a chance to advance his agenda against the the country in general and the transgender community in particular. It doesn't take someone in a paygrade higher than mine to recognize that after trans people are erased the bigots will come after the remainder of the gay and lesbian community. 

So Kendra, yes I deeply believe the "nonsense" about tRumpt. 

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.

Being Afraid to Try

 

Image from Jas Min on UnSplash

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

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

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

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

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

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

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

 

Lesbian Bars

Image from the
Jessie Hart 
Archives.

When I was first exploring the world as a novice transgender woman, one of the first big discoveries I made was the male gay bar scene was not for me. 

I initially thought going to a gay bar was a safe place to be. I found I was safe, to the point of not being threatened but on the other hand I did not anticipate being ignored to the point of being discriminated against. Since I knew the odds of anyone hitting on me would be very low, again I was lonely all the way to the point of being ignored at the bar when I tried to order a drink.  Also, I disliked being treated like a drag queen on nights when there was a show. Within a short period of time, I grew tired of the experience and looked for other outlets to explore.  

About that time, I became aware of several new lesbian bars which had opened around the Dayton, Ohio area and wondered how my acceptance would be at them. Since my sexuality had never changed from liking women, I felt more comfortable in their company and wanted to see if they accepted me at all. Not to be "picked up" so to speak but to be treated on a friendly basis. Initially, I knew of three lesbian bars of which I tried to go to two. 

The first one I tried did not accept me at all. It was a very butch dominated bar where I got in trouble for playing Shania Twains "Man, I feel Like a Woman." The lesbians huddled around the small bar did not see the humor in my choice of music. Even though I wasn't welcome, I still persisted on going back just because I was so stubborn. On the other hand the second lesbian bar I went to was a completely different experience. They were friendly to me and I felt relaxed and welcome. Plus I was surprised when I discovered my male self actually knew one of the bartenders. Her and her wife were regulars at my restaurant. 

As it turned out, I had many exciting experiences there starting with how I presented myself.  Quickly I assumed the role of a "lipstick lesbian" in my boots, tight padded jeans and blond shoulder length wig. One night I presented so well, a "super butch' (very masculine) woman approached me to sing karaoke with her. She would not take no for an answer so I joined her along with her cowboy hat for a terrible duet. Since I am a terrible singer. When I finished, my singing partner said she was surprised my voice was deeper than hers as I began to plot my escape. While she took off to the restroom, I took off to pay my bar tab and left and I never saw her again. I know my friend behind the bar got a kick out of my whole experience. 

One night I am still sad I missed was when the bar scheduled a few exotic dancers to come in and entertain. The small venue was packed as everyone eagerly awaited the show and one of the other patrons actually bought me a beer and said she ought to take me home with her. Even though I was flattered, at that time I still had a wife to go home to and time was running short. I could not stay until the exotic dancers made it, so at the least I saved the tip money I was going to use. It was to be the only time in my life I would get the chance to experience how a group of women act around dancers.  

I was saddened when the bar closed and I had fewer venues to go to but it was a time of great discovery for me anyhow. My new small circle of cis-women friends were lesbians. The fun started when I began to receive invites to come along to monthly lesbian only mixers at different Dayton, Ohio venues. Some were straight while others were gay which made going even more exciting. One night, one of my friends even asked me to approach another person at the mixer for her to see if she was with someone else which marked the first and last time I was ever a "wing person" for another woman. 

Probably, the biggest lesson I learned about the lesbian community was the different layers of people from "Baby Dykes" to "Lipstick Lesbians" all the way to "Butches and Super Butches." I found for the most part I fit in except for one night at a woman's Valentines' Dance years ago when a bigoted TERF attacked me about being at the dance at all. At the time, my future wife Liz was part of a Cincinnati lesbian social group which I tried to join also. When I was turned down, Liz left the group. 

As you can tell, I owe quite a bit to lesbians and their bars which sadly have disappeared in many areas. I know of two still left in my local Cincinnati area but there could be more I have not heard of since we don't get out much anymore. I just know the venues I went to in place of gay bars were a welcome relief to my acceptance as a transgender woman. When I combined them with all the straight venues I had become an accepted regular in, my new life was off to a good start. 

Ownership, Skeletons and Politics?

 

My daughter's favorite saying used to be something to the fact if you have skeleton's in the closet you better make them dance. Which could describe many politicians in Washington DC.

This post however is not another rant on my part about politics. If you follow me at all you know I am solidly behind the Biden-Harris ticket and believe tRumpt and his cohorts want to erase transgender people everywhere. As well as do away with our democracy. But, as I said, this post is not about politics, it's about my life. 

In my case, I spent most of my life trying to change the inevitable. I was transgender and should just relax and make the best of the situation I found myself in. By cross dressing my life away, the only positive I can come up with is all the practice I put into the art of feminine makeup and fashion. It wasn't until I left the mirror and started exploring the world, did I begin to own it. The whole process turned out to be a blur and actually happened faster than I dreamed it would. In other words, by interacting as a transgender woman in public, I was teaching the skeletons in my closet to dance. 

The dance moves became more and more intense when the public wanted to invade my little private world and know more about me. First of all, when I finally moved from the easy clothing stores in the malls I used to shop at and into food venues where I would stop to eat. Then I found myself needing to communicate with servers and bartenders one on one as I was scared to death. At first I tried to mimic the range and tones of the women I was speaking with until I found I could take advantage of feminine vocal lessons at my local Veterans' Administration hospital. Slowly, I gained enough confidence to get by in the world. I was coming to realize I could not change who I truly was, so I better learn to know her better. When I did, I enjoyed the person she was, My feminine inner soul went way past just trying to look good in the mirror and do a better job with my makeup and fashion. I found I could just let her go and I could set back for a change, watch my skeletons dance and enjoy the show. For the first time in my life I did not have to feel guilty about the person I was becoming.

In addition to having less guilt, I was having the time of my life. For the first time, I was making new friends who had no connection at all with my old male self. My small core group of mainly lesbian women friends taught me more about owning who I was than they ever knew. I was validated as a transgender woman through them mainly because they saw me as me. The freedom was remarkable. 

Perhaps I could say I transitioned to my authentic self  not so much because of my friends but on the other hand, I started to own my life and live it with my friends. I was teaching my skeletons all new dances when I let them out of the closet. As always my old male self was resisting losing his grip and it took my wife Liz to send him away. When we first met, Liz barely knew what was left of my former self and she told me she never saw anything remotely male about me. That was it and from then on I went all out to own who I really was. 

See, I told you this was not going to be a political post, Now if you will excuse me, my skeletons are dancing for the public to see.