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.