They Took my Cross Dressing Stash

Image Courtesy Anete Lusina 
on Unsplash

When I enlisted in the military rather than face being drafted during the Vietnam War era I ended up having an extra five months or so before I needed to report for basic training. This was back in the early 1970's. At that time also, I was working on a radio station near where I graduated college from in Urbana, Ohio. And, I ended up finding a job where a friend of mine was working in Bowling Green, Ohio. If you are not familiar, Bowling Green is the home of a fairly sizeable university, so there was a market for progressive rock radio as it was known back in those days. In order to take the job, I had to only move approximately one hundred miles north to Bowling Green. In the meantime, I found an apartment to live in with two other college students. I was up front with everyone about my having to leave in a couple months because of my date with Uncle Sam. 

The only problem I had was what was I going to go about my small but growing wardrobe /makeup of women's clothing.  Since I had my own room in the apartment so the issue became smuggling my "stash" out of my parents house and into it's new home in Bowling Green. I always say "Where there is a will, there is a way" and I was somehow able to accomplish doing the move without anyone noticing. Once I moved into my new apartment I was fairly careful to make sure I didn't leave out any of my cross dressing accessories for anyone to see. My plan worked well and when the college holiday break approached I planned to be able to pursue my past time in peace. All my other apartment dwellers were college students and they planned to be gone for nearly a month or so around the holiday season. 

One night, unannounced another guy who didn't go home for the holiday's showed up at the apartment. A night I had planned for myself to shave my legs, slide on my panty hose, dress, makeup and wig and enjoy the evening. As the evening progressed with this guy and after a few beers, I started to wonder if he would be totally degusted if I dressed in front of him. I finally decided to try it, secretly hoping he would find me so attractive he would want to take me out to one of the college bars downtown. After making sure he knew where the beer was, I slipped away to get ready. After I got my courage up and finished shaving my legs I went searching for my "stash" and discovered to my horror, most of it was gone. So much for any planned seductions I had planned. 

I never did find out which of my apartment "friends" or their girlfriends stole my cross dressing stash. The closest idea I could come up with was someone got into my room when I was home a couple days for Christmas. When everyone returned from their breaks I didn't have enough courage to confront the group about what happened. I should have because my mind set at that point in time was what was the worst that could happen? In a month I would be gone to the Army anyway. It was just another one of those "what if" moments in my life, 

What if I had the courage to cross dress as a woman in front of a stranger for the first time in my life and what if he liked it. I will never know because they took my cross dressing stash.    

Undying Admiration

Photo from Davide Ragusa 
on UnSplash

 Or should I say the opposite, dying admiration. On the rare occasion I visit a cemetery., especially in the military section I wonder how many of buried service members took their deep dark gender secret of being transgender to the grave with them. Men in particular have a higher portion of transgender service because they saw the military as a way to denying the fact they wanted deep down to be a woman. Sadly many took that to the grave with them. 

On a lesser scale, there are those trans women in the closet who decided to stay there later in life. I can understand the inner turmoil which existed by staying in the closet for the sake of family, job, or even friends. I did it for six months for my second wife just before she passed away. I was so polished in my feminine presentation, you might say in many words I "de-transitioned" to do it. I became so bad off, I resorted to growing back my hated beard, gaining weight and drinking way too much. Terrible is the word which comes to mind when I think back on this period of my life. 

To be able to stay in the closet later in life can most likely be looked at in a couple ways. One of which is the thought pattern I have made it this far in life in the closet, why risk my life as I know it for such a radical change. All you have spent your entire life trying to build could be in jeopardy. Using a current term, you could put your entire life into the "hot mess" category. Spouses, extended family and property are just a few of the things which can be thrown suddenly into the junk pile. The other way is the complete opposite.

If you are not going to try to get out of your closet later in life, mortality is closing in and you may never have another chance. Sometimes relationships with spouses have become routine all the way to toxic, so a change could do you good. My own parents became increasingly toxic to each other somewhere following their fiftieth wedding anniversary and I often wondered who or why they were staying together for. 

These days it would not surprise me to hear of more senior citizen de-transitioners. Perhaps it is because many of given up so much, it makes no sense to go back. On the other hand, in my case I would never give my brother and his family the satisfaction of thinking they were right concerning my right to live as my authentic self. Plus, the fact I enjoy now who I am for the first time in my life can be factored in. I guess I can say those transgender individuals who never came out of their closets until death were better men than I never was.  

Happy Transgender Valentines Day

 

From the Jessie Hart Archives
my Valentine Wife Liz on left,

This Valentines Day I have decided to write about  loves I experienced during my life. I have been fortunate in that I have always had a cis woman who more or less put up with me. In chronological order, here they are.

The only woman who did not know I was at the least a cross dresser when we met and dated was my first fiancé. She ultimately became the only woman to ever attempted to completely dress me up as a woman from head to toe. As exciting as it was for me initially, the newness wore off and problems set in. I can't say my cross dressing led to our ultimate separation before I enlisted in the Army. During my interaction with the military draft board, she told me to tell them I was gay to get out of serving to stay home. If I didn't, she told me she would be done with me. When I refused, she followed through on her threat and I was done with her which was probably the best thing that had happened to me to that point in my life.  I was now on my own when I went off to Army basic training at Ft. Knox, Kentucky.

Ironically, my second big romance came courtesy of the Army in Germany. Once I was there for awhile during my two year tour, I met a WAC. Known back then as the Woman's Army Corps. We started to date to the point we decided to keep seeing each other after we were discharged from the military. She knew I was a cross dresser from the beginning of our relationship so I didn't have to worry about telling her my innermost secret. To make a long story short, we ended up getting along well enough to get married and she gave birth to my daughter. Who turned out to be my only child.  The relationship lasted nearly five years until I was literally knocked over when I met my wife to be of twenty five years. It was love at first sight and somehow, someway I knew I just had to establish a relationship with her.

After a lengthy courtship behind my first wife's back, I managed to win her over. Even when I told her I was a cross dresser also. I can't say the twenty five years were not at times rocky but for the most part they were interesting. Even though she fought completely any thoughts I was transgender, I still loved her dearly until her completely surprise death at the age of fifty from a massive heart attack. I was destroyed for years.

I was still very much dealing with a possible transgender transition when I met Liz and several others who helped me more than they ever knew. It has been over eleven years ago since Liz and I met and we were married last October at the urging of my daughter. Just one of the major things I remember about our relationship over the years was when Liz told me she had never seen anything but female in me.

Over the years of my life I have been fortunate to have been loved and to love several Valentine's which passed through. Perhaps being transgender made the process a little different of course I can't speak for others. But since I came from a family who wasn't known to show emotions and even speak of love, being transgender or not has made the love experience special to me.

Happy Valentine's Day to all of you also and thanks for reading along.  

  

It's in the DNA

The last time I was asked when I knew I was transgender was by my daughter who correctly said "You always knew right?" She was asking primarily because of her own trans child and how to understand them. (They/them are their preferred pronouns.)  I told her I knew to an extent I have always known something was wrong with how I perceived gender. 

Photo from the Jessie Hart
Archives 

In my own personal gender research, I have read of the hormonal effects of the "DES" medication which was given to pregnant women in the time of my birth. If you are not aware, the medication "flooded" the wombs of women known to have problem births. By definition, "DES" is a synthetic form of the female estrogen hormone. The end result was it enabled the women to go full term and deliver healthy babies. My parents were on the verge of giving up and adopting a baby after a series of three still births until "DES" and I came along. As I researched the medication, the more I felt it could have a connection to my gender dysphoria. It could be why, all along I felt so natural anytime I attempted to research my inner feminine side. Perhaps the feeling had been always with me, including the time before I could even express it. 

The entire hormonal aspect of my life came full circle when I started on my own version of "DES" when I started more synthetic estrogen to my system through hormone replacement therapy. It seemed my body took to the hormonal process similar to how a duck takes to water. Changes to my body came fast and furious. An example was when I needed quickly to find looser shirts to wear because my breasts began to grow faster than even I imagined. I can not stress enough how natural the new gender process felt. I feel most people want to zero in on all the physical changes of HRT when in reality, the internal changes were just as big. Just as quickly, my new hormones calmed me down and enabled me to see the world in a whole different light.  In a word, my existence was "softer." 

The more I held my new world in wonderment, the more I wondered why the process happened at all and why it took so long to happen.  The more I questioned the more I came to realize I didn't have a gender choice at all. I was never meant to try to live a male life. Cross dressing as a man, as well as the rest of the lifestyle, probably took years off my life. 

Finally, as I was able to trace my existence at birth (or before in the womb) was because of my exposure to a synthetic estrogen, it all started to make sense. I never had a chance. No matter how hard I tried to please my family and friends, I was always a girl. It was in my DNA.

Exotic yet Obtainable Transgender Women

 

Photo Courtesy Jessie Hart
Archives

One of the prime reasons (initially) when I wanted to check out the feminine world, was I wanted the chance to dress in all the varied colorful wardrobes of other women. Little did I know the journey my desires would take me on. 

Similar to so many of you, I began by raiding my Mother's clothes and makeup. Right away I knew deep down I was doing the right thing for supposedly all the wrong reasons. I always use the "natural" word to describe my feminine needs. As my needs progressed with my age, I found I could attempt to cross several boundaries. Unfortunately one of the boundaries I needed to cross escaped me for years. I write about it often...the need to attempt to dress extremely tacky or trashy to feel more feminine. All it turned out to do was create too much unwanted attention. Once I survived this portion of my life, I could move on to another fun yet challenging phase of my life as a cross dresser. 

Becoming too serious about how I looked in public at times took the fun out of the process. Worry, worry, worry was all I did. Rather than being able to feel how an outfit looked on me, I was seriously zeroed in on if I was accepted as a woman. An example is the early evening when I went to a downtown street fair in nearby Dayton, Ohio. Before it became too dark, I took advantage of being able to wear my sunglasses to see if I was getting any unwanted attention. Once I found out I wasn't, I was able to relax and enjoy the overall experience. Just to feel the air on my bare arms was wonderful.

The more I learned of course the more I wanted to learn concerning my new found freedom as a transgender woman. Specifically when I did manage to set up a few dates with men who seemed to be interesting to me. I stressed on what to wear as I wanted to be more than the normal exotic transgender woman all the way to being subtlety obtainable. In other words, I knew I was already exotic to the men because they knew I was trans, I did not want to be perceived as some sort of a sex object like a trans porn video. Aside from being transgender, I was probably walking the same fine line as any other cis-woman. In case you are wondering, the dates never went past the first or second date, so I guess I was somehow a failure. Then again, I never labored under the opinion I would the woman the men would take home to meet their families. I knew I was some sort of a fling, I just wanted to be treated with respect. Which I was.

I can only say the world we decided to enter as women is a true art form. Walking all the various paths from being a saint or a sinner. Including being able to present well enough in the world to blend in with society at large.  As women today seem to be pulling away from the finer points of dressing up, it is more and more difficult to be exotic yet obtainable. 

Neat Little Boxes

These days it seems, everyday a different term or even an alphabet letter comes forward to describe a different facet of the transgender or LGBT community. In fact the latest LGBT acronym has been expanded to LGBTQIA + to include Queer, Intersex and Asexual persons also. Often when I write the original four letters (to me) I feel remiss in leaving out the other groups but for the sake of simplicity, I leave it alone.

Image Courtesy Christine
Jorgensen 

I wonder also why we need such a selection of neat little boxes to identify with. Perhaps it is because we are learning gender has so many different variations to discuss. Again I will throw up my age as an excuse to be mesmerized by the newer facets added to the old school thought that there were just boys and girls growing up. Then we slowly became aware of people such as Christine Jorgensen  was the first to be widely known for undergoing sex change surgery  To put it into perspective Jorgensen changed gender in 1952 when I was three years old. As I grew up, the only vague terms I ever heard or read to describe at all what my gender feelings were transsexual or transvestite. 

The next main person I remember in my gender dysphoric life was Virginia Prince who I started to follow in the 1970's when I subscribed to her "Transvestia Magazine". Some publications give her credit for coining the transgender term but others don't. It doesn't really matter because in the seventies the transgender term became popular anyhow. I viewed it at the time for ideally describing me. I wasn't ready for any life changing gender surgery but on the other hand I knew my cross dressing was more than an innocent hobby. 

It was during this time I progressed into what I called a very serious crossdresser, even to the point of imagining if I could really be a novice transgender woman. I was trying to fit into two of the neat little boxes and I was having a difficult time doing it. My old male self was fighting back as I slid down the slippery slope to living my gender truth. To cloud my judgement too, this was becoming the time more terminology was being added to the system I was identifying with. Terms such as "gender queer" and "gender fluid" became popular subjects in support groups I was attending. "Gender Fluid" I felt could have really gone a long way describing how I felt when I was younger and totally confused. Just when I thought I had the box thing figured out, two of the biggest, most challenging box choices were still to come as I began to seriously pursue a gender transition. 

The biggest of them all came when I made the ill-fated attempt to live a life in both binary genders. To put it very simply, my feet ended up not fitting in either box and the process came close to killing me. The second was when I had to determine my future sexuality as a transgender woman. During my life I had never been remotely attracted sexually to another man so I wondered if I ever could. What happened was after a couple brief flings with men which resulted in no sex, I was able to settle back in with women friends. So I viewed myself as a transgender lesbian which I see more and more of in social media circles.

It took awhile but I finally figured out which of the neat little boxes I fit into. Until someone comes up with another. 

Getting Dizzy on the Transgender Merry Go Round

Photo from the
Jessie Hart Archives

In a recent post I compared coming out of a gender closet to trying to jump aboard a Merry Go Round which is spinning way too fast. It is difficult to catch up to the established gender you are trying to live as. Otherwise known as desiring to live as your authentic self, a transgender woman or a transgender man. As an extension of the post, today I will attempt to look at what happens once you are able to secure yourself a spot on the Merry Go Round. 

First of all, often you are made painfully aware a portion of the other riders don't want you there at all. Gender bigots or TERF's are everywhere trying for some reason to "protect" their gender from those wanting to live a life of their choice in the world. One of the initial ways they can spot you is from your appearance. Sadly, many of us have to deal with testosterone poisoning which gives our body and facial figures distinctly male looks. As we trans women learn the hard way, there are ways we can camouflage torso's which are too thick with certain items of female designed clothing. The same can be said for makeup which is also an appearance crutch for all women, trans or not. The fact of the matter is, women come in all shapes, sizes and appearance. We have to do our best to fit in. 

Once you have jumped aboard the Merry Go Round, sometimes it is difficult to stay there. My example comes from a lesbian social group I tried to join years ago with Liz. Liz identifies as lesbian and back in those days most all of my friends were also. I was naïve and thought I could join Liz's group but was quickly rejected. The rejection probably came from a woman who rudely approached me at a lesbian Valentine's Dance. She kept asking me drunkenly what my "real" name was. She was mean and nasty and it took me a while to calm down after I relocated Liz who was getting us food. Following the experience, it took me awhile to push my way back on to the Merry Go Round. But push I did. 

I compare the experience I had one time when a friend of mine and I (as males) were in Chicago and took a subway to Wrigley Field to see a baseball game. Being new to the experience, I wasn't quite ready for the rush of humanity which pushed their way into that subway car. Looking back, I was in the same situation many times when I explored my gender change path. From being completely rejected by a lesbian social club all the way to being cornered by a huge cross dresser "admirer" one night in a narrow hallway at a party I was attending with my second wife, I thought I had seen it all. I paid the "I told you so" price with my wife who saved me from my entrapment. Of course she didn't approve of the short mini dress I was wearing and blamed me for attracting the man. 

Through it all, I found once I had earned my seat, I wasn't giving it back to any narrow minded person who didn't like me. I deserved my spot as much as they did and I had to give up my hard earned male privilege's to get it. Plus I certainly wasn't trying to infringe on anyone else's rights. Even though the Merry Go Round was still spinning too fast on occasion, I learned to sit back and enjoy it.       

Transgender Merry Go Round

 

Image from Kitae Kim on Unsplash

Every once in a while, I am fortunate enough to write a post which elicits several wonderful insightful comments. "Trans Reflections and Woman Illusion" posts were examples. First, through the Medium writing format Abbie wrote in and said:

"I've only just realized in the last couple years how far behind the 8 ball I am on this front. After 50+ years trying to fit in as a man I'm now trying to catch up with women and I barely know where to start. Obviously I'm going to miss out on some biological functions but all the relationships, ads directed at women, fabulous but too sexy for my age clothes, even the misogynist/glass ceilings and other garbage. How do us older girls make up for all that lost time?"

The comment started my thought processes which took me back to my early days of coming out in the world as a transgender woman and come up with an answer.

First of all, I view coming out as an older woman is similar to trying to jump on a merry go round which is going too fast. One question I do have is how long did Abbie pursue being a cross dresser before she decided to come out of the gender closet. In my case I was a serious cross dresser for nearly half a century which gave me plenty of time to practice, practice, practice my feminine crafts such as wardrobe and makeup. By the time I was trying to jump on the women's merry go round I was fairly proficient in both crafts. So much so, my second wife was asking me tips on doing her makeup. If I was new to the world today as a woman, I would take advantage of "You Tube" tutorials or go to in person events at some of the big makeup stores such as "Sephora". I know going to a store takes a lot of courage but the benefits are worth it. You just have to be careful of how much money you have to spend. The process can be expensive if they try to sell you items you don't really need.

The next big move I would make is a repeat of a recent post I wrote detailing my early love of thrift stores. In certain thrift stores I was able to partially work my way out of my "teen" cross dressing years and discover a wardrobe which fit me and was much more flattering for a fraction of the money I would have spent in regular retail stores. Plus, once I had settled in on what sizes fit me, I could then begin to order on-line sale items.

Another huge move I made when I was trying my best to come out of my dark/lonely closet was when I went to a doctor and was checked to see if I could undergo feminine hormone replacement therapy at my age of sixty. I could and from then on there was no looking back. Somehow, someway, I had to slow that merry go round down to where I could jump on. When my facial features and skin began to soften and my hair really began to grow, I knew my changes were real and imminent.

Then there were the small things I did to improve my feminine image and present better in the world. Even with the hormones which were supposed to cause me to gain weight, I went on a diet of sorts and ended up losing nearly fifty pounds. I thought of the process this way, if I was going to be a woman, I had to give it my best shot by doing extra things such as taking better care of my skin.

Abbie, doing all of this slowly but surely should get you on the merry go round also. While you can never make up for lost time, you can still build a gender future and enjoy who you have become. Thanks for the comment and I hope any advice I can add helps. Plus when you make your way to the gender of your choice there is always the chance to be able to communicate with the world as your new self. It's a terrifying but exciting journey very few are able to take.

There are other comments I will try to address later in the blog.

Is Being a Woman an Illusion?

Image from Caroline Veronez 
on Unsplash

 Put in it's simplest terms, being female could be defined as the binary gender who can birth other humans and can have monthly periods. A statement many TERF'S or certain politicians would like us all to believe. As we all know, gender is much more complicated than all of that. Even the poor misunderstood drag queens have been pulled into the battle. They never wanted to be women to start with, just look like one. Politicians don't want to understand any of that.   

Now, for the moment, let's consider the old saying "Girls are sugar and spice and everything nice." I am fairly sure those of you who have ever interacted closely with women as a transgender woman or as a man, know a woman or two (or many more) who do not fit the old stereotype. I have seen many cis women who are so much tougher on so many levels. I have also seen many women who are able to cover up their toughness by trying a passive aggressive approach instead. It took many years for me to develop eyes in the back of my head to look for hidden claw marks from women who didn't like me for whatever reason.

Along the way, I have seen many transgender women (novice or not) who project extreme femininity. I remember distinctly one attendee to the monthly cross dressing/trans parties I went to at an acquaintance's beautiful house in Columbus, Ohio. The only time I saw this person was when she quickly changed into a lovely nightgown, lingerie set. Even though I thought her choice of wardrobe was out of place, I could not believe the amount of femininity she radiated. I was sure she was destined to "go all the way" to genital realignment surgery or sex change as it was known back in those days. Very rarely did I encounter a person like this. Of course I saw many men who transformed themselves into beautiful women but sadly their inner masculinity found a way to shine through. In other words, they almost were able to create the ultimate gender illusion but just fell short. 

Perhaps it was just because they were just like me and were living a part time life as a man also. In my case I had to take my whole study of womanhood to a whole other level. Similar to the other glamorous cross dressers I encountered, I wanted to do my best to look feminine. I wasn't a natural, so I knew I had a way to go. It wasn't until after another bitter battle with my second wife did I begin to understand I still had a long way to go until I could take the next step and totally undertake being a woman. What happened was the night before I had been mistaken for a cis woman at a transvestite mixer and my male ego was at an all time high about reaching a new goal with my feminine appearance. After the fight calmed down, my wife told me she wasn't speaking about how I looked as a woman. She was talking about I had none of the experiences it took to achieve womanhood. From that moment forward, I dedicated my life to understanding what she meant. It was difficult to study woman from afar but I did the best I could. Sadly, she passed away before I could achieve my goals. It would have been interesting to see if we could ever could have been friends as women. 

In conclusion, being a woman is not an illusion. It is an earned right we are all entitled to. No one is born a woman, we are socialized into the title. Transgender or not, learning what that means is the most difficult part. 

Transgender Reflections

Reflection from
the Jessie Hart
Archive

Reflections from transgender women and men can mean many things. Of course mirrors come to mind first. Through our lives we worship viewing ourselves as a way of reinforcing our new feminine selves. This can go both ways as mirrors have a not so sly way of lying to us. That very short mini skirt which looks very good on an attractive teen aged girl most likely won't look so good on your much older testosterone poisoned body. Most of us as time goes by and we interact with the public more and more come to learn the mirror's shortcomings. It took me more than a couple times of being stared at, all the way to being laughed at to understand the mirror was not coming close to telling me the truth and I was attracting too much unwanted attention.

Finally, what happened to me was I replaced the mirror's reflections with ones from interacting with the public. Specifically when I started to interact one on one with other women. When I began to move forward from just interacting with sales clerks who were always nice because my money was green, onward to stopping at upscale venues for lunch, I really had to step up my feminine game. Specifically, I needed to do more than walk the walk. I needed to talk the talk. In other words I needed to quickly learn how to communicate on an entirely different and foreign gender level. To be clear, I am talking about more than just sounding feminine because I found women communicate on many different levels. Including a fascinating level which I learned which involved speaking on a non verbal level. I learned so much without even speaking from other women. I was spared potentially embarrassing interactions with drunken guys in bars with just a glance from female bartenders. Talking the talk without actually speaking was huge.

Reflections then became more important from a personal point of view. Once I had gained a basic confidence in how I interacted with the world as my new authentic feminine self, I could concentrate more on how others were viewing my reflection. I had the very rare chance to reinvent myself and learn from all of my mistakes. Including the ones I made when I was a new cross dresser or novice transgender woman trying to find my way in a new terrifying but exciting world. Losing my old male privilege played a part also, specifically when I found myself in dangerous situations when I was lucky to not be physically assaulted. It took me awhile to learn there were feminine privilege's too which went way past just having a man open a door for me. Just having the opportunity to be able to play in the girl's sandbox without being clawed was a privilege. 

Even though I still suffer from gender dysphoria when I look in the mirror in the morning, I am able now to look past the shallow reflection and see the bigger picture. In a new life as a full time transgender woman.  

All Kinds of Transgender Dilemma

 

Image from Karla Hernandez 
on UnSplash

We transgender women and trans men have always encountered plenty of dilemmas as we complete our gender transition, or attempt to. Most of us have friends, family and jobs to consider. Sadly we are considered to be selfish as we pursue our gender goals. Ironically there is truth to the selfish idea because we often need to address our most inner souls to find a path. We found muses were difficult to find.

Dilemmas were everywhere. I know one of my biggest drawbacks to transitioning earlier was trying to figure out how I would support myself. Most certainly I would have had to quit the well paying, hard earned male career I had managed to carve out. None of it seemed fair but who said life had to be fair? As I quote my parents who were fond of telling me just that when I didn't want to do something they wanted me to do.

Another huge dilemma came when I needed to learn the new basics of presenting and appearing realistically as possible in my new chosen gender. The whole process really defined being alone with a terrifying array of cosmetics to deal with. Then there was the problem of what to do about a new wardrobe. Styles and sizes became very important as well as cost. I was in a situation where I needed to hide any feminine expenditures from my wife. I found one big solution by shopping the thrift stores. I could purchase ultra cheap clothes and see if they fit on a very small budget. Plus, I was even able to gather the courage to try an item or two on in the dressing rooms. Finally I was able to dress my way out of my teen girl years and into a reasonable facsimile of what a cis woman my age would wear. Thrift stores not only gave me an excuse to go out shopping, and save money, I could also conquer the appearance dilemma at the same time. 

At the same time, I was ignoring the few friends I had accumulated. Slowly but surely my feminine side was sneaking into the forefront and stealing my life. The more I was in the public's eye, the less male time I wanted. It was working out to be a huge dilemma. The more I accomplished as a transgender woman, the more natural I became and all of a sudden the whole impossible dream of living a feminine life became more achievable. 

My dilemma  of telling friends I wanted to be a woman very much went away when my small circle of close friends passed away close to the time when my wife died. There was no one left to tell. Family, as I have detailed several times, my problems coming out to my family was a different process. Even though my parents had long since passed on, I still had a daughter to tell as well as a younger brother. I had a highly successful experience with my daughter and an equally bad one with my brother who I have not spoken with for nearly a decade now.

My final big dilemma was what to do about my finances. At my age I was getting close to being able to retire on early Social Security. I also owned a house full of antiques and collectibles I could sell to raise money, so I took the early out and retired. All of which of course, did away with me have to worry about job hunting as my new authentic feminine self. With most all of my dilemmas in the past, the door was finally open to complete my gender transition.