The Path

Source: Cyrsti Hart

Over the years here in Cyrsti’s Condo I have been amazed how many of the like minded transgender women I have encountered followed the same transition path as I did. Then again, I have ran into many trans women with totally different paths.

I have written a number of times how I used athletics to cover up the fact I really preferred being a girl. For example, being a football player kept the bullies away. Enough said. Perhaps what I haven’t written so much about was my military service. Unlike so many others, I didn’t voluntarily join the Army to make me a man, I was drafted during the Vietnam War. Guess what,  my time served still didn’t help me to stay in my male closet. It only helped to reinforce what I already knew, I had a woman lurking to experience the world. In fact, the military provided me the opportunity to come out of my closet to three close friends for the first time in my life. When I told them I was a transvestite. 

Now we can fast forward through all the years of Halloween parties being the only opportunity to leave the closet and experience the world as my girl self. 

In the 1980’s was the first time I could be aggressive and force my gender closet open and sample the world as a woman. As with any other tremendously difficult endeavor, my path had it’s ups and downs. I was frustrated when I felt I was taking one step forward then two steps back. For example, when I felt I looked the feminine part, I would do something such as twist my ankle in heels. 

Finally I decided I needed a plan for my path.  Instead of meandering without a plan, I decided to begin a process which would lead to a transition…or not. Here is what worked for me. Plus, I need to point out, it was a different time to attempt to come out of the closet, so stick with me.

What I did was try my hand at so called “easy” places to pass in. I went to bookstores and shopped at women’s clothing stores where all which really counted to the sales clerks was the color of my money. Emboldened by my success, then I expanded my trips to stopping and eating lunch. I still remember two of my favorite outfits. The first was a pastel green “business style” suit which I pared with pastel green hose and heels. The second was a black dressy jump suit with black pumps. Both outfits were worn with my long straight blond wig I loved so much. The end result was I blended well in the upscale malls I chose to go to. 

Even with all the so called success I was experiencing, there were downfalls also. Most came when I tried to do too much and ended up looking like a drag queen. I can’t tell you how many times I went home in tears.  One day I even learned my lesson from one young girl I estimated to be four or five in a women’s clothing store. As I turned the corner through another rack of clothes, we startled each other and she shouted to her Mom  “Look at the big woman!” I quickly thought  at least she saw me as a woman. But there was more. The girl went on to say “A big mean woman.” Lesson learned. Wipe that male scowl off my face.

I tried also to challenge myself to accomplish different goals as I experimented surviving in a feminine world. 

It turned out my path would take several different branches before I arrived where I am today. Living full time as a transgender world with a successful relationship and an accepting daughter. More on it later. 


Makeup Magic

 Most certainly one of the most bewildering ,yet on occasion fun part in a transgender woman’s transition is making yourself up. Of course, very early in the transition game, the importance of attempting to align your external source with your authentic self becomes very important. 

I remember back to the earliest days of rummaging through my Mom’s makeup drawer and “borrowing” certain items I had seen her use such as lipstick and eye shadow. The challenge always was to use the items and put them back so well she would never notice. She never mentioned it, so perhaps I was careful enough to get by. 

All of this took place during the 1950’s and I lived in a rural area where I was able to deliver news papers for extra money. I saved my paper route money and combined it with the small allowance I received for doing chores around the house and actually had enough money saved to purchase my own makeup. Having the money was one thing but finding a place to spend it and buy makeup was another.

Those days were way before the advent of any makeup specialty stores. The closest I could afford and find away in town to go to were a couple of the old “five and dimes” department stores. They featured a small selection of many items (including makeup) a lunch counter as well as other items. I was even able to find me a pair of women’s shoes I cherished on one of my shopping excursions. 

Another problem I encountered was how was I going to get to the stores I wanted to shop at plus once I was there, having the courage to actually go in and search for makeup. I was able to overcome the transportation issue by spending the night at my grandma’s house. She lived very close to downtown where the stores were located. I could walk and pick out my hard earned treasures. 

As I wrote, I vividly remember the fear or out right panic I felt the first time I gathered the courage to go in the store and shop. I ended up feeling very relieved when I finally reached the makeup section…until I saw the selections which were available. I thought, now what? My plan had been to briskly walk in, pick out a couple makeup items, head back to the checkout counter and leave. My plans did not include a lengthy stay to shop. 

Through it all, I stayed the course and purchased a couple of items. I was certain the whole world was staring at me but they weren’t. I survived the checkout counter and headed back to my grandma’s.

Little did I know  from my humble beginnings at the makeup counter, I would have many more occasions to feel nervous. Over the years I would have much more error than trial when it came to applying my own makeup. Finally the internet came along and I was able to study makeup tutorials and improve my craft. 

Ironically I became so skilled my two wives (who wore very little makeup) would come to me for advice when they wanted to dress up. 

When I became very serious about transitioning was when I attempted to take my makeup to another level,. During this period I was desperately trying to blend in with the professional woman and proper makeup was a necessity. 

These days I have basically gone full circle with my makeup. Thanks to the results of hormone replacement therapy and age, my skin has softened and the angles of my face have rounded, Naturally, I need less makeup when we go out although I still wear more than Liz. Since Liz is a former “Avon” makeup sales person, she still retains a knowledge of the artform.

She has been threatening to do a makeup job on both of us before we go out. I can’t wait for her to work her magic. 

No Power no Post

Source: Cyrsti Hart

 Yesterday turned to be a complete bust as promptly at 7:45 AM, our electric power went out. After the usual paranoia about paying the bill, I realized it was too early for even the electric powers to be to be shutting it off. 

Since my partner Liz is still very much a working woman, she gets up before me to have her morning coffee, take care of the animals (except me) and get her morning meditations done before clocking into work as she works from home. 

As I turned over and noticed all the power was off, Liz met me at the steps to the bedroom to tell me the energy company had robo called her and said the power would be restored in approximately two hours. Approximately was the key term as it was nearly twelve hours before our electric was restored. 

We live in an all electric home, so everything ground to a halt. Including our heat. 

Heat wasn’t so much of a problem to me because it isn’t that  cold and I could but on an extra sweater. What really bugged me was not having a television. I was forced to spend extra time faced with only me. I am my own worst best friend always overthinking every situation which causes me extreme anxiety at times.  To counteract part of my destructive thought processes, I even sleep with the television on. The harmless shows on the “Hallmark Channel” always seem to do the trick and I can quickly fall asleep. I truly get panicky inside if I have to think of sleeping without noise. Fortunately, Liz has learned to live with my quirky behavior. 

The whole day of facing myself stressed me so bad I still couldn’t sleep when I went to bed, television or not. I finally fell asleep approximately four thirty in the morning. It’s barely 10:30 AM now, so that is my excuse for this rambling post. 

 As with any negative situation, there is usually something positive which comes from it. The good thing that happened was I  found I was going to get an extra night out because we had no way to cook dinner. The trick was to put what ever small amount I wear anymore on by flashlight. The whole process turned out to be surprisingly easy. In fact, I thought of many cheap shots to use when describing my makeup which I won’t use. The good part was I was riding a wave of confidence because when we went out to vote on Tuesday, the lady who checked me in called me mam. That’s always reassuring even though I have never experienced any problems when I have gone to vote. 

The only problem we possibly experienced at dinner was one older woman who couldn’t seem to not wanting to stop and stare at Liz and I as she was leaving. It was so bad even Liz noticed which is rare. Normally I always do before she does. It’s possible also, since Liz and I were sitting together across from her son, the woman thought we were lesbians which is a whole other story. 

All in all the power was on when we returned home and life returned to what passes for normal around here. With or without sleep.

Terrible-Part Two

Source: Cyrsti Hart

Mark sent this comment in regarding the recent post called “You Make a Terrible Woman”. “Very well done too Liz viewing YOU as a WOMAN …NO–Way do YOU make a terrible Woman . Putting your self down there .MARK”

Thanks for the comment Mark. First of all I don’t think either of us (deceased wife) or myself took it literally the way she said it. First of all, I didn’t make anything. I only was moving in the only survivable direction I could by putting my male self in the closet and living as my authentic self. Plus, since she is no longer able to speak for herself, she did add she wasn’t referring to my appearance.

Being of a stubborn nature, it took me awhile to understand exactly what she was trying to tell me. After all, I had spent a lifetime admiring and observing the girls and women around me. By doing it I could only observe the external workings of a feminine world. If I had the chance to go inside, perhaps I wouldn’t have been so enamored with the feminine binary gender. As I learned so many years later women operate with their own set of unique passions. Specifically with aggression. Understandably, men deal with power and women with passive aggressiveness. 

I am fond of saying when I started to play in the woman’s “sandbox” I found I had  to be on the outlook for knives being aimed at my back. Smiles many times meant nothing. 

So Mark, I wasn’t really putting myself down. Her comment served to send me back to the drawing board. I had to find out what she meant. In those days it was difficult because of the very rare times I had to get out of the closet and live as my authentic self. In fact, it took me twenty years before I could even come close to doing it. 

Once I did begin to get out in the world, I found appearance was the easiest hurdle I had to face. Not because I looked so good, it was because other factors became so important. Such as very quickly I had to learn to communicate one on one with other women. All of a sudden, what they didn’t say became as important as what they did say. Plus, what was I going to do about my voice. I finally went to a voice coach to learn the difference between men and women as they communicate. 

In some senses I feel the powerful “terrible” comment is a wonderful motivator for me. It keeps me focused on being the best person I can be and not squandering a truly powerful opportunity to lead a quality life as my authentic self.


Well, it’s here. The day I have been seemingly writing about forever and a day which paved the way for my current out transgender lifestyle. It’s Halloween of course.

Throughout the years often I wished I could have followed the path of nearly everyone I knew. Costumes were for fun or creativity. Not as serious as mine were. Then there were all the years due to work situations I couldn’t wear a “costume” at all. 

All of that is in the past now. Looking back at it all, I was fortunate enough to be able to live most all of my Halloween fantasies. 

On this Halloween, I hope you have too!

You Make a Terrible Woman

Recently I wrote a post concerning the reactions from my past two wives when they were confronted with my gender issues. I left my current partner Liz out because by her own admission she has always viewed me as a woman. 

Liz (left) Photo Source Cyrsti Hart

To rephrase what I wrote in the recent post, my first wife was fairly bland when it came to dealing with  me being a cross dresser. Back in those days also the word transgender was not even known. So it wasn’t even a discussion point.

All of that changed with my second wife who I was destined to be with for twenty five years before her death from heart problems at the age of fifty. She was as stubborn as I was and we became embroiled on numerous occasions. All of which were caused by me wanting to go further and further towards living full time as a woman. 

Several times I remember vividly. 

The first (of many) occurred when we lived just Northeast of Marietta, Ohio. It was a time of my life when I was really starting to find success going out and experiencing life as a feminine person. To “manufacture” more reasons to go out when she wasn’t home, I began to do things like the grocery shopping. When I did it, I slowly expanded into doing other kinds of shopping too. All of it worked well until I accidently ran directly into my wife’s boss in a store parking lot. I thought I succeeded in passing him until nearly a week later I heard the infamous comment about him seeing a large red head when he went to the store. It just so happened I had and wore a red wig at that time. Of course I denied all knowledge. It turned out it didn’t matter anyhow. She caught me cross dressed in public and the giant fight which came later led me to my first sessions with a gender therapist.

It turned out, the visits with therapist just put off the inevitable, I still continued to slide towards living full time as a transgender woman. 

The second of many fights I can remember came after one of my most successful cross dressed outings I can remember. I have written about it here in Cyrsti’s Condo many times. It was the night I went alone without my wife to a transvestite “mixer” when we lived in the NYC metro area. Two women sat at the door and were going to deny me entrance because “No real women were allowed.”  Of course in those days all I had to validate me as a woman was my appearance and I went on a giant ego rush. All of it made me impossible to live with and my second wife and I ended up in a huge fight. 

During the fight she said what quite possibly were the most profound I heard in my entire life, “You make a terrible woman.” I was taken aback because the night before I had been mistaken for a woman. Then she went on to say she wasn’t talking about how I looked. There was a deeper meaning I hadn’t even considered and wouldn’t until I actually started to seriously transition. 

Without going deeper into the whole process now, I learned the nuances of gender communication and privilege when I began to live as a woman.

It’s easy to say now but she was right. I did make a terrible woman. However I did take the opportunity to rebuild my life in a feminine world. A world which was dramatically more layered and pleasurable than the male world I had known. 

The wait was worth it. I’m not so sure the cost to my soul and to others around me was. My cross dressed man did make me miserable and unfortunately I made others around me miserable too.

Equal Time

Source: Cyrsti Hart

 Recently I have been writing several posts concerning the interaction between my Halloween adventures and the interactions with my wives (at separate times.)

First of all I had experience with two wives for the stories. The first was much more accepting than the second but both knew about my cross dressing urges before we became married. The problem became more prevalent  as I slipped further and further into the realization I was much more than a cross dresser. I wanted to follow the natural urges I was feeling to shove my male self into the closet and live full time as my authentic self. 

My second wife used the well worn phrase, she didn’t sign up to be in a relationship with another woman. Plus, a few other phrases I will save for another post. 

What happens to the spouse when that happens? Back in the day, I used to take a look at a few blogs which dealt with women who were immersed in relationships with their husbands who suddenly told them they were transgender. Needless to say, the reactions I read from the wives were not positive. Even I was shocked. 

I think what we all miss during our Mtf transitions is that cis women have egos also. In many cases a husband figures prominently into her ego. Or, what she did wrong to “drive” her husband into the feminine camp. 

As far as I am concerned, I don’t know how I would feel if the shoe was on the other foot and my spouse wanted to complete the difficult journey to another gender. I just know it would be very difficult. 

I can understand too how a transgender path could be considered the ultimate in being selfish. After all it is an all encompassing desire to make it to the other side of the gender divide. What happens to a families life, jobs and kids when it happens?  It’s so difficult to help another person to understand there is really no choice when you are considering crossing the gender frontier. It is so much more than just dressing as part of the opposite gender. It is life or death. 

So, my heart goes out to all the understanding spouses I have been reading about recently. Or even the ones who begrudgingly have come to accept and stay with with their former husbands or wives. Of course the internet has helped with all of that. Positive information abounds on how couples in love have survived their gender journey together. 

Taking my local scene as an example. the transgender – cross dresser support group I am part of has recently featured several couples who are successfully staying together. As I wrote, all my positive thoughts go out to the spouses who made it happen.

Equal time! Good job!