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.


  1. girlieboy69 says:

    “You’d make a terrible woman,” is a very powerful statement.. I suspect you were like I am, a female-sensitive, though still male-minded person. I would wish for HRT if I could have it feminine my brain without changing my body.

    1. cyrsti says:

      I sense you already have a female mind. HRT will feminize your exterior!

      1. girlieboy69 says:

        Thank you, that’s very sweet. If I could do it without breasts I’d be fine.

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