It Was the Worst of Times; It Was the Best of Times.”

With apologies to Charles Dickens for rewriting his classic line from A Tale of Two Cities, this post’s title is a very apt description of the last year and a half. During this I experienced the absolute lowest point in my life, along with one of the best things to have ever happened to me. It was a period of not only sadness, shock, grief, anger, and a sense of unreality but also a period of deep introspection, discovery, change, acceptance, and the adoption of a very “new normal.”

It was the worst of times because in November 2021, my wife of forty-two years passed away following a fourteen-year battle with Parkinson’s Disease combined with dementia that had developed later in her illness. She was the love of my life and I miss her more than I can put into words. I was her caregiver as Parkinson’s relentlessly took away her ability to physically care for herself, and dementia eventually took away her ability to think for herself. It is difficult to watch someone you love physically deteriorate, but it is truly heartbreaking and excruciating to watch their mind and memory fade away. I held her in my arms as she took her last breath and was torn by conflicting emotions: comforted that her considerable suffering had finally ended but devastated that the best part of my life was over. I soon descended into an agonizing state of darkness, grief, and despair, with months passing in a confusing blur. In the spring of 2022, my state of mind improved thanks to the efforts of a bereavement counselor, who guided me through the darkness and enabled me to see the light at the end of the tunnel. It was not long before my thoughts once again returned to crossdressing. I am past retirement age but have been crossdressing since my teens. For all those years, I was a closeted, lingerie-only dresser who used any alone time at home or time away on business trips to indulge my passion, which included under-dressing on occasion. My dressing significantly diminished during the worst of my wife’s illness, disappearing completely during the darkest time after she passed, but now it has returned, albeit in a very different fashion.

My life began to change from the worst to the best of times thanks to a lady named Fiona, who I met last April. I had occasionally seen glimpses of her around but did not really know her very well. This gal was intriguing and unlike any woman I had ever met. Soon after we got acquainted, we quickly became friends, then very close friends, and finally wound up being inseparable. She was pleasant and seemed very comfortable with who she was. Like me, she was mature, tall, and thin, but unlike me, she dressed stylishly and younger than her actual age. We were opposites in many ways: she likes to shop; I do not; she cares a lot about her appearance; I did not think about it that much. She also turned out to be much more outgoing than I usually am. I very quickly became enamored with her and wondered what it would be like to experience life as such a person. I answered my wondering in early May, and it came in the form of a wig, my first. I had accumulated a small wardrobe because my thoughts about dressing had somehow shifted to wanting to dress fully and go out in public, something I had never before contemplated doing.

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On the day they delivered the wig, I put on a nice dress, some lipstick, and the wig. Walking into a room with a full-length mirror, I was mesmerized by the nice-looking lady looking back at me. My feelings burst out in a soft, “Oh my” and I just sat and looked at her for a long while. It was then I decided to become her. I soon found out that deciding to be her was one of the easiest life-changing decisions I have ever made. On May 5, 2022, I was out the door in public En Femme as Fiona and have not looked back since. Initially, I did not want anyone looking at me and was nervous the first few times going out, although not as nervous as anticipated. Soon afterward, I became relaxed and felt very comfortable while out dressed and did not care at all who looked at me. In fact, I learned to welcome the attention and my confidence soared. It developed into a feedback loop where the more I went out, the more my confidence increased, making being out even more comfortable and me more confident. As the months went by, I had no idea where all this was headed. I decided to just let things happen and see what developed. Well, what developed is that since last fall I now basically live 90% of my time out in public and 100% of my time at home dressed as a woman. There are usually a few days per month when I go out in drab, but otherwise, I do all the run-of-the-mill, day-to-day things like food shopping, the library, post office, restaurants, doctor’s office visits … etc. as Fiona. I have determined that I am not a woman trapped in a man’s body and have no desire to fully transition. Living the majority of my life as a crossdresser suits me just fine.

I told the bereavement counselor about Fiona, and she fully supported me. We covered two important subjects related to my grief and Fiona’s subsequent appearance. First, was her appearance an attempt to have a woman in my life after losing my wife? Second, was I using Fiona to escape the grief? Further discussion showed that neither of these applied in my case. In fact, I made it a point to ensure I was not being an escapist by visiting my wife’s grave dressed as Fiona. I have also come out to a select group of friends and acquaintances with everyone being very accepting. There are others who I will never tell about Fiona, not because they will cut me off and never speak to me again, but because their knowledge about Fiona will likely change our relationship. I value my relationships with these people just as they are and do not wish to alter them. Last fall, I had the good fortune to meet a great group of other trans ladies from CrossDressers International (CDI) in New York City. Allison and the other gals were very welcoming and quickly made me feel comfortable. They hold weekly dinners in their private city location, and I try to go there twice a month to socialize, enjoying being with a nice group of friends and acquaintances in a relaxing atmosphere.

So, as you can see, my recent past has been one of extreme lows and exhilarating highs. The highs do not cancel out the lows, though. The grief of losing the lovely woman with whom I had the pleasure of sharing a good part of my life will always be with me, but it will change. It has already changed somewhat because the last eleven months have turned out to be a wonderful experience. My future is trending towards increased happiness and contentment and things are definitely headed in the right direction. I consider crossdressing a gift, one that has made my life immeasurably more interesting and pleasant. When thinking about my very new normal, a line from Shakespeare’s Hamlet often comes to mind– “To thine own self be true.”

I am so glad that I was.


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Anna Redhead
Trusted Member
1 month ago

@Fiona Black Thank you for sharing this

Fiona Finlay
Active Member
1 month ago

@Fiona Black You mentioned in your PM to me about how you now live almost completely as Fiona.  I’m glad to have read the story of how it came about, although I was saddened at the heartbreaking loss of your dear wife.  Let me add another belated thanks for having written this lovely article. Albeit without having been bereaved first, it does rather seem that I’m now treading the same path where you have gone before.  “I had no idea where all this was headed. I decided to just let things happen and see what developed."  That’s more or less… Read more »

Trusted Member
1 month ago

Fiona I may have responded to this before but I do want to applaud you for this post regardless. It’s both sad and uplifting in a truly rarer way, anyone who has experienced loss can identify and anyone who is a cd can identity even further with it. Ty for sharing a peice of yourself, to me it’s essentially reading and I don’t think I’m alone. 

Active Member
1 month ago

@Fiona Black This was a great story. Sometimes coming out of the ashes helps us know who we really are and who we are supposed to be. I’ll be many of us feel that exact same way. 
Thank you for sharing and I wish you well. 

30 days ago

@Fiona Black so beautifully written. Thank you.

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