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“It Was The Worst of Times, It Was The Best of Times”

It is my distinct honor to run this post. This is exactly why there is a Kandi's Land!

by Fiona Black

With apologies to Charles Dickens for rewriting his classic line from the Tale of Two Cities, this post’s title is a very apt description of the last year and a half during which I experienced the absolute lowest point in my life along with one of the best things to ever happen 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 after a fourteen year battle with Parkinson’s Disease combined with dementia that 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 quickly 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 in large part to the efforts of a bereavement counselor who guided me through the darkness and enabled me to start 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 diminished greatly during the years of my wife’s illness, disappeared completely during the darkest time after she passed but now returned albeit in a very different fashion.

My life started 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 before 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 somewhat 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 was.

I became enamored with her very quickly and began to wonder what it would be like to experience life as such a person. My wondering was answered in early May and it came in the form of a wig, my first. I had accumulated a small wardrobe by then 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. On the day the wig was delivered I put on a nice dress, some lipstick and the wig then walked into a room with a full-length mirror. I saw the nice looking lady looking back at me, let out a soft “oh my” and just sat and looked at her for a long while. It was then that I made the decision 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 5th, 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 somewhat nervous the first few times I went out although not as nervous as I had anticipated. Soon afterwards, 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 as a result. This 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 but 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 where I go out in drab for one reason or another but otherwise I do all the run of the mill, day to day things like food shopping, the library, post office, restaurants and doctor’s office visits … etc as Fiona. I have discovered that I am not a woman trapped in a man’s body and have no desire to fully transition so living the majority of my life as a crossdresser suits me just fine. Last fall, I also had the good fortune to meet a 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 with a nice group of friends and acquaintances in a relaxing atmosphere. In a few weeks a group of us are getting dressed to the nines and going to the opera at Lincoln Center. What fun!

I told my 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 simply an attempt to have a woman in my life after losing my wife? Secondly, was I using Fiona just as a way to escape the grief? Further discussion showed that neither of these applied in my case. In fact I made it a point to insure I was not being escapist by visiting my wife’s grave dressed as Fiona. To escape by being Fiona would have only prolonged the process of eventually having to deal with and overcome the heartache. 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 knowing about Fiona will likely change our relationship in some manner. I value my relationships with these people just as they are and do not wish to alter them in any way.

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 large 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.


7 Responses

  1. Fiona, first of all thank you for being so open and candid about both the loss of your wife and the impact it had on you. You clearly still miss her and you have my heartfelt sympathies both both your loss and what were clearly very difficult times leading up to it.

    I loved how you described the emergence of ‘Fiona’! I have to confess that it was not until the third paragraph after you introduced her that I twigged! I find it fascinating how our feminine sides can contrast so much with our other side – I’m in exactly the same position although I’ve yet to put interaction with others to the test – and I often wonder whether our subconscious understands what’s going on long before we do. Your counsellor’s thoughts were interesting too; clearly here the focal point was the loss of your wife but I’ve often wondered which side of the mirror I’m focussed on – what I see in the reflection or what I actually feel. In the end, though, who cares? If we have a deep sense that things are right, that’s all that really matters.

    This was a wonderful post and I look forward to reading more from you!

    1. Thank you for your kind words Amanda.

      Your comment about the subconscious is interesting. Before last April, the thought of dressing fully & going out in public had never crossed my mind in all those many decades. I had underdressed any number of times while in public but didn’t find it particularly gratifying. My counselor suggested that at some point in the past a seed was planted in my subconscious mind that eventually grew to be Fiona. Funny how the mind works.

      The one thing that confused me for a while was how quickly I became comfortable being out in public and how easily it was for me to live life presenting as a woman. Where was the nervousness, the doubt, the fear, the guilt, the second thoughts, the shame? I wondered about it numerous times until I realized what you expressed above – that I did indeed have a deep sense that this was right and that was what mattered the most.

      1. In many respects, the likes of us are a psychologist’s dream! What makes a seemingly normal guy want to transform so completely into a female and then step into the outside world in that persona? And then do it repeatedly, each time pushing themselves a little further?!

        What fascinates me is that I know that in my case, it’s not just the old cliche of being a woman trapped in a man’s body. I can see elements of my personality that fit much better into a female persona but others that are resolutely male. That, of course, is an ideal recipe for being non-binary but I am very much binary in the way I manage the two facets of my life – it has to be all or nothing either way, not half & half.

        And as for the planting of the seed, I suspect it happened while we were still in the womb but I’d really like to know for sure!

        1. Yes, we are a “psychologist’s dream”. The thing that baffles me the most is what makes a young boy all of a sudden want to wear his mother’s or his sister’s underwear? I get that there are a number of potential explanations but I just cannot wrap my head around why that occurs. And it’s not just a few isolated cases, it’s a fairly common occurrence.

  2. Thanks for sharing your story with us . so sorry to hear about your loss and so happy to hear about your rebirth as Fiona. Very inspiring ❤️

      1. You’re most welcome Fiona. This is a whole new world for me . Having a place where I feel safe to communicate with other likeminded people. I have never really come out except to my wife who accepts me and tolerates my cross dressing to a point. I’m thankful and glad to be a part of this community that Kandi has put together. I look forward to getting to know all of you better 🙂

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