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My Odyssey

I am simply honored to run this post...

By Fiona Black

Editorial comment: My sister!

I was recently looking through a dictionary for a word to help me solve a clue in a crossword puzzle when I ran across the word odyssey which was defined as “a long wandering usually marked by many changes of fortune”. It struck me that this definition was also a good description of the journey crossdressers undertake as they explore their feminine sides. It can certainly be a long, sometimes lifetime long, wandering among all the stages of dressing from just wearing panties to underdressing, dressing fully, going out in public, being private or deciding whether to tell employers, friends and family about one’s feminine self.

And there will indeed be many changes of fortune along the way, some good, some life-altering and some devastating. Of course the word odyssey reminded me of Odysseus, the Greek hero of Homer’s epic saga who, after fighting for ten years in the Trojan War, undertook a perilous ten year voyage to return home. During his journey they were times he had to disguise himself in order to survive or to uncover the truth about someone. That reminded me how many crossdressers assume the appearance of a woman to survive their dissatisfaction with living as a male or to uncover some truth about themselves.

All that got me to thinking about my own crossdressing odyssey which began in earnest in May 2022 when I dressed fully and went out in public for the first time. These last seventeen months have been a period of learning not just about female clothing, makeup and mannerisms but, more importantly, a period of self-discovery during which I have learned some interesting things about myself.

1. Hindsight being 20/20, I have looked back on my life and found that the feminine part of me was more prominent than I ever realized. I always talked and acted like one of the guys but deep inside I felt that some of the things I did or said were not quite right, they felt “forced” somehow. I often second guessed myself, wondering if how I acted or what I said was the right thing to do. There were also occasionally times where I would encounter something such as a scene in a movie, a story on television or something I was reading and I felt myself getting very emotional in ways that people usually associated with women, not men. I would have to compose myself and remind myself that guys did not act this way.

2. I finally came to understand that I did not have something wrong with me because I liked to dress in women’s clothes. Throughout the many decades I was a closeted, lingerie crossdresser, I certainly enjoyed dressing but there were many periods when I was embarrassed and confused by what I was doing. I went through numerous purges in an effort to end what sometimes felt like a dirty, loathsome part of my life. All that ended when I joined a couple of crossdresser web sites and began to read stories of other crossdressers lives. I discovered there were thousands upon thousands of others like me! Most of them seemed like just ordinary, everyday people, not degenerates!! And some even lived as women!!! Of course, not having led a sheltered life, I knew all this already to some degree but it was not until reading these stories, chatting online and meeting then becoming friendly with other crossdressers that I realized that crossdressing was so much more common and widespread than I had ever realized. It dawned on me that a whole new world awaited me and the seed that had been subconsciously planted in me at some point during all those decades of closeted dressing quickly began to blossom.

3. I have discovered that I am much more comfortable in my female persona than I ever was with my male self. I am noticeably more confident in who I am and much more satisfied with my appearance. All these positive emotions helped make my decision to live full time as a woman a much easier decision than it might have otherwise been.

4. As a crossdresser who is constantly out in public, I have had to learn a lot about female clothing, makeup and mannerisms. My expertise in each of these three areas is okay but far from perfect. However, I have found that I am not overly concerned about not being perfect because there is a fourth element that, for me, has proven to be more important in how I am perceived than these other three. That fourth element is confidence. Of course any crossdresser going out en-femme needs a certain level of competence with regard to clothing, makeup and mannerisms but I found that lacking confidence in who you are and how you present yourself will negatively impact how you are viewed and the quality of your interactions while out in public. As Kandi has often said, being confident is a key element in having a pleasurable dressing experience.

5. I have become more outgoing and social than I have ever been. As a male, I rarely initiated conversations with people I did not know well. At parties or gatherings, I would occasionally contribute in some small way to a conversation but was usually satisfied to sit back and let others lead the way. And if I could find a way to avoid the gathering altogether, I would jump at the chance. As a female, if there is some sort of get together, I make every effort to attend, join in the various conversations, meet new people and I enjoy it immensely. I have initiated conversations with people in parks, stores and restaurants which is something I had never done before and I do it without having a feminine voice. Socializing is now a pleasure rather than a burden.

6. Amazingly, I now like to go shopping which I used to hate. As a male, it was quickly go in, find what you need and quickly get out. When I was with my wife, I would sit somewhere and eventually get impatient as to what the heck was taking her so long. Now, I’m the one who lingers, checking out styles and fabrics, trying things on and looking for bargains. It is fun looking for things that will make you look pretty or sexy versus just quickly picking up something you need. I shop so much that there are any number of sales assistants in various stores that know me by name. Of course I get a dose of reality when the credit card bills come due but I have decided to enjoy myself to the max in this new stage of my life. So it’s full steam ahead, carpe diem, time to fill up another closet and shop till I drop!

7. Even more amazing is that I have become a much better dancer as a woman and enjoy dancing much more than I ever did previously. I have no clue why, it’s a complete mystery.

8. Of course there are some negative things I have learned as well. I have been a widower since November 2021 and there may come a time when I would want to look for another life partner. By deciding to live as a woman, I am greatly reducing my chances of finding a lady who will accept me as a mate. However, I have decided to let the chips fall where they may and just enjoy life as much as possible. Even if I do not ever find another partner, I will always have Fiona, a lady I have come to love.

So after twenty years full of trials and tribulations Odysseus finally returned home to be reunited with Penelope. Similarly, after wandering all my life through the crossdressing landscape, I finally came to my new home and have been united with Fiona.


24 Responses

  1. Fiona,
    What a fabulous telling of your journey through life. I am so happy for you.

    Thank you so much for writing your odyssey and sharing it with the world. You are indeed a wonderful woman.

    You look so beautiful.


  2. Thanks for sharing your story, Fiona. I am sure that there are many here who can identify with all or parts of your message.

    1. You are welcome Donna. While everyone’s story is unique, there is a certain commonality that runs through most of them.

  3. Fiona,
    Finding a companion does raise problems , I agree with you in that if it happens then so be it . Unlike you I am divorced after 45+ years of marriage , the ironic twist being my ex-wife started telling people I’d died after she was told by a counsellor she was suffering a bereavement .
    Amusingly I recently took a coach trip and short cruise on the Leeds- Liverpool canal , an older gentleman sat next to me on the trip and asked me to join him for the included meal . He insisted on buying my wine and on the return trip gave me his contact details , thsi was new ground for me so I gave him my details . While I have no interest in male companions it showed how a relationship could come out of the blue . I’ve come to the conclusion that it’s better to find reliable friends rather than spend time searching for something that may or may not happen .
    I also realised that if we do find a female companion that may progress further we are also raising questions about their gender preferences , if they aren’t aware of yoiur true gender .

    In a reply to Amanda I commented on the use of the word ” crossdressing ” , you use it more as a noun to describe YOU but maybe consider using it as a verb as an action to define your inner needs as a female . I’m sure you have come to the situation where it no longer feels like crossdressing , you have become Fiona like I have become Teresa but I need to deal with the formalities to get full legal acceptance .

    For the rest of your post I totally agree , the female inside us makes us a better , more rounded person , I was surprised how quickly I adopted and adapted to my new lifestyle , it just feels right . I have been fulltime now for almost six years and it gets better and better .

    1. Teresa,

      I came out to a female acquaintance yesterday who was totally accepting and thrilled that I was being true to myself. During the conversation the subject of a future mate arose and she said this: ” A woman who doesn’t accept you for who you really are is not really a woman you want to spend the rest of your life with.” Her comment basically mirrors my current way of thinking. I have spent the last two decades taking care of others – my wife through her long illness, before that my mother and before her my father – and have decided that from here on out it will be all about me. I may or may not cross paths with someone who accepts Fiona but I intend to enjoy myself no matter what happens.

      I have reached the point where I am Fiona and Fiona is me. And like you, it just keeps getting better.

      1. Fiona,
        So important you now have time to take good care of yourself .
        I forgot to comment on your mention of dancing , like you I would struggle to step on the dance floor as a man but now once the music starts I have to be dragged off it . Heels were made for dancing , OK my feet let me know the next day but I can live with that .

  4. Fiona, that was a really nice post. I’m always touched by your consideration for those around you as you have sought your own happiness & contentment and to see how you have blossomed since losing your wife is inspirational.

    Maybe you’re right with point 8 and the pool of potential partners is reduced but those who are still swimming, so to speak, will be the ones who’ll accept you unconditionally. It’s just a case of keeping your fingers crossed that your paths will cross when the time comes.

    1. Amanda,

      After getting to know you through your blog posts here and emails we have shared, I have always been very impressed by your consideration for those around you so to hear you direct that comment my way means the world to me. Thank you so very much my friend.

  5. Hi Fiona,
    Thank you for posting this wonderful chronicle of your journey to womanhood. I am sorry to hear about the lose of your partner.
    This was so well written and it’s going to help a lot of our sisters in their journeys I’m sure. I totally enjoyed reading it. You and Amanda are right up at the top of my list of authors to read. Thanks for taking the time girlfriend.


    1. Thank you Trish! When I decided to contribute to Kandi’s blog, I told her that I would be happy if I somehow helped even one person in their dressing experience. I figured the best way to do that was to be as open about my experience as I could. What I did not realize was that writing these articles would also benefit me as well by helping to sort things out in my mind as I got used to living a new life.

  6. Fiona, you are amazing and it’s great you are doing what you want. Keep on keeping on and things will be fine. Have a great day. Huggs, Jan

  7. Hi Fiona,
    Odyssey is the perfect word to describe this journey. And confidence is the most important thing you need on this journey. Without it, life can be a very scary place. A person needs to own it.
    Clothes shopping, especially heel shopping, is so very different now as well. For example, I would maybe shop 2 times a year for shoes. Now it’s 2 or 3+ times a month
    As a divorced person, I too am finding it hard to find a lady who will accept me as me. But that’s one of the criteria I am looking for in a partner.
    Finally, I no longer describe myself as a crossdresser, I call it blending. I don’t wear women’s, nor do I wear men’s clothes, just my clothes. I’m not in female mode or in male mode, just Cali mode. I joke that my closet has transitioned.
    PS When I get time, I plan to write about Cali’s journey.

    1. Agree 100% on the importance of confidence Cali. And I look forward to reading about what brought you to becoming Cali.

  8. What a great thoughtful post Fiona
    Much resonates with me but the one thing is finding a relationship knowing that Rachael is here to stay.
    I’m not full time but not that far from it.
    Thanks for sharing just a small part of you

  9. You could have been describing me, except for the better dancer part. I just don’t have it in me. Its been more than a dozen years since I started going out and coming out. Now, I find I prefer to live my life (within certain limits) as a woman. Its not quite full time, but very close to it. (Yay!!!)

    And although I am not a widower, I have two long marriages in my past. The second finally ended precisely because of who I am. Although I would love to have a supportive partner, I find I am content to have supportive female friends.

  10. Kim,

    One of the many pleasant surprises about living as a woman is indeed the number of supportive female friends and acquaintances I know. Feels good to be just another one of the girls.

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