I recently looked through a dictionary for a word to help me solve a clue in a crossword puzzle and came 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 in exploring 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.

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, there were times he had to disguise himself in order to survive or to uncover the truth about someone. That reminded me of how many crossdressers assume the appearance of a woman to survive their dissatisfaction with living as a male or to uncover some inner realizations about themselves.

It got me 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. In hindsight, looking back on my life I 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 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 times when I would encounter something such as a scene in a movie, a story on television or something I was reading and 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.

EnFemme Style

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, who 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 websites and began to read stories of their 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 to some degree but it was not until reading these stories, chatting online, meeting them, and becoming friendly with other crossdressers that I realized that crossdressing was so much more common and widespread. 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. Being confident is a key element in having a pleasurable dressing experience.

5. I have become more outgoing and sociable 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.

EnFemme

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 a number of sales assistants in various stores who 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 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 greatly reduce 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.

EnFemme

 

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Julie Day
Member
Julie Day
7 months ago

Thank you so much Fiona for the wonderful essay. Your insight into why we do this was wary well thought out. I feel the same way you do about my feminine side. I have meet so many wonderful girls here from all walks of life and all having similar feeling to how I feel. When I see a women now, I am more interested in what they are wearing, how they us their makeup, and other things like nails and hairstyles. I am always wondering how I would look in the same dress or makeup. I feel more in tune… Read more »

Julie Day
Member
Julie Day
7 months ago
Reply to  Fiona Black

Thank you Fiona, I love being able to share my feminine journey with such lovely girls like you. 

Leonara
Ambassador
Trusted Member
7 months ago

Fiona,
Thank you for sharing your crossdressing “Odyssey”.. your article referencing your out and about as your feminine self is inspiration for me (especially your suggestion: “Being confident is a key element in having a pleasurable experience”). I will take that into my feminine heart as Leonara finally steps out into the world.
Please accept my condolences on the passing of your wife… I am sure it was a difficult time..
you have a wonderful writing style and thank you again for putting your crossdressing Odyssey experience to words…
Warmest regards, Leonara

Dani
Lady
Active Member
7 months ago

I loved this article. Thanks so much for sharing. Many of your points I would definitely echo. xoxo

Suzanne Martin
Member
Active Member
7 months ago

Fiona – My condolences for the passing of your wife. I enjoyed your story, there are many good points you made. I spent most of my life being “manly" suppressing my gentler side. It has only been in the last few years that I have come to understand and embrace that I have a feminine side. I get much enjoyment out of being able to dress and express this part of myself. My only regret is that it took me so long to recognize it. Thank you for sharing your odyssey and may you continue to enjoy your journey. XOXO… Read more »

Dawn Judson
Ambassador
Active Member
7 months ago

I’m jealous, Fiona, of what you’ve accomplished in such a short time. I have enjoyed dressing since I was about 11 years old, but to use your terminology, my “crossdressing odyssey… began in earnest in" 2017. I’m disappointed that I haven’t made more progress. I identify with a lot of points that you make. As you say, crossdressing changes the way you think, feel & act. It is intriguing to see how different I am, as me, as opposed to him. Thanks for your post.

Dawn

Cassie Jayson
Duchess
Trusted Member
7 months ago

Thanks, Fiona, for sharing your insites of your journey. I think so many of us here are on similar journeys. I to have spent a few hours here and there all my life, never going out ashamed of myself. NOW over the last 3 years I have come to accept Cassie as an important part of me (or is she the real me???). Now I am living full time presenting as a woman, except at work. I have found that most of the important people to me are either accepting or don’t care, so it make going the next step… Read more »

Lauren Mugnaia
Duchess
Trusted Member
7 months ago

Thank you Fiona, for sharing your odyssey with us. As others have already said, your journey echoes that of many of us in so many ways. I’ve been working on a book about my life, growing up with the constant knowledge that I was playing in the wrong sandbox. All my life I was very feminine in speech, mannerisms, and physical traits. All of my friends, in the past and now, have always been girls and women. I have always been able to speak to women on the same level as they did, we just always connected. Recently finding out… Read more »

Ashlee Lauren
Lady
Member
7 months ago

Very inspirational Fiona thank you.

Mona
Duchess
Noble Member
7 months ago

Awesome article Fiona. Very well done, thank you for sharing it with us.

J J
Lady
Active Member
6 months ago

That was a wonderful and well-thought-out article…thank you for posting it. I suspect most of us find many things to relate to in it, even if we took different paths or found different endpoints.

I too have found the confidence you mention and brought to light things about myself that were always there but were hidden or suppressed and I have now embraced that make me a happier, healthier person.

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