My Odyssey

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.

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.

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.

More Articles by Fiona Black

• Keystone Redux
• “It Was the Worst of Times; It Was the Best of Times”

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