In the journey of life, we often think of ourselves as heading towards a destination. For many here, the destination is a transformation towards what we think will bring us peace and happiness, becoming our true feminine selves. Often, that transition, whether it is through HRT, surgery, or presenting as female in public without the full transition. For others, dressing privately, or with a select, trusted group of people, is enough.

What does it all mean? We can ask that question a thousand times and never really have an answer. Is our goal, often dreamed about for years, even decades, of time truly the final destination? There is no right answer. Over time, that goal may change. A private crossdresser may have been satisfied with that at one time, but as time goes by, they may desire to present in public. They may have thoughts of transitioning. There may also be a reversal of goals. I knew a crossdresser at one time who loved to present in public, and later became more private, and then lost the desire and need completely. Your goals, your dreams, your desires, and even your identity can change over time. It is not about satisfying others and their expectations, but about what brings you peace, happiness, and has you feeling that you have become, or are living, as your true self.

That true self is a mystery, and it always will be. As many have said, life is about the journey, not the destination, and I agree with that one hundred percent. Along the journey, things change, attitudes change, and our goals change. In a world where changing your mind, completely normal over the course of a lifetime, and will happen many times, is considered “flip-flopping” or a lack of commitment. We need to ignore that and let our lives take their normal course, and to greet and welcome change as it comes. One who doesn’t learn new things and new attitudes over time becomes trapped in stagnation.

My story is different compared to most of the folks on this site. I tinkered with crossdressing at a young age, like many of you, but until college it was a small collection of isolated incidents. In my freshman year of college it was not even on my mind. I was more concerned with trying to lose my virginity. It wasn’t until I changed colleges in my sophomore year, going far away from home to try to overcome what was then crippling shyness, that I began tinkering with it again. It was, however, limited to shaving my legs and wearing short shorts wherever I went. I didn’t have the means to buy female clothing, all my money came from my parents who kept track of what I spent money on. Being very shy at that time, there was an excitement in just going to class in shorts with shaved legs.

EnFemme

At the time, it was enough, I have a rather strong fetish when it comes to legs, and that was always the driver behind my dressing. I wanted to have legs as nice as the girls I desired who wouldn’t give me the time of day back then. Fully dressing was not part of the goal until two years later. I was in a relationship with a woman who was very sexually adventurous, and at her suggestion we tried to spend a weekend away at a hotel switching gender roles, and I found myself very excited wearing her clothes, and having an excuse to shave my legs again.

It wasn’t until a decade later that I began experimenting again, this time dressing female at Halloween parties, which became an annual thing for me. Combining female dress with a costume was my cover. One year I was a witch, another time I was a demonic cheerleader. I shaved my legs in the winter and stopped in the summer when I lived in New England. Later, when I moved to Florida, I began shaving my legs every day, something I still do today, and wearing short shorts like I had in Arizona. The difference was, I was no longer shy, I knew people, and I began purchasing my first female clothes, mostly miniskirts and heels. I began dressing for people, and for a while I dated men, meeting them for dinner or drinks, and then, if they were sane and safe, I would invite them to my apartment and dress up for them.

All of this relates to the evolutionary nature of who we are, regardless of whether we identify as transgender, crossdresser, gender fluid, or any other of the labels available these days. Over time, we may change, we may shed identification with one label and feel we are more aligned with another. Does it matter? These days I consider myself “gender creative,” as I like to mix male and female clothing when I go out. I identify as both male and female, and I couldn’t care less what anyone thinks about that.

In Sonu Shamdasani’s introduction to my edition of Carl Jung’s Liber Novus, or The Red Book, the following passage stands out for me. He is paraphrasing Jung when he writes, “Jung provided a definition of the soul. He argued that the soul possessed qualities that were complimentary to the persona, containing those qualities that the conscious attitude lacked. This complimentary character of the soul also affected its sexual character, so that a man had a feminine soul, or anima, and a woman had a masculine soul, or animus. This corresponded to the fact that men and women had both masculine and feminine traits.”

We are in the realm of exploration, not of destination. Our journey is never complete, it is ongoing, but where you are on your journey, you must find your way to peace in that time, and keep yourself open to further exploration, accepting change as it comes. Rejecting change, trying to smother it to remain what we were but no longer are, only brings anger and sorrow.

May you be at peace in your journey.

En Femme Style

More Articles by Dionysus (Captain Di) The Corsair

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Jezebel Trannie' class='avatar avatar-64 photo' height='64' width='64' />
Jezebel Trannie
6 years ago

Love the photo !

Jezebel Trannie' class='avatar avatar-64 photo' height='64' width='64' />
Jezebel Trannie
6 years ago

Wonderful article !

Marianne
Ambassador
Active Member
6 years ago

You gave me much to think about here. My journeys have all been towards something new and different, always striving to excell and do things better or have higher achievements than others. That may often have made others either intimidated or alienated and consequently I have mostly been appreciated more for what I can do than for who I am. Here on CDH I actively try to balance that through not just being another successful crossdresser but a good understanding and supportive friend to anyone in need.

Kara Kelly
Lady
6 years ago

Thank you for this wonderful article.

skippy1965 Cynthia
Ambassador
Trusted Member
6 years ago

Cap’n. Great article and I think you reply to Marianne included a very salient point. Many of us assume others want what we want whether that be full transition(medical,surgical or just lifestyle) or getting out in the world as female or simply being happy to express this side of themselves in the privacy of their home or by under-dressing and whether sharing the experience with others or keeping to solely to themselves. I have seen folks-here and other places-insist as you experienced that you do MORE than whatever it is you currently do. This can be pushing -even shaming-someone who… Read more »

Sabrina (Brina) MacTavish
Managing Editor
Noble Member

Cyn,

Well said and a motto we should always live by. “Listen first and never tell" Ours is to encourage, console, and enlighten those who seek out our guidance.

Brina

Dame Veronica Graunwolf
Active Member

Captain Di…….I love that picture and your story. When people ask me…."where are you from", I always reply….oh, here and there and right here now. There is no time when I am happiest, other than being on the road. It is the voyage not the destination that powers me. My favorite song that describes me is from Paint your Wagon. Oh, I was born under a wandering star, oh, I was born under a wandering star. When I get to heaven, tie me to a tree, or I’ll begin to wandering, and who knows where I will be. Oh I… Read more »

Miss Cloe
Managing Ambassador
Member
6 years ago

As a person of faith, it strikes me that it has been described that we are spiritual beings dwelling in tents (our bodies). So what does it matter if today I want my tent to be decorated feminine? So here I am with a blue tent knowing that I need it to be pink to match the feminine spirit that dwells within. For now I will be content to let decorations be that outward reflection of the person I am, but pink is on its way.

Amanda Patrick
Member
6 years ago

Hi Captain,

Thank you so much for the wonderful Article. I seem at Present time to be in that Backwards Mode. I have been out a few times in Public. But lately Seem to think I just want to stay at home or get a room and relax there. The desire to dress has also Calmed down. not completely but has gone very quiet .This is my journey for the present time. I Will relax and enjoy it and see where it goes.

Marie Bardinot
Lady
6 years ago

Great article, I really relate to some of the things you mentioned in it.

April (Pacific Princess)
Ambassador
Active Member

Lovely article Cap. The journey truly is what life is about.

April

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