[vc_row][vc_column][vc_column_text]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.

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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.[/vc_column_text][/vc_column][/vc_row]

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Andrea Adlerberg
6 years ago

The picture is riveting…I can think of no better way to describe it. It shouts, " I am me….deal with it!" Love that sentiment. Appreciate the article. There should be more appreciation for individual evolving instead of feeling we must avoid the dreaded “flip-flopping" label at all costs. Thank you for so eloquently giving voice to what many of us feel.

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Kim Paige
6 years ago

Thanks Captain Sally! Yes, I’m coming to realize if I focus too much on the “destination”; I miss the joy in the journey.
Thanks so much for posting this!
Kimberly Anne

6 years ago

Beautifully written! I find myself evolving in this journey. The problem I face is letting myself explore outside my own boundaries, the ones fear have mostly built. I find myself right now stuck where I occasionally wear lingerie to wanting to go beyond that and fully dress even if it is only once. I have know early idea where to go next.

6 years ago

Thank you caption Di. Thats soo true I know that my journey has had a lot of ups and downs. I always return to dressing up and feeling free again. My best time was when I was dating a female to male he brought out the best in me and got me over some of my hang ups. I was more of a closeted dresser and he showed me that going out as a girl was wonderful. He was right when he told me that most would never even notice you because they are soo wrapped up in what they… Read more »

Active Member
6 years ago

Love this! So many great take aways. I have been dressing off and on for more years than I care to recall and can definitely see a process of evolution in my perception of who I really am, as well as in how and when I dress. I’ve been out fully dressed a numbers of times, yet still very much enjoy being home alone dressed.
Thanks for sharing a very relatable article.

Michelle Liefde
Active Member
6 years ago

As I continue to explore this site, I keep coming across amazing and thoughtful insights like this. Thank you Captain Di. Your words have given me a lot to ponder!

Isabelle O'Malley
Active Member
3 years ago

This is such an awesome read and almost describes exactly how I feel. Biggest difference is that in my line of work (software engineer – I.e. binary ) there is no grey area and few co-workers would understand (tolerate?) me showing up dolled up on the days I feel like expressing my feminine side.

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