We all evolve over time

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.

Stepping Out Secrets

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.

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.

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Dionysus (Captain Di) The Corsair

Captain Di is an evolving explorer of the merger, or co-mingling, of the elements of the masculine and feminine that exist in different levels within us all. Captain Di believes in honest, self-expression and self-exploration with the goal of pushing the boundaries of what we limit ourselves to when we adhere to a system of what we "should" or "should not" do, become, or express our individuality through.

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  1. Michelle Liefde 4 months 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!

  2. Ashleigh 9 months 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.

  3. charlie 9 months 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 are doing. Now I dont give it a second thought I walk tall and proud.

    • Author

      Courage, it is said, comes not from being unafraid, but from being afraid and doing it anyway. We have to evaluate all the potentialities, keep ourselves safe and sane, but for some of us, finding the courage to be who we are is not only difficult, but scary.

      Sometimes you have to not care about the judgments of others, but it can be dangerous for us out there. Having someone who is supportive and will help you take steps forward is something we can never overestimate the value of. It is what they mean by priceless.

      Keep it real, keep it safe, and keep the faith!

  4. Robin56 9 months 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.

    • Author


      Try easing into your boundaries rather than thinking you have to crash them. Push gently against them, step back, push gently again when you feel yourself able. Most people seem to believe they need to crash against their boundary walls and then they get hurt, in one way or another, and they run away and either don’t try again, or wait a very long time.

      I wish you the best of luck in your journey!

  5. Kim Paige 9 months 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

    • Author


      Keep on traveling, and think of each milestone on the road as its own destination, leading to the next stretch ahead. Like a rest area, pit stop, or place of interest along the roadway of life, we often rush through them to get back to the road. I’ve found it much more rewarding to, as they say, “stop and smell the flowers,” rather than dismiss these mile markers as less than important. Each step means something.

  6. Andrea Adlerberg 9 months 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.

    • Author

      In regards to the pic, which is one I collected over the years, I have always mixed feminine dress with pirate clothes. The odd thing is, most people these days think it is stranger that I dress like a pirate than like a woman. We are who we are, and we need to be cool with ourselves, regardless of what others tell us we “should” do. Whenever you hear the word “should” or comparable, I believe we need to stop and think. In psychology, “should” is considered a bad word, as it dictates to us rather than allowing us to chose.

      Much luck on your journey, wherever it takes you.

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


  8. Marie Bardinot 9 months ago

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

  9. Amanda Patrick 9 months 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.

    • Author


      I can easily relate to where you are. At one time I dressed completely, at another I went out to a club in a skirt and heels regularly, but now, time and my situation in life has changed, and I dress far less and have much less of an urgency about it. Where I am now involves balancing what I believe to be my masculine and feminine energies as I look to discover deeper truths about who I am. Wherever you are, that is okay, and no one else can tell you that you need to do “more” or commit yourself to a goal that is more in line with theirs, something people usually do because deep down they want there to be others who are like them so they are not alone. Keep on traveling!

  10. Cloé (CC) 9 months 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.

    • Author

      My spiritual nature tells me much the same, Cloe. I believe we are meant to explore, push boundaries, and break new ground in these bodies we inhabit for a relatively short period of time. Wherever that leads, as long as it doesn’t involve hurting ourselves or others, or demeaning or judging others, we owe it to ourselves to take the journey forward to where it leads next.

  11. 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 was born under a wandering star, a wandering, wandering star!

    Lady Veronica

  12. *skippy1965(Cynthia) 9 months ago

    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 is private in their dressing to go out because we assume that what they want when in fact they may be happy where they are. I think the key is to LISTEN to the person and support and encourage them to share their goals and fears with others who might have helpful insights or advice. We want to help those who are desiring to do more or go farther but fearful about what might happen to have the confidence to overcome those fears . While it is important to be aware of the potential dangers, we also know that the imagination often creates far more horrific scenarios than reality often provides.

    So it is our duty (and honor and pleasure as well) to help our fellow community members realize THEIR goals without imposing OUR gals on folks who are either not sharing those goals or are not truly prepared to take that leap. It is that vision that I try to promulgate in chat and the forums with both long term friends and newcomers alike. I have been blessed to receive that from you Cap’n as well as from countless others here and that I hope I have given to others. Thank you and keep on doing what you’ve been doing!

    • Author

      Thanks, Cyn, I think you used the right term here. To push someone beyond what they want to do/be, or tell them they are not doing enough, as I was back when I would go out dressed from the waist down, is indeed shaming. Just as the obsession with being “passable,” and the relative shaming of those who others don’t consider “passable,” is changing.

      The perception in this area has changed over the years. Much like the rejection people who identify as bisexual had in the 1980s, with those who identified as gay telling them they were “afraid to commit,” and heterosexual people rejecting them on spec, something that rarely happens these days, TG folks have been more open to variations on the gender identity spectrum.

      Keep on traveling, Cyn!

    • 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.


  13. Kara Kelly 9 months ago

    Thank you for this wonderful article.

  14. Marianne 9 months 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.

    • Author

      There is definitely a sort of balance that goes on. We do change over time. For over a year, in 2005-2007 I lived with a very accepting woman, who then, shall we say, used it to manipulate me. It was worse than just that, and it drove me away from dressing for many years, but it came back in 2016. Now, I consider myself gender creative, as my medical issues prevent me from doing things that were once very important to me as a crossdresser, such as heels. With rather severe rheumatoid and osteo arthritis as part of my diagnosis of Lupus, I’ve had to adapt. Short skirts were also a favorite, but that is a problem since I can no longer cross my legs (you can figure out why). The feeling has never really left, as it never does with us, at least not for long. Over time, we change and adapt to differing circumstances in our lives, whether it is where we live and who with, medical issues, a bad experience related to our dressing (such as I had in 2005-2007, and some have other bad experiences such as going out dressed and being mocked or attacked verbally or physically), and the way attitudes have changed over time. When I used to go out dressed as a “halfsie” from 1999-2001 (meaning I only dressed from the waist down female and as a pirate from waist up) I was approached a number of times by TG women and drag queens who told me “You are not trying hard enough, sweetie, you have to dress completely.” Last year, going out dressed as a Hooters waitress to a Halloween party at a local LGBTQ+ club, I had TG women and drag queens tell me I was fabulous, even as I did nothing to my face and was obviously male. The point being, we change over time, but many believe their dressing and focus on it will remain the same, which is one of the reasons why a full transition is a HUGE decision.

      And yes, helping others when you have a wide range of experiences over time, I believe is important for those who have had those experiences. We owe it to those who are struggling, just starting to come out, to help them see the possibilities and the obstacles, while respecting where they are and not pushing them beyond what they are emotionally and mentally capable of going.

      Much love, Marianne, you are awesome. Don’t ever forget that, my Nordic friend!

  15. Jezebel Trannie 9 months ago

    Wonderful article !

  16. Jezebel Trannie 9 months ago

    Love the photo !

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