Did you know you were transgender when you started crossdressing? Or did you simply find a rationalized unexplainable pleasure in wearing garments that were typically women’s clothes; so, you crossdressed. You were a crossdresser, right? You were a man that for whatever reason found wearing women’s clothing quite . . . . (you fill in the blank)
There was no way that you were transgender, but now something is. . . different? You reason in your head, ” Maybe. . . but . . . . no, not me. I just enjoy wearing women’s clothes.” And yet undeniably within your mind, there is “tossing it around” happening. You know it, but vaguely. At this point, you either don’t know what “it” is or you are afraid of being honest about “it.” Moving from being a crossdresser to understanding that you are transgender is not inevitable, yet often the two have a connection.
I crossdressed when I was younger. It was normally an erotic experience and usually somewhat disheartening. Disheartening because I knew eventually I had to take off all the clothes and go back to my male world. Erotic because it was the means I was able to recover something “good” out of the deep disappointment of having to go back. Dressing was so pleasurable, so natural, and yet something was incomplete, something was missing. I knew it, but I did not know what “it” was
However, upon reflection, I realize that I came to understand “it” rather quickly. In those days (early 70s; I was a young teen then) there was no generally recognized term or vocabulary to explain or define “it”. As best I remember “it” was defined in this way, “I want to be a girl.” Over time, I came to realize I just didn’t want to dress as a girl (woman), but I truly wanted to be one. Dressing alone couldn’t achieve that for me, thus the disappointment.
The next leg of my journey came as a result of a magazine article (yes a real paper and ink periodical). It was the early 70s. In our home, we received Life & Look Magazine. In one of them, a particular issue had a feature story about transsexuals, (this was the vocabulary of the day.) The headline on the cover announced the feature story, causing an emotional tsunami within me. I just had to read it!
In the article, I met Sally (I believe that was her name) and her fiancé. Sally was interviewed dressed in her bridal gown preparing for her wedding. Sally was a fully transitioned transsexual woman soon to be a bride and wife. She was young and exquisitely beautiful. She was living her life exactly as I dreamed to live my own.
I devoured the article. I cried. “Oh God,” I said, “This is me!” Finally, I knew what the “it” was. Crossdressing never fully satisfied me because I was more than a crossdresser. My “it” was that I was a transexual. And in Sally, I recognized that there was a means whereby I, a teenage boy could successfully become a girl. This understanding delighted me, yet it still plagued me because, at that time, I was still understanding myself to be a man who wanted to be a woman. This desire ran deeply cross-grain to my sincere Biblically Christian faith.
Upon understanding that I “could be turned into a girl,” I ran from rather than to that reality. This running away indeed occupied the great majority of my life, and certainly was the source of much mental and emotional anguish. Forty-eight year’s worth is my estimate.
Even the best runners finally tire, and I did too. Yet those years weren’t wasted, rather they were invested in understanding this condition, which eventually became properly named as gender dysphoria. With an understanding and explanation that I could be at peace with in light of my fundamental Christian faith, which I was determined not to abandon. I finally admitted and ultimately embraced my reality. I am not simply a man, a male. I am transgender.
Furthermore, I finally concluded: OK, just say it, “I am a woman.” Now I understand and readily embrace that despite all outward evidence, I am a woman at my soul level. I am not simply a man with a strong feminine side, rather I am a woman who is deeply feminine and longs for the world to know me as such.
That’s where I am now. I am not currently transitioning in the accepted normal sense of the formal process. Yet, I am transitioning. How I understand and accept myself certainly is progressing away from the old, “I am a man wanting to be a woman” concept. Considering transition as a possibility rather than an impossibility is a step on the transition journey, yes? Actively engaging in the unseen but customary feminine self-care routines in preparation for a possible transition is a “transition” for me. For those who are on the formal transition pathway or who are now living your own womanhood full-time, were these not steps you may have taken prior to your formal coming out?
I am not sure if I will fully transition, but I am much more open to the idea of a part-time life as my feminine self. I believe full-time would create tremendous upheavals for many; so much “collateral damage.” I am not ready to do that to them. Yet, I wonder, “Is it not possible that by becoming Charlene full time I would be providing for them an opportunity of personal growth? Would not my non-traditional womanhood require their own growth if they chose to accept me as a woman? In my transition to my authentic feminine self would I then not be doing something for them rather than to them?” So many things that need to be sorted out, but one is finally settled, I am a woman.
My transition may not be to full-time womanhood, but maybe it will. I don’t know at this time. Certainly, in a vacuum, I would do so, but at my age, there are so many lives that are closely intertwined with mine. My transition would affect them as well. Perhaps in a positive way, perhaps not. At this time I have made a conscious decision not to force that choice on them.
The point is that understanding and embracing yourself as trans is a process, a journey as so many call it. I am currently 68. I have been consciously on this journey for 63 years. I don’t regret not transitioning earlier. I don’t regret taking all this time to figure it out.
But what I am concerned about is the possible regret that will come if I choose to remain closeted rather than introduce Charlene to the world at large. I am not a man who wants to be a woman, no, I am a woman who simply wants to be. Imagine coming to the end knowing that very few if any actually ever knew the real you.
I hope this helps. May you, the reader, be blessed in your journey of self-discovery.
More Articles by Charlene K
- The Value of Therapy
- Intentions
- Where do I Go from Here?
- I Will Never Know; I May Never Know
- Trading one Question for Another

Charlene K

Latest posts by Charlene K (see all)
- The Value of Therapy - July 8, 2024
- Intentions - March 23, 2024
- Evolution in the Trans Life - December 12, 2023
Charlene, that is so true that as women we are more caring and intuits to the feelings of others around us. Having empathy, I feel is one of the greatest traits that a woman has, and I feel so blessed to have that.
Barbra
Charlene, I cannot express the heartfelt joy I feel when someone will take the time from their busy lives to in courage and to give hope to a complete stranger Thank you!
Hugs Barbra
Barbra, I don’t see you as a stranger to me. You are a sister in our community to whom I am honored to be a blessing. As I understand it a passion and empathy for others is a mark of the nurturing nature we have as women. Yes?
Kindly,
Charlene
Charlene what a wonderful article. I was born in 1957 for me at the age of 5 I knew I was different by the age of 9 I had tried on my first bra. When watching Televison I always wanted to be the woman. By puberty is when I found that I was truly attracted to men, so I thought that I maybe an effeminate homosexual and being raised as a stricter Catholic I knew I was going to hell. I have cross-dressed all my life it was at the age of 19 that I realized I was a… Read more »
Hugs,
Charlene
Charlene K Charlene. Thank you so much for this post, it really does resonate with me in a number of ways. We are a similar age and I too began crossdressing in the early 70s and also found it to be an erotic and wonderful experience. I still remember seeing the front cover of the Melody Maker weekly music magazine in October 1973 which featured a large photo of Wayne County performing. This stirred something deep inside of me and soon afterwards people like Candy Darling and April Ashley provided more inspiration. Until quite recently I considered myself to be… Read more »
Hi Wendy, thank you for your reply. I do appreciate you and your journey.
I do hope your journey allows you the opportunity to evolve as far as you want in the pursuit of your own womanhood.
Though I do wish to physically transition, I currently don’t see it as something possible for me. But I am confident at my core I am a woman, and am looking forward to a greater degree of authentic self expression. And who knows? I am evolving.
Kindly.
Charlene
Thank you for your lovely article, Charlene. I would love to physically transition, and it was both encouraging and heartwarming to read the replies from the other ladies here who feel the same way or who have already transitioned. Once again this morning I am now up, with my coffee, still in my nightgown. I look at myself, and deep within me I feel the strong emotions that are begging to be embraced and fighting to be set free. The monetary costs of surgeries I suspect for an America are significant, and setting aside money for this is not something… Read more »
@danikiss22 Thank you Dani for your thoughts. Be content with what you have, yet always considering the means to be your authentic self in new situations.
I don’t ever expect surgeries will ever be part of my journey, but that doesn’t make me any less a woman, who though sadly not cis, has embraced her status as a woman who is trans.
Kindly,
Charlene
@jilleanne Hi Jill, thank you for your thoughts. I have had these same thoughts, but my need for full time womanhood has not yet come to that crossroads.
Will it? At times I hope so, yet I then shrink back. I am comfortable where I am at, but yes, I must admit the desire for more is ever present.
I am happy (and to be sure a bit envious) for you. I trust living as your true self is all you had ever dreamed it could be.
Kindly,
Charlene
Charlene K Yes, I guess I came to a point in life where I just had had enough and came to fully accept, this is me. Selfish maybe? I don’t know for sure but I knew nothing else took priority over my happiness. What helped greatly was meeting a woman who fully accepts me as me. A big bonus giving me the strength to move forward. I still have lots of days of confusion, frustration, etc. so it’s not always joyous per se. one little tidbit I have discovered along the way is my wife will notice a difference in… Read more »
Charlene K Charlene, I think we all have different levels of self acceptance for where we are at in our lives. I was once where you are now for sure and was able to say to myself, I’m in a good place right now. That for me however later on changed in subtle ways with no warnings or indications I was to come out fully. It might for you or might not, who knows. Either way, stay happy as you can. Know you have a real friend in me no matter where your road travels. I’m with you girl. hugs,… Read more »
First I am so happy that your partner “gets it" and knows and accepts you as and for who you really are. What a blessing.
Secondly thank you for this, “Know you have a real friend in me no matter where your road travels. I’m with you girl. hugs,… “. That kind of support means sooo much to me.
Hugs,
Charlene
aka: Charrie to my friends
i am glad you have introduced Charlene to me, because knowing her has made me a better person .. i hope someday you will introduce Charlene to the world at large, because knowing her will make the world a better place… you know the girl, just do whatever you think is best for her ..
btw, tell her sara says thanks ❤ …
i appreciate that i am looking to get more involved and to advocate in some way, i’m not quite sure about the details but i know i’m following the right overall path, and you are a big help to me
Kindly,
Charrie
Charlene your story resonates with me as i have gone fromthinking bout transition to developing a realistic plan for making it happen.. thank you so much
Sara, thank you for taking time to comment. “Developing a realistic plan." I am happy for you. Let me know your progress.
Kind hugs,
Charlene
i think it’s going to be a matter of weighing what i want and need against the collateral damage to some good people who really care about me and will have a hard time dealing with it
Charlene, I love seeing accounts like yours. Why? because I see so much of what you have written as I see myself. I came out to my wife nearly 4 years ago and I thought I had been a crossdresser all my life. Very quickly I realised that I wasn’t a crossdresser, I was transgender. I’m soon 62 years old and spend much of my life as the female I really am. My wife is very supportive but to keep our relationship and our love for each other, I will not fully transition. Instead, I cross dress as a man… Read more »
Dear Charlene, nice story. My start was the same-in 2nd year of elementary school I discovered the thrill of grandma 60’s style garnments (bullet bra, nylins, controlling panty gridles, petticoats). By my oppinion she found out. The next year carnival my mother said to sprnd that weekend at grandma. On friday afternoon both told ne that they got my masqureade dress. It consisted of old granny lingerie and petticoat. Grandma even made a dress for me that went with petticoat. My mum gave me her wig and made my make-up. They got also some girls flats. I was in the… Read more »
Хубаво е да се чувствам жена, просто съм по мобилна.
Може би мъж да се чувства жена му/ми дава вътрешно удовлетворение и поне малко щастие.
Charlene, you and I are of about the same age. Your story of early life and the growing awareness of the female lurking within you closely tracks my own experience. My own “That’s me! That’s me!" moments came when A) I first learned about Christine Jorgensen in Sex Ed class in high school, and B) at around that same time, received, from a penpal in Britain,some British magazines which contained articles on a transgender actress/performer named April Ashley. The world of possibilities opened wide for me at the point . . . but I had absolutely no idea how to… Read more »
Hi Dana, thank you for your thoughts. I like you find a contentment in crossdressing, but it never is fulfilling, because I am not a crossdresser. I am a trans woman.
We are nearly the same age. I truly appreciate how you considered your responsibilities to your family and wife while all the time knowing who you really are. I am there now but also do hold out hope that lile you I can soon see my way to life as myself.
Kindly,
Charrie.
Welcome, Charlene. We are happy to have you around 🏳️⚧️💜🤍💙🤍💜
Charlene K My answer would be no, I didn’t know.I had been dressing for the better part of a year (2015) and attending CD/TG monthly gatherings in 2 places. One was an hour and a half from my home and the other was about an hour. One afternoon I was getting dressed to attend one of the events and my wife asked me what did I get out of dressing. I can’t remember my answer, but she said “You may be transgender.”. I had never considered that possibility before, but the more I thought about and the more research I… Read more »
Love ❤️ this. Thank you for sharing.