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Our Saturday dose of wisdom.

It’s funny how often folks come to me, almost in a panic, going, “What if I just can’t seem to pass?” They’re really stressed, thinking they’ll never embody femininity convincingly. 

But I tell them about my neighbor, Frank, a guy as sturdy as an oak tree, who managed to exude a sort of femininity with some smart wardrobe choices and a bit of shadow here and there. 

It’s essential to remember that femininity isn’t one-size-fits-all. Look at Carla. She could be a stand-in for a heavyweight boxing champ! But that doesn’t make her any less of a woman. 

Sometimes an old-school armoire has more curves than she does, especially when she’s decked out in her usual plaid and denim. 

I often hear from people who are down because they didn’t start exploring their gender expression sooner, like in their teens instead of their golden years. 

While there are indeed some eager beavers in their youth, genuine comfort in embracing this path often doesn’t come until later. 

Think about it; being in the prime of youth is one thing, but having the emotional maturity is a whole different ball game. The seeds of exploration are planted early, sure, but real growth usually needs a bit more time.  

With the wisdom of years, we often become more at peace with who we are. We navigate life, learning, stumbling, and gradually unveiling aspects of ourselves previously kept under wraps. 

That unveiling might be cautious at first, but it gains prominence as we age. Sure, adopting a youthful style has its charms, but it’s somewhat superficial. Most people find a richer, more authentic experience with crossdressing as they grow older and wiser. 

At some stage, masquerading as a college kid becomes a stale pursuit. It’s more about embracing our actual age, and finding pleasure in expressing ourselves within that frame. It’s meant to be a joyous, liberating journey. 

That’s my role here, to guide and uplift. With that being said, dressing your age is fine but if you’re able to pull it off and use fashion to transform yourself then go for it!  I’m blessed to some extent to be able to wear lots of variations in fashion, hair color etc. 

I often suggest looking for role models among contemporaries, women who carry their years with elegance and flair. Emulating the flashy looks of young idols or provocative stars doesn’t really work if you’ve celebrated more than four decades. 

The key is relishing the art of dressing up. It’s about patience, continuous effort, and you’ll find yourself improving. Given the right mood, a touch of cosmetic magic, and a dose of confidence, you’ll become more adept at passing. 

It’s a journey, indeed, but discovering that authentic look that resonates with your inner self is profoundly rewarding. 


5 Responses

  1. So well stated Gwen – and I can relate to everything you say! I have found that crossdressing now in my later years has an uplifting and “youthening” quality that gives me a euphoric lift as I transform into my alter ego. Inspired by the wonderful presentations around me, I am not regretful of the years I missed, but rather appreciative of what I have now and the adventure ahead of me. I am the better, more well adjusted person for all of this – and wouldn’t have it any other way.

  2. So much of this goes to that fear factor
    I’m pretty sure it’s happens to all of us
    The what ifs questions
    Yes for me it took some time but I did finally overcome that fear and realized it’s just me being me and it really doesn’t matter how others see me
    Yes I want to put on my best presentation of a women that I can, but at the end of the day I’m just a trans women and that’s just fine

  3. Hi Gwen,
    You are totally correct. Everything you stated is spot on.
    I guess I’m one of the lucky ones in that I started going out in public when I was I was in my late teens in the late sixties. So I had everything under control by the time I was on the back nine.
    I also agree about dressing the age you look and not the age you are. If you’re lucky enough to have a slim body and not a lot of wrinkles and look to be in your late 40’s rather than your late 60’s then by all means show them what you’ve got in a classy manner.

    Trish ❤️

  4. I first went out in public enfemme in 1980. I was in my early 30s. Needless to say things were different back then. When I go out in public I dress to blend in. I think passing is a matter of percentage for many of us. I enjoy every time. I dress appropriately for the occasion and location.

  5. Gwen,
    For occasional dressers there is an overwhelming urge to dress to the nines which often means a role model that may be much younger with perfect makeup and stunning outfits , in that context ” passing may not be the criteria .

    While we say there are no rules the more we dress the more we feel the need to pass . The example you give is an ideal example of proving women come in all shapes and sizes , once we understand and accept that point we can form a more acceptable way of achieving our goal .

    We must also accept not everyone wishes to pass , they just love the art of dressing . Others know they can never pass and deal with it by saying , ” this is me , warts and all , if you don’t like it that’s not my problem !”

    Personally my desire is to lose the man , I feel hurt and disappointed if I’m considered a man in a dress , thankfully the only one who has accused me of that is my ex-wife ( which is understandable but unnecessary ).

    Being full time obviously comes with it’s problems , I admit I retain my male abilities which means certain jobs require a more working approach with my appearance but it’s still possible to look female . Many of the traditional male trades are now performed by women , which is great to see and the bonus is we can blend in far better when performing them .

    Dealing with gender issues at a younger age is possibly a subject for another post . For the majority of us ( especially more mature members ) most would admit there isn’t a right time to come out because most of us have comittments . We marry , buy a house usually with a mortgage so we need a steady income to support that and then the addition of children . I often ask myself would I have done any differently ? Does the acceptance of gender issues come at a price at a younger age ? Would I have traded my children and grandchildren in pursuit of my correct gender , would I have been any happier ? To quote Amanda , ” I’ve found my sweet spot ” , what I have now is as good as it gets .

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