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Thread: For Cross-Dressers: Would You Transition If You Could?

  1. #1
    New Member april1978's Avatar
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    For Cross-Dressers: Would You Transition If You Could?

    Hi everyone,

    I?m reaching out with a question that?s deeply personal to me. I?ve identified as a cross-dresser for a long time, but the truth is? I?ve known since I was around 10 years old that it was always more than that. I just didn?t have the words, or the safety, to say it.

    Recently, I cracked my egg. I told my wife. And I?ve admitted?to her and to myself?that if the path were clear, I would transition.

    So I?m asking, from a place of genuine curiosity and zero judgment:
    ➡️ For those of you who consider yourselves cross-dressers and not trans?if there were no barriers (social, medical, financial, or family)? would you want to transition?
    Or is your connection to femininity something else?expression, play, release, identity in its own right?

    I?m trying to understand where I fit on this spectrum. Thank you for your honesty and openness?it really means something.

  2. #2
    Miss Conception Karren H's Avatar
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    1) I still don’t know what I am so I don’t know if I can answer the question or not.
    B) Anyway, I probably would transition if I were younger. At this late stage of the game I don't feel it?s worth it an more.
    Last edited by Karren H; 06-26-2025 at 02:38 AM.
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  3. #3
    Silver Member Kris Burton's Avatar
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    I am not interested in transition, never have even considered it. I believe that desire comes from a different mindset than I hold. For me the duplicity or perhaps fluidity of gender is a big part of the attraction. However, if I could fully and physically switch back and forth at will, that would be interesting!
    www.flickr.com/people/194195593@N05/

  4. #4
    Connie Connie D50's Avatar
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    My very short answer is yes.

  5. #5
    Platinum Member kimdl93's Avatar
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    I know this question was directed towards cross-dressers, but after decades of life experience and some contemplation, I honestly do not know if there is a line between cross dresser and transgender, nor which side of the line I am.

    Like Karren, I feel like it?s very late in the game. That is speaking strictly for myself. I admire those who are less risk averse and willing to take on the challenges of transition at any stage in life.
    O wad some Pow'r the giftie gie us
    To see oursels as ithers see us!

  6. #6
    Member HelpMe,Rhonda's Avatar
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    When I thought I was 'just' a crossdresser I'd answer this with either 'yes' or 'if I could change back' and not relating to people who answered 'no' was one of many indications that I was more trans than I was allowing myself to ponder.

    (when this egg crack happened here it didn't matter that the path wasn't clear)

  7. #7
    Senior Member SaraLin's Avatar
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    I consider myself more on the "trans" side than I do "CD" so I'm not sure if my opinion counts.
    Here goes anyway:

    There is another barrier that you didn't mention and it's the one that kept me from transitioning. That barrier is "physical."
    My hands, Feet, and height (to name just a few) are things that no amount of surgery could correct.

    Now, if it were possible for me to successfully and FULLY transition, then yes I would.
    It's not, so I didn't

    Your own posting has your answer, though. You told your wife that if you could, you would.
    You sound rather like me - conflicted. You see the outer reality of your life but also know your inner sense of self.
    The two just don't match, do they?
    All you can do if decide for yourself what to do about it.

    As for me, I chose the "easier" (and safer) route.
    Most of the world only knows the male me. In the non-digital world, only those I love and trust even know about me as Sara. Even fewer have ever seen me fully femme.

  8. #8
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    According to my wife I could transition if I choose too. But as much as I've always wanted to be a girl, I'm very happy just living as I am.

  9. #9
    There's that smile! CarlaWestin's Avatar
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    I can certainly go with being happy living as I am. Your question might very well be would you subject yourself to major surgeries and a lifetime of pharmaceutical maintenance to go along with the crossdressing to present as female 24/7?
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  10. #10
    Aspiring Member Philippa Jane's Avatar
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    Hmm. A different mind set here.
    I always just thought I was a crossdresser and that was probably down to a lack of information.
    The constraints all fall around our age and our social standing.
    Take those away and what is your answer now.
    Crossdressing is an expression of your feminine side. Of loving the feel of certain clothes and for some it is a fetish. No judgement here.
    Transitioning is so much more. It's not so much about hating your body but wanting the body you feel you should have had from birth.
    That feeling when you are socialising with women that you are accepted as one of them.
    It is never just the clothes it is more mental and that feeling of peace.
    .


    Philippa Jane

  11. #11
    Silver Member Jenn A116's Avatar
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    At the risk of falling into the abyss of what to label people, I'd say no as a crossdresser. I enjoy dressing, but it's not how I live my life. Transitioning would dramatically change that.
    Jenn A --- nothing fancy, just me.

  12. #12
    Gold Member bridget thronton's Avatar
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    I am not a fan of surgery - so no for me

  13. #13
    Aspiring Member Marketa's Avatar
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    Honestly I played with this question recently and as I am much happier en femme, especially with full make-up, I was thinking, what is the biggest obstacle and realized it's money.

    You saw my photos and my build isn't particularly big and manly, I'm not that much afraid of surgeries and my life is built in a way I could do it without repercussions. I would just hope I would get some hips and I would hide my shoulders with long hair.

    So yes, I would go for it without much doubts.

  14. #14
    Silver Member CynthiaD's Avatar
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    Social transition, yes. (No surgery or HRT) I?m heading that way now. I could see HRT, but no surgery.

  15. #15
    A Brave Freestyler JohnH's Avatar
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    For me to transition would be difficult as I have a deep voice. In the morning I can stand in front of a mirror and see a woman looking back. The I sing with my relaxed vocal cords and the sound of an oktavist comes out, thus shattering the illusion. In that state I could easily sing the second bass part of Rachmaninov's Vespers. I do not want to compromise my voice as I am the only singer in my church choir that can sing ledger line notes below the bass staff.

    John
    John (Legal name)

  16. #16
    Aspiring Member
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    I recently turned 70 yrs old.
    If we had the internet 55 years ago and had the information then that we have now
    I think I might have bit the bullet and at the very least socially transitioned.
    I would have never married( although my wife of 41 years is a great person and
    has tried to understand my struggles)

  17. #17
    Aspiring Member Georgina's Avatar
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    No. I am a man and I want to remain a man. I like wearing skirts and dresses and probably appreciate the clothes more as a man.
    I don't wish to change my gender I just want to change my clothes.

  18. #18
    Girl Power! CrossKimmy's Avatar
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    I absolutely would
    Ladies & Gentlemen, HER. 💋🌸💗

  19. #19
    Aspiring Member GracieRose's Avatar
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    In my mind, I'm transgender. No ifs, ands, or buts about it. I spent my life denying that fact. I knew that I was transgender since I was in kindergarten, but I was constantly told that I was wrong, so I spent my life mimicking what I was told to do to present as a male. At this point I have a wife, children, and grandchildren that I dearly love. I would love to transition (the answer to the prayer that as a child I often voiced at bedtime to let me wake up as a girl). However, I believe that the many people that feel the need to enforce a simple misguided gender binary and challenge the very idea that I am who I am would present a clear danger of harassment and possible physical harm to my loved ones if I transitioned. I think that I'd accept that risk myself, but I'm not willing to expose my loved ones to it. So I reconcile my life to enjoying being my true true self occasionally. One might see that as "merely" crossdressing. If societal expectations were to mature and reduce that risk to my loved ones, I think that I'd transition in a heartbeat. However, with less than 3 decades left in my life, I don't expect that to happen in my lifetime. In the mean time, I'll do what I can to help move society forward so that others in the future can be themselves without repression.
    -peace
    -Gracie

  20. #20
    Platinum Member alwayshave's Avatar
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    I am a crossdresser, ave have no need or desire to transition.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  21. #21
    Super Moderator Raychel's Avatar
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    Not for me for sure. I am totally happy where I am at.
    I enjoy dressing, but that is the end of it for me.
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  22. #22
    Member Meg's Avatar
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    Back in the sixties when I first heard of Dr. Renee Richards, I hope I spelled that correctly, it certainly came forefront in my mind. If times had been different back then, I probably would have. Society is more advanced now, but unfortunately for me, such a change is not in the cards for me now.

  23. #23
    Aspiring Member
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    I have often thought about this but being in my late 70s I don?t think its ever likely to happen.
    However, I have undertaken several quite challenges for charity and vaguely thought about planning a year en femme to raise funds for an appropriate challenge.
    The downside would be the possible media attention it might attract ? plusses and minuses.
    And if it turned out I liked it, would I want to return to maledom.
    Vikky
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    Adventure before dementia

  24. #24
    Member Keremy's Avatar
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    Absolutely not. I love being a man and I love wearing dresses. If I could choose my wardrobe to fit me I would have a couple man outfits in my closet and the rest would be dresses and pretty things but stripped down I would still always be a man. Wish the wife would understand that

  25. #25
    Member HelpMe,Rhonda's Avatar
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    Supposedly only 20-25 percent of trans women get 'THE SURGERY', for various reasons.

    I do have the 'lifetime of pharmaceutical maintenance' ahead of me, but nowhere near as many (presumably lifetime) meds as the cis person I married 20 some years ago. But yes, most trans women (somewhere from 70-90%) do that pharmaceutical maintenance.

    And there are trans women who do either or both of those things that don't socially transition.

    There's no 'there's only one way to be trans' rule that says you have to do all three.

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