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Thread: What would you do differently, if anything if you knew 20 years ago what you know now

  1. #26
    Aspiring Member ShelbyDawn's Avatar
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    So many have already said the same thing but I'd have to go back further, preferable to when I was eighteen or so but even thirty years.
    As for what I'd change, well, the clothes I'm wearing would be the same but it wouldn't be called crossdressing.
    I am Me and Me is OK!



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  2. #27
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    For me, in order to answer the question I'd have to go back fifty years. I'm 74. At 54 years old, nothing would have changed. My wife and I had "The Talk" when I was about 36. She said, if I wanted to join a support group, that was alright with her. Leave her out of it. I looked, but, there were none to be found. Maybe, I should have continued to search year after year. There are a lot of things I would have done differently if I went into "Mr. Peabody's Way Back Machine," and. cross dressing does not top the list. Maybe, I should ask my wife what she would have done differently forty to fifty years ago. Can't cry over spilled milk.

  3. #28
    Aspiring Member kellyanne's Avatar
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    Looking back 40 years, as I turn 60 soon, I would not change much CD wise - perhaps more effort at trying to date another CD and attending regular TG events.

    Being independent and a CD with many interests and seeing almost everyone around me divorce in the interim period - the choice of the single life is still best for me.

    One larger life thing I would change is more family interaction and more effort on my part to see my sister, mom and dad who are now passed on.

    I like to play the percentages and I can pick a date well but never had any confidence in picking a spouse.

    My UNI girlfriend, a pillar of the LGBT arts community, I thought would be CD tolerant but was not - being financially risk averse I decided then to only date and not cohabitate or marry.

    while nothing is perfect, things have went rather well all in all and I am almost always in a happy go lucky mood.
    Last edited by kellyanne; 01-02-2022 at 03:58 PM.

  4. #29
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    While I'm not quite as old as some, I still would have had a very difficult time with the resources & environment that were then available, family, friends, career etc, even if I had gone "all in" and successfully stealthed. I certainly appreciate the "you need to be true to yourself, or you'll be miserable forever" mantra that gets put out there sometimes, but I don't think it's quite as black and white as all that. I've been very lucky as it is in that I've been able to express myself to the extent I have within my own boundaries, and had a lot of flexibility being single/no kids, but that's also a loss as well, and certainly not something to aspire to.

    Do I look at the younger folks today with a little twinge of envy that the world and resources are much more available & accepting? Absolutely, I don't think I'd be human if I didn't, but by that same token, constantly thinking "what I should I have done differently?" is bad in the long term. We're not all on the same part of the spectrum, either, so I think answers are going to be different for everyone.

  5. #30
    Senior Member Glenda58's Avatar
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    I wouldn't have gotten married a third time. Not purged all my things. And maybe even transition to be Glenda full time.
    GLENDA
    I FEEL LIKE A WOMAN

  6. #31
    Senior Member TheHiddenMe's Avatar
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    About 20 years ago I told my wife I wanted to get some woman’s clothes (she already knew I was interested in dressing). She bought me some things, like a dress and a wig and shoes at my request (I was reluctant to buy my own stuff). I started dressing at home, and began to shop for myself.

    It took another 15 years to build up the courage to venture out on a regular basis.

    In the meantime, the public evolved so it became more acceptable to venture out dressed. While I wish I had started going out earlier, perhaps my reception would not have been as welcoming.

    Fun to think about, but absent a time machine, impossible to change.
    I'm Sun-Dee at Kandi's Land; read about my outings here:

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  7. #32
    Once upon a time... Veronica Lacey's Avatar
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    If the Wish would come true I wouldn't wish to do anything differently as then I may not have met my wife and enjoyed the good life that I so far have.

    But...for the sake of casual discussion and it's a fun little topic...

    Maybe slide it back 30 years prior to meeting my wife and I would have tried to explore more of the community prior to laying down roots and becoming established in life. Sure, we can generally always make a change any time we want. Having said that it would have been easier and a lot more fun to explore the cd world as a 20-something had I realized that anything was possible back then.

  8. #33
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    came out a little earlier to my new wife - she's good now so cant complain and the other thing....be patient and organize to mine or buy about 1,000,000 BITCOIN for about $100.......

  9. #34
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    The biggest challenge wasn't so much who I was twenty years ago, or what my mindset was. Rather, the world was a very different place, not very open or accepting when it came to unconventional gender expression. Now, if I were 20 years younger in today's society, my oh my the things I would do!

  10. #35
    Exploring NEPA now Cheryl T's Avatar
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    Let's push that back say 50 years or so.
    If I knew then what I know now in all honesty I would not have gotten married. I would have pursued this avenue to a much greater extent and in my heart believe that I would have begun to transition many years ago.
    But all that is for another life, a parallel universe or some episode of the Twilight Zone. As the saying goes, "If wishes were horses then beggars would ride".
    I don't wear women's clothes, I wear MY clothes !

  11. #36
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    Wow, the options that could have happened.
    I could have been a woman by now.

  12. #37
    Member DanielleCD's Avatar
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    For me the change would have been 30 years ago... before my first marriage.

  13. #38
    Senior Member Christie ann's Avatar
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    Let’s just say that if I knew what I know now at 20 years old, I would have tried to transition. We just didn’t know and thought we were alone. And now, it is not fair to my wife for me to come out and say I want to be a woman.

  14. #39
    Junior Member JustJennifer's Avatar
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    20 years ago, I was certain that my desire to dress was long gone and never coming back. Regardless, I should have been more forthcoming and upfront about it before I got married. But I assumed the past was the past, so I kept that piece a secret. In retrospect, that was a mistake.

    Honesty makes things a lot simpler for everyone, because everything comes out eventually, and it's one less story you have to keep straight. If your SO were to find your past to be unacceptable, the present is already on shaky ground and the future is even worse.

  15. #40
    Silver Member Geena75's Avatar
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    Twenty years ago I hardly ever got dressed beyond a pair of pantyhose once and a great while. If I knew then what I would be doing today, I probably would have sworn it off and vowed never to do it again.

  16. #41
    Aspiring Member fun4metoo2004's Avatar
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    To start with, I would have watched my weight/shape better. Committed to dressing without worry. kept my hair so i could grow it out. I shaved my head and am trying to decide if I want to grow it out again.

  17. #42
    Aspiring Member Lacy PJs's Avatar
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    Not sure that many things would have changed but for one, there are certain clothing items that I would have "stocked up" on if I knew that twenty years later, they would be pretty scarce.

    I have yet to find a good replacement for Sears Cling-a-lon thigh tops and really nice sheer peignoir sets are nowhere to be found today. But twenty years ago... they were already going out of style.

    Lacy PJs

  18. #43
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    I would have never purged as often as I did over the years. I still miss a sexy lace black bra, that fell victim. If I had said that in the beginning of this post I may never had written all of this other stuff.

    I am in the same position as many, 20 years, is not a long enough look back. When I was in my mid-teens it would have been the beginning of the eighties. That was not a good time to be open and anywhere on this spectrum. I think then was the closest I have ever really considered wanting to do more to transition into a female. Then I had not discovered that my depression was also linked to gender dysphoria. I was not accepting of myself, and still struggle now, but time has made me better. I married young in life. Actually, today is our 36 anniversary. I think first I would have approached this with her more like I just did last week. There is a difference in discussing and then DISSCUSSING. Then she had participated and was more accepting, and I dare to say had a different perspective on the subject. I would have understood that my crossdressing was something that became hard wired in my frontal cortex and that over time it would change, wax and wain, but would not go away.

  19. #44
    Gold Member Helen_Highwater's Avatar
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    It's interesting to read replies that talk of not getting married, of pursuing a different life path but as others have pointed out, things were different back then and to live full time would have been a far more difficult thing to do. Recent societal changes have made coming out so much easier and for me the upsides of being married are not things I'd throw away lightly. Our partnership has given us a comfortable life that I'm unsure I'd be enjoying had I lived a single life plus I'd have missed out on two wonderful children.

    So what would I do differently. Looking back I can see there were opportunities were I could have been more open with my SO, certainly early on in our relationship and so a better understanding of myself could have given me the confidence needed to "Have the talk". Just to be out of the closet to my SO would have made a huge difference but that also assumes that she would have been accepting of that in the relationship as we raised a family.

    All that said, it is what it is and I need to focus on the here and now while looking forward and re-evaluating now we're empty nesters just what to do and is now the time for that talk.
    Who dares wears Get in, get out without being noticed

  20. #45
    Administrator Di's Avatar
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    I find it fascinating to read everyones answers.
    Over the past few weeks we have had many more join here. I think maybe it might be with the New Year and reflection on your life.
    Cross-dressing is a unique gift and a part of you . Do not fight it and accept yourself and you will learn how to use it in the best possible way to lead a happy life.
    My advice for those not married yet, be open and honest learn from those here that 20 years ago ( for different reasons) did not. Makes a much easier life for everyone.
    Great thread, and all the newbies can learn from it.
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  21. #46
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    At age 66 i would need to go back 50 years to open up to my family about my gender issues.
    Pretty sure they would have disowned me.
    I would have rather been disowned at age 16 than the hell i have put both myself and my
    wife through.

  22. #47
    Member Wendy-Lyn's Avatar
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    20 years, eh?
    Well, I'm 64 now (just) and around 25 years ago my life turned to hell in short order and I lost almost everything I had, including my self-respect, and my desire to have any sort of relationship simply evaporated. It has only recently returned - and with a vengeance.
    So, to the question - what would I have done differently?
    I've given this a bit of thought, and I think I'd have probably bitten the bullet, come out, and transitioned.
    I think I'd have been a much happier girl today if I had.

  23. #48
    Junior Member AnelineM's Avatar
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    If I could just call or email my 20 years ago self, I'd say forgetabout purging. You're not going to quit dressing up. And, SELL ENRON!

  24. #49
    Super Moderator Raychel's Avatar
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    It would have to be more then 20 years ago for me
    18 years ago I told my then wife. Not much has changed since then. I separated from my wife. But that is about all

    30+ years ago, I would have accepted myself more.
    I would have still been very careful who found out and who knew. I was a very well known business man. And had to be very careful about family reputation.

    But knowing how my wife and kids accepted. That part certainly would have happened sooner
    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"

  25. #50
    Just another 'Gurl'
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    20 years ago was a good time for me with CDing. However, I also wanted to return to the military which I did, necessitating a return to the closet until I eventually retired.
    Just another man in a dress

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