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Thread: Age and crossdressing

  1. #1
    Member steffigirl37's Avatar
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    Age and crossdressing

    I?ve noticed some conversations lately within this forum concerning older individuals and crossdressing. I am 66 years old and have been dressing for as long as I can remember . Started out raiding my sister?s closet, than my girlfriend?s and finally my wife?s. The Last 20 years or so I have developed my own wardrobe. Mostly through online shopping and with som help by my wife. Which leads me to a conversation we had a couple of weeks ago. Recently I completed an renovation of a two rooms and we were sorting through a lot of women?s clothes, both mine and hers. I tried on a lot of outfits that night, it was a lot of fun. We talked about the dresses I buy and which ones she likes and could see herself wearing. She than asked me if what I know today about transitioning would it have been something
    I would have pursued when I was younger. Over the past few years we know several children of our friends., as well as, a relative who are undergoing transitioning and we have talked a lot about it. My heart certainly goes out to them

    In the end I really couldn?t answer her question, even though at a young age I would wish I could be a girl, although I have never told anybody that.

    Right now at age 66 I still cross dress and I am very happy about that.

    Thanks for listening.

  2. #2
    Senior Member Maid_Marion's Avatar
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    Thirty years ago I remember a guy pulling me aside at the mall and telling me that guys aren't suppose to enjoy shopping!
    Prejudices like that made it a lot harder to transition back then.

    Marion

  3. #3
    Platinum Member kimdl93's Avatar
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    Its something I both imagined and feared when I was younger. It felt if giving in completely to the temptation might irreversibly compel me to transition (though I didn't have that word in my vocabulary in the 70s). Now, I don't really know. Its possible I might have been able to live a non-binary or gender-fluid existence, options I did not know existed at the time.

  4. #4
    Member AmeeJo's Avatar
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    I've been crossdressing for 43 years. I have always enjoyed dressing as a woman. I LOVE the way I feel when dressed. That being said, I have never considered transitioning. I like being a guy that occasionally dresses as a woman. I have been taking my dressing to new and previously unexplored levels but I still want to remain a guy. A very pretty guy....
    We can only achieve what we dare to reach for.

  5. #5
    Member Marissa Q's Avatar
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    Quote Originally Posted by kimdl93 View Post
    Its possible I might have been able to live a non-binary or gender-fluid existence, options I did not know existed at the time.
    The options have always existed; the terminology didn't.
    In point of fact, you knew that the options existed but, like most of us, were too bound up in the conventional social order to even consider standing out/apart. Social fear is directly proportional to one's need for social acceptance.

    Quote Originally Posted by steffigirl37 View Post
    In the end I really couldn't answer her question, even though at a young age I would wish I could be a girl, although I have never told anybody that.
    I'm loathe to point this out but -- given the remainder of your statement -- you very likely mean you wouldn't answer her question.

    -

    As for me, a crossdressing man in his mid-50s, I enjoy so many benefits of my bifurcated "lifestyle" that -- truth be told -- I'm unwilling to part with a single iota of both the masculine and feminine sides. I enjoy slipping into the gap between genders and thoroughly appreciate both. Transitioning has always seemed compelling to me in some sense but, as a bi-sexual male, I'm so obviously non-committal that transitioning to female might likely leave me pining for more masculine times. To boot, although I've had many relationships throughout my life (some quite long-term), I have always been opposed to marriage for the simple fact that committing "forever" to anyone seemed the most likely road to perdition, given a topsy-turvy sexuality. Thus for me, transitioning falls within the same level (or lack) of commitment. In short, even if I were 20 years old today but knowing myself as well as I do, I'd still be "undecided" whilst enjoying every step of that meandering gender path.

  6. #6
    Platinum Member alwayshave's Avatar
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    Steffi, I can't comprehend what I would have done 48 years ago when I was thirteen. It was so long ago and I'm so different. I enjoy crossdressing now and I'm satisfied with that.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  7. #7
    Senior Member Kris Burton's Avatar
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    As a young, quite naive, immature and shy person (now 50 years ago or more) I was not open to the possibility of crossdressing, much less transitioning. Still I was fascinated by both, and kept those thoughts deeply hidden within. I never wished to be female, and still don't. Sexual fluidity interests me now, but is not something I could see myself engaging in now - I'm married. Any change would require 20/20 hindsight,and although it would be nice to enter the wayback machine and relive those days without the constraints of my naivete and social ineptitude (much more than societal constraints for me) it can't be done. Having said all of that, coming to crossdressing at a late age as I have seems to fill a void in my psyche, and I agree with Ameejo when she says:

    Quote Originally Posted by AmeeJo View Post
    I like being a guy that occasionally dresses as a woman. I have been taking my dressing to new and previously unexplored levels but I still want to remain a guy. A very pretty guy....
    And it feels great!
    Last edited by Kris Burton; 03-26-2022 at 04:52 PM. Reason: wording

  8. #8
    Member steffigirl37's Avatar
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    I'm loathe to point this out but -- given the remainder of your statement -- you very likely mean you wouldn't answer her

    No I disagree. I couldn?t answer because I really don?t know. But I do believe most cross dressers at some point contemplate being or becoming a woman. Right now I am a man who likes to dress as a woman and I am ok with that.

  9. #9
    Member Fiona_44's Avatar
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    I have never had the desire to transition at all. I'm happy being a guy who enjoys dressing in women's clothes and the older I get the more I want to develop my feminine side.

  10. #10
    Senior Member Jenn A116's Avatar
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    I'm happy being a man. Wouldn't transition even if I was still 21 (or whatever) because I know what I am. But part of me is being a CD. I've finally come to accept that. I'm fortunate to have found a woman who loves all of me. We've been married now for close to 25 years. Yes, she is uncomfortable when I'm dressed but she knows its part of me and accepts me that way as well as in guy mode.
    Jenn A --- nothing fancy, just me.

  11. #11
    Member Jessax101's Avatar
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    Hi,

    Being over 66 and just beginning the thought and action of cross dressing is quite a challenging situation for me. I had really never considered dressing or making up 10, 20, 30, etc. years ago. Always was working at being masculine, but knowing inside I was bi?.when young, I had to teach myself to be masculine and a few times had thought I would be a better girl than guy, but never had tried on women?s cloths, wife?s cloths, etc., nor had applied any make-up. Had not ever considered transitioning.

    So your answer that u didn?t know how to answer her question seems like u really never had considered it and gave it much thought.

    Just beginning, I?ve used make-up and dressed several times, and I throughly enjoy trying to make myself look pretty and sexy. The first few times I tried, not knowing what or how to use make up, it was a disaster.. then the 4th time or so after reading tips from stylist and cosmetics companies, I actually made myself look 1/2 way decent, and it made me want more. (I have posted a pic on my profile but it does not show up on my replies to threads). Unlike you, I have no one to share or ask for help in cloths, cosmetics, etc. It surely must be a blessing to have that support and confident. I?m glad u are happy with your situation and hope I will be able to find comfort and joy in my endeavor. I am trying to take steps to guide and help in my journey, and so far these forums are giving me some help and confidence. Thank you for sharing. Jess?..

  12. #12
    Female Illusionist! docrobbysherry's Avatar
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    Exclamation I was ripped off!

    Since I didn't start having gender issues until I was in my 50's, I never had a chance to be a young woman or even a young CD!

    Which is why I'm compelled to present as a woman 50 years younger than I actually am!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  13. #13
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    I knew when I was 15 years old that I would not transition. The same applies today at 58 years old. I enjoy CD but do not have as many opportunities to dress as I used to.What convinced me was watching a series of documentaries in the UK called A Change of Sex. Originally shown from the late 70s onwards and recently repeated 40 yrs later. The documentary was the story of Julia Grant , her fight for transition, life struggles etc. She was a pioneer and active on TG scene but suffered immensely. I realised it was not for me and watching it 40 years later reinforced my view. Recommend watching it to anyone. Think it is still available online on BBC I player.

  14. #14
    Silver Member Maria 60's Avatar
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    My biggest problem back then was I didn't understand it, as much as I knew it was hormonel because once I would satisfy myself I would remove everything. The part I couldn't understand was when opportunity hit I would just feel relaxed and comfortable wearing a slip and pantyhose and watching TV or reading. The guilt was eating me alive back then, every time was my last time, just to do it all over again on the next opportunity. Once I got married and the first time I put on my wife's pantyhose was the day I surrendered myself and told my wife. It was my wife who put everything in prospective who once I explained everything to her from the first time I put on my sisters pantyhose to that same morning I put on hers. Surprisingly for some reason she didn't she a problem, her view point was as long as this was something I wanted to do in private, she was willing to help me. After about a year every time I would dress in front of her I would apologize that she had to see her man dressed like that, she told me to stop apologizing and stop flattering myself that I was not doing anything that bad. She didn't understand the guilt and told me as long as we both respect the line we drew in the sand that I should stop trying to figure it out and instead should just enjoy any opportunity I get. Knowing that now and thirty plus years later married I believe it would have been a easier youth if I did just as my wife say to enjoy it. I tried so hard to try to figure it out and feel guilty that I missed out on the beauty of it. Let's just say that I didn't figure it out but my wife and myself have enjoyed it till now. With age comes experience.

  15. #15
    Member ziggie's Avatar
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    I have never given any serious thought to transitioning but have wondered what it would be like to be a woman for some limited period of time. I just don't think it would suit me to make a permanent change.

    That said, it is interesting to hear the wide range of stories from different people. Infinite variety.
    So many new things to learn

  16. #16
    Aspiring Member Karmen's Avatar
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    I think we become more confident in our self over the years and we are willing to take more risk. I crossdress since my teens and now in my 40s, I go out sometimes also during the day in highly populated area like shopping centre, even I know I don't pass and with involving technology is more dangerous for someone to take photo or video and expose me on the internet than ever before. 10 or 20 years ago, most you could fear, was to stumble on someone you know and I didn't dare going out during the day.

  17. #17
    Senior Member GretchenM's Avatar
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    I was ready to transition when I was 7; that was 70 years ago. Of course I was willing to transition to anything if I could get away from being the boy that I was. Hated it. It just seemed to me being a girl was probably the best I could do as other creatures were a larger stretch. That said, being a girl was very attractive to me. I liked girls and loved being around them. But all of that desire faded in a few years and I decided being a boy and then a man wasn't all that terrible if I could once in awhile be as much a girl as I could be. It was a very rocky road though and not a lot of fun. The last time I considered transition was when I came out 10 years ago. I have been through many phases since then and explored every little side canyon I came across in the quest to find the "real me," whatever that is.

    Like Marissa, I have adapted to the age factor and a pile of other factors and now live in the in-between world, picking and choosing what, for the moment, seems to work best. It works great for me and allows me to gather together the best of both worlds. Not everybody is on-board with this, but it is a good fit and even those who do not tolerate it fully are fairly "live and let live" about it because it creates a gentleness in me that is hard to be too critical of, especially when compared to by dysfunctional masculinity of the past that was that way because it was a disingenuous simulation of maleness that had a foundation the size of a pinhead.

    Dressing is just a minor, yet important, part of the total package. For me it is about the attitude and behavioral aspects and how I interface with the world around me. The harsh domineering masculinity is almost totally gone and it has been replaced with a softer more female-like perspective and attitude. That is not to say dressing is not enjoyable anymore. It is, but it is a much rarer event than in the past. The desire to transition is nothing but a memory now because, in a sense, I have transitioned and to a significant degree I am the person I fantasized about being when I was 7. To me, transition does not mean going to the opposite because to me the opposite does not exist. I believe we are all composed of a unique blend of male-like and female-like characteristics - the Gender Mosaic.

    Slow learner? Not really; it is just that when you are not gifted with a clearly defined and larger more cisgender-like identity it is hard to find a place for yourself that makes sense in the ambiguity of an identity that tends to span the gap between the gender binary concepts held by most people. Psychologically it can be called an undifferentiated gender identity. But it can also be called all sorts of other things as well by the experts. Whatever it is called, it is all yours and if it is configured as a kind of "shape shifter" that is OK; it is just harder to find the differentiation you seek when gender variant.

  18. #18
    Aspiring Member DianeT's Avatar
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    I never considered transitioning but when younger I had fantasies of being a young woman (yes, not an old hag, how surprising). They were just fantasies born from my curiosity of feminine things and teenager rising sexual excitation. As an adult I can still imagine being a woman at times, but it's more a mind experience, trying to imagine what it would feel to be that female in that context at that particular time after I saw a picture or real life situation that made an impression on me, and not "being a woman" in the general sense. Since I don't really picture myself in these mind experiences but just imagine being that person, my age has no bearing on it.
    However my age (50+) has a bearing on my looks as a crossdresser. I have two wigs, chestnut and copper blond. The first feels beautiful and natural as it is close to my actual hair color, and the second is cool and more fun. But I am considering buying a third one, ash blond or downright gray, to get a look both classy and more consistent with my age. I really think it would look neat with a business suit.
    Last edited by DianeT; 03-27-2022 at 08:42 AM.

  19. #19
    Rural T Girl Teri Ray's Avatar
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    I am 67 and have been crossdressing to some extent my whole life. As for knowing what I might desire to do as far as transitioning goes if I were my same person in todays society is difficult to answer. During my youth I did have dreams of becoming female. Looking back I find that if anything would be different is I wish I would have come to peace with my crossdressing desires much earlier. Once I finally accepted myself as a crossdresser I became so much more at peace with my self. I like many others here I find being able to slide between dressing as a woman and just being my male self is where I desire to be. I am happy with my life and looking back I would not change my path except for learning much earlier to accept my crossdressing desire. Interesting question to say the least.
    Teri Ray Rural Idaho Girl.

  20. #20
    Member steffigirl37's Avatar
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    Great comments. I really appreciate the time you all took to express your opinions and your ability to do so is amazing. Something I am surely lacking. It has certainly put a positive aspect on my thinking.

    I sincerely thank you all.

    Steffi

  21. #21
    Exploring NEPA now Cheryl T's Avatar
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    If I knew then what I know now I don't think things would have changed. I simply didn't have the strength of conviction back then to transition.
    If I were in my teens Now and had the access to knowledge and services that are currently available I have no doubt that I would be transitioning. Things are so much more available and so many more people are accepting.
    I don't wear women's clothes, I wear MY clothes !

  22. #22
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    Very nice post Steff...
    I have been dressing since I can remember. playing with my sister dolls and invading her closet, moms when no one home. Got along with girls and boys, played all the sports but always had special feelings when with the girls. When dating began, I was just as much interested in the clothes as what was in them. never told anyone including my wife. That happened much later when I could no longer keep the topic from her. I am 72 soon, married 49 years and crossdress whenever possible. Would I transition, yes if were years ago.

  23. #23
    Oh to be an English Rose Jane G's Avatar
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    Finally in my 60's cross dressing is enough for me. Or maybe the effort of transitioning is too much. Either way I am content with who I am and where I am. Since I retired from work I can be me, pretty much when ever I choose. It seems I choose to go rock climbing and driving my sports car, more than I choose to, stay home and dress. If I was once free to climb and drive as a woman, then I probably would enjoy those things even more. But that will never be where I am. Where I am I except I enjoy and I live.

  24. #24
    Aspiring Member April Rose's Avatar
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    Lightbulb

    Quote Originally Posted by

    Slow learner? Not really; it is just that when you are not gifted with a clearly defined and larger more cisgender-like identity it is hard to find a place for yourself that makes sense in the ambiguity of an identity that tends to span the gap between the gender binary concepts held by most people. Psychologically it can be called an [B
    undifferentiated[/B] gender identity. But it can also be called all sorts of other things as well by the experts. Whatever it is called, it is all yours and if it is configured as a kind of "shape shifter" that is OK; it is just harder to find the differentiation you seek when gender variant.
    This resonates a lot with me.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

  25. #25
    Member Mackem Sue's Avatar
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    Quote Originally Posted by AmeeJo View Post
    I've been crossdressing for 43 years. I have always enjoyed dressing as a woman. I LOVE the way I feel when dressed. That being said, I have never considered transitioning. I like being a guy that occasionally dresses as a woman. I have been taking my dressing to new and previously unexplored levels but I still want to remain a guy. A very pretty guy....
    This sums up me too. Transitioning isn't and has never been on my agenda.

    Mind being more passable so I go out in public without being noticed would be nice.

    Sue

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