Honestly Geraldine, why do you need to crossdress?

This is the very tentative first step by a somewhat bewildered ordinary man who discovered that at sixty years of age, I needed to crossdress.

I hope to develop this site to include aspects of my journey so I can better understand it myself and figure out where this new side of me fits with what I previously thought was the complete me.


14 thoughts on “Honestly Geraldine, why do you need to crossdress?

  1. Just found your new site and wanted to encourage you to post some more. I found blogging real helpful in exploring and coming to understand how I felt. I hope you may find the same. Good luck.


  2. Thank you Antonia Michelle for your comment. It has steeled my resolve to expand the site which I am sure will clarify for me some parts of me and my life. Sometimes all we need is someone to prod us into action and for that I am very grateful to you.


  3. Hi Geraldine!
    Thank you for following my blog, I hope to be posting more soon.
    Please be brave and put your thoughts out here, I’m sure you’ll start to find it therapeutic, and you’ll receive lots of support from others of us in similar situations; people of all ages too.
    Wishing you happiness.


    1. Thanks Tish for taking the time to post. The fact that a kindred spirit is encouraging me to tell something about my personal growth buoys me with more courage and yes I will tell my story soon. I also look forward to following your interesting and exciting journey.

      Liked by 1 person

  4. Greetings Geraldine,

    May your inner beauty shine forth as a new birth into a world that needs more femininity. Welcome and may God richly bless your journey.


    Liked by 1 person

    1. Gin,thank you so much for leaving this message. While Crossdressing and transgender comes with difficulties, I definitely accept it as a humbling blessing, meant to improve me and therefore the world. I think it shows God has a lovely sense of humour.
      Yes a little more femininity could not go astray.
      May you also see God in your journey.


  5. Good afternoon,
    Your probably not older than I am & I have done some kind of crossdressing / transgender thing most of my life – going on sixty years. So, I am surprised that this compulsion has struck you so late. Although I had a successful career of more than 30 years and have three beautiful children, two step children and a bunch of grandkids. I have always been active in the Catholic Church and the community. And yet somehow, my crossdressing has, in my eyes, defined me.

    The Franciscan Richard Rohr writes about the second half of our lives – not necessarily chronological – we don’t all find it. In that second half, we give up our false self and find the person we truly are. We learn not to care that we are flawed, even though society continues to ask us the conceal much of ourselves for fear of losing friends and family. But the more we can at least accept who we truly are within ourselves, the better and more fulfilling our second half will be.

    If you haven’t already found it, I suggest you access . It is an excellent site and provides really upbeat and insightful commentary and genuine professional counsel. I would particularly point you to their essay on “andropause” male mid-life. This may explain some of your recent changes. I really got a lot, years ago, on the essay regarding gender euphoria. I now know how crossdressing affects my fitness. I get a high similar to that I get from running because of the endorphins generated. Kind of explains why a crossdresser might continue to crossdress, but maybe not why he began.

    As I write this, I am retired for the third time and working on projects around the house and generally being a good house-husband. I dress whenever I can and often go on errands dress androgynously. Although I may be deluding myself, I have let go of any guilt. I love appearing, if only to myself, like a woman. Looking as good as I can motivates my fitness routine and I know how I can kick up those endorphins when I don’t have time to run.

    If you are truly brand new to this fantasy, I wish you the best. While some would define it as an illness or a character flaw, I feel blessed that this is my primary addiction when there are so many that are so destructive.



    1. Dear Falecia, I just cannot believe your response. It is something I can relate to in every detail. I am a Richard Rohr devotee and subscribe to and read his meditations.
      Yes, the need to dress really did first hit soon after I retired and while it is difficult, my life is so much the better for it. I am now a much more complete me and probably healthier too.
      I will respond more fully to your kind post but wanted to reply quickly to your very courageous message.


  6. Thanks for following me, and as the others said, I’m also looking forward to what you ‘discover’ about yourself, and what you will be writing here.

    I also agree with Falecia that there might be an influence from the mid-life crisis which will prompt a stronger urge to crossdress. Because I started crossdressing when I was 25 or so — a bit over two decades ago — I’m pretty sure that, in my case, it was something that would run much, much deeper than that. However, it’s clear now that, with 47 years of age, and a depression which took hold of me for two years or so, making me unable to work, but only desire to present myself as a woman (as much as possible), there must be some correlation between everything. In other words: while I might have been able to repress/suppress my urges for many, many decades, there was a point in my life when I simply couldn’t stand it any longer.

    I’m now at a phase where I cannot trust my own mind about what crossdressing means for me. This is mostly a result of some introspection, and the realisation (aided by my wife!) that what I think and believe is not necessarily tied to reality. I know this sounds very strange, but what happened was that my wife noticed that I started doing things much slower than before — but in my mind I would take exactly the same time as before. Of course, the clock would not lie: my wife was right, it was just my mind tricking me. Believe me, that truly shocked me, and soon I noticed other similar things which simply weren’t right. That was what prompted me to start talking to doctors — specialists in both clinical sexology (because of my gender issues) and, of course, understanding what it causes in terms of gender dysphoria, depression, anxiety, compulsive-obsessive disorders, and so forth. What was simply astonishing was that a latest-generation anxiolytic that they prescribed me suddenly turned ‘irritating’ experiences (like, say, my cats running wildly around the place) into ‘amusing’ ones. This was something my wife also immediately noticed: that after two weeks I started laughing at things that once would have driven me nuts. And the truth is that I laughed at similar things for all my life (including at myself!…), but it was the combination of gender dysphoria/depression/midlife crisis, triggered by a lot of things at the same time, which were starting to affect my mind.

    It was not easy to ‘accept’ that. But you know, after reading so many things for years, namely that when you believe you’re the only person who is right and that the rest of the world is wrong then something must be wrong with you… I truly stopped trusting my own mind. Fortunately for me, I’ve got some Buddhist training — not good enough to be able to discard my core beliefs, but good enough to be very open-minded about it, and to understand that what I felt that were ‘deep convictions’ or even ‘personality traits’ might, in fact, have all been linked to gender dysphoria and depression — and this has been going on for decades.

    That’s why I have this strange feeling when I talk to doctors. Before medication, when they asked me: ‘Are you a woman inside?’ I wouldn’t hesitate and say ‘yes’, explaining, however, that I spent all my life trying hard to comply with a male role, and that’s why I’m not especially feminine — but that doesn’t mean that there isn’t a ‘suppressed woman inside’ which wants to ‘come out’. That was, indeed, my conviction. Did that make me transexual? No, but certainly something along the gender spectrum.

    After two years of medication and therapy, it’s clear I have to keep an open mind about all these issues. Now I answer doctors saying ‘I don’t identify with the male gender role and never did’. Does that make me automatically female? No, unless you truly believe in binary gender, which is not the case. So clearly the crossdressing has to do with a certain refusal of staying in the male role all the time; is it merely an escape, a fantasy, or something more? I still don’t know.

    Many doctors ask me if I would like to change my body and be a female all the time. I hardly want anything else; but I’m also a reasonable person, and I’m fully aware that there are no jobs for transexual women in my country (unless you’re fine with selling your body on the streets — which, after a certain age, is not even feasible any more). It would also mean getting rid of family, friends, a place I call home, and probably move someplace else. I’m really unwilling to get rid of all of that — it’s simply too overwhelming to contemplate. In some countries, transgender people in transition get a monthly subsidy to survive until they can get a job; but not here in my country, so that’s simply not an option — I mean, even presenting as a male, I’m currently unable to work due to depression, how much worse would it be to be depressed and a trans woman, with no hope of getting a job? So I label all these jobs as ‘wishful thinking’ and forget about it: they are simply unreasonable.

    But if I do that, then I seriously need to consider all the other issues, and think if they’re truly ‘real’ and ‘important’. Doctors love to know if you’re willing to chop your dangly bits off. Seriously, I have absolutely no issue with that. My libido is zero, and has been so for well over a decade, and it has always been very low before that, except perhaps during my teens — and no, I didn’t even have a girlfriend back then, so all those hormone-induced passions were pretty much useless. So if that means getting surgery that will not allow me to have an orgasm ever again (which is highly likely), well, who cares, I count myself these days as almost asexual anyway — and whatever I’ve got between my legs will not change things much. Sure, I always wanted to have female genitalia, but not truly because of the potential of getting multiple orgasms or any such fantasy; it’s mostly because ‘it feels right’. However, once again, I need to be reasonable. All those trans girls on YouTube that look like supermodels rarely, if ever, talk about their recovery period after surgery; but I’m personally acquainted with two transexual women who have just been through surgery early this year. One, several months afterwards, still needs one of those rubber ring floats to be able to sit for many hours; she was weak and almost helpless for the first weeks, and only after two months she managed to venture out of the house. The other one, while not truly regretting her decision, after a few months is bit uncertain if that was the right decision or not. Well, let’s just say that I’m not exactly excited at the prospect of spending several weeks at home, pretty much useless and unable to move, and with lots of pain — and constantly risking all sorts of issues, problems and complications. It’s worth all the trouble? Sure — for those who either commit suicide or go through transition. It’s clearly not my case; after all, I’ve almost survived half a century without entertaining suicidal thoughts 🙂 and even when the depression was at its worst, I really had no suicidal thoughts, just a sense of frustration for nothing being ‘right’ in my life, more than half of it already wasted — but aren’t those exactly the kind of thoughts one is supposed to have during the so-called mid-life crisis?

    Anyway… long rant… sorry about that… it’s the way I am, always writing far too much! There is a point there, though, and it means being open minded to accept whatever happens and whatever insights you have about yourself; but also to allow yourself to take a step back and watch very carefully if what you’re doing is reasonable or not. There are lots of crossdressers who are exactly like that — for them, it’s not much more than a fantasy, possibly even a fetish, but certainly a form of expression, without which they feel ‘incomplete’. However, they have never a thought of regret, nor of frustration, much less enter a depressive state for not being able to crossdress as much as they wanted. Instead, they cherish what they do, they enjoy themselves to the fullest while dressed, but if they are prevented to do so, that won’t affect them much, either. And they don’t go through complex introspective issues about their gender, or what ‘gender’ means for them, and so on. Instead, they just have fun and enjoy themselves! I so wish I could be one of them 🙂

    Liked by 2 people

  7. I like your tag line of your post. I think it is open to humor, and I always like the addition of humor, when it is not degrading or negative. Having been attracted to the feminine, (activities, emotions, presentation) for over 60 years, I can suggest that it may begin with cross dressing, but is was the tip of the iceberg.
    Being confined to the closet for years, by the familiar constraints of career and family, I denied myself as much as I could, but ultimately it could not be denied. Once I reached the point where I could dress freely, I found I needed to be seen and accepted by others, and it was I like I had jumped from a precipice and there was no other option but to go with the fall, and hope to land safely. This time was often one of fear and anxiety, but having once found acceptance, as my femme self, the addiction was complete.
    I am very fortunate to be retired and free to dress and present as I please most days, and although I don’t wear makeup and heels to mow my lawn, I shop for groceries, or whatever I need as my femme self.
    For most of my life I felt that at some point, I would get over this and my attraction to the feminine would subside. I say this to encourage you to enjoy yourself, whatever path it takes, it is your life to enjoy, and so often our true selves can emerge, once free from the chains of work and the routines we fix for ourselves in order to survive in this world.

    Liked by 1 person

    1. Thank you Carla so much for leaving a comment on my still embryonic blog.
      Humour indeed! I do this not to be dismissive of my need to live more honestly and express that which is feminine within me, but because I have to respond to this quite recent development in my understanding of what life is all about. Dressing as a woman? Why not a red sports car or something as predictable to explore who I am? At least people would have laughed but accepted such a choice.
      But coming out as trans? And the shock was just as big for me as it was for my family when I shared my insights with them. So a little self depricating humour was and still is called for.
      My family’s response was civil but in all the years that have since passed, not a word has been spoken and my decision soon after to tell them I would refrain from dressing was to stop their anguish which I was made aware of. But that decision only moves that anguish back to me.
      Your point about believing these feelings would one day subside never occurred to me. The need hit at close to 60 and I thought it was finally understanding myself and the world, not something that would subside.
      I am pleased you are relaxed in yourself in retirement. I too have been retired since six months before my revellation.
      Your kind exhortations that I should let my true self emerge is I know good advice. Even after all this time While I underdress all the time and wear women’s pink lycra cycling gear for my morning ride, I don’t dress. The few times I went out dressed were such wonderful memories of just being free; of realising this was me. No jokes, no humour. Me.
      And yes I will have to make some time for me which is a problem I face in male mode too. I cannot spend time for me. It is always for others and this is not other’s fault. It is probably me needing to be needed.
      Now if one doesn’t have to laugh at that, one has no sense of humour.
      Thanks again for making contact.
      I would love to hear more about your blossoming feminine side and your leap into it. Stay in touch.
      Kind regards,


  8. Hi Geraldine,

    I came to my gender identity at a late age myself. I know longer consider how I dress as crossdressing. I am wearing the attire that personally and socially matches my gender.

    Good luck on your journey.

    Liked by 1 person

  9. Hello Stephie. This realising a previously unknown side of you later in life is a surprise to say the least. I remember as if it was yesterday thinking, how can everything I learned about myself over a lifetime suddenly be only part of who I am.
    In the new light of discovery, and in retrospect, maybe the birth of the feminine realisation made sense of some things that did not completely fit in the all male me.
    And this birth comes at considerable cost. But I presume you would agree that our greater understanding is worth it.
    Ever since the day I realised there was more to me than I had ever guessed, that understanding, that need to express my otherness has never left. It’s a bit late to expect it ever will, now. A gift I cannot return and one I would not want to.
    I hope your life continues to be enriched by your realisation and I hope you are supported and loved by those around your as you go where you must to become what you hope for.


    1. Hi Geraldine,

      I feel that my femininity might have been masked by addiction at 11 until my 20s and depression and anxiety afterwards. Now thankfully these are completely behind me. Looking back through and past this black cloud I get a few glimpse of earlier feeling.

      I was happy before I came out to myself and now I am even happier. I truly love myself. Because of that I feel it is easier for me to take care of myself in body and mind.

      Thanks I’m sure it will continue.


      Liked by 1 person

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