The title is pretty self explanatory, particularly to crossdressers. We have no idea why we do it, how we got to where we are, other than we like it. We like the feelings it brings us, the utterly “right” way we feel when dressed; The Joy. We also experience the downside; the guilt, the feelings of inadequacy, of self-reproach, the purging, and all of the regrets; The Curse.

I have been crossdressing since I was about 12 years old, and as my 60th approaches, that puts it at about 48 years, and counting. I think if we could convert the history of every crossdresser into a road map, and put each individual map on top of one another, they would mostly turn out to be the same. Thousands and thousands of roads would be eerily superimposed clearly upon the other, with thousands more deviating occasionally, but not a whole lot. Each of our colourings would stay fairly well inside the lines. There isn’t a need to rehash this; every crossdresser eventually will come to a similar conclusion.

I did mention that I am almost 60. That has brought with it a certain heightened level of examination and evaluation of my life that I think most people go through as they age. The looking back and reexamination of our past, seeing if you “made a difference” to anyone, if you accomplished anything of note, what your personal “legacy” will be, and whether or not you’ll have regrets (that’s the biggie for me).

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I recently heard someone during a radio interview (not connected with crossdressing at all) say that the worst thing they could imagine is to not like who you are; I agree.

In my retrospective musing, I can say with brutal honesty that crossdressing has had a very negative impact on certain aspects of my life. Sometimes to the point where I feel that worn out phrase “my life is ruined” running through my head. So yes, I have regrets.

Crossdressing cost me one marriage, while another periodically hangs on life support. I don’t think that’s too extreme. There were other factors at play, but I believe that if I were not a crossdresser, I would not have been separated and divorced from my first wife and children. What it has and will cost me regarding my relationship with my grown children, who essentially saw their parents split, but were never told why and never observed anything to cause a split (no substance abuse, violence, or domestic conflict), has most certainly come with a cost. During the aftermath of the bitter separation and divorce, the crossdressing issue was regularly thrown in my face, used by my ex as ammunition against me, either in direct derogation, or as spiteful innuendos in the emotional war fought for our children’s loyalties. Crossdressing references found their way into the court documents as well.

Perhaps if I had simply cheated, or was a mean drunk, used the family income for drugs, my ex would never have felt that hurt, disappointment, disillusionment that has fueled her actions since we parted.

On my ex-wife’s behalf, Rikki didn’t make an appearance to her until shortly after we were married and before we had children. That was a disaster, and any evidence of Rikki in the marriage from then on was limited to the occasional sighting of her stockings, lacy bras, or heels (much higher than the ex owned) carelessly forgotten to be re-stashed after surreptitious usage.

I often wonder where I would be at this point in time if I had been content with the rewards of fatherhood (so enjoyable and numerous). Instead, I indulged in the guilty but intense pleasures and very taboo feelings I received from wearing a bra and the feel of its straps underneath my shirt, the sensations of my freshly shaved legs rubbing against each other in new stockings, or joy of a dangling pump at the end of a foot as I rocked cross-legged at my desk. Or that feeling of being incomplete unless I painted my toes and shaved my legs, (even if no one else could see them under my suit.)

The nature/nurture argument will never be settled completely on most aspects of human behavior, and crossdressing complexity is no different. Who knows why I am a crossdresser. I might not have gotten “hooked” on crossdressing after putting on my first padded bra at 12, but a lifetime of crossdressing may have been inevitable. I fought a losing battle with crossdressing for the next 30 years. With the advent of the internet, it was no longer a solo battle, but a battle nonetheless; one I’m still losing. Eventually, the good feelings and content I have while being dressed increased, and more importantly evolved into a self-acceptance. Rikki and I have learned to become most comfortable in “his/her own skin”.

As bad as I have made this sound, let me express the Joy. I no longer purge and haven’t done so for many years. Rikki is still very much in the closet, but at least the lock is gone and the closet opens every day. I have come a long way. I regularly paint my toes, which my wife has grudgingly accepted, as well as the shaved legs and sock drawer containing knee highs, tights, and pantyhose but no socks. My closet has 10 pairs of heels and a couple of pairs of flats and feminine slippers. I’m no longer embarrassed to have her see me dressed (as long as I don’t push it….Rikki is still tolerated as a guest more than welcomed as a member of the family). Having Rikki feel at ease with another living breathing person in the room was a very big step, one that has brought me a lot of satisfaction.

My wife does have some appreciation of how good I feel when dressed–even if it’s only partial. I don’t go full-wig and makeup with her yet, but that’s coming, if I live long enough.

In spite of all my complaining, self-doubt, and occasional discontent with my lot in life, I do love being a crossdresser. I love being able to talk about it.

Maybe someone on this site will read this and relate. Crossdressing for me has been a joy and a curse. The curse came first and then the joy. Despite it all, it’s possible that you too can arrive at a place where your inner-woman is at peace with your outer-man.


  1. Sophia Silks 3 months ago

    thank you Rikki – I really enjoyed the read 🙂

  2. Colleen Mack 3 months ago

    Rikki, thank you for sharing your story. I’m a 60+ cross dresser for over 50 years Every word you wrote I could definitely relate to

    Every feeling from the guilt, shame and the absolutely sheer enjoyment of dressing I have gone thru. I felt like I was a freak and this issue of loving to dress would go away but it never has

    Again thanks for sharing your story because it helps me not feel like I the only one in the world that feels this way


    • Author
      Rikki Edwards 3 months ago

      I was away on a brief holiday when my article got posted so I did not see this until today. Thanks so much for the support!

    • Rachael Joyous 3 months ago

      Yes, same here, Colleen. The article sounds as if I wrote it word for word. It was spot-on with everything. I am the same age and I am feeling the exact same thing. Thank you for the great article! Rikki and Thank you Colleen for your post!


  3. Falecia McGuire 3 months ago

    Hi Rikki,
    I get the curse thing, but who ever knows about the journeys of our lives. My first wife knew about my crossdressing, but never zeroed in on it – so my kids never knew. She was more concerned about HER agenda. I think I drank too much and isolated myself from her because I felt she didn’t support me or understand me. Ironically, in my case, if she’d grasped the significant of my crossdressing, we might have had a chance. To this day, after nearly 27 years, I still don’t know what she really expected of me.
    I’ve now been married 24 years – longer than the first twenty – prior service. JoAnn doesn’t really share the CD thing, but she understands how significant it is for my life. She probably wishes it would go away, but wouldn’t trade who I am for the greater simplicity it might bring. She encourages me to thin out my wardrobe, chides me if something I wear looks too feminine, but gives me the space I need. What she doesn’t get is that I’d most enjoy her sharing some of the enjoyment. While I DO dress alone, I’d prefer her acceptance of, at least, the androgyny. The full femme look I could forgo for the most part.
    All this being said, if we are kind to others and apply reasonably moral standards to our behavior, our lives and relationships are, ostensibly, on a course to which we adapt but never control.
    Be well,

  4. Rikki,

    Where to start and not make this long. I am so glad you wrote this and I totally agree with the Joy and the Curse. I am fortunate I have not purged yet and I am glad I did not. I have had so much joy dressing and being Sara. I also have not lost a wife as of yet. My wife found out in 2015 and that again was a joy and a curse. In the beginning it was rough, fights and crying and so many questions. Then she started to take to me dressing with limitations, we enjoyed doing things and shopping but then something changed. Now it is a curse, for she does not like it but has allowed me to pursue it with some limitations. She says at times she regrets agreeing to allow me to dress even with the limitations. I feel more strangled and held back due to regret that I am hurting her. I so enjoy being Sara and going out with other CD/TG. It makes me feel so wonderful then I return home to the look. I am sure many of you with wives that tolerate you cross dressing, have seen the look, and I am back to regret and shame. I so remember the times I would sneak and dress and after wards I would feel a little regret from lying but I would feel so wonderful about myself. But now with the look I feel regret and shame. Oh what a roller coaster it is with the Joy and regret. It is a curse I wish upon no one but the joy to be yourself I wish for all and hope one day others can allow that for us all. Thank you so much for writing this and it helps me open up to myself and maybe more to my wife her in the future.
    Sara Marie

    • Author
      Rikki Edwards 3 months ago

      I am glad that you took the time to read my article, since it seems we have both been in the same places, perhaps at different times, but the same places nontheless.

  5. Gerella Enigma 3 months ago

    Courageous story Rikki. All of us reading it can relate in some way.

  6. PY Marshall 3 months ago

    Rikki, after reading such a painful story it makes me realise just how fortunate and privileged i have been throughout my crossdressing journey. I do hope that Rikki can continue to develope throughout the following years and she eventually reaches a better level of contentment which is acceptable to both .Kind wishes .Py x.

  7. Gemma Jessica 3 months ago

    Luckily for me I have never seen my crossdressing as a curse. Being Gemma makes me so happy. Frustration is on the other side of the coin for me. I’m not out to anyone I know so I have to go long periods without her and at times this is very difficult to bear. Thank you Rikki for a very thought provoking article.

  8. Liza Mellinger 3 months ago

    These thoughts describe me perfectly, Rikki! I might even share them with my wife

  9. Rose Turner 3 months ago

    I know why we do it. We enjoy it. Society has dubbed crossdressing as weird. And they don’t want to see it or deal with it. It is weird. But, hey, we enjoy it, Right?

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