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).

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.

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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.

En Femme Style

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.

EnFemme

 

More Articles by Rikki Edwards

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    Sophia Silks
    Member
    Sophia Silks
    4 years ago

    thank you Rikki – I really enjoyed the read 🙂

    Colleen Mack
    Lady
    Active Member
    4 years 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

    Col

    Rachael Joyous
    Duchess
    Active Member
    4 years ago
    Reply to  Colleen Mack

    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!

    Rachael

    Falecia McGuire
    Lady
    Active Member
    4 years 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… Read more »

    Sara Marie Franklin (SMF)
    Lady
    Active Member

    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… Read more »

    Gerella Enigma
    Member
    Gerella Enigma
    4 years ago

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

    PY Marshall
    Lady
    Member
    4 years 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.

    Gemma Jessica
    Lady
    4 years 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.

    Liza Mellinger
    Lady
    Member
    4 years ago

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

    Rose Turner
    Member
    Rose Turner
    4 years 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?

    Angela
    Lady
    Member
    4 years ago

    Rikki, I can certainly relate to what you wrote. Specifically the feelings of guilt and shame. And I will add anxiety. But the feeling I get when I wear a dress is complete happiness. I purged a several years ago and swore never to wear a dress again. But here I am again buying new bras, panties, nylons, a dress and those beautiful heels. I’ve come to realize being Angela makes me a better and happier person. I do still ask myself why I like to wear women’s clothes. Which may be why I have feelings of guilt and shame.… Read more »

    Angela
    Lady
    Member
    4 years ago
    Reply to  Rikki Edwards

    Hi Rikki, You are certainly an inspiration to me. My confusion I’m sure comes from my upbringing. A very male dominated culture. I’ve always struggled with you must want to be a woman because you want to dress like a woman. Which as I think about my past life is why I always kept Angela deep in the closet. I would get dressed and then after a few hours think OMG what am I doing and rush to take everything off before I was caught in woman’s clothes. Joining this site has been extremely helpful. Hearing from girls like you… Read more »

    Colleen Mack
    Lady
    Active Member
    4 years ago
    Reply to  Angela

    Angela

    OMG. Your reply is so right on. I’m in the 50+ year dressing category myself and just like you I finally 2 years ago came to the realization that Colleen is a part of me that I could no longer say “someday this will go away”

    You know how great it is to hear others like us say the things we have felt forever

    Your post was great and enforced my belief that I’m not a freak

    Thank you
    Colleen

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