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.

EnFemme Style

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.

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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 Style


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    Rikki Edwards

    64 years old now and have been a closet crossdresser all of my life since I was about 12. I am married (second time) and my wife knows I crossdress. She is more tolerant than supportive but is getting more and more accepting. She still prefers Rikki stay out of sight but she knows I need my dressing time. I am a self employed professional with adult children who do not know about Rikki (so far as I know). As I get older I am finding my need to crossdress has gotten stronger and stronger. I underdress every day and keep my legs and chest smooth and toes painted, so that alleviates some of my need. I do not feel the need to transition however and I am very comfortable enjoying my dressing when I can get it.

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    4 years ago

    Great post Rikki! The joy and curse describes my experience so well. Until the last year it has been 99.9% curse and .1 % joy. This was because I had not accepted this aspect of myself. Since fully accepting myself about 6 weeks ago I have been almost studying my self, truing to understand what makes deLora tick and how to remain genuine to the part of me. Right now it is about 50-50 joy and curse and the more I understand it the better it gets. Your post also illustrates the huge strength and courage it takes to accept… Read more »

    Stephie Terrill
    Active Member
    9 months ago

    Oh Rikki! As I read your post, I KNOW you are a kindred soul, and you can see deep inside me! You know my girlish heart so well. Our paths have so many similarities, and our feelings about the joys and curses are so aligned. I LOVE a being a girl, and I am so deeply sad that my longings go unfulfilled. Sharing with sisters is one of the great joys! We are NOT alone! We are NOT ‘freaks of nature’. We are loving, and kind, and gentle, and tender, and sexy, and so enthralled with femininity. We hurt no… Read more »

    Stephie Terrill
    Active Member
    4 months ago

    Oh, Rikki! I was nearly in tears reading your (our?) story! I wish we we neighbors, and I would rush over to hug you, hold you close, and reassure you of how special you are. We girls have had challenges all of our lives. Most of us are only coming to full terms with the femininity that has been part of us, all of our lives. Finally, we are learning to love that girl who has always been with us, but always suppressed and hidden. We girls need the love and support of our sisters here to be able to… Read more »

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