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.
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.
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Thank you for a wonderful post Rikki! So much you wrote highlighted the dilemmas and joys I too feel about being a crossdresser. When you crossdress, do you feel your actual age? Or something different? I like tend to like trends of women 10 years younger then me. As you grow wiser, do you ever think about being full on out? I wonder if a day will come when I decide that life is too short and those that I aim to please will never truly be pleased. I might as well make me happy. Until then, my clothing and… Read more »
Thanks for the wonderful compliment. When I dress I pretty much feel my actual age, although I suppose an objective observer would probably say I am dressing a bit younger. But how can a woman be too old for sexy heels or short skirts?
At the present time, I don’t see myself going full on out, but I do dream of part time for sure. And like you, my clothing and shoe collection will certainly slowly grow.
Wow. You expressed what so many of us feel. Thank you. It is a blessing and a curse. But being fully dressed brings such joy. Hugs Jennifer
Rikki, I have SOME regrets over the effect on my marriage that ended fifteen years ago. Like you, I hadn’t told my wife about my need to dress -not because I was lying but because I truly felt (yes- foolish thought in retrospect I know) the need would disappear now that I had a woman in my life. She discovered my wig a year into the marriage and almost left then but stayed for 13 more years after I pleaded with her to stay and promised to stop. But I could no more stop dressing than I could stop breathing,… Read more »
Thanks Cyn for the feed back. I have followed with interest your posts since I joined the site, insightful and helpful always.
Hi Rikki thanks very much for sharing your story with us, i can relate to your story as mine is a lot like yours except I’m still in the closet to my wife and family they have no idea I’m a cross-dresser, I’ve experienced the joy and the shame of being a cross-dresser, i started just like you when i was about 8 or 9 years old, I’ve purged and started again many times over the years but about 10 years ago the urge got hold of me again and just got stronger so now whenever i get the chance… Read more »
Hi, I will confess that if I was ever to be single again, the thought occurs to me every now and then, that now that I have my children raised, that I would never remarry or share a house with anyone, so that Rikki could “run rampant"! I do enjoy letting my pantyhose and bras air dry in the open, and not have to hide my sexy mule slippers away while I am sleeping! But then I also enjoy having a beer with the guys doing the occasional testosterone things, so there it is….the dilemma once again!
I felt my own past coming out as I read your article. Crossdressing is certainly a blessing and a curse at the same time…
I knew there had to be many cd’s who felt about it like I do!
What a wonder post, this ha s been a total joy to read, The curse and joy of crossdressing seems to hit most of use, Maybe one day society will be more open to us as they are open to women crossdresing.
Don’t I wish! I think the basic male insecurity about sexuality will always keep us cd’s from being totally accepted….then again, how many years did it take for society to accept women wearing pants?
as we know life and people are complicated. some folks can be more open, tolerant, accepting, understanding than others. We all know breakups and divorces are hard. I don’t regret mine because my ex wasn’t the best person for me to be with for a number of reasons. Nothing ugly or bad, just not a good match of interests, intellect, etc. We are both better off apart and civil to each other. With my prev LTR that lasted 5 years, on the 2nd date I was up front about being bi because she sensed it and asked me. we had… Read more »
Yes when starting over with someone new, I couldn’t agree more, the best policy is openness! My only regret is that while I was open in the sense that I confessed my crossdressing very early, I didn’t open the closet door near enough.
Thank you so much Ricki that could be me having written those words very similar but my wife is unaware I believe!
Rikki, You certainly hit upon a number of similarities I think we have all gone through and thought about over the years of our Cross dressing. While I have not purged, I have experienced many of the same feelings…good and bad associated with dressing. My first marriage (did not end due to CD) had my CD thrown in my face a lot and the threat to out me…which she did during the divorce. My second wife knew right up front…full disclosure..so she could decide if she was ok with it. It does not do anything for her but is supportive… Read more »
Hi Rikki I really enjoyed your article and felt many of the parallels with your own life. I lost my first marriage not because of cross dressing but for other reasons. But like you it is a deep part of my life, I want to be free with it and mentally I do not want to face the social norms that have been placed on men. I am envious of women because they have broken through that barrier and most of society has accepted them for who they are. Even though I love dressing and wearing makeup has not made… Read more »