Having reached what I call my “trombone” year, my seventy-sixth on the planet, and having been crossdressing since my eighth year – perhaps earlier – it is surprising to discover that there can still be things to be learned about this fascination that has with varying intensities driven most of my life. Discoveries of younger years have not, it seems, completed my education, and even at this late date, it seems there is more to understand.
My first significant lesson about crossdressing was that my parents looked askance, to put a gentle face on it, at my exploration of my sister’s clothing. At a young age, then, I became aware that my desires must be hidden from family and friends, as they have been from that time on.
The second and perhaps most startling revelation, experienced during a vacation from college, was that being dressed as a girl could result in sexual arousal, a discovery arising from a completely unexpected – and entirely wonderful – surprise that occurred when wearing a dress obtained not from my sister, but nervously purchased for myself, I sat in my car parked in a secluded woods some miles from my parents rural home.
Since that day, armed with the knowledge of both the intense pleasure of expressing as female and the importance of keeping that expression secret from all who know my male self, I have grown increasingly adept – through a career in the army and subsequent retired life – at identifying places, generally in large metropolitan areas, and in the times to recreate in feminine mode. I have also been successful at keeping hidden an ever-growing wardrobe.
Several years spent in the Chicago area during my forties have been the most active and enjoyable period of female experience. A now-defunct north suburban bar, “Charlie’s Angels,” provided a safe and comfortable haven for crossdressers, one I was able to visit with gratifying frequency. There I learned the pleasures of hours spent dancing, playing pool, interacting with men who treated me as a woman.
Subsequent relocations and living configurations, however, have sadly curtailed opportunities for such enjoyment. Greater need for caution and lesser frequency of being out have characterized my last few decades.
In the autumn of 2015, though, using a visit to an old army duty station as a cover story, I achieved a long-held goal of spending several days in Provincetown, Ma. during Fantasia Fair. I could live twenty-four hours each day as female and have an entire town to explore with little need for caution or self-consciousness. And yet, there was something unsatisfying, something missing, and it proved a rather disappointing three days. Ever since I have wondered what had failed. I have pondered and analyzed, but discovered no explanation; until that is, this past summer, so many years later.
As suggested in the first paragraph, it is a surprise that with so much experience there would still be more that can be learned. The great lesson came when one day last summer I was able to carve out an afternoon in a nearby city, a chance to be taken to lunch by a gentleman met through a website. We met in a park, took a bit of a walk, and had a meal in a welcoming restaurant. I took his arm as we strolled, and watched our leading shadows on the sidewalk, shadows of a man and his date, and I was that date.
So came the revelation. Throughout all the years and innumerable times spent dressed as a female, I had been just that: a man dressed as a female. In spite of the freedom of complete days and nights appearing female in Provincetown, I had not been anything but a man in a dress, and this was inadequate.
At seventy-six, then, I have learned the ultimate lesson. What I should have known – and what I have wasted years not knowing – is that it is not enough to just appear female; I need to cross the bar to feeling female, to experience the wonderful fulness of understanding and enjoying what it means to be a woman. I look forward to the next opportunity to make this happen.
It wasn’t until entering my later 50’s and after my first and so far only heart attack that I began searching for greater meaning and true happiness in my life. While I had begun cross dressing at 4 and as most of us hidden my light from the world living the normal life but on the surface only. I always knew what I wanted. How I wished so fervently I could just awake the next morning a new woman. Fully formed and ready to go. I prayed nightly for it. I wished upon stars, lady bugs and the occasional fallen… Read more »
Dear Phoebe;
Ah, yes, to use the approximation of a G. B. Shaw quote: “youth is wasted on the young." This can be a difficult road.
Lynn you look very feminine in that attire, you certainly don’t look your age
Liz
Dear Elizabeth;
Thank you for the kind compliment. I don’t feel it, either. Except for getting up from a chair.
Lynn
Lynn, you look so lovely in that outfit. I too found great pleasure in spending some time with a man. Something special about being out with a guy and doing some indoor sports. Hugs and kisses
Dear Yvette;
Thanks. There seems to be some suggestion that we are in the minority within the CD community. Perhaps not.
Lynn
Lynn, you look so poised and beautiful. It is no wonder why you have no problem venturing out into the world! Hugs, Paulette
Dear Paulette;
“no problem" may be a bit overly hopeful.
Hi Lynn, I am sure you have had your share of ‘problems’. However, your article demonstrates very clearly you have discovered and defined the ‘secret’ of being a woman; that being it is not just a matter of dressing like a woman, but rather allowing that dominant feminine nature (most men try to restrain) to come forth and blossom. Wonderful advice!
Dear Paulette;
The internecine warfare and anger that is so prevalent within the “T" community has always been disappointing. There are as many forms of “T" activity as there are individuals. In the words of the happily not late but happily great Red Green, “We’re all in this together."
Dear Lynn,
You are so right. I just dropped my membership from a “T" community because I never witnessed so much anger, frustration, confusion and most importantly, SADNESS as I did from that site. I am quite happy being Paulette! I guess that is why I am so happy to be here at CDH. Sure, we all have our issues with SOs, family being in public, etc., but by and large we are a long way from ‘needy’. I guess being an old girl like me has its advantages. Hugs, Paulette
Though it makes me seem guilty of “oldfartism," I believe this is just more evidence of the disintegration of comity and politeness.
If it’s oldfartism Lynn then we are both guilty of it because I agree with you completely!
A beautifully written article – you have a great writing style that flows really well. And a joy to read. After reading your article I was thinking of the well-known joke that you are only as old as the woman you feel – a joke which I suspect was never intended for cross-dressers but suits us perfectly. Living is a state of mind, as too is aging and I would like to add that you still cut a fine figure. You have really nice legs and I love your dress sense. Thanks so much for sharing your thoughts.
Dear Julia;
I have a favorite joke from the old cartoon “Super Chicken." Super Chicken, upon suggestion that he use his super-vision replies, “If I had any supervision, I wouldn’t be dressed like this." If I had any dress sense, I wouldn’t be dressed like that. Thank you.
Lynn
Very nice picture!
Thank you.
Again, very nice and attractive picture! Also, you mentioned that you had lived in the Chicago area. I am residing there myself currently.
Dear Margaret;
I was born and raised in suburban Chicago, but a career in the army has taken far afield, and I no longer live there. Thank you for the compliment.
Lynn
Thank you for sharing your story with us
Dear Michelle;
It is actually my pleasure to have done so.
Lynn
As an older (72), ever-maturing trans woman myself, I well appreciate your discovery and enlightenment. May I also say you present an absolutely lovely, truly youthful, and womanly image. Congratulations and may your discoveries and realizations of womanhood continue for many years, as well the expansion of your dating life with men who appreciate a fulfilled trans lady. Hugs.
P. S. – Great outfit from blouse to shoes! Holding it together woman!
What a treat. Thank you.
You’re welcome and I hope to see more of you in chat or email in the future, A woman of your experience is a valuable resource for so many less experienced, unsure, reluctant young transwomen and transgirls. So happy that you have also come to realize and have started to satisfy your true needs and desires. Hope to talk with you again soon dear sister.
You look cute in that flower print dress For myself I am a bit camera shy!
Well, thank you. Admittedly the unacceptable photos outnumber the acceptable.