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.