Dressing as a woman for the first time at the age of 69
From The Guardian 11/24/17
I don’t know why my feminine side lay undiscovered for so long, but finding the ‘other’ me has been a revelation
A couple of years ago, I was invited to take part in a murder mystery party with a script written by a friend, and we were asked to invent our own characters. I informed him straightaway that I would be a cross-dressing artist, and would attend in my female persona. Well, as an artist, I was already halfway there… The writer was sworn to secrecy.
I can’t say for certain what prompted me to choose that role. I had an establishment upbringing; my father was a military man and Tory county councillor, my mother a product of the Raj. After a public school education, I went into teaching, marrying and having children in my 20s. Although I soon enough forswore conservatism, becoming something of a contrarian and loving a flowery shirt, I had never consciously questioned my gender. Before that evening. At nearly three score years and ten.
Preparing for the event, I was a touch nervous trying on dresses in the local vintage clothes shop, but the staff were used to fancy dress. That evening, my daughter-in-law did my make-up, zipped me up and sent me on my way looking passably glamorous, or as glamorous as a first-time cross-dressing 69-year-old could realistically expect to be. .
I delayed my entrance to ensure I was the last to arrive, hoping to make a splash. What surprised me was how comfortable I felt dressed as a woman.
The party was a success and the murderer was duly apprehended. Compliments on my appearance were generous – it was probably the wine talking, and I have good legs. But what surprised me was how comfortable I felt dressed as a woman. Soon I sensed a female within who was agitating to get out.
I began to wear nail varnish most of the time, and my initial nerves quickly dissipated. The only people who commented – invariably women – were always complimentary. I became more aware of my hands and loved the shape of my nails as they grew longer. My piano teacher would rather not hear the clicks that sometimes accompany a Mozart sonata, and I get a few strange looks in the bus, mostly from older men, but otherwise little negativity.
Quite quickly, I realized that although the nails allowed a modicum of exposure, Jill-in-the-box was now straining to pop out in person, so to speak. I began to buy women’s clothes. A friend helped me with make-up and took me for a full-on make-up session. When I asked the beautician if she was seeing more male clients now, she said it was still pretty rare, but I felt comfortable. My first sortie en femme was at a dinner party six months later. Among the same friends, I felt at ease. No need to give Her a name – mine was already suitable. Robin Pickering
It soon became normal for me to dress in women’s clothes whenever I spent an evening with the friends-who-know. I can’t imagine what it is like for them, though we talk do about it. I no longer feel self-conscious, even if there is something slightly incongruous about it – me tending towards the girlie with wig, make-up, frilly dress and heels while everyone else is in everyday clothes – but my friends do a good job of treating it as perfectly normal.
Returning home after a night out, I feel a certain apprehension stepping into cabs, but the drivers, bless them, never bat an eyelid. My only ventures out in public so far have been in the comfortably anonymous surroundings of London theatres (though I may have used the wrong toilet – the gents). I was flattered when a waiter called me madam.
I buy most of my female clothes online, which can be a bit hit-and-miss. At the start, it was easy to get carried away, but I’m now more discerning. There is, after all, a limit to the size of a girl’s wardrobe. I get most pleasure out of going shopping, and although I’m still nervous about smaller boutiques, on the few occasions I have wanted to try on dresses, the assistants have been helpful.
I can’t explain why I like wearing women’s clothes and all the rest, other than that I feel it is me. As time passes, it is becoming more of a need than a choice, though my age and location in a provincial city and prevalent social attitudes all discourage me from routinely cross-dressing in public. It is generally acceptable for women to dress in masculine clothes, but at best, cross-dressing men are still viewed as attention-seeking, eccentric or mildly amusing, while all we are doing is being ourselves.
Sometimes I wonder whether I could have discovered the “other” Robin rather sooner. Friends are curious about when She was conceived and why She surfaced when She did. In truth, I am too. Finding myself single a few years ago allowed me the time and space, and the Eddie Izzards and Grayson Perrys of this world probably played a part, along with fortune’s fickle wheel.
I don’t feel as though I should always have been a woman. But I do know that the feminine part of me is much more than a role in a murder mystery.
• Robin Pickering has been a full-time artist for 20 years, after a career in further education
Robin's story rings true for so many of us. Finding the courage to "Escape" and facing being transgender may seem daunting. However, the rewards and unexpected acceptance make it all so worth it.