Which One Today?

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For as long as I can remember – since puberty at the very least, possibly earlier – I have wanted to be able to wear what girls can: skirts… dresses… neat, pretty shoes with a bit of heel going on… that kind of thing. Not all the time: just whenever the desire arises. And it does.

This isn’t a kink thing – it’s got nothing to do with “the thrill of transgression” or any other path to arousal. Nor does it speak of a taste for drag. I just think the clothes look lovely, and there are times when I want to inhabit that loveliness: to ‘be’ it, even if only temporarily.

In recent years I have made some small inroads in this direction: I’ve been painting my nails as a daily habit since 2019 (my tastes lean towards the sparkly and iridescent) and I have two pairs of boots from a womenswear chainstore: not overtly girly to look at, but they’re smart and, unlike most men’s shoes, they make my size 10 feet look less policeman-like. When I’m out in town, both of these – nails and shoes – boost my confidence. I don’t see either as a “gender marker”: I just feel as if they’re helping me to present the best, most truthful version of me to the world.

Skirts and dresses, though? That’s a whole different level of gameplay. Owing to a combination of being born at the wrong point in history and being too much in thrall to my inner critic, I’ve never been fully able to realise this part of the deal (OK, let’s be honest, have never allowed myself to); and now – when, as an unattached 60-something widower with time on my hands and nobody to please but myself, I could in theory buy any garment I like and present in any way that pleases me – I doubt it will ever happen. Whatever window of opportunity might once have been mine to leap through, it has long rusted shut.

You see, the other, equally important, part of the equation is this: I don’t want merely to be able to wear that sweet, floaty summer dress I can’t help cooing-over in the department store window; in order for it to be right, to feel right, I would have to look utterly natural in it: to be …no, not a woman, but somehow convincingly the kind of human the designer had in mind.

As a decidedly un-macho teen with – though he says as he shouldn’t – halfway decent bone structure, 40-odd years ago I could just about have got away with it …strictly in private, of course. (Me, in a dress? In public? In the 1970s? In Birkenhead? Get real!)

Peter Miller via Flickr

Now, though, there’s no such hope. Hasn’t been, for decades. If tomorrow I were to buy some delightful thing by mail-order (assuming I’d managed to find it in a size that might go anywhere near my tall, bulky frame) and try it on, what I’d see in the bedroom mirror would annihilate my every last scrap of self-respect and make me want to kill myself, for the glass would show me a reality I already know and have no wish to lay eyes on, that sure-fire staple of knockabout comedy, the one guaranteed to have ’em rolling in the aisles: a big bloke in a frock. Think ‘Carry On’ films. Think Bernard Bresslaw. Yeah – that.

Before you posit the obvious: no, I am not transgender. I’m a cis male and comfortably so: never been in any doubt about which pronoun fits; never had the desire to be known as anything but “he”, and this would still pertain regardless of what combination of garments I might be wearing. Likewise, I’m a stranger to gender dysphoria. Being physically male does not distress me. It does distress me that, as a physical male of a certain age and build, I’ll never look “right” in the clothes I occasionally hanker after and wish I could fill convincingly, but having boy bits? Never been a problem …and, by the way, I am fully cognizant of just how massive a privilege this is.

So what does all this mean? What does it make me? Let’s see… a cis male with a lifelong, mostly unrequited yearning to wear girl stuff? “Cross-dresser” would seem to be the elephant in the changing room. No thanks. That term carries far too much baggage for my liking. Type it into any search engine and you’ll discover a highly sexualised narrative that, while claiming to subvert rigid gender norms, actually serves to uphold and reinforce them. If I see the words “sissy boy” one more time…

What else, then? Some delicate, liminal shade of non-binary? I have good, dear friends who, on hearing me voice that possibility, will have just had to stifle a little yelp of sibling joy. Hold fast, my enby pals: don’t start chilling that champagne just yet. The jury’s still out on that one, and Henry Fonda has a lot of convincing to do

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Maybe, just maybe, the truth of me is something far less profound …that I’m no more than a disgruntled dandy: an aesthete, railing against societal constructs which say that only girls get to do Pretty – and, as such, my sense of misfit dissatisfaction is no different from that experienced daily by countless women who, on catching sight of some sigh-inducingly delicate thing in a window display, immediately think “Yeah – like that’s ever going to work on me!”

Ultimately, it’s a question only I can answer. The trouble is, I don’t know the answer. What I do know is that oftentimes, for my own idle amusement, I’ve entertained a wishful fantasy: that each new morning I could wake up as a blank, amorphous proto-being, walk to my wardrobe (which would contain a selection of body types: male… female… perhaps even indeterminate?) and think “Hmmm… which one today?”

But as that is destined to forever be no more than a wishful fantasy, I’d settle for being a boy …one of such breathtakingly lissom elegance that ANY garment falls well on me and no-one thinks to ask about anything so tediously insignificant as “gender”.


Cover image courtesy of Mølterland via Flickr

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