The Masculine Prison

The Masculine Prison

Society expects strict behavioural patterns from both men and women, but gender isn’t strictly binary and on that sliding scale of biology and nurture exists a lesson for us all, says Stewart Who?

As a fearful gay child, the best policy to avoid an ‘outing’ was to act as butch as possible. Maintaining this 24 hour charade proved an exhausting, unrewarding and challenging role. A dull life was the prize for a convincing performance, while a poor show guaranteed a kicking.

A complete avoidance of anything feminine formed the basis of this Théâtre De Hetero. While rugby piss ups seemed to frequently end with team members donning drag, I’d merely purse my lips and spectate bitterly from the bar. It’s unlikely that Gary Watkins or Dave Roberts viewed their post-match wig wearing as an escape from masculinity, but it was.


 Gender magic

Over the years, I’ve met and partied with the world’s most famous drag stars, female impersonators and gender questioners. Lady Bunny, Chi Chi La Rue, Lily Savage, Ru Paul, Miss Kimberly and most recently, Jodie Harsh. Fascinating, entertaining and talented, they all use their flight from gender to provoke shock, awe and confrontational desire.

Back in the ‘80s, Steffan Whitfield was a ‘female impersonator’ who resembled Leo DiCaprio as a boy and Marilyn Monroe in drag. A hit at Madame Jo Jo’s, the tabloids loved him and he went on to promote the Way Out Club “for girls, boys and inbetweenies.”


The late, luscious Steffan Whitfield

Ghostly butterfly

Sadly, he died in 2005 and a few days before his memorial party, something spooky occurred. Unbidden, a photograph of Steffan in a gold lamé dress, fell from a bookshelf, fluttering into my face like a ghostly butterfly. Naturally, I screamed the house down, which goes to prove that a lifetime of acting butch won’t change your chromosomes.

“What’s wrong?” begged my flatmate.

“I just got a message from beyond the grave. From Steffan,” I explained.

“What’s the message?” he asked, deeply concerned.

“That we have to do drag at his memorial.”


 Drag O’ clock

After a lifetime of loving other gender illusionists, it was time to become one. My shrink was alarmingly supportive and acted as my stylist when we went dress shopping in Camden market. He even bought a frock for himself. The first thing you notice with regards to wearing a dress is how vulnerable you are.

Especially if you’re in a light blue, thigh skimming, lycra number. After years of protection provided by baggy jeans, a mini skirt feels like dumb nudity. Shockingly exposed to the elements, your body shape is public property and that feels both thrilling and utterly terrifying.


 Spike heels

Add spike heels to the mix and you truly wonder how and why the girls do it. On the night of Steffan’s memorial, we had our make-up done by the pro slap-artist Giles Edwin Bishop and our wigs were styled by Way Out coiffeurs.

The transformation was persistently alarming. It was impossible to escape the physical discomforts of a woman’s wardrobe, but easy to forget how it might look. Catching sight of myself in a mirror proved consistently shocking.


 Way Out

The Way Out Club is a portal into a world where little is what it seems. Not all of those who wanna dress like women, look like women and cross dressing, heterosexual married men are common. There’s beefy transvestites, cross dressing pensioners, pre ops, post-chops, teen dreamers and…an unlikely bunch of admirers.

With my hairy legs, brick-like jaw and furry forearms, it was an unexpected twist to find apparently ‘straight’ men giving me attention. With so many ‘convincing’ cross dressers, why would they hit on this big bloke, cloaked in thin veneer of femininity?

Sexuality, desire and other people’s erotic triggers are never as simple as we might assume. Alarmingly, when this conclusion looms into view, you begin to question your own impulses. It’s a confrontational, spiritually jangling  trip, which is probably why society at large prefers to suppress this discussion.


Leery eye

A fine looking man, who happened to be a bodyguard for Juliette Lewis and the Licks, took quite a shine to my unimpressive transformation. He bought drinks, made leery eye contact and doled out compliments. It was very strange. If we were two men in a gay bar, I’d understand the drill, but as he seemed very heterosexual, what on earth was happening?

The truth of the matter was that I was a gay, hairy man in a dress. The protocol for this unusual  mating ritual proved very evasive. Did he really fancy me as a woman? If we had sex, would I have to keep the wig on? Would that make me a transvestite? Or a fetishist. And if that was the case, what of it?


Bitchin’ and shaming

As these questions slid around my mind, a gaggle of pretty trans girls clacked into view. They eyed me with a mixture of disdain and pity, then fled with The Bodyguard to a nearby table.

They made great show of mocking my look,  like  Ru-Paul’s Drag Race meets Mean Girls. In response, I made great show of rummaging in my handbag and re-applying lipstick. The Bodyguard seemed to enjoy my persistent bravado and continued to wink and smile as the Mean Girls grew more competitive and less subtle in their bullying.

Okay, so I looked more like Vincent Price than Katie Price, but regardless of that fact, or the bitching from his bitches, The Bodyguard couldn’t look away. More than the make-up, heels or handbag, it was the energy of this scenario that created an illusion of an escape from my gender.


Ungainly and anxious

A group of younger, prettier contemporaries were loudly attacking my age, weight, dress and femininity, but like a fool, I clung to the idea that The Bodyguard would ditch ‘em and sweep me off my bar stool. He didn’t. For a few minutes, maybe, just maybe, I experienced a tiny window onto what it might be like to be an insecure, nervous, middle-aged single woman in a City bar on a Saturday night.

It was frightening, stressful, confusing and depressing. As anxiety swept over my ungainly, hirsuite collection of cells that is sometimes known to me as ‘my body’, there was  little choice but to check my make-up in a Maybelline mirror and order another yet another martini.


School of drag

Of course, I am not a woman, so will never know what it really feels like, but the episode was horribly instructive and educational. Drag is mostly seen as entertainment, a camp facade or a theatrical device. It is all those things, but it’s also a lesson; in the beauty standards society expects of women and the efforts required to live up to that.

Few men actually look good in drag, but every man should do it. Not only is it a temporary escape from the masculine prison, but an informative spell in the prison that women exist in all the time.

First Published: The Hospital Club Magazine 2008


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