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 win for a convincing performance. A poor performance invited 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

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

He died in 2005 and a few days before his memorial party, something spooky occurred. 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.

“What’s wrong?” begged my flatmate.

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

“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 enthusiastically supportive and acted as my stylist when we went drag 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 nudity. Exposed to the elements, your body shape is public property and it feels thrilling and terrifying.


 Spike heels

Add heels to the mix and you wonder 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. 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 one’s self in a mirror proved consistently shocking.


 Way Out

The Way Out Club is a portal into a world where little is what it seems. Heterosexual married men are common. There’s nervy transvestites, cross dressing pensioners, trans women and lots of furtive blokes who might be admirers.

With my hairy legs, lantern jaw and furry forearms, it was an unexpected twist to find seemingly ‘straight’ men giving me attention. Why would they hit on this big bloke in his thin veneer of femininity?

Sexuality, desire and other people’s erotic triggers are complex. 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 takes such issue with the topic.


Leery eye

A fine looking man, who happened to be a bodyguard for Juliette and the Licks, took quite a shine to me. He bought drinks, made leery eye contact and laid on the 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  scenario proved mysterious. 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? 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 came into view. They eyed me with a mix of disdain and pity, before fleeing with The Bodyguard to a nearby table.

They made great show of mocking my look. In response, I made great show of rummaging in my handbag and re-applying my lipstick. The Bodyguard seemed to enjoy my shaky bravado and continued to wink and smile as the Mean Girls narrowed eyes and bitched.

The Bodyguard couldn’t look away. More than the slap, 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 mocking my age, weight, dress and femininity, but like a fool, I clung to the idea that The Bodyguard might 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 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’ll never know what it really feels like to be a woman, but the episode was horribly instructive and educational. Drag is largely seen as entertainment, spectacle or a theatrical device. It is all those things, but it’s also a lesson, in the standards society expects of women and the efforts required to live up to that.

Every man should do drag. Not only is it an escape from the masculine prison, but an spell in the prison that most women exist in all the time.



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