The World’s Worst Prostitute


By Simon Doonan

Simon Doonan explains why hooking ain’t easy.

Illustration by Miles Donovan

Manchester, England, 1973. It’s my final year at college. Funds are running low. I bump into a fellow student at a church hall jumble sale. After a childish and embarrassing tug-of-war over a 1930s fox-fur scarf thingy with heads and paws dangling off it -- Halloween was coming up and I thought I might slice the dead fox into a bikini and go as Raquel Welch from One Million Years B.C. -- we call a truce and pop next door to a filthy tea shop to commiserate about our financial woes over a cup of greige tea and a slice of gypsy tart.

Gypsy tart, I should explain, was a truly appalling, now-defunct British dessert which was so revolting -- the main ingredient was boiled, congealed tinned milk resembling pus -- that even writing about it makes me feel vomitacious. It is hard to imagine how we ate it, but eat it we did. In his stunning autobiography, the fabulous Keith Richards bravely confronts the horrors of gypsy tart and attempts to describe the taste: “Pie with some muck burned into it…”

Back to 1973. During the consumption of this hideous concoction, my pal excitedly tells me that she has found a new source of income. She has started to make extra cash by flogging her jumble sale thrift finds to fancy London vintage emporiums such as Antiquarius on Kings Road and the uber-groovy Virginia Bates on Portland Road. (Still in business and now selling bias-cut ’30s numbers and nifty Victorian capes to the likes of Kate Moss and Lily Allen.) Her new incarnation as a vintage picker explains the aggressive posture over the fox fur.

My pal also mentions, quite en passant, without batting so much as an eyelash, that she has figured out an additional way to take the financial pressure off: She now gives her landlord a monthly blowjob in lieu of rent. I was so stunned by this revelation that I choked on my gypsy tart.

At first, my pal thought that I was shocked or embarrassed, and she got all huffy and remonstrated with me for being judgmental. Once I stopped coughing, I was able to reassure her that, far from feeling judgmental, I was, in fact, filled with admiration for her entrepreneurial zeal. I would have said, “You go, girl!” except for the fact that this convenient phrase did not exist back then. So I probably said something old-fashioned and clunky, like “Goodness me! You certainly are a very enterprising young woman. Good luck with this exciting new direction which your life has taken!”

I was impressed. Very impressed. Very, very, almost irrationally impressed. My louche pal had unleashed something rather wicked within me.

The following evening, as if impelled by a supernatural force, I got all scrubbed and twinkied up and made my way in my platform shoes, vintage oxford bag trousers, and my copy of a Mr. Freedom satin jockey jacket to a working-class gay pub near the canal in the center of Manchester. This is where I often started my Saturday nights. A drink or two and then off to a chichi disco called Samantha’s. On this occasion I stayed at the pub with a pal called Vinnie, and got thoroughly smashed. I had a plan.

Vinnie was a trainee hairdresser. He was very open about the fact that, as a younger twink, he had been “on the game.” But Vinnie was now respectable and had put his tawdry past behind him, unless the rent was overdue, in which case he was anybody’s.

Drunken escapades, if you can remember them at all, are recollected in the jerky handheld-camera style of the early Andy Warhol movies. There are no gentle fades, just lots of abrupt cuts.