In the film Pretty Woman , a shapely Julia Roberts is a Hollywood hooker swept off her feet by wealthy lawyer Richard Gere. He pays her a tasty $3,000 for one night (this is 1990, remember) - and he would have a paid four. They stay at one of the poshest hotels in LA and go shopping on Rodeo Drive . He rescues her from a life of sleaze and degradation. They live happily ever after. So the night after I "do a Julia", why am I covered in puke? Why are there only 46 pounds and a few pence scattered on the floor of a Holiday Inn in rain-swept Leeds ? And why is there no one lying next to me - even though those sweat-soaked bed sheets tell me that I definitely slept with something only a few hours ago? Like the fateful final voyage of the Challenger space shuttle in 1986, this had all started well enough, but ended very, very badly indeed.

THE BRIEF FROM HELL

It begins just before Christmas when FHM, who had clearly spotted a desperate look in my eyes the last time I was in the office, invite me back for a chat. Basically, they've heard that the Internet has made it a doddle to set yourself up as a male escort. They've coined a new word for it - "manwhore" - the headline's as good as written, and all they need now is some poor berk to do it. I leave promising to call back with an answer in 48 hours and clutching a woman's magazine with an advert for something called Ideal Escorts at the back. "We urgently require male escorts," screams the ad. "Earn £500 a night!" I mull it over on the tube. Well, I am single, and I do spend like a Saudi every time I go out on the pull. And, truth be told, I usually end up in bed with little more than a hangover and a silver of kebab meat stuck between my teeth. Imagine having women come to you . And paying for the privilege! I spend the next two days quizzing friends about male escorts. Does anyone know one? Is it prostitution? What type of harridan buys a man for the night? Where do you go for the date "date"? Next stop: the FHM lawyers. "Dear well-paid clever people - will I go to jail if I agree to this?" When their report returns it is memorable for several reasons, not least because it's as thick as the Bible, contains the phrase "a common prostitute" in relation to me, and refers - several times - to the Sexual Offences Act. However, once they decided that FHM won't be "corrupting public morals" (their words) by publishing such "filth" (my mother's words) they decree I can go ahead. Hurrah! I'm in. Next stop: fanny express!

LAYING THE BAIT

Only an idiot would do this without proper research, so I track down a seasoned escort and pump him for advice. I find a chap called Phil, who's French, muscular, plays rugby and has taken out a lot of ladies. We couldn't be more dissimilar (but hey, Phil! At least I have my own hair and teeth!), although his word is gospel. When we meet, he's deadly serious and hits me with a list of rules: •  Get the money upfront first •  Always take the lead •  Be polite and confident •  Don't swear •  Give her lots of attention •  Don't get drunk •  No matter what she looks like, look at her like she's beautiful To me, Phil's rulebook seems to take the shine off the whole thing, but the machinery is suddenly set in motion after yet another unsuccessful Friday night when I stagger home, fire up the computer and suddenly find myself, signing up. Incredibly, there's no interview procedure or face-to-face meeting; you just stick up your details and wait for the phone to ring. A rag-bag assortment of men litter the website, many of them looking like the council has just laid them off. On second thoughts, an absence of background checks may mean they're fresh out of Wandsworth clink. I decide to go for the "smart and friendly" look, knock up a quick digital snap wearing a suit, and upload a decent picture of myself. I'm hoping to attract the woman looking for a sophisticated chap - rather than a serial killer.

BITE

And then.nothing. All's quiet for a full month, but I keep up hope and finally I strike lucky. Pauline, a 33-year-old manager of an IT company, sends me an e-mail: "Are you able to accompany me to a black tie event in Leeds ? I've never done this before, so I'm very nervous." Suddenly, it's real and I feel like I'm 16 again, drunk and being straddled by a middle-aged woman who has a slightly musty smell about her. In other words I'm happy, confused and shitting it. The courtship is brief. After a couple of polite e-mails, I pluck up the courage to telephone. I really need to discover what she looks like, and coax her into sending me a photo by e-mail. I wait to double click on the attachment: this is it. I know I can do anything with anyone as long as she isn't Dawn French's bigger sister.or hairy.or.ah, fuck it, here goes. And.and.and.immense relief. She's normal! She's blonde! She looks like the slutty rich one from Footballers' Wives ! When the day eventually comes for me to travel to Leeds I'm feeling pretty well prepared. I've booked a train and a hotel, hired a tux and had a good night's kip. It feels a bit like getting ready to go to a wedding. The reality of being paid for sex has definitely not sunk it. After a couple of beers in my room, I go to meet Pauline in the hotel bar. She walks in.and looks great in a sexy black cocktail dress. Hell, I've been lucky. Very lucky indeed. We chat politely and my mouth goes into overdrive as I try to compensate for her obvious shyness. I'm talking utter shite and am not exactly at ease myself: the fear of asking her for £300 has been steadily creeping over me all morning. What do you say? "Hi, give me the money or I'm going home"? The thing is, I can't honestly say I'd turn down sex with this woman if she didn't pay. I can't charge her for what I'd do willingly for free, surely? To make things even more complicated, there's a growing unease about the sex - I don't even know if she wants or expects it. Maybe she really does only want me to sit with her at the dinner dance. Do all escorts have sex with clients every time? Shit - what did Phil say? My mind bounces from one thought to another. What if I ask her if she wanted a shag and she is offended? Worse still - what if she's a pervert and asks for her brother to join in? I'd faked a whole relationship once before, so this shouldn't really be a problem. "Okay then." I say, sounding like Alan Partridge. "Pay up, or I'm going back to my room!" Big smile. She laughs, reaches into an expensive-looking handbag.and pulls out a wad of notes. Dear God. This is really happening! Like some sort of drug dealer, I palm it low, under the table. Unfortunately, £300 in twenties is not as bulky as you might imagine, but still: the feeling of being paid by a woman - this woman - makes blood rush to my head. I immediately order champagne cocktails. Who'd have thought it - being paid is some kind of aphrodisiac. It's wrong. It's dirty. It like it.

THE DATE

We concoct a story that we're childhood friends recently reunited at a mate's wedding and she debriefs me about the party. It's a dinner dance for the important people from where she works; there'll be lots of boring old men there and she wants me to make it more bearable with an escort because she is new to the area - a considerable gamble on her part when I think back to some of the odd-looking chumps on the website. She tells me she picked me because I didn't look like a psychopath. And I blush when she adds "and you're cute." One the way to the dance I make sure I follow The Rules. I open doors, make conversation to relax her, try to be funny, listen attentively - it's like being on an exciting blind date, although she's definitely nervous and I feel a genuine pressure to entertain. After the initial buzz of meeting her work colleagues and the whole "faking it" thing, it begins to be a drag. I can see why she needed an ally there - the people her are so stiff it could have been a gathering of undertakers. Bored, I get some surprising kicks out of flirting with her - reminding her in whispers that she's paid for me, and that the fools here don't know. It's exciting. It makes us feel like naughty schoolkids having dinner with teachers - and it's always good doing something you shouldn't. By the time the band strikes up, I'm drunk, horny and reckless. The problem is, we're stuck listening to a shitty jazz combo who might have gigged on the Ark. To my dying day, I swear it's Pauline's idea to get a drink at the bar. The bar in another part of the building. Too late, I hear Phil's voice in my head: "Don't get pissed! Don't get pissed" he taunts. Forward one hour and several shots of vodka later, we're all over the place - and all over each other. But the more it looks like we're going to sleep together, the more uncomfortable I become about the cash she's paid. There's a tightness in my stomach. The phrase "common prostitute" springs to mind as well as the fact that most people would imagine me hanging out on street corners and giving out blow-jobs in the back of a white transit. So I'm spending like crazy. I figure that if I don't have it, then it doesn't exist - simple man-logic. It's drinks for the barmen! Tips for the waitress! More booze! The man used to buying champagne when Sainsbury's has it on special for a tenner spends £50 on a single bottle of the stuff. For my room.

SHOWTIME

This is it. We stagger to the life and press "2", Pauline breathing, "This is so naughty," whilst grabbing my bum so hard she almost loses a finger. The shy, respectable woman from the start of the evening has disappeared. We fall into my bed and have mind-blowing sex that I'll never forget. I wish. What happens is this: we roll drunkenly over each other, tug at awkward buttons and clash teeth while trying to kiss. It's a frenzy of groping and thrusting that any teenager would be proud of. There's no performance anxiety either. In fact, it's the opposite - I'm ramrod hard, going at it like a Viking, and there's not the slightest chance of swiftly blowing my load. Mid-thrusting, we sort of pass out, knackered. She really deserves a refund. We try again a few times, but the momentum's lost. Still - there's always the morning. Except there isn't, because Too Much Booze + Strenuous Exercise = Puke. Wrapped in the duvet, she walks in on me with my head resting on the porcelain. I'm green of face and sweating like an Aussie binman. I certainly can't talk to her; every time I open my mouth a shot of bile shoots out. I'm in too much pain to be embarrassed and just want her to leave so I can die in peace. And leave she does. It's only 8.10am, and she scurries off, clearly humiliated. My whoring days are over. I'd had a legendary night out, but there's no way I could do this all the time. As a one off, it was a mental experience, but I can't live with friends and family thinking I'm a prossie. It really is a head-fuck if you think about it. To do this escort thing you need to be confident, interesting, funny, have the morals of an alley cat - but be able to exercise supreme self-control. There's money to be made out there, too - particularly if you're good-looking and don't using your mush to earn cash. But me? I've learnt not to knock masturbation. At least you don't have to dress up for it, and it's sex with someone you love.