It is a truth universally unacknowledged that a woman in possession of a certain figure going to New York for the first time is in need of a good bra."

Well, that sort of was my excuse after I set off the security system at Heathrow, despite having removed my jewellery, belt, shoes and a light mac. I had been thoroughly body-searched in front of an impatient queue. After some confusion, the security guard informed me and the gathering crowd that my underwiring was setting off the metal detectors. Who would have thought that by wearing Rigby & Peller you would end up one step away from being on the internationally wanted list.

This was the beginning of a trip to New York that I had been anticipating for a while. About 20 years, in fact. Now, finally, I was good to go.

"New York, New York - so good they bombed it twice," as I once heard an off-duty transvestite singing in the sweltering summer of 2006. Although I had never been to the city, over the years I had probably spent more time with its people than I had with close members of my family - it was the New York found in books, on film and, let's be honest, mostly in TV cop shows on all those Friday nights spent at home. My love affair with the Big Apple started young. First, the cartoon Top Cat. The buildings and menacing gloom of the Batman films. King Kong. The smart dialogue in When Harry Met Sally. The Jewish humour of Woody Allen before he turned pervert. The Staten Island heroine Tess, played by Melanie Griffith in the 1980s classic Working Girl. And let's hear it for Cagney & Lacey, NYPD Blue ... I could go on.

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So I knew the deal. People lived in tiny apartments and ate out. Rudeness was just survival of the fittest. Order your eggs sunny side up and always tip 20 per cent. "Start spreading the news." I was ready to walk those mean streets. But thankfully not on my own, for I was accompanying my best friend, who had to go for work. Thanks to her, we got bumped up to business class. (Make that my bestest friend. EVER.) Travelling business class brings the academic-salaried traveller many surprises. The first was 15 minutes in a massage chair at the exclusive lounge spa. After the chair "reads" your spine, you are kneaded vigorously from head to toe. If there is such a thing as chair-porn, I had found it. Another shock: you find your airplane food actually tastes like food. Oh, and I got to sleep with the best-looking man in the northern hemisphere.

Not quite true. I slept more or less alongside the best-looking man in the northern hemisphere, thanks to the seats that transform into a passable bed at the poke of a button. Impossibly handsome, he slept facing us with a knowing smile. I became so relaxed, wrapped in two cashmere-blend blankets, that I wondered if the captain wouldn't mind turning off the engine for a bit so I could truly float off.

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It was after disembarking and watching Mr Perfect disappear for ever through immigration that we lost the ability to recognise our own luggage. Only after a couple of pieces were left on the carousel circling around in the now-deserted hall did we stop panicking and pull off the giant cases that had been in front of us for the past 20 minutes. Then everything happened fast. Suddenly, we were outside in broad daylight and in the back of a yellow taxi, speeding along the freeway and towards the Manhattan skyline, heading to our hotel overlooking Central Park and two blocks away from Fifth Avenue. Yee ha!

I had planned my itinerary carefully. Visiting the Museum of Modern Art was, of course, a must for any cultured person. But sod all that worthy highbrow stuff - I was going up the Empire State Building and then off shopping. And the highlight of the trip? Together my friend and I would do the Sex and the City tour on our last morning.

For me, like many of my friends, New York had long become entwined with the series that revolved around Carrie, Samantha, Miranda and the one with brown hair whose name I always forget. The series affectionately expressed the contradictions of postfeminism: women enjoying unprecedented economic power and freedoms but at the same time often constrained by insecurity, obsessed by clothes and self-defined by their relationships with men. We shared their neuroses. We bought their shoes. We died for Big.

I came to depend on my weekly fix of SATC when I took up my first lecture post in a northern university. I realised too late that I had left people behind I could not live without. I had never thought my previous existence particularly glamorous: sure, I'd been labelled a gay icon for a short while, but only because I once wore leather trousers to give a lecture. Yet compared with living in the small town I now found myself in, where "exotic" was a man with a beard standing on a bridge every Friday afternoon, blowing into what looked like a goat's bottom, suddenly my past life looked very Carrie Bradshaw. With three gay men now my only confidants and work descending into a pit of misery, SATC was essential escapism.

But that was a long time ago, and the New York of 2009 offered a new history. Was the Obama effect discernible? Could signs of the global recession be seen even here? Had the scars of 9/11 healed yet? The next morning, I took two ibuprofen, put on my Clarks orthopaedic flatties, and headed straight out. For breakfast.

Three hours later, I began to find those answers. In the Fifth Avenue outlet of cult clothing chain Abercrombie & Fitch, as a matter of fact. Here, it was the African American girls with retro Studio 54 afros who were the queens of the shop floor. Too cool to actually serve, they danced by the staircases to the sound of The Best Things in Life Are Free. There was definitely an air of confidence among African Americans. Their dignity and generosity shone through. I saw mixed-race couples unselfconsciously holding hands.

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Unchanging was New York as the home of the hard sell. The age-old imperial maxim digitally remastered for a global age ran through the streets: commerce, Christianity and a caffe latte. No service, no space was too small to find a way to make a buck out of it. Sales were everywhere. Times were hard and people weren't buying, as Tina in cosmetics told me, in between her magnificent sales pitch: "Listen, I can give you the best-kept beauty secret in the business for the face, trust me - I am 64. 64? Do I look 64? Plus body scrub, moisturiser and salt rub. You'll look like a ripe grape. And this beach bag. Only $49.99." How could I say no?

We also saw the brutal reality behind the commercial drive. People work to stay alive. Literally. Unlike central London, you see lots of old people working. My waiter at breakfast should have been in bed. Whatever treatment he was paying for, he now had to wear a wig and his feet had swollen to twice their normal size. Nevertheless, he could still manage a sprint if one of his customers left without paying - as I found out in a haze of jet lag. And what a grip!

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There were many other signs of the shocking extremes the American model spawns, side by side. One of the many homeless people sprawled on the sidewalk - his lips smeared with red lipstick and women's stilettos on his feet - lay just around the corner from New York's top department store, so exclusive it makes Harvey Nichols look cheap. As I made my way up to the eighth floor and the hairdressing salon, having taken advice from my friend to have the complete New York grooming experience, I felt like Susan Boyle doing Manhattan. Just as I stepped out of the lift, the English owner, looking like a retired major who had served in the Rajputana Rifles, came rushing towards me chasing his bejewelled pet pug. There were more New York princesses and queens, male and female, concentrated in that salon overlooking Central Park than was decent. It was like a cross between The Devil Wears Prada and Are You Being Served? Fabulous.

Yet some things were disappointing. The Empire State Building was beige. Macy's was like a branch of C&A. I never got a decent cup of tea. And inevitably, perhaps because of unrealistic expectations engendered by watching too much CSI: New York, I didn't see much cop action at all. No drug busts. No dark rooms lit by torches. But then that's possibly a lot to ask from Bloomingdale's spring and summer collection.

And some things were just still too darn sad. Two flashing lights burn brightly where once the magnificent Twin Towers, well, simply towered. It's like the city still has a nasty gap in its front teeth from a vicious oversized punch. People get on with their lives for sure. But if you look up and spot a plane, for a moment you remember that footage ... A generation remains traumatised. After just three days in New York, the accumulated impact of all the life-enhancing ordinary people you meet is an even more emotional reminder of the terrible civilian suffering caused by the attacks. What a shock for a city that had never been under siege. We had the Germans trying to run our world every couple of decades, and then carried on spite of the IRA. But New Yorkers, for all their toughness and chutzpah, had nothing to prepare them for that dark day.

Finally, what of the climax to our trip? As the Sex and the City three-hour bus tour wound its way through the island of Manhattan from Central Park through the Meatpacking District into The Village, key hot spots were pointed out by Stacey, our guide, all interspersed with clips on screens above our seats. It was hell on earth.

Was it the effect of being an insomniac in the city that never sleeps, leading me to average about two hours a night? Was it the noise from the audience the night before at the fantastic new musical Nine to Five, particularly the whooping 'n' a-hollering every time the Dolly Parton character came on stage? Or just jet lag? Whatever the cause, so bad was my migraine that morning, I practically had to be helped on to the bus. Not exactly Sex and the City. When the tablets kicked in, I felt like a recovering stroke victim. I just watched miserably as the rest of the women laughed and drank their Manhattan cocktails at midday in Steve and Aidan's bar, before wandering off alone into a nearby gun shop ...

Of course, I rallied when it came to the chance of a cupcake from the Magnolia Bakery. But when we were released into the Pleasure Chest, the sex shop made famous in one SATC episode, I found myself moving quickly around the merchandise and back out the door. A lot of the battery-run equipment looked like something you might use to make a souffle. The Introduction to Bondage Kit could cost you an arm and a leg, I thought. And those beads didn't look like any necklace I'd ever seen ... Returning to the safety of the bus, in true Carrie Bradshaw end-of-episode style, I typed the following words in my head:

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"Was it really the medication? Or was I just too settled now with my own Mr Big, or too Welsh, to get it any more? Or maybe, just maybe, it was something far more simple. Somewhere in between the last episode and this day, had I finally gone down the path of all women, and turned into my mother?"