It’s December 31, 1999. Donatella Versace has a New Year’s Eve party at Casa Casuarina, her Miami mansion, where I first meet Guy Ritchie, the new man in Madonna’s life. He is personable and respectful and seems as if he might be fun to hang out with. Nonetheless, I doubt he’ll outlast my big sister’s usual two-year relationship cycle.

By four in the morning Madonna is dancing on the table. Gwyneth Paltrow joins her and they dance together. In the middle of the dance, Madonna grabs Gwyneth and kisses her full on the mouth. It’s that sort of a night.

My friend Dan has brought a 19-year-old boy I call Scratchy. Madonna, in a knee-length pink chiffon Versace dress, is now on the dance floor. Suddenly Scratchy squeezes up to her, puts his arms around her, and they dance a slow dance close together. Within an instant, Guy strides across the dance floor, kicks Scratchy in the leg to get his attention and drags him away from Madonna. Then he swings his fist at him. I push Guy back and yank Scratchy out of the room.

The moment passes. I’m dancing with Gwyneth. Suddenly I sense someone coming up behind me. Guy grabs me from behind and starts bouncing me up and down like a rag doll.

“Put me down!” I say. I extract myself from his iron grip. I shove him up against the wall, push into him and grind my hips right into him. “If you want to dance with me, this is how we dance here,” I say grimly. He flushes and pushes me off.

The next day most of us are so hung over that we just chill out, lounge by the pool and speak softly. Guy and I don’t say a word to each other.

I decide he is a bit of an oaf, particularly on the dance floor, a drawback with regard to Madonna, as she likes her lovers to dance well. Above all, it has always been of paramount importance to Madonna that the man in her life be able to deal with the gay men in her life.

I can’t imagine that Guy will be around for long. I am wrong, of course. Barely three months later, on March 20, 2000, Madonna announces that she is pregnant with Guy’s child. I am still not convinced that he is in her life to stay. She had Lola, her daughter, with Carlos Leon, a personal trainer she met in Central Park, but didn’t stay with him.

On August 11 their son Rocco is born.

Madonna breaks the news to me that she and Guy are getting married. I am glad for her, because I realise that she is vulnerable and needs him.

Apart from the fact that Guy must remind her of Sean Penn, her first husband – both are from comfortable homes yet are prone to present themselves as tough street kids – she is getting older and needs a father for her children.

She casts such a big shadow and most men just aren’t prepared to subjugate themselves to her. I guess that Guy isn’t either, but at least he is prepared to marry her.

Madonna is now permanently based in England – which she and I disliked so much during our first trip there together in 1984, when she appeared on Top of the Pops.

She and I are in dispute over payment for interior design work I’ve done on her former home in Coconut Grove, Florida. My finances are in a shambles.

On October 9, 2000, she sends me a letter saying that she is putting her “indignation aside” – referring to our payment dispute – and inviting me to her wedding in Scotland. In a backhanded compliment, she says she is inviting “my close friends and family members that are not insane”.

I am not keen to attend the wedding, as I really can’t afford it. So I call to make my apologies. Madonna isn’t around, but her assistant Caresse calls me back: “Madonna told me to tell you if you want to be paid the final payment for Coconut Grove, you have to use the money to buy a ticket to her wedding.”

“You are joking, right? Because if you aren’t, then she is blackmailing me.” I hang up. Caresse calls back: “We are going to take the money Madonna owes you, buy you a ticket to Scotland and send you the money that is left over.”

I spend a few days mulling this over.

I am consoled by the thought that we can’t be on such bad terms as she really does seem to want me at her wedding.

So I capitulate.

Caresse gives me the rundown: a week before the wedding I will fly to London and then to Inverness, a 45-minute drive from Skibo Castle on the shores of Dornoch Firth in the Scottish Highlands. On December 21 Rocco will be christened and the wedding will take place on December 22.

Later I discover that none of the guests is allowed a mobile phone and that we are all banned from leaving the castle during the five-day wedding celebrations. Moreover, 70 security guards will be on hand to ensure that no press infiltrates Skibo (and no guest escapes).

A business-class British Airways ticket is messengered to me from Madonna’s office. When I check the price, I discover that only a few hundred dollars of my final fee remain. After the flights, a car meets me at Inverness airport. At Dornoch, we drive up a sweeping beech-lined drive and Skibo Castle looms in the mist: big, beautiful and mysterious. A crackling log fire burns in the main hall. I expect Errol Flynn to swagger down the magnificent staircase and start fencing with me. I follow a kilted “greeter” to my accommodation, assuming that it will be baronial and splendid. We walk up two flights, three flights. We walk up four flights, five flights. We walk up six. Along the way we pass various suites, all magnificent, all with four-poster beds and furnished with antiques.

My room is on the top floor in a turret attic. I go through a little door into a small hallway, then into a room about 6ft by 6ft with a claw-footed Victorian bathtub in the middle and a toilet against the wall. That leads to another doorway, another low ceilinged room, and there is my bed.

The phone rings and I am informed that dinner will be at eight. Moreover, it is black tie. Madonna never warned me that there would be black tie events. I’ve only brought one suit with me – Prada. It looks like I’ll be wearing it every night.

I go down the six flights of stairs. I pass a library and a billiards room. I take a walk outside, see the small gym and serene spa and the Edwardian indoor swimming pool. A pretty girl rides by on a horse. She introduces herself to me as Stella. The penny drops. Stella McCartney. As far as I know, she and Madonna have only just met, yet Madonna has chosen her to be her maid of honour. Stella designs and makes a free $30,000 dress specially for Madonna.

Stella explains the drill to me. Every morning the men will go shooting and the women will have a themed luncheon. S h e k n o w s , because Madonna has told her.

“So I either have to go to lunch with the women or go shooting?” I ask Stel-la.

She tells me that no men are allowed at the lunches. But shooting is out of the question for me.

I dress for dinner, then go into the library. Guy’s friends are in there. I don’t know any of them, but one or two look familiar so I guess I’ve seen them in some film or another. They are relatively friendly and they all clearly have a history with one another.

We have cocktails and I try to make small talk. I ask how the shooting went and they tell me that they have shot 300 birds. I ask them if they are kidding. They tell me they aren’t. They are going to get hung up, where they are meant to rot. “So are we having them for dinner?” I ask. They all laugh and tell me that we aren’t.

In the morning I am awoken by a bagpiper playing under my window. When I go down to breakfast I discover that I am condemned to spend the day on my own.

So I work out and then read. I’m curious about what’s going on in the girls’ room. It’s all very hush-hush. After a while, Stella comes out and says, “I’m tired of the girls. I’m going to ride my horse.”

In the evening I sit at dinner between Trudie Styler and Sting, who introduced Guy to Madonna. At first they talk about the castle and the weather. Then Trudie leans in to me and says, “Christopher, do I have BO?” “Huh?” “Do I have BO? Do I smell?” “Not that I can tell,” I say, perplexed. “Are you into that sort of thing?” Before I can think of an answer, she chips in, “Mightn’t you be?”

“Isn’t the smoked salmon delicious?” I say.

Guy’s pride in his own heterosexuality swells noticeably when he’s in the presence of a gay man like me. And during this wedding week, when there are nightly after-dinner toasts made by his male friends – many of which are aimed at underscoring his overt masculinity – he is in his element.

I, however, am far from amused when many of the speeches trumpeting Guy’s heterosexuality include the word poofter, which I know is a derogatory British expression for gay.

Madonna, who is at the head of the baronial table, stands up one evening and issues an instruction: “Christopher, tonight it’s your turn to give the toast.”

I lean down the table and, with great emphasis, reply, “Madonna, you really don’t want me to do that.”

It’s a statement, not a question. Madonna looks back at me blankly.

“No, Christopher, it’s your turn!” she barks in a tone identical to the one she always used as a kid when we played Monopoly. If she didn’t get Park Place, she invariably stamped her feet and said, “But it’s mine!”

In those days, in the face of her strong will, I always capitulated. Nothing seems to have changed. I stand up.

My fellow guests fall silent out of respect; the brother of the bride is about to make a speech. I raise my glass: “I’d like to toast this happy moment that comes only twice in a person’s lifetime.” Without skipping a beat, I go on, “And if anybody wants to f*** Guy, he’ll be in my room later.”

Everyone erupts in peals of laughter. Everyone except Madonna, who keeps saying, “What did he mean? What did he mean?”

I’m walking to my room later, thinking that at least I got my dagger in, when Trudie comes up behind me. “That was hysterical,” she says. “Your sister didn’t get it, but I’ve been listening to all those homophobic jokes and if you weren’t pissed off I’d be worried about you. I just want you to know that we were aware of how you must be feeling.”

The next day my parents arrive, along with my sister Paula. Initially, Madonna didn’t invite her. Paula tells me that she called Madonna and said she really wanted to be at her wedding, and Madonna said that as long as Paula paid her way she could come. She is working as a graphic artist and earns only a modest salary. Yet Madonna still expects her to pay her own plane fare to this far-flung place.

My mood improves when Rupert Everett, Gwyneth and Donatella arrive. We take a golf-cart ride and I tell them about the homophobic toasts and how awful everything has been. They laugh and console me. Gwyneth says, “Poor Christopher, we’ll look after you.”

The christening is in the evening. A long line of Range Rovers pulls up in front of the castle to take us to Dornoch cathedral. A pack of 500 photographers and even more journalists is waiting at the castle gate and follows us. More than a thousand fans are gathered outside the small, 776-year-old cathedral. Inside it is lit with candles and garlanded with ivy and flowers.

I sit with Gwyneth and Rupert and only see Rocco – swaddled in his white-and-gold $45,000 Versace christening outfit, a gift from Donatella – from a distance. I learn afterwards that a journalist has been hiding in the massive pipe organ for three days. By the time someone discovers him, he has passed out cold.

Guy Oseary, Madonna’s manager, has been awarded the distinction of being Rocco’s godfather. I try not to mind. We are driven back to the house, with the press following close behind. Dinner is served, toasts are given. I experience a sudden urge to smoke but know that I can’t as Madonna has banned smoking.

Gwyneth and I leave at the same time. On the way up to my room we stop at her suite, which is massive and beautiful. It occurs to me that I have been relegated to what must be one of the smallest rooms in the castle, perhaps even the servants’ quarters. A joke? Or just my sister’s way of keeping me in my place?

The next evening we all gather for the wedding ceremony in the Great Hall, now lit by candles, and take our seats at the foot of the staircase, which is garlanded in ivy and white orchids. Lola, in a long ivory high-necked dress, descends, scattering red rose petals.

She is sweet, winsome and adorable. I feel sad that all week she has been with either her nanny or her nurse, or sequestered in the locked room with Madonna and the other girls. I would have liked the opportunity to get to know her better.

Madonna, beautiful in a fitted ivory silk dress, joins Guy on the staircase. He is wearing a kilt that someone explains to me is in the plaid of the Mackintosh clan. Rocco, snuggling in his nanny’s arms, is dressed in a kilt of identical fabric.

Guy and Madonna exchange diamond wedding rings. Then, in front of a female pastor, they speak the vows they’ve written themselves. I wish I could hear them, but the ceremony is so far from where we are all sitting that none of us can make out a word. Deja vu – Sean and Madonna’s wedding in Malibu all over again. We couldn’t hear a single word of the vows then because we were deafened by the racket of press helicopters above us.

Later we are piped into dinner. The best man, nightclub owner Piers Adam, stands up to give his toast. Behind him, a screen features images of Guy as a baby, Guy as a schoolboy, and even Guy in a dress. One picture shows Guy as a child, lying across a black dog, with his hand near the dog’s penis. Piers Adams points at it. “You see, Guy was a poofter early on,” he chortles.

I restrain myself from throwing a plate at him. I glance at my sister, hoping to see a look of outrage on her face, but there is none. I am sad that Madonna, whose early success was built on her legions of gay fans, can listen to these antigay comments without protesting. I feel even sadder that she is now married to a man who seems so insecure in his masculinity that he thrives on homo-phobia, and his friends know it.

I leave the dinner, go upstairs and fall asleep. I wake up at around two in the morning and go downstairs to get something to eat. I hear music coming from the castle’s cellars. A big party is going on and everyone is dancing. Among them is Madonna’s maid from America. While a nice gesture that she paid her maid’s way, it is almost beyond my comprehension that she categorically refused to pay for our sister Paula to fly to Scotland as well.

But she makes a conciliatory gesture towards me, suggesting that I stay at her Holland Park home on Christmas Eve, then on Christmas Day join her and Guy at Sting and Trudie’s Wiltshire estate, where the newlyweds are spending their honeymoon. Once I get there, the honeymooners keep to themselves and I hang out with Trudie and Sting. At dusk, Sting and I walk around the 52-acre property together.

He and Trudie keep sheep and they run everywhere. There is also a little lake with an island in the middle, with a large tree growing on it. Sting tells me a story about a girl who died out there. According to him, at certain times of the year you can still see her ghost, dressed in a white gown, sitting on a chair, gazing out over the lake.

The property is unmodernised and beautiful and I feel as if I have gone back in time. But even the serene surroundings and the kindness Sting and Trudie both show me don’t eradicate the unhappy memories of my week in Scotland.

When I arrive back home in America, open my mail and find an invitation to join Skibo’s exclusive private members’ club, I don’t, for one second, consider accepting it.

© Christopher Ciccone 2008

Extracted from Life with My Sister Madonna, by Christopher Ciccone with Wendy Leigh, published by Simon & Schuster, £17.99. Copies can be ordered for £16.19, including postage. Buy now from The Sunday Times Books First

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