In bed with Madonna's brother

I AM in a windowless room in the Manhattan offices of Simon & Schuster, where I am to read a book that has been surrounded by so much hype it has caused a storm of controversy before it has even been published.

In Life With My Sister Madonna, Christopher Ciccone starts off by telling us he was born his mother's son but will die his sister's brother. The book is his attempt to readdress this, but the waters are dark and murky along the way. If you thought Madonna's book Sex, which features the singer all trussed up in leather and handcuffs, was as close as she got to S&M, think again.

But the book's true shock value lies less in Christopher's salacious revelations about his sister – of which there are plenty – and more in the bizarre nature of their relationship. Just a few pages in, we learn that Madonna – known for her fondness for racy outfits and who apparently likes to wear fishnets at all times, even under jeans – can't bear anyone apart from her brother to see her naked.

It goes on. We discover that Madonna is a control freak – he alleges that she once turned off the mic of her backing singer Nikki because she knew she was a better singer than her. We find out that when Madonna first began to perform, Christopher learnt how to give insincere applause. She was always a brilliant dancer, but he'd tell her that she had a great voice and, no, she wasn't fat. Later, he told her he'd lied to make her feel better. Yes, she was fat. No, she couldn't sing.

What he reveals is a vulnerable, needy Madonna, a Madonna that not many others have seen because she hides her insecurities so well. More than this, though, Christopher exposes himself as a brother who felt as if he had nothing left to lose. He believes his sister yanked his chain until she choked him, and in the process created her worst nightmare. All the nakedness of her mind, body and soul are told in excruciating minutiae. What was the tipping point for Christopher?

The next day, on the terrace of a café in the Meatpacking district, I meet Christopher. He has a gentle handshake and sad eyes. He likes my perfume. The sad eyes change to searching. He's wearing jeans and a T-shirt, his face chameleon-like, sometimes looking much younger than his 47 years, sometimes not. Sometimes he looks Italian-handsome, and sometimes his features disappear.

In his eyes you can see the darkness. In truth, all of Madonna's five siblings have probably experienced that darkness. They've just lived with it in different ways. Rupert Everett said that Christopher was her dark side and she was his. But he was also, according to Everett, "a solid raft in shark-infested waters". So when did he decide to swim with the sharks, when he decided to write the book? "It happened in stages," he says. "Our relationship was very strained back in 2003, and over a period of three or four years I got a chance to look back on it. I had some therapy and did some soul-searching. I had been attached to her life for so long, and it was hard to see myself as a separate person."

Christopher is the middle brother. He has always searched for identity. In the beginning, of course, it was easy to follow his older sister. It seemed natural, but then it got to seem very unnatural. "I finally got to redefine myself, and that is what the book is for me."

Yes, but isn't it a bit of a paradox that you're redefining yourself through her? "Hmm," he says. He gives a hollow chuckle. "Our lives can never be fully unwound. But now I can walk past a store and hear her song playing and I don't get a knot in my stomach. Somebody can talk about her at dinner and the hair on the back of my neck doesn't stand up, my defences don't automatically rise when her name is mentioned." Were you each other's dark side? "Well, yes, on some level. I was doing the things she wanted to be doing. I can be dark, that's my personality. But she certainly couldn't do things or experiment artistically without it being public, although now I think she should experiment artistically and work with people who are cutting-edge.

"She doesn't need the money. She should expand her mind and her musical sensibility, but she doesn't do that. She goes back to the sex thing and it doesn't work now – it's kind of creepy." Then he pulls himself back. "It doesn't diminish the fact that, when she's on it and she's connected to the audience, she is brilliant."

He says he still loves her but has felt better since she's been out of his life. She has accused him of being a drug addict. He says he only took drugs socially. "My only drug was her. That was what I was addicted to."

All her life, according to Christopher, Madonna has been able to suck people in, flirt, cajole. He believes this was particularly true of their father. Their mother died of breast cancer when Madonna was five, a tragedy that has become part of her mythology. Why was she daddy's favourite? "Maybe because she looked like our mother, and because she had our mother's name."

She always had charisma and the confidence that Christopher lacked. When she moved to New York she invited him to come with her to learn to dance. Upon arrival at her dirty, cockroach-infested flat, she said, "You can't stay here. You'll have to find somewhere else."

The push-me-pull-you pattern has remained throughout their lives. She wanted him to choreograph her first tour, but only if he would be her dresser as well. He could be artistic director of the whole tour, but he wasn't allowed to stay in a hotel suite, only a single room. She wanted him to design the interior of her house, but only if he could be paid when she felt like it. She refused to sign a contract for his work. She asked him to buy some paintings at Sotheby's, then told him to take them back. He'd paid 65,000 of his own money, and Sotheby's doesn't offer refunds. It was all the money he had, and he couldn't afford to pay for the roof over his head. And he says it went on… She told him the script he wrote was wonderful. He could sit and work from her offices in LA. But would she lend her name as executive producer? No.

Sometimes there would be conditions to his getting paid for his interior-design work. He'd have to take up Kabbalah. He'd have to accept payment in terms of a flight to Scotland to attend her wedding to Guy Ritchie, whom he had already clashed with. But life with his sister was exciting. It was private jets. It was partying with any celebrity on the planet.

I tell him this is the same neural circuit as a cocaine hit. It has the masochistic aspect of a gambler. You keep going because you hope you'll get the good stuff back. A sadist never stops, but a masochist can finally take back the power and say stop. "And that's what I did."

Christopher is a man where small expressions speak volumes. It's just a little sigh, but it's a very deep one. "It took an e-mail accusing me of stealing from her, of swindling her after 20 years of being the only person who hadn't." But there were many nails in the coffin of their relationship. Being paid with that air ticket, to a wedding he really didn't want to go to, "irked me," he says, "and it set up the whole wedding to be a disaster. But what could I do? At that point I was broke."

Christopher did not always just work for Madonna. The first restaurant he designed in Los Angeles was the Atlantic. It looked like a 1920s art deco ocean liner. His second was the Central, which suddenly closed before he'd been paid. Whenever he was doing well away from Madonna, she'd bring him back into the fold. His relationship with his boyfriend of ten years, Danny, certainly had its dysfunctional moments, usually precipitated when Madonna would call him away on an 18-month tour.

Madonna always called the shots, and he always took them. "I don't think this book was just about catharsis for me. Revisiting these places has actually been really painful. She opened a lot of creative doors for me, and she can be incredibly generous, but…

"The last time I saw Madonna was in Miami, for her last tour. We were cordial. When she found out about the book we already hadn't spoken for a year. All I got was a curt command by e-mail: 'Call me'. Since I don't respond to commands any more, I didn't call her, and after that she left a message. I didn't respond to that either. I knew what it was about. Giving her any measure of control would have destroyed it. Madonna's thing is control. There are three things in her life that she can't control that are happening in her world right now: she's turning 50, her husband and this book… And it's driving her crazy. She's in a twist about it. Rather than trust her instincts with me, she went for the worst possible scenario. You would think, after 47 years, your sister would know you, but the fact is she doesn't."

In the book, he says that his sister has no real need or curiosity to know about other people. In her head, they need to know her. Some narcissistic tendencies at work? He laughs, "It's not a tendency, it's a lifestyle. But you don't get to where she is by not being narcissistic." He orders a ginger ale and I order coffee, and a frittata of mozzarella, basil and tomato. Christopher doesn't eat.

He isn't in a relationship right now. He felt he had to do a lot of therapy before he was ready. There is a warmth to him, but also an emotional distance; a man still finding his own levels of comfort with the world. His two older brothers were boisterous and macho. The two younger sisters were the babies of the family. Christopher, possibly the most artistic, was always the least connected with himself – and the world. He looks offended when I say this. "I'm not out of touch. I do my own laundry." When I say I mean emotionally disconnected, he agrees.

The early loss of their mother affected them all. It affected how they felt they could express themselves. He says that rather than feeling Italian, he feels Midwestern – self-contained and afraid of emotions. If only he had stood up to his sister that first time she said he could only work on the dance numbers or at the show if he was her dresser. If only all that hurt and anger had not stayed inside him. Was it really all about losing his mother? "If my mother had lived, Madonna wouldn't have been Madonna. I was three when she died.

"All I knew of my mother was what her family told us. When I started to find out more, I stopped because I didn't want to destroy the image I had. For instance, my mother was very religious. Nothing wrong with that, but it was very intense, and things would have been very different if she'd lived, I have no doubt about it. I don't know if Madonna would have been possible.

"When we were growing up I didn't really know my sister. Every Christmas we would draw names out of a bag to see who we were going to buy presents for. One year I got Madonna's. I had no money and I got caught shoplifting some perfume. It wasn't because I loved my sister so much. I didn't really know her. She was a name in a bag.

"I never felt myself at home when I was a child. When you are a big family you sort of get mixed into the pot. Although we have similarities, there are big differences. Madonna was precocious and my father would naturally gravitate towards her. I was the middle boy and shy."

He claims that Madonna has worked over their childhood and turned it into a revisionist history. She likes to tell stories that her older brothers hung her up on a washing line. Christopher says this is embellished. "Worst of all is what she was saying about my stepmother – that she was wicked. I think my stepmother, Joan, deserves a medal for taking on my dad and six kids."

He says he let go of all that stuff a long time ago, but Madonna still holds on to it. "She likes to think of it as part of her mythology. It's a bubble in which she lives." The Cinderella, with the wicked stepmother, who arrives penniless on the streets of New York to make her fortune – when, in fact, she had a solid middle-class background. Christopher says that this might be what she had in common with Guy Ritchie, who gives us the myth of the geezer, a boy brought up on the wrong side of the tracks, but who was actually incredibly middle class.

None the less, how she can affect people is bigger than her own mythology. It's real. Even now, when we talk about the dark things, he feels compelled to say something good about her. It's the same cycle as always – pain-pleasure. "For me, the moment we peaked together was the moment she spat a cough drop in my hand when we opened at Wembley (The Girlie Show, 1993). It was an incredible feeling, the electricity of the audience washing through us. It was an incredible high, and, yes, her life was a drug to me in many ways, meeting all those stars.

"But at some point you realise you're not one of them and you can't afford to keep up with them. Suddenly it's like, 'No, I can't meet you in St Tropez because I've only got 10 in the bank.' I remember the day I bought a 5 million Picasso for her, then walked back home to my sixth-floor walk-up with a bathroom in the hallway. It was incongruous."

After another ginger ale, he says, "My main concern with this book was not Madonna, but my parents. Her fame has been difficult on my entire family, something she refuses to recognise. Everything she does and says is a burden on our family, not a gift. I always think, is my father going to be uncomfortable with this?"

In fact, Silvio 'Tony' Ciccone comes over as quite the hero. At Christopher's lowest point – his relationship with Danny in tatters, his relationship with his sister in a trough – he moved home. He remembers his father assembled several boxes of his possessions shortly afterwards – love letters from Danny, mementoes of Madonna's tours – and he said, "Let's burn them all." Christopher says, "I felt more connected to him then than I'd ever done in my whole life. But I'm not a crier."

There are so many times when Christopher believes his relationship with Madonna should have been destroyed. "The first time was during the filming of In Bed with Madonna, when she was rolling around on our mother's grave for the camera."

Soon after this, Christopher feels that she chose to exploit his gayness. She outed him in an article. "At that point everybody in my immediate family knew I was gay, but not my grandmother. Madonna couldn't understand why I was so upset. It was not her business to out me. I think she must have been feeling that she'd gone very mainstream. She'd done S&M, she'd done Sex, what she really needed was a gay brother." At the time, he tried to forgive her. But he could not forget.

He certainly had a lot of pain to suppress. Is that why he partied so hard? "I think it dulls pain." Madonna always insisted that he was a drug addict. She organised therapists, but even they did not recommend rehab. Christopher was just an unhappy guy trapped by his own choices.

Madonna has her own way of blotting out unpleasantness, according to Christopher: she simply puts on blinkers. What she deems unpleasant and unnecessary, she swiftly moves through. When Christopher broke up with Danny, she shrugged and said, "I never liked him anyway."

Christopher didn't just work with Madonna. He was always there, helping and comforting her when her biological clock ticked with painful resonance. "She needed someone to fill the daddy chair." But when she found Carlos Leon, father of Lourdes, the relationship was more than just that. She really loved him. It hurt her terribly when they broke up. Once again, this exposes Madonna in a way that would make her wince, according to Christopher: "Because I've made her human."

He looks wounded when I mention Lourdes. He will never see her grow up, and she reminds him so much of Madonna as a little girl. He doesn't know Rocco and hasn't met David. It is evident that separating from Madonna must have been like tearing his own skin off.

There was lots of competition between her and Sean Penn, her first husband, and now between her and Ritchie. Changing the balance of power, the surrender and conquest are what thrilled her. With Penn, though, it became a little too thrilling. During the filming of Shanghai Surprise, Christopher was staying in the room next door when he heard them fighting in the middle of the night.

In her next macho marriage, she turns to Kabbalah for comfort. "For a time I think she enjoyed playing the English lady. I don't think she enjoys it any more. Guy may not be the perfect person for her, but he was okay, and she wanted a family," says Christopher. "Much as I dislike him, I wouldn't wish them to divorce. But look, they are living separate lives… Guy's not had a successful film for some time, and her career continues. He's got to be feeling emasculated by this."

When Madonna refused to pay Christopher for his work on one of her LA houses unless he took up Kabbalah, he admits that he accepted. "Much as I hated her for that, I actually got some good stuff from it. But it got so cultish, I had to walk away. I am still a Catholic boy at heart. Catholicism and Kabbalah do not necessarily conflict, but Kabbalah ended up validating Madonna for her bad behaviour," he says. "The theory is that on some level you are who you deserve to be. And since she was in a position of power and wealth, she thought she deserved to be there and was closer to God than the rest of us."

As a Catholic, you believe that God is the ultimate power. In Kabbalah, there is nothing you can't do, so he says it helps her believe she can control God. "After we had our last falling out, I was excommunicated from the Kabbalah meetings."

Before being banished, he'd become friendly with Kabbalah fan Demi Moore, who he says saw him as a surrogate boyfriend. She kept asking him to turn straight. He didn't, but he did make out with Courtney Love. So why Courtney and not Demi? "Because Demi was too easy. Courtney was much more interesting."

We talk about Madonna's own flexible sexuality. She has publicly kissed Britney Spears and Christina Aguilera, and the gay model Ingrid Casares was her "girl toy", according to Christopher. She would sit at Madonna's feet looking up at her adoringly. She would beg to sit next to her at parties. Sometimes Madonna would allow it. They would do girlie things together, but he says they were both in love with Madonna. So what does he think she means with her flirtations? "It's publicity. She craves attention, and it doesn't really matter where it comes from."

Everyone in Madonna's orbit was desperate to get closer to the singer. He describes in his book the various stages. Stage four "is the coldest place of all. That's right up close to her. As far as she's concerned, that's too close for comfort. You know too much. You're a liability." The result, stage five, is "No more Madonna". He always knew what would happen when he reached that very close, very cold place. No more Madonna.

"I used to play with her by signing letters, 'Your humble servant', because I knew it irked her. It was my way of saying, 'Don't treat me this way' without having to say it straight out. Madonna is not someone you approach directly. You have to plant a seed, wait for it to be her idea, and then she can deal with it."

The truth is he did feel like a servant. But just as much as she couldn't hear it, he couldn't say it. His father, he says, was a stoical man. His feelings were heartfelt, but never spoken. Without a mother to give emotional balance, both brother and sister kept their thoughts hidden. And that has been the making of Madonna, and the tragedy of their relationship. As he says in the book, "Madonna and I – two children forever yearning for their lost mother – could love and be loved as best we could."

Ultimately it comes down to just that: learning to love and express it properly. It has been a difficult journey. But perhaps this is the right time for Christopher. He is working on a reality TV show called Mind Your Decor, an ironic behind-the-scenes look at the making of a decorating show. After that, he'd like to work with his father in the Ciccone vineyards in Michigan, and maybe do a show about a year in the life of a vineyard. His own person at last.

Life with My Sister Madonna (Simon & Schuster, £17.99)