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Ian is a captain in the Paras.

This week he'll tell the Army he is having a sex change.

By Elizabeth Day

At first glance, Captain Ian Hamilton looks no different to any other paratrooper. A snapshot taken of him on a tour of duty in Iraq shows him squinting into the sunlight, his well-built frame set squarely against the desert horizon.

He is wearing combat fatigues, his sleeves rolled up to reveal muscular, tanned forearms. A rugged smile plays across his face.

But then you notice his stance. One foot is placed carefully in front of the other, the military boots elegantly angled away from each other. It is almost the pose of a catwalk model, designed to show her legs to the best advantage.

Scroll down for more...

 Top: Captain Ian Hamilton;   Below: Jan and girlfriend Rachel Ward

‘I know!’ Ian says now. ‘You can tell that I wasn’t your average Para, standing there like a ballerina.’

To say he was not an average Para is something of an understatement. Three months ago, Captain Hamilton, 42, a decorated officer who also served in Bosnia and Afghanistan, took the extraordinary decision to become a woman.

He is the first officer and the first paratrooper in the history of the Armed Forces to choose to undergo a sex-change operation. The decision is the culmination of four decades of psychological turmoil, during which Ian had the inner conviction that he was born a woman.

It is this woman, Jan, who sits in front of me now, a well-groomed and elegant lady, her face framed by carefully styled brown hair, cut in feathered layers down to her jaw-line. Her lips are slicked in a glossy brown lipstick from Estee Lauder and she wears a floral, knee-length skirt and a white, long-sleeved T-shirt.

Apart from a slight thickening around the neck and a light dusting of stubble beneath carefully applied foundation, the effect is convincing. ‘Although my body is male, my mind is female,’ Jan explains, talking publicly for the first time.

‘I wanted how I look on the outside to match how I feel on the inside. I have to do this, because if I didn’t, you’d be coming to my funeral.’

Neither her colleagues nor the Army know that Captain Ian Hamilton has been living as a woman since January and will be having gender reassignment surgery over the next two years.

Jan has been able to undergo her recent transformation quietly and discreetly while working in the Army’s media operations department on a freelance basis from her home in the North of England.

But now, she feels, it is time to go public. And she has enough experience of the military ethos to know that she can expect a certain amount of disbelief and disapprobation. The Parachute regiment, after all, has a reputation for selecting only the toughest and most red-blooded men.

‘I expect a lot of hate mail,’ she says in a soft but undeniably husky Scottish lilt. ‘I will have to resign from the regiment because women are not allowed in frontline combat. It is important to me that I am not mocked. I have served my country for long enough and to the best of my ability and I don’t deserve that.’

But although Jan is sincere and articulate, it is clear that she is still struggling to discover her female identity. While her icons are glamorous, extravagantly dressed women such as Shirley Bassey and Sophia Loren, she herself is inclined to dress conservatively in long skirts and tailored jackets in muted colours.

Nor does she find men sexually attractive, describing herself as ‘a male lesbian’ – something that her former heterosexual girlfriend, Rachel, a 35-year-old freelance journalist whom she met in 2005, has understandably found exceptionally difficult to come to terms with. They now live together ‘as best friends or sisters’, but this is plainly an uneasy compromise for both of them.

Jan’s sexuality is, she admits, ‘a grey area’. ‘People might ask why I don’t stay a man, but that is to misunderstand the entire dynamic,’ she explains. ‘For a man to be with a woman, it is about domination. For a woman – for me – love is an emotional journey.

‘I don’t know how my attitude to sexual relationships will manifest itself in two years’ time, but I don’t enjoy men’s company.

‘I don’t want to be on my own for the rest of my life, but I’m reconciled to the fact that the price of my happiness is going to involve compromise, and that might mean not being in a relationship.’

She confides: ‘There are days when it is emotionally very bleak and I cry a lot, but I’ve never once doubted what I’m doing. As a man, I could never express emotion because I was scared people could see inside. So this has also been a wonderful journey for me.’

It was a journey that started in a fishing village on the North East coast of Scotland where Ian Hamilton was brought up in an environment of working-class aspiration. His father was a strict traditionalist who saved hard to afford to send his son to a boys’ boarding school overseas at the age of ten. By then, Ian already felt a sense of otherness – he wore women’s tights under his uniform trousers and was bullied by the other boys.

‘It was very lonely. You’re talking about the Seventies – I couldn’t ask anyone why I was the way I was because there was no social reference point. So I began to feel guilty.

‘My father loved watching gangster movies and I remember seeing the film The French Connection on TV in 1976. There is a scene in an underground club where The Three Degrees are singing I’m Not A Child, I’m A Woman. I used to play that song over and over again in my bed at night.

‘I remember looking at their big, bouffant hair and slinky dresses and thinking they were just so gorgeous – everything I wanted to be.I used to bunk off school sports days and dress up as a woman and go into town, doing girly things. It was great. I went for coffee, I read the papers and no one could tell. I had long hair and I’d steal clothes off washing lines and dress in kaftans, wedges and flares.’

At school he was given the role of Maria, the female lead in a stage production of West Side Story, which, Jan says, was ‘fantastic – it gave some legitimate release to how I was feeling inside but it also got me more confused’.

This sense of dislocation was heightened when a male teacher started sexually abusing him – something that, to this day, Jan refuses to talk about. It has left her with an abiding fear and hatred of male intimacy. ‘I think I made a subconscious decision then that no man would ever touch me like that again,’ she says quietly. Yet in 1983, when Ian left school at 18, he went to Sandhurst.

Why, one wonders, did this mild-mannered, conflicted young man pursue such an aggressively masculine career?

‘I was lost,’ Jan explains. ‘I thought, if I go into the Army, I can become a tough guy who doesn’t get hit, who doesn’t get abused.’

It was also a decision to meet his parents’ expectations. His father wanted Ian to epitomise his own masculine values. When Ian said he wanted to become an actor, his parents left him in no doubt that it was not a fit job for a man. With no outlet for his feminine feelings, he suppressed this side of himself completely. But he was unhappy at Sandhurst, his inclinations towards femininity sitting uneasily with the boisterous camaraderie of an Army barracks.

After 18 months and a posting to Berlin with the Royal Irish, Ian left the Army to retrain as a television cameraman.

From 1987, he spent nearly 11 years producing and directing documentaries for Scottish Television, Anglia and Granada, before becoming network editor at the now defunct Live TV! in 1997. His military experience meant that he was often posted to war zones, covering the first Gulf War and the conflict in Bosnia. Yet, when he returned to the privacy of his flat in Glasgow after each trip, he would dress up in women’s clothes.

On the outside, however, he continued to appear convincingly ‘aggressive and macho’. Jan says: ‘I was determined to cover every major conflict. Because of my surname – Hamilton – I was called Hambo.’

Indeed, so conventional was his life as a man that in 1995 Ian married a woman he had met at work several years earlier. The marriage lasted almost ten years but Ian was often abroad. They did not have children.

‘My wife had no idea,’ Jan recalls. ‘When we were living together it caused me great heartache because I was pretending. I genuinely loved her but I would secretly feel the fabrics of her clothes in the wardrobe.

‘My wife and I were very close, very intimate. But the sexual side of it went quite early on although we were still very much in love. I have a very complicated relationship with my body and I just couldn’t tell her. I was terrified.’

Eventually, Ian reached breaking point. ‘I was 35 and I thought, right, I’m going to sort my life out once and for all and that means I’m going back into the Army. I felt I had to prove my masculinity to everyone, to do something even more manly than I’d done before.’

His choice of the tough Parachute Regiment was part of this conscious camouflage.

‘I did the special Pegasus Company officer selection course, which was two weeks of incredibly hard physical tests,’ says Jan. ‘And at 35, I was really past it. We had to carry 35lb packs over ten miles in one hour 50 minutes. There was a lot of screaming and shouting but I did it to prove I was a man.

‘I forced myself to enjoy the camaraderie. I am still very, very proud of my beret and of being part of what I regard to be the best regiment in the Army.

‘At that stage, the female side of me was completely suppressed. I had killed it off. I was a total bloke – arrogant, aggressive and pushy. I was professional and extremely fit. I talked about shagging, took part in all that male banter.’

Ian insisted on taking the hardest and most demanding physical tests the Army could offer. Over the next three years, he became a qualified military physical instructor, took the Royal Marine Commando training course and passed the SAS Combat Survival and Resistance to Interrogation course, for which he was required to learn how to kill without a weapon and to go on the run for a week with 150 soldiers, dogs and helicopters in hot pursuit.

And he was, to all intents and purposes, a model officer. Over the next six years, he served in Afghanistan, Bosnia and Iraq, where he led soldiers from 4 Para, a reserve unit mobilised for service in the Gulf. In 2004, he started working as a staff officer for the Defence Media Operations Centre in Uxbridge, West London, where he was put in charge of media training for military personnel.

But the years of frontline service began to take their emotional toll. The following year, he suffered a breakdown and left his wife, who still did not know about her husband’s secret, although they have recently been reconciled.

‘I felt deeply upset at leaving her. I couldn’t work out what was really wrong with me,’ says Jan. ‘I didn’t know what to say or do and I felt a lot of shame and guilt.

‘For so long, my wife put my unhappiness down to the pressures of my job. She is a wonderful woman and she spent a long time wondering if it was her fault. It wasn’t.

‘The gender thing really raised its head when I was stressed. On the Army base in Uxbridge I dressed in women’s clothes in my room at night, then went to work as a Para the next day, remembering to wipe off my lipstick.’

Then an Army psychiatrist diagnosed Ian with post-traumatic stress disorder and he was signed off work. He returned home to the North East. It was to prove a turning point.

‘After that, I tried to reconcile the two elements and to live as a feminine man, but it was a constant war with myself,’ Jan admits. ‘I started wearing very colourful shirts, I had an increasingly gay wardrobe and wore make-up.’ But what about his girlfriend, Rachel, whom he had been dating since separating from his wife?

The couple met when Rachel came to the Uxbridge base as a media trainer and Ian, friendless and alone, valued her companionship. When he was signed off work, they moved in together. How, one wonders, did this vivacious blonde take the news that her Paratrooper boyfriend wanted to start wearing make-up and high heels?

‘It was hard for her because she thought I would get better, but there is no cure for people like me,’ says Jan. ‘Last Christmas, I was suicidal. I stood in the kitchen with a carving knife pointed at my heart, telling Rachel I just couldn’t go on like this.

‘She told me I needed help and I started seeing a counsellor. That made me realise that I wanted to live as a woman and I started dressing as Jan in February.

‘It has been a bereavement for Rachel. She has lost Ian. I’m more gentle, more considerate. I used to be intimidating, I always wanted to be in charge, but I don’t do that any more.’

Jan’s physical transformation will take time. At the moment she wears a wig and, at 6ft, still possesses the frame of a Paratrooper, with pronounced calf muscles and biceps. This will change gradually.

She is taking oestrogen to encourage the development of female sexual characteristics such as breasts, and an anti-androgen to reduce the effects of testosterone. She is, she tells me proudly, now up to a B-cup bra size.

The hormones have had other effects. ‘I can’t parallel park any more,’ she says with a laugh. ‘Honestly. I can’t even map-read. I’m too ditzy as a woman.’

The entire feminisation process takes up to five years and will cost Jan £20,000. She has opted to be treated privately, and must live as a woman for at least a year before being put forward for genital reassignment surgery. In August, she will fly to Thailand to undergo facial surgery by one of the top specialists in transsexual medicine.

Her brows and eyes will be lifted, her forehead reshaped, excess flesh from her jaw-line removed and rhinoplasty will leave her with a delicate snub nose.

Next year, she plans breast augmentation. ‘It’s major surgery and I am nervous,’ Jan says. ‘Who would put themselves through this if there was any other way?’

Whether the Army will be sympathetic remains to be seen. The 2004 Gender Recognition Act stipulates that transsexuals must be accorded equal treatment by employers and there have been similar cases – seven years ago, an RAF officer, Flight Lieutenant Eric Cookson, had a sex change to become Caroline Paige and returned to flying duties.

Although Jan will have to resign from her regiment, she has been offered a two-year contract as head of media operations for the British Army in Gibraltar, which she hopes to take up next month, but she got the job without revealing her plans to become a woman.

Her parents are still coming to terms with the shocking news that their macho son is now a daughter, but most of Jan’s friends have been extremely supportive.

She knows that when her story becomes public, not everyone will be so understanding.

‘You can’t begin to understand the pain,’ she says, her eyes reddening and her voice barely a whisper.

‘When people laugh at me, I want to say to them, I was once the man you wanted me to be and I just couldn’t do it any more. I couldn’t keep living my life for everyone else.’

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