Ayres in Kabul in June. During his last months in Afghanistan he was able to live more as a man. Credit:Andrew Quilty "At first I thought, 'Oh great, a lesbian movie,' " Ayres recalls. But, as the movie progressed, she began to see how much she had in common with the main character, Brandon Teena, a real-life transgender man who was raped and murdered by two friends once they discovered he had female genitalia. Ayres began to cry uncontrollably. "Oh, fuck," she thought to herself, as she sat, alone, bathed in the white sheets of a fancy hotel in the middle of Pakistan. "That's me. I am fucking transgender." S​ixteen years later, Ayres sits in his garden in Kabul – yes, Kabul, Afghanistan – with a contraband beer. He is now 49; his hair still short, but with more greys. A double mastectomy earlier this year removed his breasts. He had a hysterectomy 10 years ago, for health reasons. He will start testosterone injections soon. He has a few wispy hairs on his chin and wonders if he can start shaving yet.

Ayres at Band-e-Amir, Afghanistan, in his first week dressed as a man. “My journey through this [transition] has been really easy,” he says. “I just wish it was the same for everyone.” Credit:Andrew Quilty He also has a new name. Emma Ayres is now Eddie Guy Ayres. "I've waited a long time to do this," he says, lighting a cigarette. "I suppressed this for so long, now I feel I can't wait." Eddie Ayres thinks back to Pakistan. It was, he says, a "total beam of light" moment; where he saw the truth about who he was. But that truth was also a frightening "terrible realisation" – and one that he was entirely unprepared to deal with. Ayres at a barber’s shop in central Afghanistan: his first outwardly “male” activity in a country with extreme gender segregation. Credit:Andrew Quilty It would take Emma Ayres more than 15 years – and a life-changing 12 months in Afghanistan – to pluck up the courage to do something about it.

In early 2015, after six years at the ABC, Ayres moved to Kabul to teach violin, viola and cello at the Afghanistan National Institute of Music (ANIM). As a fellow Australian living in Kabul, I contacted Ayres early in 2016, curious to see how a former ABC radio presenter had adjusted to life teaching at a Kabul music school. We met there for the first time in April. "Hello, I'm Emma," was how Ayres introduced himself; exactly as I had imagined: big smile, that familiar warm voice, and dressed a little mannishly in a long red shirt, black pants and sandals. Eddie, formerly Emma Ayers, poses for a portrait in central Afghanistan's Bamiyan Province. Credit:Andrew Quilty I’ve noticed recently that as I’m appearing more male, straight women are being slightly flirtatious with me, and I’m learning how to deal with that. Eddie Ayres Afghanistan is still a country wracked by poverty, war and suicide bombings. But wedged between kebab shops and dusty side streets, ANIM feels like a genuine beacon of hope, a place where children – both boys and girls – revel in learning music and hold teachers like "Miss Emma" in very high regard. Watching children clutching violins dash in and out of Ayres' teaching room, a small space decorated with Afghan rugs and pictures of Beethoven and Schubert, makes Afghanistan's progress seem tangible. After all, just two decades earlier, the Taliban forbade music and sent out squads to crush instruments.

But for all the small pockets of wonder like ANIM, where teenage girls conduct orchestras and practise wonky versions of Abba songs on traditional instruments, Afghanistan is still a country where women are second-class citizens; where violence against women is endemic and child marriage rife. For women, socialising with unrelated men is frowned upon. Although not required by law, women cover their hair, ankles and wrists. The burqa is still common. Some women push these boundaries, but are harassed for it. When Ayres began at ANIM, he had already visited twice before as a guest teacher. So he knew Dr Ahmad Sarmast, ANIM's Afghan-Australian head, had been almost killed in a Taliban assassination attempt. He also knew that as a woman, he would have to wear a hijab, and opportunities to socialise with men would be rare. Many men wouldn't even shake his hand. For years, Ayres had used androgyny as an escape from the body he hated. That was no longer possible. "Being in Australia, you can live in the middle, you can dress as a man if you're a woman, you can ride a motorbike … and nobody really cares," says Ayres. "But here, you have to be a woman." Life in Afghanistan was already hard. There were the pot-holed streets, the power outages, the distressed students who screamed in terror when bombs exploded nearby. Then two suicide bombers were apprehended in the building adjacent to ANIM, believed to be plotting an attack on the school.

But the hardest thing for Ayres in Afghanistan, after 15 years of denial, was being recognised every day as a woman. Ayres was surprised how much the kids constantly singing out "Miss Emma" affected him. He began to despise his headscarf. "I'd weep at being stuck in this female body, it just wasn't me," he says. "I'd weep and I'd try to let it go, move on with my life." Ayres' housemate in Kabul, Jennifer Moberg, once told Ayres that Afghanistan "holds a mirror up to you" – that living there is so stressful that you learn who you really are. For Ayres, Afghanistan made him finally confront being transgender. It was time to stop lying – which he had done for so many years – to others, and to himself. Two hours after we first met, Ayres and I sat outside as the kids ran around on their lunch break. Ayres had previously mentioned a recent surgery in Australia, so I asked about it. Ayres paused. He no longer wanted to lie. So he explained he'd had a double mastectomy, and told me, for the first time, that he was a transgender person and he was in the process of transitioning. "Oh wow!" I said, taken by surprise. "Is that something I should congratulate you about?" "Yes," said Ayres, laughing. "I suppose it is."

When Ayres was eight years old, his mother, Anna, asked him what classical instrument he wanted to play. Ayres answered that he would like to learn the cello. "Cellos are for boys," his mother said. "You'll learn the violin." Born the youngest of four children – with two sisters, Liz and Penny, and a brother, Tim – Ayres grew up a true tomboy in Shrewsbury, a small town in the heart of England. He was confused when he was told at the age of 11 he could no longer run around without a shirt on. He hated girlie clothes, and his breasts, and fought bitterly about these things with his mother, a part-time civil servant and full-time single mother who was left to raise four children under the age of eight when their father left to marry the woman next door. At 14, fantasising about kissing girls, Ayres thought he had found the answer. ("I got to 'lesbian' and just stopped," he says now). Ayres liked his hair short and wearing men's clothes, and got a kick out of being mistaken for a man. He liked women. But transgender wasn't even a word in the early 1980s, and the few trans people who had been in the media – most outed, in shameful breaches of privacy – were largely trans women. Through his late teens and 20s, Ayres dated women, and became an accomplished musician, studying in Manchester and Berlin. He had discarded the violin. In his teens, a teacher suggested his large hands might be better suited to the bulkier, heavier viola. Ayres never overcame his desire to play the cello, that instrument his mother branded the domain of boys, but he was good at the middle ground. He loved the viola's deeper, richer sound and spent up to eight hours each day practising, until one day, at an audition in London, feeling ridiculous in a floral Laura Ashley dress, he was offered a real job, playing viola in the Hong Kong Philharmonic Orchestra. He would move there in 1992.

By 2014, Ayres had been in Australia for 11 years and had settled with a new partner in a "groovy" two-bedroom flat in Glebe, in Sydney's inner west, crammed with music and bicycles. By then, after a few trial runs at ABC's Classic FM radio station – his bosses weren't convinced listeners would like his British accent – Ayres was a stalwart, having hosted the breakfast slot for six years. Ayres was a divisive host, both loved and despised by listeners for his dry wit, on-air personal story-telling, and for sometimes flubbing the pronunciation of Australian towns. But he loved the job and his ratings were strong. "I was working four hours a day and getting paid more than $100,000," Ayres tells me. "Life was a piece of piss." In secret, Ayres had also begun shoving socks down his underwear and researching female-to-male transition. When Ayres' partner travelled for work, he would spend hours alone, obsessively watching YouTube videos of trans men triumphantly showing off results of surgery or talking about taking testosterone. The last two years have been a time of extraordinary visibility – and acceptance – for the global transgender community, with decades of advocacy work suddenly reaching a "transgender tipping point", as Time magazine put it in 2014. The celebrated trans icons of our time are now household names: Laverne Cox, the glamorous star of Orange Is the New Black; Chaz Bono (son of Sonny and Cher); and Australian military officer Catherine "Cate" McGregor. And, of course, Caitlyn Jenner, whose transition from Olympian and Kardashian patriarch to beautiful trans female advocate was one of the biggest news stories of 2015.

But while there has been remarkable progress, Australia's transgender community still faces discriminatory laws and deficient health services, according to Sally Goldner, executive director of Transgender Victoria. The Safe Schools debate, fighting over public bathrooms and polemics from people like Germaine Greer demonstrate that turning the corner "doesn't wipe out 30 years of negativity", says Goldner. Transgender people in Australia are four times likelier than the general population to have suffered depression, for instance. Nearly two-thirds report having experienced harassment, including violence, and discrimination. Caitlyn Jenner on the cover of Vanity Fair doesn't change that overnight. Ayres had been in denial about being transgender since Pakistan. He had confessed to a handful of people over the years, but not everyone was supportive. In particular, two of his former partners had expressed reservations. According to Ayres, both said if he transitioned, he would be an oddity, neither man nor woman, and their relationship couldn't continue. A recent US study has shown that nearly half of all relationships end when one partner comes out as a transgender person. It is not uncommon for transgender people to delay transition, or to decide never to do so, because of unsupportive partners, says Goldner, who adds that coming out to family members often involves fewer issues than doing so with a partner, "with possible loss of physical intimacy being the most obvious". Transitioning just seemed too hard. Ayres decided to learn to play the cello, that instrument for boys. He told himself his relationships were more important. He thought maybe he wasn't transgender, just androgynous. "I thought it was something I could deal with," he says. "I thought love would override it."

But he couldn't let go. A simple pair of socks in his underwear gave Ayres "the deepest sense of happiness I could imagine, but then it would quickly turn, knowing that it wasn't real". Looking at trans men with the courage to transition, all he felt was envy. By mid-2014, Ayres had spiralled deep into depression and was actively considering suicide. Desperate, he resigned from the ABC, realising he needed to take a dramatically different course. He had heard that a long-unfilled teaching position at ANIM was still vacant. He thought about all the giggling Afghan kids he'd met there on two earlier short-term teaching stints. Those kids who adored learning their instruments and practised hard because they knew music was one of their few chances for a better future. Those kids who didn't have a cello teacher because there wasn't anyone else qualified who wanted to risk moving to Afghanistan. "I felt everything was literally falling down on me," says Ayres. "I didn't just want to travel the world … I wanted to go somewhere I could do some good." And with that, his escape was plotted: to Afghanistan.

In February this year, Ayres undressed at a private medical clinic in Brisbane. Before he put on the green paper surgical gown and cap, he looked at himself in the mirror. He tossed the bra aside and laughed, thinking, "I won't have to wear this any more." The surgeon came in and drew lines across his breasts, marking where the incisions would be made. Then he was left alone, to wait. As Ayres listened to classical choral music to calm himself, he began to cry. "It was so enormous," he recalls. "I cried out of gratitude … I cried that I was having to do this, and I cried because I was doing it. I cried because I was happy I lived in a country like Australia where I could do it." He pauses. "I was also scared." Ayres had been scared for more than a decade. But now, at 49, he has learnt two key things. Kabul taught him that the middle way – being androgynous – was not enough. Just like the viola had not been enough. Second, after years fearing that no one would love him, Ayres has also learnt that, in fact, he has supportive people in his life. To his surprise, his mother, Anna, has been a loving, encouraging force. The two have had a difficult relationship at times, and it was Ayres' eldest sister, Liz, who broke the news to their mother. Ayres recently visited them both in England for the first time since he began his transition. When I call Anna, I tell her I call her youngest child "Eddie", and use male pronouns, like "him". That is something Anna hasn't got used to yet, she says. "I still think of him as Emma … this is still my daughter, my beautiful daughter who is having some changes."

Anna's voice wavers a little, as she begins crying. When Liz told her about Eddie, it came as a shock. She had never suspected. But she respects her child's choice, and is trying hard. One night soon after Ayres' mastectomy, his mother finished the call saying, "Goodnight, Eddie." "I'm going with the flow," Anna tells me. "I know that sounds corny, but you can only hope [your children] are happy and be happy for them." Liz also cries when I call her. At the end of a rare week catching up with Ayres, which began with Ayres showing off his chest ("I suppose it should have been weird but it wasn't," Liz says), she says she feels like she has gone into mourning for her sister: "She's always been my little sister." Liz had been upset by a discussion over how testosterone would change Ayres' voice. "I'd know her voice anywhere, you know what I mean? I guess I'm upset about those things going and never being there again," she says. "I just absolutely love and adore the person who is currently my sister and will be my brother, and I just hope to God it works out." Another pillar of support has been a woman called Carol "Charlie" Le Brocq. Le Brocq had been a longtime listener of Ayres, and the two struck up an unlikely friendship when Le Brocq offered to do Ayres' astrological charts. Ayres didn't really believe in the charts, but they stayed in touch, eventually becoming close. When Ayres told Le Brocq he had decided to transition, Le Brocq – a retired midwife – immediately offered assistance. As she helped Ayres recover after his double mastectomy – Ayres couldn't lift his arms for weeks – they fell in love, finally confessing their feelings after a boozy night out at the orchestra. "It was so easy for us," Le Brocq tells me.

Le Brocq, like all of Ayres' past partners, identifies as lesbian. I ask her if she has thought about being with a trans man. "I realise Eddie has a lot of physical changes and some emotional changes that are going to come up," she says. "For me, I want to be open to accept Eddie. I love Eddie as Eddie is now, but life isn't stuck in one frame, life has to keep moving." In his last three months in Afghanistan, after Ayres returned from his double mastectomy, he began living, more and more, as a man. He ditched the headscarves and rode motorcycles around Kabul. When he once gave me a ride on his motorbike, he wore blue jeans and a black leather jacket over a white T-shirt. Some Afghan men shot us disapproving looks. Not at Ayres, who they thought was a man – but at me, a foreign woman on a motorbike struggling to keep her headscarf from flying off. Before embarking on a testosterone regimen, Ayres still often found himself stuck in the middle. At the airport, Afghan security guards openly debated whether he was man or woman, unsure who should pat him down. Back in Australia, Ayres began monthly shots of testosterone in July. He is not having a phalloplasty (penis construction), because the surgical procedures involved are expensive and complex, and the results often disappointing. But he is excited about boosting his testosterone. He wants to be muscular, to have a full beard – the ideal he describes sounds a little like a buff Hell's Angel. He accepts that he might actually end up a short version of his brother, baldness included. Changes have already occurred, and fast. Within just one month of his first testosterone shot in July, Ayres had gained three kilograms, mainly muscle, and was thrilled to see more hair on his face.

His voice has also already changed; by Ayres' musician's calculations, it is already "a fifth" lower, or more than half an octave. As a radio presenter, he had been famous for his voice. Listeners would routinely describe it as sublime, dulcet, even magical. Given that he hasn't ruled out a return to radio, is he concerned about losing one of his strongest assets? "It is something I initially thought about," says Ayres. "I certainly always appreciated what people said about my voice." But, he notes, it isn't just about how his voice sounds, it's also about what he says to his audience. "What I say isn't going to change … I just see the voice as a vessel. I'm hoping I'll still have a nice voice but if I don't, that's okay. Nothing lasts forever." The process of hormonal transition is not just about physical appearance. Testosterone can alter behaviour. Socially, Ayres must also learn how to behave as a man, and how his new appearance can affect others. He tells how one of his trans friends, who has transitioned from female to male, was walking home one night recently when he noticed a female jogger crossing the road to avoid him. "I have to learn the role of being a man, and learn how to treat women," says Ayres. One day, Ayres and I go to Istalif, a beautiful area outside of Kabul famed for a centuries-old tradition of deep blue and emerald green pottery. On a short hike up a hill to check out an old Soviet tank, two men claiming to be police officers suddenly appear. We both laugh when the men ask if Ayres is my boyfriend, but soon decide to take off when they start behaving strangely. The men follow us and quickly flank me on either side – so unacceptable by standards of Afghan culture that it feels ominous. Ayres, suddenly shouts "HEY!" in protest, and forces himself next to me, to protect me. The men step back and eventually leave us alone.

Afterwards, I ask Ayres if he thinks he is growing into a more masculine self, stepping up to protect female companions. I'd already watched him, previously, at a brunch in Kabul, switch between back-slapping and talking about martial arts with men, then later, leaning forward to console a distressed female friend, talking in a soft voice. "I do remember that I wanted to be protective of [a former partner] and she hated it," Ayres says. Later, he adds, "I think I'm going to have to learn to be respectful, because all my life women have seen me as a woman and therefore probably non-threatening. Something that I've noticed recently as I'm appearing more male, straight women are being slightly flirtatious with me, and I'm learning how to deal with that." The first day I met Ayres, as I watched him give lessons, before he told me he was transgender, I jotted down in my notebook that with his strong cheekbones and ice-blue eyes, he looked like the actor Robin Wright – a woman. Everyone I speak to for this story – his housemates, family, Le Brocq – sometimes slips up, using "she", or "Emma". Andrew Quilty, the photographer for this story, agonises over how to greet Ayres – a kiss on the cheek, a hug or a handshake? Ayres understands that it can be an easy slip, especially now, before he has completed his transition. "If I'm sitting here in a year with a beard and you're still calling me Emma, then I might be a bit, C'mon," he says. "I have to be patient. This is a big change for me, but it's also a big change for my friends and family." While he hopes for – expects – understanding and kindness, he also accepts that for many his choice is strange. "If you see me naked, then frankly, for a lot of people, I would look a bit odd. I have a flat chest and no penis," he says. Aesthetically and culturally, in a world where we have been raised to see a person as either a man or a woman, "for many people [my body would be] quite confronting and hard to accept".

Ayres is now back in Australia. In practical terms, it would have been difficult to complete his transition in Afghanistan, and he was concerned his changing appearance could attract negative attention at ANIM. He is living in Brisbane, as a man, with Le Brocq. Before he left Afghanistan he gave away any last remnants of feminine clothing he owned. He has decided to concentrate on playing the cello. He's not entirely sure what else he wants to do. Ayres was never a particularly vocal LGBTI advocate when he identified as a lesbian. He thinks that might be because he knew, deep in his heart, he never quite fitted in. Being transgender is different. Earlier this year, when he went to his first support group event in Brisbane, he felt deathly anxious. "It was like meeting my family for the first time," he says. An activist role is one he's nervous about. The only time I ever see Ayres lose his patience is when he delivers what seemed to be a carefully thought-out sentence on transgender rights. When my recorder switches itself off part-way through, he briefly snipes at me. Ayres is aware he is privileged. He can afford a $12,000 double mastectomy and is surrounded by supportive family and friends. He has enough money to not work for a while. "My journey through this has been really easy," he says. "I feel – not exactly guilt – I guess I just wish it was the same for everyone, but I know that it's not." Australians are "bullshit spotters", says Ayres. He has a strong belief that, while there will undoubtedly be trolls, he will be accepted at home. "If you're not being yourself, they know it. If you're just being yourself and you're not harming anyone, I really believe Australians will accept you."

Those who know Ayres well say he seems happier than they can ever recall. "I don't think I will ever leave Emma behind. I'm still her," he says. "For many years, I think I did suffer from a kind of sadness, definitely melancholy, and I feel now I'm finally letting that go." He is trying to not regret his delay in transitioning. "I just marvel at all these young [trans] people nowadays who are so clear about who they are," he says. "I suppose I just did it when I was ready." When he left Kabul the last time, ready to start his life as a man, the airport security guards, after inspecting his viola, asked Ayres to play for them. He obliged with a popular Afghan song, to the delight of the guards, who sang along. "It just felt like such a blessing," says Ayres. "It seemed like it was a sign that, 'It's okay, I can go.' "