© 1999, Associated Newspapers Ltd., London, UK

Ali at seventeen

August 28, 1999

Ali the 6ft schoolgirl
who hides an extraordinary secret

By Sarah Chalmers

AT 6ft 1in with a slim size 12 figure [US size 8], a curtain of chestnut hair and a bedroom filled with fashionable clothes and three vanity cases of cosmetics, 17-year-old Ali Gregory might easily harbour ambitions to be a model.
      Hardly surprisingly, mother Alison is hugely proud of her glamorous child. She is also, it must be said, somewhat concerned. For Ali is not in fact the head-turning young woman one first imagines, but a sixth-form schoolboy. And the ambition which fires his every waking hour is rather more complicated than those which typically consume today's teenagers. Ali wants to be a woman. In truth, he feels he is a woman trapped in a man's body - and such is the strength of his belief, he is undergoing psychiatric assessment which he hopes will see him referred for a sex-change operation. Flicking his hair back over his shoulders Ali - who was christened Alastair but has been known by the shortened Ali since he was 11 - says: 'I've always known I had a female mind in a male body, so there was no great angst about it. I feel I have been trapped inside the wrong body for 17 years.'
      In September last year, shortly after his 16th birthday, Ali confided his feelings to his mother. Alison, an English teacher, remembers: 'I was on my way out to the gym when Ali said he had something to tell me. I was trying to dash off and he just said he wanted to have a sex change operation.
      'I remember thinking, "Goodness, I've got to handle this well." At almost the same time I thought, "Well, I won't be going to the gym, then." After that we sat and talked for about three hours - which is quite rare for teenagers.'
      There weren't, Alison insists, any tears or recriminations. 'It wasn't really a surprise to me because Al had always been different, but I suppose I hoped it might be a sort of Eddie Izzard thing - just about dressing up. I tried to suggest alternatives - I told him he could redefine what masculinity was.
      'My position has always been that people are human beings, and I hate sexual stereotypes. I was always very happy for male children to play with dolls or female children to play with cars. But there's something very conventional about being a mother. You worry all the time, and I suppose you want your children to be "normal".'
      Despite her reservations, Alison says she understood it wasn't just a fad or a ploy for attention. 'It was an identity thing,' she says.
      With her blessing, Ali visited his GP and embarked on the lengthy process which he hopes will one day lead to a sex change. It will cost £5,000 and it is a fee she is willing to pay to ensure her son's happiness. To be deemed a suitable client for surgery he must demonstrate that he has lived as a woman for at least two years.

Sheffield on map of United Kingdom

      The mother could only watch and hope her son was not bullied when, in January, he began dressing as a girl to attend his school, King Edward VII comprehensive in Sheffield, where he is studying for four A-levels, including psychology. All exchanged trousers and shirts for skirts and cropped tops. He bought a bra, which he wears stuffed with cotton wool and began openly wearing make-up. He stopped concealing his nail polish under gloves.
      For his first day as a girl he chose to wear a cerise pink chiffon skirt which his mother describes as 'hideous'.
      'Mothers always disapprove of their children's clothing, so there's nothing unusual there. I think I was more worried about the material -chiffon is far too cold for January. Amazingly, no one seemed to bat an eyelid. I think because Ali presents things as the norm others accept it as such,' explains Alison.
      'Most people just take it in their stride and don't really comment. 'But she admits: 'I still can't say the word "she" when referring to Ali.'
      Born on August 9, 1982, Alastair Joseph Ross Gregory was the second of Alison and George Gregory's sons. Together with his elder brother Jonathon, he was brought up in a rambling, two-storey house in the heart of Sheffield.
      His earliest memory offers an intriguing insight into his early life. 'I remember I desperately wanted to wear a skirt and be like the other little girls. Somehow my mum got me a yellow wrap-around skirt and I loved it. I used to wear it round the house. 'I loved the feel of it and the way it spun round when I walked. But I also remember being told that I couldn't wear it to visit some places,' Ali says.
      His mother, too, recalls those early indications that her son was not a typical little boy. 'When he was at nursery school I was called in by the head teacher and told he was always dressing up in a pink tutu. I was quite incensed that she was implying this was a problem, but when Ali started school he did challenge my principles.
      'I vividly remember taking him to the shops to buy a lunch box. He was adamant that he wanted the pink one, and I kept steering him towards the blue one. He made quite a fuss and insisted that he liked pink. I really didn't have a credible argument, just a strong feeling that pink is for girls.'
      Ali won that particular battle and was determined to forge a female identity at junior and middle school. 'I had to wear trousers but I always made sure they were in bright colours like purple, not grey, and I would never wear denim because I saw that as very boyish.
      'Basically I just tried to do whatever the girls were doing and tried to steer away from what the boys did, so people would take me for what I thought I was.
      At home he was just as determined to make people understand who he was. His favourite toy was a set of plastic characters called Keepers, which were widely perceived as a girls' game.
      'I hated having my hair cut and used to scream and shout when it was all cropped off. For a while I refused to have my hair washed in anything other than Timotei shampoo. I'd seen the advert with the girl who had long, blonde hair and that was what I wanted to look like .
      I watched the film The Little Mermaid and I thought it was wonderful that her tail was turned into legs and she was so happy. I hoped that something like that could happen to me. I used to sing in the church choir and I thought God could make my male body into a female one.'
      Ali is adamant that he was never bullied for his effeminate ways, and only remembers one awkward incident at middle school: 'All my close friends were girls but I remember sometimes hearing them say I couldn't play certain games because they were "girls' games." When that happened, my friend Claire and I would just play the same game a little bit away from the other girls.'
      Ali's mother is convinced it is his confident attitude that deters bullies, and the most striking thing about meeting this teenager is not his gender but his maturity and eloquence
      Chatting animatedly around the kitchen table with his 50-year-old mother, Ali seems composed, intelligent and wise beyond his years.
      Not even his parents' divorce, when he was eight, and his father's subsequent move to the U.S. seem to have fazed him. 'It was a gradual thing. Dad is a driver and used to work in the States during holidays. He spent so much time there that when he moved there permanently there was no great change for us as a family', he says dismissively.
      Of course there have been problems. Secondary school is a mine-field of emotions for most boys, let alone those who are openly girlish. "I used to get depressed when I was about 13 and cry a lot. I didn't realise sex-change operations were possible and felt hopeless at the thought of dying an old man. I thought I would be better off dead than living as a man, because I had no quality of life.'
      At around this time Ali first learned that sex-change surgery was possible and secretly consoled himself that this was the answer to his prayers. There were, however, still many practical problems. 'I began to feel attracted to boys but, of course, I couldn't do anything about it. I just had to bite my tongue and tell myself my time will come. I won't go on a date with a boy until I've had the operation. Of course, female friends would ask me if I was gay, but when I explained I felt like a woman they seemed to understand.'
      With puberty came a growing abhorrence of his body. Ali's voice has broken but he deliberately tries to catch it at the end of sentences to sound more feminine. He loves swimming but has not indulged in his hobby for years because he refuses to wear trunks or go into male changing rooms. At school he tries not to drink during the day so he won't have to use the gents' lavatories.
      Like most teenagers, Al communicated little with his parents. His closest friends are twins Alice and Jenny, and they were the first be told of his hopes for a sex-change. With their help he began learning how to apply make-up and buying girl magazines like Just 17.
      'I wasn't worried about how my parents would react and I knew I'd have to tell them at some point. You have to be at least 18 and have lived as a woman for two years to be eligible, so I decided to tell my mother when I was 16. It was September 4, 1998, a month after my birthday, and my mum was on her way out to the gym when I said,"I have something to tell you."'

Ali with her mother (inset)

      Ali's mannerisms and chatty demeanour are very feminine. In fact, the only time he loses his composure and acts like a surly teenager is when I ask him about shaving.
      In monosyllables, he insists he doesn't shave but plucks the hair from his chin - as he does his eye-brows. And rather than make him appear more masculine, the reply leaves me feeling gauche and insensitive, as if I had asked a young girl about facial hair.
      The operations he faces will be uncomfortable and there is no guarantee of success. Despite this, Al is adamant he has no doubts about his true gender and says he is glad the surgery is irreversible. 'I know there will be lots of problems, but there always have been.'
      Already Ali is being teased by some boys at school who ask him if he fancies them. But these hardships are, he says, more than countered by the number of people who are convinced he is already a girl.
      Bubbling with pride, he recounts a tale about a trip to London where he was prevented from entering the gents' lavatories at St Pancras railway station by a diligent guard who pointed him in the direction of the ladies'.
      Ali buys his clothes at Top Shop and Miss Selfridge and says he has never been challenged about going into the changing rooms.
      He told his father of his plans over the phone and George, who has remarried, was very supportive. He said: 'I wasn't entirely surprised, because Ali has always been an individual and from an early age he liked a lot of privacy, especially about the bathroom.'
      All eventually hopes to have the name on his birth certificate changed to Alicia, and to train as an actress.
      He is well known and accepted locally, but he admits it's nice to go where nobody has any preconceived ideas about him.
      'When I've had the operation and meet new people I won't tell them I was born a boy, because that would be a lie. I was born a girl - I was just given a boy's body.'
      When we met, he had just returned from a concert in another town and said: 'It's nice to be somewhere else and make a fresh start. Whenever people look at me I always think they know.'
      Of course, it could just be that they are looking at a stunning brunette.

About a year after this article was published, Ali featured in a UK national television (Channel Five) documentary. She was still at the same school but was only then starting hormones, as the film showed her response to at last being given "permission" to start them by the panel that control such things at the local gender clinic (The Porterbrook, Sheffield). During the crucial time she had been waiting she had been a private patient of the head of that National Health Service (NHS) clinic, Dr Kevan Wylie, since she was not allowed to attend his NHS clinic until she was eighteen. She then had to be assessed by the various personnel of the clinic (including a clergyman, a style consultant, and the speech therapist) before permission for hormones could be decided at a committee meeting. But from that point Ali will have been receiving hormones on NHS prescription. Less than three years later she would have been eligible for reassignment surgery, paid for by the NHS too.

We hope she is happy.