First Event 2013, a convention for transgender and gender-variant people, took up ten rooms and three hallways on three floors of the Peabody Marriott hotel, a low-rise in an industrial estate half an hour from Boston. I was there for a day, but the convention stretched over four, with a revue, a fashion show, a pop-up consignment store inside the hotel (‘Tiffany’s Closet: ReBorn to be ReWorn’) and a real wedding on the Saturday. There were workshops led by trans people with stories to tell, advice to give or services to tout, along with trans-friendly psychologists, surgeons, clerics and teachers. At the merchandise fair exhibitors included a voluble, magenta-haired DIY manga artist, a costume jewellery maker and an organiser for the state’s LGBT Democrats. Amanda Simpson, the US government’s first out transgender appointee, gave the keynote address: a former test pilot, Simpson is now Special Assistant to the Assistant Secretary of the Army for Logistics, Acquisition and Technology.

I went to watch and to listen, but also to be seen: I wore a vintage dress with black-on-black pattern, two sparkly bracelets, a knit scarf and a claret lipstick. I went by Stephanie all day. I’ve been dressing up as a woman, or a girl, on select occasions, for almost two decades; I stopped for a while when I was an untenured professor, and when our children were very young, but I missed it more each year. My wife knows all about it, though I don’t dress as a woman when we’re at home; I do wear nail polish, and girly rings or bracelets, and feminine colours (last month she gave me, and I cherish, a spectacular violet coat). I’ve never worn a wig, but now I need one; at 42, I am slowly but obviously going bald.

Transgender, or trans, takes in the narrower categories of transsexuals (like Jan Morris), cross-dressers (like Eddie Izzard, and me), third-gender or genderqueer folks, and people who aren’t sure where they belong, but know that they want to be, or present themselves as, a gender that doesn’t match the body with which they were born. I could live without dressing this way – I did for years – but I could also live without music, or without eating fruit, or without my glasses. I like wearing a dress and tights, and I want to look good in them, and I like being addressed as Stephanie. I do not experience the profound dysphoria, the feeling that I must escape this wrong body or else, that many trans people report; 41 per cent of trans respondents in a 2011 US survey said they had attempted suicide at least once, compared to 1.6 per cent for the population as a whole. Sometimes I say I have mild gender dysphoria: I like my life as Stephen just fine, so long as I get to be Stephanie now and again.

At the merchandise fair, I was shocked to see myself in a hairdresser’s mirror after I tried on a shoulder-length wig: I no longer looked like a pretend girl or a woman, like someone trying earnestly to dress up cute. Instead, I looked like Stephanie for real – but like a helplessly mannish, uncomfortable Stephanie, with a shockingly angular jawline. Later, at Tiffany’s Closet, I found a wig I liked more, and it cost less too: shoulder-length, but less heavy, dyed the blackest black, it framed my face while hiding my jaw. This Stephanie looked a bit Goth, more mannered than the way I would like to see myself; and yet she was me, or she could be, at least for a while. I bought the wig, a velvety top, a plain black skirt, a dark floral skirt and elegant silver-grey shoes that fit perfectly, with one-inch heels. I wore the wig and the shoes for the rest of the day; I found myself chewing on strands of black hair.

At a workshop on makeup, I saw a lot of loud prints, several leopard and tiger patterns, some chunky but feminine boots; I also saw a woman with a black and green colour-block dress and sparkly bracelets, rocking a look like the one that I want for my own. The workshop itself was helpful but intimidating. ‘To be born woman is to know,’ Yeats wrote, ‘Although they do not talk of it at school,/That one must labour to be beautiful’: adults who weren’t born as women have a hard time learning later on. Among the lessons of the session were that girlish looks need more blush, sophisticated adult looks less, though they may need more mascara. I learned that a business card, held against the temple, prevents eyeshadow overshoot. ‘Eyebrows,’ the workshop leader said, ‘are a whole other world.’ Watching her manipulate her brushes, her eyeliner applicator, I remembered how incompetent I have always felt with spatial and physical skills. Being out as a cross-dresser has made me a lot more aware of my physical body, of how I move through air and take up space: I’m less afraid of non-verbal communication than I used to be.

Further lessons were to be had at ‘Successful Shopping for Your Most Feminine Silhouette’, a workshop run by Monica Prata of NouveauShe, a ‘Feminine Image Consultant for those who are transgendered, transitioning or integrating their genders’. She was fascinating on the subject of fabric weights – colour, we were told, wasn’t the only thing that mattered. She explained why we should avoid puffed sleeves and cropped jackets, and go for heavier fabrics or patterns on the lower half of the body, to emphasise hips and make shoulders recede. A-line skirts and dresses work well; asymmetry draws the eye off the shoulders too. A necklace and a neckline should have the same shape – both triangular, or both round. I stood up when Prata sought volunteers for critiques; she praised my bracelets, and the line of my dress, her praise more flattering because she had dissected the outfits of other girls. (When it came to clothes and make-up, we were often called, and we called one another, girls. When the topic was medical, legal or political, adult transwomen were always women, children and teenagers girls.)

It’s a strain to know that you can’t quite look natural, but it’s a worse strain (one I no longer feel) to keep your preferred gender secret: it’s a challenge, as Prata said, to discover what fits, and it’s easier once you accept that the impression of never having to work at it, the look that seems effortless, may not be a look you can achieve. I like my fake breasts, though often I wish I had real ones. I feel more confident, more myself, as well as happier, prettier, less impeded, less awkward, in femme attire; and yet I know it’s an art, or an act. I am not exactly a real girl, and won’t make the sacrifices required to be one.

For young people now those sacrifices may be a little less hard to make – or at least it may be more widely accepted that it’s possible to make them. When I was a child, I wanted to be close to girls, to be more like girls, and didn’t like being a boy, but I had no idea that I could have a choice. At the convention, Susan Maasch, director of the Trans Youth Equality Foundation, talked about how much, and how fast, things have changed: with the right support, some transgirls and transboys can live as they want to as early as grade school, and take hormone blockers to avoid the ‘wrong’ puberty until they are old enough to take hormones for the right one. There is now a clinic at Boston Children’s Hospital that evaluates and treats pubescent children who don’t identify with the body they were born into. One of the children the clinic took on, Nicole Maines, who was born as one half of a pair of identical male twins, gave an inspiring talk alongside her father at an awards dinner in 2011, when she was 14 : ‘I am a transgender girl. I was born a boy but I have always known I was a girl. I changed my name and wore my first dress to school in fifth grade. I was a little worried what my friends would say, but they said it was about time. I was vice-president of my class and happy to be my real self.’ Maasch’s organisation has published an advice pamphlet for trans teens: there are tips for transgirls on selecting the right bra, and information for transboys on binders and packers; everyone wants to know how to come out to friends.

But the convention was for all ages and many types. I saw knots of teenagers, some beautiful, some punk-rock tough. I saw people of retirement age, dressed as if for a cotillion; some women had clearly been men, some years ago, and seemed to dress so as not to stand out now. And then there were people who probably looked like me: somewhere between 35 and 55, trying hard to present ourselves, today or all year, as the gender we prefer. Perhaps a third of the people I saw were dressed as guys, in ties and button-down shirts etc, though of course there was no way to tell some trans people – men and women – from random hotel guests: it’s horribly rude to ask. Events for transmen included a pool party and a lunch with lessons on masculine deportment.

Given all this activity, and the many similar events regularly held in the US, not only on the East Coast but also in Texas and Ohio, it is surprising how surprised people were earlier this year when Suzanne Moore set off firestorms in the British press by lamenting that women like her were ‘angry with ourselves for not being happier, not being loved properly and not having the ideal body shape – that of a Brazilian transsexual’. Trans people of all body shapes, and our allies, turned some of their anger towards Moore, who responded intemperately on Twitter and in the Guardian. Moore and her defenders – Julie Burchill wrote in an article published and then retracted by the Observer that transwomen were just men who wanted to have their ‘cock cut off and then plead special privileges … above natural-born women’ – implied not only that transwomen weren’t women, but that being trans was a frivolous, cosmetic choice.

The best thing that came of the row was the stoutness of some of the ripostes. ‘Once you decide that some people’s lives are not real,’ Roz Kaveney wrote, ‘it becomes OK to abuse them … to shout things in the street, or worse.’ (More gay, lesbian, bisexual and trans people are killed in Brazil than in any other country; a recent survey found that of the 338 LGBT people murdered in 2012, 128 were trans.) ‘Those of us fortunate enough to be born in a body that suits our felt gender identity,’ Laurie Penny wrote, ‘are going to have to accept that being cissexual, just like being heterosexual, isn’t “normal”, merely common … Stubborn gender essentialism – the belief that your body and your hormones should define everything about your life – is what women have been fighting since the first suffragettes unrolled their green and purple sashes.’

There’s a sharp contradiction in such arguments, but that doesn’t mean that they don’t make sense. On the one hand, your body shouldn’t define everything; on the other hand, your body might be important enough for you to have to go to great lengths to change it, or to change how you and others perceive it, at the risk of social death, or actual death. Political arguments about trans people now, like arguments about gay people thirty years ago, often rely on a medical model: a discrete set of people simply can’t help being this way, and so they – we – shouldn’t be punished for it.

But if that’s what it means to be trans, should I call myself trans? What am I doing at the Peabody Marriott, why do I want to come back next year, and what is Eddie Izzard doing in pearls? What do we make of the people – almost all of them younger than I am – who try to live full-time in between genders, to mix and match them every day? What of the ten-year-old quoted by Andrew Solomon in Far from the Tree who says: ‘I know I’m a boy, but I don’t want boy toys. I don’t want boy clothes except to go to school … I’ll probably be a dad who sometimes likes to be a girl and sometimes likes to be a boy’? (He could grow up like me.) Why do I want to feel pretty, to look good in tights and a skirt, when I can tolerate, and enjoy, a life where I usually look like a man? These are questions that can’t be answered by medical models, or by columnists, or by anybody who can’t use a first-person pronoun when talking about experiences of gender. I am a man who can feel like a girl inside, who wants to be seen as a woman from time to time; I’m looking for better answers, and for better shoes, and more places to show them off.

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