I was a happy little boy. I played with cars and computer games. I had a tree house — albeit a very tidy one. Then puberty kicked in and I thought: “Hang on, my sister is developing breasts and hips. Why aren’t I?” As my face started to change and I got hairy, I was horrified and desperately ashamed. I thought I was some kind of freak.

One of my guiltiest secrets was trying on my sister’s clothes, but it just made me feel worse, because when I looked in the mirror a boy’s face stared back. I thought there was no hope for me.

I grew up thinking that transsexuals were slightly gross: I didn’t want to be someone who looked like a man in a dress; being a target for ridicule would have just added to the pain. When I saw a transsexual in the street — 6ft 2in with a huge man’s face — the distress I felt was indescribable. I didn’t realise that the trans women you don’t see are those who have had successful surgery and have vanished into society.

A friend’s mum told my mum she thought I might be gay. I wasn’t: my first girlfriend became my wife and I loved her deeply. It was a meeting of minds that transcended gender. I played the role — the good son, the good husband — because I thought there was no choice. I balled the pain up inside myself and closed down emotionally. I never drank alcohol, because I knew if I had a couple of drinks, someone more feminine, more animated, would emerge.

A couple of years into my marriage I started playing online computer games with a female identity. “Kate” was born online, and being Kate quickly became all-consuming. Because I hated myself, I could never believe my wife loved me and I was horrendous to her. I spent all my free time in chatrooms, being the girl I’d always been inside. I tried counselling, hoping there would be some way to fix me, lock Kate away, but it just opened a floodgate of feelings I couldn’t contain. It tore my wife apart and I still feel terrible about that. One night, in despair, I took off my seat belt and drove home from work at 100mph looking for a big tree. It was: “Either I live as a woman or I’m going to die.”

The next day my GP put me on Prozac, which saved my life. It gave me the clarity to start researching gender reassignment, and I found out about facial feminisation surgery. There was a website full of women who’d been men, now looking like women, and suddenly I realised that my dream was possible. Within weeks I’d seen a private specialist and started taking female hormones. I became progressively more androgynous. The most terrifying day of my life was Boxing Day, 2006, when I walked down the street in a skirt for the first time. I was fortunate that I could afford to have my surgery privately. I went to the best surgeons on the planet and the bill, including facial surgery and a boob job, was around £50,000. I had my genital surgery in Thailand. It was horrifically painful, and it went on being painful for months. The surgeon used penile material to create the labia and the scrotum to create the vagina. An unexpected bonus is that everything works, because all the nerves are still in the right places. There is something deeply affirming and fulfilling about sex as a woman, and it’s very, very powerful. Having been on both sides, I now know that women have the better deal.

When I decided to “transition”, I steeled myself for the worst. I was prepared to be an outcast and never be with anyone, but I’ve surpassed my wildest dreams. Not only do I have a lovely boyfriend, but I’ve realised my full potential at work, and my business has taken off. I don’t need to tell everyone I meet about my past, and because of how I look, people don’t guess. There are so few women in IT and a huge gender pay gap — there’s this perception that women don’t do technology, and it’s a mindset I want to change. I’m much more effective as a woman because I communicate more. Fundamentally I’m still the same person, but it’s as if the brakes are off. I allow myself to be much more sensitive to others’ needs.

To begin with, my mother was horrified. We have a great mother-daughter relationship now, but at the same time she has lost her son. It’s been hardest on my brother. He had no idea how to relate to me, but he has four kids who have totally embraced me. I’ll never have my own children and being involved in their lives is really important to me.

I don’t fear being outed. In fact, I welcome it. When I was a little boy there were no role models. If there’d been someone out there like me, who was accepted and succeeding in society, I might have been able to go to Mum and say: “There’s something we need to talk about.” I could have saved myself and everyone around me so much pain.

The Gender Identity Research and Education Society is at www.gires.org.uk

Interview by Caroline Scott. Main portrait by Emma Blau

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