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My wife Julia* and I met when we were 16. We clicked instantly and could talk about almost everything, and she soon became my best friend. We remained close, but just before we started university, she revealed that she was in love with me, and asked if I would be her boyfriend. I didn’t know what to do, and couldn’t sleep for three nights.

I was afraid that if we didn’t work out as a couple, I would lose my best friend. Eventually, I agreed to the relationship.

Then, in our second month together, I confessed that I liked wearing girls’ clothes.

One of my earliest memories is watching my mother getting ready to go out. She often wore beautiful silk cheongsams and I remember thinking that I would love to touch and wear them. I felt weird having such feelings.

As I grew older, Mum started suspecting that I was different. I would wear knee-high stockings under my school uniform, and would dig through her wardrobe to try on her clothes. She would confront me when her skirts went missing, telling me she didn’t want me to be gay.


I tried to convince her that I wasn’t – I simply liked wearing girls’ clothes. I remember wishing I were a girl, so that I could wear her clothes without anyone questioning me.

When I was 11, I had a penile infection and had to be hospitalised. It hurt like hell and it was very uncomfortable to wear shorts. So Mum lent me her chiffon skirt to wear in the hospital and at home. I felt shy wearing it – but I was secretly very happy.

I had a lot of pent-up frustration when I was growing up because I was confused as to why I was so different from other boys. I felt like the gender of my brain did not match my body.

Mum sent me for therapy, and the psychiatrist said I had bottled all my stress inside, and I would eventually explode. He also thought that my penchant for girls’ clothing
was just a phase. No one considered that I might be transgender. I didn’t have many friends. The boys bullied me because I behaved differently from them, so I mostly hung out with the girls. Ah lians, for some reason, intrigued me with their tight clothes and heavy makeup, but they were never interested in me.

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In Secondary 1, I started asking girls out, but no one ever said yes. I had my first relationship with a girl when I was 15, but it was very innocent – we hung out in a group or studied together. All this time, even though I was hiding a secret desire to dress and behave like a girl, I knew that I definitely wasn’t gay.

Julia wasn’t too shocked when I told her I liked wearing girls’ clothes and I’m not sure why.

Perhaps she had picked up a vibe because I always enjoyed picking out clothes for her.

At that time, I had not fully come out as transgender, but I would get her to wear clothes like tartan skirts, stockings and boots, which I personally wanted to wear. She only obliged on my birthday or special occasions, and even then, would complain it wasn’t her style and that she felt uncomfortable.

I started to embrace my other side when I was an undergraduate in the US. Through online groups, I made friends with other transgenders, and when we hung out, I would feel extremely happy and free wearing women’s clothes.

For the first time in my life, I felt normal and not like an outcast. Julia, who was then my fiancee, remained in Singapore and didn’t know what I was doing.

When I returned to Singapore after graduation, I had to repress my feminine side all over again. Julia was still the only person who knew my secret. I’ve never come right out to tell our families that I’m transgender but I believe everyone knows. My transgenderism is like the elephant in the room that nobody talks about.

I think Julia’s parents, who’ve known me since I was in my teens, are more accepting of me than my own family, who are very traditional. But even then, when Julia and I were engaged, my mother-in-law took Julia aside to ask her why I was so girlish. Julia, who is quite blase, brushed aside her mother’s comments.

But I can see why my mum-in-law questioned her daughter. My hair was long and I was starting to be more open about my dressing.

I’m also quite domesticated, doing the cooking and cleaning, which makes me seem even more feminine. My wife and I complement each other because she’s more masculine in her mannerisms and thoughts.

I’m told that I can pass off as a trendy artist or designer with my gender-neutral clothes like polo tees, frilly shirts or leggings, which I wear on most days.

I only wear skirts, dresses, heels and nail polish when I’m going out with my friends from the transgender community. I don’t dress up at home in front of my wife; I’ll meet my friends at a hotel, and we’ll dress up together. I’ll put on prosthetic breasts under my dresses, but my dresses are not tight because I’ve never wanted to draw attention to myself.


Some transvestites or drag queens dress in loud and over-the-top attire to attract attention, but I’m not like that. I used to wonder if I was a transvestite, but after many years of self-discovery, I’ve come to realise that transvestites are just men who enjoy dressing up as women, but they don’t necessarily feel that they’re in the wrong body or feel a desire to go for a sex change. For me, I just want to fit in, like a normal woman. I’ve told Julia that if it weren’t for her, I probably would have gone all the way and had a sex change operation. She knows that when I’m stressed, I fantasise about running away to Thailand where I can completely be myself without anyone judging me. I think these thoughts scare her and feed her insecurities, and over the years, she has mentally prepared herself that I might really leave. But running away to Thailand is just a fantasy.

What I really hope for is to move with her and our children to the US, and start life anew.

I’ve suggested that Julia and I go for counselling to help us deal with our unusual situation, but she has refused. She is very independent and doesn’t like to ask others for help. Her way of dealing with things is to sweep everything under the carpet and pretend the problems are not there. She’s not very chummy with other people, so I think that helps her deflect unwanted questions from friends and colleagues. Even if people ask about me, she will give them noncommittal answers.

Julia and I used to have quite an enjoyable sex life – I don’t cross dress in bed – but as with most married couples, the frequency has dwindled since our second child was born. We usually only have sex when on holiday; at home, Julia is too distracted by work and caring for our children. I’m very aggressive in bed, and I’ve been told that it’s quite common among transgenders, because of all the repressed feelings and pent-up frustration inside us.

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Although my wife has accepted that I’m transgender, I think it’s more tolerance than 100 per cent acceptance. She doesn’t like to see me in my full gear, with heels and makeup, and I have to keep my girlie clothes in a separate bedroom.

If I forget and leave accessories or lipsticks around, she’ll tell me off,

“Can you not let me see that?” I’ll apologise and we’ll pretend it never happened.

I wish my wife could be mor accepting and wholly embrace who I am, but I think this is as good as it gets. I think she’s also dealing with her own conflicting feelings.

She loves me but this is a semitaboo topic for her. She doesn’t like me to talk about my own transgenderism, but from time to time, we talk about my transgender friends’ relationships and who is going for a sex change operation.

Although Julia has never asked me to change or behave any differently, I know she has the power to take it all away and demand that I completely repress my feminine urges, so I play along and let her deal with it in her own way. If she doesn’t want me to dress in women’s clothing openly in front of her, I can respect that.

My children are still very young, so I don’t think they notice anything different or unusual about the way their dad dresses. If they or their friends ask me about it in future, I will explain to them that my body and my brain don’t agree, and it’s not something I chose.

I’ll explain to them that I dress the way I do to make my brain and body match. I don’t think transgenderism is hereditary. I haven’t thought about whether other parents might stop their kids from being friends with mine – I’ll cross that bridge when I come to it.

As a dad, I’m very hands-on; I feed, clean, dress and toilet-train my children. Even though my wife is the no-nonsense type, she is soft-hearted when it comes to the kids whereas

I’m the disciplinarian. I was never close to my dad when I was growing up, so I don’t think I conform to the stereotypical father role.

I have no regrets about having children or marrying Julia. I used to feel very lost and confused, and my emotions were all over the place. Even though I’m now at peace with who I am, I’m still a highly emotional person, and Julia does a very good job of handling me and my emotions. We understand each other inside out, and know when to give each other space. After all these years, my wife is still my best friend.

Text: Vanessa Tai/Simply Her