I'm a man and I enjoy cross-dressing

For many, clothing primarily serves practical purposes like providing warmth and covering the body. However, for an increasing number of people, clothing becomes a medium for self-expression and exploration. Cross-dressing – wearing clothing traditionally associated with the opposite sex – has a rich and complex history. Studies indicate that cross-dressing can be motivated by various factors; some individuals find it enhances their creativity and self-confidence, while others experience personal fulfilment through expressing diverse identities.

In Singapore, cross-dressing is still considered taboo. Although there is no official data on the number of cross-dressers in the country, online communities like the cross-dressing subreddit suggest that interest is growing. We spoke with *Billy, who discovers joy and self-identity through cross-dressing in Singapore. Below, he shares insights into his experiences, motivations, and the impact of cross-dressing on his life.

This piece was edited for length and clarity.

How did you get started cross-dressing?

I began around 13 or 14, not sure what drove me other than curiosity. I found the gender-based clothing rules strange and started "borrowing" clothes in secret. It's funny, I remember actively refusing to wear girls' tights for a school performance, so not sure what changed my mind!

Was there anything in your childhood that could have influenced this curiosity?

There was nothing toxic, but my dad’s traditional views on gender roles likely played a part. It became a subtle form of protest against that control.

What role did your dad play in asserting gender roles?

I engaged in typical boy activities like sports, which I enjoyed. However, I later realised that dressing as female and doing traditionally male activities weren’t mutually exclusive. Many cross-dressers identify as straight cis men and are happily married with kids. I feel we are lucky to be able to enjoy a wide range of perceptions and experiences being in the community.

What are your pronouns?

I’m flexible about pronouns. When dressed, I prefer she/her, but I don’t mind if others use different terms. When I present as female, I feel comfortable in romantic situations with men but am also attracted to women and femininity from other dressers. I think it’s just about a connection with a person rather than a gender.

Does anyone in your family know about your cross-dressing?

Only my mum knows. I told her recently, which has strengthened our relationship, which I’m very grateful for, as I’m sure not everyone has had the same experience. She’s supportive, although she jokes that I look like my sister when I dress! She has only seen my alter ego in photos. She worries a lot about Singapore and the attitudes here.

Are you in a relationship, and does your partner know?

I am currently dating a cis woman, who is supportive. I told her on our second date, which was difficult but crucial. I hid it in past relationships, and when it comes out eventually, even if they accept that side of you, there is hurt that you have hidden something from them. I think it’s important in a relationship to truly be yourself, otherwise, you’re not giving your complete self to someone and in the long run, it hurts both people.

How did your partner react?

She was surprised but non-judgmental. She took the initiative to research and discuss it with me, which helped reassure her. There were some questions about sexuality, and I think that is understandable. We enjoy a strong relationship; I think she appreciates having a boyfriend who offers fashion advice and shares makeup tips!

What spurred you to share your journey on social media?

I initially found some dressers on Instagram first but I kept my account private. A friend suggested I check out Reddit, where I started posting about wigs and makeup. The positive feedback was overwhelming, and my first post remains the most upvoted. As I grew more comfortable going out, it’s become less appealing to just dress up at home and post online. My need for online validation has decreased.

How has meeting others in the community affected you?

Connecting with others has made me feel more comfortable going out in Singapore. After finding another dresser in Singapore online, we arranged to meet. I was nervous initially, but there was a big group of other dressers out too, and it definitely felt like safety in numbers! As a group, they are super supportive and caring.

Do others worry about revealing their identities?

Yes, it's a mixed bag. Some dress only at home, while others are more open. Fear of judgment from work or family often leads to hiding. It’s unfortunate, but I understand their concerns. Some members of the community only go out in guy mode to avoid recognition.

Are you worried about your own safety?

To some extent, yes. However, I remind myself that I’m not doing anything wrong or illegal. I still post carefully curated content online to maintain privacy.

What precautions do you take regarding personal information?

I typically don’t share identifiable details like my workplace or real name. It’s funny sometimes you might PayNow for the bill and reveal a number or something, but others are quite careful. While I cherish the friendships I've made, I prefer keeping my femme identity in our interaction. Feels like a girls' night out and heightens the feeling of being female!

Do you keep your femme identity separate from your daily life?

Kind of. I’ve started painting my nails in guy mode, though I choose darker colours that feel more masculine. I’ve also begun shopping for clothes in public, which was nerve-wracking, but no one seems to care.

Are your friends supportive?

I’m open with a few friends, but discussions can feel awkward. Even when they accept me, they often don’t show much interest, perhaps out of respect for my privacy.

Do you think others in the community have it harder?

Yes, for sure, some face cultural or religious pressures that make it risky to come out. I’ve read heartbreaking stories of ex-wives ex-spouses exposing someone’s identity, reinforcing harmful stereotypes.

Has anything like that happened to you?

Yes, after a breakup, my ex told my friends about my cross-dressing without giving me a chance to explain. I was fortunate that they were supportive.

How long did it take for you to shop outside?

I haven’t shopped in femme mode yet, but I think my first step will be shopping with a female friend, which provides an excuse to explore the women’s section. If I go alone, I think most people just assume I am buying for someone else. No one has ever questioned me so far. When I went wig shopping recently, I enjoyed the humorous moment of clarifying to the saleswoman that the wig was for me, not my partner!

Have you developed a personal sense of style?

I feel like I have two styles. I sometimes cringe at outfits I tried, as it feels like a condensed version of a teenager’s exploration. I only started wearing wigs and makeup in 2019, so I lacked a wardrobe before that. My home outfits are often too impractical for going out in Singapore’s climate. I aim to dress age-appropriately and maintain a classy look.

How often do you go out dressed, and what was your first experience like?

I go out about once a month. If it weren’t so much effort, I’d do it more often. My first outing was in 2020; I was nervous and didn’t feel confident about my look then.

What was the experience like?

I was with an ex-partner who encouraged me. We chose an LGBT bar, which felt safe, and that’s crucial in Singapore. I’ve also visited non-LGBT bars, where I felt more anxious about being judged.

Have you any challenging experiences while out in Singapore?

Yes, once while dressed, a man followed me home. In guy mode, I would have felt more secure, but in that moment, I felt vulnerable. He ended up touching me. Fortunately, a friend intervened before things escalated. This incident made me realise how uncomfortable I would feel approaching the police, fearing judgment for my situation.

Do you usually go out alone or with friends?

I always go with friends, at least one other person. Initially, there’s a thrill, but it soon becomes natural. I feel more confident and social, and it’s simply about enjoying time together.

What are your hopes for the future regarding cross-dressing?

I want to dress more often. I’ve considered transitioning, but I’m content with my current balance. I think about how a cooler climate might encourage more daytime outings, like in Australia or Europe. I do want a family, though, and I would have to balance that with this hobby.

(*Name has been changed on request)