At age 20, when reading a Japanese fashion magazine, Dreaming Asa saw a feature about ‘traps’—a boy dressing up like a girl and looking exactly like one, ‘trapping’ one into thinking it’s a female. One year later, he tried it himself and a couple of years after that, began doing it more actively. We reached out to him for a peek at the man behind all that women’s clothing.

“To look good as a woman, it does not just end with having good makeup. Body language, tidiness and fashion play a huge part as well.”

Q: Hi Asa! Thank you for coming on board to share your thoughts with us today! First off, can you introduce yourself? Who are you, where are you from and how did you end up with 8,000 fans on your Facebook page?

A: Nice to meet you too, I am Dreaming Asa from Singapore. My hobbies include cosplaying, gaming and hanging out with friends. I did not expect my Facebook cosplay page to be popular at first but it started to attract more and more people after they found out I’m actually male.

I understand, from your Facebook page, you consider yourself male but cosplay female anime characters and often go out dressed in female get-up too? Can you reveal more about why it is you do that and where you see yourself in terms of gender and sexuality?

I get attracted to female characters from games and animes more often and I felt that I didn’t want to be bound by gender to cosplay who I like. I also dress in female get-up once a while and try to learn more about different kinds of makeup styles while practicing as much as I can. I still see myself as a male though.

When did you first dress up as a female and how did you decide to do so? What did it feel like doing so for the first time and did you go anywhere in that outfit that day?

It was almost 6 years ago, I feared that my parents would be against it so I told my sister in secret about it. I had no idea where to start and she introduced me to friends from the cosplay community who taught me how to do female makeup. It felt really embarrassing because I was afraid it would not look good but they did a good job in teaching me. We did it in a cosplay shop at SCAPE but I didn’t have the courage to go anywhere so I just stayed there the whole day. (laughs)

When did you start wearing women’s clothes on a more regular basis? What, or who, gave you the confidence to keep doing it?

I started to wear [women’s clothes] more often about 3 years ago. After I was done with NS [compulsory National Service], I started working and bought more and more female clothes. My sister managed to persuade my parents that cross-dressing is quite common nowadays and even my mom started to support me. That really boosted my confidence a lot.

How did you learn how to do hair, nails and make-up? And do you have to do anything extra to look good as a woman?

Other than my cosplay friends, my mom and my sis also taught me the tips and tricks of makeup. I also look to famous cosplayers to learn their makeup techniques and find suitable hairstyles. To look good as a woman, it does not just end with having good makeup. Body language, tidiness and fashion play a huge part as well.

Who are you when you’re not Dreaming Asa? Can you tell us or is it a secret?

N/A (Pretty much nothing.)

Does your family know about Dreaming Asa? What about ‘otokonoko’ or ‘trap’ or cosplay culture? How much do they know about those? How did they react when they found out, or how would they react?

Yes, they do and they are not impressed at all. It was thanks to my sister that they know. She managed to explain this subculture to my parents.

How popular is ‘otokonoko’ or ‘trap’ culture in Singapore, you think? Are Singaporeans receptive to seeing otokonokos out on the streets, from your experience?

From what I know, a lot of people who are into or not into cosplay also gave negative views about this trap culture.

What is your day-to-day routine like? How often do you cross-dress or are you mostly dressed as a female these days?

I try to keep my skin hydrated because I have dry skin issues. I usually dress out once every 2 weeks if my skin is doing well.

What about weekends? What do you do then?

I will hang out with my friends or do makeup tests at home.

What advice do you have for men hoping to look like Dreaming Asa and go out on the streets as Dreaming Asa does?

Having perfect makeup will not be enough, they need to learn to be feminine as well. Fashion and hairstyle play an important part too.

Can you map out a suggested action plan for people who want to do the above to follow?

Read up more fashion magazines or check out the internet for fashions that suit your taste.

What key things/people/situations enable you to be Dreaming Asa, in your opinion?

My family who’ve supported and guided me. If not, I would have stayed as a closet cross-dresser.

How did becoming Dreaming Asa change you as a person? Or did it not change you? Why?

It definitely did. I made a lot of new friends and even had supporters from overseas, something I never would have expected to have.

If you could go back and replay your entire life all over again, what would you do differently?

There is nothing I regret because what happened in the past makes me who I am today.

What were you like as a child? What about as a teenager and young adult? How did you change at every decade? Or did you not change?

I used to be a shut-in gamer. Slowly, after I started dressing up, I learned so many different things and became more open to new things.

Which 3 objects/people in your life can you presently not live without and why?

N/A (There is too much for me to name.)

Of all the objects you bought/received for the purpose of cross-dressing, which was most useful? Why?

Contact lens makes a huge difference for me; it’s one thing I cannot do without. It creates attention to the eyes and eye contact makes the most impact during any conversation.

Which person do you wish LUCK-IT would interview for you to learn from? Why?

Elizabeth Seah. She is the owner of Haru House, who brought Japanese culture to Singapore.

[LUCK-IT Update: We have interviewed Elizabeth! Read her interview here.]

What’s the worst advice you’ve been given, or have heard people giving? And what’s the best?

N/A (Even the worst advice could have been the best. It depends on differing situations and how you perceive it.)

Dreaming Asa is presently a transport operator and single, and is convinced most people will not be able to recognise him when he’s out in public. He is busy making props for his next cosplan but will happily answer any questions you may have for him if you ask him through his Facebook page. You may also share your own experience with cross-dressing in the comment box below.

Photographs courtesy and copyright of Dreaming Asa. Interviewer: Sy
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