Inside the broken lives of Orchard Road’s ladyboys

Editor’s note: This is a two-part feature in The New Paper. The second part is below in the same post.

Source: The New Paper
11 June 2007

Inside the broken lives of Orchard Road’s ladyboys
Dad left family because of me
By Mindy Tan

When Selina, 27, begins putting on makeup at home, there are no questions from mum about the outing or trivial chatter about what hairstyle is best.

Selina’s mother can’t bear to look at her own child – the womanly face, arched eyebrows, long lashes and lipstick belong to a side of her child that she doesn’t want to know.

You see, Selina is a transvestite.

Speaking from his three-room HDB flat in Bukit Batok, the sex worker – who goes by the name Selina – said of his mother: ‘She has accepted me, but she doesn’t want to know the other side of me.’

The ‘other side’ can be traced back to the age of 9, when he claimed he was sexually abused.

‘I may be normal today if not for that,’ he said.

Although he dresses like a woman and has breast implants, the 1.8m-tall ladyboy has not had a sex change.

He has been a prostitute for 14 years and is considered a ‘mummy’, or older ‘sister’ in Orchard Towers.

He commands up to $300 for an hour’s services, and sees four clients a night.

But not a day goes by when his heart isn’t heavy.

He is the main breadwinner of his family – his mother, a 23-year-old sister who is a sales assistant, and two other siblings, 18 and 16, who are studying.

His father, he said, divorced his mum because he said he could not live with a transvestite son.

At 10pm, as Selina prepares to leave his flat, the scent of Chanel No 5 is heavy in the air.

Sometimes, his mum looks down at the floor and whispers: ‘I pray for you, make good money.’ Click to see larger image Selina looks her best for an ‘interested’ client. They chat for a while but don’t strike a deal.

But she never looks directly at her son’s face.


Life for Selina has never been easy.

He is constantly reminded of why he has to struggle.

Already an effeminate boy in Primary 3, he was sexually abused by his gay uncle, he said.

When he turned 13, he confided in his family but no one believed him.

The turmoil exploded one day when a boy in school called him ‘Ah gua’ (Hokkien for sissy).

Selina punched the boy, then ran away from home.

The teen ended up in Geylang as a male sex worker, entertaining men.

For the next three years, he stayed in a rented hotel room in Geylang for $20 a night and worked in the red-light district. For his sexual services, he got $80 an hour.

But while the money was good for a teenager, he was confused inside.

He said: ‘I used to look at myself in the mirror and ask, ‘What am I? Am I gay? Am I straight?’

As a young boy, he learnt the ‘skills’ of the trade from female prostitutes.

‘The women on the streets taught me to survive. ‘Get out there and support yourself,’ they said.’

When he was a 16-year-old gangly teen, he met an Australian client.

Selina pointed to a photograph of his chisel-faced ex-boyfriend and said: ‘I lived with him for five years. I didn’t have to work.’

Life seemed rosy. Around that time, Selina started dressing as a woman.

On his 21st birthday in 2001, his boyfriend gave him a present by paying for his breast implant surgery in Bangkok.

But the relationship didn’t last.

Selina said: ‘I realised the relationship wasn’t what I wanted, I wanted to be free.’

He packed up and left the boyfriend’s house.

He also paid $2,000 from his own savings to remove the implants.

‘I wanted to return everything my boyfriend had given me, including the breasts. The relationship was over.’

Selina lifted his top to show the surgical incisions – two 10cm-long keloids on his chest.

He returned to work in Geylang for a few months so he could afford new silicone breasts.

When he moved to Desker Road to work for a few days, he met a ‘sister’ who took him to Orchard Towers.

In a few weeks, Selina earned enough for a $1,800 breast implant procedure.

Selina admitted that most of what you see of him is fake.

‘Even the hair extensions,’ he said.


The truth lies in his broken and taped together identity card.

Showing the battered card to The New Paper on Sunday, he pointed to the boyish-looking photo and said: ‘That was me.’

He recalled that in Secondary 1, he was a striker in his school soccer team.

His passport states ‘M’ (for male), but it bears an updated photo of a woman.

So far, he has had three nose jobs, two chin jobs, collagen cheek injections, and an operation to raise his forehead.

Once every two weeks, he gets an $18 dose of female hormones in an injection from a doctor. Or he takes hormone tablets (at $100 for a year’s supply).

Last month, he flew to Bangkok to extract his teeth and replaced them with fake porcelain ones.

He said: ‘I pulled out eight (teeth) above and eight below.

‘It’s painful but nothing compared to the emotional suffering we transvestites go through. We are actresses, darling.’

Last week, he made another trip to Bangkok for a third silicone hip injection to make his figure ‘as curvaceous as possible’, upping the total cost of his beauty procedures since 2002 to $12,500, not including airfares.


Selina turned to prostitution because other jobs were ‘not viable’.

‘I have tried many other jobs,’ he said.

He has worked as a clothing salesgirl, a barmaid, and also as a performer at the comedy club Boom Boom Room.

Selina has even done catwalks and modelled for print-ads as a woman.

He says he has no problem wearing skin-tight clothes at fashion shows.

‘During clothing changes, some models who have never seen my body were shocked. They stared. But I’m not shy about it.’

There was no getting away from the judgement of others.

‘What was the first thing on your mind when you first met me?’ he asked. ‘What does the public see? We just have to deal with it.’

Throughout the two days we spent together, Selina constantly said: ‘Ask me anything, darling, don’t be afraid. I get kinky questions all the time.

‘People should understand who we are, and why.’

Selina is the oldest ‘sister’ in Orchard Towers, according to eight other transvestites.

Selina said the older ones had gone abroad or found boyfriends.

Playing the role of a ‘mummy’, Selina is strict about their turf during work hours, from 11pm till 3am.

He is quick to spot a strange face.

If an ‘alien’ lingers in the area, Selina throws an intimidating stare.

Most of them usually leave, he said.

Singaporean ‘sisters’ who wish to work in Orchard Towers need Selina’s permission to do so.

He is selective – only well-mannered ones are allowed.

Thai ladyboys acknowledge Selina by putting their hands together and bowing slightly when they see him. But they do not need her permission to work there.


The money Selina makes goes to the family – the real family away from the streets.

At home, Selina does not wear makeup, but still dresses like a woman and his hair extensions remain.

‘When I put on makeup for work, I become a different person,’ he said.

He becomes flirtatious and more vivacious.

With his mum, he is the ‘quiet daughter’.

He said: ‘When I see my mother’s face, I am happy.’

But there is guilt as well – his parents’ marriage was wrecked because his father could not accept what his eldest son had become.

‘I really miss him,’ Selina said.

‘I would talk to him if there was only a chance.’

He wants to move to a bigger apartment, but his mother does not.

And he won’t leave her because he feels it was his fault that her marriage broke down.

Selina said she and her 18-year-old brother don’t talk.

‘The only thing I tell him is that I didn’t choose to be born like this. It’s not my hobby.’

Selina said ‘the whole block knows’ about him as his neighbours have seen his transformation since he was a boy.

He said a full sex-change operation isn’t in the works. He is contented with being both father and ‘sister’ to his siblings.

‘If I tried to change that, I would lose myself. And I guess even with a full operation, people will still call me ‘ah gua’.’

He added: ‘Maybe I don’t feel so proud of my job, and my loneliness… But I have come so far, and I have to hold my head up. It’s common sense. Nobody wants to be like this.’

* * *

Source: The New Paper
12 June 2007

‘Sisters’ mark their turf
In our second part on ladyboys, transvestites talk about rules that come with the territory…
By Mindy Tan

THEY start work at 11pm, and they go by a simple rule: Keep away from my turf.

The unspoken rule – which they enforce among themselves – applies in Orchard Towers and the streets along Geylang, Changi Point and Desker Road.

Some transvestites have also been spotted in Clarke Quay.

Veteran sex worker Selina, 27, said the ladyboys must learn to respect the ranks.

He is a senior ‘sister’ at Orchard Towers and gets to decide who works in his ‘territory’.


‘We’re all here to earn money under the same conditions. If you want to be stuck-up, you might as well be a superstar,’ he said.

A ladyboy needs the ‘blessing’ of a senior ‘sister’ to work in the district. He said that most of them stick to their territories.

When Selina sees a ladyboy who does not belong on his turf, he springs into action. If he asks the newcomer to leave, he’d better leave, he said.

What happens if the rules are broken? Things may turn nasty and the intruder’s name in the small transvestite community may be ruined.

The New Paper spent two days speaking to nine Singaporean transvestites here.

They said that there are an estimated 100 Singaporean transvestite prostitutes here.

Those from Thailand, Malaysia and the Philippines number another 100 in all.

It’s a small community and everybody knows each other.

For example, a ladyboy from Changi may go shopping with another from Orchard Towers during the day, but come 11pm, friendship is put aside.


Turf rules were passed down from the Bugis Street era of the 1950s, they said.

Liz, 32, a Singaporean transvestite who has been in the line for 12 years, and has access to all ‘territories’, said: ‘Nobody will stop you if you walk near Orchard Towers before 11pm. But after that, you better disappear. If you must walk past, pay your respects to the sisters there.’

Every transvestite is accorded certain rights to enter certain areas, which are ‘ranked according to market rates’.

Those who work in Orchard Towers comand the best rates. The ‘senior’ sisters are there, charging $250 to $300 for an hour’s service.

And the longer you work as a ladyboy, the more senior you are.

Geylang is ranked second because those working there earn $50 to $80 an hour – and the rate has not gone up in 13 years, according to Selina.

Those working at Changi Point are paid $30 to $50 an hour, while those at Desker Road get $20 to $50.

The senior sisters at each location decide if a newcomer can work there.

Liz said that in Orchard, the ladyboys’ dress sense is ‘classy’.

They carry Chanel handbags and wear branded clothes.

In Changi, ‘it’s revealing’, and at Desker Road, you don’t have to ‘dress to kill’.

As a ladyboy ages, he is considered to be more beautiful.

The reason? More years at work means more money for more surgical procedures like facial reconstruction.


It would mean entry into a turf higher up in the hierarchy.

The ‘promotion’ is usually granted with the ‘blessing’ and recommendation of a senior sister.

Selina said of the conditions in Orchard Towers: ‘If an older sister decides to introduce a ladyboy to the turf, the other sisters all have to agree. One phone call and that’s it. There is usually no conflict.’

But Wanda, who was introduced to Orchard Towers by a sister, said he was bullied when he started work there in 1997, and later, again in 2004.

Wanda said: ‘They slapped me, they extorted money. It’s very common.’

This can happen in front of clients, usually due to jealousy because newcomers get clients easily.

In Orchard Towers, foreign sex workers operate in different sections. A club on the third floor is only for Thai ladyboys.


And different clubs are patronised by different nationalities.

Singaporean ladyboys – experienced or not – are always top in the hierarchy.

They have ‘home advantage’ and can work anywhere in the building, and in any club within their own turf, whether it is Orchard Towers, in Geylang, Changi Point or Desker Road.

The clients, especially at Orchard Towers, can be very specific when it comes to what they want – a transvestite with breast implants, a transsexual (who has undergone a full sex-change operation) or a woman.

Selina said: ‘Some regulars have families. Some are very discreet. But there are also those who don’t mind being spotted in the area.’

The unspoken understanding is that the minute you become a transsexual, you will earn less.

Those who have breast implants and have their penis intact earn more.

Daniel, a cross-dresser, explained: ‘Some men, they want ‘everything’ in a sex partner.’

Nadia, 22, a Singaporean transsexual who has undergone a full sex-change operation, learnt this the hard way. She found this out only post-operation.

If a woman is what a man wants, he ‘would rather go for a real woman,’ she said.


1 Response to “Inside the broken lives of Orchard Road’s ladyboys”

  1. 1 sirmarjalot 8 December 2010 at 5:36 am

    Very interesting to see inside how it operates. I remember being in that bar on the 3rd floor of Orchard towers and guy in another bar took me there, he preferred ladyboys, later I quietly slipped away. i wonder if its abuse as childhood that is the cause for alot of them? some way of coping with the damage done in those tender years. people laugh at them but underneath something very sad has happened.

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