One Night in Singapore: An Encounter with the Ladyboys of Southeast Asia

One Night in Singapore: An Encounter with the Ladyboys of Southeast Asia

I had been searching for the cheapest flight and, by golly, I had found it. I was in Brisbane, Australia at the time and was researching flights to Hong Kong. My friend Emily had arranged for me to relocate to Xi'an, China to teach English to kids! I was excited, but funds were not a-plenty.

There's a new budget Asian airline called Scoot, and they were offering a stellar price between Sydney and Singapore. The final price of my flights was about $200AUD less than the standard itinerary, but there was one stipulation: a 20 hour layover in Changi Airport, Singapore.

Inside Changi Airport

Changi Airport

I didn't know much about Changi, so I did my research. This airport is stuffed with movie theaters, bars with live music, restaurants, free internet terminals, high end shopping, gaming venues, sleeper rooms, showers, the lot! If there's one airport to spend the night in, this is definitely it.

I booked my tickets, and was almost more excited to sleep over in Changi than I was to go to China!

Visions of beautiful women in the same situation as me danced in my head. I mean, isn't everybody looking for a bit of fun in an airport? I would go to the cinema, take naps, check my Twitter account, drink beer and flirt with girls. This was quickly shaping up to be the best overnight in an airport. Ever.

Changi Airport

All of a sudden, I had arrived in Singapore. Still delirious from my flight, I walk off the plane and straight through customs.

What I didn't realize, though, is that you can't actually clear customs twice in the same day! I wouldn't be able to re-enter the terminal until the next day.

I had considered staying in a hotel overnight but decided it wouldn't be necessary. There were napping sanctuaries in the airport! But those sanctuaries were only inside the terminal. I should have stayed in the terminal and avoided customs. Instead, I walked through, claimed my bag, and was essentially left in Singapore with nowhere to go and nothing to do!

“Screw it.” I said. “I'm going out!”

I dragged my bag into the bathroom, quickly changed clothes, sprayed Bleu de Chanel and put my contact lenses in. I stored my bags and hit the metro–Clarke Quay or bust.

Clarke Quay, Party CentralClarke Quay, Singapore

Clarke Quay is the party central of Singapore. Blocks upon blocks are overcrowded with overpriced bars.

And prostitutes, apparently. And, apparently, ladyboy prostitutes.

For those unfamiliar with the ladyboys of Southeast Asia, these men dress as women and, far more often than not, pull if off remarkably well. Many have had their Adam's Apple removed (among other appendages). Their slender physique resembles that of a woman very, very closely.

And frankly, some of them look downright hot.

Not in a gay way, or even a weird way. Ask anybody who's encountered them–they'll tell you the same thing.

Photo credit: Flickr

I stepped foot in Clarke Quay and began to wander. Instantaneously, one of these men of the night accosted me! She grabbed my arm, and pulled me to her. I smiled, said hello, and backed away. I was stunned.

I found a bar that looked inviting and I sat in the smoking area outside. I figured I could bum a smoke off somebody and I'd make a friend for the night. This gentleman was a middle-aged, Aussie-bred Londoner with a bit of a tick.

As I sat there, ladies and ladyboys alike were signaling to me from a distance. They gave the thumbs up, the A-OK symbol, they winked and they “come hithered.”

One came inside the bar and asked if she could sit on my lap. A polite “no, thank you” prompted a request for me to sit on hers. Again, a “no, thank you” was in order. She asked if I would buy her a drink. At $16 per pint, there was no way that was going to happen. She finally got the hint and stormed off.

I think my Aussie counterpart was a bit jealous.

Photo credit: Flickr

Two beers and an entree later, I bid my new friend farewell, took a taxi back to the airport, and found myself a nice bench in Starbucks to sleep for the night.

It wasn't the most comfortable place I've ever slept, but it's one night I definitely won't forget.

And the lesson I've learned? Ladyboys love me. Aren't I lucky?

READ NEXT: Why Bangkok Isn’t Good for Anything Other Than Drinking and Having Sex

21 Responses to One Night in Singapore: An Encounter with the Ladyboys of Southeast Asia

  1. jill December 5, 2012 at 9:00 am #

    And we were in Thailand, we always spotted the ladyboys because they were the best looking ones in the crowd 🙂

    • Jeremy Foster December 10, 2012 at 1:36 am #

      You’re not even joking. I have to be careful.

  2. Ed Rex December 10, 2012 at 6:54 am #

    That doesn’t surprise me that you went to party with ladyboys.

    • Jeremy Foster December 15, 2012 at 2:53 pm #

      Well it’s not like I went out looking for them, Ed! But you can dream.

  3. Derek Freal December 12, 2012 at 3:31 pm #

    Hahaha something tells me that you and I would make great traveling buddies. We’re going to have to cross paths one of these days Jeremy..

    • Jeremy Foster December 15, 2012 at 2:56 pm #

      Haha I had the same thought when I first came across your blog! One of these days…

  4. Tom @ Waegook Tom December 13, 2012 at 12:10 pm #

    Hahaha! I’m surprised you didn’t adopt the “every hole’s a goal” mantra and go there. After all, men are, erm, tighter than women in certain areas…I hope one day that you’ll get so drunk that you fall for a ladyboy. And be the bottom.

    The Hangover 2, anyone?

  5. Scarlett December 13, 2012 at 6:02 pm #

    Haha!! Being able to pick up ladyboys is a definite talent x

    • Jeremy Foster December 15, 2012 at 3:01 pm #

      And, luckily for me, I posses that talent. Yay…

  6. Amanda December 15, 2012 at 3:09 pm #

    Bahaha, a ladyboy magnet, eh?

  7. One February 28, 2013 at 12:03 pm #

    Alright. It’s time to get this right, as i see how wrong people are about this all over the net and offline.

    Ok. These so called ladyboys (derogatory term) are transexuals. The feel like women, and have therefore taken hormones and done surgery to fully become a woman. It’s not a fun costume or temporary thing for them. They are mentally women, born in a male body, but not feeling like a man, they are really not men, and that is how it is. A lot of transexuals actually commit suicide around the world, because it’s obviously not an easy thing to be a transexual. So, they don’t dress up as women, yes, even with a dick, they are not men.

    It’s sad that they have to be prostitutes to survive.

    • Jeremy Foster March 3, 2013 at 12:11 am #

      Thanks for clocking in. I really do appreciate it.

      I do understand where these girls come from–I had quite a liberal upbringing and I am very familiar with their struggles. I did not mean to belittle anyone, and I hope I haven’t. I only wanted to highlight my rather shocking and unexpected experience in an area which seemed to swarm with ladyboys.

      I know it is not the case that all transsexuals must be prostitutes to survive. Keeping away from that topic, I will only say that these people are prostitutes just like anybody else is. Becoming a prostitute is not a condition of being a transsexual.

  8. Hannah March 13, 2015 at 6:56 pm #

    I want to say womanizer but I think that doesn’t quite fit…ladyboyizer? haha. Funny story for sure!

  9. KEN HUFFF October 31, 2016 at 4:23 pm #



  10. guy October 2, 2017 at 11:39 am #

    funny post, surprisingly a lot of mongering nightlife in this country and plenty of trans around

  11. adam March 2, 2018 at 10:17 pm #

    You are right! Some of them do look very hot!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.