But when we approached her, the woman, who called herself Jess, insisted that she had just arrived the day before and that she was here to gamble.
Said Jess: "I come here from the Philippines with my friends to go to Marina Bay Sands to play at the casino. After Singapore, we will be going to Thailand, Macau and many other places."
A worried look suddenly crossed her face when a group of about 10 uniformed police officers walked by.
But she loosened up once the men in blue were out of earshot.
Lighting up a cigarette, she tossed back her long hair and purred: "Now, where were we?"
Upon further chatting with her, she eventually leaned in and said that she was available for sexual services at $200 for an hour.
Such transgender sex workers aren't the only ones on the prowl at Clarke Quay.
Last Saturday night, we observed dozens of scantily-clad women - believed to be Filipino and Vietnamese - outside some of the clubs.
We spoke to another girl - she insisted that she was a "real girl" - on Saturday. She whispered to us: "Be careful of the others here. Nearly all are Filipino ladyboys!"
The Vietnamese woman beamed after we bought her a drink and when asked what she was doing in Clarke Quay, she said: "I can make more money at Orchard Towers but I'm afraid to go there. Too many policemen. I can 'hide better' here."
Club owners TNP approached declined to comment on the presence of sex workers in Clarke Quay.
However, employees at Clarke Quay said these prowlers are careful not to draw any unwanted attention on themselves.