After robbing the woman in her flat, he made her strip before sexually assaulting her for an hour.
Raymond Lee Ling Soon also made his victim squat naked at the door and threatened to kick her private parts if she called the cops.
The facilities maintenance supervisor then made off with $400 cash, but did not get far as officers arrested him that day.
Yesterday, Lee, now 39, was jailed 11 years and ordered to be given 24 strokes of the cane for robbery and sexual assault.
His offences were described as heinous by District Judge Low Wee Ping, who also called the accused cruel and depraved.
Court papers said the victim, who cannot be named due to a gag order, had been working as a freelance masseuse out of her rented flat in Chinatown since December 2015.
She was assisted by a friend, who ran online advertisements for her services.
Lee saw the advertisements and guessed she stayed alone, based on previous experiences.
He made an appointment for a massage.
But his true intention was to rob the masseuse as he was in need of money, having been fined in court earlier for a National Environment Agency summons.
He also recalled a previous occasion where he robbed a victim in a lift using a penknife and decided to do the same.
On Jan 19 this year, at about 7.30pm, he arrived at the woman's flat armed with a penknife.
As soon as the masseuse let him in and closed her room door, he whipped out the weapon and held it to her throat.
He announced it was a robbery and ordered the masseuse to strip naked and lie on her bed, which the terrified woman did.
Lee then rummaged through her belongings and found $400 in cash, which he kept in his bag.
He then lay beside the woman, while still pointing the penknife at her.
For the next hour, he sexually assaulted and molested her, and made her perform oral sex on him.
Throughout this, she told him she was in Singapore to earn money to support her family back home.
After he was done, he told her to squat naked at the main door of the flat, close her eyes and count to 20.
He threatened to kick her private parts if she called the police.
She called the cops as soon as Lee left her flat.
Officers tracked him down that night after he had deposited the stolen money into his bank account.
Yesterday, Lee pleaded guilty to one count each of robbery by night and sexual assault by penetration.
Two other charges of molest and sexual assault were taken into consideration for sentencing.
Defence counsel Low Jian Hui said in mitigation his client was remorseful and had to care for his elderly parents.
But Deputy Public Prosecutor (DPP) Kavita Uthrapathy argued Lee showed no remorse for his actions - having been jailed seven years and caned for robbery with hurt in 2000, when he was 23.
The court also heard that Lee had been convicted and jailed for cheating and for property offences in 2012.
DPP Kavita also said Lee committed the offences in the victim's home, where she was entitled to feel safe.
Judge Low, in sentencing, said the court was shocked when it read Lee's criminal record.
The judge added Lee had subjected his victim to robbery, molest and sexual penetration.
"I have no hesitation in sentencing you to 11 years' jail and 24 strokes of the cane," the judge said.
This article was first published on October 07, 2016. Get The New Paper for more stories.