He had robbed two women and molested one of them in their home.
Tan Choon Keap took his perversion one step further and ordered them to strip on Nov 3 last year.
Naked and afraid, the women were forced to make the "V" sign while he snapped pictures of them with his mobile phone.
Tan then threatened to post their nude photos online if they made a police report against him.
The married man did all this while out on bail for another crime - robbing a prostitute and making her perform oral sex on him without her consent.
All three victims were Chinese nationals.
Tan, 34, an interior designer, pleaded guilty in court yesterday to three counts of robbery and one count each of outrage of modesty and sexually penetrating a woman without her consent.
Eight other charges for offences, including three counts of wrongful confinement and two counts of criminal intimidation, will be taken into consideration.
After his arrest, Tan told the police that he robbed the two women last year as he had lost money in gambling and had borrowed money from loan sharks.
He had made a massage appointment with one of his victims, a 29-year-old woman, and turned up at her home at 9.10pm on Nov 3. During the session, he asked the part-time masseuse for sexual services but she turned him down.
Tan went to a bathroom after the massage and when the woman's back was turned, he took out a Swiss Army knife and held its blade against her neck. He told her that he would not hurt her if she did not shout or struggle.
He also taped up her mouth and ordered her to give him cash totalling $4,000, which she had kept in a drawer.
Tan then tied her wrists and knees with cable ties before ordering her to strip naked. He snapped pictures of the woman with his mobile phone and molested her.
When Tan spotted her 21-year-old housemate stepping out of her room, he rushed towards the younger woman and covered her mouth with his right hand.
He asked the student to lead him to her room before carrying the 29-year-old woman there.
Tan then robbed the younger woman of $4,000 and told her to hand over her belongings, including her passport and student pass. He then tied the student's wrists and ankles with cable ties.
He also searched her luggage and helped himself to an additional $10,000 cash which belonged to the older woman.
Shortly after, he ordered the women to pose naked and make "V" signs while he snapped their pictures.
After that, Tan set a timer on the student's iPad for 15 minutes and told the women that they could free themselves only when the time was up.
Tan fled the scene and when the iPad rang, the women freed themselves and informed the police about their ordeal.
Later, the older woman discovered that he had also taken her other belongings, including her passport and $900 mobile phone.
Deputy Public Prosecutor Jason Chua said that officers arrested Tan at the Resorts World Sentosa casino two days later.
Tan later admitted that he had used part of his ill-gotten gains for gambling.
He will be back in court on Aug 8.
For each count of robbery, he can be jailed up to 14 years and receive at least 12 strokes of the cane.
For sexually penetrating a woman without her consent, he can be jailed up to 20 years and fined or caned.
This article was first published on July 1, 2015.
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