He promised to help them remove their nude photos from the Internet. But they, in return, had to become his sex partners.
Polytechnic student Winfred Quek Xiu Zhi, then 19, had made this "indecent proposal" to two models whose nude photographs he found on a website and even threatened one of them.
Yesterday, Quek, now 21, was sentenced to 10 weeks' jail for criminal intimidation.
The court heard that in 2013, Quek messaged one of the models, also 19, telling her that he could help her remove the photos from the website if she were to be his sex partner.
When the girl ignored him, he contacted the second model, a 20-year-old freelancer. Around August 2013, calling himself "Justin", Quek called her and claimed he would help remove her photos, and that he had them.
The next day, he lied to her that he had paid $6,000 for her photos to be removed from the Sammyboy website and wanted her to provide sex to him for free. She initially agreed but changed her mind.
On Jan 5 last year, while exchanging messages, Quek badgered the victim and urged her to "limit the damage" caused by her nude photos being "leaked" on the front page of the website.
He also lied that he had spent thousands of dollars to remove them. In return, he expected her to provide sex to him. He accused her of reneging on her offer and asked whether it would be "good" if her boyfriend saw her nude photos. But she said she did not care.
Quek gave her "one last chance". When she did not reply, he wished her luck and told her: "You will one day remember your stupidity."
Yesterday, District Judge Lim Keng Yeow said this case clearly did not involve just an idle threat. The threat was one of trading the victim's nude photographs publicly or of making them available publicly if his demands were not met.
"(Quek) gave every impression that he had the capability, the motivation and the readiness to carry out his threat so as to strengthen the force of his demands," he said.
He said there was clearly a measure of calculation, deception and premeditation in how the offender went about trying to get the victim to surrender to his demands.
Deputy Public Prosecutor Marshall Lim had earlier objected to probation, which the defence had asked for. He said that this was not the work of a naive or immature individual.
Quek, who could have been jailed for up to two years and fined, is appealing.
Bail of $15,000 is allowed.