A man who pretended to a sugar daddy agent duped 11 women into having sex with him so he could "test them out".
He also threatened to share naked photos of two victims who tried to sever ties with him.
He told them that to prevent him from leaking the nudes, they had to have sex with him again.
The conman looked through sex workers' advertisements online and realised he couldn't afford the services.
So 39-year-old De Beers Wong Tian Jun hatched a plan to create a post on online classified asking for paid escorts, referring to 'sugar babes'.
He was searching for babes to provide sexual services to sugar daddies for cash.
At least 11 women, aged between 18 and 24, responded to the ad, between April 2015 and January 2016.
Wong lied to the girls, claiming he had clients who could pay between £4,000 and £10,000 a month for their services.
One woman, 24, met Wong at a Hotel in 2014 and he photographed her topless, and the pair had unprotected sex.
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The woman began having anxiety attacks after the incident.
Prosecutors said: "She would sometimes cry during these attacks, and these were occasionally accompanied by shortness of breath, headaches, nausea and giddiness. In addition, she began having sleeping problems and nightmares."
She was later diagnosed with adjustment disorder by the Institute of Mental Health, AsiaOne reports.
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She begged him to delete the snaps in 2016, but the conman said he would only erase them if she "provided sexual services to him".
When she told Wong she was doing him a "favour" by not going to the police, he told her: "Now I have to pass your photos to my friends, in case anything happens to me, they will use the photos as they wish."
The victim lodged a report with police in February 2016.
Wong targeted at least 10 more women, the court heard.
Deputy Public Prosecutors Cheng Yuxi and Tan Pei Wei stated in court documents: "He also told them that, in order to successfully secure a 'sugar daddy' arrangement with these clients, they had to send their nude photographs to the accused, have photographs taken of them in the nude, and/or engage in sexual conduct with the accused, which were filmed by the accused on some occasions.
"The accused further deceived the victims that these acts were necessary so that the victims could be 'evaluated' by his clients to assess their suitability for the 'sugar daddy' arrangement."
Wong pleaded guilty in a district court on Thursday to 10 charges, including multiple counts of cheating. 26 other charges will be considered during sentencing.
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