His young girlfriend was barely three months past her 16th birthday when he convinced her to be part of an Internet chat scam that involved her indulging in sexually charged conversations with their victims.
Alexander Soh Zhi Ren, 22, who came up with the scheme and extorted $104,050 from three young men between February and May last year, was on Thursday jailed five years and ordered to receive five stokes of the cane.
Besides three counts of extortion, he also pleaded guilty on July 4 to seven other charges of various offences.
They include shop theft, forgery and going absent without leave for more than 1 1/2 years while serving his national service in the Singapore Civil Defence Force.
Thirteen other charges were taken into consideration during sentencing.
Soh and his girlfriend, Yap Siew Ting, who is now 17, had trawled Internet messaging chatroom, Alamak.com for their victims and looked for men who were willing to chat with the latter.
She would then persuade the men to strip. When they complied, Soh would record their victims stripping using his mobile phone which was hooked up to Yap's laptop.
The pair later confronted their victims with the video clips and asked them for money in exchange for not uploading the images onto the Internet.
On his own, Soh had also posed as a woman and lured men to chat with him before carrying out the scheme on his victims.
On June 27, Yap was given 24 months' probation and ordered to perform 130 hours of community service after admitting in court that she had taken part in the ruse.
For each count of extortion, on top of caning, Soh could have been jailed up to seven years.
This article was first published in The New Paper.