Pretending to be a woman, former national badminton player Ashton Chen Yongzhao set up a Facebook account in late 2013 so that he could chat with girls about their sexual experiences.
Calling himself "Qing Hong", he befriended a Secondary 1 student and later told the girl that there was a man who was interested in her.
As this man, and calling himself "Sotong", Chen started chatting with the girl, then 13.
The pair met in early 2014 for the first time, at a Tampines block of flats. There, she performed oral sex on him at a staircase landing.
Chen, 28, was jailed for two years and four months yesterday after pleading guilty to three counts of engaging in consensual sexual activities with the girl.
Three other charges for similar offences involving the same minor were considered during sentencing.
The court heard that about a year after the initial encounter, "Qing Hong" contacted the girl again and found out that she had indulged in sexual activities with her boyfriend.
"Qing Hong" asked the girl if she was willing to have sex with a man. The minor replied that she was not interested, as she wanted to remain loyal to her boyfriend.
But between late 2015 and early 2016, the teenager told "Qing Hong" that she would meet Chen only if he could help her.
Deputy Public Prosecutor Sruthi Boppana told District Judge Hamidah Ibrahim yesterday: "The victim explained that she was in need of money. 'Qing Hong' then responded by saying that the accused would be willing to meet her and asked whether she would be willing to perform oral sex and have sexual intercourse if he gave her money. The victim agreed."
Chen later met the girl, then 14, at a Simei multi-storey carpark and he gave her $80. She performed oral sex on him and they had protected sex. The girl contacted Chen again in July 2016 as she was still in need of money.
He gave her another $80 at the staircase landing of a Simei block of flats and she performed oral sex on him. The pair stopped communicating with each other after this encounter.
Yesterday, DPP Sruthi urged the court to jail Chen for two years and nine months, stressing that his offences were not one-off incidents.
Chen's lawyer, Mr Terence Seah, pleaded for his client to be jailed for one year and four months. He added that Chen had served the country well as a sportsman and had "brought glory" to the nation.
Chen's run as a professional badminton men's singles player ended in April 2014. He was then the men's singles world No. 69. At one point, he reached a career-high ranking of No. 50 and was Singapore's second-ranked singles player behind Derek Wong, who was then at No. 47.
Chen was also a member of the men's team that won a silver at the 2007 SEA Games and bronze in the same competition in 2009 and 2011.