A former advertising director was jailed for 12 months on Tuesday for two counts of having sex with a 15-year-old female student.
Kwek Chuan Shan, 35, who faced seven charges, had admitted to two charges of sexual penetration of a minor at his Redhill Close flat in November 2012.
He is among five men who have been hauled to court for committing sexual offences with the girl and the third to be dealt with.
Last week, Mexican Alan Lobaton Ramos, 25, a former associate consultant with the Infocomm Development Authority of Singapore, was given 10 months jail on two charges of having underage sex.
In Kwek's case, District Judge Low Wee Ping found the 19-year age disparity to be significant compared to Ramos' case where there was a 10-year difference, which could neither be described as "not significant'' nor "significant''.
The court heard that the minor chanced upon Kwek's profile on a website, which stated that he engaged in "bondage and discipline, dominance and submission, sadism and masochism", or BDSM.
Kwek stated that he was looking for a "submissive" partner. She initiated contact with him and the two began communicating via e-mail. She also told him that she was only 15.
Within a week of befriending one another, the minor went to his flat in early November 2012, when she consented to Kwek performing BDSM acts and taking photographs before they had sex. They met again on Nov 27 that year, when they again engaged in BDSM and other sexual acts.
Deputy Public Prosecutor Sharmila Sripathy-Shanaz acknowledged that the minor was sexually experienced before she had sex with Kwek.
But she said her promiscuous behaviour was entirely irrelevant in sentencing consideration.
"The offence committed by the accused with a girl more than half his age, remains a serious one for which the law provides no excuse," she said.
She highlighted that Kwek's case was "one of an alarming number of recent cases involving men who meet young girls over the Internet and thereafter have sexual intercourse with them.''
In mitigation, Kwek's lawyer Amarjit Singh said his client comes from a respectable family and that he was deeply remorseful for his actions.
The maximum penalty for the offence is 10 years in jail and a fine.