Feigning concern for a tipsy Taiwanese tourist, he told her he was taking her to a hotel to rest last November.
Instead, Ng Jun Xian, then 20, sexually assaulted the 23-year-old woman and even tried to rape her.
When she fought back, he was surprised by her will to defend herself.
Yesterday, he got another surprise when the judge jailed him for seven years and two weeks, and ordered him to be given six strokes of the cane.
Ng was so stunned, he gasped when the sentence was passed.
Ng, who was then a full-time national serviceman, got to know the Taiwanese woman at Club Sonar in Orchard Hotel last year when she came here to visit her boyfriend.
On Nov 8, 2014, Ng sent her a text message to meet at the club. He was with a friend.
At about 4am, the woman wanted to go back to her hostel at Race Course Road, but Ng said he would take her to a hotel where she could rest.
They went to Hotel 81 at Lavender Street, a move which Community Court Judge Mathew Joseph called "devious".
In the room, Ng tried to kiss the woman, but she rejected his advances and bit him on the lip.
During sentencing yesterday, Judge Joseph said: "You could, and should, have stopped your advances at this point and apologised to her, but you did not. You were intent to continue to molest her."
As Ng continued his attack, the woman struggled and shouted in Mandarin, "don't want, don't want, don't touch me". She even bit him all over so he would stop.
Ng's friend, who was returning from a smoke break, heard the commotion from outside the room. He banged on the door and shouted Ng's name, but was ignored.
Ng then pushed the girl onto the bed where he sat on her and sexually violated her with his fingers. He also tried to rape her, but was unsuccessful.
Making his comments before passing down the sentence, Judge Joseph called the incident a wanton sexual assault on the victim.
"Your attacks were persistent, prolonged and perverse... Sexual misconduct was prolonged and there was escalated sexual assault, which must have cumulatively been a terrifying ordeal for the victim."
"You were … bold, brazen and despicable in your assault," Judge Joseph told Ng. "It's purely fortuitous that due to her tenacity, the victim was able to avoid being raped by you."
When the woman managed to break free and run towards the door, Ng grabbed her and slapped her hard across the cheek before pushing her back to the bed.
The struggle continued and the woman grabbed a coffee cup and threw it at Ng, who suddenly stopped, knelt down and apologised to her.
She took the opportunity to dress herself and leave the room. She made a police report and Ng was arrested that day.
While out on bail, he got into a brawl in a pub with other patrons after one of them punched his friend after a confrontation.
In August, Ng pleaded guilty to one charge each of sexual assault, attempted rape and disorderly behaviour. Another two charges - one each of outrage of modesty and voluntarily causing hurt - were taken into consideration during sentencing.
Ng, who was dressed in a black long-sleeved shirt, could be seen trying to hold back tears as Judge Joseph made his comments. He let out an audible sob when the judge said he would be caned.
Yesterday in her oral submissions, Deputy Public Prosecutor (DPP) Zhang Hongchuan called what Ng did a brutal and heinous crime.
She noted that it was also not his first brush with the law and he had a history of violence.
She said: "In the present case, violence was also used, albeit not to obtain property. His record shows propensity to re-offend for crimes of violence against the person."
Referring to a report for his suitability for reformative training, DPP Zhang added Ng was not remorseful and in fact, tried to pin the blame on the victim by saying she attacked him when he refused to spend the night with her.
Ng's lawyer A. Rajendran said his client would appeal against the sentence.
This article was first published on October 8, 2015.
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