SINGAPORE, July 19 — His sister’s best friend was tipsy and half-asleep in a room at the Downtown East chalet he had rented for his 25th birthday.

Thinking she would be less able to fend off his advances, he proceeded to molest her — all while another three of his younger siblings and his father were asleep in the same room.

For sexually violating the woman who regarded him as her older brother, the self-employed man, who turns 27 in about two weeks, was given 18 months’ jail and four strokes of the cane on yesterday.

The man, who cannot be named due to a court gag order to protect the victim’s identity, had pleaded guilty last month to one charge of using criminal force to outrage his victim’s modesty on July 30, 2016.

The court heard that the victim, who was 23 then, and her boyfriend were at D’Resort in Downtown East to attend the man’s surprise birthday party.

At the party, she had four alcoholic drinks and some food. She stopped drinking around 10pm as she felt tipsy and sleepy.

About an hour later, her boyfriend, along with one of the man’s younger sisters and another female friend, took her upstairs to one of the chalet rooms to rest.

There, she vomited in the attached toilet before she was helped to one of the beds to rest.

The man’s younger sister, two younger brothers and 58-year-old father subsequently went to sleep in the room as well.

While she was half-asleep, she felt a man touch her on her chest and her private parts, before proceeding to masturbate against her body.

Thinking it was her boyfriend, she did not react, until she felt something wet on her body.

At that point, she woke up fully, and saw the man’s shadow making its way to the attached toilet.

She realised then he was not her boyfriend.

She confronted the man when he emerged from the toilet a few minutes later. He told her he had done “nothing” to her and left the room.

Panicking, she went to the toilet to wash herself. Sometime later, she told her best friend — the man’s sister — and another female friend what happened, and began crying. It was not clear if her best friend was the man’s older or younger sister.

When the police arrived at about 3.45am to handle an unrelated dispute nearby, the victim told them she had been molested.

She fainted and was sent to the hospital, where a doctor noted that she was “teary and distressed” when recounting the events. She was also given an emergency contraceptive.

The man was subsequently arrested. Analysis of the victim’s underwear and bedsheets found that his DNA was on them.

Citing several aggravating factors, deputy public prosecutor Gail Wong argued that the degree of sexual exploitation was “particularly egregious”.

“The accused was persistent and pre-meditated in the contact … it was easier for the accused to take advantage of the victim’s half-sleeping state, and the victim would have been in less of a condition to resist any sexual assault,” Wong said.

Adding that there was betrayal of trust, the prosecutor said the victim would have felt safe enough to rest there without having to go home, as she was accompanied to the room by her friends and the accused’s family.

Because of her half-asleep state, the victim would not have known if she had been sexually assaulted or whether there was sexual penetration as well, said the DPP.

In mitigation, the man’s lawyer, who asked for six to eight months’ jail, said: “At all times, the victim thought it was her boyfriend who was having contact with her. Is there distress? Is there harm?”

To which District Judge Ng Cheng Thiam retorted: “If it had been the boyfriend, there would have been consent.”

For assaulting or using criminal force to outrage her modesty, the man could have been jailed up to two years, fined, caned, or any combination of the three. — TODAY