A woman made plans to meet up with her former boss when they were both in Singapore last February.

But the planned dinner at a restaurant turned into a night of drinking, "risque" conversation, and alleged rape or sexual assault.

Her former boss, a 49-year-old male known as "A", along with a second man, 50-year-old "B", went on trial on Sep. 2 for charges of rape or sexual assault, molestation, and obstructing justice by deleting messages to each other, CNA reported.

They cannot be named due to a gag order on their and the victim's identities. While their nationalities cannot be disclosed, CNA noted that both men are foreigners.

Meeting for dinner

The alleged victim had previously worked under A and continued to stay in touch.

She did not know B — who had been friends with A for 20 years — personally, but was aware of his "professional reputation".

Upon discovering that they would both be in Singapore at the same time, A suggested meeting the victim for dinner.

They made plans to meet up for dinner at a restaurant on Feb. 26, 2023.

But no dinner

However, the dinner never took place.

That afternoon, both men drank alcohol in B's hotel room and shared a portion of viagra.

Both A and B were staying at different rooms at the Carlton Hotel in Bras Basah.

They were later joined by a 52-year-old woman known as Ms J,  who previously had a "casual intimate relationship" with B.

Ms J and B kissed on the bed while A was seated in the corner of the room.

The men then allegedly mentioned having a threesome, but were rejected. At around 6pm, Ms J left for her own dinner appointment.

Afterwards, when the dinner appointment between A and the victim was supposed to take place, A asked her to instead purchase three to four cans of tonic and head to his hotel room.

Both men then invited her to drink and encouraged her to "bottoms up".

Passed out

The conversation turned "risque and bawdy", CNA reported.

While she had initially planned to get dinner after the drinking session, she passed out.

She then drifted in and out of consciousness, unable to open her eyes.

While she allegedly has no memory of what happened next, she claimed that someone removed her clothes and she was violated on various parts of her body.

She also alleged that she said "no" many times.

A left the hotel room at about 8:20pm. At 1am the next day, the woman woke up and realised she was naked in bed with B.

Her whole body also felt sore and she had a headache and difficulty breathing.

At 3am, she woke up again. She dressed herself and asked B what had happened, and why she was naked.

She also told him she felt she had been raped, the court heard.

"How are you feeling?"

At 12:43pm, A sent the victim a text message to ask how she was feeling, and said: "Not going to be drinking for a while now?"

She replied: "(redacted), can you explain to me what happened last night?"

They then agreed to meet for coffee later, as she said she was "still weak".

Before the appointment, the woman went to Raffles Hospital for an examination as she wanted to find out if she had been sexually assaulted.

She was referred to KK Women's and Children's Hospital, which lodged a police report.

The two men were subsequently arrested at the hotel later that afternoon.

B is also accused of deleting his communications with A, including a photo he had allegedly taken of the victim lying naked on the shower floor, sometime before the police arrested him.

Trial continues

CNA reported that the prosecution will ask to admit statements by the two men in the form of video recordings, where they allegedly admitted to the acts.

They will also call in witnesses from Carlton Hotel and doctors from Changi General Hospital and the Institute of Mental Health's Department of Forensic Psychiatry.

For rape and sexual assault by penetration, an offender could be jailed up to 20 years, and fined or caned.

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