SINGAPORE - They invited their former secondary schoolmate to a reunion at a flat.
But when she passed out drunk after a series of drinking games, the two men took advantage of her.
One sexually assaulted and molested the victim, now 29, and another took photos of her in various states of undress and in compromising positions.
The incident took place in 2009.
The men, both 29, were sentenced to jail on Thursday.
The one who sexually assaulted her will get seven years in jail and nine strokes of the cane, while his friend who took the photos was sentenced to 19 months in prison. The former is appealing the sentence, and the latter is considering an appeal.
They were offered bail of $30,000 and $25,000 respectively.
None of the trio can be named to protect the victim's identity.
The men were convicted in November after 49 days of trial.
Assistant Public Prosecutor Raja Mohan had called for a heavy sentence, saying they had "despicably subjected her to base sexual acts to satisfy their odious sexual desire".
The victim had believed other school friends would be at the Bukit Panjang flat but arrived to find only the two men, whom she had known for nine years.
After some catching up, they played drinking games and she eventually passed out unconscious.
In the stupor that followed, she remembered "giggling voices and camera flashes", and pain in her private parts. A medical examination later found a tear in the area.
As the alcohol wore off, the woman called other people, including her then boyfriend. She later made a police report.
APP Raja Mohan said: "The victim regarded the accused persons as her friends. The accused persons, however, violated the very sanctity of this friendship."
He added that the duo "remained unrepentent to the very end". One tried to bribe others to persuade the victim to drop the matter. They also attempted to paint her as a promiscuous woman.
The mother of the man who got seven years inserted a mitigation plea for her son, saying he held moral values and some women try to cry wolf after an incident.
But District Judge Marvin Bay agreed with the prosecution that the men had violated the sanctity of the friendship.
Judge Bay added that both men were gainfully employed and successful in their chosen fields, which may be a reason why they chose to contest the charges against them.
"If anything, (they are) all too conscious of what they will lose if they (are) jailed."