He was given a 12-month conditional warning in October 2013 after he was caught trespassing and exposing himself in a girls' school.
About seven months later, even though Daryl Wee Yi Yang, 17, was supposed to stay out of trouble for a year, he went back to his old ways and trespassed into another girls' school.
The teenager, who works in the service industry, was put on probation for 18 months yesterday after he pleaded guilty to one count each of criminal trespass and performing an obscene act in public.
One count of theft and a second trespassing charge were taken into consideration during sentencing.
Deputy Public Prosecutor (DPP) Cheryl Seah said that Daryl trespassed into the first school in the north-eastern part of Singapore at around 1pm on April 13, 2013.
He approached a 14-year-old student from behind as she was walking up a flight of stairs to the fourth storey.
When she reached her destination, he touched the girl's left shoulder and she turned around - only to see him stark naked.
Daryl then asked her if she could perform oral sex on him.
The girl declined and walked away.
Feeling afraid, she pretended that there was a teacher nearby and told the intruder about it, causing him to flee down the stairs.
The student alerted a school security guard and Daryl, who managed to slip on his clothes, was caught when he tried to leave the premises.
The police were alerted and arrested him soon after.
DPP Seah said that Daryl trespassed into the second school in the central part of Singapore on May 29 last year.
He entered the premises at around 4pm by lying to a security guard, claiming that he wanted to pass a mobile phone to his sister.
The guard directed him to hand it over at the general office and told him not to go to other parts of the building.
But Daryl went around the school to look for girls' uniforms to wear.
After getting hold of a jacket and a pair of PE shorts, the teenager went to a toilet to change into them.
He emerged soon afterwards, wearing them and was walking around when a teacher spotted him.
He informed the police and Daryl was caught for the second time.
Daryl's lawyer, Mr Louis Joseph, told the court in his mitigation plea that his client had been diagnosed with "transvestic fetishism".
Quoting the doctors who had assessed the teenager, Mr Joseph said: "(Daryl's) teenage curiosity and experimentation about the opposite sex might have led to his cross-dressing behaviour, in which he derived sexual arousal and satisfaction".
Because of this, one of the conditions of his probation is that he has to undergo counselling and treatment programmes.
Daryl must also perform 60 hours of community service and remain indoors between 10pm and 6am every day.
His father also had to put up a $5,000 bond to ensure his good behaviour.
Responding to queries from The New Paper, the Ministry of Education said that beyond the school security guards screening visitors to the school, staff and students are also reminded to be vigilant and report suspicious behaviour in the school to the general office.
Its spokesman said: "These measures have proven to be generally effective in ensuring that our schools are safe."
For performing the obscene act, Daryl could have been jailed up to three months and fined.
And for committing criminal trespass, he could have been jailed up to three months and fined up to $1,500.
(Daryl's) teenage curiosity and experimentation about the opposite sex might have led to his cross-dressing behaviour, in which he derived sexual arousal and satisfaction.
- Daryl's lawyer, Mr Louis Joseph, explaining his client's behaviour
This article was first published on Feb 14, 2015.
Get The New Paper for more stories.