A female teacher at a prestigious Sydney private school had been warned about her behaviour towards students before she started a sexual relationship with a 17-year-old boy.
The woman, 33, had sex with the year 12 schoolboy multiple times while she was a teacher and he a student at the elite Sydney Grammar School in the inner city suburb of Darlinghurst.
The relationship continued over three months last year, with the pair meeting to have sex in a store room and classroom at the school and at the woman's home.
After the boy attempted to end the relationship, the woman sent him lengthy messages describing herself as a "monster", saying she was "too happy or too stupid to see the signs" and asking "am I going to go to gaol?"
According to an agreed statement of facts tendered in court, the woman had been employed as a teacher at Sydney Grammar since January 2008.
On four occasions between 2013 and 2014, the woman was warned or contacted about inappropriate behaviour towards students with the school expressing concern a "pattern" was developing.
"You must not in any communication with boys of the school, written or spoken, or electronic, make any sexual references or use terms with obviously sexual connotations," a letter sent to her stated.
The teacher was also reprimanded for forming an "overly close pastoral role" with a male student with a mental health problem and was "directed not to do this again".
According to the facts, the woman and boy, who was suffering from depression, developed a relationship when they were working on a extra-curricular school activity together.
The woman started sending text messages to the boy about her family, health problems, depression and gave him poems and letters.
They had sex the first time at the woman's home and then mainly met up in the evening at the school. The woman, according to the court documents, made the boy write sexual fantasies for her and she wrote them for him.
The boy attempted to break off communication with the woman in April last year, but she continued to text message him up until the police were contacted in September 2016.
According to the court documents, the boy was frightened to end contact with the woman because he thought she might harm herself.
"We agreed to sever contact," the boy wrote in one text message.
"I didn't have much choice. I'm finding it so hard. I'm doing my best," the woman responded.
"There was a while I didn't feel like I had much choice either. Guess that's fair," the boy replied.
"I'm so, so sorry about that. I had no idea. I thought I was making you as happy as you were making me. You never even hinted. I hate myself for not seeing it in time."
In another message, the woman wrote: "I see that it's my own foolishness and selfishness that have led to it. That you've been hurt by those things is unforgivable ... I'm a f...... monster but I'm so, so, so sorry."
The boy told his friends what had happened, and the woman was arrested by police in October.
In the Downing Centre Local Court earlier this week, the woman pleaded guilty to six counts of having sexual intercourse with a person under care.
In a statement last year, Sydney Grammar headmaster John Vallance said the teacher had been suspended as soon as the school became aware of the allegations.
Parents had been notified about the situation, Dr Vallance said, and support had been provided.
"The employee concerned was suspended and forbidden to have any contact with pupils pending the outcome of the matter," Dr Vallance said.
The woman's bail has been continued and she will face court again later this month.