Chris Nairn, head of St Roch's Secondary in Glasgow, was accused of sexual harassment by Mary Robinson, an English teacher at the school, who says she was victimised as a result of raising her complaint.
Glasgow City Council and Mr Nairn deny the allegations.
In her evidence to an employment tribunal this week, Mrs Robinson made a string of claims about Mr Nairn's conduct towards her, including remarks such as "phwoar, aren't you a babe" when she approached him in the school corridor wearing a skirt and heels.
She also claimed he would tell her: "I love you to bits."
Mrs Robinson alleged Mr Nairn told her not to wear trousers to school, "insinuating I was having a bad effect on pupils". She pointedly turned up on the first day of the hearing wearing a black-cropped trouser suit and high-heeled boots.
Mrs Robinson, from Greenock, further alleged that Mr Nairn had made a crude remark when drunk during a Christmas staff night out in December 2002. She claimed that she overheard him say: "This is a f*nny parade - anyone you want in here you can have them."
Mrs Robinson, whose children were 18 months and eight weeks old when her husband died six years ago at the age of 35, had previously been on sick leave suffering from stress and depression after the loss of her partner, then an uncle, her father and the serious injury of her brother.
After her return, she claimed she was harassed and found this "more destructive" than the death of her husband. Following an investigation, the city council concluded certain comments and behaviour were unacceptable but did not amount to deliberate harassment. She felt the outcome implied it was her reaction rather than Mr Nairn's behaviour that was the problem.
Mrs Robinson described Mr Nairn as "over the top", "unpredictable" and "very theatrical". She claimed she had seen pupils humiliated, mortified and embarrassed by his behaviour.
Asked by the tribunal chairman if Mr Nairn commanded the respect of pupils, she replied: "I'm not sure. I know he can instil fear in pupils. He can be friendly to pupils. I don't know if there is consistent respect."
Mrs Robinson said that, on her return to school, she felt as if she had a "mountain to climb" to rebuild damaged relationships and update her knowledge of the school curriculum.
She accused Glasgow City Council of disregarding and trivialising her complaints.
"I feel I have been trivialised because I am a woman," she told the tribunal. "I have been attacked because of my previous situation. I have not been allowed to start afresh. Having returned from a number of absences, I immediately felt guilty and didn't feel I could ask for extra support.
"I feel I am being judged for that, being discriminated against because I had so much time off."
Mrs Robinson is still employed at the school but is on sick leave. She agreed with Clare Elliot, the council solicitor, that she had never been refused leave of absence but said she was often frightened to ask as she feared Mr Nairn's reaction.
"He could be angry, go back and criticise me for previous situations. He would say, 'you have had time off before. I have been good to you. The school has been good to you'."
The prospect of returning to St Roch's was a nightmare which made her very sad as her job was the only thing that had stayed constant during all the previous problems in her personal life.
Miss Elliot said Mr Nairn's position was that he had been supportive towards Mrs Robinson. The tribunal heard she had been diagnosed as suffering from a major form of depression. Mrs Robinson, who is being supported by the Educational Institute of Scotland, wants the tribunal to award compensation for injury to feelings and lost earnings.
The hearing was continuing as we went to press.