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Headmistress Stories

headmistress

Wishful Thinking

Jack fantasised about being spanked and caned by the headmistress and a friend

Jack didn't know why he was told to go to the headmistress's study straight after the final bell at the end of college for that day. Jack was eighteen and in his final year at college, clearly on his way to university, and was one of the better students b...

The Cane Is Given

The head girl and a student who was given a double detention attend the headmistress' study

Olivia, nineteen, and the head girl at the sixth form college, and Chloe, seventeen, from the first year at the college, both walked into the secretary's office. College had finished for the day except for those in detention so both girls were in their co...

Halloween Opportunity

Do what you want as it's Halloween

Amy was eighteen and at boarding school. Tonight was the Halloween party but she was confined to her dormitory by the Headmistress for her misbehaviour earlier. However, Amy never did as she was told and, once the others had left, got dressed in a sparkly...

Justina's Accusation (YNAS) - Pt. 12

The headmaster is caught having broken several disciplinary rules in his dealings with Justina!

12 - Accusations It took enormous restraint to resist opening the envelope the night before, but I did manage to wait till the following morning. Certain that nothing would be happening before tonight, or likely even this weekend, I didn’t feel in a hurry...

Faith's Double Detention

Faith earns a double detention two days before the end of her time at college, which would mean the cane for the first time in her life.

Faith was tense as she stood in the detention classroom with her arms folded behind her back. Mrs Hudson, the headmistress, was sitting up on the dais at the front of the class. Faith was the only student in detention, admittedly deliberately earning it,...

Another Mistake

Paul earns another spanking and caning this time at the school, and his daughter earns the same.

Paul was nervous as he walked into the school and along the corridor to Miss Foster's office. He wasn't sure why she had sent him a note requesting that he attend her study at exactly 4 pm. However, he thought it better to be there and on time. After all,...

Remembering Miss Templeton

A lesbian couple attend the funeral of a headmistress from long ago and get chatting with a former teacher

Sandhya Chawla and Katherine Dunlop were both aged sixty-one and had started their lesbian relationship at school as seventeen-year-olds. They had been together for the vast majority of the time since and had been married for eight years, getting married...

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Miss Geraldine Culverhouse

A woman encounters her former headmistress after more than thirty years and some things are relived

Judith Saunders was a fifty-two-year-old divorcee and she was sitting in her hairdressers reading a magazine, having arrived early for her appointment. She was sitting in the area near reception and did not look up from the magazine when the outer door op...

Sins Of The Mother

Revenge is sometimes best served cold

Carolyn Harrington-Brown had just come off the 18th hole and was looking forward to a gin and tonic or two in the clubhouse along with the rest of the ladies day golfers when her phone rang. “Hello, Mrs Harrington-Brown, this is St Agnes’ School. It’s abo...

Lucy Hogarth Meets Hilary Matthews Again

Lucy is feeling the need for another severe caning and she gets a call from Hilary

Two months had passed since Hilary Matthews had given Lucy Hogarth the severe caning that had enabled Hilary to release most of her long-held dislike for the bent over Mrs Hogarth. Lucy had contacted Hilary and asked her to deliver the caning that also, f...

The Governor's Meeting - Chapter 2 - The Gym Mistress

School Governor Sarah makes a questionable decision which can only lead to more punishment.

‘Mrs Dickinson, may I ask you something?’ I asked. ‘Please do, Mrs Lonsdale!’ ‘How else could I get punished at the school?’  Mrs Dickinson smiled at me. ‘I take it you are speaking hypothetically? Your interest in punishments at the school intrigues me,...

The Governor's Meeting - Chapter 1 - Awakening

School Governor Sarah is caned by the Headmistress.

I was running late! I’d been dreaming and tossing and turning well into the night and, as a consequence, had overslept. I didn’t want to be late for this particular meeting – I sensed I was already on the wrong side of Mrs Dickinson, the school Headmistre...

The Two Sadistic Sisters

A chance encounter with my former school teachers ends up with a painful but happy ending.

When I was sixteen, I was sent to a private boarding school to study for my A-levels. The school was run by two sisters, both in their late thirties.  Miss Isobel was the headmistress, and Miss Arabella, the deputy headmistress. There weren’t many boys, p...