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The Lady Jailer of Greystone – Part 1: Annual Review

Kink & Dominance·EN·2 min read·Published 2026-11-07, updated 2026-11-07·Part 1 of 2

They came to Greystone every year, on the second weekend of October, when the heritage trust closed the gaol for the autumn and let the keys out to a small number of private hirers. Philippa had signed the contract in her own name, as she had every year for six years. She had a cardboard folder under her arm and a cap in her bag.

She was forty-eight, a prison governor in her working life, and the best, by every account, that the county had ever had. Matthias was forty-four, a university registrar, a man who spent his professional life being responsible for other people's records and who, in this one particular building, had once asked her, very quietly, to be his jailer.

In the visitors' room, a bare brick space with a trestle table and two plastic chairs, they sat opposite each other and opened the folder.

"The annual review," said Philippa, in her own voice.

"Yes."

"We will begin with the rules."

They went through them line by line. The Regulations had been written six years ago and amended each year since. No marks. Nothing painful beyond what he had listed. No real humiliation. No photographs. No one else in the building. The cell had a latch on the inside, which had been replaced twice. The word had been Visiting for six years, and he had used it once, in the third year, on a cold night when he was frightened, and she had stopped at once and sat with him until dawn.

"Do you want to change anything?"

"No. Do you?"

"Only one thing." She laid down her pen. "I would like to ask you each year whether you still want this. Not as the Jailer. As myself."

"I do," said Matthias. "More than the first year."

"Why?"

"Because you never once hurried me." He looked at his hands. "And because you always came when I rang."

"I always will." She closed the folder. "Are you content?"

"Content."

"Good." She took the cap from her bag and set it on her head, and a different woman looked at him across the trestle table, cool and unhurried and absolutely sure. "Prisoner. Stand. Hands behind your back."

He stood.

"You have been brought to Greystone for the seventh year running. Do you know why?"

"No, Jailer."

"For being a very good prisoner," said the Jailer, and for a moment the corner of her mouth moved. "Walk."

Continue the story: Part 2 – Visiting.

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Part 2 of 2: Visiting · 2 min read

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