#07: Sister Roberta's Confession

This is a work of fiction. Names, characters, events, and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are consenting adults over the age of 18.

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Sister Roberta was the school's administrator. She was ten years older than the Headmaster, short and heavy, but quite attractive. He liked her large breasts and butt - so different from the young school girls. But what he liked best about her was her almost desperate need for discipline.

Once a week, she would visit his office where he would "hear her confession". She admitted many things to him, often describing them in graphic detail -- things she couldn't bring herself to tell the local priest. He had tried punishing her in various ways but found that she had a high pain tolerance, and he suspected that she enjoyed some of the punishments. So recently, he was trying other approaches.

Last week, she confessed to becoming aroused when she saw Sister Anne in the shower. While Roberta slowly dressed, she had watched the young art teacher lather and scrub her lithe body - and it aroused her.

She could never reveal her feelings to the priest of course, but she trusted the Headmaster to keep her secrets... and to punish her for them. Somehow he combined pain and humiliation with pleasure and reward. Sister Roberta thrived on both, and she found herself always wanting more.

As punishment last week, he had required her to come to his office every morning. She was not permitted to speak except to answer his questions. She was required to disrobe completely, and then clean the room. On the first day, he had simply watched as she dusted his bookshelves, or vacuumed the carpet.

But on the second day, after she had removed her clothes, he had attached a metal clamp to her tongue which she was not allowed to remove until she was done cleaning. Each day thereafter, he had added another clamp: first her tongue, then her nipples, and finally her labia.

"While I attach the clamps, you will tell me what you've done wrong this week." Today was Saturday, the end of her week of punishment. He always saved some special punishment for the last day. Today, after attaching each clamp, he added a weight: a marble-sized piece of lead. He saved her tongue clamp for last so that she would be able to speak.

"Yes, sir." She stumbled through her confession, grimacing each time he added another weight. "I borrowed Sister Anne's hairbrush..." she paused. "without asking her..." Her nipples were being pulled down as if someone was firmly tugging on them.

"Petty thievery is unacceptable of course, but surely the priest could..." he started.

"... and I used it to masturbate," she finished.

"Ah, I see. That's very wrong, Sister Roberta. The stealing could be forgiven, but masturbation? That's obscene. What exactly did you do with this brush?"

She hesitated before admitting "I... inserted the handle into my vagina, Headmaster". She described in vivid detail the young woman's narrow strip of blonde pubic hair - something the Headmaster had not yet seen. Her own was thick, dark, and bushy; and had never been trimmed.

"This is more serious than I realized. First wicked thoughts, then blasphemous action, then degrading behavior." He secured the fifth clamp to her tongue.

"Perhaps this final clamp will help you resist your temptations," he added, spreading her lips and attaching a clamp onto her clitoris. "Now get to work. I want my office spotless today." Unable to respond, Sister Roberta nodded.

Over the next hour, the Headmaster watched the weights dangling from her nipples and labia swing back and forth as she pushed and pulled the vacuum. Behind his desk, he rubbed his hard cock as he thought of new ways to punish her. By the time she was finished, he knew what he would do.

As he slowly removed the clamps (leaving the clitoris until last), he told her: "This is the final day of your penance this week, Sister. Tomorrow we will begin your punishment for your confession today. I want you here early. And bring the hairbrush," he added, handing her clothes to her, and opening the door for her.

"Yes, Headmaster. Thank you, Sir," she mumbled, her tongue still numb and her body tingling with anticipation. Unable to find her thong in the pile, she donned her habit as quickly as she could, hoping no one wandered by as she did.