#31: Liza's Lessons
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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Liza had been edging every day for two weeks. Several mornings he had brought her so close to an orgasm she almost cried when he stopped. And he always knew when to stop, even when he was just watching. It was like he was reading her mind.
Her plan to submit to the Headmaster had worked, for the most part. He had punished neither her nor Jennifer in weeks. But he had a plan, too. Every day she trained in his office. At first, just an hour before breakfast, but now she was missing most of her morning lessons, and some days she didn't attend classes at all.
He had dozens of "exercises" she was required to perform. Some were simply menial, like shining his shoes or ironing his shirts. She didn't mind these; she even enjoyed spending time near him. She was required to wear a remote control vibrator, which he controlled of course. It kept her on her toes, she couldn't focus at all when he turned it up to one of the higher settings.
A few lessons were objectifying, like serving on her hands and knees as a footstool or a side table next to his desk. These were almost when she was nude, and it was not uncommon for him to have visitors in his office. Most ignored her, but a few did not.
One of the strangest was Ms. Williams, an older woman on the school's board of directors. Liza was serving as a candelabra, standing next to the sofa and holding a lit candle in each hand. The woman had spent several minutes "inspecting" every part of the young girl, even spreading her cheeks and labia.
Sometimes the exercises were humiliating, such as when he made her squat like a dog and pee in his garden. Or worse, when she wasn't allowed to pee at all and had to drink everything he gave her. When she could no longer hold it, she begged him to let her use the bathroom, but he escorted her to class and cuffed her to her desk.
It wasn't long before pee was running down her leg and puddling at her feet. Rachel and Linda loved it and teased her about it all week - especially when they found out Sister Mary made her wear diapers as a punishment.
Others were degrading, such as when he masturbated in the shower and sprayed his cum onto the glass door, and then filmed her while she licked it clean.
Once he tied her hands behind her back and had her kneel next to his toilet. He removed the toilet paper roll and then blindfolded her. He had several visitors over for tea, and two of them used his bathroom. Neither seemed surprised to see her there.
The first was a woman. It sounded like Ms. Williams again, but she wasn't sure. The woman had peed and then stood in front of the kneeling student. When Liza sat there quietly, the woman pulled the girl's head into her hairy mound. "Use your tongue, dear. I want it clean." Liza obediently licked the woman's pussy; she could taste the damp residue of her pee.
Another person came in a few minutes later. He said nothing but pressed his soft cock against her lips until she opened her mouth. She had no idea how old he was, or if he knew her. Then he filled her mouth several times, barely giving her time to swallow before he started pissing again.
Often the lessons were frustrating, such as when he had her play with herself on his floor, always stopping her before she reached her climax. One morning, he tied her to his desk and spent two hours caressing her with feathers and his tongue.
Some lessons were embarrassing, like when he gagged her, and then made her deliver a note to Sister Mary. Easy enough, except he told her she had to be naked and crawling. When she hesitated, he had used lipstick to write "slap me" on her bottom, and told her not to come back until her cheeks were as pink as the lipstick.
Sister Mary assumed Liza was being punished and told her to crawl up and down each aisle so the other students could spank her. Most of the girls just lightly slapped her, but Rachel and Linda both used a ruler that left a red stripe.
A few of the tasks were even more painful. The worst so far was when he opened a big bag of clothespins and attached them all over her body - her nostrils, lips, earlobes, and of course both nipples and labia.
One of the Headmaster's favorites he called "Thirty Thrusts". He took a six-inch dildo with a suction cup base and attached it to the side of his desk. She was required to back onto it until it was fully inside her - first in her vagina, then her anus, and last her mouth. She had to repeat this cycle ten times.
The first thrust was easy enough; she even enjoyed it, though she was never able to climax from it. The second thrust was much harder. She wasn't allowed to use her hands or any lubrication; she just had to force her ass onto it.
The last step - her mouth - was even more difficult for her, though it was more psychological than physical. She had to suck the dildo into her mouth and throat until her lips pressed against its base. After her first rather unpleasant experience with this exercise, she learned to keep her ass very clean.
To make it worse, the Headmaster timed her. Her fastest so far was nine minutes, but he expected her to finish in less than five minutes. Each time the alarm went off before she was done, he punished her. Usually, this meant spanking, but he had many other punishments he could choose from. The worst was "figging". He inserted a peeled ginger root into her ass and made her sit quietly as the stinging pain got worse and worse.
Patience was not one of his virtues. If he thought she was too slow, he "helped" her out. As she backed onto the dildo, he pushed her firmly, forcing her butt against the desk, impaling her. When she turned to take it in her mouth, he smacked her bottom with a leather crop, causing her to lurch forward, taking the full length of the phallus into her throat.
Some days he would interrupt the game to fuck her, forcing her onto the toy with each thrust. Normally, he made her start the challenge over after he filled her mouth, cunt, or ass with his warm cum.
After a dozen sessions, she was getting close to the five-minute goal; today would be the day she succeeded, she thought. He must have thought so too since her normal toy was gone. In its place, he had fastened a much larger dildo: eight inches long and quite a bit thicker.
Her skills were measurably improving. She was able to take all eight inches in her pussy and ass without as much difficulty as she expected. Her throat was still challenging, she gagged on most attempts, though not as often as she had when she was first learning.
Then finally it happened. Three weeks after her daily training had started, Liza deep-throated the dildo for the tenth time, seconds before the alarm sounded.
"Well done!" the Headmaster exclaimed, visibly proud of her. She beamed. He picked her up and laid her gently on his desk, then spread her legs and began to lick her pussy. This time he didn't stop when she began to climax. Instead, he slid his fingers into both her holes, squeezed her breast and nipple with his other hand, and sucked her clit until waves of pleasure begin to overwhelm her.
"Please may I cum, Master?" she begged him. She was required to ask, and for the last few weeks, he had denied her every time. Without stopping, he looked up at her and nodded. She exploded, her legs quivering uncontrollably as she squirted into his mouth. "Thank you, Master," she said breathlessly when she was able to speak again.
He presented her with a wrapped present. "I'm taking you out tonight to celebrate," he told her.
- Following her submission to the headmaster, Liza found herself required to perform various degrading exercises, such as drinking his urine to demonstrate her submission #31: Liza's Lessons.
- One of the most humiliating exercises was when she was forced to squat like a dog and urinate in the headmaster's garden, only to be denied the use of the bathroom and having to drink whatever he gave her instead.
- Despite the humiliation and degradation, Liza found herself submitting willingly to his demands, even indulging in the strange pleasure of licking the headmaster's toilet clean after he had urinated in it, following one of his exercises.
- As part of her training, Liza was subjected to various humiliating and degrading tasks, including peeing in the headmaster's garden and performing oral sex on strangers in his office during a school event, all in the name of her submission #31: Liza's Lessons.