The Headmaster

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Bastard.

"Now we're going to try the cane, Mrs Jennings."

"The cane," Fiona half said, half gasped. She leapt to her feet and swung around to face him. "The cane?" The very words, still ringing in her ears, somehow heightened the burn in her buttocks.

"Yes, the cane." His features remained neutral. He nodded toward the desk.

Fiona worked the muscles in her lips to say something, but they found no utterance. She lowered her head and returned to her position. The hard wood found her sensitive, needful nipples again, and she narrowed the angle of her spine to give them some relief.

"Flat against the desk, Mrs Jennings."

She pressed herself tight against the furniture, and did her best to gather her breath. Her best wasn't much.

"Five with, five without," the headmaster said.

Fiona scrunched her eyes at the wording, aware of the warmth of his breath on her neck. The faint aroma of aftershave mingled with the scent of her own perfume and lingered in her adrenaline-flared nostrils.

With? Without?

"Ready?"

"What do you mean by with and without?" The question hurtled off her tongue before she had the chance to decide if it was a good idea or not. She braced herself for the answer. And for a possible recrimination for even daring to ask.

"With underwear. Without underwear."

"You have to be jok-" Her lips and tongue froze as she heard the deep, whipping sound of the cane slashing through nothing but air behind her. She shivered, gulped, and blinked long and hard.

"I assure you, Mrs Jennings, it is no joke. Either you're going to follow through with this, or you're not. What is it to be?"

"I-" She sucked a deep breath, pictured her son, and his future, and forced herself back into position with a dejected slouch. Something inside refused to give up the fight, slapping thoughts of indignance and anger about in her skull. "This is highly improper," she muttered, low enough to be hopeful of not being heard. She held her breath, just in case.

"Ready?"

"Yes." She closed her eyes and waited for the pain.

She yelped as the bamboo whipped through the air again, bringing with it no pain, just torture.

Come on.

She tightened her grip on the sides of the desk, screwed up her features and pinched her knees together.

Agony.

She screamed aloud. The impact point, across the middle of her bottom, pulsated with a life-force of its own, tugging at the surrounding flesh and muscles, and unleashing a searing, hot ache as far as her lower back and thighs. She clenched her fists so tight she feared they might rip chunks of wood free from the structure.

"One," the headmaster informed.

"No." Fiona wriggled her legs against each other, and rose her weight up and down on the tips of her shoes.

"Are we really going to go through this every time?"

Fiona bit down on the back of her bottom lip, in a bid to relieve her thoughts of the convulsing misery in her buttocks, for a split second. "Please," she managed, before veering off into a pitiful whine.

"Stand still, Mrs Jennings."

"Jesus Christ," she blurted, the pain now transformed into rage. "It's really sore. Give me a moment."

"I won't stand for that type of language in my office, Mrs Jennings. Two extra without." His voice remained even. Cruel not for its malice, but for its lack of empathy.

Fiona almost chewed through the inside of her mouth, top stop her from saying anything more on the matter. She straightened her hips, sucked her best attempt at a deep breath, and flattened her breasts against the desk.

"Stand still, Mrs Jennings."

"I'm sorry. I can't, my legs are moving of their own accord. It's the pain. I'm sorry." As she spoke she knew all-too-well how pitiful and weak it sounded, imploring, begging. So bereft of even the merest hint of dignity. She didn't care. She just wanted to get the whole thing over with. Regret it later, and complain about it the whole way home, in the car, to herself. She focused as best she could, to abate the knocking of her knees and to balance herself back onto her three-inch heels.

"Take your shoes off."

"I'll-"

"I won't tell you again. Take them off."

Without a further word of argument, Fiona kicked one off, and used it to slide off the other. Her bare feet flattened on the cold floor, and she wiggled her toes against the intrusion.

"Right. Now, are we ready to continue?"

Fiona nodded, taking up her position again, and mumbled "Yes." She closed her eyes, and gritted her teeth.

The second one hurt more than the first. It was as if he aimed for the exact same spot on purpose. One leg buckled, and she was grateful for the support of the desk.

Crack!

The third stole the breath from her lungs. She cried out, but it was silent. Her fingers trembled and she lost her grip.

Her mouth hung open. Quivering. She blinked and tears streamed her face.

Finally she whined. A noised filled with shock and self-pity. She tried her best to bite down, swallow it back, not give him the satisfaction, but it was pointless. Her body was lost. She was no longer in the driving seat.

Crack!

She sagged. Her full weight rested on the desk. One foot lifted off the floor, and her toes twisted so much one of them crackled.

She was just about to cry. Just about to give up and change her mind. Then the fifth blow landed with a hefty thwack.

She sucked hard.

Contorted.

And then she did cry.

The world around her faded into an echo. She reached behind her with arms that didn't want to move, and fingers which could barely feel. Somehow, they found the tender flesh of her bottom, and she stroked over the top of the burning skin. A voice called out to her, but she wasn't ready to hear it. So she ignored it.

A bell.

The shriek snapped her back to her senses. High pitched, and piercing.

She shook her head, blinked, pulled back her hands from her bottom.

"Are you ready?"

She turned her head a little, until her neck stiffened.

The headmaster watched on. Forever patient.

Fiona shook her head. She pleaded without a word. And he returned the favour.

"I have work to do, Mrs Jennings." He glanced at his watch. But didn't push the point.

Fiona used the sleeve of her jacket to wipe the tears and saliva that dripped from her mouth. She snorted hard. Found the ability to fill her lungs again, and settled her body into a slightly more dignified position against the desk.

She didn't know if she could make it. But she knew she had to get it over with. Each passing moment made it worse. Her chest rasped with the effort of her breathing. A tight lump swirled in the pit of her stomach, and threatened to bring up what little breakfast she'd managed to eat that morning.

Still snivelling, and snuffling, she nodded her head.

Afraid he might not have seen it, she coughed some of the detritus from her throat, and spoke. "I'm ready." The words wobbled and turned into a moan at the very end, but they were audible enough.

The headmaster swished the cane through the air. The whipping sound made her heart leap again. Almost to the back of her throat.

"Underwear."

Fiona heard the word. She knew what it meant. But she couldn't put the two together. It took long seconds before she moved her wavering fingertips to her waist. And longer still, to pull at the fabric of her panties until they lowered.

The air of the room seemed chilled now. As if someone had opened a fridge door nearby. It lapped around her exposed bottom. Eased the still fresh welts. A little bit.

"Right down."

Fiona didn't have the energy to sigh. She complied. Until her underwear slid the rest of the way down her legs on their own, and ruffled around her bare ankles.

"Thank you."

She said nothing.

"Ready?"

"Yes," Fiona said. She wasn't. She really wasn't. She never would be, in all honesty. But she just wanted to be out of there, now. Away from the whole damn place.

The pain was unbelievable.

It almost tore her in half. And for a second she struggled with the thought that such a thin layer of clothing could make so much difference.

Then it snapped into place. He'd been holding back. Saving the best for last.

The cane crashed into her skin again.

She cried out loud.

The chill was gone. She burned all over. From her scalp all the way down the soles of her feet. And her entire mid-section seared with the intensity of the sun. Thankfully, some of the pain numbed. Maybe her flesh had reached its threshold. She dared to hope so. But remained afraid all the same.

The third time didn't hurt as much. It didn't hit right. She could tell straight away. And as if to confirm her suspicion, she could hear him tut behind her. She smiled. Through the tears and the wet mess of her face, she smiled. A small victory that wouldn't be long lived, she knew. But a victory all the same.

He made up for it.

In the space of a second he caught her twice. Ripe on the meatiest part of her buttocks. They sounded out almost as one.

She yelled. Screamed.

Her fingers clenched at the desk, but it wasn't enough. Her knees buckled, her body fell back.

She landed on the floor. Clutching at the agonizing scorch that used to be her bottom.

The headmaster stood over her. Watching. Even through the fuzziness of her tears she could see the difference in his eyes. A meanness that hadn't been there before. His shoulders were pushed out, too. His chest swollen. Pride. He was proud of those final two.

Fiona tried to say something. But the pain was so much, all she could do was whimper. And rub at her scarred flesh.

Then it was gone.

His features returned to their usual demeanour.

Like Doctor Jekyll and Mr Hyde. Or the other way around. She couldn't remember which was which.

He placed the cane back on the wall. Onto a little hook. Held it until it balanced, and only then let go.

Without a word he returned to his chair. Eased his weight into it, and gave a light cough.

Fiona didn't know what to do. Or what she could do.

Her whole body trembled.

The worst of it was over. But she was a mess. Physically, emotionally, aesthetically.

She twitched her toes against the floor. Used it as her point of focus. She could move her ankles, too. And then her fingertips. She inched them away from her bottom, and heaved her arms with them. It took a few deep breaths, and some strength she didn't know she had. But sure enough, she managed to reach the desk. And pulled herself upright. She had to twist and contort the curvature of her spine to avoid the floor with her backside.

With a heavy breath born of sheer determination, she pulled herself up to her feet. Staggered, wavered. Finally found her balance.

"I hope we won't have to do this again, one day, Mrs Jennings."

The headmaster was pushing pages into a folder. Straightening their edges into place, and double checking them for neatness.

"I-" Fiona coughed free some salty fluid from her throat. "I hope so."

Her chest was heaving. And, although her crying had subsided, the pain hadn't. She had to use the utmost care while lowering her skirt. And even then it was unbearable. Just the merest touch against her bottom.

"Here, you might need some of these."

When she looked around, the headmaster was offering her a box of tissues. She took them, and started pulling a few out. It took her a good minute to wipe her face dry, and she dreaded to think how bad it all looked.

Her final horror.

She would have to leave this office soon.

She left one hand rested on the top of the desk, while she stepped herself back into her shoes. And with great embarrassment that she couldn't really shield from him, she reached down and picked up her discarded panties. She pushed them into the pocket of her jacket and cleared her throat again.

"May I go now?"

The headmaster nodded. He lifted himself from the seat, and walked around her to the door. Like the truest of gents he rested his hand on the handle, and waited.

Fiona steadied herself. She wiped a few of the tissues around her face again. Coughed, sniffed, wiped at her eyes.

She'd never really be ready. But it was time.

She couldn't really be sure of the look she gave him. It wasn't a smile. Nor was it a glare. Something half-hearted, meek, but definite, she supposed. But he got the point.

He pulled the handle, and the door swung open.

Fiona's heels clicked as she walked the expanse of flooring. She saw him reach out a hand as she grew nearer. Ignored it. Walked on past him.

She kept on walking. Tried not to think of the others in the school. The eyes watching, the ears listening.

Soon, she was out in the cool air of the outside world. And not long after that she was easing herself into the car. Her features twisting in the rear-view mirror as just the effort of sitting down felt like she was being caned all over again.

She leaned forward. Crossed her arms over the steering wheel, and rested her head on top of them.

Soon she might be able to start the car.

Soon.

Maybe.

The End.

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5 Comments
AnonymousAnonymousover 3 years ago
Delightfully impassionate!

So many open doors down this long hallway...I like the idea of the receptionist jealous and wanting more of the same AND asked to further humiliate Fiona....definitely Fiona has to return and ASK for a harder, longer hand-spanking, totally nude this time, and the entire 12 cane strokes eliciting heart rendering pleas and submission. Perhaps Fiona could be invited before the next Staff Meeting so that all his teachers can see how naughty Mom's are disciplined. Her growing arousal, so mortifying, will no doubt lead to the use of all she has to offer. Bravo!!

AnonymousAnonymousalmost 4 years ago
Good work

Nicely written story. If you write more on this subject please keep the cane involved as it is my favourite spanking implement for when I discipline my daughters. A further idea would be to have the head's secretary involved, perhaps both giving and receiving a good hiding. Maybe involve the women teachers to keep them at the top of their game so that the education improves too.

AnonymousAnonymousover 4 years ago
hot, please write more of this headmaster genre. even with the same lady

Good story, please make more!

rmac1rmac1over 4 years ago
I believe there is room for a second visit by Mrs. Jennings to the Headmaster’s office

I agree with the anonymous comment, this visit to his office should have taken place after classes were let out for the day. I personally feel that the first punishment should have been an OTK spanking good and hard for a period of about 2 minutes over her clothing. After which her skirt should have been raised and panties removed and then back over the knee for an additional 10 minutes.

I would then have her bend over the desk and given 15 - 25 swats with a well varnished wooden paddle with holes in it. This punishment really drives home the lesson to be learned. Mrs Jennings could take this lesson home to her son.

To be perfectly honest, I believe Mrs. Jennings is hoping that she again is requested by the Headmaster to meet with him for a second session, to save her son from yet another suspension!

AnonymousAnonymousalmost 5 years ago
A Good Premise

The punishment was over the top. What would have been more realistic with a situation like this, would have been a hard spanking by hand, maybe 10 smacks on each butt check, on her bare bottom, or 5 or 6 whacks of the cane over clothing. The meeting with the Headmaster should have been after the students have left, so no one could hear Fiona getting spanked. Something like this never happens in real life? Who knows? I rated three stars.

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