Headmistress From Hell

Story Info
A father takes his son's punishment.
2.9k words
4.49
103.1k
34
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
krr1957
krr1957
1,570 Followers

As he walked into the school he felt his anger rising. The new headmistress had only been there for three days and now his son was suspended! Alright, so he had split the other lads lip but they were teenagers, it was only natural to fight at that age. It was hardly his fault that the other lad was a wimp who could not defend himself. He walked quickly along the echoing corridors, past empty classrooms, to the headmistresses study. He grabbed the door handle and wrenched the door open.

"Knock before you enter!"

He stopped in his tracks and then backed out of the room. It was only once he was outside of the door again that he cursed his reflex and wondered what the hell he was doing. He knocked at the door harder than necessary.

"Come!"

He entered the room.

"I'm looking for Hardacre"

"I'm Miss Hardacre"

Now he was completely thrown. He was geared up to meet some old battleaxe. According to his wife Hardacre had previously been head at Peebles Day School for Boys where the record for outstanding academic achievement was second only to its reputation as one of the strictest schools in the country. This woman was not out of her early thirties and, in her immaculately tailored business suit, she looked more like a fashion model than a teacher. Her thick blond hair formed a halo around her perfectly made up face and as she pushed her chair back from the desk his eyes were drawn to her long silk sheathed legs.

She extended a hand

"Mr Trott, let me introduce Mrs Cole. It was her son that Lee had the altercation with"

He nodded to the other woman. Under other circumstances he would have found her very attractive, slim, with auburn hair cut pageboy style but Clariss Hardacre's physical presence filled the room like smoke.

"What do you mean by suspending him for one month?"

Clariss Hardacre sat completely unfazed by the outburst.

"I would call him a very lucky boy. My recommendation to the govenors was that he be expelled. They decided, having talked with Mrs Cole, who has shown remarkable tolerance, that he be given a second chance"

“Expelled ..!" He sat forward in his seat. "It was just a fight for God's sake. In my day you would get six across the backside and then forget about it!"

Clariss raised an eyebrow

"I can assure you that any boys to whom I administered six would remember it for the rest of their lives"

He laughed.

"With all due respect you're a female. I was caned by blokes twice your size more times than I care to remember. You just grit your teeth and don't give them the pleasure of knowing they've hurt you. The next day its all forgotten"

Clariss leaned forward her elbows on the table and her chin resting on the backs of her hands.

"Do you know what that is behind you Mr Trott?"

He craned round and looked at the piece of equipment that dominated the centre of the room. He had paid it no heed on his way in but, now that he looked, it appeared like something more appropriate to a gymnasium. It looked like a letter "A" , a large hump covered in tanned pig skin.

"No idea"

"Its a whipping block Mr Trott. Peebles school gave it to me as a parting gift. I'm going to have it installed in the school hall."

He laughed again

"And you think these young lads are going to be frightened of it?"

It was Clariss' turn to smile and there was something in her look that puzzled him

"I'll tell you what Mr Trott. How would it be if you took your son's punishment? You take half a dozen from me over my block and I'll reinstate Lee with immediate effect"

She looked at Mrs Cole who raised a questioning eyebrow.

"You have to be joking."

"I'm deadly serious and, after all, I'm a mere female .."

"It's fucking perverted!"

"It's your choice"

He looked at the two women and with a sense of fatalism he realised he had no choice. If Lee was left at home alone for a month the house would be wrecked. It would be all the excuse his friends needed to bunk off school themselves.

"Okay I'll play your stupid game but Lee comes back to school in the morning."

"Agreed. Now if you would like to position yourself ..."

"Over that thing?"

"Of course “over that thing” . You'll take it just like the boys."

With a sneer he crossed to the hummock and, with an effort, mounted it. With his shoulders beneath the level of his buttocks he felt an uncomfortable rush of blood to his head. Clariss rose from her chair and came towards him. She knelt by his side and he felt the start of an erection as more of her stunning legs were revealed and he was exposed to her tantalizingly musky perfume. His arms rested naturally on two legs at the front of the device from which two leather straps hung. She took each strap slowly in turn and buckled them tightly around his wrists.

"Is this necessary?"

"We don't want you falling off and claiming for a broken limb do we?"

She fastened more straps around his calves and another across the small of his back he then jerked as he felt her hands at his belt buckle

"Hey! Whats going on!"

"Sorry. Did I forget to mention? The boys have to take it on the bare skin. Mrs Cole could you give me a hand here?"

Mrs Cole gave a mocking smile as she came and helped drag his trousers down.

"Ouch! Watch it!"

They made no allowance for his erection as they wrenched the material down below his knees and his manhood finished up painfully flat against the hummock pointing towards his toes. They could not miss it but neither woman said a word. Clariss fastened yet more straps around his bare thighs and his freedom of movement was nearly totally diminished. He heard her moving around, her stiletto heels, clacking on the parquet floor, but he could not see what was going on. Finally she appeared in front of him holding a collection of canes and what appeared to be a dogs toy bone made of heavy rubber.

"Would you like something to bite on?"

"Don't be stupid. Just get it over with"

"Are you sure? You see, if you scream, I'll start all over again."

"Do you get your kicks out of this? I agreed to take six and I won't be screaming"

"We'll see. If you do feel the need to scream please feel free. The school is empty except for we three" Clariss removed her jacket and he could see the outline of her nipples as they stood out through the material of her bra and her satin blouse. The bitch was getting off on this!

She moved out of sight and then started speaking to Mrs Cole.

"We'll start with this one. It's a Babcock. Its quite thick and if applied properly raises a very nice weal."

He flinched as he she whooped it experimentally through the air.

"Once the weals are raised we can use the Harrow. You can see its a lot thinner but it will cut right into the ridges. I hope you're not squeamish about the sight of blood."

Mrs Cole spoke for the first time since he had entered the room.

"No, not at all. After all I am a nurse. Spare the rod and spoil the child."

"Will you cut the bullshit and make a start."

"Tut Tut. Patience is a virtue"

Her footsteps could no longer be heard and he knew she was standing poised but still she kept him waiting. Finally he heard it.

Whooop! Thwaaaackk!

His eyes opened wide and for a split second there was silence until suddenly his breath exploded from his lungs so quickly that his vocal chords could not react. His silent scream marked the most excrutiating pain he had ever felt. As a builder he was forever banging, knocking and burning himself but nothing could prepare him for this. He suddenly knew he had made the wrong decision

"Stop this now! I'm not going through with it!"

Clariss' smiling face filled his field of view

"It's no longer your decision to make"

"Let me up from here! Lee stays home."

"Mrs Cole? It's up to you."

Mrs Cole knelt so that her face was side by side with Clariss'

"He made his cross. Now he's got to bear it. Please continue Miss Hardarce."

"You bitches!"

There was an awful silence as they moved away and he gritted his teeth. The first one had caught him by surprise but he would be ready this time. After what seemed an interminable wait he heard the dread noise again.

Whooop! Thwaaackk!

The first had been bad enough but this was worse. Directly under the first stroke it reignited the initial pain and added to it.

"MMMMMmmmmmm!"

Not quite a scream but tears started to his eyes.

The third stroke followed quickly and this time he could not contain the expletive.

"SSSSHHHHiiiittt!!"

He was almost weeping as he spoke, addressing himself to Mrs Cole.

"Look I'm sorry for what Lee did. But this is inhumane. Would you subject your husband to this?"

"My husband walked out and left me when my son was three weeks old. I'd give anything in the world to have him where you are now. In my book all men are shits and I think that Miss Hardacre may be really on to something here."

He had played his last card. His only hope now was the remaining strokes would be layed on with the thinner cane that she had spoken of.

"We'll need to give it a minute or two before the weals become really tender. Can I offer you a sherry?"

"I'd like that."

He couldn't believe it. They were going to stretch it out even further. As the two women sipped their drinks he felt the skin on his buttocks tighten and the growing pain ratcheting upwards notch by notch. It was as though someone was holding a hot iron inches from his skin. In the event it was more than ten minutes before they turned their attention to him again. He felt delicate fingers trailing over his tortured skin and then Clariss' voice.

"They are up a good eighth of an inch, just perfect for our purposes."

He heard the cane swished through the air. The note was higher this time, less solid sounding, but somehow all the more menacing for it. He braced himself, just three to go, he could take it. Then it came, out of nowhere.

Thwaccckkk!

She left it pressed against his skin and, for a second, there was no sensation but when she lifted it away his blood rushed to fill the void from which it had been so rudely expelled. The pain centred on the stripe she had inflicted on him but this time it seemed to trigger every nerve in his body. The next stroke caught him whilst his body was still in an agonized rictus. He desperately needed to scream but his whole body was paralyzed by pain. His muscles refused to relax and as he awaited the final stroke cramps added to his anguish. She made him wait and wait. Beads of sweat broke out on his forehead and his shirt was plastered to his body, and then finally it came. This time it was lower, across the back of his left thigh, but the tip sought out his now flaccid penis with a wicked flick.

"ARRRRGGGGHhhh!"

"Do you think that constitutes a scream Mrs Cole?"

"That was most definitely a scream."

"Well in that case we'll just have to start all over again"

"NNNoooooo! No more! ..."

His breathing was laboured and he groaned with every breath. Clariss turned to Mrs Cole.

"It would appear that he is going to be tiresome. It will probably be for the best if we gag him before the next stage."

"Gag him?"

"Yes. Nothing elaborate. I was thinking, if you don't think me presumptuous, that I might use your underwear."

Karen Cole felt two things at once. On the one hand complete shock but on the other an excitement that sent her heart racing. The only problem was that her panties were completely sodden. She would never have admitted it, perhaps not even to herself, but watching Clariss Hardacre at work had given her the greatest sexual charge she had felt in years. She looked Clariss in the eye and in that moment she realised, with total certainty, that Clariss had known this all along, that Clariss had made the request in the knowledge that her panties would be soiled, that Clariss would be disappointed were if it any other way. Keeping her eyes on her mentor she reached under her skirt and shimmied her panties down her long legs and stepped out of them.

"And if you wouldn't mind ..."

Clariss pointed at Karen’s legs. Karen understood immediately and removed her self supporting stockings and then picked up her panties.

"What do I do now?"

"Pinch his nose and wait until he opens his mouth"

With great distaste Karen did as she was told.

"He's got his teeth gritted."

"That’s no problem. I'll use the cane. If he doesn't co-operate within ten seconds I'll flay his balls"

"Please ... Stop... You can't..!"

Clariss gave his balls a playful tap

"Okay .. Okay.."

His mouth opened and Karen pushed her bunched up panties inside. Seconds later they were bound in place with her navy blue stocking. Clariss handed her the cane.

"Perhaps you would like a go?"

His eyes widened and his head shook in his effort to be spared this new indignity.

Karen took the cane uncertainly and raised it slowly into the air.

Thwaaackk!

Her stroke lacked the finesse of Clariss’ but she made up for it with sheer brute strength. Thwaaacckk!

The second stroke had him screaming into the makeshift gag and Karen could not believe the thrill it gave her. She struck again and again, grunting with the effort.

Thwaacccckk! Thwaaccckk! Thwaaccckk! Thwaacckk!

When she had finished his buttocks were spotted with red and he was crying openly.

"I can't believe I enjoyed that so much"

Clariss took her hand.

"If you like I'll introduce you to some friends of mine. There is so much more to enjoy"

"I'm just a little disappointed that I can't use the cane as well as you do"

Clariss laughed.

"It will come to you. As a rule I can generally do much better than this. Its just that clothes can be such an encumbrance."

"Would you ... would you show me?"

"He's had his twelve ..."

"But you did say if he screamed it meant starting all over again."

"Yes I did didn't I."

Karen turned and, taking his balls in her hand, she squeezed as hard as she could. He held out for two or three seconds with his eyes tightly closed but then.

"NNNNaaaahhHHHHHH!!"

She let go and held out the cane to Clariss. Clariss slowly undid her blouse, dropped her shoulders and lett it fall to the floor. She used a hand to raise her hair from her neck and half turned her back to Karen.

"Would you ...?"

Karen reached forward and unfastened Clariss' bra and it too fell to the floor. As Clariss turned to face her Karen could not help herself.

"They're beautiful.."

Clariss smiled.

"Thank you"

Her breasts were full and heavy but there was no hint of sag. The excited nipples jutted proudly upwards and called to the hand. She took the cane and carefully adjusted her stance. When the cane came down Karen thought that it would cut the man in two. Her eyes were torn between the sway of Clariss' breasts and his agonized jolt. Clariss looked as though she was in a trance as she raised the cane and struck again.

"Thhwaaccckkk"

The mixture of sounds was of itself intoxicating. Clariss' muted grunt juxtaposed by the crisp sound of the cane and the muted agonized screams of her victim. The cane fell again but this time he could not respond. His body surrendered to unconsciousness.

"Will you let him go now?"

"He has to take the final three. He has to know there is no mercy."

"And would you give him more?"

"Under certain circumstances ..."

"If he had another erection for example."

"You catch on quickly..."

After ten minutes he returned slowly to consciousness. His whole body was crying out in pain and his eyes found it hard to focus. His brain fought to remember where he was and what had happened. Slowly, it began to come back to him and it was with dawning horror that he realized that he was still fastened securely to the evil whipping block. He raised his head and then had to shake it to clear the image, but still the scene seemed unreal. Seated in a chair not ten feet in front of him sat Clariss Hardacre her hands cupping and fondling the most spectacular pair of breasts he had ever seen in his life and there, kneeling between her legs, was a second heavenly body and he watched as the head of thick red hair bobbed back and forth as Karen applied her tongue and brought moans of delight from the headmistress from hell. He tried to close his mind to it but it was not possible, and, to his astonishment, despite all that had gone before, he felt his prick begin to harden ....

krr1957
krr1957
1,570 Followers
Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Doctor's Orders Pt. 01 A man gives up sex but his doctor has other ideas.in BDSM
Exploring Sexuality: A Pegging Husband is pegged by sister-in-law with wife's permission.in Anal
Easy First Date Girl uses strapon to peg a boy.in Anal
She Claimed Him Older dominant female claims her submissive male colleague.in BDSM
Cheryl's Passion Ch. 01 Cheryl decides she needs a mistress.in BDSM
More Stories