Mrs. Wintergreen's Rule of The Crop

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The HoD dishes out some discipline.
6.8k words
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Part 1 of the 9 part series

Updated 04/12/2024
Created 08/30/2023
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"Bugger, bugger, bugger, bollocks!"

Just turned nineteen, Louise Craven sat back in her seat in the tall office building on Fenchurch Street and swore under her breath. She looked at the message on her PC again and again.

"Report to Mrs. Wintergreen's office at eleven precisely."

Trevor looked over her shoulder and burst out laughing. He summoned Rachel and Billy to join in the fun.

"What's so bloody funny?"

"Guys. Louise has to see Mrs. Wintergreen! What a hoot!"

The attractive blonde turned in her three-wheeled roller seat and narrowed her eyes.

"So? It's just my first-year probation review, and she is the head of the department. No problem."

"Mr. Williams normally deals with those. If you have to go see HER, it must mean trub."

Billy put his hand over his mouth to suppress more giggles.

"Trub?"

"Trouble. That woman is a real bitch. Hates everyone."

"Yeah," agreed Trevor. "She's a tyrant."

"No, she's not." Rachel held up her hand. "She's a sadistic tyrant!"

"Right. I don't even know if she has teeth. Never seen her smile yet."

The other workers left the young secretary to ponder her fate as she slowly watched the clock tick away the minutes.

Louise needed this job. She had been fortunate to land the position and it had meant she and her boyfriend could afford to rent their first studio flat. If she were fired, it would probably mean she would have to move back in with her parents.

"Sod that. I'll just charm this Mrs. Wintergreen right out of her shoes."

x

At 10.55, Louise stood in the lady's room and checked her makeup. She fluffed up her buttery blonde wavy hair and smiled to herself. Luckily on this morning, she had chosen to wear her grey top that fit close to the body and had extra long sleeves. Also, her short-length high waist black skirt ended at the upper hip area. On her feet were her brand new nude heeled sandals with straps that wound around her lower calves and Achilles tendon.

"Hello?"

She opened the door of Mrs. Wintergreen's large office and peeked around the empty room. The reception area was small with a desk and sofa on the opposite side. A table separated the two and various outdated copies of Vogue and Cosmopolitan were strewn around on it. She sat on the sofa crossed her shapely pins and looked at her watch. Eleven o'clock. She was dead on time.

"Where is everybody?" she wondered as she sat in the odd silence.

Impatient and slightly bored, Louise went to the office and pushed the half-open door.

"Mrs. Wintergreen? Are you in here?"

The modest-sized room was sparsely furnished and had one big desk and a tall lamp by the very large window. Pictures of various cities adorned the wall and she studied each one in turn. She admired the view from the window and looked down on Fenchurch Street and watched the traffic. At that moment, her eyes were drawn to a half-open drawer in the desk.

"Oh, my!"

Something curious peeked out of the corner and she thought she recognised a horse riding crop. Her eyes went to the open door and saw no one so she pulled the top drawer out and reeled back in surprise. There, Louise found all types of erotic toys, vibrators, anal plugs, fur-lined handcuffs, and a black riding crop. Amid these outrageous devices, there were also several pairs of silk underwear and a pheasant feather. But it was the crop that caught her eye and she cautiously picked it up. It was an expensive, probably a hundred quid, black fleck crop of woven nylon and was about sixteen inches in length. The handle had wrapped leather and sported a big braided cap with a dimpled button. The keeper was also leather and was two inches wide.

"Oh my gosh. Mrs. Wintergreen seems to have some fetish interests."

"Is that so?"

Louise gasped and came out of her reverie as she was interrupted by a classy woman with flowing auburn hair. Dressed in a business-like manner she had a three-quarter length slim pencil fit dress in blue and white check, and a waist-high top with one button fastened just below the bust. Her navy bra was visible in the deep V of the low-cut look.

"Oh, shit! I'm sorry! I'm so sorry! I'm Louise by the way. Are you Mrs. Wintergreen?"

Without a word, the forty-one-year-old woman stared at her as she walked around and around the desk. She casually picked up the handcuffs and toyed with them as she paced the room. Louise ate humble pie as she demurred and hopped from one shoe to the other.

"This is not a good start Miss Craven. Snooping through private property, perhaps you lack discipline? Did you go to school? Do you know right from wrong?"

"Of course."

"Indeed. Maybe you need to be punished. Taught a lesson in fact."

We're not at school now, thought Louise who wondered where all this was leading. She found her eyes glued to the older woman's curvaceous form in the pencil-thin dress, her bare long legs, and her pouty red glossy lips.

"Discipline is an established practice I have adopted in my line of work. To be regulated. Directed if you will. From my way of thinking I think we can accommodate you in the agency. It seems to be effective."

Wintergreen looked down her nose at the nervous blonde with a sardonic grin. As she lectured, she paced the room, her navy stiletto shoes clicking on the hardwood floor.

"Now, I used to be a teacher at a private girl school in Kent. And I did NOT spare the rod. There are three types of discipline. One is preventive. Two, are supportive, and three are corrective. Which do you think I should pick with you?"

"Look, Mrs. Wintergreen. I just came here to have my yearly review. I wasn't expecting this at all. Maybe I should leave."

As she spoke, Louise remained rooted to the spot with a new feeling that overwhelmed her. In her young life, she had not had any sexual relations with females, and she was definitely not gay. Just bi-curious. She wondered what the woman had planned and the hesitation was etched on her face. The door slammed shut then and she jumped at the intrusion into her thoughts.

"It appears that you might like the crop. Perhaps I should use it, or maybe something bigger. I can show you ways of pleasure through pain you have never dreamed of."

Wintergreen passed her and rested the leather tongue of the crop on her upper right thigh. Louise shivered as it wiggled on her bare flesh a moment before it was removed. They were so close that their body heat was felt by the pair of them. Louise began to wilt under the stern and direct eye contact made by the other woman.

"You can?"

Wintergreen raised Louise's chin and gave her a knowing look.

"Oh, yes. And I know you want to try, am I right? You want, I want."

"Show...show me then."

"Are you certain? We can continue or I can stop, it's your choice. Yes? Then hold up your wrists."

Louise put her hands together and Wintergreen put the cuffs around her wrists and snapped them shut with an acute click. She tested the metal bracelets by tugging on the chain that joined them. They held tight. Part of Louise felt slightly scared but she could not deny the excitement between her thighs.

"All part of the service."

Mrs. Wintergreen made Louise face the desk and held her in place with her left hand. As she bent across the desk, her cuffed hands came together as if in prayer and Wintergreen used her right to pull the skimpy underwear down to her ankles. In this pose, Louise revealed a half-moon of bare white thigh and the businesswoman patted her behind with a certain affection as she studied the luscious curves of her bare bum. The skin was white and delicate and was a joyous sight and twin dimples were visible above the rounded cheeks.

"Look at these little panties, what a little slut you are. Stay perfectly still my dear."

Louise felt the hand replaced with the head of the crop which was swept down the exposed crack between cheeks, past the perineum, and down to the upturned base of her moist slit. She flattened the upper half of her body on the surface of the desk as her pussy was touched from behind.

"You appear to be somewhat aroused. That is a good sign."

Louise bit her lip and tucked in her elbows as she wiggled her posterior on the probing crop and then let out a shriek when she received the initial crack on her left cheek.

"WOW!"

There came four more staccato strokes delivered in rapid succession, two each on either globe. The crop swished through the air as it relayed its message and the beautifully shaped bottom of the young filly displayed a rosy glow that widened and deepened. Despite the stinging, Louise did not attempt to move from her undignified position and kept her enticing backside raised upward.

"How was that? I know it hurts, but it's a nice hurt, all warm and tingly, and it was exciting yes?"

Louise gulped. Too exciting! The woman soothed her burning rump and Louise admitted her smarting flesh had a sort of glow. Then she felt a warm palm strike her in a swift, flat arc and bounce back off her delectable derriere.

"OWW!"

She remained in position apart from throwing a few wriggles of her smarting rump which caused her panties to toss around her ankles. Mrs. Wintergreen scrutinised the five-fingered imprint that spread across both buttocks and raised the crop once more. She angled the plump and burning bottom of the girl so that it was higher than her head and directly in line for a prime whacking.

'Thwack! Thwack! Thwack!'

"Oh, fuck!"

Louise pressed her knees together and arched her back as the crop struck. So fast were the strokes that they seemed to overlap with earlier ones. She bore the brunt of the cracking smacks that rang out loudly and moved her hips in rhythm with the lesson. A flood of wetness betrayed her and Wintergreen ceased her ministrations and put her hand on the sublime curve of the ripe cheeks in front of her and then moved between her legs.

"So very wet, my dear Miss Craven."

One finger was dipped inside the moist labia and pushed in slowly. Then she brought the same digit to her lips and tasted the sweet nectar.

"Remember what I said? Pleasure through pain. Discipline and correction. You're coming along splendidly."

She tapped Louise on the shoulder and she stood up straight, her bum still reeling from the corporal punishment.

"Sometimes the seductress becomes the slave and the submissive the seductress as roles reverse."

As she spoke Mrs. Wintergreen discarded her top to reveal the navy bra that was evidently for attention-seeking rather than practical purposes. She unbuttoned her dress and pushed it down so that Louise could see her matching lacy blue panties. Just in underwear and stiletto heels, the tall woman cut a striking figure.

"The results are the same, it's all part of the same fantasy, the same discipline. It's all about the control."

The mature disciplinarian leaned back on the desk and kicked out her incredibly long legs. Her bottom settled against the edge and then she crooked a finger for Louise to approach. She complied and went to her knees where her head was level with the woman's thin panty line.

"Lick my pussy."

Louise lifted her cuffed hands and pushed the gusset aside and looked on a totally shaven quim, the outer lips puffy and the inner pink visible. Without hesitation, the young blonde darted out with her tongue and swiped at the offered folds. Wintergreen responded with a high pitch sigh as she quivered on her out-planted heels. Louise heard the woman moan as her tongue slowly started to slip in and out of the wet pussy in her face and Wintergreen's hips wiggled from side to side.

"Better, now give me some more tongue."

Louise inhaled her sex as she planted kisses on her inner thighs. Her nose bumped gently against the protruding clitoris as the inquisitive blonde flattened her tongue and brought it up from the bottom of the tantalising slit to just below the stiffening clit. The juices that soaked the woman's quim wet the tongue of Louise in a rewarding way and she eagerly lapped up all that was on offer. Mrs. Wintergreen humped against the nineteen-year-olds face as she was eaten and swept great handfuls of lustrous hair from her brow. Her gorgeous green eyes under narrow brows looked so innocent as she ate pussy.

"Yes, yes, like that."

Louise stepped up and bobbed on her haunches as she licked up and down in broad strokes, sliding perfectly over the unhooded clit as she reached the pinnacle of the pouting pussy.

"I gotta stand up."

Louise was feeling her legs ache and also rubbed her body to soothe the blows from the crop.

"Very well."

Mrs. Wintergreen came behind the quivering girl and pressed her body at her back. Her hands came up and caressed her boobs through her soft long-sleeved top and then dragged it downwards hard and helped the blonde step out of it.

"Let me see those tits."

Louise proudly thrust out her chest and showed off her breasts. She was in great shape with a slim figure, flat abs, lean legs, and sexy buns. The sensation of another female fondling her tits was a new one and Louise felt her stomach tighten and her nipples stiffen.

The department head felt up their weight in both hands and Louise closed her eyes to focus on the soft touch. A spiral pattern was painted with a fingertip on her left areola pulling away before contact with the nipple. The same was repeated on the right as Wintergreen came around to her front and hugged her tight so that both pairs of tits bumped together.

"Yes, these are your best assets."

Mrs. Wintergreen unclasped her bra and let it fall to the floor. The generous swell of her natural breasts were unveiled and Louise observed the hard nipples. Then she hooked her thumbs in the waistband of her panties and pulled them down over her rump as she bent at the waist and thrust out her backside.

"I so love being naked in female company."

Louise again had her boobs massaged and kneaded and had the hard nipples tweaked between her finger and thumb. They stumbled backward until one pinned the other to the edge of the desk and her sore rump was set on the cool wood. Her hips thus raised her fair-pubed pussy was displayed perfectly at the juncture of her upper thighs. Then a padded blindfold was produced and slipped over the innocent face of Louise.

"I don't want you to be able to see what I'm going to do next. It will heighten the senses. Just enjoy the show."

Louise pursed her lips as a hand widened her thighs and she placed her hands palms down on the top of the desk behind her. Seconds passed but it seemed simply ages before finally contact was made. Wintergreen brought the keeper down right on the sweet spot of her pussy with a backhand blow. Louise screamed and a tiny squirt of fluids spat out of her stirred cunt.

"FUCK!"

"Mmm, that good? Hmm? Feel nice?"

Several more pats came directly on her muff while she squirmed on her butt. Unable to see a thing her imagination ran wild and she turned her head from left to right as she awaited the next move.

"Mm-hmm! Stick that cute little pussy out for me, there's a dear."

Louise leaned back and raised her hips as she felt the crop trace out a line from her navel to her pussy opening then she shrieked from the pistol crack smack directly on her clit.

"OH!"

Wintergreen made three more slaps on the exact same spot and Louise came with a silent scream.

"Isn't that exciting? Let me lick you all up."

Wintergreen leaned in and reached between her open legs and pushed up inside her slit with her middle finger. Louise felt her knees buckle slightly as she was quickly frigged by the long digit. Her breathing became urgent as she bumped back into the desk edge. The finger was replaced by a tongue that ran around her puffy labia and then into her slit on up to her clit. Louise shivered in response as her tiny rosebud was flicked to stiffness. She sighed with delight as a hot mouth smothered her left nipple and sucked it to stiffness. Then her right nipple received the same treatment and she licked her lips in gratitude.

"Holy shit!"

The tongue left her muff and suddenly Louise reeled from two hefty taps on her hard nipples with the nylon braided cap. Swish, swish, swish. Each nipple changed to rosy peaks as she was given quick raps over and over. Her pussy wept juices and an intriguing trickle ran down her ass crack. Each stroke increased in intensity and Louise gave high-pitched squeals in reply.

"You're so wet, my dear."

"Uh, huh!" Mumbled the girl as she turned her head.

She heard a noise to her left and then a finger brushed her pussy.

"Yes, no need for lubrication today."

Louise felt a stiff object at her entrance and realised it must be a silicone dildo. She bit her lip and held onto the edge of the desk until her knuckles went white She sighed at the initial contact and inhaled deeply as it began to intrude inside her cunt. Then she felt a push and incredibly the entire sex toy was inside her all the way. It remained inserted and neither moved a muscle as Mrs. Wintergreen played a waiting game.

"Here."

Louise blinked as the blindfold was lifted and she looked into the grinning eyes of the talent agent. She lowered her gaze and made gaping motions with her mouth as she saw the strap-on toy sticking in her pussy. It was attached by straps to the woman's waist and hips. She watched the woman pull back out to within an inch before gasping as the eight-inch dildo thrust all the way up inside her again.

"Fuck this little slut! Let the slut take it all."

A hand reached out and held Louise by the shoulder as the silicone toy drove in and out. Louise was giddy with pleasure as she began to move in unison with the dildo, each entry thrust being met with a satisfied whimper. Her tits were caressed as she was fucked and her head snapped back as the strokes became more animated.

"Fuck, fuck, fuck!" she cried as she fast approached her second orgasm.

Mrs. Wintergreen sped up her gyrations with eyes half shut as she fucked the shit out of a delirious young girl. Their wet mounds met and their sodden pubic hair appeared somewhat darkened from their combined juices. Each slap of their loins brought them nearer and nearer to orgasm. Wintergreen's big tits jiggled from her pounding as the dildo kept on driving in and out.

"Are you close? Are you?"

"Yep!"

Wintergreen brought her arms under the other's thighs and lifted her bottom clear up from the desk. Louise was surprised by the woman's strength as she was pulled back over and over onto the eight-inch dildo. The relentless slap, slap, slap of their perspiring bodies on each other reverberated around the office. Louise began to rub her clit with the flat of her fingers as her hips were pulled up harder with each stroke of the false cock.

"Fuck you, gonna fuck you, fuck, fuck, fucking bitch with your big fucking tits, You want me to work for you? You fucking work for me, blond bitch with your big green eyes. Well, take this!"

Louise was tilted up even further so that the dildo was inside her cunt every inch of the way. Wintergreen's butt was a blur as her upper thighs smacked against the backs of the girl in one final big bang. Louise put more pressure on her clit and then she was coming with a hearty yell.

"Oh, YES!"

"Oh yes? You came, cunt? Fucking cunt!"

The mature female felt her own explosion in her pussy as she let the dildo slip out of the juicy quim and stuffed three fingers up her own. She jammed them in and savoured the welcome contractions.

"Fuck, I needed that. Well, Miss Craven. If you would like to retain your position I'll agree to new terms."

Mrs. Wintergreen walked naked around to the back of her desk, her peach of a butt rolling from left to right as her high heels clacked on the floor. She reached into her toy drawer and fished out a blue silicone anal plug which she waved in the air with a wink. Good gravy! Thought Louise as she picked up her things and left in a hurry.

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