Mrs. Wintergreen's Rule of The Crop Ch. 04

Jeremy Bates stood straight-backed and imperious as he inhaled through flared nostrils and contemplated his lot. All of six-three, with baby blue eyes and well-groomed hair, he always had an air of faux superiority about him. Well, normally. But, here he was now, butt naked and with his hands firmly cuffed behind his back.

"Marian."

"Jeremy."

She smiled as her gaze lowered to his groin, brazenly bared for her to leer at. His impressive dick jutted out at a jaunty angle as the blood surged all at once to his organ.

"Have you been a good boy, Jeremy?"

"No, ma'am. I've been thoroughly naughty, and deserve to be chastised."

"Glad to hear it."

His aching erection pointed at her, the tip shiny and swollen. He had not felt this exposed and vulnerable in a long time. He had submitted to the Dom before, but this promised to be new and unexpected. Mrs. Wintergreen sat back in her leather upholstered chair in her plush office at 20 Fenchurch Street and placed the stiletto heels of her knee-high black boots up on the mahogany desk.

She idly fidgeted with the reports and mail that sat next to her PC with her heel. She had daydreamed of the close of business all of that busy day and had entertained illicit thoughts of the little affair she had arranged for her hot CEO. She pressed her head back into the soft cushioned headrest of her chair and stroked her crotch under her prim-looking dress. Bates craned his neck in an attempt to see her plump mound but to no avail.

"I'm so hot down here I almost set my fingers alight." 

The cuffed man gulped and his hard dick twitched with yearning as he watched the hot forty-something play with herself. For a good minute, the willowy brunette massaged her muff, delighting in the exquisite tingling that ran down to her toes, and the wicked tease she gave her boss. Eventually, she sighed and stood up. She walked around the desk and casually unzipped her dress from behind. As it fluttered to the lush carpet, Bates saw that underneath her business-like attire, the wanton vixen wore an exotic halter neck and backless leotard in gold latex. The thong section between her upper thighs accentuated her mound of Venus perfectly. The outfit clung to every delicious curve of her slender body, especially her breasts and rear end.

"See something you like?" she queried as she rocked gently back and forth on her sharp heels.

"Yes. I see a lot that I like."

She circled him slowly, letting the man admire her body from every angle. Her legs were long and subtly toned. Her bosom heaved as she inhaled through flared nostrils.

"Is that so? Well. As you are aware, discipline is an established factor I have adopted in the everyday running of the business. I have high expectations and aspire to only the best of those. Including those persons at the very top. Do you understand?"

Tall, gorgeous, and very dominant, Mrs. Wintergreen had worked hard to get where she was and demanded the utmost respect as a result. Her fierce gaze and high cheekbones thoroughly captivated those who saw her in the flesh. Her five-foot-ten frame stretched her classic hourglass figure into sleekness and imbued her with the superiority worthy of her position.

When the board of directors named her the head of the department, she felt that she had arrived at the pinnacle of her career thus far. Marian grabbed onto Jeremy's testicles and yanked them up in a harsh manner. He went up on tiptoe and threw his chest out. His instinctive reaction to avert the humiliation was thwarted by his hands being secured behind his back.

"Yes," he answered meekly and in a high-pitched tone.

"Again. Louder."

"YES!"

Marian came nose to nose with the man and twisted his balls in her tight fist. When he had put in an appearance at the office block, he had been stunned to listen to her mock and denigrate him after his involvement in the collapse of a lucrative business deal worth millions. As he unashamedly shared the woman's passion for all things physical, he willingly let her seduce him and strip him of all clothing. Having been intoxicated by her erotic power, Bates craved the rough punishment he endured for their pleasure.

"Your presentation and conduct during the Manchester amalgamation meetings was pathetic and potentially damaging to the company. With key clients poised to sign on the dotted line for last Friday afternoon, your oratory and rhetoric were deplorable. However, all is not lost. The Bank and Savings and Trust have offered a three-way deal that sits on my desk at this very moment. We may still salvage something from this debacle."

Bates nodded. He had indeed fouled things up and took full responsibility for his misgivings. He looked at the leggy brunette and curled his toes. He was fully aroused, yet at the same time, he was at the mercy of this domineering woman. And he loved it!

"The board of directors may be forgiving, but I have taken it upon myself to mete out some form of corrective retribution. There are three types of discipline, in my humble opinion. Preventive, supportive, and corrective. I think that we need to revise the third."

Her attractive face also projected a cruel beauty, the countenance of someone born to dominate and humiliate. Bates hissed through gritted teeth as she gripped his boner and jerked him off. The sensual motions of her hand were exquisite and for a split second, he thought he would explode.

"Get down on your knees."

It wasn't easy with both hands cuffed behind him, but he managed to get down before her. Her left hand gripped the back of his head, and her right moved the thong section of her latex leotard to one side of her mons.

"Kiss it."

Bates did as he was ordered, and noted the moisture that glistened on her bald lips. The darker skin of her outer labia was totally smooth and shiny.  His prick hardened even more.  His nostrils flared as he inhaled the musk of her quim. He then licked her, teasing her outer folds with sweeping passes. He kissed her swollen clitoris and flicked out with his tongue, the result of which made the auburn-haired vixen moan loudly. She began to buck against his face, maintaining maximum contact whilst swiveling her hips. She took his head in her hands and firmly pressed his face into her snatch. Arching her back, she rubbed her crotch against him, thereby coating his lips and mouth with her juices.

His aching cock jumped in response, even without directly being touched. With her head tilted up, the latex-clad dominatrix pressed on his ears and trapped his wriggling tongue between her cunt entrance and throbbing clit. The sublime vibrations made her wetter with each moment. Her shaven pussy was perfect! As her hips were gyrating, he concentrated solely on her tiny nub.

"Enough! You naughty man."

She dragged him up onto his feet by the hair on top of his slumped head, and the tip of his cock poked through her upper thighs and brushed her pussy mound. She chose to go down on her haunches then, and her pointed tongue flicked out as she traced a line from his chest down his sternum to his navel. She teased the button as she held his flanks, but avoided his cock. His hose wagged at her like a puppy tail demanding attention, but she just trailed her fingers down the junction of his thigh to where his balls hung. He hummed between pursed lips but she left him in limbo. Bates was extremely turned on and wanted to jump her right there and then and start fucking.

"Bend over the desk. And say nothing."

Bates obeyed and exhaled deeply as the handcuffs were removed.

"Reach out and grip the far side of the desk and close your legs."

How quickly the tables had turned. It had been merely two months since Bates had watched the woman in the very same stance as he now. It had been he with the riding crop in his fist, meting out firm cracks upon her rounded backside. He recalled her dark tresses of loose curls whipping around as she tossed her head back and forth. He had spanked her soundly over and over, while her cries of pain and pleasure made his dick throb. The tall assertive figure circled the desk and used her favourite crop to smack her left palm like a metronome. The atmosphere was heavy with trepidation on his part as he became undisputedly ensnared in the woman's ascendency. To be perfectly frank, she had him by the balls! He was hers. To use, to castigate.

"Ready?"

"Yes."

"Good."

To further his torment. Mrs. Wintergreen tapped his rear end lightly, moving to the backs of his thighs. Softish raps at first, then faster and firmer. Then, she raised her right arm, and without warning, brought the business end of the crop down on his quivering bare backside with an almighty crack. Bates yelped. More with the surprise than any pain.

Mrs. Wintergreen smacked his bum again. And then again. The sound of leather on flesh was stark. A veritable detonation in fact. The tall minx took a second to scrutinise the fellow's glowing buttocks and smiled. She gloated over his pale display of tender white cheeks, and she shut her thighs and squeezed her moist cunny through the latex. She smacked the crop on his defenseless cheeks in a series of rapid strokes. His smooth skin now displayed several scarlet stripes that crisscrossed. His knuckles had turned white as he kept hold of the far edge of the desk.

With his head down on the mahogany surface, he failed to see his castigator wriggle out of her leotard and stand behind him stark bollock naked, save for her stiletto-heeled boots. He felt her soft body and pliant breasts press into his back. He squirmed and wiggled his bottom at her, but this was rewarded by a couple of hearty cracks of the crop.

"No!"

Again, he was spanked hard, and his groans and squeals filled the office, along with that erotic sound of harsh retribution on his sorry posterior.

"Do not move your sorry bottom unless I permit it."

Bates knew he would have to use all his will to avoid kicking his legs. He bent over and grasped the far edge of the table and concentrated.

WHACK!

Mrs. Wintergreen delivered ten firm cracks of the crop across his backside about three seconds apart. He twisted his hips involuntarily, and desperately wanted to widen his legs.

WHACK!

He dragged his nails across the desk and dry-humped air as his arousal became pronounced. His calves trembled in an attempt to keep his feet on the carpet. The now naked vixen waited a few moments and stared hard at her ruthless handiwork. His naked submission delighted her to no end. Quivering with satisfaction, she settled back in her chair.

"Good boy. You may lick my pussy."

Bates shook his head to clear his thoughts and cupped his heated cheeks in both hands. He knelt before her and rubbed the palms of his hand up and down her upper thigh as he stared at her mound. He loved the feel of the smooth pale skin of her legs as he moved in and pointed his tongue at her cunt. As he swiped up and down in her snatch, he felt the crop gently smoothing out his rounded buttocks.

"Do you have a sore bottom, Jeremy? Don't answer. It's a rhetorical question. Keep tonguing me."

She thrust upward from the seat and smothered his mouth with her smooth mons. He made her wetter with each moment. Her legs trapped his head there in willing frolicsome. She was taking what she wanted from him whilst making it clear who was in control. The fingers of her left hand became entangled in his hair as her right tapped his rear end lightly with the crop.

"Get in there," she commanded. "Get your tongue right inside me." 

He greedily lapped at her pink bud, and her hand grasped the hair on the back of his head and she bucked and twitched on her bottom. His head nodded as if he were a puppy searching for scraps. He used his freed-up hands to stroke the supple, creamy white part of her legs uncovered by her leather boots. Marian grinned as she looked down at the CEO on his hands and knees at her feet. His rear end bobbed up and down as he fucked the air with his sturdy looking eight incher. The more he tongue-lashed the tall and haughty minx, the more he desired to fuck her. But she still had plans for more corrective discipline.

"Wait there, and do not move."

Bates watched the booted and naked stunner totter over to one corner and saw her drag out a black object. It appeared to be a cross between a bench and a chair. It had foot stirrups at one end, and hanging handcuffs at the other.

"I'm going to strap you to that bench, and you are not to make a fuss. If you have an objection to this, we may have a problem."

"It's fine," he said with an edge of nervousness. This was what they both wanted, wasn't it?

He sat back in the seat and she busied herself with cuffing his wrists above his head. Then, his right leg was lifted, and his foot was placed in the stirrups. She secured his left foot and he now resembled an upturned tortoise. His asshole, balls, and hard dick were all on lewd display as he swung gently in the bondage chair.

Her fingers caressed his perineum and his cock throbbed maddingly on his belly. Again, she wielded the infamous riding crop in one hand and too careful aim. She stood side-on and administered stinging blows to his upturned buttocks. Bates groaned feverishly from the bone-jarring strikes, and he jiggled in his restraints.

"Hold that thought, my man."

Marian vanished for a couple of minutes and then returned wearing a black harness with straps about her upper thighs and waist. Protruding from the centerpiece was a six-inch long dildo, with tiny nubs on the shaft, and realistic-looking testicles at the base. His eyes widened at the sight of the large phallus that bobbed obscenely in front of her.

"Oh, fuck!"

Her hand reached out to the back of his head, her slender fingers entwining in his hair as she guided him to her crotch.

"Go on and suck it."

His mouth fell open as she demanded him to suck the dildo. Even as she guided it to his face, he welcomed the large flared head against his lips. He stuck his neck out and took the bulbous head into his mouth. He obediently sucked on the large cock as Marian gently bucked her hips.

"Don't just suck on the head. Take more."

His eyes watered as the thing jammed into his gaping mouth. His lips clamped tightly around the thick shaft as he went through the motions. The brunette tease smiled to herself as she looked down at the man as he sucked dutifully on the dildo.

"Good man. That's more like it. Suck that cock, Jeremy."

Mrs. Wintergreen fucked his mouth some more and then pulled back. His cheeks flushed a bright red as he inhaled through flared nostrils.

"Now," she said as she squeezed a tube of lubrication into his nether hole. "I'm going to fuck the shit out of you with this, and then you're going to do the same to me."

The lewd sound of more lube being applied to the thick shaft of the sex toy was acute as Marian coated the thing liberally. The entire dildo was dripping with sticky goo. Both of them looked down at his battered rump as she rubbed the fake cock up and down his lubed poop chute. The bondage seat provided the perfect height for Marian to fuck Bates.

"Good lord, Jeremy. I didn't realise what a big behind you have."

Bates closed his eyes, his humiliation growing with each comment she made. Still, he could not ignore the growing feeling of excitement as her fingers caressed his balls. She pulled back and then pressed up with just the right angle to nudge his hole open. His feet waved on either side of her as he felt her push upwards with her hips. His body tensed up when he felt the initial pressure against his bum hole. As she slowly penetrated his anus with the sex toy, she reached in and firmly gripped his rock-hard cock.

Slowly but surely, Bates experienced a widening of his hole until the top of the dildo met his sphincter. Her tits bounced as Marian continued forward in a steady motion as she slid her strap-on into him. Her hips met his cheeks as she began a rhythmic back-and-forth rut. The pressure was slow but insistent. The large tip of the phallus pressed and pushed until it broke past his sphincter.

"I know you have never done this before, and definitely not with a man. But tonight, you are my bitch!"

He hissed aloud and he felt sweat burn his eyes as his asshole was unceremoniously plundered. Marian dug her toes in and jammed her strap-on into him as she began to buck back and forth. She leaned forward so that her stomach met his upside-down cheeks. The sensations of a cock, even one of silicone, sliding in and out of his shitter aroused him tenfold.

"Oh, yes! Oh, yes!" she cried as she slammed into him harder.

It was a mixture of intense pain and increasing pleasure for Bates. His hole felt sore, but he didn't want this sensation to stop. Marian continued thrusting all the way in and out. He wanted to jerk his twitching but with his hands tied, he was truly thwarted. As she fucked him, she rocked backward and forwards as the dildo became buried in his anus.

"Please. Please, Marian. My cock is going to explode!"

"Are you wimping out on me, Jeremy?"

With a pout, she pulled out with a sticky pop. The dildo bobbed in front of her as she looked at his big dick. Starved for attention, his organ looked menacing and needy. She could see the pronounced veins running the length of his shaft. monster cock. She stepped out of the strap-on harness and stroked her very wet muff. Coming round to his left side, she pressed her scarlet lips to the blunt end and let him pop inside her mouth.

"Ooooo, heaven!"

Realizing her chastisement had served its purposes, the horny hussy started to suck on the angry-looking hose with enthusiasm. She had always liked sucking Jeremy's fine organ and she slobbered and drooled audibly as her cunt dripped down her left inner thigh. Bates went along for the ride. Not much choice really, as he hung in the bondage apparatus.

"When I get out of this, I'm going to fuck your brains out."

"Promises promises."

Marian did not protest as she freed up the man. Bates sighed and flexed his muscles and stretched. Their eyes met, and then they studied each other's sex. His cock jutted out at her with a dark purple crown, and her bald muff glistened with pussy juice under the harsh lighting of the office. Her thighs were slick as well, and they slid together in an erotic fashion.

"I may not be able to sit down for days, you bitch!"

Marian smiled and spread her hands. She reared back when he grabbed a handful of her hair and brought her face to his turgid erection. He pressed his bell end against her lips, waiting for her to open them. When she did, he jammed his knob directly into her mouth. With a snarl and a grin, he face fucked her hard. Still grasping a handful of her hair, Bates wagged her head to and fro, which made her gurgle and dribble on his length. With his rock-hard tool invading her mouth and throat, Marian's eyes watered as she choked on the massive.

Now that he had turned the tables, the CEO rudely spun her around and bent her over the mahogany desk. He smacked each of her pale white nates and widened her legs with his right. He held her face to the surface of the desk with his left hand as he guided his length to her cunt from behind.

"Jeremy, oh!"

He drove all the way up and Marian whimpered in delight as he penetrated her to the hilt. Bates wasted no time as he gave her his all. He slammed the full length of his aching cock into her cunt, pulling back out almost all the way before ramming back in.

"How does that feel, cunt? Liking my big cock fucking your wet cunt?"

"Uh, huh!" she mumbles as he kept her face side on the desk.

Bates smiled triumphantly as he plowed in and out of the grateful woman. Her pussy was well-oiled and his fat log slid in and out with ease. He shoved every inch into her until he was slamming into her rear end with loud slaps. He reached under her with his left hand and began to strum her clit as he fucked her wildly. The stimulation was welcome and Mara rose up on the toes of her stiletto heeled boots. With a roar, Bates pulled back and let Marian crumple to the carpet.