1. PRELUDE
At dawn, Allan Knawtee struggled to wake up after a long and fitful night. As always, he slept naked on hardwood under his threadbare blanket. Jessica, his wife of 25 years, slept comfortably between satin sheets under a plush comforter in the queen-size bed above him. His wrists and ankles were cuffed, hands behind his back, with both sets of cuffs linked to a ring on his stainless steel chastity cage. His sleep was always fitful, but exhaustion is soporific.
He roused himself, rolled over, and climbed awkwardly up onto the foot of the bed, lifting the edge of the covers with his teeth. It felt so nice to clamber into her warm nest, to smell her feminine presence. Allan felt a wave of devotion as he slid up to seek her curves.
Wrapped in the soft covers, drifting softly in her dream, Jessica felt the bed move under her. Holding on to sleep, she drowsed as she felt Allan slide under the sheet. Rolling onto her tummy, she stretched drowsily and spread her legs. Pushing in the pitch darkness with his face, he slithered upward between her thighs and sought her tight pucker. Probing with his nose and lips, he found the target and began his morning worship in earnest.
Jessica had always loved rimming. Not just the asymmetric power dynamic, but the exquisite physical sensation of having a warm wet tongue probing and licking the sensitive tissue, the sensuous slippery slather of attention to her desire. And so she had developed this lovely morning ritual, starting each day with prolonged anal worship. It wasn’t about sex. It was just so nice to relax and drift slowly into consciousness with that warm wet tongue lapping away in her ass.
She scooched back against his face, spreading her thighs and arching her back. Most days she was content with 20 or 30 minutes of gentle licking and sucking before sending him away to make breakfast. On other mornings the delight of the anal tongue bath aroused her and she relaxed into some sexy pussy eating. Sometimes she would roll over, but it was even better to flip him onto his back so that she could kneel up over him, grinding onto his face for a few hot orgasms before breakfast.
This morning, she tired of his attentions after awhile and pushed Allan away. She unlocked his cuffs and sent him to make coffee. After her breakfast, she was ready for a nice hot shower.
Jessica was planning a fun activity for that evening and found herself a bit distracted.
2. AT THE OFFICE
Later that morning, Allan was sitting at his desk stressing out. He had an important presentation to make that afternoon, and he was dreading it. For 20 years, he had worked hard to climb the corporate ladder, rising to Assistant Vice President of Accounting. He earned a decent though not spectacular salary and had a lot of responsibility. He supervised a large and talented staff, he got his work done, he was valuable to the company, and he knew it.
Suddenly, Allan recalled a detail he really needed to add his presentation. He pushed the intercom button to ring his secretary again. She was busy preparing the report in his outer office and rolled her eyes with annoyance at the interruption.
Besides being crisply efficient, Claire Haughty was beautiful. In her late 20’s, tall and slim with long legs and a high firm bust, she dressed professionally, but her tight skirts and blouses always highlighted her stunning figure. Her red hair fell in waves around her lovely face, and her green eyes sparkled. He was always mindful of the professional boundary between them, but he couldn’t help being struck by Claire’s loveliness.
Claire had been working for Allan for two years, and she was pretty fed up. The pay was good, and she knew she might have a good chance to advance in the company, so she put up with her boss’s piggish sexism. He often asked her to do menial tasks like fetch coffee or get his mail. He was constantly ogling her when he didn’t think she was looking, and he frequently called her into his office on flimsy pretenses. She was proud of her appearance, but her boss was older than her own father! At least he had kept his hands to himself so far.
She opened the door to Allan’s office and poked her head in.
“Yes Sir?” she responded politely, for the 100th time that day so far.
“Come in here. I need you to prepare some more figures for this afternoon.” he told her.
Allan explained the extra spreadsheets that she’d need to make and reminded her of the 3 PM deadline. His eyes drifted down to Claire’s lovely chest. As always, she pretended not to notice. She turned to leave again. Allan knew that his wife would be furious at the way he stared at the sexy young woman. But Jessica wasn’t here, and Claire couldn’t very well do anything about it anyway.
“Oh, and make me some coffee!” he called out after her. She kept walking, cursing him under her breath.
Allan sighed as he watched Claire’s perfect backside swaying under the tight skirt. He would never tire of looking at her. Even back when he’d been young and single, women like Claire had always been out of his league and he’d known it. He had been socially awkward and even intimidated by pretty girls as a youth, and he was painfully aware that he mustn’t even let Claire catch him staring at her. Yet he couldn’t resist running his eyes along her departing thighs as they swished beneath the hem of her short skirt.
He felt his long-neglected cock swell inside its merciless cage. He’d been wearing the cage for years, since it had been custom-fitted to his cock and balls. He had long since grown accustomed to the inescapable confinement and hardly even noticed the physical discomfort any more. It had been nearly six months since Jessica had unlocked and milked him, though she teased him mercilessly during his weekly cleanings. The pent-up sexual desire sometimes made his penis stiffen uncontrollably inside the steel, which was painful. He squirmed behind his desk as he watched Claire close the door to his outer office.
Unfortunately, the little bit of self-regard Allan was able to extract from his work was constantly challenged by his boss Linda Beech, who never seemed satisfied with his performance. She had been Vice President of Accounting for over 10 years, and it seemed unlikely that Allan would ever be promoted again as long as she occupied the position.
Allan didn’t know what he had done to annoy her, but it was clear that Linda had it in for him. Nothing he did ever seemed to be good enough for her. Even when he succeeded, she always found something to complain about. He often wished she’d get transferred to a different city, and he found himself trying to calculate how long it would be until she retired, and he was rid of her. Hopefully he would still have some good years with the company after she left.
At 3 PM, Allan picked up the papers from his sexy secretary and marched to his boss’s corner office. He adjusted his tie and cleared his throat, then walked in and asked her secretary to announce him. He could feel the anxiety roiling his belly.
Linda was at least 10 years Allan’s senior and seemed to wear a perpetual frown. Since her husband had died years before, she had let her appearance go. She was obese, with big round glasses that had been out of style since the 90s. Her limp hair was a nondescript light brown color, almost certainly covering her gray. Her outfits were loose and baggy, not very good at hiding her bulk. Her large breasts sagged low and swelled over her even larger belly. Allan couldn’t help but being put off by her appearance any more than he could help being desperately attracted to his sexy off-limits (and half-his-age) secretary.
“Well, what have you got for me,” Linda snapped.
As usual, she didn’t even get up from her desk while he made his presentation. He had to stand awkwardly and shuffle through the papers he was carrying.
Allan was perspiring nervously. He knew the numbers were not as good as last year’s. He fumbled through the charts and graphs, and she was clearly unhappy with his work. She clucked with annoyance as he continued to present the numbers in the best light he could.
“Is that all?” she asked when he had finished.
“Yes, Ma’am,” he replied. “I know we’ve missed some of the targets, but I think we’re on track for a better result next quarter.” Allan could feel himself blushing as he sensed her frustration with him.
“You think?” she sneered. “Well this is just unacceptable! If you can’t turn this around by June, I’ll have to find somebody who can.”
“Yes, Ma’am. I understand,” he mumbled. Then he shuffled out of her office.
3. PREPARING TO SERVE
Driving home, Allan went over the difficult meeting in his head. If he didn’t bring home a bonus this year, his wife was going to be very unhappy with him. He knew she had her monthly book group coming over that night, and he cursed the heavy traffic. He really needed to get home in time to prepare!
He pulled into the garage and walked into the kitchen.
Jessica was in the media room, watching a huge television. She was dressed in jeans and a long-sleeved pullover. Her shoulder-length hair was brown and straight. At 45, she had never worked outside the home – Allan earned all the money she needed. She heard him come in.
“Get in here,” she barked.
“Yes Dear,” Allan replied. He walked quickly through the kitchen and joined her. “Down,” she said simply.
Allan dropped to his knees on the floor in front of her. Jessica leaned over and grabbed him by the tie, jerking his head toward her as she sat comfortably. He put his hands down to regain his balance.
“You’re late,” she said. “My book group is coming over tonight, in case you’d forgotten.”
“I know Dear,” he replied. “I’ll get ready right away.”
“Clean up that mess in the kitchen,” she ordered him. “And then make some hors d’oeuvres.”
She pulled him closer, and he felt the tie constrict his airflow.
“You’ll be serving us this evening,” she said. “And you’d better be on your best behavior if you know what’s good for you!”
She smiled at him. Allan was worried: he didn’t like the sound of this! He always served snacks and drinks for her friends, but she seemed to have some kind of mischief up her sleeve.
Returning to the kitchen, Allan took off his jacket, loosened his tie, and rolled up his sleeves. He washed the dishes, scrubbed the countertops, and cleaned the stove. Then he swept and mopped the floor. He could still hear the TV in the other room.
Finally, Allan put together a nice tray of cheeses, sliced meats, fruit, olives, and nuts. He was ready for Jessica’s guests.
4. THE BOOK GROUP
The doorbell rang, and Allan walked briskly to answer it. Their neighbor Jane stepped in and he greeted her politely.
Jane was in her mid-50’s, fairly attractive with big curly hair that had gone prematurely gray. Jane had a habit of talking about herself incessantly and not letting him get a word in edgewise. Allan thought she was kind of annoying, but she was his wife’s best friend.
As usual, Jane started talking about her week, her dog, her health concerns, and her friends. Allan held his tongue. It wouldn’t have done him any good to try to engage in an actual conversation with Jane anyway, so he just nodded politely and said “uh-huh” at what seemed like the right points in her monologue.
As Jane burbled on, Allan took her coat and escorted her into the living room where Jessica was waiting. The two ladies began to chat animatedly while he went to the kitchen to fetch the refreshments.
After he’d set out the hors d’oeuvres, Allan poured Jane and Jessica each a nice glass of red wine. Then the doorbell rang again.
When Allan opened the door, he did a double take. Standing there in his entryway were his boss Linda and his secretary Claire from the office! For a second, he stood there with his mouth open. Neither of them had ever been to his home before. They were not likely to be friends, as they were very different in age and social station. Allan’s brain just couldn’t register why they might call at his home.
“Come in, come in!” Jessica appeared behind him. “Allan, welcome our guests. They’ve just joined our book group.”
Still puzzled, Allan took their coats and led them into the living room to join the others. Once Linda and Claire were comfortable, he poured them each some wine. The bottle was almost empty, so he retrieved and opened another and left it on the coffee table for them. In a moment Jessica shooed him out of the room.
“Off you go now,” she said. “Leave us alone to talk about our book!”
Allan went back to the kitchen, where he prepared a light supper for himself while the ladies laughed and chatted. He could barely believe that Jessica had invited his coworkers – how did she even know them? He had no idea what kinds of books they might be reading, and he didn’t care. He did his own dishes and then browsed the web on his laptop for a while.
After about half an hour, Jessica called him in to bring another bottle of wine. The ladies’ laughter seemed to become more raucous. Allan walked back into the living room with some more snacks and uncorked a fresh bottle of wine.
Jessica was sitting with her legs crossed on the couch next to their chatty neighbor Jane. As Allan politely poured Jessica yet another glass, he was acutely aware of his grumpy boss and his very attractive secretary watching him. They giggled together as they watched him act like a waiter in his own home.
“Top mine up too,” Jane told him.
As Allan leaned over to take the half-empty glass Jane offered to him, Allan felt Jessica’s hand push hard on the middle of his back. “Better watch out!” she said, as she uncrossed her leg. With a swift motion she simultaneously pushed him forward and swept his shins backward.
A number of things happened at once. As he fell, Allan struggled to keep the bottle upright. He tumbled forward across Jessica’s lap and put his free hand out to break his fall. Unfortunately, he fell against Jane’s outstretched arm, knocking her wine glass across her chest. The dark red wine splashed across her light blue blouse, and her face registered shock and surprise.
“UGH! How dare you?” Jane shouted, jumping up and trying to shake the wine off the fabric.
Grabbing a bunch of napkins, she began wiping up the mess as best she could, but the stain was clearly going to be indelible. “Oh my God,” she cried, “you’ve ruined my blouse!”
“Oh God I’m so sorry!” Allan moaned. He looked at Jessica and noticed that her sneer had hardened into an angry glare.
“Shut up, you clumsy oaf!” she growled at him. The tipsy ladies turned to look at her. The sudden spill had interrupted their festive mood, and now they sensed something new was about to happen.
Jessica grabbed Allan by the belt buckle and pulled him sharply around to face her. “Hands on your head!” she ordered.
Allan felt the blood rise to his cheeks. Out of habit, he immediately complied, placing his hands at the back of his head and locking his fingers.
Behind him, he heard Linda laugh derisively. “Looks like you’re in big trouble now,” she taunted him.
Jessica began to open Allan’s belt buckle. His hands flew down.
“NOOO! Please not in front of them!” he begged.
Jessica slapped his hands away, hard.
“Get back in position! You know the rules!”
Allan closed his eyes and placed his hands back on his head. He knew he would never live this moment down.
The ladies all leaned forward toward Allan as Jessica opened his belt, then unzipped his pants.
Allan was completely powerless to do anything. He stood there in shock as Jessica yanked his pants and underwear down below his knees in one swift motion.
It was bad enough that his wife had made him assume the punishment position in front of her friends. Worse that she had included his boss and secretary! And then that she had bared him for all to see.
But worst of all, standing there surrounded by a circle of half-drunk women, Allan’s cock and balls were locked tightly into a gleaming stainless steel chastity cage! Jessica smiled broadly as all the other ladies gasped in surprise and confusion.
“Oh my God, what’s that on his dick?” Jane asked.
“I keep it locked up, so he can’t play with himself,” Jessica laughed. “He hasn’t had any action for over six months!”
“Ooohh, it’s a chastity cage!” Claire exclaimed. Perhaps she had seen one of these diabolical items before.
Allan’s knees were weak and he felt dizzy, knowing that he could never face these women again. And yet face them he would, day after day at the office and in the neighborhood.
Jessica grabbed Allan and quickly stripped off all his clothes. The ladies laughed as he struggled, but he knew better than to resist Jessica when he was being punished. From neck to thighs, Allan was almost completely hairless. Jessica had insisted that he have his body hair surgically removed years before. The steel chastity cage glinted in the light against his bare skin.
“Let me see that!” Allan’s boss Linda demanded.
Jessica wrenched Allan’s elbows behind his back and forced him to his knees in front of his boss. The ladies all leaned in to look closely.
Linda reached out and grabbed Allan by the balls.
“You’d better treat your boss with more respect from now on, you little twerp!” Jessica sneered.
“How does that feel?” Linda said, crushing his captive balls in her big hand.
“Owwww! It hurts,” Allan cried, with tears running down his face.
“Wow, you’ve really got him by the balls now, Ms Beech,” laughed the sexy Claire.
“Squeeze harder,” shouted Jane, thinking of her ruined blouse. “He deserves it!”
Jessica grabbed Allan by the ear and pulled him up off the floor. She tossed him roughly over her lap. His caged cock slipped between her blue-jean-clad thighs and his face flopped around on Jane’s lap.
Jessica began spanking Allan’s upturned ass with fast hard slaps. The trauma of his humiliation and the pain in his balls was quickly added to the burning in his bottom, and he began to cry and sob.
“What do you say now, you little creep?” she shouted at him as she blistered his buns.
“Please … I’m so S-S-SORRY Ma’am!” he wailed. His legs kicked and he bucked on her lap. Linda and Claire could see his caged balls bouncing and his puckered anus opening and closing as his legs scissored in his distress. Besides the sharp pain, he felt deep shame as he showed his coworkers everything he had.
“Hey, let me have a go,” Jane suggested. “He spilled my wine all over me!”
“OK, OK,” Jessica laughed. “Let’s all punish him.” Opening a drawer, she handed a heavy oaken paddle to Jane.
She pushed Allan to the floor and demanded that he stand up. Jane grabbed him by the elbows and held him still. Jessica produced a tiny key and unlocked the gleaming chastity cage.
“His naughty little dick has been locked up in there since Halloween,” she told the fascinated ladies. “He used to be such a nasty masturbator! Now we only let it out for special occasions.”
“Yuck!” Claire exclaimed. “How do you keep it clean?”
“Oh he has to wash it really well every day in the shower,” Jessica explained. “I inspect him to be sure it’s clean and sanitary.”
“You mean the cage never comes off?” asked Jane?
“I tie him down once a week and take it off,” Jessica answered. “Then I wash and disinfect it to make extra sure. It’s great fun because he always gets a stiffy from the soapy washcloth. Lately I’ve had to pack it in ice to get it back into the cage!”
All the ladies found the image of Allan’s weekly washing to be hilarious.
Jessica slid the steel cage off Allan’s dick, and yanked the retaining ring off of his hairless balls.
Sure enough, his cock began to swell immediately. It had been imprisoned so long that the slightest stimulation was all it took for physiology to take over. Jessica pushed Allan over the coffee table, and then sat on the couch. She grabbed his head and pulled him down so that his face was buried in her crotch. The position forced his sore red ass up high in the air. The ladies gathered round the obscene spectacle.
Ms. Beech pushed Allan’s legs far apart until his knees were at the corners of the coffee table. The ladies laughed and pointed at his humiliating display.
Jane swung the wooden paddle back and then down H A R D against his upturned flesh – WHAP! He nearly collapsed from the force of the blow, but Jessica warned him to hold the position. He screamed and sobbed into her crotch as jane paddled his ass over and over. The other ladies laughed and cheered her on.
WHAP WHAP WHAP! The paddle slapped into his rump again and again. His cock swelled up hard and a small drizzle of precum emerged from the head as it bounced back and forth with the force of the blows.
“His cock is drooling – I think he LIKES this,” yelled Linda.
“Wow, I want to paddle him too,” said Claire excitedly.
“Sure, let’s ALL paddle him until he cums,” Jessica laughed as Allan’s tears drenched her lap.
The ladies took turns paddling the poor miscreant until his ass was a mass of beet red. Allan cried and cried, but he knew better than to disobey by breaking his punishment position.
His poor cock had been locked away so long that it throbbed and bounced around obscenely as the paddle pulverized his tender tush.
“He only gets to cum once or twice a year,” Jessica explained. “And we always recycle whatever he releases. Why don’t you see if you can milk the little miscreant?”
Jane reached in and grabbed the punished executive tightly by his hanging cock. Allan moaned and thrashed in time with the pounding paddle.
Claire grabbed an empty wine glass and held it under his throbbing erection. Jane began pumping her hand up and down, milking his member as if it were a cow’s udder.
Claire laughed and spanked her boss hard with her open hand, urging Jane on.
“NO … no PLEASE” Allan begged, twitching and shaking. They could all see that he wouldn’t last much longer.
“My God, he’s just pathetic Jessica!” said Allan’s boss as she watched him involuntarily hump his neighbors hand.
“This is the ONLY kind of sex I allow him anymore,” Jessica smirked.
“Thar he BLOWS!” yelled Jane as she milked the helpless man. Claire continued spanking him as he spewed six months of stored semen into the empty glass. He was crying and beating the couch with his fists as he shot jets of sticky sperm.
The inebriated ladies all laughed and congratulated one another as Allan collapsed in a heap. Jessica made Allan pour each of them another glass of wine.
“Not you though, slut!” she taunted. “You only get the white wine!”
Forcing his arms behind his back again, Jessica lifted Allan to his feet. She pushed him forward toward the other ladies.
“The filthy little weenie always cleans up his messes,” she laughed. “Claire, why don’t you do the honors?”
Claire held up and swirled the glass holding Allan’s impressive load of thick slime.
“Ewww! Nasty!” she whined, turning up her nose.
“Ugh! Disgusting!” Jane exclaimed.
From the expression on Allan’s face, it was clear he agreed. He did NOT want to drink his rapidly congealing slime!
Jessica twisted Allan’s arms behind him and forced his face forward toward Claire. Giggling like a schoolgirl, the sexy young secretary lifted the glass to his lips and began to pour.
“Here you go – drink up!” she ordered her boss, her face a mixture of amusement and distaste.
“That’s right,” snarled Jessica. “You’d better get it ALL down if you know what’s good for you!”
Allan sputtered and gagged, but he swallowed as fast as his secretary poured the vile stuff into him. At Jessica’s urging, he pursed his lips and sucked the slimy little globs off the rim. She even made him lick out the inside of the glass. A little trail of sperm dripped down his chin as he choked and sobbed.
Linda was visibly excited as she watched her assistant degrade himself. “Damn, it makes me horny watching that little slime-swallower take his medicine,” she exclaimed.
“Why don’t you stay a while,” Jessica answered with a wink. “I have an idea for later.”
Jane and Claire thanked Jessica for a fascinating evening. Allan was sent to get them their coats from the closet.
“I’ll see you at the office, Mr. Knawtee!” Claire smirked as she patted the naked executive on his painful posterior. He flinched. How could he ever face her again?
“Yep, I’ll see you around the neighborhood!” Jane laughed as she took her leave.
5. SUCKING UP TO THE BOSS
After the other two ladies had departed, Jessica grabbed Allan by his hairless balls and pulled him back into the living room. Linda followed closely behind, curious.
“You got your boss all hot and bothered,” she told him. “I think you owe her some relief.”
“Why don’t you lie back on the couch, Linda?” Jessica suggested.
Linda relaxed her huge bulk back into the sofa. Jessica gently hiked up her green dress. Linda’s eyes opened wide and arched her back as Jessica slowly peeled Linda’s white panties down and off.
Grabbing the whimpering Allan, she tied his wrists together behind his back with Linda’s panties, then shoved him hard over the arm of the sofa. He landed with his face between his boss’s legs.
Jessica opened a drawer and pulled out a mean-looking leather flogger. Allan began to cry and plead with her.
“No – no please Dear my ass is so sore – p-p-please don’t whip me!” he sobbed.
“Shut up, slut!” she snarled. “Get your face in there and make your boss happy!”
She swung the heavy flogger across the pathetic posterior of the punished penitent. He screamed and kicked, but pushed his face forward frantically between Linda’s massive thighs.
Jessica swung the flogger back and forth, painting Allan’s scarlet upraised cheeks with pain with both backhand and forehand strokes. She wasn’t hitting terribly hard, but the flesh was so sore from his previous paddling that he could barely take it. Each stroke brushed across the sensitive skin and he wriggled with agony up into the soft mass of hairy flesh before him.
Allan was mad with pain and fear as he struggled forward into his boss’s crotch. His hands were tied uselessly behind him and his wife was urging him forward with the whip. Linda pulled her dress higher and spread her thighs wide. Then she parted her furry lips with her hands.
She was very very wet, and Allan buried his face in the hot folds. He’d had thousands of hours of training in the art of pussy pleasure but was too frantic to do his task with accustomed skill, especially bound as he was. He bucked with the strokes of the whip as he nuzzled his nose and lips into his boss’s snatch and began to lick. Her thick gray bush was quite sticky with her arousal, but he lapped as fast and hard as he could.
Linda hadn’t had sex in years, since her husband had died. Nobody had ever given her oral sex, certainly not her husband and not even the boys she’d dated before marriage so many years before. She moaned, grabbing her pathetic subordinate by the head and pushing herself against him as he lapped at her inner flesh.
It felt so good! The rhythm of the whip set his face and tongue into a regular stimulation of her pleasure center. She had detested the little twerp for so long, and now here he was, helpless, giving her the most exquisite sensations. She bucked up against him along with the beat of the whip on his naked ass.
Jessica sensed that Linda was getting close, so she started hitting Allan harder. He pushed his open mouth up against her and mashed his tongue into her clit, bucking forward and back with the searing pain in his backside. He was screaming into her, and desperately hoped the pain would stop with her orgasm.
Linda suddenly arched and grabbed his head, grinding his howling mouth against her sex as she cried out in joyous release. She shook and shrilled and trembled as she forced his face into her hot hole.
“Oh my God! Hit him harder!” she cried. “It feels AMAZING when he screams!”
Jessica smiled. She was only getting warmed up. She began whipping the upturned bottom before her in real earnest now, watching his balls swing back and forth as she flogged him again and again.
“You better make her cum again or I’m gonna beat you till you bleed!”
PLEASE CONTACT THE AUTHOR FOR CUSTOM-DRAWN ILLUSTRATIONS FOR THIS STORY
MEETING THE BOOK GROUP by allan knawtee