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Beware: Contains BDSM and incest.
Thanks again for your comments and support. Here’s the conclusion. And I agree with you: the chapter lengths have been unusually short. However, since I completed the entire story before posting Chapter 1, I haven’t been able to include your many creative suggestions. Also, I’ve already begun work on a new story, which has a different slant and much longer chapters. Although the new piece doesn’t include the identical Janice and Matt, it does contain characters that bear a resemblance to them – although their relationship is not one of mother/son.
Late on a hot June afternoon, Janice, a chronically bad mother, subservient to Matthew, her sexy, domineering son, stood nervously outside the Headmaster’s office at the private high school from which Matthew had just graduated. A few weeks had passed since Matt had begun punishing his single mother for years of egregious infractions, as well as provocative flirting and rampant exhibitionism, and fulfilled Janice’s longtime desire: being made sexually submissive to her son. Now Matt was inside the Headmaster’s office, talking privately to him. She wondered with growing excitement what kind of demeaning agenda they were planning for the afternoon.
Eventually the Headmaster called her name and she entered the plush office with its heavy, clubby leather furniture. She moved slowly, stiffly and gingerly, as if she was walking on thin ice, her body perspiring from her secret. The Headmaster thought he heard a metallic clinking, but assumed the sound was caused by metal pieces on the soles of Janice’s shoes, like tap-dancing shoes. Matt was standing in the corner, next to the video camera whose red light signaled it was already recording. The Headmaster sat at his large desk. With his thinning blond hair and doughy face, the Headmaster, who was 40, looked innocuous.
The two males exhibited an aura of camaraderie. On the Headmaster’s desk was a computer and a thick manila folder crammed with photos, so overfull that edges of several were visible. Janice guessed that the images were of her. She couldn’t see the computer screen properly, but it looked as if it had been stopped while watching a video, probably of her as well. Janice jerked her head around to stare at Matt, who avoided eye contact with her and stared out the window.
Although the Headmaster didn’t ask her to sit, he did invite her to pour herself a cocktail. She walked to the bar he kept on a wheeled table, added ice to a glass, filled it to the brim with premium vodka and said “Thank you, Sir.” The room was sweltering. Nervously, she took a long refreshing drink.
“I notice you offered a drink to neither me nor Matthew.”
“Oh,” she exclaimed. “I – I was so nervous, I didn’t even think of it.”
“Janice, Matthew has informed me that the two of you have begun a lengthy program of punishment for years of your transgressions. And that you have also agreed to discipline sessions for your ongoing improprieties. Your thoughtlessness with the drinks is a minor but perfect example.”
She took another drink of her cocktail. “Yes Sir.”
“That is all to the good,” the Headmaster continued. “But you have also committed infractions in relation to me and therefore, to this Academy as well. For example, you were repeatedly late for Parent-Teacher’s conferences. You were a no-show at the championship soccer match. And at the last minute, you canceled your assignment as chaperone for the Senior Prom. You disappointed a lot of the boys, who were eager to dance with you – slow dances, that is. And on numerous occasions, you forgot to write checks for soccer gear or field trips, or the checks were late. There is more, much more I could tediously recount. Need I continue?”
“No, Headmaster,” she replied meekly and shamefacedly, swallowing more liquor.
“So if you expect me to convince the Financial Aid office at Matt’s new college to grant him a full scholarship, as well as a generous living stipend, then I expect you to suffer the consequences of your misdeeds here.” She nodded, beginning to perspire. “You already know that the Academy, since its founding in the 1800s, has an honored tradition of rigid discipline.” He paused, so she nodded again, her chest heaving with humiliation and budding excitement. “Do you understand?”
“Yes, Sir, I do understand.” Her own son was slutting her out to this official, whom she’d repeatedly offended. Just the way her severe father had let her demeaning uncle and forceful brother administer punishments and use her for all kinds of sexual acts. The same way that her former husband had repeatedly given her to his harsh and demanding best friend. On the other hand, the sandy-haired Headmaster, in his early 40s, wasn’t a bad-looking guy. He was certainly firm and authoritative.
“We would begin immediately. Your sessions would be a minimum of once weekly and extend throughout the summer.” Janice noticed that some photos peeked out from a closed file folder lying on the Headmaster’s desk. She wondered if they were the photos Matt had been taking casino oyna of her for weeks.
“In addition, if the Dean and Head of Admissions at the college wish to interview Matt this summer, you would need to accompany him there to answer any financial questions and prove your. . . goodwill and. . . cooperation with three masters there. . . all at the same time. These are very busy men and they would want to. . . prove yourself to them in a group. . . session.” Stunned, Janice closed her eyes. “The Dean told me they have a. . . special apartment for out-of-town guests. In order to continue, you need to say out loud what you want,” he added. Janice finished her drink, swaying slightly from the amount of alcohol, the day’s heat and her deepening subjugation to ever more men.
“Headmaster, please discipline me now for my bad behavior. I will obey all your commands. And I will. . . cooperate with the Dean and the Head of Admissions.” The Dean sat quietly for a minute, letting the tension rise.
“All right, remove your jacket.” Under the jacket was a thick, heavily starched white blouse, so unlike the gauzy ones she normally wore.
Matt spoke for the first time. “That’s not an approved blouse. You’ll be punished for that.” Janice nodded, knowing that trying to explain would only make her discipline harsher. She hadn’t worn one of her usual transparent blouses because it would have immediately exposed the trashy bra and other items that Matt had forced her to wear. That morning, she’d found a box on the kitchen table at her place setting. Inside, she’d blushed at the expensive but lurid lingerie. She’d never worn such a crudely slutty pair of bra and panties before. Obviously Matt wanted to shame her as much as possible. He said, “Wear it today” in a tone that brooked no resistance.
“Now the blouse,” the Headmaster said.
She stripped it off as the Headmaster ogled the mature mother’s superb body. As ordered by Matt, she was wearing a classically slutty, dark gray bra, with cutouts. Her huge dusky areola filled the nude space. Her charcoal nipples were bulging. She wore the cutout bra not to simply expose her nipples, but to expose them so they could be clamped and chained. Chrome clamps hung down from the turgid stalks, with 6-inch chains, comprised of small but thick links, hanging below the clamps. Suddenly Janice felt pleased that she was wearing the cutout bra.
The Headmaster actually gasped; he was stunned. “How. . . how long have you been wearing those clamps and chains?” the flustered Headmaster asked, growing hard.
“Since lunchtime,” Matthew said. Janice was herself stunned that she was actually standing in a stifling hot school office, the late afternoon sun streaming through the windows, her perspiring chest exposed to a school official, her aching nipples bound and excited, thrilled to be punished for her chronic badness and forced to perform the most shameful sexual acts with her son and this doughy, unappealing and officious guy.
“Well, you better lose the skirt,” Her long, toned legs came into view, accentuated by the matching light green garter belt and stockings, offset by her Mediterranean-tone skin that was accentuated by a light tan. Matt had insisted that, despite the heat, she wear the stockings and garter belt. The Headmaster gasped when the third and fourth chains appeared. Once she discarded the skirt, she spread her legs so he could inspect the crotchless panties, the dark gray material framing her bulging, enflamed labia, the pussy lips looking even larger than usual since they were squeezed outward by the tight, undersized panties. Her dusky labia were clamped and chained, just like her dark nipples.
“Matthew, would you please?” Matt pulled his still camera from a pocket and photographer her.
Somehow, Janice felt better being totally exposed, her pussy now naked as well as her tits. Without the Headmaster or Matt having to order her, Janice lifted her arms and placed her arms behind her back, the posture lifting the heavy tits with their hardware up so he could stare at them in their full bondaged beauty. The nipple chains were so long that they rubbed back and forth across her swollen clit. The three people remained in silence, the faint breeze ruffling the curtains, her skin lustrous with perspiration. She felt this moment was meant to be.
After he’d had his visual fill of the breathtaking mother in her submissive posture, the Headmaster said, “Kneel on the ottoman.” While Matt tilted down the angle of the video camera, he assumed the position, automatically spreading her knees as wide as possible, so her pussy lips opened. Matt held the glass of vodka to his mother’s lips and she gratefully swallowed. The Headmaster nodded at Matt, who quietly walked over till he stood behind his mother. He wound a thin, black nylon rope in a figure eight around the base of her tits, which were still encased in the cut-out bra. Janice grunted as the Headmaster tied black leather shoelaces to the pussy clamps and stretched them outward to the sides, exposing her sopping inner lips and channel as he tied off the canlı casino clamps to the metal grommets sewn into the tops of her stockings.
The Headmaster removed a 12-inch willow strap from a hook and began striking her bound tits as Matt pumped three fingers in and out of her gash, periodically slapping her grossly swollen clit and distended labia. Her ballooning tits immediately showed the strap marks and she came quickly, surprising the Headmaster and bucking so hard that he had to prevent her from toppling over.
The Headmaster leaned against the front of his desk and took out his big dick while Matt lubed his own. The Headmaster saw her checking his cock – bigger than she’d expected from the looks of him – through half-lidded eyes. As Janice leaned forward and engulfed the Headmaster’s dick, simultaneously stroking his balls, her ass was angled perfectly for her son’s cock, especially since her knees and legs were already widespread. Using his thumbnails, Matt ripped the fabric of her crotchless panties, extending the vertical slit at the rear, and fitted the head of his cock into his mother’s dusky ring and pushed, the crown entering easily. Matt had not been exaggerating, the Headmaster realized: this hot MILF was by far the best cocksucker he’d ever had. She had so much saliva that long thick strands extended from his prick to her lips, ropes of it breaking off and splattering on her bound chest and bulging mounds.
While Matt added still photos to the video images, Janice was lost in her sub space, the heavy chains jerking the nipple and pussy clamps, doing what she did with superb skill, her mouth and ass full of cock, delirious with excitement, debasing herself in self-punishment and servitude for her many misdeeds and offenses.
The Headmaster decided to test the incredible nipples even more. He removed the nipple clamps and chains, attached a pair of nipple pumps to the mother’s dark stalks and slowly pulled the bulging 1-inch tips into the clear plastic tubes. “A pain slut like you are likes having both your cunt lips and nipples stretched at the same time.” Janice adjusted her hips so that Matt’s cock could drive all the way into her ass. Matt and the Headmaster began fucking the repentant mother’s ass and mouth faster, the suction tubes swaying wildly on her nipples as the cunt clamps stretched her labia and the chains slapped against her tender inner thighs.
When his cum was imminent, the Headmaster pulled out of her big lips and shot his entire plentiful load onto her forehead. As his white cum dump ran over her thick black eyebrows and started dripping off them onto her cheeks and nose, he increased the suction of the nipple pumps. She began writhing more jerkily, the extra twisting motions pulling and hurting her clamped cunt lips even more, moaning louder and longer as her stretched nipples were tugged till they had doubled in length to an obscene two inches.
The gorgeous mother, whose debauched desire for Double Penetration was exceeded only by her lust for Triple Penetration, came so wildly that the twisting of her hips brought on Matt’s finish. He pulled out and shot off into her empty cocktail glass with one of his largest loads.
The two males collapsed into chairs as the slut mother kneeled on the ottoman. Matt took photos. The prodigious facial she’d received from the Headmaster now coated her from forehead to chin. Cum had even sprayed into one of her ears and was dripping onto the ottoman. Matt pulled the short black hair on the rear of her head till her drenched face looked upward and held the glassful of fresh hot spunk above her. As the Headmaster untied the black shoelaces from the stocking grommets, removed the labia clamps and chains, and released the pressure from the nipple pumps, Janice’s mouth opened in a scream as blood returned to the numbed nipples and cunt lips, filling her with pain and a third orgasm.
Once her gasping ended, the Headmaster tilted the glass and began pouring his jism into her gaping mouth. “We anoint you as the official cum, anal and pain slut of this school,” the Headmaster announced in a pompous voice. Matt took more shots. But the Headmaster, not as experienced with this cum slut as Matt was, poured too quickly and Janice choked, spurting a cloud of cum that splattered with big gobs of jizz all over her inflamed dark nipples, taut tits, spread thighs and stocking tops. Kneeling in a daze as the Headmaster removed her nipple suckers and Matt undid the rope around her tits, she swooned with a new round of pain and pleasure in her tits and cunt.
Once Matt was finished taking photos, the Headmaster said, “That was a satisfactory session, Janice,” tucked his cock back into his pants and informed Janice that she could get dressed – but without the use of a towel or the ladies room. “Since this was our first session, I went lightly with you.” Janice pulled the tight tiny panties onto her raw labia and winced, deeply humiliated by being forced to dress in front of the men’s stares. “The next time will be harsher. And I know that my colleagues at the college have rigorous, demanding kaçak casino personal styles and will not go easy on you.” He spoke as if she’d already been told that the Headmaster would be slutting her out to his college cronies.
The lustful mother fastened her heavy blouse, the fabric matting disgustingly to the smears of cum all over the cups of her cutout bra. Her raw nipples rubbed painfully against the stiff fabric. “Wha, what do they demand?” the submissive mother croaked, her lips still plastered with gunk.
“Well, it depends on a variety of factors: the verbal report I tell them, the stills and videos, their evaluation of you in person, their mood at the moment, your prompt obedience, your threshold of pain, your tolerance for punishment.
“I can warn you: they don’t take kindly to bad parenting. So I can say that they will probably abuse those incredible tits and nipples of yours first, then whip or cane your tits and ass, and since there will be three of them, do a Triple Penetration.” She put on her blouse, the filmy fabric immediately sticking to the spunk all over her chest and belly.
“The Dean is quite a striking figure: severe, tall, slender, and strong-jawed, with silver hair. He has a predisposition to body modification.”
“What does that mean?” she asked.
“He relishes the modification of tits and nipples, clits and labia. That is, he likes big ones, and he takes special pleasure in making big ones like yours even bigger.” Janice closed her eyes, imagining the clamps, weights, chains and suction devices that could be used on her.
“And the Head of Financial Aid is an innocuous-looking fellow, which is a good cover for his. . . true inner nature, which is most firm.”
“Oh my,” Janice said, her pussy wetting again as she pulled her skirt over her sticky thighs. How would she make her way home, she wondered, when she reeked of cum? There might be nobody in the Administration building at this late hour on a Friday, but what about in the parking lot? And there were no tissues in her car.
“For the college visit, you are instructed to take all of your toys, devices and. . . most suitable lingerie with you. Matt, you’ll be sure to take both your cameras. It will be a long weekend,” he warned. Janice shuddered. “You are now dismissed.”
“Yes, Sir, and thank you.”
The Headmaster slapped her cum-streaked cheek. “Be specific.”
She thought carefully, trying to remember everything. “Thank you, Sir, and thank you, Matthew, for binding and beating my tits, clamping and stretching my cunt lips, letting me suck your cock, giving me a face bath, fucking my ass, pumping my nipples, and allowing me to swallow your cum.”
The Headmaster slapped her other cheek. “Is that all?”
Janice concentrated. “Oh. And thank you for permitting me to leave your cum on my skin?”
The Headmaster nodded. “That’s better.” Matt and Janice walked to the door. She was so used to walking gingerly that she did so even now, as if the clamps and chains were still suspended from her nipples and labial lips.
Since her youth, Janice had experienced many triple penetrations, first a series of them with her father, brother and uncle; and later a number of them with her husband, brother and father; then with her husband and his friends. But since she’d been divorced for years, it had been a long time since the last ones. “Sir, you mentioned three masters at the college. Do you know who the third person will be when Matthew and I are at the college?”
The Headmaster stared at this cum-covered beauty who would apparently undergo endless humiliation and severe subjugation for the sake of her adored son. An incestuous submissive who was about to walk out the door onto the campus with streaks of white cum crisscrossing her black hair, with thick blotches of jism all over her beautifully smooth skin and tanned face. “The third dominant, Janice, will of course be your son, Matthew. Or more appropriately, your son and your Master.”
Janice nodded and they departed. The entire time that Matt took her home, neither of them spoke. Janice was lost in daydreams. She already knew that the university had one of the most beautiful campuses in the country, filled with handsome stone buildings and large trees. The Headmaster made it sound as if the Dean of the university looked opposite from the Headmaster. The Dean would be older and unsmiling, tall and wiry, with salt and pepper hair. He would demand instant obedience. His hands would be large and bony. His large office would be filled with leather. He would be much more experienced than this Headmaster. He would dominate her into doing the Triple Penetration with the other college official and Matthew. And they wouldn’t be gentle.
Janice felt her sore nipples growing and her pussy wetting. Unconsciously, she slid down in the seat and spread out her legs as widely as possible, the skirt sliding toward her groin and exposing her gorgeous thighs and the disheveled green stockings and garter belt straps. Matt pulled her skirt aside until her pussy was exposed, the fat lips extending up from between the panty fabric. She was too lost in her dream world to even notice that she was blatantly exposed to any van or truck driver who might pull up next to them at a red light.
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