Torturing & Tutoring the Family
Copyright© 2025 by Ted E. Bear
Chapter 4
BDSM Sex Story: Chapter 4 - All get tortured to pay for college by a dad's sadistic employer.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Ma/ft Fa/Fa Fa/ft Mult Blackmail NonConsensual Slavery Lesbian Heterosexual Fiction Cuckold Wimp Husband Incest Mother Father Daughter BDSM Humiliation Rough Sadistic Torture Gang Bang White Couple Anal Sex Cream Pie Double Penetration Exhibitionism Sex Toys Voyeurism Big Breasts Transformation
With Tiffany and Cheryl home for the summer, still room mates, sharing Tiffany’s bed, the visits from “Master” were to become more frequent, and the family income would grow accordingly (not declared as income, for tax purposes). Father had become used to seeing his wife, and then his daughter, too, being abused, “punished”, for pay, and the women had made their adjustments to it also. Mother was “One”; Tiffany was “Two”, and Cheryl became “Three.” They had a psychological defense mechanism, similar to the way abused children develop multiple personality disorder. The pain and humiliation endured by One, Two, or Three was not remembered clearly by mother, daughter, or friend; there were no nightmares, no guilt, no mood depressions when they resumed their normal personalities.
However, even Master couldn’t afford the weekly visits that had been promised, at the increased rates, unless others shared the cost. So it was that, when he showed up in his “police” uniform, he had two strange men with him, who wore masks to protect their identities. There was also a woman, thirtyish, pretty, who also wore a mask.
He did not reveal that, however, until things were ready, with father bound to a floor-support column, expecting to be a passive spectator, and One, Two, and Three all naked and immobilized, their wrists cuffed, with chains from the cuffs to hooks in the joists above the basement “playroom.” One other detail: Three was a virgin, and Master wanted to reserve her maidenhead for a later date. He had installed three gold rings through the skin of each of her outer labia. Master threaded a shoelace through the six rings, just as you would lace a shoe, pulled it tight, and tied a bow knot. Nothing, he thought, would get into her vagina, as long as the lace was tied. It was only then that he sprang his surprise, the three new Masters. He introduced the helpless women as “Slave One, Slave Two, and Slave Three”, then gestured to the bound father and announced, “Slave Four.”
“Four,” shouted the masked woman, “you may call me Tease.” She pulled his shorts down around his ankles and proceeded to stroke his cock until it stood tall, only a matter of seconds. She then lived up to her name, keeping him sexually excited, but never allowing him the relief of ejaculation.
The next masked guest, six-two and muscular, selected Two and said, “You can call me Brute.” The second masked man, who was shorter and greying at the temples, selected the diminutive virgin, Three. “Call me Daddy,” he said. That left the original Master with One, the mother. He didn’t mind that; he’d started out with her before the unexpected addition of Two and Three to his string of slaves.
Going in numerical order, One would be punished first, while the others watched. Of course, Tease had started out of turn, but no one minded that.
Master went to One, who stood, arms raised, ready to do his bidding. He put ankle cuffs on her, but that did not alarm her. She felt something being inserted in her rectum. OK, it was lubricated, and it didn’t hurt. He placed in her mouth a kind of thick rubber balloon and began to inflate it. It soon filled her mouth. She could still breathe through her nose. He pumped it up some more, until it bulged out between her stretched lips, and her jaw ached as if it would be unhinged. One tried to tell him it was too much, but only faint honking noises came from her nose. It was a very effective gag.
One watched Master bring out an ordinary kitchen chair, the kind with a chromed metal frame. He placed on the seat a curious appliance, an egg shaped ball, like a big rugby ball, which had a rubber penis sticking out of it. Brute helped unhook her arms and carry her to the chair. As she expected, the two men lowered her until the rubbery penis entered her vagina. They lowered her a bit more, so that she was sitting on the ball, not so very bad, so far. Her wrist cuffs were chained together, behind the chair back. Master usually tortured her perforated inner lips, which seemed to her to have actually grown larger, from being stretched. Now, with the ball squashing up against her lower lips and the rubber penis comfortably inside her, there was no way Master could put the hooks through her labia. She began to think she might get off easy.
Next, Master slipped a noose of rope over each of her ample breasts and pulled it snug. In middle age, One’s breasts had begun to sag, so when the nooses were tightened, the effect was to squeeze the part close to her chest and make the rest assume a more spherical shape. Her nipples became erect, and the taut skin began to blush pink. Still, as an experienced slave, One could endure that discomfort. One, as a personality, existed only when the Master visited. Her whole life was one of submission and punishment, but since she did not exist at other times, she could look forward to any discomfort ending. In the morning, “mother” might bear bruises, but she would remember little of what One went through. Were it not so, they would have ceased the slavery long ago, even though that might mean poverty and losing their home.
One was a bit surprised when the two men led the ropes from her breasts over her shoulders, crossed then behind her back, and ran the ends through the rings in her ankle cuffs. As the ropes were pulled, tightened, One had to bend her knees, raise her ankles, until they were uncomfortably high, beside her buttocks, and she spread her knees to the utmost to allow that last half inch of ankle movement. Each man knotted a rope and let go.
Instantly, One realized her plight. Even with great effort, she could not hold her ankles that high. If she let them down, even a bit, the nooses tightened around her breasts, trying to pull them up and back over her shoulders. Her leg muscles hurt, stretched on one side, cramped tight on the other, but she could not relax for a second, for the pain of having her breasts stretched, and at the same time squeezed, was too much to bear. One screamed in protest but, gagged as she was, it sounded like a whining puppy. Her eyes went wide with horror, as Master applied still another torment. He put a strap across her lap and passed it under the chair seat. When he tightened it, every minute or so, it not only tightened the ropes to her tortured breasts. It also compressed the ball she was sitting on. Fluid from the ball was forced up into the penis within her, which swelled under the pressure. After several tightenings, One felt as if her vagina could stretch no more and must surely tear.
The men placed the chair where the others, slaves and masters, could watch One’s torment. Her obvious distress brought a round of applause from the visitors; even Tease stopped to clap. But that was not all. The thing in her rectum had a tail trailing out through One’s anus, a hose. Master connected it to another hose, and One felt hot fluid flowing into her, stretching her bowels, competing for room in her pelvis with her already distended vagina. Even the beatings One had suffered did not engender the terror she felt, for Master had simply left her there, strapped to the chair, with the pain in her breasts, her legs, her cunt and her ass building constantly. Beatings are brief; this could go on for hours!
Two, standing there with her arms held high, had been watching, trying to stay detached. The anticipation of pain can be as bad as the torture itself. She had learned to control herself. What would be would be.
Brute kneaded Two’s full breasts with his big hands. Two thought her big, nicely shaped, upstanding breasts were her most attractive feature. Lots of women have nice legs, slim waists, but few had the centerfold grade breasts that Two possessed. From her breasts, he ran his hands down over her waist and hips, then kneaded her buttocks. Two knew she looked good; she couldn’t blame him for wanting to touch, too. Then he examined her crotch.
She was absolutely smooth down there, freshly depilated. The perforations in her outer lips were obvious, and Brute had to see for himself, exploring her vulva, then finger-fucking her vagina. Two had never experienced an orgasm, except by either cunnilingus or the water torture, as she thought of it, a spray of water directed at her love button. The stirring of his finger, then fingers, within her affected her no more than a spoon stirring cake batter, except that she was a bit dry, and the friction was uncomfortable. Master started snapping his fingers. Two had been conditioned; at the sound of finger snaps, her juices flowed; she could no longer prevent it. “That’s better,” said Brute, as he fucked her hole with three fingers now.
He was obviously not getting what he wanted, so he decided to put ankle cuffs on her and go for some rather more spectacular bondage. With a rope which could slide through a screw eye in the joists above, he slowly hauled one foot as far as it would go. That left Two hanging awkwardly, but with some effort she was able to lift her other leg so it lay alongside the first. At least, then, though she was hanging from her wrists and one ankle, she wasn’t being split at the crotch.
Brute was not finished, however. He passed the rope from the second ankle through an eye which seemed impossibly far away and hauled on the rope. Her legs were pulled apart in a wide Vee, so far that Two thought something would break, a hip joint, perhaps. She cried out and tried to twist her body, so that she would be doing a “split” fore and aft, instead of being impossibly stretched.
Brute unhooked the chains which held Two’s wrists, letting her body hang head down. With the strain of all her weight on the widespread legs, she hadn’t the strength to twist and raise herself. While she hung there, the blood draining to her head, her face reddening, brute selected some additional torture devices. One was a big vibrating penis, black and covered with protruding veins. It was intended for a compliant vagina, but Brute managed to force it through Two’s stretched anus, leaving the last inches protruding like a turd. It buzzed within her, the least of her worries, at that point.
Two was dimly aware of her friend, Three, crying for mercy, but she was too preoccupied with her own predicament to care. Brute took another vibrator, a shiny, smooth, metallic one, and laid it along the groove of Two’s vulva, not penetrating her vagina, lying between her labia, with the heavy butt end, where the batteries were, pressing against Two’s clitoris. To hold it in place, he threaded a catgut fishing leader through the perforations in Two’s outer labia and laced the vibrator in place. He snapped his fingers, watching her get juicy, then turned the vibrator on. Two found the sensation almost painful, frustrating. She imagined that the male equivalent of having her tender clitoris bussed like that would be to feed Brute’s penis into golf ball scrubber.
Brute and Master cooperated to raise Two’s arms and hang her wrists, far apart, form the joists above, so that she was no longer head down but belly down, her back arched, with her breasts hanging away from the wall of her chest. While there was no point of really acute pain, Two was overwhelmed by the totality of the aches and little pains. Every muscle seemed strained to its limit, her legs spread beyond belief, her arms stretched, her back bent almost double, and her belly stretched taut. Sure, there were gymnasts and dancers who could bend like that, but Two was no contortionist.
Still, Two knew her only function in life was to be punished, and she was resigned to endure it. She let her head loll down, while her arms were pulled back and apart in the “swan dive” position. It was almost, she reflected, as if she had been crucified.
Brute pulled her head back, lifting her face, and he passed a strap around her forehead to hold it up, with her neck extended painfully. He fastened the other end of the strap to the dildo which protruded from Two’s anus. If she relaxed the least bit, the strain pressed the penis painfully against the floor of her pelvis, crushing her vagina and stretching her anus to the point where she was sure the skin was tearing. Soon, however, the pain in her neck was too much to bear, and she let the strap support her head. even, she thought, if it might destroy her “down there”.
Two, with her face lifted like that, could see Tiffany’s father, quite naked now, with Tease. She had one long index finger up his ass, as she played with his scrotum. His penis stood tall, getting no relief at all. One, Tiffany’s mother, was sitting, obviously in pain, strapped to the chair. Two could see between One’s spread thighs, where the rubbery penis within One’s cunt had swollen in size until it looked like a grapefruit trying to be born. One’s labia were stretched to the limit. Master was oiling One’s tortured breasts, which the rope nooses stretched until they look like giant mushrooms. Liquid leaked from One’s anus and puddled on the floor. Her normally convex belly seemed swollen, stretched, and the fluid continued to distend her abdomen. Two knew that the intestines feel no pain, except one. They are very sensitive to stretching, and she knew One’s bowels must be stretched as they never and been. The woman’s skin was discolored and gleaming with sweat, as she struggled to endure, second after second, what must seem like endless torture. Master finished oiling the breasts and began pressing with his forefinger on One’s exposed clitoris, utterly vulnerable at the door of her bursting vagina.
Brute returned to Two, who was trying courageously to bear her pains without screaming uncontrollably. He kneaded her breasts, oiling them until they shone. Then he placed plastic tubes over her nipples; they had been designed to fit over a large cock, and they were much smaller in diameter than Two’s magnificent globes. When he pumped on them, sucking out the air, She screamed with pain and surprise as her slippery globes were sucked into a the shape of a man’s penis! She felt as if her sensitive nipples would burst, and the skin of her breasts was stretched beyond endurance. She was sure she would have permanent scars, even though the skin was not actually broken.
To encourage her screams, Brute paddled her ass with a board that had holes drilled in it. Every blow on her cheeks stretched the skin at the edges of the holes, leaving round “sucker marks”, as if she had been attacked by an octopus. The other visitors paused to watch, clapping politely when Brute stopped.