Torturing Missy
by The Once and Future Chairman
Copyright© 2024 by The Once and Future Chairman
BDSM Sex Story: Missy is taken to the play room by an unknown mistress. She is told that if she can endure four hours of severe torture without screaming, she will be allowed an hour of orgasms, but if she can't, she will be given to the mistress for an entire weekend. Will she win her orgasms?
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Consensual Slavery Lesbian Heterosexual Fiction BDSM DomSub MaleDom FemaleDom Light Bond Rough Sadistic Spanking Torture Needles .
“Missy, I want you to go put on your hood, strip naked, put on your stockings, garter, and heels, then your wrist and ankle cuffs, and head down to the play room to await my pleasure.”
Carolyn Helms felt a momentary flash of frustration at that command. She’d been watching one of her favourite programmes, and hated to stop. But nevertheless, she leapt to her feet and headed off to do as she was told. When she was addressed as “Missy” rather than “Carolyn” it was not her husband, Donald, talking to his wife, but rather her Owner giving orders to his property. She really enjoyed the brief times when she got to be Carolyn rather than Missy, but she had agreed many years ago that Donald would be her Owner in every sense of the word.
She was feeling more than a bit anxious. The “play room” was the basement of their house. It was over four hundred square meters, and every centimeter was dedicated to ways of inflicting pain on her. She was almost always blindfolded in the play room, since Donald didn’t want her to know what he was planning to do to her. But whenever he ordered her to wear the hood, rather than just a blindfold, it was because he had something really severe in mind.
As she stood in her “bedroom,” getting prepared as ordered, she began to tremble in anticipation. Of course, to call it a bedroom was another misnomer. There was no bed there. She slept either in one of the stations in the play room, or in her cage in her Owner’s bedroom. Instead, this was the room that contained all of her outfits, her various dildos and plugs, her hoods and blindfolds, collars and cuffs. It also contained her storage crate, where her Owner put her when he had a vanilla date for the evening, and didn’t want to have to explain about Missy, or even just when he was going out for a few hours.
She had been ordered to put on her hood first. It would make doing all the other things she had been ordered to do harder, but she had learned long ago to follow commands exactly, and in order. The one time she had taken it upon herself to re-order her commands, well, the bruises from that session had lasted for a week, and you could still see the scars, if you knew where to look.
Of course, you also had to know which scars to look at. Missy had endured many severe treatments over the years, and her Owner had his own version of “the burned hand teaches best.” He always said, “The scarred slave suffers best.” She could point out the scars from the time he had used her cunt as an ashtray, and the time he carved his initials into her ass, and the time, well, she shuddered to think of all the times he’d hurt her enough to leave scars.
She shuddered, but she loved it. No, not just loved it, she needed it, she craved it. She only felt fully alive when she was treated as a thing, suitable only for sucking cock, and for screaming. The longer and louder she screamed, the more alive she felt.
Her hood was full coverage, save for an opening in the rear for her ponytail to thread through, and an opening for her mouth, in case he wanted to either gag her, or face-fuck her. It also included a posture collar, so she was forced to hold her head upright. In addition, the collar incorporated the inside of a sphygmomanometer (aka a blood pressure cuff), which her Owner used when he wanted to indulge in a bit of breath play.
After getting her hood on, and the posture collar locked, it could only be removed by her Owner, or someone to whom he gave the key. She put on her stockings, rolling them smoothly up her legs (thank goodness she had shaved her legs well that morning), then her garter belt, and her heels. They were too high to wear out of the house (at least, not unless her Owner wanted her to fall on her ass), but if she moved slowly, she could walk in them, even down the stairs to the play room. And fortunately for her, she had plenty of practice walking from her bedroom to the play room in heels and blinded.
Finally, she locked on her wrist and ankle cuffs, and headed to the play room. Since her Owner hadn’t told her a specific station to go to, she knew he wanted her on her dildo mount. This was a dildo (actually, there were several, for when they were having large play parties, and the other Owners needed places to park currently unused sluts). The dildo stood straight up, and its height was adjustable. She stood over it, then tapped the toe switch that raised it, until her toes were barely touching the floor. It was uncomfortable as hell, since it pushed right on her cervix, and concentrated her weight there, but she definitely had learned better than to complain (that was another session in the play room that still gave her nightmares).
Although her Owner had not told her to put in earplugs, she couldn’t hear anything from the rest of the house. The soundproofing in the play room was excellent, and a good thing, too. She had been known to scream quite loudly, and when there were several other sluts beside her, all screaming as loudly, the cops would surely have been summoned otherwise.
So she stood, hurting, waiting for her Owner to come down. She never knew how long he’d take, and it really didn’t matter. He was her Owner, and like every other piece of property in the house, she was at his disposal, whenever he got around to it. She wondered which station he would use tonight. Would it be the Hot Box? The Spanish Pony? The Drowning Tank? The Electric Chair? The Rack? One of the many whipping frames, spanking benches, or torture tables? As far as she knew, he hadn’t added any new equipment lately that she needed to break in.
Finally, after a minute, or an hour, or a day (she couldn’t tell), she heard footsteps coming down the stairs. Multiple sets of footsteps. That scared her. Some of the worst, the most severe, sessions she had survived had been when he invited guests over, whether it was to let them play with her, or just to have a little friendly competition between her and the other Owner’s sluts.
Her Owner entered (she recognised the sound of his footsteps after all these years), and apparently saw her correctly mounted on the dildo, with her hood, cuffs, and outfit properly on, since he murmured a quiet, “Good girl, Missy!” to her.
She heard another person enter, probably female, since she heard a firm but light tread, maybe a mistress in boots? She heard another set of footsteps, but recognised the sound of bare feet, probably a slave girl.
Her Owner spoke up. “Missy, I’ve invited the Lady Joanne to come over tonight to try to make you scream, while I watch and am entertained by her slut, Robin. I’ve told the Lady what incredible endurance you have. If you can hold out from screaming for at least four hours, I’ll permit you one hour of as many orgasms as you can manage, no limits. Make me proud.”
An hour of orgasms? Given that Missy was lucky if she was allowed one orgasm a month, an hour’s worth was a prize beyond imagining. She was determined not to scream.
She felt another mouth on hers, kissing her hard. It was not her Owner, she knew the feel of his lips and tongue, so it must be the Lady Joanne. She kissed Missy very gently at first, teasing her tongue, brushing her lips, then suddenly, she began to bite down. She bit Missy’s lower lip hard enough to draw blood, as Missy could taste it in her mouth. The Lady Joanne withdrew, and she felt her bring her mouth close to Missy’s ears.
She whispered, “Good evening, Missy. I’m going to have such fun with you tonight. Your Owner has promised me a full weekend to torture you if I can get you to scream in less than four hours. And believe me, bitch, I’m going to win that weekend.”
Missy didn’t know how to respond, and decided her smartest course was to say nothing. And in fact, those were the last words the Lady Joanne spoke to her that evening.
Missy felt the dildo holding her in place withdraw, and simultaneously felt a tug on the chain attached to her collar. She wondered where her mistress of the evening was taking her. She followed for at least a kilometre (or so it felt), until she felt the Lady bending her onto a caning bench.
Missy hated the cane, but many years with her Owner, who loved it, had taught her to bear it. She thought she could get through this. She felt the Lady running her nails down her spine, and shivered. She then felt something tap her ass cheeks. She knew the Lady was ready to start.
When Missy felt the first blow, she nearly screamed. It wasn’t a cane, but a sjambok. She hated the sjambok worse than she hated the cane, because it hurt so much worse.
And it seemed the Lady knew how to use it, for she let the pain from the first strike peak before she struck again. And again, and again!
After a short eternity, the beating was finished. The Lady had come close to making Missy scream, but she’d managed to restrict herself to grunts, groans, sobs, and the occasional “Shit!” Missy was permitted to use profanity only when being tortured, but at least she’d kept enough self-control to keep from screaming.
She felt the Lady standing her up, and leading her across the play room yet again. “Where to this time?” Missy wondered, silently.
After being led on her leash to another part of the room, Missy felt her right wrist grabbed, and fastened to something, stretched out to the side. Then her left wrist was grabbed, and fastened far out to her left. She was standing with arms outstretched like an evangelical preacher, she could tell. Then she heard the sound of a winch, and felt her wrists lifted.
The winch kept lifting her by the wrists until her feet were at least a few centimeters off the ground. Missy groaned inside. Being fully suspended like this generally presaged something rough.
She heard a sudden loud CRACK by her right ear. “Shit,” she thought to herself. She recognised the sound of a bullwhip. One of her worst sessions in the play room had been when her Owner had hung her like she was hung now, and invited four single-tail experts to surround her, and whip her simultaneously until they had each drawn blood. This time there was only the Lady, but still, she knew it was going to be bad.
It was. The Lady knew how to use a bullwhip to best effect. First she whipped Missy’s tits. She seemed able to hit Missy’s nipples at least four strikes out of five. Missy wasn’t sure her breasts would survive the brutal treatment. Just as she was about to lose control and scream, however, the Lady shifted her target.
Next it was her ass. Fortunately for Missy, many years of whipping, paddling, caning, and the like had given her the proverbial “leather butt.” So while the single-tail did cut her ass cheeks (Missy knew because she felt the occasional drop or two of blood run down her ass), she didn’t feel it like she had felt the tit whipping. It was almost like the Lady was giving her a break.
But if that was the plan, it didn’t last long. Soon the Lady shifted her target, until the bullwhip was snapping against her belly. Missy was nervous, since the whipping she had already experienced led her to believe the Lady had the skill to accurately target her pussy, and more particularly her clit.
She was correct. Soon she felt the bullwhip crack against her pussy lips. Again, and again, and again. Finally came the strike Missy had been dreading, right on her clit.
She went rigid with pain. The only reason she didn’t scream immediately was that the agony had temporarily paralysed her ability to draw breath. By the time she could breathe again, she managed, by dint of past pain training to turn the scream into sobbing and crying, which was permitted. The Lady tried a few more clit strikes, but Missy managed, if only barely, to keep from screaming.
Apparently the Lady decided to try another tack, for Missy heard the winch, and felt herself being lowered to the ground. As her weight came off her wrists, she almost collapsed. But then she felt a naked female body pressed up against hers, and felt someone stroking her hair, almost as though attempting to comfort Missy.
Was it the Lady, or her slave? Missy couldn’t tell. The nudity was not a giveaway, as many Mistresses enjoyed stripping off before torturing their sluts. Then she felt a tug on her leash, and guessed it must be the Lady. She was led off to her next torment.
After a time, she felt the Lady lifting her right leg, high up and over, then back down. She felt a sharp edge pressed between her legs.There was a hum, and she felt the pressure increase until her feet no longer touched the floor. She realised she was mounted on the wooden pony.
The wooden pony was pure unadulterated evil, in Missy’s opinion. It didn’t hurt all that much, to begin with, but it didn’t stop. The agony just went on and on. She could shift positions some, leaning forward or backward, to move the pressure point around. But she couldn’t stop the pressure, or even lessen it. All she could do was choose between more pain on her clit, more on her cunt, or more on her asshole.
And while the sensory deprivation of the hood messed with her sense of the passage of time, it was worse on the wooden pony. She remembered one session where she was certain her Owner had left her on it all night and all the next day, and found out afterward it had been only three hours.
She began to cry again. She had mixed feelings about crying. On the one hand, she hated to show weakness. But on the other, she knew how much her Owner, and presumably the Lady, enjoyed knowing just how badly they were hurting her. And since she was trying not to scream with the pain she was in, crying, sobbing, and cursing were her only outlets.
After only a subjective day or two on the wooden pony, she was lowered back to the ground. Her cunt and asshole were almost numb, which she found often happened after a prolonged ride. She knew that within an hour or two, the pain would return in full force, and for several days it would be agony to be fucked in either cunt or asshole. So of course, she fully expected her Owner to arrange a gangbang for her tomorrow, just to enjoy her pain.
Missy realised that the Lady didn’t seem to be pushing her. With the sjambok, and the bullwhip, and the wooden pony, if the Lady had only carried on for a short time longer, Missy was sure she would have broken down and screamed. Why, she wondered, was the Lady doing this? All she could guess was that the Lady Joanne wanted to prolong Missy’s suffering, that she didn’t want to break her until she was as close as possible to the four hour mark. This gave Missy hope that she just might be able to hang in there, to use this insight to her advantage. She wanted that hour of unrestricted and unlimited orgasms. Now she began to hope that she might make it.
She again felt the familiar tugging on her leash, and again followed the Lady across the dungeon. She felt something pressing her breasts from above and below. Oh shit! It was the breast press, and that meant she was in the tit torture corner. Missy didn’t mind the breast press. Sure, it hurt. She was definitely busty enough to be well squeezed by it. And her Owner liked to see if he could get the gap between the boards down to less than three centimeters. So far, he hadn’t, but he kept on trying.
But it wasn’t the breast press she was afraid of. It was all the other torture toys here, all of which she (and more specifically her tits) had experienced in full measure on many occasions. She felt the press being tightened, further and further. She began to breathe more shallowly, trying to contain her pain. She felt it tightened to the point that she couldn’t bear any more, then it was tightened further.
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