Blind Date with a Mistress
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The Punishment Mistress [F/M noncons institution, spank, milking]
"No... No," he moaned aloud, to no one in particular, because he knew that the punishment mistress would take no heed of his protest. "Please, no," he said, louder, this time addressed to the punishment mistress. Part of his fear was his total vulnerability. He knew that there would be no escaping the severe strapping that he had been sentenced to for the week's misdeeds at the institution. He was totally naked, bent over a heavy punishment structure, and bound securely in place. His wrists were cuffed to the front legs of the structure. A wide leather strap encircled his waist, completely restricting evasive movement of his upper body. His ankles were cuffed to the rear legs of the structure. And, of course, he was acutely aware that his bare bottom was exactly where the punishment mistress wanted it. He was also aware that he was going to endure a severe strapping, whether he wanted to or not, and that there was nothing that he could do to interfere.
He had never been punished before at the institution for probation violators. Punishment was not meted out on a whim. He had accumulated several demerits, however, during the week for rule violations. He cursed his own hubris, his overconfidence that he could get away with breaking multiple rules without consequence. Hell, he told himself, that's why I'm at this place to begin with - I thought that I could get away with breaking the rules. What is it about me, he pondered, that ensures that I get caught every time?
The punishment mistress was a slender blonde woman about five feet nine, with bangs and a ponytail. Her white blouse and black skirt were complemented by black pumps. She had large blue eyes and a pleasant, although dispassionate, expression on her face when the inmate was led into the punishment room. The punishment mistress does not determine the severity of the punishment to be meted out to the recipients of her attentions. The severity, and often, the instrument of punishment, are decided only by the headmistress.
He had been led to the room with his hands cuffed behind him and wearing ankle chains. He was forcibly bent over the punishment structure, the waist strap secured, and the ankle chains removed. Then the two women who brought him into the punishment room stripped him of his clothes from the waist down and cuffed his ankles to the rear legs of the structure. They removed his handcuffs and stripped off his shirt. Finally, they cuffed his wrists to the structure.
He heard someone else enter the room. Then he saw the headmistress of the institution stand in front of him. "Mistress Deanna, he is to get a severe strapping. Give him sixty four strokes of the wood-handled strap. Witnesses, are you ready?"
"Yes, Miss Karen," answered the two women who had brought him to the room.
"Mistress Deanna, are you ready?"
"Yes, Miss Karen," the punishment mistress answered after she retrieved the strap from its repository.
"You may begin," she stated.
Deanna extended her arm and determined the correct distance and position, and, with her eye on the target, drew her arm far back and imparted a hard stroke of leather to the young man's bottom. He flinched as his ass cheeks jiggled from the force of the swat. A scant three or four seconds later, the next stroke landed. Deanna, keeping her feet in place, swiveled her hips as she completed the stroke with a full and complete follow-through. The young man sharply drew in his breath. A short instant later the three-inch-wide strap planted another reddened stripe on his quivering bottom. By the tenth stroke, he groaned with each swat. Deanna stopped for a moment to let the strapping thus far have an effect.
"Angie," said Deanna to one of the women who had brought the male in, "I'd like you to give him the next thirty strokes. Remember to follow-through."
The tall, dark-haired Angie, her eyes brightening, responded, "I'll be happy to." Her long black hair gave her an air of authority. She took the wood-handled strap from Deanna, and took her place to one side of the miscreant. Angie was in training for the position of strapmistress, and had applied the strap on a limited basis in a few previous sessions.
There was no doubt of Angie's ambition to be an accomplished strapmistress. The strength of her swats was testimony to her dedication and practice. The young man visibly flinched with each stroke. Following Deanna's example, Angie paused for a moment after administering ten swats. When she resumed, the male recipient gave a staccato exclamation as each stroke visited his bound and naked bottom. When Angie applied the third set of ten strokes, her enthusiasm was such that the male gave a vociferous shout each time the leather hit its target. Angie, her face flushed with excitement, handed the strap back to Deanna.
Deanna positioned herself directly behind her charge, smiled at Angie as if to say "watch how I do this" and applied the remaining twenty-four strokes in an alternating forehand-backhand fashion without stopping. This kind of application of the strap is especially painful because it is applied to the more tender skin on the outer sides of the nether cheeks. Her ponytail swishing back and forth, Deanna applied the leather with all her strength. The young man's nether globes were in a constant state of jiggling and quivering, and his howls were testimony to her effectiveness. Deanna thought to herself that she wold like to give her boyfriend a strapping like this - tied down so he couldn't move. The thought aroused her.
"Thank you, Mistress Deanna," the institution administrator said. "You may be excused if you wish. Please be back here in fifteen minutes to be briefed on the next punishment." Then, addressing the young man, she continued, "You will remain where you are for ten minutes. Then you will be led back to your room."
When the requisite time had elapsed, the women who brought him, Michelle and Angie, prepared to return him to his room. Angie unfastened his ankles from the punishment box and placed ankle cuffs on him. Michelle then released his wrists from the front legs of the punishment box and cuffed them behind his back. Finally, the waist cinch was released.
He desperately wanted to rub his bottom to mitigate the still-fresh pain from the leathering, and would be unable to do that as long as his hands were cuffed. He wasn't allowed to get dressed. Instead he was led, naked except for the ankle chains and handcuffs, back to his room. Michelle carried his clothes and Angie led him to his room, which was really more like a cell. The first thing he did when the restraints were removed was run his hands across his bottom, and then he lay face-down on his bed.
Michelle and Angie, who were themselves in training for positions as punishment mistresses, and Deanna gathered in the punishment room to be briefed by Miss Karen on the next recipient of discipline.
"We have a repeat offender here," Miss Karen stated. "You all may recognize him. He is in room 115. He's the one who has been here for being disorderly. He got a paddling the first time, and got the strap a week later. As if that wasn't enough, you gave him twenty four strokes of the cane just two weeks after that. This time he apparently started a food fight and attempted to wrongly implicate others. This pattern of repetition merits a very severe session today. Mistress Deanna, I suggest that you use the cane, forty eight strokes. And they are to be augmented."
"Will do, Miss Karen," responded Deanna.
"Michelle and Angie, please escort the next miscreant here."
They left to fetch the young man in the same manner as they had done with the previous one. Deanna prepared a salt water solution in a spray bottle for augmentation. When a punishment is augmented, salt water is sprayed on the recipient's bottom after every six strokes. This has the effect of greatly intensifying the sensation of the punishment. Augmentation is used only with repeat offenders displaying an unwillingness to heed the lessons of previous discipline. Also, when the maximum number of strokes for the cane, forty-eight, is to be administered, each set of six is placed at a slightly different angle, so that after the first set, every stroke will intersect with a previous stroke. For very severe sessions, there is no limit to the number of strokes permitted with the other instruments of correction.
Deanna selected a long, thin, flexible cane for the next session. The door opened with Michelle and Angie with the repeat offender in tow. As they were busy securing him to the punishment box, Deanna reflected on her duties at the institution. She was the first, and is currently the only, person with the title of Punishment Mistress. A punishment mistress must be knowledgeable and proficient with paddles, straps, canes, and switches. The training is long and arduous. A trainee is mentored by Deanna, and must practice her art daily on pillows before she is permitted to apply an instrument of correction to an inmate. A trainee's first experience at live administration of discipline is with a paddle. They are taught positioning and timing, and strength of the swats. If they still want to proceed after demonstrating proficiency with the paddle, the next instrument is the leather strap. When a high level of proficiency is demonstrated with the strap, the trainee is awarded the title of Strapmistress. Next comes training with the cane. Several trainees have not progressed to the title of Canemistress because of its requirement for absolute accuracy and control. If a Canemistress can demonstrate proficiency using switches, she is a Punishment Mistress. Angie is currently a Strapmistress trainee.
Miss Karen addressed the bound male. "I can't believe that you like being disciplined, yet you keep doing things that bring you back here. We're going to see if today's session will have a more lasting effect on you. I have directed the punishment mistress to give you four dozen strokes of the cane. I have also directed that they be augmented. That means that a salt water spray will be frequently applied to your naughty little bottom during the caning. They tell me that it really hurts." Turning to her staff, Miss Karen said, "Angie, I'd like you to apply the salt water. Michelle, are you ready to be the witness?"
"Yes Miss Karen," replied Michelle as she took her place as an observer. Angie was ready with the spray bottle. "Are you ready, Mistress Deanna?"
"I am ready, Miss Karen."
"Good. Please begin."
The bound male felt the punishment mistress lightly tap the thin rattan cane across the center of his exposed bottom as she prepared to start. A scant few seconds later he heard the swishing sound of the cane whipping through the air. As soon as he became aware of that sound he felt an intense flash of pain.
He sharply drew in his breath. The pain actually seemed to intensify for a couple of seconds before settling in at a constant level. The cane hurt considerably more than he imagined as this secondary reaction took hold. A few seconds elapsed and he heard the beginning of the dreaded swishing sound again, followed immediately by a new stripe of blinding pain. "OH!" The sound escaped involuntarily from his clenched teeth.
Mistress Deanna looked with satisfaction on the white weal which she expertly placed almost immediately next to the first one. As soon as the white weal began to turn red, she pressed her lips together, and, with her eye on the young man's bare bottom, brought the slender rattan cane far back and whipped it forward, making contact about a half inch away from the previous stroke.
"OHHH!" she heard the young man exclaim. She had heard a similar litany of pain many, many times before, and she would hear it many times again. She knew that she would never tire of it. Each one was a little different, but they all had the common thread of forced submission. She liked it best when they become aware of the inevitability of the punishment, and their absolute vulnerability. She parted her lips slightly, drew back the cane and placed another white-hot weal on the bared bottom cheeks of her charge. "Four," she counted to herself, feeling the slightest beginnings of arousal deep inside her body.
Deanna smiled slightly as she observed the young man valiantly attempting to refrain from giving voice to his predicament. As she looked at the ever-widening pattern of striations on the young man's bared bottom, she took careful aim and whipped another stroke immediately adjacent to the previous one. The whitened weal stood out in contrast to the other reddened lines.
"Gmmmfff!"
They always try to take it without crying out, Deanna thought to herself. Before it's over, he'll be telling me that he can't take any more. They all tell me that. But I take them past that point, she proudly asserted to herself.
The latest stripe just started to redden, and Deanna drew back her arm to plant another stripe. She felt a deepening of her earlier arousal as the cane made its journey to the young man's bottom.
"Owwwowww!" He shook his head wildly, unable to shake off the pain. As the pain began to intensify he thought to himself, how am I going to be able to take forty eight of these strokes?
Deanna stepped back as Angie moved in and applied several sprays of salt water to the young man's bottom. The effect was almost instantaneous. He felt as though each ass cheek was an incandescent light that had just been switched on. "Ohhhhhhhhh! Ahhhhhhhhh! Owwwww!" he exclaimed.
Deanna stepped up to take her position. She spread her legs, placed her free hand akimbo on her hip, and bent her knees in order to get the exact angle that she wanted. Her intent was that the next set of six strokes would intersect the previous set.
Whippppp! She placed a stroke so that it cut diagonally across three or four of the previous strokes.
"AHHH! NO!"
Whipppp! Another stripe diagonally across previous strokes.
"Gmlflmmmmmmmf!"
Whippppp!
"Owwwwww!"
Deanna laid three more in quick succession, with each successive cane stroke applied diagonally to the previous ones.
Angie applied the salt water spray again.
"Oh! Ohh! OHHHH! Owwww! OH-that-hurts!"
Deanna applied two more sets of six strokes in this manner, with the young man's reaction becoming more strident all along.
It's at this point, usually, that the punishment recipients believe that they can not take any more, and plead ever so fervently. During the last half of the caning, the recipient did indeed perform the expected litany of begging, pleading, and promising. Moreover, each set of stripes that Deanna applied had her getting more aroused. She suspected the same with Angie, who cheerfully applied the salt water spray after every set of six strokes.
The whipping had taken little more than five minutes. She stepped back now, placed the whippy cane in its place, and wiped a few beads of sweat from her forehead.
Now I'm so wet, Deanna acknowledged. Why does this turn me on so much?
"Very well done, Mistress Deanna. You too, Angelina. Mistress Deanna, you may be excused if you wish. Angelina and Michelle will wait here and lead this miscreant back to his room after ten minutes.
An hour later found the discipline administrators in another room which is rarely used except for very special punishment occasions. Michelle and Angie had bound the male to be disciplined face-down on a padded table. The table was similar to a massage table, except that it was significantly sturdier, and not as high. Also, the table had a circular opening a few inches wide in the center of the table. The purpose of this opening was to allow access to the male's sexual organs.
The male's wrists, ankles, and waist were securely bound to the table. Miss Karen surveyed the scene before her and determined that the session was ready to begin.
"Please proceed with the session," instructed Miss Karen.
Angie retrieved a device which was approximately the size of a small end table, unfastened its cover, and positioned it under the table upon which the male was bound. Making the necessary adjustments, she affixed a tube-shaped attachment to the device, and positioned the attachment so that the other end of the tube extended up to the opening in the table. She made sure that the tube was around the male's member, which fit quite loosely in the tube at the moment. Much of the device was constructed of transparent material so that the results of the milking could be determined.
Angie picked up a box about the size of a small book. The box had switches and knobs on it, and was the wireless control center for the milking device. She pressed a button and the machine made a whirring sound. A moment later the tube closed around the male's penis. He felt a well lubricated sheath enclose his organ, and he became instantly erect. Angie turned a knob and the machine slowly stroked the male's member. He was wondering what this was all about, since he was feeling pleasure at the time, and this was supposed to be punishment. Angie increased the rate and the machine responded.
"Ohhhhhhhhhh..." groaned the captive male, his face turning red. A moment later he exclaimed "Aauughhhhhhhhhhh! Arghhh! Ahhhhhh!" as he spurted into the receptacle. The machine kept stroking. "Ohh! Arrgh! Ahhhh!" he exclaimed with a rising level of discomfort as the machine continued to stroke his very sensitive member. When Angie was satisfied that the machine had milked him dry, she decreased the speed to the initial "idling", during which the machine still stroked, although slowly.
For ten minutes the women made small talk among themselves. When a timer signified the end of ten minutes, Angie set the stroking speed a little higher than she had on the first run. After three full minutes of stroking, the male groaned and spurted into the machine's receptacle. Angie, of course, left the machine running while the captive male voiced his discomfort at the continued assault.
After several minutes, Deanna spoke to him. "You're going to have to do better than that. If you're not going to cum I think I should spice things up with a switch to give you some motivation." She slowly and deliberately walked across the room and picked up a willow switch that had been soaking in water. She whisked the water droplets off the switch, and made her way to the hapless bound male and prepared to start the switching.
"Why aren't you cumming?" she queried.
"I did twice already!" he offered.
"You're being milked," Deanna retorted. "You're supposed to cum some more. Are you about to cum right now?"
"I can't!" exclaimed the male. Meanwhile the machine was still stroking his shaft.
Deanna briskly applied the switch to his bare bottom, at the same time admonishing him. "You really should cum. (whip! whip!) You really want to cum, don't you? (whip! whip!) I don't understand why you are reluctant to cum some more." (whip! whip! whip!)
The male being punished struggled with the pain. "Aaargh! OW-OW-OW! Please no more! Yes, I want to! I want to cummm! Ow! Ow! Please, I can't! Please stop! Please stop!"
Deanna continued in this manner for a while until his bare bottom was well marked from the switch.
Angie played with varying the speed and intensity of the stroking, increasing and decreasing the tempo like a roller-coaster. After a few moments the young man, with a vocal exclamation, ejaculated a few dribbling spurts into the receptacle. After he ejaculated, the intensity of his sensitivity to the constant stroking of the machine became especially excruciating.
Gritting his teeth with a pained expression, he exclaimed, "Aaaaahhhhh! No! Please stop the machine! So sensitive! Ahhhhhhhh-ahhhhhh-ahhhhh!"
Angie, leaving the machine running, peered into the receptacle and scolded, "That wasn't a very big load. I think it's time to escalate things here." She retrieved a specially designed anal probe. This probe had several metallic bands around it, although it was pliable and not rigid. There was a connector for a cable at the outside end of it. Angie hooked a cable to it and attached the other end of the cable to a fitting on the milking machine. Then she generously lubricated the probe with olive oil and inserted it into the captive male.
"Uhh-uhhhhh-uhhhhh!" he groaned as Angie pushed it in.
Angie then picked up the control box, turned a knob, and watched for a reaction. The probe, as a result, expanded and contracted in a pulsating fashion. As it did this, it pressed against the male's prostate, stimulating it. Angie observed the male's facial expressions as she varied the speed of the pulsing, looking for the tempo providing the most stimulation. When she found the right setting, she left it as it was and waited. A few more minutes, and the male again shouted out an exclamation and dribbled some more semen into the receptacle.
"Arrgh! Arrrrgh! Aaaaaaarghhhh! Oh, no! I can't!. Please stop! Please stop! Aaaaaahhhhhhhh!"
Angie waited a few minutes before stopping the pulsating of the anal probe. She did, however, leave the milking machine stroking his member. Looking into the receptacle, she expressed mock disdain. "Just a dribble this time. I thought I could get more from you. Oh well, I'll just have to employ other means. Maybe Mistress Deanna should give you another switching."
"No, not the switch! Please, I'll do anything!"
"Anything? All I'm asking for is a nice big load of cum."
"I try! Really! I just can't! Please! I'm completely drained!"
"Then you'll have to take the consequences," teased Angie with a coy smile. She seated herself, calmly crossed her legs and picked up the control box. She started the anal probe pulsing again, and adjusted the speed as before. Then she pressed a small red button on the box. This caused an instantaneous pulse of electricity to course from the male's prostate to his sphincter. To him, it felt like a hot pin-prick to his sphincter, and similarly inside him at his prostate.
"Oh! Ohh!" he cried. Angie pressed the button again. "Ow! Ahh!" Then she continued to press the red button at random intervals every few seconds. When Angie sensed that he was nearing another ejaculation, she rapidly pressed the button a couple of times per second until the male violently shook his head back and forth with gritted teeth.
"Yaaaaaah! Oh, the pain! That hurts! Aaaaargh!" he yelled as a rather empty ejaculation wracked his body. "Mercy, please! I can't! Oh have mercy!"
After a few more minutes of the machine's stroking, Angie finally turned it off. The bound male was now drenched in sweat, groaning and panting.
With a smile, and very aroused, Deanna walked out of the room and went to her office.
Mistress Deanna left work at 10 PM and headed home. Throwing off her clothes, she got in bed with her lover and waited a few moments. When he stirred, and was still half-asleep, she guided one of his hands to her aroused womanhood. Sleepily he stroked her clitoris and labia. As he awoke he felt himself becoming erect.
"What did you do this time?" he inquired, stroking Deanna's profusely lubricated pussy.
"Ahhhh! Ahhhhh! A severe strapping, a very severe caning and a milking," she whispered.
"Were you turned on?" he asked.
"Ahh! Yes! Ahhhh!"
"You nasty bitch! You're getting me hard!"
Deanna climaxed with raucous groans. Her lover threw off the covers and he pulled her on top of him. He quickly entered her and he held on tightly with his arms around her. "Come on, you cunt! Ride me! That's it - yes, you're a nasty girl!"
Deanna, her eyes filled with fiery passion, began to furiously pump with her hips. While she was doing this, she taunted her lover. "Rick, I've warned you before about your language. You know what, Rick? Tomorrow I'm going to tie you down and give you a strapping just like I gave tonight! I'm going to watch your ass cheeks quiver and jiggle as they turn fiery red. And you're also getting a dose of the forehand-backhand thing! Oh God, Rick, I'm gonna love it! You, on the other hand, are going to be begging for mercy! Ahhh! Ahhhh! Ahhhhh!" Deanna climaxed again and felt her lover's erection stiffen even more inside her.
"Deanna!" exclaimed Rick. "Aaahhrgh! Mmmmmmff! Uhhhh!" He thrashed about as he spurted inside of Deanna.
When the passions had subsided, Deanna whispered, "I meant what I said, Rick. You ARE getting that strapping tomorrow."
Rick brought Deanna's mouth to his and kissed her passionately. "Mmmmmmm, Deanna, I love you!"
- end -
----- I hope you enjoyed this story. I enjoyed writing it. This work is copyright by the author. Commercial use is prohibited without permission. Archiving and reposting of this story unmodified is permitted provided that no fee is charged, either directly or indirectly (including so-called "adult checks") and provided that this disclaimer and attribution to the original author (rick_oh at email.com) are maintained. My other stories can be seen at http://www.asstr.org/~rick_oh/
Cheryl
- 28.07.2021
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