Her Overseer: Don’t Piss Off your Owner (Her Client Trilogy Book 2)

by Richard Verry

  “Oooowwwwwwwww”

  The agony radiating from her ass seemed to traverse her entire body. Jerking this way and that, her body bounced around against its restraints. She couldn’t control it. It just hurt so bad that she just wanted it to stop.

  Screaming for who knows how long, all thoughts of pleasure were replaced by the agony of pain. Her thoughts shut down. Her mind went blank. All she could feel was the agonizing electrical energy released deep in her rectum.

  When it finally stopped, her body strained under the current, suddenly collapsed. With nothing happening in her mind, everything went blank and she passed out.

  ***

  When Jolene came to and consciousness returned, she opened her eyes and looked around. With her head still locked in place by the harness, she could see that Jon had left her field of vision. Grabbing the moment to investigate her surroundings, she noticed she was in a large room. The walls were in the shadows but she could tell that they were thick rock or concrete. Any hope of someone hearing her were dashed when she realized that the room she was in wouldn’t allow any sound to escape.

  Scanning further, ahead and to the left, she saw a large table with various items on it. Since it was in the shadows, she couldn’t make out just was on it but she presumed that they were instruments of torture. What bothered her more was that they were piled high with numerous items of various designs and styles.

  “Oh, fuck me” she thought to herself.

  To the right of her field of vision, she saw various pegs mounted to the walls. Hanging from the pegs were more items. These looked to be floggers, whips and such stuff. Squinting, she could make out a bullwhip, several smaller single tail whips of various sizes and lengths, various floggers and even a couple of cat-o-nine tails. Some of the floggers and cat-o-nine tails had studs or similar stingy things on their tips, making her think that now only would they hurt but they would injure her.

  “Oh, fuck me again” she cursed to herself.

  Just as she said that, the dildo up her pussy began vibrating and fucking her again. Learning from her earlier experiences, she resisted the urge to enjoy the sensations of the vibration against her clit and against the inner depths of her pussy. It was hard but she seemed to make headway.

  As the vibrations went on though, her concentration began to waiver. Her body was exerting itself, demanding the pleasurable release it had so far been denied. Her controlled breathing still held its own but it was most definitely wavering.

  Trying to find out where Jon was, for surely, he must be watching her. He had to be waiting for a moment to strike and make her pay for her pleasure, she thought. Jolene wasn’t able to figure out where he was, but he had to be close.

  The exercise of trying to find him, starved off her building excitement but it only lasted so long. Her control was weakening and her body was taking control. As she detected the signs of an imminent orgasm built, she yelled out loud “Fuck!”

  Chapter Eight

  It was really interesting to Jon to note how transparent this cunt was. Consciousness had returned to her but once again, she was trying to hide it. Standing still behind her, he watched to see what she would do.

  A minute or two after awakening, she must have thought he wasn’t around. She had opened her eyes which darted back and forth, looking around for him. Failing that, she began assessing her situation and environment. At first, she took in her surroundings. At least as best as she could, seeing how her head was still harnessed to the fucking machine.

  He was proud of this latest version of the machine in his collection. The remote features it offered, all with a simple wireless remote connection were astounding. Plus, it could be programmed with all sorts of accessories, such as the electrified butt plug still stuck up the cunt’s ass.

  “Man that was fun. I don’t think I’ll ever tire of that accessory” he thought to himself with that pleasing notion of an unexpected discovery.

  Returning his attention to the cunt strapped down before him, he noticed that she was staring in disbelief at the table on the far side of the room. The table that contain so many of his toys.

  “I can only guess what’s going through the cunt’s mind right now” he thought to himself.

  The table was piled high with all sorts of gags, knives, needles and similar tools with which to inflict anguish and pain. Not that he had much use for gags seeing how much he enjoyed their screams. Still though, they came in handy at times. Talking was so overrated.

  Eventually, she discovered the racks of his whips and floggers, dangling from pegs along the wall. He had over a hundred of various sorts, each designed to bring out the best in screams.

  “Some barely left a mark but elicited such lovely screams,” he thought. “Others, hurt but could easily part the skin, leaving wicked bleeding marks.”

  He liked to paint his canvases with these whips. As he painted, he strove to create works of arts using the stripes flayed across the flesh in intricate patterns and imagery. Sometimes, his efforts resulted in beautiful works of art. Unfortunately many did not live up to his high standards and were summarily discarded. Those that did result in exquisite works of art were another matter altogether. He had their hides stripped from their bodies, preserved and framed. They currently were on display in his trophy room. It remained to be seen whether this cunt’s hide would grace his trophy room or just be discarded.

  “Enough of that” he thought to himself as he pressed a button on his remote and activated the Sybian she still straddled.

  The dildo began it’s in and out movement in her pussy while the vibrator teased her clit and cunt. He was pleased to note that she responded instantly, realizing that he must be nearby.

  Watching her body language, he could see her attempts to suppress the pleasure the device was designed to give her. A futile struggle he knew. The machine would work tirelessly, indefinitely to achieve the goal of bringing about orgasm after orgasm to the rider.

  “Oh, yes, she will orgasm on that thing. Many times over” he thought gleefully.

  Each time she did, she would earn an additional punishment as he would withhold his permission for her to cum.

  “Oh, the beauty of her predicament. To be punished for cumming.” He smiled to himself while rubbing his hands together in anticipation of the coming punishments.

  Chapter Nine

  “Oooooooo” that’s feeling so goooooddddd. But I’m so fucked.”

  Jolene thought as the Sybian continued to bring her closer and closer to orgasm. Realizing that her climax was imminent, she remembered what he had told her.

  “Please Sir. May I cum?” she begged, her breathing getting more and more erratic.

  She only heard silence. “Fuck” she thought to herself.

  “Sir, may … I … please … please … cum?” she begged more emphatically.

  Still, all she heard was silence.

  Biting down on her lower lip, she tried to suppress her body’s natural response to the fucking machine. It worked for a moment but soon, her building climax resumed its urgency.

  “Oh, fuck me” she bitched to herself.

  “Please … Sir. May … I … please … oh … please … may … OH … may … I … cum?” she begged once more.

  Silence was her only answer. But without a way of stopping the inferno machine, she had lost all control over her body.

  “Aaaaaaaaahhhhhhhhhhhhhhhhh” she breathed out as her body began jerking around in its climax. Cumming long and hard, Jolene gave up all control over her body and allowed it to continue.

  Later, as she came down from her orgasm, she realized, she was royally fucked. For sure, he would punish her. And still, the machine continued to fuck her pussy while her body starting building to another orgasm.

  “Oh, fuck me” she muttered.

  Unable to stop it and before she could ask for permission or beg for forgiveness, a second climax hit her, even stronger than the first one.

  Riding the waves of pleasure rippli
ng throughout her body, a slice of her mind knew that she was going to pay dearly for this infraction. “What was she to do? Either way, she was screwed.”

  Having lost the battle to stop her climaxing, she gave in to the relentless dildo, fucking her pussy while vibrating her clit. She gave in and accepted yet a third orgasm pulsating through her.

  Breathing heavily and erratically, she took the pleasure for what it was worth. Perhaps it would soften the beating she would soon take in punishment. Realizing that she could not avoid punishment for this infraction, she gave in to the artificial fucking her pussy was getting and decided to embrace it.

  Several minutes later, with the speed and intensity constantly changing encouraging her to climax, Jolene gave in to climax after climax, enjoying each one.

  After she had lost count of the number of times she came, she began noticing that her body was no longer feeling the pleasure that would trigger an orgasm. Instead, her pussy and clit were getting dry and sore. In fact, real sore, painfully sore and painfully dry.

  “Oh, shit” she realized out loud.

  This is how he is going to punish me. He’s going to keep this goddamn fucking machine going while I scream in pain. “Oh, my God. Please help me!” she begged.

  And still the machine continued fucking her.

  As time went on, the soreness shifted to stinging and then on to full outright pain. She grimaced and tried to ride it out. However, that didn’t stop her from trying to get off the blasted thing.

  Still the machine relentlessly continued its designed function.

  “Arrgggghhhhh, Arrgggghhhhh, and Arrgggghhhhh” she screamed over and over and over again.

  She screamed until all went black.

  Chapter Ten

  Pleased by her response, first begging to be allowed to orgasm and then screaming in response to the continuing painful torment a dry and sore pussy being fucked, he let her scream until she passed out.

  Satisfied so far, he prepared her for the consequences of her infractions. Unstrapping her from the bondage device, he dropped her unconscious body carelessly off to the side and moved the device out of the way.

  Removing her arm binder, he tied her wrists together in front of her, careful to make sure he didn’t pinch one of the many nerves coursing through her wrists. Pinching the nerves would be painful at first but after her hands went numb, she would suffer permanent damage and he would no longer be able to use them as a means to inflict more agony on her. Better to make sure they remained viable for now.

  Grabbing her by her wrists, he dragged her unceremoniously over to another area of the room. Pulling down a winch hook, he looped her wrist bindings onto the hook and lifted her up into the air, stopping at a point where her toes were hanging just above the floor.

  With the cunt hanging by her wrists, rotating slowly as the winch rope settled under its burden, he prepared himself for his next tasks.

  Pulling a chair over, he sat down to wait until she came to. It was over an hour before she did so.

  Chapter Eleven

  As Jolene regained her senses, she realized that she was no longer strapped to the fucking machine. In fact, she was hanging by her wrists from a hook mounted from the ceiling. Her body ached from the strain. All of her joints seemed to be protesting the new position. Each felt like they were being stretched like they had never been stretched before.

  Wiggling her toes, she couldn’t feel the floor underneath her feet. Lifting her head, she immediately located Jon, sitting in front of her.

  “I’m … sorry … Sir” she managed to croak.

  “Cunt, you disobeyed me several times. For each infraction, you will suffer the consequences of your actions” he replied.

  “Sir, please … Sir. I’m … sorry. I … I tried to obey. I … did … ask … for … permission.”

  “And did you get it?” he asked.

  “Ah … no … Sir. I’m … sorry.”

  “No, you didn’t. And still, you chose to cum anyway. There is no excuse for your blatant disregard of my orders. You will be punished for your indiscretions.”

  “Sir, please Sir. I tried. I … really … tried” she croaked begging forgiveness between her crying sobs.

  “That is no excuse, cunt. Now shall we find out what your first punishment will be?”

  “First, Sir?”

  “Yes, first. Don’t you remember how many times you disobeyed me?”

  “Ah … no … Sir. Three?”

  “Hah. Three. No. Six times you allowed yourself to cum. Six. So, six punishments is what you will suffer. You already were punished once before you passed out, so you have five to go.”

  “Shall we start?”

  Resigned to her fate, Jolene dropped her head to her chest and waited. Still, she could see enough to watch Jon walk over to the three bowls. Reaching into the first one, he pulled out a scroll and opened it.

  ‘Cane’ it read.

  Sighing, she dropped her eyes in resignation.

  ‘Thighs’ read the next scroll. “That’s not so bad” she thought. She would find out later just how wrong she was. Waiting for the count, her mind raced with worry.

  Not wanting to see what was written on the last scroll, she heard him read it to her.

  ‘Thirty’

  “Fuck” she muttered to herself as he walked over to the wall and selected a long whippy cane hanging from a peg.

  “You will count out each stroke as you receive your punishment. Is that clear?”

  “Yessss … Sir” she said hesitantly.

  “Good, very good. We will begin.”

  Gulping, Jolene did the best she could to prepare herself for the first of thirty sure to be very painful strokes. Stepping back, Jon quickly waved the bamboo cane several times. The disturbed air made that swishing sound that she came to hate. Approaching her, he took the cane and stroked it across her thighs as if it were a violin bow. Just the touch of the cane on her thighs filled her with trepidation. Her level of fear seemed to grow with each caress of the cane.

  A couple of times he pulled the cane back and began a harder swish towards her. Prepared to be struck, he stopped it from hitting her just millimeters from her skin. With each of the pretend strokes, Jolene yelped as if she had been struck only to realize afterwards, that he had faked her out.

  Alternating between playing her thighs as a violin and faking a strike, Jolene’s trepidation grew exponentially. She began to whimper and cry long before the first strike.

  ‘SWISH’ followed by “Oooowwwwwwwww” as the cane smacked her hard across her thighs.

  Immediately, a red welt appeared and the sting elicited a loud yell from her mouth. If Jolene was able to, she would have doubled over from the pain. Hanging there like slab of meat, her gut tightened and she drew her legs up towards her waist, then slowly lowering them as the pain subsided.

  “I’m waiting” she heard him say. “Don’t make me repeat myself” he added.

  “Ummm … One.”

  “Oooowwwwwwwww” she yelled as the cane came swishing across her thighs again.

  After a moment to process the strike, she uttered “Two”, tears streaming down her face.

  Toying with her, she watched him walk around her, swishing the cane back and forth but not connecting.

  ‘SWISH’ followed the sound of the cane as it again struck her thighs a third time.

  “Oooowwwwwwwww” was the response. Slowly she uttered … “Three.”

  On and on the caning went. Sometimes, there were short pauses between strikes. More often though, he waited a long time before he struck again, seemingly enjoying her misery as she screamed. A couple of times, she took too long to count off the strike and he repeated it, adding to the total number of strikes to her thighs.

  By the time it was all over, she was too weak too even support her own body. She was a quivering mass of gelatin, crying from the painful caning and of despair. The pain to her thighs was so intense that she shuddered to even look at them, afraid to
see the damage left behind. They burned and screamed as nerves under her skin demanded relief from the multitude of welts striping across both her thighs.

  Eventually, she remembered his instructions. Without looking up at him, she said while still crying profusely. “Thank you … Sir for … the punishment … I so … rightly ... deserved.”

  Looking over at Jon, she noticed he had taken a seat in a chair and seemed to simply be watching her.

  “Well, screw him!” She thought.

  Seeing him there, gave her the strength to look down at her legs. Tilting her head as best as she could, past her breasts and belly, she saw that her thighs were covered with dozens of angry welts, scary and red. She cried for them yet not from the pain but from her inability to protect them from his onslaught.

  Crying for them, gave her the strength to continue. She resolved that if she could find a way out of this, Jon would be dead. She was going to kill him and then she was going to kill Jeremy. Screw the consequences. She vowed to kill them both, no matter how long it took.

  Chapter Twelve

  As Jon delivered each stroke of the cane, he watched her pearl white skin slowly transform, crisscrossed with angry red welts. More importantly, he delighted in her misery and in her screams. Over and over he struck her and over and over she screamed. “It was glorious.”

  Even better was when the cunt forgot to count the stroke. That enabled him to repeat the stroke, adding to her misery. “Wonderful.” Even better, she miscounted a couple of times, repeating a number. He of course did not correct her. He just struck her again, picking up from her last incorrect count.

  When he was done, her tears streamed down her face and naked chest. Her tits were soaked with tears and sweat, while her thighs were painted with crisscrossing welts. The canvas of her thighs were a landscape painted by his brush. “Beautiful.” And she had remembered to thank him for her punishment. That had surprised him. Most of the others had forgotten this little sign of respect he demanded after such a caning.