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

  And with that, and with his bare hand, he slapped her face hard. Hard enough that despite the straps holding her head immobile, her head snapped at the impact. She immediately began crying from the blow.

  She hadn’t recovered from the first blow when the second hit her on the other side of her face, snapping it back again. After the remaining blows had finished striking her, her face was red and burning. Her jaw felt like it had been dislocated though when she flexed it, it moved normally, if not painfully. She was crying profusely with tears, drool and slime dripping down from her nose. Was it broken? No, she didn’t think so.

  “I’m waiting” she heard him say.

  “I … I .... Sir … thank you … for … my … … punishment” she croaked out between sobs.

  “Jolene, I must ask you. Did you deserve it? Answer me truthfully.”

  “I … don’t … know … Sir” she began and before he could interject she continued “... but if … you … think … I … did … then … I … I deserved my … punishment” she completed saying between her sobs.

  “Very good. You answered correctly. I wasn’t sure you could do it but you pulled it out at the last moment.”

  Sobbing uncontrollably, she mumbled out “Thank … you. Sir.”

  Chapter Four

  Well, she’s learning how to behave, perhaps too quickly” Jon thought to himself as the crying bitch begged his thanks. “I might have to step it up a notch, I think.”

  Pausing to consider this thought, he went on. “I’ll give her this much. She’s intelligent. Most bitches who first come to me, take a full day or more to finally understand and abide by the rules.

  After tossing the three scrolls into the trash, he turned towards her and stood watching her. She had arrived balled up, gagged and blindfolded. Did she not know who sold her to him? He was disappointed that he had let that little information slip. He knew immediately that when he mentioned Jeremy’s name, she reacted in disbelief. What else had Jeremy learned since his last purchase from him? He would have to keep a closer watch on him. He might just be up to his standards after all.

  He had to admit. He liked his last acquisition. Jeremy had done well finding this one. It was obvious to him that she had gone through an ordeal before she was balled up and sealed up in the duffel bag.

  His knot tying was getting especially good. He hated to cut the ropes off her but for many of them, he was unable to untie the various knots he had used. He especially liked how her arms had been bound behind her. It was obvious to him that she hadn’t been bound in an arm binder before, her elbows lashed together behind her back. Her face clearly expressed the pain she felt, even when she was unconscious.

  After he had unballed her, he left her arm and leg bindings on for a time. Lying on her belly, he could admire the long clean lines of her body, her arms stretched out along her spine. So many like to bind their legs while crossed at the ankles. While this made it harder for them to escape, it disturbed the clean lines. He liked what he had seen and was looking forward to adding his own fun.

  After he had finished cutting off her bindings, he bound her to her first instrument of torture. He would start off slow and easy before building up to something more intense. The bondage device he placed her in would give her both pain and pleasure.

  First, while she was still unconscious, he had sat her down onto a dildo attached to the Sybian machine. Later while they played, it would give her pleasure while he gave her pain. As he positioned her in the device, he also inserted and strapped in a large butt plug. Attached to the butt plug were wires that led to an adjustable transformer that would give her unbearable torment.

  Sitting her body up, he pulled her arms behind her back and fed her arms into a leather arm binder and laced it up. Knowing that she originally arrived with her arms bound with rope in a similar fashion, he ensured that as he laced, he pulled her arms tightly together so that her elbows were once more held firmly against each other. After he secured the arm binder straps over her shoulders, he lifted her arms high and attached them to the bench behind her.

  Lastly, he strapped the harness to her head. The harness was in turn attached to an actuator of a mechanical fucking machine bolted to the bench behind her head. When activated, the actuator would push her head back and forth at varying speeds, from slow to blinding fast at his discretion. The controller for the actuator was in his pocket. She was ready to go.

  He had to admit, he would enjoy punishing her. Even though this first round was going to be mild, he was looking forward to the next few days as the intensity of his torment steadily increased. Gazing at her, her sobs changing to whimpers, he slowly hung up his suit jacket and rolled up his sleeves.

  “Time to get started” he said as he strolled up towards her and pulled down his fly.

  Chapter Five

  Jolene’s face hurt. The stinging slaps resonated throughout her head, scrambling her brains. “Was that really only ten?” she asked herself.

  He could really hit. If it were anyone else, she’d be feeling a bruise forming. With him though, she expected that he had enough experience that he knew how to minimize damage.

  “All the better to hurt me some more” she thought.

  As she cried herself to a whimper, she tried to prepare herself for what was sure to come. Somehow, she didn’t believe she could prepare herself but she would try.

  Opening her eyes, she saw him taking off his suit jacket and roll up his sleeves. “What was he doing?” she wondered.

  Then, as he turned towards her, she saw him smile and walked towards her, opening his fly as he approached. Pulling out his cock, he stepped up in front of her and placed it in her mouth.

  “You know what to do” he commanded her.

  “Yes Sir. Thank you Sir” she responded with a gravelly tone being that there was a semi-rigid cock resting on her tongue.

  Closing her lips around him, she began sucking him off, stroking her tongue on its sensitive underside. Jon just stood there, watching her attend to him. Every so often, she would look up at him and try to see if she was having an effect. Sure, his cock grew easily, almost too easily. She had to wonder what surprise he had in mind for her as she sucked him off.

  Straddling the saddle like thing, with the dildo shoved up her pussy and the butt plug in her ass, she struggled to service the cock. Except for her mouth, she couldn’t move. How was she going to suck him off if she couldn’t use her hands or any of the other techniques she commonly used to bring her partners off? And what was this harness strapped to her head. It prevented her from pushing her head onto him, drawing him deeper inside.

  What she did know was that he expected her to do her best to make him happy. With what little she had to work with, she would do her best. Assuming of course, that he wanted her to do exactly that. She hoped she was right.

  With his growing cock resting on her tongue, she used it and her lips to caress and her lips to suck on his cock as best as she could. “Couldn’t he at least move a little? Shove it in? Help me out?” she thought.

  Chapter Six

  He had to admit, given her limited resources, she was doing a fine job sucking his cock. Basically, all she could do was suck and massage him, flex her jaw while stroking him with her tongue. He allowed her to struggle for some time, enjoying the strain she was under trying to perform.

  “Her struggles would be in vain” he thought to himself. It would take much more than this to bring him to climax. In time, she would learn. For now, he simply would let her do her thing. In the end her eyes would water, not from crying but from gagging on his cum shooting down her throat. Intrigued, he let her continue to see how far she would go to please him.

  Standing very still in front of her, she went several minutes before showing signs of weakening and the subsequent frustration.

  “Keep it up, cunt” he ordered her.

  “Grummppphhhh” she responded, renewing her efforts with a bit more success.

  At least she had gotten
him rock hard, a sensation he craved. He still hadn’t felt the back of her throat or had the head of his cock embrace her soft palate. For the moment, he didn’t care. Her tongue was hitting all the right spots on the more sensitive underside of his cock.

  As he began to get bored with her lame manipulations, he reached into his pocket and pulled out the controller for the fucking machine attached to her head. Without showing her the controller, he placed his thumb on the UP ARROW key and pressed.

  Catching her by surprise, her head was pushed forward onto his cock driving it deep into the back of her mouth. Not expecting the action of her head suddenly pushed forward, she immediately gagged on the intrusion of his cock down her throat. Her body heaved and her chest expanded as if to vomit. With her body restrained as it was, she coughed and slobbered all over his member, spitting up saliva and slime on his trousers and shoes.

  Selecting the DOWN ARROW on the controller, her head was pulled back until his cock barely rested on her lips. Coughing, the cunt slowly regained control of her body. Stretching her tongue out, she tried to flick the underside of his cock.

  “Very good, cunt. Nice recovery. Before long, you won’t need to recover at all. You’ll accommodate me without any difficulty. You just need practice and I will make sure you get it.”

  “Yes, Sir. … Sorry Sir” she answered him.

  “And?” he queried as he had not gotten the full correct response from her.

  She took a moment to consider his request before she responded. “Yes, Sir. Sorry Sir. May I have some more?”

  “Well, that’s better but you still didn’t thank me for my gift.”

  “Sorry, Sir. Thank you.”

  “Too little and way too late. That’s an infraction for which you will need to be punished. Also, you got spittle all over my trousers and shoes. That’s a second infraction that requires punishment.”

  “Sir, I’m sorry Sir. I will do better.”

  “Oh, I’m sure you will.” Pressing another button on his controller, he said. “One.”

  She instantly reacted to the electrical shock radiating from the butt plug in her ass. She screamed a very satisfying scream that continued well after he had let go of the button.

  “Oooowwwwwwwww” she screamed loudly, her body stretching as if to expel an evil stored within.

  As she finally began to settle down from the pain in her ass and as her screams diminished to a whimper, he pressed the button again and said “Two”.

  “Oooowwwwwwwww” came the sound of her resuming her screaming.

  As he held the button down, knowing that the electrical current was only strong enough to hurt but not damage, he watched her reactions. Would she clamp her mouth shut at the jolt or would she open her mouth wide with the bloodcurdling scream. He was pleased to note that she opened wide with the scream.

  “Hmmm, good to know” he thought just in case he shocked her while his cock was deep in her mouth. “Would she inadvertently bite his cock off?”

  Releasing the button, she recovered a bit more quickly this time. Whimpering, she offered him a bit of compensation.

  “Sorry … Sir. … I’ll … … do … better next … next … time” she groveled.

  “Oh, I’m sure you will” he said as turned the fucking machine back on, forcing her to bury his cock down her throat.

  Playing with the controller, he began adjusting the controls so that her head began bouncing back and forth, alternately driving her head onto his cock before withdrawing it. He also played with the speed of the device, so that at times, she would be driven slowly onto him while at other times, her head snapped back and forth in a blur.

  It was all she could do not to choke. When he quickened her pace, she was barely able to do much more than open her mouth wide and let his cock slide back and forth across her tongue.

  When he slowed the pace, she actually tried to wrap her lips around him and suck him off. The in and out motion relieved her of working her jaw so all she had to do was to keep the pressure of her lips and tongue on him.

  Occasionally, he would stop the ram completely, sometimes burying his cock deeply down her throat and at other times stopping just inside her mouth. At these times, she massaged him as best as she could, which was no small feat in of itself. She was forced to extend her tongue in order to maintain contact on the soft sensitive underside.

  It took about twenty minutes or so but he finally began to feel a climax building up inside him. Adjusting the controls of the fucking machine, he set the throw action in half so that he was always buried deep in her mouth and throat, never pulling him even half way out of her mouth.

  As the underside of his cock continued to slide along the length of her tongue and the rhythmic motion of his cock head sliding down her throat, his climax built and built. It didn’t take much more of an effort before he had stopped the machine and drove himself forcefully down her throat. Feeling his cock swell up, he exploded, shooting hot creamy gobs of cum. Fighting the trembling in his legs as he climaxed, he further drove his groin into her face, forcing his rippling cock against the soft tissue of her throat, coating it with his cum.

  After his climax, he pulled partially out and rested it against the top of her tongue.

  “Clean it cunt” he commanded her.

  Between her gasping breaths, she sucked it clean. When he was satisfied, he stepped back and waited.

  “Thank you … Sir for your … gift of … your cock and cum” she offered between choking breaths of air.

  “Fair job. I’ll give you that. I will give you a reward. What do you think about that cunt?”

  “Whatever you wish … to give me … Sir, I … thank you for your … gift.”

  “Nicely said” he answered her. Touching yet another button on the controller, the Sybian turned on and began vibrating the dildo inside her and against her clit. At the same time, the dildo began driving in and out of her pussy in a twisting motion. Between the vibrations and the added fucking motion, the machine’s design was to quickly bring her to orgasm.

  Her body immediately responded to the pleasing stimulation, clearly enjoying it.

  Chapter Seven

  “Fuck, what kind of contraption was that?” Jolene considered. “I didn’t know it was going to thrust my head forward like that. I was totally unprepared for his cock suddenly being forced into the back of my throat.”

  After she had recovered from the sudden onslaught of her head being pushed forward with his cock buried in her mouth, she involuntarily gagged on it. It is one thing when I know it is coming. I can prepare myself for it.

  “This, fuck, I had no idea he could do that.”

  One moment, I’m reaching out massaging and sucking him. The next, I was choking and about to upchuck all over him.

  Not that I had much in my stomach since I hadn’t eaten in almost a full day but that didn’t stop me from spitting up and messing his shoes and trousers. And then fuck it all, the punishment he gave me!

  “I never knew I could be in so much pain. When he turned on that awful butt plug, a jolt of electricity lit me up like a Christmas tree. I don’t remember much after I started screaming. What I do remember is Jon doing it to me not once but twice.”

  “Does he really get off on torturing me?” she asked herself. “Apparently so.”

  After that was over, he resumed bouncing my head on his cock, though he alternated the motion and speed of my head jammed on his rigidity. For a while there, I thought the machine would snap my head clean off my body. When he came, just like with Jeremy last night, all I could do was bear it, hold my breath and hope to high heaven that I didn’t suffocate.

  After I cleaned him up and he put his cock away, he told me that I did a fair job. “Fair?” she questioned in disbelief. “Fair, I think I did a mighty fine job of it. Fair? Give me a fucking break.”

  “Fair job. I’ll give you. I will give you a reward. What do you think about that cunt?” He had said to me.

  Careful
to select my words as I really didn’t want to get shocked in my ass again, did I have a choice? I answered him hoping beyond hope that I gave him what he wanted.

  Cautiously I said. “Whatever you wish to give me, Sir, I will thank you for it.”

  Apparently, it was the right response. A moment later, the dildo stuffed up my pussy began vibrating and pleasure began to flow through me as it fucked my pussy.

  “Hmmmm that feels good” I muttered to myself.

  Jolene knew that the pleasant fucking, artificial as it was, wouldn’t last long. After all, hadn’t Jon promised that she would be screaming for him? That may be so but what’s to stop me from enjoying myself, even it’s for just a little bit. With determination to do exactly that, she pressed herself onto the vibrating dildo and adjusted the vibration to maximize its effect on her clit. As her breathing became more irregular, taking deeper breaths as the moments went by, she felt her body respond. Enjoying herself, she felt the coming orgasm build in her gut, the dildo fulfilling its designed purpose for existence.

  As the climax built, she hoped that he would allow it to complete itself.

  “Are you ready to cum?” he asked her.

  “Uh, uh” she managed to vocalize.

  “Ask me” he commanded her.

  Not knowing what he meant, she probed her memories and experiences hoping to find the answer. She failed while her building orgasm progressed along its approaching finish.

  “Sir, I … I’m sorry. I … don’t know what you … want.”

  “Ask me if it is alright to cum, cunt” he answered rather sternly.

  “Sir … what?”

  “You may not cum without asking permission. For making me repeat myself, you have incurred an infraction.”

  And just like that, he turned on the juice in her butt plug, electrifying her ass. In an instant, her building orgasm was gone to be replaced with unspeakable pain. Unspeakable of course except for her screaming.