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

by Richard Verry

  Sitting down on his chair, he crossed his legs and gazed upon her naked body swinging from the hook above. She continued to cry for several minutes, her chest heaving from the wrenching pain. As she seemed to bounce on the end of her tether, he wondered if she would pass out again. Not that he cared but he wasn’t in the mood to take a break.

  Enjoying her misery, he continued to watch.

  It was some time later when she tilted her head up and looked in his direction. Expressionless, he waited to see her reaction. Observing her, a shadow of defiance passed over her face. Her eyes went cold, cold as his were. Keeping her emotions in check, he wondered what she was thinking.

  “Was she planning her escape? Was it something else?” he wondered. “Well, no matter. The cunt was not going to escape and she was going to die a glorious death.”

  Standing up, he walked right up to her and began caressing her cheek as if with an air of compassion. Combing her hair behind her ear, he continued to stroke the side of her face. He enjoyed the softness of her skin, soaked with her tears. Her hair was damp and he liked that even more. Perhaps later, he would water board or drown her. “That could be fun.”

  As he caressed her cheek, he looked for any softening of her expression. Truly, he hoped she wouldn’t. All the more fun to break her. So far, she hadn’t broken. What would he do next? The scrolls would tell. It was time to find out.

  Suddenly, instead of caressing her cheek, he swung out and slapped her firmly on the side of her face. The stinging slap caught her off guard. Stunned, her cheek turning red and tears welling up in her eyes once again, she stared at him in stronger defiance. “All the better.”

  “Are you ready to continue?” he asked.

  “No, Sir” she responded.

  “No? That’s surprising. I like the honesty though. Well, enough of a break. Shall we find out together what your next punishment will be?” he told her as he walked over to the scrolls.

  “Let’s see. Six infractions, three punishments. Let’s find out what’s next.”

  “Three Sir?”

  “Yes, I’m counting the slap as one of the punishments. You’re welcome.”

  “Thank you … Sir.”

  “Just remember, good behavior will go a long way with me. Of course, you still have a long way to go to repay your debt. Shall we?”

  She hadn’t answered him of course. He expected that. Her continued defiance only spurred him on.

  Reaching into the first bowl, he extracted the first little scroll. Showing it to her, he slowly pulled the ribbon off and unrolled the paper.

  It read ‘Breasts’.

  Smiling, he looked at her and said. “Oh, this is wonderful. I was hoping that you would pull this one.”

  Turning, he pulled a scroll from the second bowl. Untying it and showing it to her, he allowed her to read it before he did. Her look told him exactly what it read.

  Turning it over, it read. ‘Single Tail’.

  Pulling the last scroll from the bowl, he untied the ribbon, took a long look at the number on it and broadly smiled. Turning it towards her, he allowed her to read the number.

  It read ‘50’.

  Sighing, her head dropped in resignation.

  “Let’s begin. The sooner we start, the sooner it will be over.”

  “Yes, Sir … thank you Sir” she mumbled under her breath but loud enough for him to hear. Her defiant tone turned to resignation and acceptance.

  “Oh, this is going to be so much fun. Let’s play.”

  Chapter Thirteen

  “Fifty, oh my fucking lord. Fifty lashes with a single tail on my tits. Oh, shit!” Jolene said over and over again in her head.

  She had cried for her legs, her beautiful legs that she showed off with her miniskirts and stilettos. She might not ever wear short skirts ever again. She was certain that she would be scarred for life from the welts of the caning.

  And now, he was going to attack the best part of her body, her breasts. How would they look after the whipping? Would they even have any feeling left afterwards? Would a simple caress of their delicate flesh raise goosebumps in anticipation of pleasure sure to come? Or would they forever remind her of this whipping and hurt like hell from the slightest touch?

  “Fuck me now!” she lamented in her head.

  Watching him closely, he selected a snappish whip, about four feet long. At its tip was a short little string ending with dozens of split ends. As he flicked it, testing its action and hearing the crack as the short little string broke the sound barrier, she thought.

  “Oh, shit. That thing looks nasty.”

  As he walked quickly up to her, flicking the whip back and forth, he snapped it right across her right breast and nipple without any warning.

  “Oooowwwwwwwww” she screamed, sucking in her gut in a vain attempt to minimize the damage.

  ‘Crack’ came the sound of the whip as it connected with her left breast and nipple, again without warning.

  “Oooowwwwwwwww. Oooowwwwwwwww” she cried relentlessly.

  Eventually, she said. “Two.”

  “One” he corrected her. “You failed to call out ‘One’ after the first stroke. So, I had to repeat it as a reminder to count each stroke as they are delivered.”

  Nodding, she uttered “One.”

  “Good.”

  ‘Crack’ sang the whip as it connected with her left breast, almost right on top of the last stroke, multiplying her suffering.

  “Oooowwwwwwwww”

  Sucking in her breath, she managed to croak out “Two” before he could wind up for another stroke.

  ‘Crack’ sang the whip again, landing on her right breast.

  Crying hard, it was getting more and more difficult to mark the count but she managed to say “Three” just in a nick of time.

  Giving her a chance to recover, he held off the next stroke for a bit. As her breathing returned to normal and her crying changed to a whimper, he cracked the whip across the top of her left breast.

  Screaming, she managed to count “Four”.

  And so it continued. As before, Jolene had no concept of time. She was able to keep up the count but like before, she did make mistakes and for her mistakes, he would tack on additional strokes.

  After the first twenty, she didn’t really care anymore. In general, one hurt just as bad as another. The ones that stood out though, hurt like a mother fucker. These were the ones that landed right on top of a previous strike or were ones that bulls eyed right on the tip of a nipple.

  “Would they ever again stand proud for a lover?” she bemoaned to herself between her tears.

  By the time he got to forty, she had lost all sensation in both her breasts through the agonizing misery remained. Ten more to go. She had accepted more than forty so far, so what was another ten going to matter.

  “Oooowwwwwwwww” she screamed as the forty first crack of the whip landed square on her right breast.

  Breathing heavy and barely able to speak, she croaked “Forty one” just as he cracked the whip on her left breast.

  “Oooowwwwwwwww” she screamed long and hard but still managed to count off. “Forty two.”

  “Eight … eight … more … to … go” she thought.

  ‘Crack’ sang the whip, causing her right breast to jerk in response. As her screaming continued, she almost missed the count, “Forty three”.

  “Seven … to … go.”

  ‘Crack’, “Forty four”, “Six to go.”

  ‘Crack’, “Forty five”, “Five to go.”

  She was determined to stay on track, to not miss a single count and finish what he started. She would make him see that he could not break her and she would get through this, no matter what it took.

  “Screw him to hell.”

  ‘Crack’, “Forty six”, “Four to go.”

  ‘Crack’, “Forty seven”, “Three to go.”

  ‘Crack’, “Forty eight”, “Two to go.”

  ‘Crack’, “Forty nine”, “One to
go.”

  ‘Crack’, “Fifty”, “Whew it’s over.”

  As she cried her heart out, she forget the final offering of thanks he demanded.

  ‘Crack’ ‘Crack’ ‘Crack’ ‘Crack’ sang the whip again and again across both her breasts.

  “You forgot to thank me” he scolded her.

  Reacting to the sudden unexpected attack, she just decided, “Who the fuck cares anymore.”

  She screamed and screamed, forcing the screams to go continue until her voice went hoarse. Exhausted, her screams winding down to a sob and then to a whimper.

  Somewhere along the way, she managed to utter the words he waited for. “Thank … … you … Sir … for … the … punish … punishment … I … deserved.”

  Her chest heaving from the stress of her crying and the whipping, she couldn’t get enough air. Or it was all too much, she didn’t know which. Suddenly, she felt lightheaded. A moment later, she flopped her head onto her chest and passed out.

  Chapter Fourteen

  “Oh, whipping those tits was so much fun” Jon thought. “Especially on those sweet nips of hers.”

  It took a while to reach fifty strokes. I almost made it fifty on each tit but that might have taken all day. She had been yelling ‘Fuck Me’ so much that I think it is time that I do just that. Sure, she was only saying it as an expletive but that doesn’t mean I can’t take advantage of it.

  “Hmmm, she still hasn’t thanked me yet. Should I give her a bit more time?” he asked himself. “Nah” he decided. “Since she obviously is not expecting it and has forgotten to thank me, well, this is going to be fun.”

  Pulling his arm back, he extended his reach and snapped the single tail at her twice on each of her nipples.

  ‘Crack’ ‘Crack’

  “Oooowwwwwwwww” “Oooowwwwwwwww”

  ‘Crack’ ‘Crack’

  “Oooowwwwwwwww” “Oooowwwwwwwww”

  The cunt was screaming harder than she had all during her whipping. How much more fun could he have with her. The cunts screaming was really turning him on and his cock was demanding attention.

  When she finally looked up at him, hate in her eyes, he scolded her.

  “You forgot to thank me.”

  It took a bit for her to process his statement but eventually, she responded.

  “Thank … … you … Sir … for … the … punish … punishment … I … deserved.”

  As he was about to remind her of his rules, she passed out.

  Smiling, he returned the single tail to its peg. Turning to take a moment to look back at the cunt’s carcass dangling from the ceiling hook, he left the room to get a bite to eat.

  ***

  Sitting in his study following dinner, watching her from the surveillance cameras strategically placed around the room, he returned to business. He found conducting business pleasurable but not so much as what was going on in the playroom. His diversion with this cunt was exhilarating but he still had work to do.

  With his computer monitors projecting her image on his screen, he went about calling clients and making deals. The beauty of the setup was that he would know when she returned to consciousness and so that they could resume his game.

  Hours later, his business concluded for now, he sat back in his high-back leather chair and reviewed the next scene with the cunt. She still hadn’t returned from where ever she had gone. Passed out like that, her thighs red with angry welts and her tits raw from the whipping, she almost looked like meat hanging in a slaughter house. He smiled at the thought seeing how her situation wasn’t very far from the truth. Her destiny had already be cast. By the end of the week, she would be nothing more than meat.

  When the midnight hour had long passed and she still hadn’t regained consciousness, he decided to retire for the night and continue in the morning.

  Chapter Fifteen

  When Jolene had come to, she had no idea how long she had been out. It could have been minutes or hours or even days. Taking stock of her situation, she realized that she was no longer hanging from the ceiling by her wrists. However, her hair was wet and not just from tears. She had no idea why.

  She was now bound to what appeared to be a narrow bench, perhaps some sort of sawhorse. Her screaming chest rested on a course cushion along her sternum. Her breasts hung freely on either side. Her arms were hanging straight down from her shoulders and strapped to the sides of the bench. She found this a bit of a relief as opposed to having her arms bound behind her back as had been when Jeremy forced himself on her.

  Investigating her situation further, she detected leather straps across her waist and hips, clamping her upper body firmly to the bench. Her legs were also strapped down. However, it took her awhile to figure out just why her calves, hamstrings and hips were loudly complaining. Each of her legs were stretched sideways, perpendicular to her hips. With the straps holding her hips flat to the bench, she imagined that from above, she looked like the letter ‘T’.

  Twisting her head around, which wasn’t very far at all, she could see her pointed foot poking out to her side. If she had been into yoga, her body might have accommodated the position easily. As it was, her muscles and joints screamed in the unnatural stretch they had been forced to maintain. It was as if her limp and unconscious body had been laid out and strapped down, tightly cinching the leather straps as if she were simply a package being secured for shipment.

  Looking at her leg further, she could see and feel several more straps fastening her to some sort of bar all along the length of her leg. She could see one at her ankle and another just above her calf. She couldn’t see the rest of the straps but she most definitely felt them. The straps were just above the knee, across her thigh and lastly cutting across her groin where her leg attached to her hips.

  Feeling no support or other structure beyond the ‘T’ formation, she knew and felt she was completely vulnerable to anyone and anything. Cool air drifting across her exposed pussy and ass gave testament to just how revealing her privates were.

  Twisting her head, she searched for Jon. “Where the fuck was he?” she asked herself.

  She couldn’t see him but one thing she was sure of, he was nearby. Testing her bindings, she wasn’t able to move very well. Sure enough, she was fixed tight to the bench. Wiggling her toes and fingers allowed her to at least some freedom of movement. Her breasts and thighs though were still suffering from the beating they had taken. What was worse was that her sore and extremely tender nipples felt like they were being sandpapered where they touched the coarseness of the bench. That alone made her grit her teeth.

  Lastly, she felt a collar wrapped tightly around her neck. She couldn’t see or touch it but she could feel its stiff leather pressing up against her neck. The leather wasn’t the soft smooth kind either. Rather, it was stiff with raw biting edges that cut into her skin. She could breathe ok but she had to be careful. It wasn’t attached to the bench. It just wrapped around her neck and it was awfully tight.

  “Shall we continue?” she heard him ask her.

  His unexpected question caused her to tense up.

  “Yes, Sir” she reluctantly answered him.

  ‘Wack’ was his response from a wide leather strap that spanked her exposed ass.

  For several minutes, he spanked her ass with the strap. At first, she tried hard to hold back the tears but eventually, she couldn’t hold out. As he continued spanking her ass with the stiff leather strap, her tears started to flow and a moment later, so did her crying out loud. Racked with tears, her eyes bloodshot, he continued spanking her, feeling the heat build under the relentless shellacking.

  Jolene tried hard to divert her mind from the beating but every so often, his strap would connect across both cheeks and land right on her pussy. These strokes were particularly painful. She would cry out in extreme agony at each strike.

  As much as tried not to, she was teaching him that the more he struck her there, the louder she screamed. She couldn’t help it. It just plain
hurt like hell, worse than when he spanked her on the meaty part of her ass. To her, he seemed to go on and on, relentlessly spanking her without pause.

  Sometime later, Jolene had no idea when, he finally finished. Moments later, he walked around and squatted in front of her. Between her tears and her exaggerated crying, Jolene noticed that he had changed his clothes. This told her that there must have been some passage of time occurred while she was unconscious.

  “Having a good time?” he asked her lightly, stroking her hair behind her ears.

  “Yyyyeeeeessssss … Sssiiiirrrrrr” she sputtered between sobs. “Ttthhhhaaannnnkkkk … Yyyyoooouuuuu … Sssiiirrrr.”

  “Good” he answered.

  “Now, let me tell you why you received that spanking. One, you were still due a punishment from your earlier disobedience. Second, you spent the last twelve hours sleeping it off. I got bored waiting for you. Third, while you were napping, you messed yourself. So I had to hose you down in order to clean you. Then, I had to clean the floor as well.”

  “So, while you were sleeping it off, I went ahead and pulled the next scrolls determining what punishment you would face. As you know, you pulled a spanking on your ass. What you may not realize is that you drew a count of 45. I also added 45 in payment for the extra effort I had to put in cleaning you up. That is what you just received, 90” he informed her dispassionately.

  “Sorry … Sir. Thank … you … for … my … punishment” she answered him, still sobbing from the spanking.

  “You’re learning. Very good. Still though, I owe you at least one more punishment. In time, you will receive that. First, I have something else for you. You will not forget to thank me for my gift. And as always, be sure to ask permission. Is that understood?”

  “Yessss … Sir” she croaked out between her tears.

  “Very good then. Let’s get started. Shall we?” he said matter of factly.