Chapter 46: The Mistress of Pain

Over the next few days, Nina held a number of meetings with various staff, and with the CEO. She was putting together a list of questions she needed answered, and was gathering various documents to further her research into the business processes that existed within the firm.

One rather odd, but interesting aspect, concerned what she saw in the CEO’s office. On several occasions, there was a young woman sitting in a chair at one side of the office, openly masturbating. Once she actually saw a dildo or a vibrator being used, but typically the woman was only using her fingers. She didn’t recall seeing any of the women actually having an orgasm, but since these meetings were usually fairly short, she brushed that off as being due to the short nature of her time in the office.

She assumed that these women were all employees of the firm, and not sex workers who had been brought in. She wasn’t sure if it was her place to ask about the behaviour, so she did her best to ignore the blatant display. Without exception, the women were all beautiful, were dressed as office slaves, and Nina could easily see herself being an active participant with any of them.

One morning Nina needed to ask the CEO a few questions, and went to her office to see if she might be available. Her secretary said that she had gone down the hall, possibly to the washroom. “She should be back in just a minute or two, unless somebody stops her along the way. You can wait in her office if you’d like.”

“Okay, thanks.” Nina went in and sat down, reflecting that the chair she was using was the one in which she had seen the women masturbating. She smiled to herself and spent the next few minutes reviewing the notes she had brought with her.

The door to the office swung open, and the CEO marched in briskly, stopping short when she saw Nina. A puzzled frown crossed her face as she looked at Nina.

“How long have you been sitting in that chair?”

“About five or ten minutes, Mistress. Your assistant said I could wait in your office until you were free.”

“Hmm. The last time you were here, in my office, did you see anyone sitting in that chair?”

Nina coloured a little at the memory, since it had been both erotic and a little shocking. “Yes, Mistress. There was one of your staff sitting here.”

“And what was she doing?”

“Uh ... she was masturbating, Mistress.”

“Quite right. You see, there is a protocol attached to that chair.” Her look became somewhat stern. “If you are in that chair, then your fingers or a toy must be in your pussy. And you have to stay like that until I give you permission to get up, or to come.” She moved to look down at Nina who suddenly became very afraid of what was about to happen. “Do you understand?”

“Y-yes, Mistress. B-but no one told me that I had to do that.”

“Have you not been given a copy of the company’s policies and procedures manual?”

“No, Mistress. That’s one of the things I wanted to talk to you about, since I’ll need to go over them as part of my work for you.”

“Hmm. It seems that my staff have not been fulfilling all of their duties. I’ll expect you to note that in your next report.”

“Yes, Mistress.”

“Well, that does leave me in a bit of a conundrum. Normally, not using that chair correctly is a fairly serious offence. I like to be entertained by seeing a wet pussy on display, and all the girls know that. Sometimes a girl is there because she’s being given a very mild rebuke, and sometimes they just come in because they want to relieve some stress.” She crossed her arms and thought for a moment, her eyes still on Nina, who wondered if she should start playing with herself.

“Okay, here’s how we’re going to handle this. I’m afraid you’ll have to take one for the team, and I’m going to have to pass around a few punishments to make sure that this kind of thing doesn’t happen in the future.”

“T-take one for the team, Mistress?”

“Yes. Stand up and give me your clothes.” As Nina stood and began undoing the buttons on her blouse, the Senior Mistress walked over to her desk and lifted a pair of handcuffs. She watched as Nina stripped, then showed her where to hang up her clothes. She moved behind her and said, “Hands behind your back.” Nina obeyed, although a little reluctantly, then felt the cold steel of the handcuffs close on her wrists.

The Senior Mistress moved to stand in front of her, and put out a hand to cup Nina’s pussy, massaging it a little. “I would much rather be playing with that beautiful body of yours, and if you’d had your fingers in this pussy I probably would have let you come. Unfortunately, I’ve really got no choice but to punish you even though you were unaware of the policy. If word got around that I had failed to punish someone who ignored the rules, then I’d have a much bigger problem on my hands.” She curled her middle finger and used it to separate Nina’s folds, sliding it a little way into her vagina.

The movement of the finger was making it difficult for Nina to concentrate, but she did her best to focus as the Senior Mistress spoke. “Since you’re new, and you aren’t really one of my staff, I’m prepared to lessen the punishment. This time. The next time you break the rules you had better be prepared to accept the full punishment laid out in the manual. Understood?”

The finger suddenly moved to circle her clitoris and Nina bit back the moan that was about to erupt from her throat. A little shakily she replied, “Y-yes M-mistress. I understand.”

“Good. Now, instead of the fun we could have had, you are to go down the hall to Room 22 and present yourself to the Mistress there. You are to tell her that I said to give you a level two punishment. Have you got that?”

Nina was climbing desperately close to an orgasm by this point, but was sure that her punishment would be increased if she came. “Yes, Mistress. Room 22, level two punishment, Mistress.”

The Senior Mistress abruptly pulled her hand away and said, “Good. Now get going. Report back to me when you’re done and we’ll see what happens next.”

“Yes, Mistress. Thank you, Mistress.” She quickly left the office and walked past the receptionist’s desk. Behind her she could hear the receptionist being called into the Senior Mistress’s office, and wondered if another punishment was about to be handed out.

Her walk down the hall seemed to take forever and was extremely humiliating. Everyone she saw looked at her nudity with a smile or a smirk, and a few even gave one of her breasts a quick caress or patted her on her naked behind. Since it was obvious that her hands were cuffed, she also heard a couple of comments about how red her ass would be when she walked back.

When she finally arrived at Room 22, she found it closed by a heavy wooden door. A sign on the door said, ‘Enter at your own risk’. With her hands cuffed, she had to turn around to grab the doorknob. She was able to twist it and felt the door begin to open, so she moved backward as it swung out of the way. When she was all the way in, she let go of the doorknob and felt the door swing closed, obviously with some sort of automatic closer.

She suddenly felt a hand caress her rear and flinched in reaction. She quickly turned around and came face-to-face with a tall, stunning brunette wearing a leather vest and a very short leather skirt. The vest wasn’t fastened so the inner curves of the woman’s breasts were on display, and her skirt was slit along one thigh to expose the leg all the way to the woman’s hips. She was wearing high leather boots and the overall look made Nina want to drop to her knees as she had done the first time that she had seen Gretchen dressed like that.

She bent her head and said, “Mistress. Hello. My name is Nina. The Senior Mistress sent me to you.”

“Hmm, very nice. But why are you here?”

“I ... I’m supposed to be punished.”

“I expected that. I’m the one who gives out punishments.” The woman circled Nina, noting her handcuffs, her physical attributes and especially her tattoo. When she was once again standing in front of her, she cupped her hands under Nina’s breasts and squeezed them very firmly. “Very nice tits. I imagine you’re quite proud of these.” After a moment she stepped back and released Nina’s breasts, watching them as they settled back into place. She locked eyes with Nina and asked, “Well, were you given any instructions?”

A slight tinge of fear crept across Nina’s face as she replied, “The senior Mistress said I should tell you that I need a level two punishment.” She swallowed hard, then added, “I’m not sure what that entails.”

“Hmm. A level two. Since you’re a slave, I assume you’ve been spanked?”

“Yes.”

“That should be ‘Yes, Mistress’ unless you want to up it to a level three. I am the Mistress of Punishment, although many of the girls simply call me ‘Mistress Pain’.” She ended her comment with a wink and a smirk.

“I’m sorry, Mistress. I’m not too sure of the protocols here. To answer your question, yes, I have been spanked, Mistress.”

“Well, to get back to the original issue—a spanking is a level one punishment. And I’m sure you’ll learn the protocols pretty quickly, or you and I will be seeing a lot of each other.” She trailed a hand over Nina’s belly. “Not that I’ll mind, I’m sure.”

“Yes, Mistress.” With her face showing some concern, she asked, “Please Mistress, if I may—does a level two punishment involve a whip?”

“No, it doesn’t, but why do you ask?”

“My owner, Mistress Gretchen, has vowed to me that no one except her shall ever whip me. She doesn’t trust anyone else to use a whip on me.”

“So, if the punishment were to require a whip?”

“Then I would have to respectfully ask that my Mistress be consulted before the punishment were administered.”

The Punishment Mistress laughed upon hearing Nina’s request. “I think that’s the first time anyone ever asked for someone else to be consulted in regard to a punishment.” She reached out to rub a hand over Nina’s tattoo. “Of course, I think it’s also the first time that someone else’s slave has ever been in my lair. You see, all of the girls who work here are slaves to the Senior Mistress, myself included, although I outrank most of them. You’re kind of a special case.” Her hand moved to cup Nina’s vulva, giving it a firm squeeze. “Very special, indeed.”

As she felt the hand cup her pussy, Nina was reminded of the fact that she was naked, handcuffed and under the control of someone who meted out punishment as her primary role. Another twinge of fear went through her as the hand on her pussy moved away and the Mistress said, “Well, enough delay. We need to get this punishment over and done with so you can get back to work, or else I’m the one that will be getting punished.” She glanced up to meet Nina’s gaze and said, “And the Senior Mistress will use a whip, and she makes sure that it hurts.”

The Mistress took Nina buy the arm and led her over toward one wall. About five feet out from the wall was a pair of metal stanchions set into the floor. Joining them was a horizontal bar made of what looked like steel, although it was thickly padded and covered with what appeared to be leather. The mistress positioned Nina with her hips right against the bar, then adjusted its height. Nina noted that there were cuffs set into the floor several inches away from each of her feet. She could see that there was also a pair of chains and cuffs reaching from the wall in front of her to the padded bar.

The Pain Mistress unlocked Nina’s handcuffs and tossed them onto a bench to one side. As Nina brought her hands in front of her, the Mistress picked up one of the cuffs from the bar and quickly fastened it around Nina’s right wrist. She moved to Nina’s other side and did the same thing with her left wrist. She then knelt and said, “Spread your feet.” As Nina complied, she felt each of her ankles being wrapped in one of the cuffs on the floor. “There we go. Now we’re almost ready.”

She stood and told Nina to bend over the bar, then moved to a crank at one side of the wall. As she turned the handle, the chains tightened, stretching Nina’s arms in front of her. She soon ended up being bent at the hips with her back and arms horizontal, her legs spread open, and completely helpless to prevent anything being done to her.

When she was satisfied with Nina’s position, the Mistress moved to stand by her rear. From this position, she could easily see the butt plug in Nina’s rear. “Ah, I see you’re one of the Mistress’ special people. That’s a surprise, because they so seldom get punished.” She grasped the end of the plug and slowly pulled it out of Nina’s rear, then took it over to a sink in one corner and dropped it into some hot water.

When she returned, she leaned over Nina and reached under her to grasp each of her breasts in a tight hold. “I really do like these tits.” She was pulling on each of Nina’s nipples as she continued speaking. “I didn’t tell you that in addition to punishing the girls, I am also allowed a little leeway, so I can add a few minor things to the process if I think it would help.” By now Nina’s nipples were fully engorged and quite stiff, allowing the Mistress to have something more on which to focus her attention. “In your case, I think we should include these marvelous tits.”

She stepped over to a cabinet and picked out a couple of things, then returned to Nina’s side. She took Nina’s left nipple in her fingers again, rolling it and pulling it until she was satisfied. Then she opened the jaws of one of the clamps she was holding, and let it quickly close around the rampant bud. The sudden pain in her nipple made Nina cry out, as this was one of the most painful clamps she had ever felt. The clamp was toothed, although the points of the teeth had been filed down to ensure they wouldn’t pierce the skin. However, the clamp also had a weight attached on a short chain, and when the Mistress let the weight go, the added tension made Nina cry out again.

Her other nipple followed, making Nina cry out once more. She was taking deep breaths, trying to work through the pain in her nipples, knowing that asking to have the clamps removed was a waste of time. If anything, she was certain that if she complained the Mistress would find something even worse. The true sum of her predicament came to her when the Mistress moved behind her and once again bent over her. The Mistress slid her hands along Nina’s belly, coming toward her breasts which she then grasped and squeezed, making the weights bounce and sway, and bringing sharp flares of pain to each of Nina’s nipples.

“Now, my dear, you’re ready for me to punish. You’re probably going to want to try not to flinch or move around too much, ‘cause that will set those weights flying around.” She shook Nina’s breasts to illustrate, making the weights sway and pull on the clamps. “And as you can tell, that will make your poor little nips hurt like hell.” She shook the captive breasts again. “And if it doesn’t, I can always tighten up the clamps and add more weight.”

Her laugh sounded very cruel as she released the tortured breasts and moved back to the cabinet. This time she returned holding a leather strap about eighteen inches long. The strap wasn’t smooth along its length, as it had been sanded to roughen its surface and increase the friction with the skin of its victim. She moved to one side of Nina, and tightened her grip on the handle of the strap, adjusting her position in preparation for the first blow.

“Just so you’ll know, a level two punishment means that I use a strap, not my bare hand or a glove, and you get ten to that gorgeous rear. It’ll be nice and red when I’m done, and I don’t imagine you’ll want to sit down for a while.” Her arm drew back and the first blow landed the instant she had finished speaking. The strap crossed both of Nina’s buttocks exactly in the centre and a swath of red appeared almost immediately. Nina yelled and shook in her restraints and the weights on her nipple clamps flew in every direction, making her feel pain from two different places.

The Pain Mistress waited for a moment to see if Nina would say anything. When all she heard was deep breathing as Nina tried to master the pain, she said, “I would have thought that you had been taught the proper protocol about punishment.”

It took Nina a moment to realize what the Mistress meant as she struggled to think through the fog of pain. It suddenly dawned on her and she blurted out, “One Mistress! That was one. May I please have the next?”

“About time. I shouldn’t have had to prompt you. That’s going to cost you. We’ll start over and see if you can get it right this time.”

Nina groaned inwardly, knowing that her mistake would cost her at least another one of those burning stripes. The pain from the first stripe was only just beginning to subside, but the next one took her breath away as it landed in exactly the same spot. She clenched her jaws to hold back the scream that wanted to erupt, and sucked in a huge lungful of air before she forced out the words. “That was one, Mistress. May I please have the next?”

“Well done, and very polite. Many of the girls here would be cursing me as they counted. Of course, the stupid ones don’t realize the price for that.” She swung the strap to catch the lower part of Nina’s ass, leaving a new bright red stripe on the pneumatic flesh and hearing Nina cry once more in reaction to the pain.

It took surprisingly little time for Nina to count out the stroke, so the Mistress gave her the next one just as quickly. She could hear Nina gasp in reaction, but also heard the response with the count right after the gasp. She knew how much this kind of strapping hurt, but she also knew that ten strokes would not leave any lasting damage.

As part of her own slave training the Punishment Mistress had been spanked, strapped, and whipped many times. While some of that punishment had been earned as a result of her attitude, much of it had only come when she had agreed to be trained as a punishment slave. It had been drilled into her that before she could be allowed to mete out punishment, she had to know what it felt like so she could judge her own work, and master control of the various implements of pain.

Her fourth stroke of the strap caused the first signs of real distress in Nina as her cry was followed by tears and a little sob escaped her mouth as she called out the count. The fifth stroke landed on top of the first, and this time Nina shook from side to side, alternately trying to lift her feet to absorb the pain although this move was thwarted by the cuffs on her ankles.

Her shaking caused her some other pain as it set the weights on her nipple clamps flying. The sharp pains in her nipples refocused her mind away from her rear, and nearly made her forget to count the stroke. She almost shouted. “F-five, Mistress. That was five. May I have the next?”

“No need to shout my dear. I can hear you quite well, and this room is soundproofed so we won’t bother the neighbours, regardless of how loud you get.” The Mistress stepped up to Nina and rubbed a hand over the wide welts on her ass. She moved her hand into the cleft between Nina’s buttocks, lightly grazing her anal ring, and then sliding her fingers into Nina’s folds. She smirked when she felt the signs of wetness there; most of the women she strapped this way would be completely dry, all thoughts of sex driven from their minds by the pain. The damp pussy was even starting to flower slightly; the Mistress wondered for a second how it would react to being strapped.

“So, little one, how are you doing? We’re halfway through it. Only five more to go.” As she spoke her fingers were sliding back and forth through Nina’s folds, feeling the slickness there, but not trying to enter her vagina and avoiding her clitoris. If Nina were to enter a higher level of arousal, she wanted to make sure that it was brought on by the pain of the strapping, and not by her fingers.

She was taken completely by surprise when Nina said, “Please continue, Mistress. Please give me the last five strokes.”

She stepped back into position. “Very well, then, since you are so ready to receive them...” She started to deliver the next stroke with a vicious swing, but pulled up at the last instant as her training instinctively cut in. She knew to never hit someone while she was emotionally reacting to some event or anything said to her, or else she could do real harm to the person under her control.

She did, however, deliver a second stroke almost on top of the previous one, forcing a short scream out of Nina as the blaze of pain lasted for a much longer interval. “S-six a-and s-seven, M-Mistress. Those were the sixth and seventh. May I please have another?”

The Mistress delivered the next two strokes almost together, but each one was aimed at the top of Nina’s thighs, just before the crease at the bottom of her ass. One stroke landed on her left thigh, and one on her right. The Mistress knew that these would hurt immensely, and Nina’s reaction confirmed her thinking. She screamed after each stroke, her breath forced from her lungs by the flames that erupted on her legs, her whole body shaking as it tried to absorb the pain.

She loudly sobbed her next breaths in and out, the weights on her nipples swinging wildly, all of her attention focused on the feeling that her thighs had been blistered. Moments went by before she remembered that if she didn’t count then the punishment would start all over again. Through her cries she choked out, “Eight and n-nine, M-Mistress.” She took another deep breath, pulling on her wrist cuffs for strength, and softly added, “May I p-please have the last one?”

“You certainly can, but I don’t know how much you’ll like it.”

Nina had a sudden vision of the next stroke being delivered on top of the last two and she quickly blurted, “Please, Mistress, please not on my legs again.”

“Oh, I wouldn’t dream of that. Believe me, I know how much it hurts on those tender thighs. No, no, this next one will be going into an even more special place.” As she spoke the Mistress moved to stand directly behind Nina. She could see the wetness on Nina’s pussy, and see that it was flowering quite a bit, so she knew that Nina’s body was reacting to the pain, regardless of how bad it felt. She lowered her arm and then swung the strap straight up, right between Nina’s legs, covering all of her labia and wrapping up onto her mound. Part of the strap even rubbed against the tip of her clitoris mashing the little bud and scraping over its tender tip.

Nina’s reaction amazed the Pain Mistress. For a second she didn’t even move or speak, and then the pain overwhelmed her. She instinctively tried to close her legs to protect her pussy but, trussed as she was, there was nothing she could do. A raw, primal scream finally forced its way out of her throat, but the nerves in her pussy were sending conflicting signals, both making her think she was in agony but also near to an orgasm.