Nancy and Her Boss Ch. 03

"That is better," he said. "But just so you aren't tempted to be so stubborn any more tonight I think you need to wear these." With that he took the two chains that hung from her collar, the ones with the nipple clamps and put the clamps on her nipples. "Maybe these should be a little tighter than before," he said as he adjusted the tension on them.

"Ahhhhhh, oh, oh no, please Master, they are too tight," she cried out in pain.

"You let me be the judge of that young lady. Just remember they are that tight because you had to be so uncooperative. Now how about we practice. Move to your normal position."

Nancy released his hand and moved to a kneeling position, fully upright. He moved behind her and looked, then with the cane he tapped her sore behind and said, "thrust your pelvis out more." He moved around front and used the cane to tap on her nipple clamps saying, "take a breath so your tits are out more." She winced in pain as the cane played with the clamps.

"Very good, now show me the relaxed position" he said.

Nancy was already tense from having been in the normal position trying to thrust her pelvis and chest out so she quickly sat on her heals. She jumped up a little as the pain from her buttocks rocked her body. Her butt was very sore so she lowered herself to almost sitting on her heals, this was agonizing to hold but she couldn't put any weight on her butt.

He didn't fail to notice this difficulty she was having and smiled. He paused for a while letting her strain trying not to put any weight on her butt. Finally he announced, "Ok, now come back to the display position."

With a great deal of difficulty Nancy was able to stand without causing her butt to sustain any weight. She came to an upright standing position, feet eighteen inches apart, hands laced behind her head and elbows at a 45-degree angle. Her pelvis was out and she took a deep breath so her chest was out. Her nipples were already clamped in the erect position.

In a slightly sadistic mood he played with her nipples to see how much discomfort he could inflict. Then he turned on her clit vibrator and inserted two fingers in her cunt. He heard moans from her but she stood still as his fingers gathered up plenty of moisture from her twat. Finally he turned off the vibrator and put the two fingers to his nose. He smelled them once and then twice before he moved them to her mouth to be cleaned. Again her mouth was as good as a vacuum cleaner and there was a loud popping noise as he withdrew the fingers.

"Very good. I am impressed," he said. He could see the smile break out on her face but when his eyes met hers she stopped smiling, afraid that it wasn't allowed on display. "Sissy, show her punishment position," he commanded. Sissy immediately moved to his side and bent at the waist with her hands hanging from her shoulders. "This is the position a slave takes when about to be given a mild punishment for a minor transgression. Now take careful note on this position as you will no doubt be assuming it frequently this weekend." She could see his smile as he said this but she had no doubt that he was correct about it.

"Next we will move to the discipline position. This is the position a slave takes when she is about to be disciplined and won't be allowed to move any during the discipline. Sissy assume the discipline position please."

Sissy move a little to the side of her master and again bent at the waist but this time she grasped her ankles as if holding on for dear life.

"Nancy I want you to observe closely that Sissy will not move no matter what happens." With that he turned a little and let loose with the cane cracking Sissy across the middle of the buttocks. Sissy stayed in position neither moving nor making a sound and Nancy knew how painful that must have been. Again he drew back the cane and let loose with a swat that crossed both thighs at the joint between the thighs and buttocks. The cane made a loud noise as it hit but Nancy could only detect the slightest of movement in Sissy and not a sound came from her mouth.

"Thank you Sissy, you may put this cane back now." He handed her the cane as she stood. Nancy watched as Sissy took the cane and put it back, she rubbed her butt as she was returning to assume her normal position.

"Did you notice that Sissy hardly moved when I delivered those blows with the cane?" he asked Nancy.

"Yes Master," she replied still standing in her display position.

"Good, because I expect you to follow her example when in that position," he announced. "Now let's move on to a more pleasant part of your training. Orgasm control."

"Sissy, please bring me the thin rosewood paddle from the shelf," he said as he turned to Nancy and told her, "come with me."

A panicked look came over Nancy's face as he led her to the spanking horse. She pulled back as he got close but his arm grasped hers and pulled her towards it. "But Master my butt is still so sore from the caning you gave me. Please can we postpone this until tomorrow?"

"I'm afraid not my dear, remember I said you were going to be punished for all those climaxes you had without permission, not to mention the dropping of the Ben Wah balls. Then we will be moving on to climax control after the spanking."

Nancy started to cry, "but Master you know how horny I get when you spank me, how do you expect me to concentrate on climax control when my body will be craving cock?"

"Oh yes, I forgot you became a cock slut when you get spanked. And as I remember it you climax every time a cock is forced into your butt hole too. I guess the whore in you comes to the surface when you are whipped," he said with a smile. "I guess we will have to teach you to overcome that urge then. It will seem a little strange punishing you with a whipping which makes you a cock slut and trying to convince you that if you cum you will be whipped until you are horny enough to cum at the drop of a hat. That does seem to be a dilemma. How about this, I'll wait to spank you until we go to bed and then I will fuck you right after spanking you. You may be able to sleep after that although I suspect it will be on your tummy. Is that good for you Nancy?" he sarcastically questioned.

She thought he was being serious but after thinking about it she said, "No, I'll take my spanking now so I have some recovery time before bed." He had her standing at the spanking horse so she couldn't see his smirk at her answer.

"Sissy, bring the ankle cuffs too" he said but he turned to see Sissy standing there with the paddle and ankle cuffs already. "Good girl," he commented. His hand went to Nancy's shoulder and pressed her forward indicating she should bend over the spanking horse. She bent at the waist and leaned over the horse until her hands could touch the floor. She was on her tiptoes and her abdomen was lying on the padded horse. Her wrist cuffs were locked to the legs of the horse, and then her legs were spread wide so her ankles could be cuffed to the other legs of the horse.

"Now Nancy, this is going to hurt but it should serve as a reminder to you that you cannot climax without permission. It should help you in a few minutes when you are about to climax and you know you either stop the climax or get spanked again. Sissy will give you some guidance on how to hold off your climax. The question now is how many swats with the paddle should I give you for all those times when you climaxed without permission. Have you got an answer Nancy?" he asked.

"No sir," she admitted.

Then he turned to Sissy and asked, "how many should she get?"

Sissy thought and said, "I'm not sure Master. You give me twenty with the cane if I do but the paddle isn't as bad as the cane so it should be more than twenty. But since she has not been trained to prevent a climax it shouldn't be that many until after she is trained. Maybe five for each unauthorized climax." Nancy heard all this and began to realize that Sissy was being generous to her in her decision of five. Of course Nancy quickly thought of all the times she climaxed and tried to multiply by five and realized how sore and horny she would be by the end of it. In fact she might even climax during the spanking as she had seen Sissy do earlier this evening.

"Five it is then," he announced. "How many is that all together Nancy?" he asked.

"Oh Master, I am not sure, maybe a hundred. But I am not sure if I can take that many without climaxing while you spank. You know how horny I get being spanked." Nancy was almost in tears just thinking of one hundred swats with the paddle.

"Tell you what, we'll go slow. In fact we will go slow enough that after each swat you can count and tell me thank you and ask for another swat. How is that?" he smirked.

"That is terrible. What happens when I start crying and can't speak?" she responded.

"We can take small breaks. Now let's begin. Each swat you count then say 'thank you master I deserved that, please give me another to make me a better slave.' Do you understand?" he instructed her.

Before giving her a chance to answer he delivered the first swat to the upper portion of her right butt cheek.

"Owww, damn. One, thank you master I deserved that, please give me another to make me be a better slave." Her body jerked as she fought the restraints but was unable to move.

The second swat landed on the bottom of her right cheek just above the crease that joined the butt to the thigh.

"Owww, Ouch, that hurt. Two, thank you master I deserved that, please give me another to make me be a better slave."

And so it went, his swats moving around on her butt from cheek to cheek, from top to bottom. Around the tenth swat he realized she wasn't really hurting enough so he started a swat to her upper thigh. This hurt intensely and she started to cry after a few of these. As he moved the swats around it was about every fifth swat that landed on her thigh. About the 4th time her thigh got hit she was bawling terribly and could hardly speak. They took a break for her to recover a little but soon resumed. When she got to ninety he started to deliver swats only to her thighs. As he hit her thigh she would cry out terribly in pain, then count and thank him but she was constantly trying to move her legs to avoid the painful swat to follow. At 100 he released her from the restraints and she rose to a standing position but she couldn't stand without help. He turned her towards him and held her against his body as she recovered.

As she stopped crying she whispered into his ear, "you enjoyed my punishment too much. And Sissy probably enjoyed it too much. Can you imagine how horny I am? Just a touch to my cunt and I will go off without permission again. Are you going to spank me again for that?"

He noted that this time she didn't refer to Sissy in some derogatory descriptor so he calmly said, "yes you get spanked every time you cum without permission but Sissy and I are here to train you to hold off your climax. But I know your horny now so you are allowed to have one climax during your training without punishment. I advise you to hold off as long as you can before using your freebie. Now can you stand on your own so we can begin training."

He looked at Sissy and said, "bring the sling over to the middle of the room."

As Sissy walked to the edge of the room he watched Nancy's reaction. He could tell she was nervous so he placed his hand on her punished butt cheek, giving a little squeeze, as he whispered in her ear, "my little slut must be very horny to begin her training."

"Oh yes master I am very horny and so afraid that you will make me cum without permission. Master, please, I don't want to disappoint you and cum without permission but I am afraid I won't be able to help it" she leaned back into his body as his hand continued to caress her bottom.

"Sissy will be here to help you. She is an expert in avoiding climax so she will help you as much as she can. Listen to her and try to do what she tells you" he said into her ear. The warm breathe from his mouth causing her to quiver and develop goose bumps on her entire body.

Sissy brought the sling over to where they were standing. Nancy eyed it and saw it was shaped like and X with supports at each end as well as one on either side of the center. Sissy guided Nancy to the sling and had her lay on her back, spreading her arms and legs in an X shape. Her hands were strapped at the wrist, her legs strapped at the ankle. She now lay on the sling in a very exposed and vulnerable way. Her cunt was exposed; legs wide apart and her labia lips were wide open, partially because she was so horny. The nipple clips were still pinching her nipples and there was little blood in them now. He reached over and removed the clips, her nipples started to puff up as blood shot into them. There was a lot of pain with it but Nancy could feel the pain turning to pleasure as it shot down to excite her cunt.

"Oh Master, it hurts but my cunt is getting so hot. I am going to cum, is it ok if I cum now Master, please let me cum."

Sissy moved to her ear and said "Mistress, you must concentrate on something so you can ignore the feeling. Think about all the boring things you do at work, how you hate it sometimes."

This seemed to help Nancy until he turned on the clit vibrator. Her pelvis shot up the moment the vibrator came to life and she said, "Oh no. Oh, oh, I know I am going to cum any second now."

Again Sissy whispered in her ear, "concentrate on something but the feeling in your body. Think of your last auto accident and how upset you were, how mad you were."

The vibrator stopped and Nancy let out a groan of relief saying, "thank goodness."

Sissy watched as he reached over to tweak her aching nipples. It was like an electric shock ran from nipple to clit. Her body jolted as her pelvis again moved up in response to the feeling in her clit. Sissy continued to whisper in her ear and give her ideas on how to avoid the climax but her pelvis kept moving up and down as if she were humping some invisible object. Finally it was too much for her and she let out a moan as she climaxed. "Ahhhh, Master I am cuming, I am so sorry Master. Ahhhh, cummmming, ahhh."

He watch her orgasm with a smile on his face. Sissy bent by her ear and could say nothing that could help. Nancy noticed Sissy had a look of pure dismay, perhaps a look of sorrow for her unauthorized climax. Nancy thought she saw a tear of sorrow in Sissy's eye.

He said, "ok, I guess we will have to try again. Nancy, pay attention to Sissy she can avoid an orgasm for hours so learn from her."

Nancy puffed up and boldly said, "easy for you to say. I am the one being teased not her. How can anyone not climax when they are teased that much?"

"Ok Nancy, if you think that let me do the same to Sissy that I do to you and see how long she can last. How is that?" he asked.

Nancy wasn't too sure about that but she reasoned that at least if Sissy had the same done to her it would be a fair comparison on how well Sissy could resist an orgasm. She finally said, "that sounds fair to me." Her body was now calmed down from her climax and she thought she could resist another using Sissy's hints.

"Sissy, go get your nipple clips," he said. Sissy headed off to get then and quickly returned. He connected the chain to her collar and then put the clips on her erect nipples.

Nancy heard Sissy groan and a gasp as she sucked in air as the clamps pinched her nipples. Nancy thought it wasn't fair because she hadn't had her nipples pinched for an hour before being released but said nothing. He came over to Nancy and put her clamps back on her nipples. Nancy groaned and gasped as she tried to squirm on her sling but she was too restrained to move.

Next he took a vibrator and inserted it into Sissy's cunt. As it went in slowly Sissy whispered in Nancy's ear, "remember to concentrate .. ahhh .. on .. ahhh .. something else."

Then Nancy felt the vibrator slip into her cunt. Her pelvis moved up to thrust against the invading object. She gasped but began thinking about anything that would help her lose thoughts of how good it felt with her stuffed twat. As he turned the end of the vibrator up to its highest setting she saw him reach over to turn Sissy's vibrator up to full. She lay there noticing the erotic feelings moving up her body and she knew she needed to concentrate on something to keep the orgasm away.

"Concentrate on work, think about having to stand at the copier for hours making some copies for one of those dull meetings," Sissy whispered in her ear. "Think how boring it can be."

Nancy couldn't believe how this worked. Why was Sissy helping her like this? Was Sissy going to get punished too, if she failed to help her resist climaxing? Did Sissy really want to help her? Nancy thought back to the tears of sorrow in Sissy's eye when she had an orgasm without permission.

They worked at this for what seemed like several hours but in reality was only about 2 hours. Each time he would do something to drive Nancy close to climax Sissy would whisper something in her ear to give her the strength to avoid climax. True to his word everything he did to Nancy he did to Sissy and they both avoided climax until the end of Nancy's training session for the night.

As Nancy was released from her restraints she could hear the hum of more than one vibrator. As Sissy helped Nancy up from the sling she could hear the clit vibrator going strong but she heard something else. Nancy soon realized that the nipple clamps on Sissy had vibrators on them and they were buzzing quite loudly. As both girls stood before their Master he reached over and pulled the dildo from Nancy's swollen cunt and then from Sissy. As he removed it from Sissy he slowly and deliberately moved it across her clit vibrator sending Sissy into a groaning and verbal climax.

"Oh gawd, ahhhh, oh Master I am so sorry, AHHH I am cummming," Sissy yelled out.

"That will cost you Sissy. That will cost you dearly," he told her.

"Yes Master, I understand and will accept whatever you choose to do to me. I am so sorry. I just wasn't prepared for that last tap on my clit vibrator and lost my control."

"Yes. That is going to cost you a night in the barn tomorrow night. I think maybe I will let Nancy join you," he commented.

"Nooooo, please Master. Nooooo, not that. Please Master, I beg of you. I'll do anything but please not that."

Nancy was taking this all in and began to wonder what would happen to her in the barn and why was Sissy so afraid of it.

"Sissy you know better than to beg like that, you'll do anything I say anyway. Now since you don't want to spend the night in the barn suppose I just put you over the spanking horse and whip you for a while. I warn you though, if you cum while I am spanking you'll be spending the night in the barn anyway. Are we clear Sissy?"

Her head bowed, she replied, "yes Master." Nancy could see tears streaming down her cheeks and guessed Sissy was afraid she would cum from the spanking just as she did earlier in the evening.

"Sissy go over to the wall and bring me the large cane – the one you hate so much – and the pussy whip."

By now Sissy's head was hung low and her shoulders were even bent forward as if she had already lost the challenge to not cum during her whipping. Never saying a word she got the cane and pussy whip, handed them to her Master and walked to the spanking horse in a totally defeated manner. She lay across the horse, attached her ankles and left wrist to the latches and awaited the remaining latch to be connected for her.