Training Rebecca Ch. 05

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She learns new depths of submission & is pierced.
11.4k words
4.65
158.7k
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Part 5 of the 11 part series

Updated 10/19/2022
Created 06/23/2005
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Part V (Wednesday)

Monday morning was nothing but usual, that is, it was as usual as Rebecca's life had become. She had slept well, very well, the night before, and visions of the events of the evening flooded in. She pushed them aside and got on with the day. She did her morning exercises with the penis gag, and dressed as she had been taught. Maria was wearing a cover-up and told her she would be spending her day-off at the beach with friends after delivering the boys to school. Rebecca nodded, spent a few minutes with the boys, and then headed for the office. There, she sat as required, skirt up in back so she was sitting on her bare ass (she was wearing her skirts fuller these days since a tight skirt was difficult to hike up), with her legs parted, even under her desk. She expected a phone call from Kyle in the morning, but nothing happened. When she saw any of the men who had been at the strip club, she reddened and had to take a deep breath before speaking. But they acted as though nothing was out of the ordinary, so she began to relax. The afternoon, likewise there was no contact from HIM. Finally about the time she was getting ready to leave HE walked into her office.

"Hello, Sir," she said looking up, trying to smile.

"Hello, Rebecca. How is the corporate world these days?"

"Fine, thank you, Sir."

"You are sitting as I have instructed?"

"Yes, Sir. Do you want to check?"

"Of course," he stepped over and pulled up the back of her skirt as she sat until he could see her naked ass through the open back of the chair. "You have recovered from last night?"

She blushed again thinking about all the men, most of whom she knew, who had their hands on every part of her body. "I slept well, Sir," was as much as she could manage.

"I shouldn't wonder. I have a few instructions for you."

"More rules to complicate my life?" she said trying to keep the venom from her voice, but forcing a smile.

"Wednesday morning you have your appointment to get your piercings," he said ignoring her. "It is scheduled for 10:00 so you will have to make arrangements to come in late to work. Here is the address. They will be expecting you."

"Yes, Sir," she said wondering to herself what he would do if she skipped the appointment. She shuttered and decided that she really didn't want to know.

"The other matter concerns your pc muscles."

"My what?" she inquired.

"The muscles that control your vagina. They are a bit weak, as both Joanna and I noticed. I will expect nice strong muscles to milk my cock if I should decide I want to fuck your cunt. You will strengthen them for me over the next few weeks." He went into the kitchenette and returned. "Remove your skirt and spread your cunt lips." His examinations of her nether regions always left her blushing and confused. He held up a glass "Now you will pee into this glass," he said as though instructing someone on a point of golf.

"Oh my God, your aren't..." she said in a loud voice. Then looking toward the door she hissed, "you can't really mean it."

He said nothing, just looked at her waiting patiently for the realization to sink in. It was his eyes that were different than any other man's. They seemed to look right inside her, and seemed to know just what she was thinking. They caught hers and told her that her objections would come to naught.

"I will try, Sir," she said blushing as she pushed her bald labia against the glass. Nothing happened. The minutes ticked by.

"Rebecca," he said sternly.

"I am trying, Sir, really I am. But this is soooo embarrassing. I have never done this in front of anyone." She paused. "I know I can do this for you." She was pushing, but nothing was happening. She knew he would be angry with her if she failed him. It was just so...so, she didn't know what. He had taken something very personal and private and was taking control of even that.

She looked down at his expectant face. "I won't disappoint you, Sir," she said with resolve. And soon, as good as her word, the sound of piss hitting the glass could be heard.

"Stop," he said firmly and louder than usual. She sucked in the muscles responsible for pee control and in a couple of seconds only a few droplets of water trickled down to fall into the glass.

"You took too long to stop. It is a sign of weakness in your muscles. Start up again." She relaxed and felt the pee streaming out.

"Stop," he said as soon as he heard the spisssss of her flow. This time she was ready and pulled in the muscles hard.

"That was a bit better. Go." And on she went starting and stopping until she was drained.

"From now on, whenever you pee, you will start and stop five times. That will exercise the muscles we have been speaking about, and you will begin to isolate them. I will have more serious exercises for you to start in a few days. Do you have any questions?"

"I don't think so, Sir."

"And Rebecca..."

"Yes, Sir?"

"I know these exercises will make your little cunt horny. But you don't have permission to cum."

"It will not be a problem, Sir," she answered a little too hastily.

"See that is isn't."

After he left, she made the arrangements with her secretary to move a couple of appointments on Wednesday morning.

Tuesday morning, she awoke and started and stopped five times as her new instructions dictated. Then she went down to exercise and found another box like the one the previous week. Inside was a slightly longer and wider pecker gag. She took it out and it took 10 minutes before she could get it in without gagging on it. Then she cautiously did her exercises with it strapped to her head, the end jutting into her throat slightly and causing her to breath more heavily than usual. Her throat was dry and scratchy when she finished and was able to take the offending article out. The water from her water bottle felt good and she sighed thinking how complicated her once simple life had become.

The day went smoothly. By the end of it, she was feeling the kegels she did every time she took a piss. She went upstairs and sat on the edge of the bed. He had extended his control into almost every aspect of her life, and she resented it with every fiber in her being. She could have just given her body to him without much in the way of regret. But the constant tingling in her clit reminded her that he had wormed his way into her mind and she shuttered as she realized she was losing control of herself. She wondered if it was possible to have the kind of orgasms he gave her, no, forced upon her, in any other way. Was it that she was encountering new sexual experiences like a teenage girl, or was it something else, something totally different, something he understood about her that she didn't understand about herself? She constantly marveled at his command of himself and everyone around him, even as she wished his command over her wasn't so powerful and complete. She knew he wasn't the sort of man who would look kindly at a woman whining about him wanting sex too often, or complaining about the way he dressed, or the hours he kept.

She did know that she felt stimulated and her mind was drawn to him every time she did something he had commanded her to do. And the fact that he had expressly forbidden her masturbation privileges, something she never thought about normally, made her think of it all the more. She undressed, and naked lay on the bed. She ran her hands over her breasts and found the nipples ultra sensitive. She debated whether or not she should chance it, and turned red at the thought that he might know and call her again, interrupting a perfectly good finger fuck. She moaned as she rolled her nipples between thumb and forefinger. She was so close to an orgasm and hadn't even touched her clit. Reluctantly, she dragged her hands away, turned out the light, rolled over, and tried to sleep.

Wednesday promised to be another beautiful day. As the sun shone through the bedroom windows, Rebecca roused from a restless night and remembered that she was to be pierced that morning. She peed five times, counting starts and stops, put her hair in a ponytail, donned sweats and went downstairs to call John. After the third attempt, she gave up and did her exercises after finally getting the new penis gag in place. There was no rush this morning since she was going to have her piercings done at 10:00 and wasn't due into the office 'til after lunch. She spent time with the boys, gave them both hugs, and Maria loaded them in the car for school. Then she relaxed on the couch with a second cup of coffee and read the paper.

It was some time later that a deep male voice startled her from her concentration. "Good morning, Rebecca."

The paper slipped from her grasp. Right behind him was Maria who said, "I'm sorry, he just burst past me when I opened the door. Do you want me to call the police?"

"It is fine, Maria," she said as he sat in a chair opposite her.

"Sit down, Maria," he indicated another couch on a third wall. She looked at her employer who nodded her ascent.

Maria crossed in front of him and sat down. He studied her. She was in her mid-twenties with dark features and a nice figure accentuated by the dress she wore. Her lips were full and sensual, the heritage of Spanish Peninsulares many centuries ago. They had also given her finely chiseled features, and a desire to display a nicely tanned cleavage.

"Rebecca, assume position #1," he said without taking his gaze off the maid.

She glared at him shaking her head. "You have gone too far. This is my home. You will have to leave now," she said enunciating each word with fire in her eyes. She made to rise, but his eyes held hers and she sank back into the couch.

"Maria, leave us," he ordered.

"Do you want me to call the police?" she asked her employer.

"Yes," he smiled, "that would be just the thing to do."

Rebecca shook her head; "No, not the police. Just do as he says," she was shaking as Maria left the room.

Kyle pulled out a DVD and popped it into the player. The screen came alive with a court scene. A couple was being sentenced for IRS fraud by a panel of three judges. The next scene showed Rebecca sitting in his office. She watched as she asked him to accept a $6 million bribe to forget their IRS indiscretion. Then it jumped to the restaurant and showed her rushing to the table with her red bra in hand for him, and pulling up her skirt with a brief flash of bare torso when sitting down. Then she was in the Board Room receiving a spanking.... Her mind went numb.

"You can imagine where this could be sent. Do you want to see the rest?" he asked, a deadly calm in his voice as the TV screen showed her with skirt held high, kneeling and taking him into her mouth in the board room.

Tears were in her eyes as she watched herself putting on the red wig in the bedroom while preparing for the strip club act and shook her head no. "I can't involve Maria, I just can't. It would be too embarrassing and she might say something to John. If he finds out, my marriage will be over. You have taken over every other part of my life. Please, I need to keep this part my own."

"You might want to watch some of your act," he said shutting off the DVD player, "it was really something. It all comes back to the choices you want to make and the consequences of those choices. You will either obey me or not. It is as simple as that."

No, it is not simple at all, she thought. "I have obeyed demands that have embarrassed and humiliated me. I have tried so hard to please you. But it is never enough. You have taken my life away now as though it were nothing." She felt the tears welling up in spite of her resolve not to cry.

"And given you something you didn't have before."

"What is that?" she said a tear trickling down her cheek.

"Freedom. Freedom from the inhibitions that have held your sexuality captive. Freedom to let your true sexual nature come through. Freedom to experience a level of sexuality that most people only fantasize about. For me the cost has been many millions of dollars. Could you even go back to being the woman you were a week ago?"

She thought about it. This week had brought out feelings she had long since forgotten as well as a whole new level of sexuality she didn't know existed. She had no idea what this was going to do to her relationship with John but it would never be the same. "I would be your slave, if that's what you want, at your house. But you would have to leave me alone here and at work. It's the only way I can preserve the life I have."

"Although you didn't know what you were getting yourself into, you said you would obey me. And you have, most of the time, at least. But I demand obedience whenever and wherever I desire. And that includes here when it suits my pleasure."

She bowed her head, knowing that there could only be one outcome to the events playing themselves out.

"It won't do me any good to beg?" she said with resignation in her voice.

"No, I'm afraid not."

"What do you want me to do?"

"You will have to accept your punishment, and Maria will witness your pain and humiliation."

She didn't answer.

"Call Maria to come in here." She rose and called Maria's name from the living room entrance. Maria entered, "Yes, ma'am?"

"Sit there," Kyle directed her to the couch again.

"Finish your coffee," he said to Rebecca. Then as she swallowed it and set the cup down, "Position #1, facing Maria."

Rebecca sat for a minute numb. Then she rose, blushing, and removed her sweat top, bra, and sox. She took the sweat bottoms and panties off in one motion, hoping he wouldn't see them. These were folded and placed on a chair with the rest. Then the naked woman knelt and placed laced fingers behind her neck, her head down so she couldn't see Maria who stared wide-eyed at the high-powered businesswoman in front of her.

"Sir, please may I visit the bathroom before we start?"

He ignored her. "What orders did you disobey?" he asked from his seat at her side.

"I didn't obey you and get into the position you ordered."

"And what was the punishment the first time you disobeyed me?" he asked.

"I...I...can we please not do this in front of Maria?"

"REBECCA."

"I was spanked, Sir."

"Yes. And the second time you were punished for failing to follow an order to my satisfaction?"

"You hit me with a whip, Sir."

"WHERE?"

"On my breasts, Sir."

"So I did. This is the third time. What will your punishment be this time, do you imagine?"

She hesitated, "I don't know. That is up to you, Sir."

"Now you are an intelligent women. Take a guess, and if you are wrong, I'll add 5 strokes to your punishment."

"Oh God. Please don't hit my...my...my pussy, Sir. Please don't."

Maria had been fidgeting uncomfortably since her employer had stripped at Kyle's command. She started to get up. "Sit down," Kyle thundered. "I will tell you when to stand and when to leave." She looked at her employer for guidance, and then slumped down even more frightened than before.

"You are incisive," his gaze had never left Rebecca. "You will have a choice like last time. You may hold yourself open for your punishment and receive ten strokes, or I will tie you up and you will receive twenty five."

"I will take my punishment without being tied, Sir," she responded, not sure there really was a choice. "Please don't hit me hard like last time. I don't know if I can take it there. I...I wanted to obey you. You don't understand how hard it is to obey you here in my home in front of my housekeeper."

"I understand everything," his eyes were hard and unflinching. "Do a backbend. Do you know what that is?"

"Yes, sir." She pulled her feet out from under her and placed them flat on the floor. Then bending backward, she arched her back and put her hands on the floor over her head, her hair touching the floor. Maria looked quizzically at the protrusion from Rebecca's ass. Kyle rose and retrieved the bag he had dropped outside the living room. He pulled out a wooden ruler a bit thicker and broader than usual, and moved over to her side.

"Spread your feet wider, I want Maria to be able to see right into you."

"Yes, Sir," she said blushing again as she pulled her legs wider apart and felt her lips open.

"Maria, you will notice how wet she is," he said seeing her eyes fixated on the soaking cunt in front of her. "This happens every time I am around. I take it as a compliment," he smiled.

"You will count each one, and thank me for it," he said eying the taunt tendons on her thighs, and her breasts, which were stretched almost flat.

"Yes, Sir."

"If you make a mistake, or move from your pose, we start over."

"Yes, Sir."

With only a moderate amount of force, the ruler descended on her unprotected cunt. It hit square in the middle, with the end landing in her open hole. As the juice spattered from the force, her muscles contracted and a high-pitched scream left her lips. In a few seconds, she relaxed.

"One," she took a breath. "Thank you, Sir," she said as he dragged the wood up across her cunt.

She closed her eyes anticipating the next blow. He aimed this one lower. The main part of the ruler hit her open hole and the end landed on her butt plug.

"Iiiiiieeeeeeeeee," was the response.

"Two, thank you, Sir," she said when she could speak. Maria had never witnessed anything like this and was covering her mouth with her hand. It was so up close and personal it was almost as though she could feel the ruler landing on her, and she shuddered with each blow.

He ran a corner of the ruler over a nipple and watched as it popped back up on the other side.

Just as he saw her relaxing, he aimed directly at her clit. Her shriek left no doubt that he had hit his target. Her legs shook for a half-minute before she said, "Three, thank you, Sir." Her clit had come out of the hood as she stretched her body. Now it responded by growing still bigger with a red tinge, and she was sure it had become more sensitive than ever.

He avoided it on the next 3 strikes and her lips turned a deep pink from the unwanted attention. She was breathing heavily when he stopped to give her a break. Then he took 6 clothespins out of his bag. A nipple was pinched and twisted and a clothespin attached. She moaned as the other one was decorated to match. Then he pinched a cunt lip between thumb and forefinger and placed two on one side and two on the other. Her moans answered Maria's worst fears. A piece of duct tape was placed on each pair of clothespins and then stuck on her leg, opening her up even further. Even the lips offered no protection for the sensitive inner flesh now.

Kyle pushed his finger into her cunt and rubbed the juice around on her clit. Then a little more juice was added with a little more friction from his finger on her clit. The effects of the coffee had been building up in her and added to everything else that was happening she had to work to keep from leaking. She certainly didn't want that to happen as it would make him unhappy, as well as embarrass her further, if that was possible.

"Sir?"

"Yes, Rebecca?"

"I know we aren't done yet but I have to pee very badly."

"Yes, I know." His finger continued to massage her clit. "You are doing well. Only four more to go."

When she started to move against his fingers, he stopped. He raised the ruler and brought it down on her clit. "Aaagggaaaaa," was the response as tears streamed up her forehead to be lost in the locks of hair. "Seven, thank you, Sir."

He massaged the injured party before using the ruler on it again. The pain followed by the pleasure was driving her wild. She could feel a little pee leaking out after the last hit and squeezed harder to keep it in check. The blood rushing to her head was making her light-headed. She had to concentrate to get through this like she had her earlier punishments. She couldn't weaken and have him start all over. "Eight, thank you, Sir."