Disciplinarian's Delight Ch. 01

"If you fail to follow these simple rules you will receive a count. The count is weighed entirely upon my feelings in regards to your violations. It can and will vary depending on what has transpired and how I perceive those actions. Realize that if you do break one of these rules that you are obligated to take the discipline I assign for that transgression. Meaning, you do not have the option to use a safe word at that time. If you earn it, you will receive it!"

His head swam with rules as she spoke. He was naked and cold and scared. He couldn=t be certain that he was able to follow these rules or even remember them.

She began again.

"After hearing the rules, do you agree and wish to continue, Edward?"

She paused. This was his last chance to stop this before it began, but she knew that he wouldn't. There was no way that he was going to get dressed and walk out now, regardless of how scared he was.

"Yes, Ma'am", He responded.

"Good, Edward, then let's get started." She walked by him, he was relieved to not be subject to her stare any longer. Her nearly constant eye contact made him uneasy. She sat on the high-backed chair that he was admiring earlier. The image excited him immediately. The combination of her dominance and her beauty grabbed his attention and caused him to stir.

She looked to him and was about to say something when she stopped. Her eyes glanced down and then she placed the hairbrush on the floor to her side and rose to her feet approaching him.

"I see that you are not ready to continue, Edward. That you are not focused. I'm growing impatient with you. Obviously you think that I'm here to entertain you, however, you couldn't be more wrong. You are here to entertain me and I don't see how this little thing peaking out from under your fat stomach is going to do that."

She said as she forcefully grabbed his cock with her right hand as she stood before him with an obviously disgusted look on her face.

"But I'm willing to give you the benefit of the doubt, Edward." She said as she released him.

"Come on. Entertain me. This is what you wanted, wasn't it? You came here for a sexual experience. I know you did. So, let's have it. Show me what you've got. Stroke that little cock..."

She paused mid-sentence, glanced down at his genitals, taunting him with her amused expression.

"That insignificant thing doesn't deserve to be called a cock, Edward. Cock sounds bigger, stronger, prouder than what you have. No, what you have is a puny little penis. So, stroke that puny little penis for me."

He looked at her in utter disbelief. Not knowing what to say and not sure he could get the words out if he did know what to say.

"I'm waiting and I'm going to continue to wait. We are absolutely not progressing until we take care of this. You have two minutes and for every five seconds beyond that two minutes I will give you 3 strokes of my cane. Wasting my time is disrespectful, we've gone over that."

She walked over and grabbed the timer from the table. He hadn't noticed it before.

Setting it she said, "Begin now."

He looked horrified and embarrassed, still not moving.

"Come on, Edward. Stroke that fucking little penis for me. I'm going to watch every second. I'm curious to see if it can bring you any pleasure, it's certainly not big enough to give pleasure to anyone else."

She grabbed his right hand and forced it onto his cock. She glared at him, teeth clenched.

"Now, Edward. One minute and forty seconds left. I bet you don't even need that much time." With that, he began to masturbate for her, but he didn't dare watch her watching him and he didn't dare watch what he was forced to do either. So, he lowered his head and closed his eyes and tried desperately to find a thought that would assist him.

"This is exactly what I was hoping for today. To have an old, overweight, sloppy, balding man masturbating for me. Come on, Edward, faster."

She shoved a box of tissues into his left hand and for a second he opened his eyes to look at what she handed him and then at her. Quickly he closed them again as he kept a firm grip on both the tissues as well as the object of attention in the other hand.

"One minute left. I thought you would have finished by now, Edward. I mean, this is exciting, right? This is erotic. This is what you were looking for, the chance to jerk off in front of me."

Stroking madly, he tried to block out the insults being thrown at him and focus on completing the task. There was no way he was going to fail and be caned.

"You had better not cum on my carpet either. Use those tissues I gave to you and hope like hell you don't miss. You might only need one, I can't imagine much coming out of that little thing." She remained there, arms crossed, leaning back against the wall with her right foot crossed over the left, watching.

Again she started. "Get the tissue ready, but don't you dare stop stroking. You have 40 seconds left, Edward. I'd work harder if I were you, unless you want to be caned?"

Edward awkwardly braced the tissue box between his knees, continuing to masturbate under her gaze as he pulled three free from the box. With the tissues and the remaining box both now in his left hand he looked up at her, questioning with his eyes what he is to do with the box.

"Set it down on the floor. 20 seconds left, Edward." She walked over and pulled the cane out of the drawer of the armoire.

Furiously his right hand pumped away.

"15." She walked over until she was standing a foot from him, alternating her stare from his face to his frantically moving hand.

His body began to stiffen and she knew the orgasm was impending. She looked at the timer....10...9...8. He would make it in time and she was mildly disappointed with losing the opportunity to cane him, however, the session was far from over and hope wasn't lost quite yet.

His hips jerked clumsily as the semen spilled into the tissue held in his right hand that was cupped in front of and below the head of his now softening penis.

Ms. Holly knelt down by the table and grabbed the waste basket. Holding it out, he quickly balled up the tissue and dropped it in, still adverting his eyes.

"Now that we've taken care of that are you ready to continue?"

He wanted to say no, but didn't. He couldn't think straight and the only thing he knew at this moment was that he didn't want to have his ass whipped now. The embarrassment and humiliation he felt and fear of what she might do next kept him from voicing his opinions, thinking that there wasn't much of a chance of him getting out of here now without enduring what she had set out to accomplish anyway.

"Yes, Ma'am." He said in nearly a whisper.

"Excuse me, Edward? I couldn't hear you. Trust me when I tell you that you always want to speak in a tone that is loud enough for me to hear otherwise I might assume you said something else...something disrespectful."

She seemed to challenge him with everything that she said. Daring him to give her a reason to push him further than he wanted to go.

With purpose the words came out of his mouth this time.

"Yes, Ma'am. I said, yes, Ma=am."

She made her way back over to the chair that she was sitting in prior to the terribly embarrassing scene that just took place. After lowering herself onto the upholstered seat, she took her hands and smoothed the skirt over her thighs before reaching down and picking up the hairbrush once again.

She patted her lap with her right hand.

"Come here, Edward. To my right. Now, I want you over my lap. I want your weight on me, not on your wrists and so help you if I so much as feel that little penis of yours twitch against my thigh after what just happened here. Realize that since you have earned the discipline you are about to receive that you are not entitled to a safe word. You will take everything I deem appropriate for your behavior and you will strive to do your absolute best to please me. I will tell you when I am ready to move on with the session that you had scheduled and at that point the safe word is again yours to use if needed."

Without hesitation he moved to her right side and folded himself over her lap. He was frightened that the soft fabric of her skirt against his groin would excite him. He prayed that she would begin before he became erect again, though he didn't want her to begin at all.

At that moment the swats began.

A slow, but steady stream beginning from the lower right cheek to the left. The intense sting was instantaneous and he struggled to remain in place. One after another they came, seeming to strike a new and more sensitive area each time. One, two, three, four, five, six.... he couldn't concentrate to count. All of his energy was focused on taking the brutal swats. He hadn't anticipated the pain hurting to this degree so early on.

He couldn't have imagined the effect of that hairbrush. His ass was on fire, burning more intensely with every well placed swat. Ms. Holly wasn't slowing down, in fact, he could have sworn she had increased at least the force of her delivery if not the speed. The swats were being to run together. He was having difficulty determining one from another with the pain from the previous swats never having the opportunity to fade.

She paused for a moment, having delivered a serious of twenty swats, ten perfectly placed swats per cheek. She loved the impression from a good wooden brush. The purple-ish red ring around the outside, leaving a white patch in the middle that within a minute engulfs itself in vivid pink.

Edward didn't have much of an ass to speak of. The typical man's ass, actually. Flat, nothing to it. No fullness or volume at all. It wasn't an ass that appealed to her sexually, but she certainly wouldn't turn down the opportunity to completely redden it. Big ass, little ass, flat ass, fat ass, it was all the same to her.

She enjoyed the art of whipping ass. The feel of the various implements in her hand, the sound they make upon impact with bare flesh and the unique marks and welts that are left behind. She loved waiting until the entirety of both cheeks were well marked and then focusing on that little crease that lies between the upper thigh and the buttock. By the time she reached that spot, the person receiving the discipline is already well spent, exhausted and more than likely in tears. It can' get any worse, they think. It can always get worse. She prides herself on that. Prides herself on always being able to take them one step further than they can go or then they think she will go. She doesn' always have the freedom to do so. Thats the drawback to whipping ass professionally, but today with Edward, she will.

She spoke to him.

"You will learn that when you are here it's all business. You will not only act and carry yourself in a way that I find appropriate you will also learn to curb the indecent and disgusting thoughts that dance around in that head of yours. When I see outward manifestations of those thoughts, Edward, as I saw today, you will be held accountable for them. If your focus is 100% where it belongs then we will not have these problems. You will not dare to become erect in my presence again. And if you do, I will wait until it's taken care of and every time it happens the consequences will become more severe. Do not think for a moment that I will hesitate in spending the entire hour caning the hell of your sorry ass if that is what it will take. Understood?"

"Yes, Ma'am. I understand, Ma'am."

He said as he caught his breath and the burning began to fade to a moderate sting. And then all too soon she began again. The swats were slower this time. One might think that slower is better, but that's all a matter of perspective. This time slower was definitely not better. Not for him anyway. Slower was better for Ms. Holly though. Slower with more force, much more force. She covered his sorry ass over and over again with those powerful blows. She developed a pattern, lower right, lower left, outer right, outer left, etc.

Edward was in too much pain to recognize any type of pattern. He just knew that the swats continued and he began hoping for an end. Never would he have thought that he would have so desperately wanted to call out his safe word so early on. He was certainly wishing he could use it right now.

Ms. Holly knew quite well that he didn't have what it would take to endure this if she allowed him access to a safe word. Though the swats weren't terribly impressive by her standards, Edward was inexperienced with real discipline. She would bet that he was likely still confused by tangible pain and that his cries didn't require the effort of acting. She wanted to ensure that his attention would remain were it needed to be and off of that little distraction between his legs. She knew his desires were what led him here, however, she wanted to make sure she made it clear that she was all business. If she lowered the intensity at first sign of his discomfort then he might perceive that as a weakness. She was anything but weak.

Edward began to squirm under the unwavering discipline she provided. He tensed the muscles of his buttocks and when the back of the hairbrush landed again it landed with a solid thud and the impact radiated up her right arm. Immediately she stopped.

"Spread your legs further apart. I want you to point your toes in toward one another and let your heels relax and fallout to the side. Do you know what that does?" She asked.

"No, Ma'am." He was hoping that it somehow made this experience more tolerable for him, but somehow he doubted that.

"It lessens your ability to clench these cheeks, Edward." She said as she pinched his ass with her fingers. He quietly sighed and shook his head in disbelief, seeming desperate and overwhelmed.

The swats continued, slower now with much less power. Less force was required at this point, his nerve endings were alive and on edge from the unforgiving disciplined received. The slightest slap at this point caused him to flinch and groan in pain. .

"Oh, Edward, is this not what you expected? Do you not find it erotic? Come on, you're here naked, over my lap with your genitals pressing up against me. It's the stuff dreams are made of! Why isn't that turning you on?" She said, her voice laced with sarcasm as she lowered her arm with the rhythm of her words.

Edward didn't respond. He couldn't. He began to give up, to give in. His body grew tired of the futile fight. His early grunts became whines; whines became moans and now the moans were becoming cries. She felt his shoulders slslump forward and this time didn't find the posture distasteful. She knew she was breaking him.