The Headmaster – Chapter 2

Sandra Matthews’ over the knee spanking began at 8:00pm, coinciding with the start of her parents’ favorite sitcom – “How I Married Your Mother”.
She started out laying across her father’s lap as he sat on the sofa. She hugged a pillow against her neck and face. He raised her school skirt up, exposing her panty-clad bottom and began spanking her.

He didn’t have to spank hard at all in order for Sandra’s already punished bottom to feel truly punished all over again. As each spank landed, first on her left butt cheek and then on her right, her head would jerk up and she would mewl into the pillow. Her mother, who relaxed in the recliner now, had given Sandra strict instructions not to cry too loudly during the show or they’d have to wait till after 8:30 to spank her and then they’d go ahead and use the belt…

All she had to do for now was to take the punishing spanking and just cry quietly. This sucked for her too, because she wouldn’t even be able to see the show very well because of the haze of her tears.

The first commercial break did not come too soon for Sandra. Her parents had agreed on using commercial breaks to make sure Sandra was hydrated with enough water consumption to endure her long punishment. Sandra, through a haze of tears and a veil of endorphins, slowly pushed herself up into a standing position, where she then rubbed her butt with her left hand and wiped tears with her right hand.

Her father volunteered to get this round of refreshments for everyone. He handed Sandra the ice water, his wife an iced tea, and he drank hot tea. Sandra drank the water thirstily and sniffled some.

With a pleading look in her eyes she asked them, “Could you please let me off of the rest of my spanking? I’ve been really punished here and I swear… I swear that I won’t do it again. Please….”

Her parents looked at one another and semi-shrugged. Her mom said, “Commercial is just about over. It’s my turn to spank her.”

She sat down and pulled Sandra down to lie across her lap. She pulled up Sandra’s skirt up and her panties down to the top part of her thighs.

“Hey!” Sandra said. “No fair!”

“Look,” her mom said, “You’re father won’t do this to you because he’s embarrassed to. But I’m not. I’m not trying to embarrass you. This will just make sure you feel it.”

‘She has to be fucking kidding,’ thought Sandra.

“He’s not looking,” she continued.

Sandra looked up to see her father staring squarely and fixedly at the TV.

And so the rest of Sandra’s spanking commenced. She found herself needing to grab the pillow even harder to her mouth in order to muffle her cries. This third spanking was really making it difficult to have a good day.

Unbeknownst to the family now engaged in an entertainment / punishment mash-up, their next door neighbor’s son, who had a massive crush on Sandra, was able to peer through a gap in the curtains of the bay window. Those gaps occurred at either edge and not in the middle, so he was able to go to one gap and observe her beet red and bruised bottom being methodically spanked. And he went over to the other gap to get a better view of her beautiful crying face. He felt so sorry for her that it only increased the level of his crush.

Liking the way that viewing this made him feel, he began working on the question in his own mind that would haunt him for the rest of his life: “How do I get to spank a beautiful girl like that?”

The Headmaster – Chapter 1

Brigitte Durning almost clipped her FBI badge onto her belt as she would normally have done on any other work day. However, this day she was to start as new History teacher – Anna Sharpe – in her first major undercover case. Brigitte new, of course, that she would never ever live it down if she blew her own cover on the first day by wearing her badge right out there for everyone to see.

She looked into her bathroom mirror and saw that her dark red hair was sufficiently un-sexied by having it pulled back and into a scrunchy that made her look much more reserved than she ever would on her own. Brigitte then focused on her eyes. No, the make up wasn’t “too much”, but she did try to soften the expression in them. Her brown eyes were expressive and confident and knowing. She really wanted to appear to be a little less knowing and less confident than she should be.


Sandra Matthews knew one thing for certain: she would be severely caned for the incident. Against school policy, the law, and any degree of common sense, she had decided to make a small business within Blenham Academy of selling off stolen prescription pills from her mother’s house. It was easy enough to get caught. All it took was for one envious cheerleader to decide to make a power play of being a tell-tale and Sandra found herself facing the headmaster.

The headmaster – Dr. David Pendrake III – peered, frowning at the report he had just read as if he couldn’t believe his eyes. He looked up at Sandra standing before him and looked back down at the paper.

Sandra thought, ‘If I didn’t know better. I’d swear he was enjoying stretching out this time before announcing my punishment. If I didn’t know better… ”


Jessica, Pima, and Rosalyn, Sandra’s friends, stood outside the door to the headmaster’s office. They began speculating about what was happening to her.

Jessica said, “If it is drugs, he’s probably going to say that he can just call the police or not involve him and give her a caning.”

“A caning,” Pima said, instinctively reaching behind her with one hand, rubbing her bottom and looking rueful. “A small word for a lot of pain. I got 3 dozen strokes once.”

Rosalyn answered, “I got 50 once myself and then got a strapping when I got home.”

Jessica said, “You know they say that there’s a vent in the teacher’s lounge bathroom where you can hear what’s happening in his office quite clearly.”

The three looked at each other for a moment, considering the idea. Jessica nodded her head sideways indicating the direction they should go. She lead the way and the others followed.


Dr. Pendrake, after giving the situation some thought, said, “You’ll need to be caned of course.”

Sandra swallowed har and her eyes widened and seemed to look far away. “Of course,” she repeated mindlessly, shaking her head slightly.

“Sixty strokes then,” Dr. Pendrake said. “Bend over my desk and grab the far side.”

Sandra walked over to the desk. The place where the desk met her hips was a bit high and she had to come up on her toes a bit to bend over the desk. As she did so, and her center of gravity shifted forward, her torso rested on the hard wood. She stretched across the blotter and grabbed the other side.

Dr. Pendrake walked around behind the desk to a glass door cabinet lined with 7 canes. He looked at the bending girl’s skirt-clad bottom and back at the canes. Sandra could see this whole interaction of course. He selected one that was not the thickest, but did have considerable density. He swished it through the air and it made almost a low-pitched “whoosh” sound. The whoosh was so low and heavy, it automatically inspired fear in Sandra.

He walked back around to stand behind Sandra and to her left. He swished it through the air once more.

“Face me, Sandra,” he said, “I have to monitor your face so that I can make sure you’re alright…. medically.”

She turned her face to his direction. From the angle he was standing he could see both her face and see her buttocks and hips well enough to make a good stroke. He took aim and gave Sandra her first biting sting of a cane stroke.

“Yeowch,” she yelped.

Even though she was being caned over her skirt, each stroke still hurt enough to be a punishment in itself. The thought that she would take 60 strokes altogether was a bit overwhelming and she began to panic and become breathless.

“Do try to relax, Ms. Matthews,” Dr. Pendrake said, “You can deal with this. One stroke at a time.”

He gave her another stroke and she yelped again. He did it a third and a fourth time, establishing a rhythm…


Whoosh, whap, “yeowch” was heard repeated at a regular three or four second intervals as Jessica, Pima, and Rosalyn listened from that secret vent in the teacher’s lounge bathroom. They knew they had limited time in there because soon the current class hour would be ending and some teachers would be coming into the lounge for their break time. Yet they had become almost entranced listening to Sandra’s caning, having not heard the beginning of it, could not be sure how long it had been happening. So they had no idea how much longer it would go on. They felt sorry for her, realizing how much pain she must be in, her bottom likely bruised by now and tears streaming down her flushed cheeks.

“Wow,” Rosalyn commented. “I hope she doesn’t have to go through another spanking at home like I did.”

“I hope so too,” Jessica said, “But we’ve got to get out of here. We don’t want to get caught.”

Jessica peeked out from the bathroom door, and seeing no one there, stepped out, motioning the other two out as well. Just as they reached the exit door of the lounge two teachers were walking in. Teachers were surprised to see students and students surprised to see teachers.


In fact tears were streaming down Sandra’s flushed face. She gripped the other side of the headmaster’s desk as strongly as if she were hanging from a cliff.

Dr. Pendrake pulled her skirt up and draped it over her back.

“You’ll get these final dozen over your panties,” he said.

Sandra pleaded, crying, “No no no no… please! I promise I won’t do it again!”

“I believe you Sandra,” Dr. Pendrake said, smiling slightly. “I believe in my heart you’re a good girl, really.”

He continued on with caning her over her panties. She wanted desperately for the caning to be over or to pass out, whichever favor the universe might grant her.

She was finally granted the former. Her sixty-cane-stroke punishment was finally over.

Sandra was allowed to stand and as soon as she did her hands flew behind her so she could rub her bottom and dance about with the terrible stinging ache. It felt to her almost like she were still being caned, which of course was unacceptable.

As she rubbed her bottom and composed herself, Dr. Pendrake dialed Sandra’s mother.

“Yes,” he said over the phone. “This is Dr. Pendrake – headmaster at Blenham Academy. Yes. Yes, I’m afraid I’ve had to cane Sandra. Yes, sixty strokes…”

He further explained that the caning did complete her punishment and that there was no need for suspension or calling the police. But Sandra knew that would certainly not be the end of her punishment. Since she’d been caned at school, she could look forward to having a very long over-the-knee spanking at home. Strapping wasn’t necessary. Each spank of  a hand on her freshly bruised bottom would be as punishing as the cane strokes. And she knew she’d have to endure at least 200 spanks.


Brigitte Durning, in the form of teacher, Anna Sharpe, after being shown her teaching room and her office, was now waiting to meet with Dr. Pendrake. While she waited, she could have sworn she heard the sound of someone saying “yeowch” over and over….


Sending a Message

Granny sat in her basement rocking chair, sipping from a glass of iced tea as she watched Jethro taking his turn at learning how to properly switch a girl. Earlier he and Granny and Ellie Mae had captured this lieutenant from their local rival club, specializing in illegal alcohol sales. Ever since they had started selling their “Bare Moon Shine”, Granny had seen her sales of “Corn Squeezings” falling off. Then this gang of motorcycle riding girls had the audacity to publicly make fun of Granny’s Corn Squeezings.

Finally enough was just enough. Granny decided she had to teach one of those girls, particularly a high-ranking one a lesson in respect. They had found out one of the places that were frequented by the girls (or the Grrrrls as they named themselves), lay in wait, and captured one at the point of a shotgun.

Now this cute, but scappy, curvy blond lay face-down over a bench in the basement of the Clampett mansion, tied there with thick rope wrapped around her torso and the bench. Her wrists were tied together and secured to the bench in front of her. Another set of ropes secured her ankles to the other end of the bench. Her buttocks were left free of course in order to receive the very long switching she was now receiving.

Granny had started her out, giving her a hundred or so moderate strokes with the three-foot long willow switch she had had Jethro cut for the occasion. The blonde had tried to be tough at first, but now she was just crying and asking why a lot and promising to do anything…

Granny had handed the switch to Jethro to use on her in the hopes that he would become better at this task. She was grooming him to become chief of security in her operation and was determined to have him be good at punishment. If he was going to help enforce discipline, he’d have to be a good whipper. And the switch was as good a place to start as any.

The girl’s bottom was, at this point covered in red stripes and bruises and she was crying like a punished young girl.

“Jethro, ” Granny asked. “How many have you give her so far? You been countin’?”

He stopped the switching for a moment and mopped his brow with a little hand towel. “Oh about 150 I recon… ”

“Okay,” Granny continued. “See there. Look at how she’s got most of her bruises on one side.”

Granny waited while Jethro inspected the girl’s ass.

“Yeah, Granny,” he said.

“So now I want you to go around and whip the same amount from the other side,” said Granny. “Even her out.”

“No! Please no!” said the girl, understanding that she was about to get another 150 more strokes of the switch. She was confused about what was happening and didn’t know their goal. They hadn’t even asked her any questions.

Interrogation Spanking

“Both of you will be whipped this way until you answer the question,” Imperial Agent Gartner said cooly, almost bored. He walked around behind Agent Melissa Werner who was bending over, strapped down onto an interrogation block. After forcing her to bend over the block, two lower ranking agents then stretched her arms in front of her and cuffed them to the block. They then secured the waist strap that would keep her from wriggling her hips too far and avoid the heavy strap that was soon to lay into her. They then unbuttoned and pulled down her pants. They started to pull down her panties as well but, but Agent Gartner stopped them, saying, “Let’s allow her just a bit of dignity. After all she’ll soon be crying like a child.”

In the position Melissa was in, looking in the forward direction she could see through soundproof glass that her partner, Agent Jack Rogers was in the same position as she was, bending over an interrogation block and tied down, seemingly awaiting the same fate. Behind him stood a female Imperial Agent who, after pulling his pants down, opened a cabinet in the room and selected a very long and heavy strap. Melissa heard a cabinet open behind her and was horrified to think what might be in the process of being selected for use on her. She knew she was in for a lot of pain and, apparently, so was her partner. Of course they both had been in the service long enough that they knew very well, intellectually at least, the very real danger of being captured and interrogated. But it was like any other disaster in life, they didn’t see it happening to them. They each re-traced their steps in the mission – the flight plan, the cloaking devices, a way to get the data back home… Where had things gone wrong? Each intended to try to take themselves mentally out of their situations by focusing on the analysis.

The pain of the first stroke with the heavy strap was intense enough to cause Melissa to let out a guttural moan. Her eyes widened in surprise. She swallowed hard and shook her head as if trying to shake off the pain, but the pain took its time, dissipating ever so slowly until… With another whack of the strap against her bottom the pain built back up again and surpassed it’s previous level.

“OOOO!” she cried out, trying on anger as a means of dealing with this level of pain. She stared across at her partner, who although she couldn’t hear him, saw his eyes squint while gritting his teeth as the woman in his interrogation cell walloped him with her carefully chosen heavy strap.

Agent Gartner punished Melissa with eight more strokes in a steady old-fashioned strapping rhythm and then stopped to talk to her. She dropped her head down and whimpered, a tear rolling down each of her blushing cheeks. She was breathing heavily.

“I know. I know, Melissa. It hurts,” I.A. Gartner said. “I wouldn’t want to go through this either. And see your partner across the hall? He doesn’t like it much, certainly. But you have a choice. You can make it stop. Just answer my question and it will all stop. I’ll stop strapping you and she’ll stop strapping him. We’ll all go to lunch…”

Melissa craned her neck around to shoot him an angry look, to which he chuckled and said, “I’m joking about the lunch. I’m sure us fraternizing is frowned upon. Besides that, would you be able to sit?” He chucked again at his own jest.

Jack was getting a very similar talking to after his first ten strokes with the strap. He couldn’t help feeling chastised because strappings were how he was disciplined at home, up through his teen years. And typically it was his mother who had administered them. The only difference was that she didn’t tie him down. He was expected to hold onto the far side of the workbench and not to let go or the count he was to receive would re-start. So he wanted to answer her questions because he no longer wanted to be a bad boy.

Having the two see each other suffer was a brilliant plan. It’s one thing to martyr oneself and take the pain of strapping for the good of the cause. It’s another thing to condemn one’s brother in arms to the same fate, when it was avoidable. The only thing each of them had to keep going on was the understanding that the other would want to make the sacrifice for the sake of the mission. But how long would they continue to choose getting strapped over answering a few simple questions?

Each of their strappings picked up again, expertly and professionally laid on, stroke after painful stroke in a steady rhythm – whack, one, two seconds, whack, one, two…  And after each whack, a cry of pain or determination or anger, a pulling against bonds, and finally more tears.

The second round of their strapping consisted of twenty strokes with the heavy strap. Next would be forty, then 80, and they would continue to double until someone answered or someone passed out from the pain. After being revived, the questions would be put to them again.