A Re-Education

"Do you know why I've called you to my office, Miss Mackenzie?" The headmaster paced slowly behind his desk, his hands clasped behind his back. Even behind his desk, he towered over Jessica, seated in front of the desk. She did know, though she was holding on to a shred of hope that he hadn't yet heard; a shred of hope that this was about something totally unrelated.

"No, sir."

"I just spoke with Mrs. Stahl." Jessica's heart sank, and felt a hot flush in her face. "She told me that she found you in quite a compromising position with Jason, tonight in the art building." He paused, and looked down at Jessica. She said nothing, and turned her bright red face down to the floor.

"And, as I understand, this is not the first time Mrs. Stahl has caught you in the art building. Much to my dismay, instead of coming to me directly, Mrs. Stahl gave you a 'warning' when she found you in a very similar situation last week with William." Jessica's heart was pounding, and wished that her chair would sink through the floor, wished that she would just disappear. "Now, Miss Mackenzie, as you know, any sexual activity at this school is prohibited. It is more than enough grounds for expulsion. For the record, please tell me exactly what you were caught doing with Jason... and William." She looked up at Mr. Green with tears welling in her eyes. "Tell me, Miss Mackenzie, exactly what were doing, and tell me what you think I should do with you."

"Please sir... don't expel me-"

"Miss Mackenzie, I'll ask you one more time, before I call your parents, put them on speaker phone and have you tell us all together." Jessica jaw dropped and she froze. "Sir, please. I'm sorry. Mrs. Stahl caught me tonight having oral sex with Jason. And last week with William also. Please don't expel me, sir. I won't ever do it again."

Mr. Green slapped his hands down on his desk and hissed, "Miss Mackenzie. I don't think you were 'having oral sex.' You were caught giving blowjobs. Isn't that correct?"

Jessica stared at the floor. "Yes."

"So, tell me again: what were you caught doing?"

"I was caught giving blowjobs, sir. To two different boys." She could actually still smell Jason on her. On top of the huge embarrassment that she was feeling, she couldn't help but have a twinge of arousal smelling his musk on her face. Of course, she hadn't been able to finish him tonight, with the interruption... "But, please, please don't expel me, sir."

Mr. Green stood upright again, and resumed pacing behind his desk "Miss Mackenzie, this is an institution of learning. As the director of this school, I have to hold students accountable for their actions, and make sure they are indeed learning." Mr. Green paused. "Stand up, Miss Mackenzie, and place your hands and elbows on my desk."

Jessica looked at the director with fear in her eyes. She did not like where this was going. But she was already in about as deep shit as possible, so she realized that she literally had to do everything he said. She stood up, and bent over enough to put her forearms down on the desk. She could see that her knees were still dirty from the art building floor.

"Now, there are different ways of establishing discipline in a school. One obvious way is to expel all students who misbehave until only well-behaved students remain. This is effective in maintaining order and discipline, but falls woefully short of the goal of educating all students." Mr. Green paced around the side of the desk until Jessica could not see him anymore without craning her neck around from her bent-over position. "The other way, which is the way that I naturally prefer, is to teach offending students an appropriate lesson. Let's call it special instruction catered to the offending student's behavior. In conjunction with follow-up lessons with that student over time, it can be ensured that their education is on the right path again. Since you've begged me not to expel you, this latter strategy is the one I plan to utilize in your case." Jessica felt a flush of relief for not being expelled, which quickly turned into a deep unease due to the fact that she had not yet considered that Mr. Green may be planning something much worse.

"Miss Mackenzie, I am going to begin your re-education by administering an old-fashioned paddling. This is your last chance to change your mind, in which case you are free to go, and call up your parents and explain to them why you have been expelled."

"No sir. Thank you for not expelling me."

With that, she felt her uniform skirt being flipped up onto her lower back, exposing her white-cotton-underwear-clad bottom to the air. She had heard of people being spanked at boarding schools before, but she had assumed that it was all a myth, that the practice had been done away with a long time ago. As she was bracing herself for the impact, she felt Mr. Green's hands on the sides of her underwear. "What-" Before she could protest, he pulled down her underwear, until they slid down over her knee-length socks and were resting on top of the straps on her shiny patent leather shoes.

"Keep your eyes on the desk, Miss Mackenzie. Now, please tell me, including Jason and William, to how many boys at this school have you given blowjobs."

"Two, sir."

WHACK. "OOWWW!" Jessica squealed.

"Miss Mackenzie, I hope that was the last time you will be dishonest with me. I am trying to help you, remember? Please don't try to pretend that I am stupid enough to believe that you were caught two weeks in a row giving blowjobs to the only two boys to whom you have done that."

Jessica was trying her best not to let go and cry all out. She was too furious with this pervert to do that. But her shame was too much, and the spot where Mr. Green had struck her on her left butt cheek was beginning to feel hotter and hotter. She started to sob. "Seven, sir."

"Seven! Well, isn't that quite an impressive number for an eighteen-year-old! Well, then, Jessica, how many of these boys have you fucked?"

"None, sir." Jessica was on the verge of blubbering now, and was glad that the director's house was well away from any other buildings where people might hear her.

"None! So, you're a little blowjob slut, are you? OK, that will be seven strokes with the paddle. Now tell me how many boys here have pleasured you?"

Jessica was now sure that something very wrong was happening, but the alternative meant expulsion and untold rage and shame from her parents. "None, sir."

"You're telling me you've blown seven different boys, and you haven't demanded similar pleasure from them?" Jessica was having trouble reading into his tone, which was simultaneously sarcastic, admonishing, and -- somehow -- hungry. "Well, then, Miss Mackenzie. I think we've hit upon where your education is sorely lacking."

Jessica began to process what he was saying, but her mental calculations were interrupted. WHACK! "Count them, Miss Mackenzie, accompanied by the boys names, please. In reverse order, starting with tonight."

"One," Jessica whimpered through a sob. "Jason."

WHACK!

"Two!" she shouted. "Henry." In the woods right before lights-out.

"Interesting." WHACK!

"Three!" Jessica had no idea how she was going to make it through four more. "William." In her favorite place, the art building. She had this spot behind the kiln that she would take them and stand them up against the wall while she went to work on them.

WHACK!

"Four!" Her ass felt like it was on fire. Although it hurt terribly, it was also giving her a strange tingling sensation in her whole body that wasn't completely unpleasant. "Simon." In his dorm room, while his roommate Sam watched. WHACK!

"Five." She hated to admit it, but the tingling she felt was localizing more and more in her vagina, just like the feeling she got when she was giving blowjobs. "Sam." While Simon watched. It was that time that she realized that boys would look at her like she was the prettiest girl in the school, as long as she was performing.

WHACK!

"Six." Her ass was throbbing now, almost past pain, but she realized that her vagina was getting wet. She felt overwhelmed with shame at her internal tangle of pain and arousal. To make it worse, Mr. Green's hand was now massaging her burning skin right where he had paddled her.

"Gabriel." Art building, by the kiln.

WHACK! "Wait. Before you tell me, let me take a wild guess... how about the only other boy on the crew team: Eric?"

"Seven. Eric." She was defeated. She thought back to that night that she and Eric were making out... She couldn't believe that it was happening; she was giddy that the hottest guy in the entire school was making out with her in the art building, after they had snuck away from the all-school assembly that night. She wanted to put into practice at school what she had learned over the summer. She had discovered that if you wanted true undivided attention and admiration from a boy, no manner of dress, flirting, or speaking could compete with locking eyes with him while you wrapped your lips around his cock.

She was sharply snapped from her reverie when she realized that Mr. Green's hand had roamed from massaging her stinging cheek to down between her legs.

"Miss Mackenzie, I'm very glad to see that you are already learning this lesson well. You're dripping wet." With that, he slid his thick middle finger, up to his second knuckle, into her opening. Instantly, Jessica's knees buckled and she fell forward with her full weight onto the desk.

"What the fuck?!? Please, sir. I'm sorry," she whimpered.

"I know you're sorry, Miss Mackenzie," purred Mr. Green in a soothing voice. "But -- you're eighteen years old, and it's far past time you learned how to be pleasured by a man." Just as he said the word pleasured, he flicked his thumb across her erect clitoris. She gasped, and he could see goose pimples rise all over the backs of her thighs.

"The kind of powerful young woman that this school is proud of producing is the kind who makes sure that she gets what she needs before attending to a man's needs."

He began to slide his middle finger in and out of her extremely tight opening, all while lightly flicking his thumb across her clit. With each thrust of his finger, Jessica felt waves of pleasure traveling up her spine. Although she knew she should be angry and terrified, her body was overwhelmed by the combination of the throbbing of her ass and the tingling from her privates.

"Are you learning, now, Miss Mackenzie?"

"Yes, sir, thank you," she slurred. She could feel his finger sliding in deeper and deeper with each thrust.

All of a sudden, Jessica yelped as she felt her pleasure intensify many times over. She looked down underneath her, and she saw Mr. Green kneeling down behind her, with his mouth firmly planted on her pussy. She began to feel a familiar sensation in her body -- one that she only felt when she was in the shower at home, with the massaging shower head... She moaned loudly.

"Miss Mackenzie, are you about to orgasm?"

"I... I don't know sir... this... sometimes happens..." But she lost herself in waves of pleasure as he moved his tongue and lips all over her. His mouth was insistent. His tongue never roamed far from her clitoris, and she could hear him loudly slurping at her.

Suddenly, Jessica felt him pull away. "Noooooooo!" She was so close to that point where her whole body released. "Please, sir..." Then she felt his finger at her opening again. But this time it felt much bigger. She looked down again between her legs, and saw that Mr. Green was now standing behind her, with his pants down around his ankles. She knew enough to know what was about to happen. "No! Please sir! Don't. I'm a virgin!"

"Miss Mackenzie, I hardly think you can honestly call yourself a virgin with your extensive 'oral sex' career. Now, you are merely learning to accept pleasure that you have been denying yourself."

With that, she felt him push into her. The sensation of stretching and fullness was overwhelming. She was glad that her hymen had broken years ago in gymnastics class; otherwise this would be excruciating. He felt impossibly big.

"That's a good student, now. Just relax, and breathe, and feel the pleasure deep inside of you."

She did feel the pleasure. She was still close to orgasm, and although she had been momentarily distracted by the change of action, her body had taken control again, and she was now moaning even louder into the mahogany desk.

"That's just the tip, Miss Mackenzie. I'm going to give you the whole thing now; I think you're ready."

He held her firmly by her hips, and pulled her to him as he leaned forward. The stretching and fullness was a sensation that she had never before imagined. She quivered as he inched himself into her. Just as she felt his hips land against her sore buttocks, she also felt something on her clitoris. She reached down between her legs and felt his balls. She pulled them tightly onto her clit. She lost all control of her body as it launched into an orgasm unlike any that she had given herself before in the shower. She shrieked and felt her pussy trying to clench around the huge penis inside of her.

"Excellent, Miss Mackenzie! On the first thrust! I see great potential in you." When her body stopped convulsing, Mr. Green withdrew from her, still fully erect. He pulled up his pants and said, "That will be all, Miss Mackenzie, please return to your dormitory now."

Confused, Jessica panted, "But... sir... I'm sorry, was I not good enough? Am I expelled?"

"Expelled!? Miss Mackenzie, you are a very quick learner, with a lot of potential. Remember, this lesson was about learning to accept pleasure before you do anything else." He smiled at her as she turned her head around. But if you're wondering if there will be other lessons... yes, I think I can teach you quite a bit."

Jessica stood up, still feeling a bit wobbly, bent down and pulled up her underwear. She couldn't tell whether she felt shame, or pride, or both. "Umm... thank you sir."

"You're very welcome, Miss Mackenzie. And, of course, this goes without saying: if anyone else hears about this, I guarantee you that my word will win out over yours. And that everyone will soon know of your devious ways."

"Yes, sir." Definitely shame. She wobbled out through his office door.

No, she thought. Definitely pride.