The Perverted Headmaster Ch. 02

All characters are eighteen or older. This is a work of fantasy by an amateur writer trying to learn a new skill, and happy to receive helpful criticism.

It is not intended for those of you who cannot distinguish fiction from reality, who are more concerned by minor grammar mistakes than the story itself, and who will find something to criticize and complain about despite having never contributed anything here themselves.

For the rest of you, Chapters 3 and 4 are in the works, where Sweetie will visit Dervonshire's Boys academy, and where Miss Harriot makes an after hours visit to Sweetie and Heather in their dorm..

Enjoy.

Chapter 2

Sweetie clenched her fists in frustration, her short nails digging into her palms as she vibrated in silent rage over her current situation. She stood before the massive, ornately framed mirror outside Veddon's office, staring mournfully at the twin peaks of her braless nipples poking through the thin fabric of her school blouse. She glanced up and down the hallway and finding herself momentarily alone, ran her palms experimentally over her misbehaving flesh, willing a retreat to a less noticeable condition, but sadly producing the opposite effect as the delicate touch on that overly sensitive flesh sent a hot, electrical flash through her trembling body, causing her to inhale sharply.

The utter unfairness of the Universe had her close to tears. In the weeks following her embarrassing punishment, she had redoubled her efforts to comply in every tiny detail to the many rules of St. Cornelius, navigating them skillfully and without incident- until this morning, intent on never putting herself in the humiliating position she'd found herself in earlier.

"Of all mornings, too," she lamented, realizing grimly that it was the first of the month; the start of a new demerit cycle where all the teachers and administrators would be extra alert to catch and report the first demerit of the cycle. Sweetie groaned to herself, angered to add that ignoble honor to her list of otherwise impressive accomplishments.

"I wonder what horrors the old coot will have in store for me this time," she mumbled under her breath then looking around in panic lest anyone should overhear her private musings.

Her success in navigating the schools' treacherous academic protocols made her failure at the far more mundane dress code requirements even more demoralizing. How annoying to never be commended for any of her hard work, but always be punished for these trivial infractions.

Sweetie had long pondered why some girls-like her often-annoying roommate Heather- could wear their skirts clearly shorter than the rules permitted, wear their blouses extra tight, have their shoes scuffed and unpolished- the list went on, and yet never once had she seen her punished for the very same infractions that had landed her here on multiple occasions.

When Heather had left earlier this morning, Sweetie had noticed her uniform was not even pressed, her shoes were not polished, and though she couldn't be sure, it looked like her skirt was a size smaller than usual. Had she not been in a panicked search for her missing bra, she might even have challenged her roomie on this 'special' day of demerits.

Now that Sweetie had first-hand experience with Veddon, she had come to understand these punishments were merely a thin pretense for him and his colleagues to indulge their twisted perversions. She thought back to how Veddon and his friend headmaster Dervonshire had treated her, how they had touched her and embarrassed her. As horrible as it was, a flush of hot arousal flowed over her as she thought back to their hands, touching her...there.

She took another look in the mirror, fixed her hair, smoothed her skirt then, as if admonishing her disobeying body mumbled to her still erect nipples, "Oh for God's sake go to sleep already!"

She took a deep breath, unclenched her fists, and knocked on the door.

The expected "Enter" command did not come immediately. Nor after ten, then twenty long, silent seconds. She paused, confused. Veddon arrived early, and stayed late, and was always in his office during punishment hours. Maybe because this was the start of the new demerit cycle things were different, she was getting ready to knock a second time when the door opened, causing her to stumbled back in surprise as the toothy smile of headmaster Dervonshire glared back as her from the partially opened door.

His was absolutely the last face she wanted to see, and he must have sensed her terror and confusion as he opened the door, smiling lewdly at the confused young girl.

"Ah. Miss..," he paused, pretending to recall her name, though Sweetie knew full well that he knew it. "Sweetie, right? Yes, that's it. Do come in! How lovely to see you again."

Dervonshire opened the door and gestured for her to enter, her stunned gaze locked on the smiling old Letcher. She stepped in cautiously, eyes locked on his as he closed and locked the door.

Dervonshire grinned at the quaking, young girl. "Oh, I do hope I have the good fortune of being present for another of your punishments!" he chuckled. "I did so enjoy your naked little body in our earlier encounter!" "Perhaps you will you be showing us that lovely hairy cunt of yours as well?"

Sweetie was too shocked and embarrassed by the rude comment to respond, and it did not appear that Dervonshire was really expecting a response but she felt some kind of response was expected so she choked out a stuttering reply.

"I- I- I was sent down for a uniform violation," she stuttered and added, "S-Sir."

Dervonshire's smile widened, and he placed his bony hand on Sweeties shoulder and guided her into the office and towards Veddon's desk.

Rather surprisingly, there was already another occupant seated in one of the chairs before his desk, and Sweetie was shocked to see that it was none other than one of her favorite teachers, Miss June Harriot, the young, recently hired Health, Hygiene and Fitness instructor.

Even more surprising was another extraordinary fact that took Sweetie a few more seconds to process. Miss Harriot was clad only in a lacy, pale blue matching bra and panties. She was barefoot as well, her garter and stockings seemingly laid upon the other chair before the desk.

Miss Harriot looked embarrassed to be seen in this state, her face was pink with embarrassment and she could only briefly meet Sweetie's eyes before lowering her head, remaining silent.

"Veddon is in his private office, please wait here while I let him know of your arrival," and Dervonshire knocked lightly on the closed door of Veddon's private office, then entered, closing the door behind him.

Sweetie could not believe what she was seeing. Was Miss Harriot here to be punished? She was more than interested in the semi-nude body of the very attractive teacher. She had never really seen an older (though twenty-five is hardly old) women in such a state of dress, and was immediately aware that Miss Harriot's nipples were jutting lewdly out, leaving two little peaks in the soft, silky fabric of her bra. For some reason, this made Sweetie feel better, knowing that these things happened to teachers as well.

As the teacher was seated, she could not see much else, but chanced a quick glance between the older women's legs, seeing the plump, round hill of her pubic area. Sweetie felt a little surge of wetness squirt from her own sex as she processed the view.

"H-Hello, Miss Harriot. N-Nice to s-see you." She groaned to think that maybe that would not sound right given the circumstances, but it was too late anyway.

"Hello Sweetie," the teacher mumbled. Their eyes met briefly again in a moment of shared embarrassment, and then the teacher dropped her head again and was silent.

A moment later, Dervonshire opened the private office door and spoke "Please, Sweetie. If you would join us in here for a moment." Sweetie glanced again at Miss Harriot as she stood and walked around the desk to the private office, Dervonshire opening it just wide enough for her to enter, then swiftly closing it.

If Sweetie was surprised by the sight of Miss Harriot seated at Veddon's desk, what she saw in his private chamber shocked her into open-mouthed disbelief.

There, on the darkly tiled floor of the small chamber was her roommate, Heather, and what she was doing shocked poor Sweetie into stunned silence.

Heather was completely naked, balanced on her two hands in a sort of crab-like position. Her wide spread legs faced Sweetie, giving the astonished girl an intimate view of an enormous, veined and absurdly colored pink, fluorescent dildo that she was working in and out of her aroused and clearly wet sex.

The 'thing' appeared to be suction-cupped to the floor, and it's wet, sticky surface glistened in the office lights as the young girl rocked her hips, moving the dildo slowing in and out of her hairless pussy, the creamy foam of Heathers secretions forming in small, wet droplets on the shiny tile around the massive dildo.

Sweetie watched in fascination as Heather's pussy lips alternately grabbed and released the "giant pink dick," as Sweetie's brain had since labeled it. Heathers eyes were closed, but opened briefly at Sweeties astonished gasp, but closing again as she sped up her efforts to ride the giant phallus.

Veddon stood over the young girl, clip board in hand, scribbling the occasional note and treating the remarkable situation with no more surprise than one might show attending a lecture on Economics.

At eighteen, Sweetie was no stranger to vibrators and sex toys; at least the concept of them. All the girls knew about them, talked about them, and fantasized about them. There was even a small collection of the highly contraband items passed among them with great secrecy. No one had yet been caught with one but the risk- combined with a dearth of actual boys, gave them a status of almost religious significance. To see one in private use would have been astonishing; to see one in use in Veddon's office, well, it was beyond belief.

To see Heather of all people, using it. Well, Sweetie's brain was having a hard time processing all of this, so was almost glad when Veddon looked up from his scribbling and addressed her.

"Ah. Miss Sweetie, I have been informed of your earlier infractions; as I am currently occupied with another student, I trust you will not be too disappointed if I turn over the task of your punishment to my esteemed colleague, Headmaster Dervonshire."

Dervonshire grinned as it he'd just been given an award; and Sweetie groaned as if her punishment had just been doubled.

"I will endeavor to uphold the strict standards of discipline that you have established for your young charges, and I will do my very best to fill your esteemed shoes in this matter." Veddon smiled at his friend's pompous solicitousness, and Dervonshire grinned as he motioned Sweetie to follow him once again into the outer office.

"Well," began Dervonshire as they stepped back into Veddon's office, Sweetie doing her best to ignore the half-naked teacher seated there.

"As I understand the protocol, you will first tell me the nature of the infraction, the reason you believe this infraction was committed, and then, based on your responses, I will designate a punishment I feel is appropriate to the situation. Understood?"

Sweetie nodded meekly in compliance.

"So," Dervonshire continued, "Please state the nature of the infraction you have committed."

Sweetie really didn't want to say this at all, but was even more reluctant to say it to Dervonshire, and worse still, in front of Miss Harriot, but she knew the situation would only get worse if she didn't comply.

"I- I came to school without my bra sir, and..." she hesitated. Did she really have to say it? Wasn't it already obvious? "And my n-nipples were sticking out." She groaned inwardly at the embarrassing admission.

Dervonshire looked sternly at her. "Ah. Yes, indeed. I can see you naughty boobies right through you blouse, can't I, young lady?" Dervonshire pressed a bony finger into the soft flesh, pushing the little peak into the swell of flesh. "Not exactly very lady-like now, is it?"

Before Sweetie could answer, he continued. "Surely this must be a first offense, given how well you seem to know all the rules here. Isn't that right, Sweetie?" She felt he was teasing her, but answered honestly

"My-my third. My third offense, sir" she managed to stammer out.

"Third!?" he asked, incredulous. "Surely, that can only mean you must enjoy showing off your boobies, it that so?" He continued, grinning "Well, by all means, then, please- Remove your blouse, let's have a look at them, shall we?"

'Sir?' Sweetie, asked as if unsure. "I said take off your blouse. If you are so keen to show me -- and Miss Harriot too- those boobies you are so proud of, then I will indulge you. Now off!"

Sweetie sighed, knowing this was likely, and unbuttoned her blouse and without fanfare, removed it, leaving herself topless before the visiting Headmaster.

"Yes indeed," he leered. "Those are lovely. I should think Veddon would indulge your desire to show them off and have you attend your classes topless. Perhaps I should recommend that to him. What do you think, young lady?" This idea horrified Sweetie, as an image of her attending class topless flashed through her brain.

Dervonshire hefted Sweetie's left boob, holding it as if it were a ripe fruit. "These are truly wonderful. Don't you think, Miss Harriot?"

Miss Harriot looked up, not wanting to respond, but knowing that any display of disrespect toward Dervonshire would get back to Veddon.

"Tell me Miss Harriot, are Sweetie's breasts not simply lovely?" He stepped behind the frightened girl, reaching around to grab both breasts and holding them up for the young teachers mortified inspection.

"They. Are. Very... Lovely," she managed, her face reddening even further.

"I'd estimate they are quite a bit bigger than your tiny little titties, no?" Sweetie was aghast at this comment. Miss Harriot was indeed a small-chested woman, but this seemed wholly unnecessary.

Y-Yes, Sir. They are," she stammered, her head dropping again in embarrassment.

"Perhaps we'll get to do a more direct visual comparison later," he mused, leaving Sweetie to ponder what he meant by that.

"So, then Sweetie, now we know what you have done, do you have anything to share regarding WHY you have committed this infraction?"

Sweetie didn't want to give him more time to ogle her breasts, so responded immediately, hoping to speed things along.

"I- I could not find my bra this morning sir. I did laundry last night and had it then, but could not find it this morning."

Sweetie knew this was too much information but she had been so frustrated with the loss, that the excuse just poured out of her. Little did she know that her own roommate Heather had in fact taken her bra and hidden it, knowing full well that it would mean Sweetie would be in Veddon's office this morning. That had been the entire plan. And it had worked perfectly.

Dervonshire smiled knowingly. "So, you're saying this was not intentional that you in fact don't want to show off your naked boobs to everyone?"

"N-No sir! I don't. I am a good girl, I couldn't find it, and didn't want to be late for class so..."

"I understand Sweetie, and do regret the situation, but as this is a 3rd offense of the same infraction, I am afraid that punishment is mandated. In this case, I believe 15 swats on your bare rear is appropriate. Do you concur?"

Sweetie knew of course, that he didn't want or need her approval, but she'd been through the scenario before and played along, dismayed at the forthcoming spanking.

"Yes Sir. I think that is fair."

"Very well then, please remove your clothes and I will administer 15 swats on your bare rear."

Sweetie knew she could not argue, so slowly began to remove her skirt, then lowered her panties, holding her hand in front of the now exposed dense black, bush of her pubes. She stood naked before Dervonshire, one hand covering her breasts the other her pubes as she said "I'm ready sir."

"I see you still have not shaved your pussy, Sweetie. I am surprised Veddon allows it, but I of course, delight in a hairy quim. Please, come here and get over my lap."

Dervonshire had seated himself in Veddon's chair, and once Sweetie had laid across his lap, he patted her bare rear gently reached under her to grasp one dangling boob to still her squirming and began, counting aloud. "One..."

He paused after the fifth swat, his hand sliding between her cheeks and down to her hairy nether region, rubbing her lips teasingly. She jerked at the touch, and he withdrew his hand, continuing for another five swats.

"That's ten," he said. "You're not enjoying this are you, Sweetie? If I check you for arousal as Veddon showed me, will I find you are not taking this punishment seriously?"

"Oh no sir! You can check! I'm a good girl." Sweetie gasped! She hadn't mean it, but just wanted to dispute the accusation, but it was too late; permission was given.

Dervonshire reached between her legs, which opened slightly as he inserted his hand deeper. His long finger probed through her dense matt of hair to locate the source of her slippery heat and he entered her, probing her silently for a few seconds. Sweetie groaned at the gloriousness of the feeling, hating how much she was enjoying it, but he removed his finger and held it up to the light, examining it for any tell-tale wetness.

"Hmm," he said, "I guess you were telling the truth."

Sweetie was not sure what to make of that statement. She could feel her wetness between her legs, and knew he could too, but Dervonshire simply continued the last five strokes without any further abuses to her modesty.

When he was done, she stood up, gathered up her clothes, and moved toward the corner to dress.

After she was dressed, she stood silently waiting for Dervonshire to speak. He looked about to say something when the door to Veddon's private office opened, and a disheveled and sweaty Heather emerged, face flushed pink with exertion, but with a broad smile on her face.

Veddon poked his head out of the office, and spoke

"OK. Miss Harriot, you're next."