The Perverted Headmaster Ch. 01

Wanted to try my hand at the ever popular headmaster trope; any feedback regarding whether I should expand the story is most welcome.

All characters are over eighteen, and are entirely fictional, which should be obvious to any but the most jaded of readers.

Chapter 1

"As you can see, the position is quite effective for preventing unnecessary movement, and has numerous other benefits," commented headmaster Percival Earl Randolph Veddon to his rapt guest, fellow headmaster Charles Addington-Dervonshire. Veddon's reputation in the field of discipline was as well known among his peers as it was among his students, and Dervonshire hoped to learn a few new things during his weeklong visit to the St. Cornelius School for Wayward Girls.

The two stood in Veddon's impressively appointed office, looking down at the most recent though clearly reluctant benefactor of his infamous techniques, an occasional visitor to his office known among the teachers and students of St. Cornelius simply as 'Sweetie,' due to her mild temperament, easy-going personality and, as the headmaster had learned with great satisfaction, remarkably compliant demeanor.

The suited disciplinarians chatted casually regarding the awkwardly positioned occupant of the sturdy French style ottoman before them. Its ornate, gold-leaf legs disappeared into the plush, dark red carpet of the Veddon's office, its weight securing it against all but the most rigorous movements.

Upon the tufted, black velvet cushion stretched the slim, bottomless frame of their charge; several bright, pink stripes evident across the otherwise pale, white skin of her plump, exposed rear. Veddon had begun with her kneeling; hands on the floor, creating a lovely view of her naked sex between her spread legs and positioning her rear at just the right height, but the continual dancing about to avoid the cane had demanded an adjustment. Now, she was straddling the low piece of furniture, legs wide and sex still delightfully exposed, but this position demanded that she balance on her forearms, which severely limited her motion.

Veddon was holding a thin, flexible cane, clearly the source of the rosy stripes, but which he was currently using as a pointing device as he commented to his colleague on various aspects of poor Sweetie's situation. She had been mid-way through her punishment when Dervonshire had arrived, extending what was supposed to be a short twenty-minute punishment into a lengthy and particularly embarrassing training event for the visiting administrator.

"Note that by having the student straddle the appliance not only is their squirming prevented, but the position limits their natural tendency to close their legs protectively against the strikes."

His words accompanied a brief demonstration and the cane whooshed sharply against Sweetie's naked bottom, sending it wobbling pleasantly as a new stripe joined the display. Sweetie gasped, but didn't yell out, having learned that the blows severity increased whenever she breached this unspoken rule.

"Of course, we do not encourage an excessive use of force, relying instead on humiliation as the primary deterrent. A light reddening of the bottom, as you see here, is the proper gauge of force." Veddon tapped the rosy flesh, indicating the pinkish stripes.

"And...," Sweetie inhaled sharply as the tip of the cane lightly probed the fleshy lips of her labia, "no doubt our young charge is keenly aware that her naked, exposed sex is on full display to me."

"Isn't that right, Sweetie?" he asked almost rhetorically, but she stammered out a stuttering,

"Y-Yes,S-sir," making him smile slightly.

"Both the removal of the girls' uniform- fully, or partially, depending on the offense,"

Veddon continued, tapping the open inner thighs of the unfortunate girl.

"and the embarrassing exposure of their vulva to the male view," Veddon used the cane to once again prod the furry lips of Sweeties gaping sex, making them slick open stickily, "is the far more effective disincentive."

"The girl is also reminded that her tight, rear entrance is on full display as well." Sweetie yelped as the cane intruded between her buttocks, pressing against but not actually entering her puckered hole.

"Does that embarrass you, Sweetie?" he asked, "to have your little anus displayed so clearly to Headmaster Dervonshire and I? I wonder how you would feel to have my cane probe you, just...," he pushed the tip carefully against her puckered hole, drawing a rasping shudder, "here." Sweetie was thankful her face was hidden as she blushed hotly in response, choosing not to offer a verbal response this time.

Veddon, removed the cane and continued. "Of course, this position prevents easy removal or lowering of the panty, so that should always be done beforehand." Veddon tapped lightly on Sweetie's naked bottom, setting it to jiggle slightly.

"With her upper body pitched forward, thusly," Veddon ran the cane from her rear to her lowered head, dragging it along the length of her back, the loose ends of her top catching the cane momentarily on its descent, "the student must balance their weight upon the forearms- here." Tap. Tap. Tap.

"This restricts their view, allowing them to focus on the nature of their transgressions." The surprised yelp that Sweetie emitted as he struck her naked rear once again was accompanied with more exposition, "And," he continued, "prevents tensing in anticipation of additional blows." Sweetie yelped as the next blow confirmed his words.

"Finally, as the weight is carried quite comfortably in this position, it is useful for more lengthy punishments. Indeed, I find it instructive to simply have the student remain in position even after the punishment has concluded, allowing them time to reflect on their behavior all the while being made painfully aware of their exposure."

Devonshire nodded thoughtfully as Veddon spoke, his attention returning often to Sweetie's openly displayed sex as the cane reversed course and concluded with another series of taps on the girls' upraised nates.

"For those with such ample bosom like young Sweetie here, the removal of the blouse can provide additional embarrassment; again, a most effective disincentive to further misbehavior."

"Indeed," said Dervonshire, delighted, and Veddon, seeing his colleagues interest added, "Allow me to demonstrate."

Sweetie, would you stand, please?"

Sweetie was mortified at the exchange, knowing they intended to strip her completely; though it seemed oddly preferable to them poking randomly at her privates, and she'd been in this awkward kneeling position for some time now, her own experience suggesting it was far less comfortable than Veddon suggested. She tumbled awkwardly off the ottoman and stood shakily, smoothing the tails of her blouse down to maximize what little cover they offered of her naked bottom half.

Her two hands went protectively to cover her nakedness, but at a chirped rebuke from Veddon, she slowly placed her hands at her sides, standing bottomless before them, her hairy triangle contrasting to the pale skin of her naked legs.

She was a slim girl, not overly athletic girl but with the toned body, full breasts, and lovely, smooth skin typical of her eighteen years. Her full, dark bush offered a degree of modesty against their casual leering, but she knew her labia were unusually large, and could be sometimes be seen clearly through the dense mat of hair, especially when they swelled from her occasional masturbation sessions. With her legs held together, her lips stayed mostly hidden. She had been mortified when positioned on the ottoman, knowing her large lips would be on full display but the headmaster, if he had noticed anything unusual about her anatomy, said nothing.

"For some girls, having them remove the garment themselves proves to be more, ah, instructive, though I favor removing it myself."

So saying, Veddon reached for her blouse, tugging down to stretch it tightly across her full breasts.

Sweetie looked horrified, but permitted the headmaster to unbutton her uniform, which he did with painful slowness. After the last button, he slowly pulled the two halves of her blouse apart and, had his eyes chanced to look up, which they did not, he would have seen her face flush red with embarrassment.

Dervonshire stared openly at the exposed girl, still clad in their school-issued bra, but enjoying the swell of nubile flesh and the tiny hint of dark areola just beneath the lacy fabric. Sweetie's rapid breathing added a hypnotic up and down motion to her captive tits, and the headmaster hesitated as he reached forward once again, not exactly sure how the garment was attached.

"I- I'll take off my bra, if you please sir," mumbled Sweetie, trying to save some shred of dignity.

Sweetie unhooked the front clasp, holding the garment to her chest before sighing in frustrated resignation and removing it completely.

She was completely naked now. Standing before the two clothed, older men. She felt a warm rush of embarrassment as her hands went automatically to cover her exposed breasts and the triangle between her legs. She looked up at them pleadingly, but lowered her hands to her side once again at Veddon's wordless stare of admonishment.

"My, My Veddon, there must be something in the water here at St. Cornelius. Those are simply lovely!" and Sweetie stood too shocked to move as Dervonshire came forward, hefting her heavy, naked breasts with both hands as if weighing them like ripe fruit.

She stood passively as two sets of male eyes met hers briefly then lowered and fixed once again on her nubile breasts; nipples tingling and stiffening in the cool air.

After a few awkward seconds of gawking, Veddon grabbed a chair, brought it before the young girl, and spoke.

"A few other things to note," he said, and turned Sweetie to face away from them and with soft, but insistent hands, guided her to bend over and placing her hands together on the chair. Dervonshire appeared disappointed to lose sight of her boobs, but smiled when the view of her naked sex returned.

Veddon pitched Sweetie forward so she was bent at the waist, hands together on the chair.

"Legs apart," he continued, and the compliant Sweetie obeyed. "Good Girl," he concluded and Sweetie hated herself for the surge of pleasure she felt at the tiny compliment.

She thought to herself that this position was even worse than the one she'd been in moments before because now she was completely naked, and her bare breasts were hanging heavily down, wobbling slightly under their own weight. He back arched involuntarily, making it look like she was pushing her exposed bottom toward the two men, so she straightened it, but the combined motions make it look like she was shaking her ass, so she relaxed back into the arched stance and tried to stay still.

"Observe," said Veddon, planting a light, yelp-inducing swat across the bent-over girls' rear. Right on cue, she yelped, flinched, and set her hanging breasts wobbling, much to the great satisfaction of Dervonshire.

Veddon grabbed the pendulous teat and stilled its motion, holding it firmly in his large hand. Sweetie, was horrified to be mauled so casually but could not help but notice the warmth of the headmaster's hand; it felt wonderful against her exposed skin, and she panicked as she felt her nipples stiffen in response to the unwanted touch.

"You will note that exposing the breasts also provides some secondary confirmation of any unintended arousal that may result from their punishment."

"Secondary? Arousal? Do elaborate, my good man," said Dervonshire with renewed interest.

"Why yes. See here," and Veddon lifted Sweetie back to standing, turned her around and pointed to the newly erect nipples now protruding from the plump orbs.

"No doubt you recognize the erect nipple as an obvious sign of a young girl's arousal-" he grabbed one of the stiff nubs and rolled it lightly between his fingers, making Sweetie swoon with unwanted excitement.

"But, he continued, "this condition can arise from fear, cold, or even the simple fact that they are naked."

"See here as I stimulate it further. Note the erectile response, even in the absence of actual punishment." Sweetie hated his expertise in this regard, feeling betrayed by her reluctantly aroused body.

"Indeed," lectured Veddon, "Many young girls can become quite aroused- sexually that is- from what is supposed to be a disciplinary measure. I have been studying this phenomenon in detail and will be publishing my findings. I am sure we can talk more about this during your visit."

Dervonshire nodded approvingly, his eyes locked upon the stiff flesh.

"A more primary test of their arousal though, may be done here- "and Sweetie cried out in terrified surprise as Veddon reached between her legs, wriggled his finger through the dense forest of her pubes and pressed it firmly into her sex, moving it around with casual ease.

Sweetie stood numbly as her headmaster diddled her, much to the delight of Dervonshire, who was watching intently as the finger pushed repeatedly into the squirming girl's 'cunt', as he was thinking of it.

"An exploratory finger here is the best test of arousal, though you may need to re-position them to more easily navigate the often hairy and sometimes surprisingly tight, terrain." Veddon's finger was absurdly effective in creating precisely the situation he was checking for and Sweetie gritted her teeth as he continued.

He explored the moist depths for a few seconds before withdrawing his finger and holding it up.

"Here you see a normal amount of wetness, not indicative of any sexual arousal." He wiped the finger with his handkerchief and continued.

Dervonshire looked questioningly to his friend, "Normal?"

"It will take some experience to gauge the difference, but if your students are anything like mine, you will likely find endless opportunity to hone your skills in such examinations."

As they casually spoke, practically ignoring the terrified, naked girl in their midst, Veddon turned her silently back to the chair, returning her to the bent-over, legs spread, breast-hanging position she had been in earlier and was about to continue his lecture when Dervonshire reached between her naked legs.

"She's a bit hairier down there than most, no?" and Dervonshire grabbed a thick pinch of furry flesh, pulling it experimentally back and forth a few times, her plump labia slicking open as he did so. Sweetie could imagine him peering into her openness and whimpered in shame, but did her best not to yelp as he pawed at her delicate flesh. "And such full lips- look..."

Dervonshire fingered her dangling lips back and forth with amusement, Sweetie now certain they had spotted her 'special' attribute, and hoping their continued groping did not further swell them.

"Indeed," Veddon continued, "Most of our girls shave completely, which I find a bit modern for my tastes," but our Hygiene instructor has suggested there are health benefits to the practice."

"Call me old fashioned, but I rather like a nice, hairy quim. Don't you?" and Veddon, as casually as if he were adjusting his spectacles, rubbed Sweetie's exposed, hairy slit, his fingers splitting her fat lips and brushing her swelling clit with a thick, practiced finger.

He used two fingers to splay her lips open, peering within. "It's like a little treasure, hiding in the forest." Sweetie blushed furiously; but remained in place, though she was not sure why.

"Now Sweetie I know how naughty young girls like to play with their- "He paused, looking over to his friend.

"Say Derv" he mused, "what term do you prefer for a women's sex? My students favor 'pussy,' which does have a rather delightful sound, but I am partial to 'quim' myself."

"Well, Veddon, I always favored 'cunt.' Such a fine word, but I have heard them all. The two laughed.

"So, Sweetie, which term do you use prefer?" "Vulva?" "Pudendum?" "Pussy?" "Yoni?"

"I- I don't- don't have a favorite, sir," she stammered, embarrassed by the question. The rubbing continued. "I, I call it... my p-pussy," she stammered, quickly adding "Sir."

"Ahhh," he replied, "Pussy. Very good, Sweetie."

"So, Sweetie, and how often do you play with your...," he paused, "pussy?" All this time, Veddon had been lightly rubbing the poor girl and it was having a most unwanted effect as she was now unconsciously pushing her sex against his hand.

"S-Sometimes, sir."

"And does that make your pussy wet, Sweetie?" she hated how good his hand felt against her little knob.

"Ah. Ah. Ah," she panted, as he expertly diddled her, Dervonshire watching with great intensity.

"And what about these?" he asked, free hand moving to the nearest, hanging breast. Another finger found the raised nub of her nipple and rubbed it with practiced expertise, his strong hands surprisingly gentle as they squeezed and pulled at the soft flesh.

Sweetie's panting grew more urgent, her embarrassment momentarily forgotten as Veddon drew unsolicited pleasure from her body. She began to squirm, her rear moving in sync with Veddon's rubbing, and her knees dipping as she tried to maintain her position.

In a few seconds, she yelped loudly, her entire body trembling as she almost fell over from the orgasm.

Veddon smiled, pulled apart the panting girls' buttocks, revealing the wet, sticky slit, still pulsing in ecstasy, and indicated to his astonished guest

"Dervonshire- If you please," and the other headmaster pressed his finger into Sweeties juicy interior.

The finger he withdrew was wet with her juices and glistened brightly in the office light as Veddon concluded,

"And that- is your example of the aroused condition."