The following story was written by inspiration from a fantasy dialog between a very good friend and myself. She likes to be called Countess Devane and helps to keep me young. I worked very hard to keep the dialog as it was originally, and spontaneously, projected, while filling in enough detail to help the reader experience what we did. Please enjoy!
As headmaster of a girls’ private school, Mr. Michaels had to pay careful attention to appearances. At the moment, all students and faculty were in the auditorium for a performance of “The Nutcracker,” and this was one of the few times he could personally inspect the girls’ living conditions without someone looking over his shoulder. While his reasons for not wanting the housemother present during his inspection were mostly personality driven, he found there was a certain excitement associated with a view of the girls’ intimate belongings while in the privacy of his own thoughts.
The first two rooms he peered into were actually rather tidy, but the third room was a disaster. It looked as if some young lady had been in an awful hurry to dispose of her books and change in time for the mandatory attendance of the play. The bed was unkempt, and he surmised she had been behind in her schedule all day, if not longer. He smiled at the panties tossed near the foot of the bed, and the lacy bra nearby. Just as he was about to reach for the panties, a young lady burst into the room, oblivious to his presence, and obviously in a rush.
“Oh!” the young girl gasped as she saw the headmaster. “I … I was using the facilities.” She knew she was far too late for the scheduled event in the auditorium, and she was at a total loss of words as guilt permeated her face.
“Sit down, my dear,” the headmaster directed with a soft, but firm voice. “What’s your name?”
“Isabelle,” she answered as she sat on the side of the bed, partially concealing the discarded underwear he had already noticed. She was quiet and demure, as a young lady was expected to be, and dressed in the school’s standard white polo shirt, plaid skirt, and knee high white socks. Her light brown hair was braided in pigtails that reached behind slender shoulders and down her back.
“Young lady, this may be your room, a place where you may usually relax, but surely you know at your age you do not sit with your legs spread apart in the presence of others.” A glance from the headmaster had made him privy to a generous portion of her thighs, and he found himself twitching at the thought of what lay beyond.
“Oops,” she giggled as she closed her legs demurely and looked at Headmaster Michaels. He seemed young for a headmaster, and physical fit as well. Many of the girls had fantasized about him as they saw him jog around the campus, or had the pleasure of encountering him in an academic setting.
In an effort to distract his own thoughts, the headmaster looked around the room with a solemn face. “Your room is a disaster. Do you have any explanation for the state of your room, and your absence from the play which,” he looked at his watch, “has already begun?”
Isabelle thought desperately, but there was no satisfactory answer. “No, Sir. It is a mess.” She looked around and then back to the headmaster, but with lowered eyes. “I’m sorry, Headmaster.”
“I believe punishment is in order,” Headmaster Michaels concluded. He trembled inside at the thought of spanking her himself, then realized that was in fact a possibility. He knew the housemother’s reputation for discipline. She had no tolerance and her judgments had a way of building upon each other. She never seemed to forget, and it was usually in each girl’s best interest to avoid her at all costs. “Do you want me to involve the housemother?” he threatened.
“Is there an alternative?” Isabelle pleaded.
“It is within my authority to punish you myself,” the headmaster spoke without emotion. “We could get it out of the way right now, and it need go no further … provided you learn your lesson.” The young lady seemed to consider the options. She wasn’t sure what Headmaster Michael’s punishment would be, but she was aware of no reputation concerning him. While Miss Jacobs, on the other hand …
Headmaster Michaels reached around and repositioned a desk chair before sitting and facing Isabelle. “Come, lean over my leg,” he instructed.
Isabelle was wide-eyed. But she figured she better comply. It stilled seemed the better alternative. She stood slowly and stepped toward the side of him she would lean from. Hesitantly, she bent over his legs, already bracing herself for the spanking she knew would follow. “I’m sorry,” she repeated, with more conviction than before.
The headmaster couldn’t believe the feel of this eighteen-year-old feminine body lying over his legs. He dutifully raised his hand to exact punishment in as clinical a manner as possible. WHACK … the girl’s skirt provided more cushion than he anticipated. He increased the force of the hit, WHACK, and she squealed a bit. Finally, he lifted her skirt and laid it along the small of her back. Her white cotton panties rippled with the movement of her butt cheeks as she squirmed. WHACK. She squealed more freely, in a mixture of pain and delight.
As he brought his hand back for another hit, he felt coolness against his fingers that told him they were damp. He hesitated, looked at his fingers, smelled them, then leaned over slightly to see that her panties were damp. “Why is your underwear so wet? Have you not changed them recently?” He smacked her again before she could answer. “Take those dirty panties off right now,” he demanded.
“Yes, Sir!” Isabelle obediently stood, reached under her skirt, and pulled the panties down to her feet.
The headmaster felt a surge of electricity just seeing the panties separated from the girl’s privacy, and imagining how she must look under her skirt without them. Under the guise of further inspection he quipped, “Give them to me.”
Isabelle quickly and quietly stepped out of the panties, picked them up, and handed them to the headmaster. Her own feelings were stirred as he lifted them to his nose and took a whiff. She looked for any sign of pleasure on his face, any hint that this had changed from discipline to … something more. But he remained emotionless as his eyes looked above the panties and locked on hers.
“You haven’t learned to keep clean?” he asked.
“I wasn’t ever taught,” Isabelle bit her lip.
He directed her to lean over again and proceeded to lift her skirt as before. Her bare cheeks were slightly pink from his earlier attacks. He was aware she had turned her head to look at him as he tried to hide the aching lust that grew within. His face remained stern as he lifted his hand and brought it down with a loud smack. He tore his eyes from the target to see her reaction as he lifted his hand again.
Isabelle blushed crimson as she squealed. She turned away while he prepared for the next spank.
His hand swung down and connected with the pliable skin, SMACK. He hesitated too long to remove his hand, however, and it slipped down a little, at which point he declared, “You’re dripping!” He knew why, of course, but strained to maintain a sense of control and discipline.
“Yes, Sir,” she acknowledged and squirmed with a degree of excitement she did not quite understand.
The movement caused him to feel how wet she had made his pants leg. “Look what you’ve done to my pants! Stand up and see what you’ve done!”
“I’ve made another mess, haven’t I?” she asked. But she was looking at the bulge in his pants as she rose to stand again.
“Yes, you have,” the headmaster spat at her in an effort to appear angry. As he took his own pants off, and only hoped her fear of his wrath would overcome her reasoning skills. On the other hand, he was loosing control. His arousal was so strong that he was already near the point of no return.
When Isabelle saw his erect member peeking through the slit in his boxers, she gasped at the size of it. “Oh my, Headmaster. It’s so … large.”
The headmaster ignored her comment. “Your skirt is wet and dirty too. Take it off.”
Isabelle obediently shimmied out of the skirt. Embarrassment took control as she hoped her shirt would hide her privacy. Her hands dangled and fidgeted in front of her for added protection.
“I see the underwear on your bed, but with your panties dirty, I must question whether you change your bra as often as you should. Is it dirty as well?” he challenged even as he looked and couldn’t be sure if she was even wearing a bra.
“I only have one bra,” she explained in a pleading voice. “To be honest, I don’t even like to wear them.”
“You naughty girl!” the headmaster fumed. “Take off that shirt. We might as well start from scratch.”
“But bras are so itchy and constricting,” she defended.
“Do I have to teach you everything?” the headmaster sounded exasperated, “More discipline is in order.”
“Yes, Sir,” Isabelle gave in, unbuttoned the neckline, and began sliding the shirt off, letting it catch on her elbows.
Headmaster Michaels let his eyes fix on the young girl’s breasts as they were partially revealed when her shirt caught. They wiggled as she tried to move the shirt further up. When he realized her shirt was stuck, he grabbed the portion over her head and ripped it up and out of the way, letting it land on her roommate’s bed.
“Oh, Headmaster, please don’t hurt me,” Isabelle pouted.
The headmaster responded by sitting back down, taking Isabelle’s hand and pulling her naked form back over his knees. This time it was flesh against flesh as her flat tummy pushed his shaft down the slit of his boxers, and her breasts pressed softly along one side of his left leg. He felt heat emanating from between her legs against his right leg as he cocked his arm for another spank.
SMACK! Tears came to her eyes as she squealed.
“Do you change your clothes every day?” the headmaster asked as he administered another spank.
“No, Headmaster,” Isabelle managed just as the next smack landed on her stinging bottom. A rush of air escaped her lips with each impact.
“You are a naughty girl, Isabelle,” the headmaster hesitated his raised arm before another hit.
Isabelle sobbed softly with the momentary reprieve. “Yes, Sir.”
The headmaster slammed his hand down even harder, but his control suddenly dissipated as his hand remained on the red-hot skin of her cheeks. Isabelle squealed for a moment, then relaxed under the feel of his lingering hand. She felt his hardness against her tummy, and noticed a wetness where it’s tip bore into her. With pretense wavering, Headmaster Michael’s hand moved slowly down between Isabelle’s legs, toward the flower of her youth. “You are wet,” he whispered hoarsely. “Do you have a problem?”
Isabelle moaned almost inaudibly. Her pigtails dangled on either side of her face as she shook her head. “No, Sir, no problems Headmaster.”
The headmaster stared into space as his hand remained cupped over her wet lower lips, the soft curls of her slick pubic hairs giving way below his fingers. “Have …,” he cleared his throat, “Have you had your annual examination this year?”
“No, Sir,” was the reply he hopped for and received from the soft voice below.
“Perhaps we can take care of that right now,” he offered as he pressed her lips apart and began an exploration of her vagina, “and find out why you seem to be having trouble with wetness.”
Isabelle moaned and wiggled a bit.
The headmaster located her clitoris erect within. “What does this feel like?” he asked clinically.
“Oooohhh Headmaster! It feels odd. I’ve never had anything but another girl’s tongue there before.” Isabelle spoke with no more inhibitions. Then she realized what she had done.
“Other girls lick you there?” the headmaster sounded incredulous, but his excitement jumped up several notches. “I can’t believe it!” he scolded. There was no answer from the tantalizing body as she squirmed around his probing fingers. “I want you to understand exactly what you’re talking about,” he finally stated as he pulled his hands away from her body. “Lay on the bed, My Dear, as you would lie down to be licked.”
Isabelle was practically shaking, more with excitement than fear, though the feelings were strangely mixed. She felt his shaft rise with her tummy as she stood to move toward the bed. The head of his shaft was shinny as the skin stretched seemingly as much as it possibly could. It seemed to have a life of its own as it throbbed toward her. She pulled her eyes away to obey the headmaster, and stretched out on her bed.
The headmaster eyed her greedily as she positioned herself. “Tell me if this is what they do,” he knelt down between her legs and licked her swollen lips.
“Mmm. That’s how they start, Headmaster,” she responded.
“Really!” the headmaster sounded unbelieving. “And do they do this?” He wrapped his lips around her clitoris and pulled lightly.
Isabelle spoke through labored breaths, “Oh yes, Headmaster, they do that also … and they nibble on it, swirling their tongues all over.”
“What about this?” the headmaster jabbed his tongue in and out of the young girl’s entrance.
She moved against the bed and moaned, “Mmm, yes Headmaster.”
The pain of Headmaster Michael’s throbbing shaft was more than he could bear as he ran his tongue around the girl’s erection. He stood up and leaned over her, speaking down to her with all the authority he could muster, “You should not let girls do those things to you!” Even as he spoke, he realized his shaft was leaning against her pussy lips.
Isabelle looked properly chastised, “I’m so very sorry, Headmaster.” She moved against his hard member. “If not girls, who should I let do those things to me?”
The headmaster’s mind was spinning. “Be quiet when I’m addressing you!” He leaned harder, the head of his shaft parting her lips.
Isabelle gasped, “Yes, Sir.”
“I want the names of any girls who have licked you down there,” the headmaster insisted as he pushed past her opening.
Isabelle gasped uncontrollably, “Ah … I … I can’t, Headmaster. … I don’t want to get them in trouble too.”
Headmaster Michaels gasped too, as he felt the obstruction he wondered about. In that frenzied moment, he realized she was still a virgin. Despite her obvious promiscuity with members of the same sex, she had apparently gone no further. If there was any conscious left in him, it was too late. Nothing could keep him from the incredible sensation that loomed just over the horizon. “You MUST tell me … or face severe discipline.”
Isabelle held fast to the loyalty she had with her friends. Besides, deep down she wanted the discipline that the headmaster seemed to threaten. And so, in the throws of passion she had never known before, she persisted in the negative, “But I can’t, Headmaster. They’re my friends. I can’t be a tattle tail.” Little did she know he was cheering her on, hoping against hope she would provide him some small measure of excuse to keep going.
“You MUST,” he repeated as he forced his shaft through the obstruction with mock anger.
“I CAN’T!” she screamed, as he penetrated her, taking from her that precious gift she could never give again. The pain was harsh, but ecstasy rode over the top and carried her to new heights of pleasure. She was filled, and he remained there, not pulling out, not moving at all, except for the effects of his labored breath above her.
Through gritted teeth, the headmaster spoke again, “If you do not tell me the name of each girl that has licked your vagina,” he paused for effect, and to maintain composure, “then I will have to discipline you every day until you come to your senses.”
Isabelle panted softly, “I won’t tell you, Headmaster.” And with more forceful resolve, “I won’t!”
The headmaster looked into the young girl’s eyes. The two of them silently stood ground, not wavering, but each knew they wanted this. Only the very back of their minds tried to whisper how it was wrong. Neither dared entertain any thought that would deter them from continuing. “Then I have no choice,” he said gruffly, and followed by slamming in and out of her virgin cunt with every ounce of energy at his disposal.
Isabelle screamed in ecstasy, “Oh! Headmaster! Please forgive me!”
The headmaster spoke only during thrusts, “I can’t … forgive … you … until … you tell … me … their names.”
Isabelle alternated between deep harsh moans, and high squeals, “I … I won’t! … I can’t.”
“So be it,” the headmaster declared through gritted teeth as his balls tightened up.
She raked her nails down his back. “Please, Headmaster, please!” she yelled as she continued to scream and squeal in ecstasy.
Headmaster Michaels sped furiously through the next several thrusts to get them in before holding fast and exploding deep within her womb. He held her tightly against him as he felt himself pulsate within her tight walls with each of several spurts.
Isabelle felt it too, and moaned with each contraction around his pulsating member. “Oh, Headmaster! What have you done to me?”
Now it was Headmaster Michael’s time to buckle or maintain resolve. “I will exact discipline upon you every day, until you tell me the name of each girl who has licked you. You will report to my office at 4:30 each afternoon following your last lecture, until such time that you can be obedient. In addition, you should consider the leniency of my discipline. If you tell others, they will be jealous, and Miss Jacobs will find out. When she does, she will administer her own discipline to make up for it.”
“Yes, Sir,” Isabelle pouted while feeling delighted inside. “Am I dismissed, Sir?”
With a wicked grin, the headmaster answered, “Not until you clean up this mess.” Isabelle started to pick up the tossed clothes. “This mess,” he clarified by pointing to his limp shaft.
Isabelle didn’t seem shocked as she knelt before him and asked knowingly, “How would you like me to clean it, Sir?”
“Lick it!” he commanded.
“Yes, Sir,” she responded as her warm, wet mouth encompassed his big shaft, making it grow again. Moments later, when the shaft was hard between her lips, she slid easily in both directions, and cleaned it quite well. But she didn’t stop with cleaning. She flicked her tongue over the top to catch a drop of cum oozing from its tip. Then she licked her lips and swallowed deep.
The headmaster was amazed at her apparent expertise. “Ooh,” he groaned. “You’ve done this before. Haven’t you, you dirty little girl?”
“Only for the good grades I get from the male professors, Headmaster,” she offered as she dropped her mouth back down over his cock, purposefully cramming him as far into her mouth as she could, feeling those little streams of cum slide down her throat.
“Naughty! Naughty!” the headmaster’s eyes went wild, both from her ministrations, and the information she just shocked him with.
Isabelle held him deep in her mouth. She figured she was in control now, as she slid back up against simultaneous sucking, stopping just short of letting the head pop out of her mouth. Her tongue rolled all around it, feeling the veins and smooth skin. His pulses beat against her tongue. She grabbed the base of his shaft as her mouth slid quickly up and down. Her hand moved in time with her mouth, while her other hand massaged his heavy balls. To his delight, she groaned with pleasure.
“You realize, my little slut,” he spoke with a different tone, “you now have to tell me which professors you have done this with. Ooohh, Hmmm!”
She knew what she was doing to him. “… or what, Headmaster?” she asked with mockery and amusement in her voice before crashing back down his shaft.
“You challenge me, you dirty slut! Lean over the edge of the bed … NOW!”
She let the hard cock pop out of her mouth once more as she contemplated the spanking she was about to receive. “Yes, Headmaster,” she whimpered slightly, partly because she did not get to finish sucking him.
But the headmaster did not step to the side of her to administer a spanking; he maneuvered between her legs, pulled her ass cheeks apart with his thumbs and positioned the head of his solid shaft at the back of her ass. “You asked for it!”
Suddenly realizing what was happening, Isabelle became frantic. “Oh, Headmaster!” she gasped, “No one’s ever even seen my bottom, much less touched it.”
“Names?” the headmaster said simply.
“I can’t, Sir. I don’t want to get them fired, Sir!” She would not make the mistake of mouthing off to the headmaster again … or would she.
“NAMES!” He smacked her right ass cheek with his right hand, immediately eliciting a continuation of earlier pains.
Again she squealed, “I can’t! I don’t want to get them fired, Sir.”
“Last chance! NAMES!” SMACK! SMACK! His pre-cum provided some coating, and he reached his left hand around her hip to gather some juices remaining at her pussy lips and provide further lubricant for her anal opening.
Isabelle couldn’t quite fathom what he was doing, just that each touch sent shock waves through her body. She felt him rub around her little hole, but mostly she felt the sting of his right hand as she sobbed loudly, “I … can’t, Sir. I just can’t! It would kill me to know I was the cause of their termination!”
Excellent, the headmaster thought … an excuse for what he was about to do, and assurance that she could keep a secret … his secret. He grabbed her hips and thrust his shaft deep into her tight little hole.
Isabelle grabbed the bed beneath her and screamed with pain and pleasure.
“Oh God!” the headmaster breathed as he held firm within her bowels. The pressure on his shaft was beyond his experience. He could feel the rumble of an earthquake deep down begin to surface. His body was about to shake, he was sure, and he began to pull back and thrust again, and again, before it was too late.
Isabelle moaned and pushed back against the headmaster. She never dreamed of such feelings as juices ran down her legs. Even as he called her a disobedient wench, a wave of stimulation flowed through her and caused her body to shake uncontrollably.
Both of them thought of her pussy at nearly the same time. She reached down to rub herself, and he found her there with his exploring hand a moment later. “You slut! You’re feeling yourself, aren’t you?”
With her other hand, she held on to the sheets for dear life. “Yes, Headmaster …” she gasped, “but only because I thought you might approve.”
“You should NEVER feel yourself,” the headmaster instructed emphatically.
“But … but … Headmaster, why not?” she whined.
“Because,” the headmaster pressed his own fingers passed hers and began rubbing her clit, “only a MAN should touch you there.”
“A man like you, Headmaster?” she asked knowingly.
“Yes,” he answered as he continued pumping her ass, “a man like ME!”
“Mmmmm, yes, Headmaster,” she purred softly, pushing against him.
The seduction of her answer sent him over the top. He stiffened deep within and unloaded his second climax within her gorgeous body.
Isabelle screamed in ecstasy again and again. “Oh Headmaster! Thank you!”
“You WILL learn obedience,” he declared, “though it appears it will be the ‘hard’ way.” He smirked at the double meaning.
“Yes, Headmaster,” she responded with eyes lowered in submission. But disobedience was so much fun, she thought. She looked forward to submitting herself for discipline each day.
~ * ~
As Headmaster Michaels walked past the hoard of girls heading toward the dorm behind him, he snickered with two final thoughts. Isabelle may have missed seeing the ‘Nut’ cracker … but he didn’t! By the same token, who was really the ‘head’ master?