Discipline
“Oh fuck, oh fuck, oh fuck…” Lilly chanted inside her head, “I am so screwed, they are going to nail my ass to the wall for this…”
She wandered slowly down the ornate hallways that made up the heart of the original monastery, the magnificent hallways for once failing to have the awe inspiring effect, lost as she was in her inner turmoil. Lilly’s mind provided a host of terrifying punishments that she was just positive were waiting for her in the headmaster’s office. With all the thoughts of punishment she was sure were just around the corner she didn’t know what she was going to do…
Lilly knew that her parents were practically bankrupting themselves in order to pay for her tuition here, and despite the cost and the burden that it was placing on the family they had been over the moon when her acceptance letter had come. Her mother had lectured her nearly every day since about how important a good education was to securing a future.
Though really, the education speech was a bit of a conflicting message, since her parents had always told her that she needed to be humble and submissive in order to find a good husband who would take care of her and provide them with grandchildren… But since when did parents ever make sense?
Lilly heart beat faster with every step she took towards the headmaster’s office, the impending discipline, and the very real potential for expulsion, made the trip seem to simultaneously stretch into infinity and speed past, giving her perceptual whiplash.
She stood before the ornately carved wooden doors that separated the headmaster’s lobby from the rest of the school. The last time that she had stood before these doors had been during her introduction to the school, her heart filled with awe at the beautiful architecture that the school boasted and anticipation of everything she would accomplish during her time here. Now all of that had turned to ash in her mouth, and she faced the probability of her time here coming to an abrupt end.
She didn’t know what she would tell her parents if they kicked her out…
“No! I must not let that happen!” She said, mentally reprimanding herself for even allowing such a thought to occur.
She had just made a mistake, she was sure the headmaster was a reasonable man, she was sure that if she just promised to shape up, and showed true remorse, then she would be ok. Maybe she could offer to do some community service or something? At this point she would do anything to stay here…
After a moment of trepidation Lilly hesitantly knocked on the ornate doors, the muffled impacts sending shivers of dread down her spine.
“Come in please.” A voice called.
Obediently Lilly entered the office, softly closing the door behind her, the sensation of being trapped, with no way to escape, was nearly overwhelming. For a split second Lilly nearly turned on her heel and bolted like a frightened rabbit.
“Ah, Miss Anderson. We have been expecting you.” A frosty feminine voice greeted her.
Lilly suppressed the urge to flee with force of will and turned to face the voice.
Mrs. Johnson was practically a fixture in the school. Although she was young, barely past her mid 20’s, she was warm and possessed a level of diplomacy that not only made up for her youth, but compensated for the brilliant but blunt headmaster. It also helped that she was absolutely gorgeous. Long dark hair that had its fair share of natural wave was paired nicely with a dusky complexion that gave her an exotic appearance. Her overall beauty was enhanced by her proclivity for low cut shirts, which served to showcase her more tangible assets.
Lilly was a little disconcerted that Mrs. Johnson, who was a friend to everyone, was rather chill with her. To make matters worse Lilly found her eyes pulled to the heaving expanse of exposed flesh, the sight of which caused Lilly to experience something that she had never had in conjunction with a woman before… arousal. Even through the haze of anxiety that she was currently enveloped in the mental image of the other womans bare breasts covered in a sheen of sweat, her face contorted in pleasurable release, shot through Lilly’s mind.
“Miss Anderson!?” Mrs. Johnson said sharply.
“Oh, yes? Sorry, I didn’t hear you.” Lilly said flushing a brilliant scarlet color, shame filling her at the contents of her thoughts that the other woman’s exposed cleavage had elicited from her.
“I said you may enter the headmaster’s office, he will be with you shortly.” She repeated, the frosty tone even more in evidence than it was before.
Her head hung in shame Lilly missed the slight twitch at the corners of the older woman’s mouth that hinted at a sardonic smirk, evidence that not only had she noticed Lilly’s gaze, but she had been able to correctly guess the contents of her thoughts.
“Yes, Miss.” Lilly said submissively.
The headmaster’s office was a sprawling, and rather impressive affair. Every bit of it demanding the level of respect that befitted a man who ran the most impressive private school in the area. Full length book shelves covered most of the walls, each shelf stuffed full of what were no doubt expensive and unique manuscripts.
Lilly turned as she heard a door off to one side close softly as the headmaster stepped out of his private washroom. He glanced at her, his eyes scanning her thoroughly. Although it lasted only a moment Lilly felt as though she had been turned inside out by his measured gaze.
“Ah, Miss… Anderson isn’t it?” He said. He raised one eyebrow quizzically.
“Yes sir.” Lilly answered meekly.
He walked past her and stood in front of one of the full length windows as though utterly disinterested in her presence. She waited a moment, unsure about what she should be doing until he broke the silence again.
“I trust you know why you are here, yes?” He asked, his tone gave clear indication that this was really more of a formality than an actual question.
“I do, yes sir.” She answered.
“Then you know of course that I have no choice but to expel you immediately. The type of behavior you have displayed during your short career at this school is utterly unacceptable.” He said.
“Please! No!” Lilly pleaded.
“I don’t see as how I have any other choice. I would like to see you succeed here, but your behavior seems to indicate that you are just not the right fit for our school.” He said
“Please, give me another chance. I promise I will do better… I will do anything!” She said. Her voice quivered as tears ran silently down her face.
The headmaster turned around, as though this was exactly the phrase that he had been waiting to hear.
“Anything?” He said softly
“Yes! I will do anything to stay here! Just tell me what you want me to do.” Lilly said.
Her eyes sparkled and the flush of color had returned to her face at the prospect of having some way out of the trouble that she was in.
“Alright, strip.” The headmaster said.
Lilly’s heart skipped a beat. She could not have heard what she thought she had just heard…
“Sir?” Lilly said confused.
“You want to stay don’t you?” the headmaster responded.
“Yes…” Lilly said
“Then strip!” the headmaster said.
He matched his command with action. He grabbed either side of her shirt and ripped it open in one motion, exposing her bright pink bra.
Lilly knew she should have been shocked, she should have been angry, she should have been any number of things. But aroused was not one of them… and yet… Aroused is what she was. Her heart raced, not in anger or fear… but with a surge of lust.
The headmaster was old enough to be her father, and any sane or rational girl in her position would have marched out and called the police. But all at once she found herself in the grips of a sexuality that had been repressed for far too long.
Raised in the shadow of her parents puritanical belief system, which would see her reduced to little more than a baby making machine, with any thoughts of sexual expression, or god forbid sexual gratification, stripped away she was not prepared to be desired by a man who would have made her panties wet, had she been wearing any.
“Women like you, they need to be shown their place in the world, they need to be shown what they are capable of. This may be your punishment, but I think you will enjoy learning.” He said.
He ripped her bra down, exposing her breasts. She shuddered at his touch, he was the first man to have seen her chest since she was a child in her father’s arms, though he proved to be far less gentle than her father had been. The headmaster grabbed her breasts, shaking them as if testing their weight.
“You are a rather busty little slut aren’t you?” The headmaster mused as he played with her breasts.
“Sir…” Lilly started shyly.
“Speak up slut.” He barked sharply.
“Sir, I am not a slut…” She said.
“Oh? You aren’t huh?” He responded, amused.
“No sir, I have never even had sex before…” She said nervously.
“Well! A virgin! We will have to change that right away!” He said enthusiastically.
He took her firmly by the arm, ripping the remainder of her clothing off, leaving only her skirt around her waist. With one arm he pulled his enormous cock out of his pants, the mere size of it eliciting a gasp from Lilly who had never seen a cock before, at least not one outside of a computer screen. The headmaster guided her firmly to his desk and bent her over it, pressing her bare breasts into the cold surface. Lilly had only a moment to worry about what her first penetration would feel like before the headmaster’s cock forced its way between the lips of her vulva and took her virginity away forever.
Lilly had expected horrific pain, thanks to the myths her parents had filled her heads with about sex. Although there was a sharp flash of pain as her hymen was obliterated by the intruding flesh it was nothing close to what she had feared and what pain there was quickly found itself replaced by pleasure.
The headmaster had been blessed with length as well as girth, and the thick slab of flesh that he called his cock stretched apart her inexperienced cunt without hesitation.
“Oh fuck!” Lilly moaned as her cunt was forced to accept the rigid intruder.
While she had momentary thoughts of expressing how much she was enjoying herself she quickly found the words slipping away from her What might have been an eloquent expression of lust was instead replaced with besitial grunts, which while more simple were no less expressive in their own way.
The rhythmic thrusting of the older mans cock, each impact of their bodies brushing her nipples across the cold surface of his desk, started to have an effect on Lilly’s body beyond simple pleasure. She started to feel something tightening inside of her, as though there was a spring within that was being tightened with each and every thrust, until at last it released and something inside of her exploded. Her eyes lost their focus and she shuddered convulsively as the first true orgasm she had ever had washed over her.
She would later compare the experience of that moment to being swallowed in a sea made of fireworks, the waves of pleasure both washing over her and exploding around her in a way that could not be separated.
Although she was rendered momentarily senseless by the novelty of the experience the headmaster was entirely indifferent to her pleasure. He stripped her skirt from her and tossed it to the floor before lifting her bodily from his desk and positioning her on her back.
The momentary respite from the assault on her cunt allowed Lilly to regain some sense of where she was, however she was spared for only a moment, as her quickly pulled her hips upright and slammed is cock back into her sopping wet hole.
At this point Lilly was mostly along for the rise, focusing all her mental resources to keeping her hips positioned properly and her legs spread. The bounce and sway of her breasts as his cock slammed into her was hypnotically arousing and the headmaster found he could not pry his eyes away from her chest.
“Now, my little slut, I am very close to cumming. Because you have proven yourself to be a very good little fuck toy I will allow you an honor I don’t normally offer to my toys. I will let you pick if you would like me to pump your pretty little cunt for of my cum, or if you would like me to spray my load all over your perfect breasts. What will it be whore?” The headmaster said breathlessly.
Lilly struggled to form some sort of coherent response to his question as she sifted through the haze of lust and pleasure that coated her senses.
“Quickly my little toy, or I will choose for you.” He said when she did not answer quickly enough.
“My tits!” She moaned
The headmaster obliged her, ripping his cock from her ravaged hole. Obediently she sat forward, presenting her breasts to him.
“Here it come!” He moaned
He matched words to gesture a moment later as his cock sprayed cum across her young tits. Wave after wave of his hot white cum coated her enormous breasts, marking her in a way that while it could be cleaned up was entirely indelible in its own way. They both knew that this was the start of something, and they were both eager to find out where her path would lead.
Although she could leave his office, although she could choose to never see him again, she had started the path to discovering her sexuality, so long suppressed by her parents zeal. The door to her innocence was closed forever, and she found peace in knowing that she did not mourn for what was past, but looked towards her future.
Source: reddit.com/r/Erotica/comments/tmh4xt/lilly_meets_the_headmaster_part_03_mfbdsm