Lilly's Adventures

Lilly's Adventures

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


When Lilly, a young and innocently naive schoolgirl, accidently forgets to wear panties to school one day she ends up giving the whole class and eye full. This tragic wardrobe malfunction rockets her into the seedy underbelly of her school and exposes the dark and sexual activities of the staff, the students, and seemingly everyone she knows... Lilly starts to lose her innocence, and finds that she likes it better that way!


When Lilly, a young and innocently naive schoolgirl, accidently forgets to wear panties to school one day she ends up giving the whole class and eye full. This tragic wardrobe malfunction rockets her into the seedy underbelly of her school and exposes the dark and sexual activities of the staff, the students, and seemingly everyone she knows... Lilly starts to lose her innocence, and finds that she likes it better that way!

Chapter1 (v.1) - Lilly Meets the Headmaster

Author Chapter Note

Lilly meets the headmaster and discovers the dark and sexy underbelly of her expensive private school

Chapter Content - ver.1

Submitted: February 14, 2015

Reads: 11099

Comments: 3

A A A | A A A

Chapter Content - ver.1

Submitted: February 14, 2015



Lilly sighed as she opened her eyes. Although she did noticed that her alarm hadn't gone off she didn't give it much thought. Stumbling bleary eyed she navigated the minefield that made up her bedroom, barely avoiding knocking over a stack of CD's and some dirty laundry that she had stacked precariously the night before in an effort to clear her bed so she could go to sleep.


Climbing into the shower Lilly jumped a bit with a cry as the cold water hit her nubile body.


"Fuck!" she said, grumbling to herself about the fact that the water always took so long to warm up.


Rubbing herself with soap she closed her eyes, enjoying the feeling of the warm water cascading down her body. She started to explore her body, her hand sliding over her wet flesh. Switching to the hand held shower wand Lilly groaned loudly as the steaming water exploded into her pussy.


Although Lilly had been raised in a very sheltered home, a place where sexuality was rarely spoken of, and even then only with regards to how perverted and disgusting it was, Lilly had started to question her family's version of reality and explore her growing sexuality.


Lilly's eyes widened as her eyes found the clock that hung on the bathroom wall across from the shower.


"Oh no!" she cried as she realized that she was going to be late.


She rushed to find all of the pieces of her uniform, she knew it was already 10 past 8 and she should have been on her way to school more than a half hour ago. Her house had lost power the night before and instead of going off like it should have her alarm had simply blinked a sarcastic beat. Rushing around her room in a vain attempt to gather the pieces of her school uniform she rifled through the different drawers in her dresser. She realized, in a moment of panic, that she had forgotten to do laundry the night before, despite her mother's constant bitching, which meant that she was out of panties. The thought of wearing dirty panties filled her with a sense of revulsion, as she had always been a very clean individual.


“Crap.” she said frowning moodily to herself “I wonder if they would notice if I just went without for today?”


She contemplated just how revealing her skirt would be without her undergarments or a pair of pantyhose to protect her. She lamented the fact that whoever had designed her school uniforms must have been working off a costume design that would have been more at home in a cheap porno then in an expensive private high school.


"This uniform was probably designed by a perverted old man..." she grumbled to herself.


At just a few days past her 18th birthday Lilly was blessed with the casual good looks that forever denied her the friendship of so many of her female peers, matched with a healthy dose of innocence that stopped just short of impossibility. Standing at about 5'6", she had curves that broke hearts, and possibly several laws of physics. Long dark brown locks flowed down her back and cupped her heart shaped face like a gentle lovers embrace, framing flawless brown eyes so deep no heart could escape. Lilly was completely oblivious to the sensuous way she carried herself, as well as the disturbingly powerful effect it had on the men she interacted with on a daily basis, not all of which where students.


Deciding to forgo wearing panties that day she rushed to grab the mandatory uniform her school required for girls, stopping in front of the mirror  Lilly examined the uniform. Although her preferred style of dress might be best described as "trashy", as her preferred lounging wear was a semi see through white tank top and her lucky leopard print bra (panties/pants optional), her school uniform consisted of a tight fitting cotton blouse, which hugged her ample curves. The shirt was complemented by a short black tie, which was tied around her neck stopping just under her breasts, and a plaid skirt which fell to just below her knees was completed by knee high white socks and black shoes, trying to reassure herself that her lack of underwear was completely unnoticeable she quickly rushed down the stairs and out to her car.


Valley Catholic Prep School was one of the best high schools on the west coast. The school had been around for more than a hundred years, having been founded by the catholic settlers shortly after they had landed on the beaches of the Columbia. The campus was a huge and sprawling affair, covering almost three square miles. While the main building was a large imposing stone edifice, reminiscent of a Gothic castle, the staff were known for being much worse than the people who might have once inhabited such a structure in days gone by.

For an organization that was supposedly founded for the purpose of instructing the next generation on christian morality, Valley Catholic housed some rather tawdry secrets. Whatever it may have been in its early days, these days students and staff both enjoyed the more carnal side of life. Detention was almost as likely to involve being strapped to a desk for some "punishment" as it was to involve the more traditional writing of lines on a blackboard. While not all of the students (nor their parents for that matter) were aware of this aspect of their beloved school, those that were had been known to "act out" so as to earn a little punishment (though they tried very hard to pretend they despised it, no matter what the reality was...)


Chief among those that enjoyed the more base pleasures life has to offer was the headmaster. Although his resume was impeccable, he had earned his place in the hierarchy of the school as much for his ample genitalia, adept and inventive uses for a ruler and his skill with ropes as for his academic credentials.


The headmaster sat in his office leaning back in his high backed leather chair, from under his desk emanated a persistent sucking sound, and he sighed in pleasure. The female student on her knees under his desk had been sent to his office for “punishment” because she had been seen making out in one of the hallways. This was, quite ironically, completely unacceptable in a catholic school. Reaching down the headmaster cupped her tits and squeezed them roughly in one hand eliciting a squeal from the girl, using his other hand he grabbed a fist full of her hair and shoved her down harder forcing the full length of his cock into her mouth


“Take it all in you little slut.” said the headmaster


The girl wrapped her tongue around his long hard shaft trying hard to conceal the pleasure written all over her face, the headmaster laughed to himself. Grabbing the back of her head with both hands the headmaster started fucking her mouth thrusting up into her willing mouth roughly.


Getting excited the headmaster pulled her up onto his desk pushing the papers stacked there onto the ground to make room for her, reaching in between her legs he roughly pushed her panties out of the way, rubbing the head of his cock over her tight opening the headmaster lined up his cock over her opening before thrusting inside of her.


The girl moaned, the headmaster had a very large cock and he knew well how to use it. Taking no time for her enjoyment the headmaster quickly worked himself into a rhythm, pounding away at her tight pussy, feeling his balls start to tighten he grabbed her firmly to him mashing her sweaty mostly uncovered body against his he sunk his cock as far into her as he could go.


"Oh FUCK" he yelled, cumming deep inside her pussy. She moaned loudly as she felt his hot cum fill her.


“Now clean yourself up and get to class.” the headmaster said, whipping his cock off on her shirt as she buttoned it back up “and don’t forget you're on thin ice, break the rules one more time and the next punishment will be much worse. Do you understand?” he asked


“Yes headmaster.” she said looking at her feet, trying to hide her continued arousal. While she was frustrated that he had not taken time to get her off as well, she was already planning what she could do to get sent back before the end of the day.


The headmaster watched her leave sighing contentedly to himself before glancing over at the shelf where his camera was hidden. He always enjoyed a good fuck in the morning but his sex drive was so high he wouldn't be able to go all day with just one.


Stepping out in the hall he examined the line of students that awaited him outside his office. Several girls stood just outside his office in his private waiting room, two already had their panties pulled down exposing their tender flesh. He walked over and examined the two at the front of the line.


"You're next" he said gesturing to one of the girls.


She smiled excitedly, following him back into his office and closing the door behind her.


Valley Catholic school was one of the top private schools in the area and though it was large, having both a male and female student body, its class sizes where on the smaller side and its teachers were attentive to all of their students and quick with discipline. The teacher's attention and the first rate education provided to their students came at a price, and she knew it cost her parents a bundle to send her there, but its education system was the best in the area and she wanted to get the best education possible, she would do almost anything to stay enrolled there.Lilly glanced at her clock as she pulled into the last parking lot she realized she was already 15 min late for her first class. She growled in frustration, her teachers weren't known for their tolerance for disobedience she had only been at the school for a month and she didn't want to make a bad name for herself so early in her time there. Never a very well off family, her parents had sacrificed a lot to get her into that school, and they would kill her if she messed it up.


Lilly ran quickly down the hall to her first class, the complete absence of students and the chilling silence which permeated the halls all reinforced her sense of tardiness. Lilly approached the area where she knew her first period class was located, finding the door to her class, Lilly knocked before entering meekly. The teacher looked up and glared at the tardy student his irritation at being disturbed clearly written on his face.


“You're late Miss Anderson.” chided the teacher with an irritated grunt


“I know Mr. Jacobs, I’m sorry.” Lilly said casting her eyes down to the floor in submission


“Considering that you have been late three times in the last two weeks and that you are a new transfer to this school I would think you would be more interested in making a good impression?” Said Mr. Jacobs with a caustic tone in his voice Mr. Jacobs was known for his uncanny ability to lose his temper and his swift and deceive punishments, none of which made him overly popular with the student body, but made him a person to fear none the less.


“I know Mr. Jacobs; it won’t happen again I promise.” Said Lilly.


“See that it doesn't Miss Anderson but this is still a strike against you for today two more and you will be sent to see the headmaster, do I make myself clear?” Said Mr. Jacobs


“Yes sir.” Said Lilly.


“Then take your seat quickly.” Said Mr. Jacobs


Lilly rushed to the only chair left. However in her haste she dropped her binder, her papers and notebook hit the ground with a resounding thud. Lilly bent down to gather up her scattered supplies, oblivious to the show she was putting on for those around her.


“Is there a problem Miss Anderson?” asked Mr. Jacobs.


“No sir.” Said Lilly chiding herself on making a noise and further irritating the already volatile teacher.


The class resumed its normal routine with the teacher’s voice reaching his typical monotonous drone as he

proceeded to dive into his lecture. Try as she might Lilly could not keep her attention focused on the lecture it wasn't that she was a bad student but Ancient French Literature had never really been much of an interest of hers, she was only taking it because she had entered the school after the start of the term, of her late entrance had necessitated it since there had been no other more interesting classes open.


Lilly could feel the teacher’s voice drowning on and washing over her like a gentle wave and she could feel her eyes staring to get heavy. Vowing not to go to sleep, she valiantly struggled to maintain her alertness, but she was fighting a losing battle. Eventually capitulating, she shifted about in her chair, seeking for a more comfortable position. Lilly rested her head gently on her arms trusting in her secluded position in the back of the class to protect her from the teacher’s baleful gaze. Lilly relaxed and let her attention drift a bit as the sounds of the class washed over her shrouding her in a gentle haze, before she knew it her eyes had closed despite her efforts, and she relinquished her grasp on consciousness and drifted gently off to sleep.


Lilly dreamed, in her dream there was a young man from her class with her named Tom, she had had a crush on him since the first day she met him and in her dream he was confessing that he had always had a thing for her and professing his deep desire. Lilly had never had much more sexual activity then making out and maybe a little of what her parents referred to as “heavy petting”, a term incidentally she had never cared for since it made it sound like she was petting some kind of overweight animal. But in her dream she was a sexual beast, in the throes of her sexual desire they ripped and teared at each other, the thin cloth of their clothing serving as little obstruction to their desires. Shredding each others clothes they skipped foreplay, proceeding straight to fucking as hard and as fast as they could. She moaned quietly in her sleep picturing his rock hard cock pounding into her over and over again.


Although she had never been able to explore the darker side of her sexuality in her waking life, Lilly's dreams had no such restraints. Sexual domination was always something that had turned her on. Lilly's imagination placed her in a submissive role, Tom's powerful muscles restraining her, placing her under his control to be his sexual object.


The sudden silence snapped her out of sleep and she quickly looked around and realized that everyone was looking at her. The teacher hadn't remained quite as oblivious to her inattention as she had hoped he would, that fact that she had been moaning in her sleep probably hadn't really helped matters much.

“I’m sorry you feel my lecture isn't worth paying attention to Miss Anderson.” Said the Mr. Jacobs with a belligerent tone building up in his voice.


“I’m so sorry Mr. Jacobs I just didn't get much sleep last night and…” started Lilly in a vain attempt to make her excuse sound plausible.


“I am not interested Miss Anderson, you are really starting to try my patience you need to straighten up and

fly right!” Interpreted Mr. Jacobs, a flush creeping into his pale face and a vein in his temple starting to throb dangerously, “Now you will sit up and pay attention, one more strike and you will be in the Headmaster's office do I make myself clear?!” demanded Mr. Jacobs


“Crystal clear, Mr. Jacobs.” Said Lilly with a slight quiver in her voice, she didn't know what was wrong with her today it just seemed like one thing after another was going wrong first with the power going out and then with the laundry and now this it was like she was cursed or something.


The class slowly drifted back into its usual routine as the teacher calmed down and resumed his lecture.


Lilly started to squirm uncomfortably in her chair as the cold metal was uncomfortable her tender flesh, crossing her legs in an attempt to find a more comfortable position she noticed that Tom, one of the boys who sits next to her frequently was watching her closely. She had always had kind of a secret crush on Tom who was tall at a few inches over 6 feet and had the dark good looks that made her pulse quicken, she glanced down quickly her face flushing as she remembered the dream about him she had just had and she moved uncomfortably in her chair noticing that it was wet from her earlier arousal.


“I wonder why he is staring at me.” Lilly thought to herself, “Did I spill something on my shirt?” She wondered.


With a flash of insight she realized that by crossing her legs in her attempt to relieve her discomfort she has innocently given Tom a direct and unobstructed view of her crotch which due to her earlier carelessness with the laundry meant that he could see everything. Lilly could feel herself blushing furiously and quickly uncrossed her legs, though she had always had a crush on Tom and she had found herself having more sexual thoughts recently she was still innocent and no man had seen her unclothed since she was a child. Lowering her eyes to her desk she tried to keep her attention away from Tom, but her curiosity overcame her embarrassment and she peeked up at him. Their eyes met briefly and Tom flashed a big grin, glancing down below his desk she could see the outline of his cock pressed against the denim of his jeans.


Lilly could feel herself start to become aroused again at the sight of his erection and she could feel her pussy start to moisten as thoughts of his large hands on her tender flesh and his thick cock penetrating into her started to flood through her mind. Lilly smiled back shyly and returned her eyes to the front of the classroom.


A sudden chill ran down her spine when she noticed that Tom’s eyes were not the only ones which had noticed her innocent mistake but Mr. Jacob's eyes weren't friendly or lustful like Tom’s were, but were angry, irritated and full of indignation.


“Miss Anderson I would like to speak to you in the hall, now.” Said Mr. Jacobs a deceptively calm tone in his voice.


Lilly hung her head in shame before standing up and walking towards the door while the class scoffed and giggled to themselves though only Tom and Mr. Jacobs had noticed her momentary lapse in decency it looked like it her innocent mistake was going to cost her a great deal. Lilly walked out into the empty hall and heard Mr. Jacobs close the door behind them.


“You realize of course that panties are part of the dress code Miss Anderson?” said Mr. Jacobs with a belligerent tone in his voice


Lilly swallowed in fear and nodded meekly.


“Then would you care to explain to me why you have failed to cover yourself and have instead elected to walk around our school uncovered like a common slut in a porno movie?” asked Mr. Jacobs.


Lilly hung her head in shame and answered back quietly “I’m sorry Mr. Jacobs I forgot to do laundry last night and I didn't think anyone would notice.”


“Well notice we did Miss Anderson, this is a serious breach in school policy, I have no choice but to send you to the head master, you will be lucky if you are still a student here at the end of the day.” Said Mr. Jacobs with a sneer. “Go straight there, his office will be informed to expect you so don't even think about trying to evade this.” said Mr. Jacobs


“Yes sir.” Said Lilly mournfully.


Lilly walked down the long, empty hallways of the school, each step felt like one closer to the end. She had a sudden revolution about the way it must feel to be lead to your own execution. She knew that her parents would have a fit if she was kicked out of school especially for something as embracing as forgetting to wear panties.


Lilly approached the large oak door and ran her hand lightly over the embossed brass plate which read “Headmasters Office” trying to stall for time, any time, to keep her away from her inevitable fate. Taking a deep breath Lilly braced herself and opened the door and entered the office. The secretary looked up as she entered


“Miss Anderson?” She inquired.


Lilly nodded quietly.


“The headmaster is in a meeting right now in another part of the school, you are to enter his office and sit in the chair in front of his desk and wait quietly for him to return.” the secretary informed her.


“OK.” Lilly said.


Lilly entered the office and moved to the high backed hard wooden chair sitting in front of the desk. The door to the office closed with a sense of finality to it that did not bode will conjuring images of jail cells and bear traps. Lilly looked around herself at the richly appointed office, the walls where the deep brown of polished wood panels and pictures of former headmasters were hung on the walls around her, in front of her was a large wooden desk with a nameplate on it which read: “Head Master Alexander Fulton”. Continuing her inspection of the office she noticed hanging on the wall behind the desk was a long wooden riding crop.


“He has a lot of wood.” Lilly thought wryly to herself


Her musings were interrupted by the sound of the door opening behind her. The headmaster entered the room and they stopped to apprise each other, unlike so many academics his belly was flat and his arms were powerful and well built, his hair was mostly brown but there was a bit of gray in it,, his eyes had a fire in them that was belied by his deep and calming voice.


Lilly could feel herself flush below the waist and tried quickly to suppress those feelings since this was neither the time nor the place for them.


“Miss Anderson?” The headmaster inquired raising his left eyebrow slightly.


“Yes.” Lilly nodded back


“I have been informed that you have been causing disruptions in class today and that you have decided to flaunt your body in a way which is highly inappropriate in a religious school.” The Headmaster said.

Lilly covered her face in despair and nodded quietly.


“You realize of course that we have no choice but to expel you in a situation like this.” Said the Headmaster quietly


Lilly’s eyes shot up to find the steel gray eyes of the head master


“Please Sir, My parents had to move away from my home town and have sacrificed a great deal to enable me to attend this school, I can be expelled!” Lilly pleaded


“I really am sorry Miss Anderson but the school's bylaws are explicit in a situation like this my hands are tied.” Said the Headmaster


“Isn't there something that you can do?” whined Lilly, “Ill do anything to stay”


“Anything?” Asked the headmaster quietly


“Yes! I can’t let my parents find out about this” Lilly said missing the implications of the headmaster question


“Well maybe we can work something out.” said the Headmaster, “You realize of course that you will have to be punished? We can’t have you thinking that kind of behavior is alright.”


“Of course Sir.” Lilly said gratefully

“All right Miss Anderson, come here and strip.” Said the Headmaster a slight smirk on his face and a lustful look in his eyes. Had Lilly had more experience with men his look would have chilled her to her bones. Lilly walked over behind the headmaster's desk and stood next to him uncertainly


"Sir?" she said, not being sure of what she had just heard.


"I want you to take off what clothes you decided to wear to my school today" he said

Lilly uncertainty began to remove her clothing.


“Reach behind my desk and pick up that wooden riding crop off the wall.” The head master commanded her

Lilly obeyed and took the thick wooden implement, her hands shaking slightly as she handed it to the head master.


“Now kneel, I’m going to punish you the way we have punished disobedient children for years.” Said the Headmaster


Lilly obediently dropped to her knees before the headmasters high backed leather chair unsure of quite what position she he desired her to be in.


“Like this Sir?” She asked hesitantly her voice quivering with uncertainty.


“No! you need to be close enough to spank, my arms aren't a mile long!” Said the Headmaster


Lilly moved closer and positioned herself over his lap, the head master grabbed her by her ponytail and pulled her down, she could feel her breasts pushing firmly against his crotch as he pulled her tightly against him, he proceeded to pull her skirt up exposing her lush posterior.


“Are you ready to begin Miss Anderson?” asked the Headmaster


“Please sir isn't there any other way?” asked Lilly “I haven't been spanked since I was a child this is so embracing” she complained


“Would you rather be expelled?” Asked the Headmaster


“No…” Lilly said mournfully


“Then let’s begin.” Said the Headmaster gleefully “I know you aren't going to enjoy this but I know that I will.”


Lilly cried out as the thick wooden shaft bit painfully into her ass, again and again with thunderous force the riding crop punished Lilly ass. Each stroke of the crop cause Lilly whole body to move back and forth her large breasts straining against the tight material  the Headmaster concealed cock. After ten strokes she could feel his cock start to harden straining against her breasts. Lilly cried out in pain after each stroke of the crop feeling the pain growing she tried to bite back her tears as she hoped her punishment would end quickly.


“You complain too much.” said the Headmaster “I think we need to quiet you down.”


Untying the black tie from the front of her uniform the head master shoved part of it into her mouth tying it tightly behind her head creating a crude gag


“There that’s much better.” said the Headmaster looking down at her while she endured her punishment helplessly


“I think that’s enough of the crop for now, you a pretty red, but your punishment isn't over. I may be a bit soft on student punishment but I don’t want you to think you're getting off easy with only a few slaps on the behind.” stated the Headmaster


Lilly whimpered mournfully but nodded her head in understanding, the headmaster continued to spank Lilly his large muscular hands striking her backside firmly, each stroke became a little softer than the last until it was more of a stroking motion then a spanking one. Lilly could feel the headmaster's enormous cock pressing through the thin material of her top, rubbing against her breasts, the stimulation was starting to excite her but she was worried about what he was going to do next. Throughout her punishment she could feel herself starting to become aroused and before long her pussy was becoming very moist despite her best efforts to resist it. The head master hand continued to stroke her ass drifting slowly down to the place where her legs met and the back of her bare pussy poked out slightly exposed due to both her lack of panties and the bent over position she had been forced into. Lilly’s own moisture began to drip down her leg and the headmaster noticed that she was becoming aroused by her punishment.


“So this turns you on does it?!” He shouted anger building in his voice as his hand brushed the back of her pussy feeling the moisture of her arousal on his fingers


“No Sir!” Lilly answered fearfully not wanting to get into any more trouble because of her body’s reaction to some deviant sexual stimulation


“Don’t lie to me you little slut I can feel you getting wet!” The Headmaster said running his index finger over her slit, gathering a little of her moisture before holding it under her nose as proof of her dishonesty


“I’m sorry sir.” Lilly responded


“Lying is a serious offence at this school and if you are going to act like a slut then I am going to treat you like one!” Said the Headmaster moving his hands toward her exposed body


“Please Sir no!” Lilly pleaded fearful of setting him off further, but she had never been sexual with a man before and this wasn't really how she had pictured the advent of her sexual experience


The headmaster's hand drifted down between Lilly legs and started to rub the back of her pussy from in-between her legs roughly. Lilly moaned and her back arched slightly despite her efforts to contain herself she had not expected that his fingers would feel so good. Her pleasure induced contortions caused her breasts to push harder against the headmaster crotch. The headmasters finger traced her slit gently from behind before thrusting his index and middle finger deep inside her virgin pussy.


“Ahh!!” Lilly cried out


Slapping her ass firmly the head master said “let me make myself clear, this is a punishment you are not permitted to cum without asking permission first do you understand?”


Lilly bit her lip and nodded


“Good.” Said the Headmaster “If you disobey your ass will be punished even worse.”


Lilly nodded in understanding


The headmaster inserted his finger back inside her tight pussy slowly, working his way from the tips of his finger to all the way up to his knuckles and then pulling back out and doing it again. Each time he went just a little bit faster and a little bit harder until he was pumping in and out of her tight hole. Lilly could feel the head masters fingers reaching deep inside of her and violating her virgin pussy, at each thrust she could feel his fingers curl just a bit inside of her hitting something deep inside making her back arch and pressing her breasts ever harder against his steel concealed cock. Lilly could feel something building inside her that she had never felt before, each thrust of his thick fingers inside her brought it closer to the surface.


“Oh god what’s happening?!” Lilly cried out her back arching and her fingers biting into his leg.


“Never had an orgasm before?” Asked the Headmaster gleefully


“No.” Lilly said her voice quivering in pleasure “I have never done anything sexual before.”


“Well then I am happy to introduce you to woman hood.” said the headmaster brutally


Continuing his merciless assault on her tight pussy, his fingers thrusting deep and hard inside her pussy, over and over again he pounded his fingers inside of her and from the contractions of her pussy he knew she was going to cum soon and he intended to punish her for it, she wasn’t the only one who needed to cum


“Please sir, can I cum?” Lilly begged


“No! Don’t you dare you dirty little slut!” said the Headmaster


Lilly could feel it building each time his fingers thrust inside of her


“Please?” she begged “I don’t know how much longer I will be able to hold it in.”


“You had better or you will regret it.” Said the Headmaster


“OHH GOD!” Lilly screamed the headmaster’s fingers penetrating her virgin hole one to many times, her first orgasm blasted through her buckling her legs and making her whole body go limp. The headmaster could feel the muscles of her pussy clamping down on his intruding fingers and smiled to himself, it was time he had some fun to, he planned on enjoying her punishment.


“I thought I told you not to cum?” Asked the Headmaster


“I’m sorry sir.” responded Lilly “I couldn’t help it.”


“You're not sorry yet, but you're about to be.” Said the Headmaster “Now get off me and get on your knees, since you insist on being a slut and cumming during your punishment you are going to have to learn how to suck cock.” The headmaster unzipped his pants and pulled out his cock, Lilly eyes widened at the sight, it was more than a foot long and looked to be thicker than both of his fingers but together and it wasn’t even fully erect yet.


“Come here slut.” said the Headmaster


Lilly approached him uncertain of what to do.


“Get down here.” said the Headmaster grabbing Lilly’s ponytail and pulling her onto her knees in front of him


“I am going to show you how to suck cock like a slut should.” said the Headmaster “Take your left hand and gently cup my balls.” He said “Then take your right hand and position it at the base of my cock, take your mouth and put it all the way in up to your hand, then make bobbing motion up and down with your head following your mouth up and down with your hand each time.”


After describing this he grabbed Lilly’s head and shoved his cock into her mouth while she was still in the process of absorbing what he said. Lilly was surprised and a little shocked and so was slow to respond to the unexpected intruder in her mouth, sensing her uncertainty the Head Master gripped her hair and shoved his cock all the way down her throat causing her to gag and choke on it.


“If you don’t like that then do it the way I told you to!” Said the Headmaster


Lilly was quick to comply with his demand this time wrapping her tongue around his slowly hardening shaft she began to make quick bobbing motions up and down taking his cock as deep into her throat as she could and cupping his balls gently in her hand. Lilly could feel his cock getting harder in her mouth and quickly she found that she couldn't fit it all in her mouth. Noticing that she was starting to gag the Headmaster stopped her and pulled her up “Its time for the next part of your punishment” he said wickedly


“Please, haven’t I done enough yet?” Lilly pleaded


“No you have something that I want.” Said the Headmaster


“What?” Lilly asked confused


“Your virginity!” laughed the Headmaster


Before she could respond the headmaster pulled her upright and quickly positioned her above his rock hard cock, nudging her legs out from under her she stumbled and collapsed into his lab.  Lilly collapsed into the head master lap and felt the penetration of his enormous cock, she felt it slide up inside of her all at once penetrating much deeper than his fingers ever could. She didn't know how she could fit all of it inside her tight virgin hole but she could feel her tight pussy stretch to accept his huge thick cock. Lilly moaned in pleasure as she felt it violate the deepest recesses of her pussy


“Oh no! What have you done?” Lilly moaned


“I have made you mine now, you belong to me!” grunted the Headmaster


His huge hands slid up under her shirt and grasped her tits tightly.


Pulling her backwards against him he lowered his head and gently traced circles around her left nipple with his tongue. Each circle he made was smaller and smaller before he finally reached her nipple and sucked it hungrily into his mouth. One hand reached up and firmly clasped her other tit squeezing it roughly while his other hand drifted down her waist and between her legs making a small trace of what was left of her slit that wasn't being impaled by his enormous cock before finding her clit and rubbing it gently. Lilly moaned loudly and squirmed on his cock enjoying the motions of his hand and mouth and the feeling of having his enormous cock inside of you.


Finishing with her tits and clit the headmaster placed his large muscular hands on either side of her hips and started to lift her up and down on his cock each time thrusting harder and harder until he could feel each thrust hit the back of her pussy. Lilly started moaning loudly and bucking her hips to each of his downward thrusts until she didn't need his hands at all anymore, primal instinct took over and she started riding his cock like a hardened pro, sliding up all the way to the tip before slamming back down on his cock she tossed her hair around and reached up to grasp her tits and pull one into her mouth and sucked greedily on her nipple enjoying the feel. Lilly screamed out in pleasure as the headmaster's hand found her clit again.


Lilly kept working harder and harder riding up and down on his huge thick cock feeling it penetrate deep inside her and fill up every part of her tight pussy. She could feel another orgasm start to build deep inside her and she picked up her pace driving his cock harder inside of her losing herself in the feeling of being fucked. Finally her orgasm hit her and she moaned out loud collapsing on top of his still rock hard cock laying against his chest and breathing heavily.


“That’s twice you have cum without permission!” Said the Headmaster


“What?” Asked Lilly still a bit dazed and confused from her last orgasm


“I can see I am not punishing you enough I will have to go further.” stated the Head Master


Lilly felt herself being pushed to the floor and landed on her hands and knees, the head master reached down and positioned the head of his enormous cock directly behind her, placing both hands on her hips he pulled her back while thrusting into her.


“Now I’m going to fuck you like a dog.” Said the Headmaster


He started to fuck her harder and harder before deciding that she wasn't doing enough on her own he decided to motivate her by grabbing on to her ponytail and pulling it towards him to encourage her to thrust harder. Lilly worked as hard as she could bucking her hips and grinding her pussy against his cock, thrusting in and out over and over as she moaned.


“Please?” Lilly begged “Fuck me harder?”


“Oh? You like being fucked like a slut?” Asked the Headmaster


“Yes…” said Lilly


“Then say it” commanded the Head Master


“I like being fucked like a slut…” Lilly said


“And whose slut are you?” He asked


“Yours.” she moaned


You're fucking right you are!” He added


Picking up the pace he started fucking her as hard as he could until is was lifting her off the ground to meet his cock each time he thrust, he could feel the muscles in her pussy starting to contract and knew she was about to have another orgasm so he continued to plow her enjoying the sound of her moaning and the tight slick feeling of her formerly virgin pussy gripping his big thick cock, he could feel his balls tightening and knew that his own orgasm was starting to build, he quickly pulled out and lay down on his side before pulling her down next to him.


He pulled her sweaty naked body against him and forced her legs apart with his hand before roughly rubbing her clit and shoving his cock back inside her hot slick pussy. He resumed fucking her, pulling her body tightly against him he reached out and grasped her tits and used them as hand holds to fuck her even harder he finally was fucking her so hard he flipped her over onto her chest and pinned her down with his body weight, one hand reach down between her legs while he continued to fuck her mercilessly from on top one hand on her clit and one on her tit cruelly pinching her nipple between his thumb and forefinger. Lilly moaned in pleasure as she felt him pounding her but then she felt his cock start to twitch inside of her, she realized that he was going to cum soon and struggled to get him out of her, but she was pinned down by his body weight and as he quickened his pace in preparation for his orgasm her struggles diminished as she felt her own orgasm approach.


“Where are you going to cum?” Lilly moaned out


“Inside of you.” He grunted feeling his orgasm approach


“No! Please no?” Lilly pleaded “Can't you cum on my tits or something?”


“As you wish, but ladies get to have men cum on their tits but sluts get their face covered in cum!” He said

He pulled his cock out of her, eliciting a protesting cry. Pulling her into a sitting position she opened her mouth expectantly. Wave after wave of cum greeted her eager face.


They lay there on the floor both sweaty with the smell of cum in the air, he pulled his cock out of her pussy and she felt their cum dribble down her leg, she looked down in shame and saw the thick white liquid coming out of her.


“Now your last job for today is to clean my cock.” He said


Lily obediently moved down and proceeded to lick her own cum off of his cock and despite her shame at losing her virginity in such a way she felt good and she even found she liked the taste of their mixed cum, she felt her pussy start to get wet again as she cleaned her own cum up. The headmaster stood up and moved over to a closet and took out a new uniform and handed it to her.


“Put these on.” He commanded “And don’t forget your mine now, I will be calling you to my office from time to time when I feel like using you.”


“How do you know I won’t report you for this?” Lilly ask defiantly


“Look over there.” Said the Headmaster pointing to a potted plant sitting on a shelf


“What?” asked Lilly confused “I don't see anything?”


“What you don’t see.” said the Headmaster “Is a camera which has been recording this entire incident if you report me I may lose my job but I will post that movie on the internet and everyone you know will see it, do I make myself clear?”


“Yes sir.” said Lilly hanging her head in defeat


“Now get back to class, I’m sure we'll be seeing each other soon.” said the Headmaster “and don't worry you aren't being expelled I think you have learned your lesson.”

The rest of the day sped by the classes moving past in a blur, Lilly could already feel the pain starting to build in her pussy from the pounding the headmaster had given her earlier, and her ass was raw from her spanking. But more than the pain Lilly’s mind kept returning to the headmaster's office, of her legs being spread by his powerful hands and his thick cock thrusting into her over and over again.


The day finally ended with Lilly hobbling out to her car trying to ignore the sharp pain that had resulted from her visit to the headmaster's office. Although she had not had a chance to check herself since the morning she was sure that the headmasters attentions had left their mark on her tender flesh. She was slightly surprised to find that the pain from her marks burned in a way that was not unpleasant.


"maybe I am kinkier than I thought..." she said to herself. She had heard that everyone has a kink if they look hard enough. She supposed that the headmaster had helped her find hers.


On her way home Lilly noticed a sex store she hadn't seen before. Despite the pain and the humiliation that she had suffered at the hands of the headmaster she had enjoyed the feeling of her orgasms and she wanted more experience with it. On a whim she pulled into the parking lot. The inside of the sex store was dark and cramped and Lilly felt a little dirty being in there. Looking at the row after row of sex toys she wasn't sure which one she wanted to buy there were so many choices.


“Hmmm… I can’t wait until tomorrow so I can try this out…” she thought to herself.

© Copyright 2019 Luke Ashwood. All rights reserved.


Add Your Comments:








Other Content by Luke Ashwood

More Great Reading

Popular Tags