Lilly Ch. 01

Chapter 1

Lilly Meets the Head Master

Lilly 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 a half hour ago but her house had lost power last night and her alarm hadn't gone off the way it was supposed to. Sorting through the different drawers in her dresser she realized that she had forgotten to do laundry the night before, despite her mothers constant bitching, which meant that she was out of panties and had nothing wear that day.

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

At just a few days her 18th birthday Lilly was a stunningly beautiful girl, standing at about 5 foot and 6 inches she had curves that made many of the guys at her school, not to mention guys on the street, turn their heads and drool as she walked by, long dark brown hair cupped her heart shaped face like a lovers embrace and flowed down to just below her shoulders deep brown eyes so dark they were almost black at time peeked up from a sea of flawless skin that was a deep tan that only came from many hours under the sun. But despite her stunningly good looks Lilly was completely oblivious to the sensuous way her carried as well as the disturbingly powerful effect it had on the men she was around on a daily basis, which unluckily for her where not all 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, a tight fighting white cotton blouse hugged her ample curves and the paleness of the cloth served to emphasizes her tanned skin, a short black tie was tied around her neck which stopped just under her breasts, 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 and the school had been around for more then a hundred years having been founded by the catholic settlers shortly after they had landed on the beaches of Virginia. The campus was huge and sprawling covering almost three square miles, the main building was a large imposing stone edifice reminiscent of a Gothic castle and the staff weren't know for being much better then the people who might inhabit such a structure had it really been in medieval Europe. The head master 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 hall ways which was completely unacceptable in a catholic school. The girl had long blonde hair which stopped in between her shoulder blades, and had large full breasts at least a D cup but without the sagging which was so common in breasts that size, he could see the top of a tattoo on her back but it was mostly obscured by her shit. Reaching down the head master cupped her tits and squeezed them roughly in one hand eliciting a squeal from the girl, using his other hand her 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 head master

The girl wrapped her tongue around his long hard shaft trying hard to conceal the distaste written all over her face, the head master laughed to himself, he knew she was a lesbian and only liked girls so forcing her to suck his cock was very satisfying. Grabbing the back of her head with both hands the head master started fucking her mouth thrusting up into her unwilling mouth roughly. Getting excited the head master 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 head master lined up his cock over her opening before thrusting inside of her. The girl moaned despite her extreme dislike of what was happening, no matter how hard she tried not to enjoy it the head master had a very large cock and he knew well how to use it. Taking no time for her enjoyment the head master 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 cumming deep inside her pussy making her moan in a combination of disgust and pleasure.

"Now clean yourself up and get to class." said the head master 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 head master." she said looking at her feet in shame and disgust

The head master 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

"I hope someone else gets in trouble today." he said to himself chuckling under his breath

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, her parents had sacrificed a lot to get her into that school and they would kill her if she messed it up. 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 teacher were attentive to all of their students and quick with discipline, but the teachers 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 ran quickly down the hall to her first class, the complete absence of students and the chilling silence which permeated the halls all re-enforced 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.

"Your 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 head master, 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, which was located in the back left corner of the small classroom. She sat down quickly and let out a small gasp as her bare flesh came into contact with the unexpectedly cold metal of the chair, she had forgotten that she had neglected to wear panties that day she could feel the cold metal of the chair pressing against the tended flesh of her exposed pussy.

"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 loosing battle, eventually capitulating to her 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 indecently she had never cared for since it made it sound like she was petting some kind of over weight animal but in her dream she was a sexual beast and they ripped of each others clothes skipping foreplay and 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.

The sudden silence snapped her out of sleep and she quickly looked around and realized that everyone was looking at her and she realized that the teacher hadn't remained oblivious to her inattention like 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 in your excuses 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 Head Masters 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 over came her embracement 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 class room.

A sudden chill ran down her spine when she noticed that Tom's eyes where not the only ones which had noticed her innocent mistake but where Mr. Jacobs eyes weren't friendly or lustful like Tom's were but where angry and 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 stood up and walked 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, dissertated 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 "Office of the Head Master" 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 enquired.

Lilly nodded quietly.

"The head master 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 head masters where hung on the walls around her, in front of her was a large wooden desk with a name plate 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 where interrupted by the sound of the door opening behind her. The head master entered the room and they stopped to apprise each other, he was an older man probably in his mid fifties, unlike so many academics his belly was flat and his arms where powerful and well built, his hair was mostly gray but there was enough black left in it to hint at what it must have looked like in his youth, a rugged beard graced his jaw and like his hair it had turned from the solid black of youth to the salt and pepper look of experience, 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 head master enquired, raising his left eye brow 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 Head Master said.

Lilly cast her eyes downward 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 Head Master 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 schools bi-laws are explicit in a situation like this my hands are tied." Said the Head Master

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

"Anything?" Asked the head master quietly

"Yes! I can't let my parents find out about this" Lilly said missing the implications of the head master question

"Well maybe we can work something out." said the Head Master, "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." Said the Head Master a slight smirk on his face and a lustful look in his eyes. Had Lilly had more experience with men would have chilled her to her bones. Lilly walked over behind the head masters desk and stood next to him uncertainly

"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 across my lap, I'm going to punish you the way we have punished disobedient children for years." Said the Head Master

Lilly obediently kneeled before the head masters high backed leather chair unsure of quite what position she he desired her to be in.