Lilly Meets the Headmaster

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 mine filed 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 black board. 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 had 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 head master laughed to himself. Grabbing the back of her head with both hands the head master started fucking her mouth thrusting up into her willing 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 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.

In Class

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 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 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 n 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. Jacobs 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.

In the Headmasters Office

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 schools bylaws are explicit in a situation like this my hands are tied.” Said the Headmaster

“Isn’t there anything 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 Head Master

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 head master 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. Through out 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 headmasters 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 head masters 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 Head Master 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 Head Master

Before she could respond the head master 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 except is 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 Head Master

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 headmasters 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 loosing herself in the feeling of being fucked. Finely 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 pony tail 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

“Your 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 will 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 head master 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 helper 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.

Lilly Meets the Headmaster

CO Geekery

Good Afternoon Readers

I wanted to announce that the etsy store for the company which owns/operates this website is now live. Check out some of the stuff they are selling below and check out the store!

 

 

Devil’s Trap Plate

 

 

 

 

 

 

 

Keep your demonic food trapped with this devils trap reusable and dishwasher safe plate. No smoking out for that demonic chicken and your evil potato salad will be rendered powerless by this laser cut devils trap plate inspired by the show Supernatural and the Key of Solomon.

Devils Trap – The devils trap is based of designs in the Lesser Key of Solomon and is one of the patterns used in the hit show Supernatural in order to keep demons trapped and powerless within its confines, and now you can keep your food trapped too.

Plate is also BPA Free.

Plate is the bright red color seen in the first picture. Second picture had a clearer shot of the laser cut but is more orange looking than the plate actually is so beware.

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Aperture Science Plate in Red/Blue/White

 

 

 

 

 

 

 

 

This is a triumph! I am making a note here: HUGE SUCCESS

Now that success can be yours as well with this Aperture Science plate. A plastic dishwasher and microwave safe plate that has been laser cut with the Aperture science logo from the hit video game Portal.

BPA Free/Dishwasher Safe/Microwave Safe

Aperture Science is known far and wide for their potato powered robots, auto-firing child friendly turrets and perhaps a little less well known for their ground breaking portal gun. Now you can use the type of plate that they might have used in their cafe’s and cafeterias. This plastic plate is proudly emblazoned with the Aperture Science Logo. Just make sure you don’t have two or your food might disappear…

8.5″ Diameter

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Legend of Zelda Beer Stein

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

You will be proud to display this Legend of Zelda beer stein!

Laser cut with the Hylian Royal Family Crest this beer stein is made of heavy glass and is microwave and dishwasher safe. Show your love for the Legend of Zelda and the Royal Family with this stein.

CO Geekery

The Cam Whore

She knew that her followers would enjoy the show today, she was desperate to earn some money, her rent was do and just taking her clothes off on camera wasn’t enough anymore. She had been losing followers for a few weeks now.

She headed for the back corner of the public library, the part that housed the technical manuals that nobody ever really looked at. Luckily the library was pretty empty today, she knew if she got caught she would be in a lot of trouble, but the risk was part of what turned the followers on. She set up her laptop and put her username and password into the login screen. She had been hyping her followers up for today’s show for the last few weeks. As she signed into the chat program she could see that there were several dozen of her followers logged in already. She positioned the camera so that her torso and legs were visible and started streaming.

She pulled the top of her dress down to expose her pert young breasts and revealed the fact that she was not wearing a bra. She was well enough endowed to gain most men’s interest but now so well endowed that her breasts had started to sag yet. She was flush in the prime of her youth. Her nipples immediately hardened in the chill air conditioned library. She pulled up the bottom of her dress to reveal that she was not wearing any panties either. She was already wet with anticipation of the upcoming show and she could feel the moisture from her pussy seeping down onto the hard wooden chair that she was sitting on. Several dozen more followers started to sign on as word spread that her show had started. She saw that several of them had made paypal donations, but not enough for her to be done yet.

She reached into the backpack that she had brought with her and pulled out a flesh colored dildo with a suction cup attached to one end. Attaching it firmly to the chair that she was sitting on she lifted her hips just enough to take the tip of the dildo inside her already sopping wet pussy before sliding down the length of its synthetic shaft. She groaned quietly as it penetrated her pussy, spearing into her tender flesh. She started to rock back and forth, grinding against the chair. She adjusted the camera to make sure that both her exposed breasts and what was visible of the dildo were in the camera’s frame as she rocked back and forth.

Her first orgasm happened quickly, her body rocking and quivering as her pussy exploded in pleasure. She did what she could to muffle her cries, worried that she might attract someone’s attention despite the relatively abandoned nature of the library.

People continued to sign into her chat program and she noticed that a few more donations had been made. She started to find herself even more aroused, the thought of all of those strangers watching her get off in the public library spurred her on. She continued to grind on the chair, one hand cupping her breast, playing with the swollen nipple while her other hand drifted lower. She found her clit with one hand and started to play with herself. The stimulation from both the dildo and her hands quickly spurred her into her second orgasm. She noticed that she had squirted when she had cum, the colorless liquid pooling on the chair beneath her. She had only been able to squirt a few times in her life, when she was most aroused, and realized that perhaps being in public was turning her on more than she had thought that it would.

She quickened her pace, her hips rocking furiously against the chair, her pussy making a wet smacking sound as she slammed her hips against the hard wooden chair, desperate to have the synthetic flesh violate her pussy. Her body rocked and shook as her third orgasm exploded within her. Try as she might a passionate cry escaped her lips, filling the quiet library with the sounds of her pleasure. She bit her lip frightfully when she realized how loud she had been and looked around. Fortunately it appeared that no one had responded to her cries, or perhaps the rows of books had muffled her sounds. She thought she saw someone duck back behind one of the rows out of sight when she turned around, but she realized that as paranoid as she was it could easily all be in her head as well. She continued with her show, rocking and contorting her body, as though dancing to music that only she could hear. She took a break at one point to respond to some of the comments from her followers, and to take some requests. Some simply involved her playing with her pussy some more, something she was both willing and eager to do, and some were a bit more depraved (one particular follower offered her an obscene amount of money if she would shove a book up her ass, something she was not sure was actually physically possible)

Nearing the end of her show she decided to change positions and give her followers a view of her semi famous ass, something she was quite proud of. She lifted her hips, sighing as the tip of the dildo left her pussy’s embrace, before turning around and sliding it back inside of her. She thrilled at the feeling of the massive plastic cock stretching out her insides. She lifted and dropped on the hard wooden chair, making a dangerous amount of noise as her bare ass slapped against the chair. She shook again as her final orgasm exploded inside of her, adding more of the colorless fluid to the chair beneath her. She shook and convulsed, her legs going weak momentarily. She was grateful for the chair beneath her as she would likely have otherwise fallen on her ass when her legs gave out. She looked up just in time to see someone duck into another aisle as she looked around. She was nervous at first, before realizing that if it was someone who wanted to get her in trouble they likely would not be hiding now. She thrilled a little at the thought of a naughty voyeur watching her perform for her fans.

She checked the chat program and realized that she had hit the limit she needed to pay her rent about halfway through the show, she even had enough to buy some new underwear or maybe some new toys to show off later.

It was good to be a cam whore.

The Cam Whore

School Teacher

My teacher and I had a strict relationship in school; at times I thought that he disliked me because of how hard he was with me and my work. But because he taught my favorite subject I couldn’t afford to fail. So after school last Wednesday, I asked him if he could tutor me. Going over the skits and work that we would receive in the near future. He actually smiled at me and gave me the ‘up and down’ look.

I was wearing a shorter skirt than normal because of the heat and the mandatory white button down shirt but he seemed to take more notice in my legs and thighs. Mr. R turned his chair towards me and told me to sit on his desk. Not thinking much of it I leaned my backpack against the side and slid my way onto the desk. He placed his hand on my inner thigh…

“I only have time right now this week” his eyes failed to pull away from where his fingers resided. I breathed in. Hard. “I have time; I need this” I replied looking at him as he glanced up at me. “What can you teach me?” He stood and leaned into me, his breath gracing my lips. “Faust” He replied, his hand moving up my thigh. Tracing his fingers along the crease of my ‘V’. “The main character’s goal is to seduce a woman with words… and with touch” plunging his fingers into my underwear he began to rub at my clit.

Gasping I gripped into the papers on the desk. How should I react? Push him away? but it felt so good… instead I spread my legs a little more as he entered three fingers into me. Mr. R leaned in then kissing me lightly. Then pushes my lips apart with his tongue. Wrapping my arms around his neck we engross ourselves in this passionate kiss. The heat surging within his dick against my leg. We pull apart and he begins push himself against my slit. “… teach me” I whimpered in his ear almost embarrassed by what escaped my lips.

With this invitation he pulls on his belt and drops his pants with little effort needed. He then reached his hand back up my skirt and pulled down hard on my panties until I heard a rip as my lacey thong snapped. I looked down at him and had the urge to touch his cock. When my fingers touched Mr. R’s tip he gave out light “nhgh…” smiling I then got on my knees. Licking his dick with my tongue and rubbing my hand along his shaft. I then took his whole manhood in my mouth sucking hard and humming. At the vibration of my mouth his cock gave a jolt. I could feel the heat in my mouth as some cum came out but not a full ejaculation. It was far too early for that. His hands in my hair I let go of his cock still hard.”Don’t stop” he moaned and looked at me. lifting an eyebrow I replied. “Pleasure me teacher” With that I laid back against the floor; tracing my fingers up my shirt unbuttoning to reveal my bra. I then moved my hand down to my clit and started to masturbate in front of him.

It didn’t take him long to join me by spreading my legs and plunging himself into me. I could feel the slow entry and then the entire dick as my body clenched against him. Gripping into his back he fucked me hard on the linoleum floor behind his desk. He lifter me up and me proceeded into reverse cowgirl. He cupped each of my breasts as I thrust up and down against his cock. I began to moan a little too loudly. He shot one of his hands into my mouth as we climaxed, screaming into his hand as I felt his cum drip out the sides past his dick.

He didn’t pull out for a little bit but instead held into me, I wanted more but couldn’t find the right words. He pulled out and licked me clean as I promised to do the same to him. He kissed me lightly.

“Same time next week” He smiled “Only if you fuck me again”

Originally on NSFW Stories

School Teacher

The Site is Live Again

Good Evening

Apologies to anyone who tried to access the site during that brief downtime, the site is now live again and the transfer to the new company has gone smoothly. Check out the site and enjoy the erotica!

www.mypervertedstories.com

The Site is Live Again

Website Trouble

Good Afternoon Everyone

I wanted to let you know that there may be some troubles with the website in the next few days. Bluehost, the company that hosts my website servers does not allow adult material so I will be switcing and this take some work, please endure this with me and have faith that I will be back shortly.

Thank You.

Website Trouble

Tentacles

“No rest for the weary.” she said quietly Alexis sighed and rubbed the bridge of her nose in a vain attempt to rub some of the tiredness out of her system. After a 16 hour shift she was ready to go home and crawl into bed for the next 10 years. Sadly that wasn’t really an option since she had to be up and at work at 7’o’clock the next morning.

After nearly 4 years with the FBI’s biocontainment lab without a promotion she was starting to wonder where this career was actually going. It wasn’t that she didn’t like the work, each case was unique and interesting it was just that she really needed more money to pay off her student loans then the government was paying these days. After all medical school and a doctorate in biology hadn’t come cheap.

“So tell me what you think Dr. Longman.” said a voice from behind her.

“Ah Director Prescott I didn’t hear you come in.” said Alexis nervously, she tried to pretend that she had not just jumped like a frightened field mouse. Dr. Prescott has the nasty habit of jumping out of the shadows, a pastime he desperately enjoyed, much to the chagrin of his employees. “This is a really weird specimen.” she said looking through the glass containment case at the section of preserved tissue contained within.

“How so?” said Director Prescott quietly.

“Well on the surface it looks like a regular tentacle, much like that you would find on many invertebrates, like an octopus for example…” Alexis started uncertainly

“Except?” asked Director Prescott

“Well except for a lot of things, for one thing the muscles are extremely densely layered, to the point that one tentacle may well be able to lift over 200 lbs. Another thing is that this part at the end appears to have some sort of combination between a tongue and a urethra, it way well be this organism’s penis.” Alexis continued

“A penis that can lift over 200 lbs?” said the Director incredulously

“And another thing, this appendage was severed at the end we have no idea how long it is in reality, it could have gone on for a few more inches or a few more feet for all we know. What’s more is that unlike the tentacles of an octopus or a squid this tentacle isn’t slimy like you would expect, it actually looks like it has regular skin on it. Where did you say this was found?” Asked Alexis

“Not to far from here actually.” said the Director “In a park about a mile from this building.”

“Bridge view?” asked Alexis “I walk through there every night on my way home.”

“Well I’m sure it was probably just some weird variety of squid crossbreed or something, nothing to worry about” said the director dismissively

“I sure hope so.” said Alexis to herself

“Now be sure to put this specimen back into cryo-storage when you’re done with it, and don’t forget to lock up when you go.” said the director

“Yes sir.” said Alexis

Alexis replaced the specimen into the cryo-locker, scrubbed down the lab table she had been working on and switched off the light on her way out. Deciding that she felt sweaty after working so long in the lab Alexis headed towards the faculty showers.

“Man it’s a good thing that I brought a change of clothes.” she said to herself

Stepping into the women’s shower room Alexis glanced around, the long rows of metal lockers and plain wood benches gleamed back at her with the high polish of a surface that had just been clean and the hint of chemicals in the air gave to room a clean and sterile feeling. During the working day the showers were usually packed as many of the staff took advantage of the faculties free water and a great deal of the work done in the labs was labor intensive and a good shower was often required if you wanted to keep up a business like appearance.

“I guess there are some pluses to working late.” Alexis said to herself enjoying the solitude of the empty room “I have the showers all to myself.”

Removing her lab clothing Alexis paused to examine herself in the full length mirror attached to the end of one of the banks of lockers. Long hair coming down to the middle of her back helped to frame her heart shaped face and deep green eyes peeked out from between the lenses of a slim pair of rimless glasses, her skin was a soft white which was smooth and free of blemishes, years of constant exercise had hardened and toned her muscles giving her a lean appearance without robbing her of her curves, full round breasts sat high on her chest sagging only slightly under their own weight with her nipples pointing straight out, her wide hips led the eyes down invitingly to the full pouty lips of her pussy. Alexis had always kept her pussy cleanly shaven preferring the look and feel to the alternative. Turning sideways her eyes traveled over the full rounded curves of her ass and down the well toned thighs to her slim calves.

“I look pretty good considering I haven’t been to the gym in a month.” she thought to herself

Alexis adjusted the water to her liking and stepped into the stall and closed the heavy frosted glass door quietly behind her. She raised her head letting the hot water run down her body in rivulets between her breasts and down her back, pulling her hair out of its pony tail she squirted some of her shampoo into her hands before kneading it gently into her scalp. Feeling the tension drain away from between her shoulders she sighed in contentment. She reached for her other bottle and squirted out some of the body wash she favored rubbing it between her hands before starting to apply it to her body. Starting at the top and working her way down she started to scrub of the sweat and grime that a days worth of hard labor caused, before too long she began to pay special attention to her breasts and clit enjoying the feeling of her hands gliding over the slick flesh of her breasts she moaned to herself pinching her left nipple gently between her thumb and fore finger before sliding her index and middle finger inside her pussy. Alexis moaned at the sensation it had been so long since she had sex with anyone because of the long hours and erratic schedule that her job forced upon her and her forced celibacy had caused her pussy to become extremely tight so that even her slight fingers felt like a thick cock. Under her skilled hands Alexis was able to quickly bring herself to a climax. Sighing morosely and leaning against the wall of the shower stall she felt the slight twitches which always accompanied an orgasm start to dissipate under the hot water of the shower.

“Man I really need to get laid.” she thought to herself

Quickly rinsing the soap off Alexis stepped out of the water into the cold air of the locker room she giggled to herself as she used the palm of her hand to brush her nipples made erect by her recent sexual release and the cold air. Walking over to her locker she pulled out the matching black bra and thong pulling them on before toweling off her long hair and pulling it back into a ponytail. She donned a short black skirt and tight fitting white blouse which showed off her full C cup breasts to full advantage. Whistling a nameless tune to herself Alexis walked out of the room switching the light off behind her.

The park seemed especially menacing to Alexis that night in the light of what she had recently learned from the Director.

“I wonder if the creature which has spawned that tentacle is out there in the forest somewhere.” she thought to herself

Hearing footsteps behind her she glanced back and saw a giant of a man walk out from the darkness of the forest. Easily 8 feet tall the man was built like a linebacker but Alexis couldn’t tell much about how he looked because he was dressed in a long black trench coat which reached almost to the ground while his face was obscured by a wide brimmed hat which was pulled down.

“A beautiful night out isn’t it?” Alexis asked

The man stood silently for a second before stepping into the light and meeting Alexis’s eyes. She took a step backwards in horror; the man’s eyes lacked any kind of pupil and instead glowed with a malevolent red light. It grinned manically exposing long sharp teeth and a long tongue snaked out of its mouth.

“What are you?!” asked Alexis

For answer the creature opened its trench coat, while shaped roughly like a man with powerful well defined muscles nearly a dozen tentacles identical to the one still in the cryo locker in the lab seemed to be attached to its chest, her eyes widened as she saw that its penis was enormous easily two feet long and as thick as her fist was wide and it was already standing at full attention as the creature lustily examined her. Alexis’s first thought was to run but before she had made it more then a few steps before two of the tentacles shot out, wrapping around her thighs, she reached down to try and pull them off before two more shot out and wrapped around her wrists while another wrapped around her throat sending an unequivocal message about what would happen if she screamed.

Lifting her helplessly into the air the creature carried her into the darkness of the forest. Alexis felt one of the tentacles slither up the bottom of her skirt before it ripped it off of her body shredding the garment in the process, two more slid up the bottom of her blouse before jerking out words ripping the buttons from the shirt and strewing the pieces around the clearing they had stopped in. Now clad in nothing but her matching bra and thong Alexis shivered in the powerful grip of the monsters tentacles. Lowering her to the ground one of the tentacles snaked inside the bottoms of her panties ripping them from her body before climbing up and doing the same to her bra leaving her completely nude and totally helpless before the monsters will.

Alexis struggled against the tentacles trying vainly to free any of her limbs from its powerful grip. She looked down and saw the top part of one of the tentacles open and a long tongue emerged from its tip, the tentacle moved closer to her pussy and begin sliding the tongue up and down the length of her slit before thrusting deep inside her. Alexis cried out at the unexpected intrusion as the tentacle slithered deep inside her pussy. The others pulled her arms and legs apart leaving her completely spread eagle while it slid in and out of her tight hole. Two more of the tentacles circled her breasts squeezing them in its powerful grip before emitting tongues of their own which begin to flick the ends of her nipples before completely engulfing them in their miniature mouths. She continued to struggle trying to get away from the unwanted intrusion of the tentacle inside of her and opened her mouth in an attempt to scream for help, but before she could complete her scream one of the tentacles stuck out and forced its way into her mouth forcing her to silence.

Another of the tentacles sliding up her leg, passing its fellow still thrusting in and out of her pussy like a pistoning cock the other tentacle circled up closer to her ass, emitting a tongue it’s started to caress her asshole genteelly lubricating her tender hole with its vicious saliva before forcing itself deep inside her virgin ass. Alexis cried out in pain as it borrowed its way inside her but the tentacle in her mouth allowed no sound to emerge except a quiet groan.

Lifted up in the air by the powerful force of the tentacles which surrounded her body Alexis’s every hole was filled with the tentacles the one in her pussy thrusting in and out of her repeatedly, though she fought against it at first her hips begin responding in the primal animal way her body was programmed by a million years of evolution to respond when she was being fucked, she spread her legs further apart and started thrusting down each time the tentacle thrusted up meeting it in the middle and increasing the force of its pounding on her tight pussy, the tentacle in her ass started acting in a similar fashion slowly sliding in and out increasing its speed each time just a little.

What started out painful started to feel good as her ass started to loosen up under the rough care of the tentacles. Alexis started to suck on the tentacle which filled her mouth and it to begin to move in and out filling her mouth each time and causing her to gag just a little as it fucked her throat. She could feel her orgasm building as she was fucked from all angles loosing herself in the stimulation of having her mouth, ass, and pussy being fucked while also having her nipples and clit sucked on, under normal circumstances she would need at least 6 men in order to get the same amount of stimulation. Alexis cried out as a powerful orgasm ripped though her body causing her muscles to contract as she shook from the force of the most powerful orgasm she had ever experienced.

The tentacles in her mouth, ass and pussy extracted themselves, the top part opening, each of the tentacles started to ejaculate on to her covering her head to toe in the thick white spurts of its cum. Alexis moaned as she felt the monster cum on her still dazed and a little confused from the force of her orgasm, she felt herself being lifted closer to the monsters body as it lifted her into a sitting position suspended in the air, pulling her legs apart the monster positioned her above the head of its monstrous rock hard cock. The tentacles started pulling her down and she thought she was going to be split in half as the enormous cock started to penetrate her, deep inside she felt the massive cock finely bottom out in her pussy before being dragged upwards again. Up and down the monster slid her on its massive cock increasing its speed before she was being fucked faster and harder then she had ever been before, its huge hands reached around and grasped one of her tits in its powerful grip using the other hand to pull her hair back forcing her head up it pressed its lips against her mouth its long tongue flicking around on the inside. Alexis felt the enormous cock start to twitch inside her as the monster continued to pound her.

Despite the pain of having something so large violate her tight pussy Alexis could feel another orgasm starting to build, she could feel it moving faster and could tell from the way that its gigantic cock was starting to twitch inside of her that it was probably going to cum soon. Alexis started moaning loudly as the tentacles lifted her helplessly up and down on the monsters cock, using her like a sex toy to satisfy its dark sexual urges. The monster roared out in pleasure and Alexis felt the cock start twitching a moment before a massive amount of cum flooded her inside sending her over the edge into her own orgasm mixing its cum with her own. Half way through its orgasm the monsters tentacles lifted her off and positioned her right in front of its cock coating her again in another layer of its cum. When it finely finished Alexis could feel the tentacles grip start to slacken as it dropped her to the ground where she lay helplessly before it. The monster gave her a sadistic grin before picking up its clothing and leaving. Alexis watched it’s back retreating into the darkness as she lay on the forest floor completely nude and covered in the monsters cum. The last thought that passed through her mind before the darkness of unconsciousness took her was to wonder if she could get pregnant from the massive amount of cum that was still seeping out from between her legs…

[contact-form]

Tentacles

Ads

Good Morning Everyone

As some of you may have noticed there are now ads on the site, I am doing this to pay for the increasing server fees that I pay to host this website, I hope that they are as unobtrusive as possible

I will try not to have giant banners like this on the site since I realize that they are distracting and annoying. I apologize in advance if anyone is annoyed by this development.

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My Mom's Best Friend

I was never what you would call “popular” with the ladies. I was never fighting through throngs of girls. So it wasn’t really a surprise when after my 19th birthday I still hadn’t ever had a serious girlfriend or lost my virginity. I was always more into computers than real people anyway, or at least that is what I tried to tell myself.

Which leads me to my mom’s best friend. They had met while they were in college, and while my mom had settled down and had children Janet had never really lost the rebel fire they had both had in their youth. A bad marriage and a messy breakup led to Janet staying with us for awhile while she was looking for a place of her own. I pretended to be annoyed at having another person in the house, but secretly I was thrilled, because Janet was fucking hot, well if you are into MILF’s. I never really hoped for anything to happen, maybe catch some glimpses of her in her underwear, maybe “accidently” walk in on her in the shower if I was lucky. I wasn’t prepared for her to be my first. It started out with me trying to spy on her. I was pretty sure that I had a good spot to watch her changing clothes from without being caught but I got spooked when she looked in my direction and rushed off back to my room. I thought my heart would explode in my chest when she knocked on my door a few seconds later. I wasn’t sure what to expect, maybe a telling off, maybe some threats, but nothing prepared me for what came next.

“I saw you spying on me…” she said.

“I’m sorry…” I said, hanging my head in shame.

“I didn’t say it was a bad thing did I?” she responded

She pulled back her pants, giving me a glimpse of the lacey black panties she was wearing under her jeans. I felt my heart skip a few beats and my palms immediately got sweaty.

“You don’t have to spy on me you know…” she said “after all I am right… next… door…” her hands slid up her stomach and cupped her breasts as she spoke, sending an unequivocal message as to her intent.

I stuttered something incoherent, my brain not quite working properly due in large part to a majority of my blood flow having been directed to lower places. I had watched her with lust in my eyes since I hit puberty, I wasn’t entirely convinced that this wasn’t some sort of dream.

I was still trying to process what she had said when she closed the distance between us and pressed her lips against mine. The sweet flowery scent of her shampoo and body wash filled my nose, her lips pressed firmly and insistently against mine. I could feel the hunger in her body as she pressed against mine. A million years of evolutionary instincts took over and my arms slipped around her, pulling her tighter against me. One hand cupped her ass, pulling her hips to me. My cock swelled in my pants and she moaned as she felt my swollen member press against her through our clothing.

Her tongue wormed its way inside of my mouth, full of warmth and desire. Our mouths battled with each other, each desperate to gain some sort of leverage over the others. My hands started to get braver, one hand slipping down the back of her pants and cupping her bare ass. She moaned into my mouth, the sound muffled by our warring tongues. I thrilled at the feeling of her breasts pushing against my chest. This was already as far as I had ever gotten with a girl.

Our bodies separated briefly and I took the chance to slide my hand up between us, pawing at one of her breasts over her clothing. My cock was straining and begging to be freed. She giggled at my clumsy attempt at feeling her up.

In a scarce handful of seconds she shucked her shirt and bra, another few seconds freed her of her pants as well. In mere moments she went from my mom’s friend, fully clothed, to a naked goddess standing in front of me with nothing but her modesty and a tiny pair of black lace panties, neither of which covered much. I am not sure if my jaw literally dropped but I probably did a passable impression of a fish out of water.

She giggled again, “you seemed like you were trying to get somewhere, so I figured I would help you out…”

I gulped and did the sensible thing and kept my mouth shut.

She returned to the circle of my arms, her body radiating heat like an open furnace. What had been a dull ache before was now a desperate desire that surged inside my chest. The part of my brain that made sensible decisions shut down, all that was left was the animal section that wanted to rip off what remained of her clothing and take her, preferably as roughly as possible. I never knew that this part of me had existed, but I wanted to bite her, to scratch her, to mark her as mine.

I grasped at her breasts, now unrestrained by her clothing.

“Gentle” she cooed at me in a tone that was both breathy with desire but held hints of reprimand as well, “they are attached you know” she giggled at the last part. Her hand covered mine and pressed softly but firmly against her flesh.

“I want to feel your pussy” I moaned into her ear full of eager desire

She took my hand and guided it down between her legs, I pushed the thin piece of fabric that covered her crotch out of the way, exposing the soft full lips of her pussy. Wet heat rolled out from between her legs as I slipped one finger into her tight hole. She bit her lip and closed her eyes, appearing to enjoy the touch. I forced my index finger deeper inside of her, penetrating deep inside her womanhood. I reached as far inside of her as I could and started to force a second finger inside of her, she moaned at the additional intrusion into her pussy. I started to slide my fingers in and out of her cunt, feeling the gentle pressure of her muscles on my intruding fingers, I increased in speed slowly, pumping in and out, the moisture of her arousal easing the passage of my fingers. One of her hands shot out and gripped mine around the wrist, freezing my fingers in place inside of her. She made a sort of guttural growling sound in the back of her throat and her body shuddered.

“god damn that felt good” she said smiling.

“what happened?” I asked, confused.

“I just had an orgasm” she said, her tone indicating that I should have realized that on my own.

“Oh I thought women usually threw their head back and screamed when that happened…” I said blushing furiously

“Only in pornos” she laughed. “Now it’s your turn”

She dropped to her knees in front of me and started to unzip my jeans. I was worried that my cock was going to pop up and hit her in the face, as much tension as I could feel in it as it strained to free itself. She made another growling sound as she released my cock from inside of my boxers, sliding on hand along the length of my shaft. A small bead of precum glistened on the tip and she scooped it up with one finger before sliding it into her mouth. She made a sound of approval as she licked her finger clean. She took my cock in one hand and brought it up to her face. I shuddered involuntarily as she ran her tongue from the base of my cock all the way up to the tip before plunging the entire member into her mouth. She made a slight gagging noise as my cock hit the back of her throat and she seemed a little surprised.

“You are bigger than my ex-husband” she supplied noticing my confused reaction

I made a noncommittal noise of agreement and she continued. With rapid bobbing strokes she rose and fell on my cock, each stroke taking the entirety of my cock inside her mouth. I closed my eyes and groaned, the moist heat of her mouth and the deft use of her tongue was like heaven itself.

“stop” I said.

she looked at me confused.

“I want to fuck you” I said.

She smiled and stood up, she slipped out of her panties, leaving them to join the rest of her clothing on my bedroom floor.

She sat on the edge of my desk and leaned back, spreading her legs invitingly and giving me an unimpeded view of her body. If my cock had not already been rock hard that would have done it on its own. For someone in her 40’s she had the breasts and body of someone much younger. The absence of children and a strict training regime had kept her in excellent shape. I noticed in that moment that contrary to what I had believed her pussy was not entirely shaven, she kept a small patch of hair decorating the top of her slit. I approached her and stared at her bare body in disbelief. Only 24 hours ago if you had told me that I was going to lose my virginity after all this time I never would have believed you. I lined the head of my cock up with the opening to her pussy, slipping the head around between the lips of her pussy as I had seen actors in porn do. She groaned softly and scooted towards me slightly, as though eager for me to finally put my cock in her. When I could take the anticipation no longer I sunk my cock into her, taking the final step into adulthood and leaving my virginity behind me. Her cunt grasped my cock tightly, and had she not been so wet I am not sure I would have been able to force my way inside of her at all. She moaned, more loudly this time, as I slid inside her as far as I could. I started to slide back out again before driving my cock into her forcefully, causing her to slide back on my desk and bump her head against the wall.

“sorry…” I said abashed, she smiled in response and urged me to continue.

I started to work my cock around inside of her, leaning over slightly to angle the head of my cock down. She took the chance as I was leaning over and pulled my head down into a passionate kiss. Again her tongue hungrily searched inside of my mouth. As our kiss broke I saw that her eyes were glazed with lust. I leaned down further and pulled one of her nipples into my mouth, biting it gently and eliciting a squeal surprise from her. With all the care I could manage I pinned her nipple between my front teeth, flicking the end of my tongue back and forth across the sensitive nub. I felt her cunt grip my cock more tightly, the way that it had gripped my fingers not so long ago, and her body shuddered again as another orgasm rocked her. I could feel the rhythmic contractions as she came. We kissed again and her mouth was cold but no less full of desire.

I continued to pound at her pussy, I was surprised that I had been able to last for as long as I already had, especially since this was the first time I had ever fucked someone. I could feel my balls start to tighten and knew that I was going to cum soon.

“I’m going to cum” I moaned

“pull out!” she commanded. I obeyed wordlessly and ripped my cock from the warm embrace of her cunt. She again dropped to her knees in front of me taking my cock in both hands and thrusting it into her mouth. She wrapped her tongue around the sensitive head and sucked on it like she was attempting to get a golf ball through a garden hose. This was all that I could endure. An eruption of cum exploded inside of her mouth, coating her tongue and rolling down her throat. She swallowed and made a satisfied sound as she licked the last of my cum off.

“Don’t tell my mom….” I said, worried now that my common sense had returned with the flow of blood

“Yea… I think that would be a bad idea…” she said smiling, “after all if she knew we would never be able to do this again, and I bet you will be even better the next time…”

My Mom's Best Friend