Lilly Ch. 01

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

"No! I said in my lap you need to be close enough to spank, my arms aren't a mile long!" Said the Head Master

Lilly moved closer and positioned herself over his lap, the head master grabbed her by her pony tail 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 Head Master

"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 Head Master

"No..." Lilly said mournfully

"Then let's begin." Said the Head Master 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 cotton clad breasts straining against the tight material of the thin white cotton blouse of her school uniform was rubbing against the Head Master concealed cock. After ten stokes 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 Head Master "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 Head Master 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 your 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 head master continued to spank Lilly his large muscular hands striking her backside firmly, each stroke became a little softer then 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 head master 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 Head Master 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 Head Master 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 head masters 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 head master crotch. The head masters 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 Head Master "If you disobey your ass will be punished even worse."

Lilly nodded in understanding

The head master 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 steal 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 Head Master 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 head master 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 Head Master

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 Head Master

"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 head master 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 Head Master

"I'm sorry sir." responded Lilly "I couldn't help it."

"Your not sorry yet, but your about to be." Said the Head Master "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 head master unzipped his pants and pulled out his cock, Lilly eyes widened at the sight, it was more then a foot long and looked to be thicker then both of his fingers but together and it wasn't even fully erect yet.

"Come here slut." said the Head Master

Lilly approached him uncertain of what to do.

"Get down here." said the Head Master 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 Head Master "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 Head Master

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 Head Master

"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 then 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 for a moment before ripping her shirt outwards in one motion before returning to do the same to her bra, leaving her completely naked except for her plaid skirt which was bunched up around her waist. 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 finely 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 head master 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 head masters 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 Head Master

"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 Head Master

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 Head Master

"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 finely 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 "Cant you cum on my tits or something?"

"Ladies get to have men cum on their tits but sluts get their pussy pumped full of cum!" He said

He picked up his pace and her efforts to stop him ceased as she resigned herself to it. He kept pounding her until finely she felt the hot splash of his cum inside of her as he pulled her tight against him and pumped in every last drop of his cum, feeling his cum inside of her was enough to push her over the edge she screamed out in pleasure as she felt her orgasm go through her twitching against his body and mixing his cum with hers. 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 think 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 head master 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 Head Master 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 Head Master "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 Head Master "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 the panties he had given her were still soaking wet from the cum that had been seeping out from between her legs. But more then the pain and the cum Lilly's mind kept returning to the head masters office of her legs being spread by his powerful hands and his thick cock thrusting into her over and over again and she knew that it wasn't just his cum that was making her panties wet now.

The day finely ended with Lilly hobbling out to her car trying to ignore the sharp pain that had resulted from her visit to the head masters office. 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 head master 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. Finely settling on a small vibrator the package declared as a silver bullet.

"Hmmm... I can't wait until tomorrow so I can try this out..." she thought to herself.