This story was split into 2 parts. Jump to any of the segments from here:
1|2
Note: This story was originally submitted as one long story
and it was only broken into 2 parts for faster page loading.

Her finger started moving faster and more vigorously on her pussy. Her fingers were soaking wet and her juices were flowing freely from her cunt to his desk, leaving a small pool of wetness. Jessica started to moan and threw her fingers shamelessly in and out of her snatch as her body was wracked by the cum she had induced on herself. She stopped frigging herself and sat panting on his desk in the afterglow of her cum.

"Bravo Jessica! Bravo! I can tell my the state of your cunt that you quite enjoyed that.", said Evans. Jessica had almost forgotten her situation, so wrapped up was she with her orgasm and started to close her legs at the sound of Evans' voice. "Now, now Jessica, stay spread for me please. I'd like to enjoy the sight of your cunt for awhile while I ask you some more questions. Tell me, has Darryl ever given you an orgasm like the one you just gave yourself?"

Jessica blushed in shame, "No sir, he hasn't."

"I see. Has he fucked that perky ass of yours yet?", asked Evans, who could already guess at that answer.

"NO! That would be too painful! He hasn't even asked me to do that." Jessica cried.

"Tell me. When you suck Darryl's cock does he cum in your mouth?" Evans questioned.

Jessica just shook her head in answer.

"No? Has anyone ever cum in your mouth?" asked Evans disbelieving.

Jessica shook her head again in response.

"Really? And why is that?" probed Evans.

"I would never let anyone do that to me. I pull my head away when they are about to cum." Jessica admitted, trying hard not to notice the ever present bulge in the Principals pants. Up until this point he hadn't touched her - humiliated her yes, but hadn't touched her. Jessica somehow knew that they were soon going to move on to the next stage of her punishment.

"Hmmmm...I see. Get off the desk slut, and drop to your knees.", ordered Evans. The terrible man pushed his chair a little way back to accommodate his prize. He leaned back in his chair and put his hands behind his head. "Come over here and kneel between my legs." He smiled when Jessica obediently complied. "Now undo my pants and take them off. You'll have to get rid of the shoes and socks too." Tears started to flow from Jessica's eyes again as she reached past his bulge to his pants. She undid his button and unzipped his fly quickly. Evans raised his ass up so the sexy teen could pull his pants off. She did so, being careful to avoid his bulge and underwear. The ugly man was taking off his shirt and tie as Jessica did his bidding and now sat in his chair in his underwear. Jessica couldn't help but notice that the principal's bulge seemed a bit larger than her boyfriend's. She waited for the next command.

Evans just sat there staring down at the teen kneeling before him. His eyes raked over her quaking breasts, tear stained face, and now barely concealed patch of pubic hair. He couldn't wait to see her full lips wrapped around his cock. He would make sure that she sucked him off and swallowed every drop of his cum. Evans leered at her, licking his lips before he spoke his next words. "Now I want you to take off my underwear using nothing but your teeth."

Jessica started up at him in disbelief. This would force her to have contact with his body a bit sooner than she expected. She leaned up and into him, her big tits forced to sit on his fat thighs while she moved her mouth higher to the waistband of his jockies. She shivered in disgust as his throbbing bulge rested neatly in the curve of her neck as she bit into the fabric. She quickly pulled down on the material, her nose rubbed into the pubic hair that was quickly being exposed as she did his bidding. His cock slowly sprung into view. It looked very thick, with large veins running all around it. She managed to tug the material all the way down, past the head of his cock, which now stood up proudly. The fabric slipped from the teen's teeth as she stared at the massive cock. She had never seen anything so huge in her young life. It was at least the width of her slim forearm, and nearly as long as it too. She shuddered in fear at what that monster could do to her.

Evans watched her reaction to his cock with pleasure. He knew that it would take this luscious teen some time to get all of it in her mouth - but he had nothing but time now.

"Okay girly, you know what to do. Suck my big cock!" Jessica tentatively moved forward and started licking his shaft with just the tip of her tongue, stomach churning as she heard her principal's moans of delight.

"Now...is that the way you suck and lick a cock? I'm disappointed in you Jessica." With those words the principal leaned forward and grabbed the back of the teen's head. "Open your mouth and suck on my cock, or I WILL call your mother!" the man threatened. Jessica opened her mouth and the man guided her head over his cock, letting her take in as much as she was used to at first. Jessica's mouth was being stretched farther than it ever had been before. The spongy head of his cock pushed past her lips and bumped the back of her throat, making her gag. She started moving her head up and down on his cock.

"Use your tongue while you do that, and play with my balls." He continued to instruct her. Evans groaned with pleasure as she complied. No woman had ever sucked his cock before and he was enjoying it. He wanted more, he wanted her nose buried in his bush and she deep-throated his massive cock.

"Okay Jessica, you are now going to suck cock like you've never sucked before." Before she could raise her up to question him his hand started pushing her head further down on his cock. The head hit the back of her throat again, and yet he kept pushing and pushing until it popped into her esophagus. He still didn't let up, though the young teen had started flailing. "Take it all you cunt" rasped Evans. With that he pushed her head the rest of the way down, engulfing his cock in her throat. "Ah!!! That's it!" He enjoyed watching Jessica struggle to breathe around his cock. He slowly withdrew his member from her throat, and she managed to gulp some air before he slammed it down her throat again. Over and over the processed repeated, until the principal started to feel the cum in his balls starting to churn.

"God, I'm going to cum. Swallow every drop, or you'll continue to suck my cock until you finally do! Unghh---I'm cummmminggg!!" shouted Evans as he slammed his cock down Jessica's throat one final time, pouring his seed down into her stomach, not giving her a chance to spit it out. Again and again his cock spurted as he clutched her head in his lap. Finally he withdrew his member from her throat. Jessica collapsed in a crying heap at his feet, gasping for air. Evans allowed her to stay on the floor for a minute while he relished his first orgasm at the hands of his prize. However, looking at her heaving breasts was getting him excited. Her legs were splayed out giving him a good view of her slick pussy, and his now slack member jerked with anticipation.

"Break is over sweetie! Come over here and sit in my lap." Evans extended his hand to her on the floor. The teen slowly stood up and went to sit in his lap as instructed. He helped her get settled, sitting sideways in his lap, one arm over his shoulders, and the other hanging limply in her lap at a more attempt to hide her pussy. "That was an awesome blowjob my dear," Evans said "next time you'll know what I expect and will not need my assistance."

Jessica's eyes widened "Next time sir?"

"You didn't think that this would only happen today did you? There are several months until graduation, and I expect you to pay every day for what you've done." Evans uttered these words just as the thought came to him. Jessica hung her head dejectedly, knowing that he could do whatever he wanted to her at this point, she had to protect her mother at all costs.

Evans eyed her mouth hungrily and grabbed her head and plunged his tongue in her mouth, kissing her roughly. His tongue snaked along hers, rubbing against the walls of her mouth and her teeth, tasting every inch of her mouth. While he ravaged her mouth his right hand crept up to engulf her breast, squeezing and feeling the weight of it. He broke their kiss and ogled her tits, removing his hand. "Take your hand and show me again how you play with your tits." Jessica took her hand and started rubbing and pinching her breast, pulling at the nipple. "You have the best titties I've ever seen." He said licking his lips, and leaned into her chest, his mouth aimed at the nipple she wasn't playing with. He started lapping at the nipple, making it hard in spite of itself. Jessica stopped playing with her breast while he slobbered on her tit. He promptly took her hand and placed it on her breast, urging her to continue. He started sucking hard on her nipple, squeezing the breast with this hand as he did so. Between her ministrations and his attention unexpected feelings started in her pussy, she almost felt turned on - almost.

All of a sudden she felt his cock growing again under her ass. She squirmed in his lap in an effort to avoid contact, but only succeeded in making him hard faster. "See what you do to me slut?" mumbled the ugly man to her tit, humping his cock into her for emphasis. "My cock wants to fuck you silly. But I'm not sure you're ready for that yet." His hands plunged between her legs, spreading them wide so that he could plunder her pussy. His fingers moved up to gently caress her slit and spread her lips. His finger gently pressed on her clit, pinching it between his thumb and forefinger - feeling her slipperiness beneath his fingers. He stroked the folds of her outer cunt, rubbing her everywhere and making her gyrate. He couldn't wait any longer and plunged two fingers into her cunt. Jessica gasped at the intrusion into her hole, and squirmed trying to dislodge the probing fingers, but it didn't work. Principal Evans continued to suck on her tit and moved his fingers within her cunt. He moaned as he felt how hot and moist she was down there. He pushed his fingers in deeply, the tips of which scraped on her cervix. He fucked her cunt roughly then, quickly plunging his fingers in and out at a furious pass.

Jessica didn't know what was coming over her body. An incredible burning sensation was forming in her womb. Her hips bucked in an effort to keep pace with the huge fingers. She arched her back to try to force more of her tit into the ugly mans mouth. She was enjoying the feeling of his fingers in her pussy. The fire grew larger and larger, until she grabbed at the hand in her cunt and forced it even deeper. "Oh God, I'm cumming, cumming, cummm....oh ya, fuck me with your hand.....ahhhhh" Jessica groaned in ecstasy.

"Cum for me my little slut." Urged Evans "Cum all over my fingers" he said while picking up the pace and adding another finger to her soppy snatch. Jessica was a wreck. Her orgasm overtook her and she flopped in his lap like a fish out of water. The principal took the time to watch her face and a variety of emotions overtook her as well. Pleasure at the orgasm, as well as fear that this ugly old man could make her cum like that, and disgust that her body betrayed her. Jessica sat in his lap sobbing in despair, she didn't know how to feel anymore, or what to think.

The principal's fingers were still in her snatch, and he slowly withdrew them as Jessica whimpered in confusion. The principal brought his sticky fingers up to his nose and inhaled deeply. He took his fingers and inserted them in his mouth, licking them clean. "Your pussy tastes wonderful, kind of like honey and chocolate mixed together. Here, have a taste." Evans put his fingers back into the teen's pussy again, and after giving her a few more strokes, so he could hear her whimper again, he withdrew them. "Here, lick my fingers clean slut." He put his fingers onto her lips and pulled on the back of her hair to make her open her mouth. She did and tentatively licked juices off of his fingers. He then put his fingers all the way in her mouth and told her to suck them clean. Jessica did, surprised that she didn't taste all that bad. Evans withdrew his clean fingers and plunged them again and again into her pussy. He tasted her several times in this manner, every so often letting her have more too.

"I can't get enough of the taste of your cunt dear." With that he grabbed her and stood up quickly, maneuvering her so that she was over his shoulder. He walked over to the mirror in his office and spent some time spreading her ass cheeks open and her pussy lips open so he could look at their reflection. Jessica's face hovered over the man's ass, and her breasts pressed into his shoulders, whimpering under his ministrations in the mirror. He walked over to the couch in his office and flipped her onto it. Jessica sat there stunned for a minute at the abrupt dismount.

"You said that you've never been licked before, is that correct?" inquired Evans as he got down on his knees in front of her. He reached out and put both of her heels on the couch and spread her legs to give him an eyeful of her sopping wet pussy.

"Yes sir, never." answered the teen.

"Oh ya...I get first taste then!" With those words the man grabbed her hips and started pulling her closer to his face. He stopped just short of her clit and inhaled her musky scent. He extended his tongue and roughly started licking her clit, lapping up her juices.

Jessica squirmed in protest, "No, please don't do that. Please...it feels strange." Jessica didn't know if this felt really wrong, or really good. All she knew is that she couldn't sit still. It felt like there was a huge wet finger rubbing her clit where she normally would.

Evans was in heaven. Jessica was making little mewing sounds and was bucking her hips beneath him. He wasn't sure if she was even aware she was doing that. He reached up and put his fingers in her cunt again, moving them in and out as he continued the assault on her pussy with his tongue. Jessica writhed in pleasure under him. Evans knew he could intensify this orgasm for the teen. He continued with his fingers in her pussy, reaching up with his other hand and using it for awhile, getting the fingers nice and wet. He pulled on her hips, making her ass hang over the edge of the couch, while he continued fingering her snatch. He switched fingers again in her, and used the other hand to rub some moisture on her ass. Jessica instantly felt the probing in her nether region.

"No, not my ass please!! No...no....ouch...ahh...it hurts.!" Jessica cried as the finger started pushing into her ass hole. The finger in her ass now started to move in rhythm to his other hands. Jessica's crying quickly turned to moaning as the intensified feeling started to work it's magic. Evans added more fingers to her cunt and moaned on her clit as she took it all. Her ass hole started to expand under his finger and he quickly added another one there too. He lapped her overflowing cunt and felt the walls of her vagina start to contract on her fingers as another orgasm overtook the teen.

Jessica was shocked at her body's reaction yet again. The fire overtook her so fast that she didn't have time to cry out. The teen's body started to spasm and rock as the orgasm took her. Grunts and groans and babbling started to pour out of her mouth as a second orgasm followed on the heels of the first. Still the man on his knees ate her. He withdrew his fingers and fucked her hole with his tongue, sucking the sweetness out.

Jessica stopped moving, and lay exhausted with her legs still spread open for the principal. Evans sat back and admired his handiwork. The teen princess was defeated, she didn't bother closing her legs and now could not deny that she enjoyed getting fucked.

"How is my little whore doing? Are you ready for some real fun now?" Evans said to the teen as he masturbated his cock in front of her. Jessica turned glazed eyes towards the man.

"Please sir, no more. I can't....I can't take anymore. I'm too tired." Begged Jessica.

"What? You'd leave me with a hard-on like this? You cunt!! After all I just did for you?!! You selfish whore." Evans' anger was being stoked. He thought that she would be begging him to fuck her at this point. After his first orgasm he thought he'd be nice and give her some pleasure, and this was the thanks he got! Well forget it! "You ungrateful cunt! I'll show you!"

Evans got up on the couch and pulled the stunned teen up and over his lap. He was starting at the perfect globes of her ass. "You ungrateful bitch!" he roared as his hand connected sharply with her ass. Jessica cried out in pain. Evans continued to rant and rave as his hand came down on her ass again and again. Jessica cried and then screamed as the onslaught continued on her ass. Evans' rage was finally assuaged as he looked at her now glowing ass cheeks. Jessica was crying uncontrollably at his feet.

Evans' cock had never been harder than it was after spanking the teen. He plunged four of his fingers into the girl's cunt to ensure she was still wet. "You think you're leaving without me fucking you? Think again!!". Evans flipped the teen onto the floor and dived on top of her. She struggled with the now crazed man. "I'm going to fuck you so hard that you won't be able to speak anymore you slut.!" Evans put the teen's legs over his shoulders, exposing her pussy to his throbbing cock.

"Please don't, you're too big, you'll rip me, you'll....aRRRGGGHH!!!" screamed Jessica as with one shove the perverted man plunged his dick all the way into the frightened girl. Never before had she been filled like this before. Evans started to fuck her violently, rapidly moving in and out of her.

"So you'd leave me eh? What a tight cunt you've got bitch. I'm going to fill you so full of cum baby. Ah man...look at those titties." Evan's continued the onslaught with his cock and leaned forward to play with her tits again. He thumbed the nipples over and over again, and then started sucking on them feverishly. He slobbered all over them, licking and nipping at them - squeezing them roughly. Jessica was overcome with feelings. She had never been fucked like this before, and felt her hips start to move to accommodate the man's fucking. Jessica heard herself moaning as though in a dream. She slid her legs down his arms and pushed them so they were wrapped around his waist. Her hands grabbed his head and continued to push it into her tits.

"Fuck me hard, Oh ya, Cum in me, fill me up...pleeeassee!!" babbled the fucked teen.

Evans couldn't believe his ears. His balls started to churn at the words she was throwing at him. He sat back up and started pistoning his cock out again as the orgasm overtook him. "Fill you cunt, fill you up good...take it you whore, take it all!" groaned out Evans as pint after pint of fluid jettisoned out of his cock into her womb.

Jessica's own body was being put through a series of orgasms. Her body was convulsing as orgasm after orgasm overtook her. Jessica's mouth gaped open as they happened, but nothing came out.

Evans finally collapsed on the teen, tit still in his mouth, and they both lay there in a state of complete bliss. Evans was the first to stir. He got up to his knees and wiped his wet dick off on her leg. He unsteadily to his feet and walked to where her clothes lay. He tossed them on her sweaty body "Get up and go home whore. Be in my office at 4:00."

Jessica pulled her clothes over her body and prayed that she would not run into anyone on the way home. Jessica was lucky that her ill mother was staying over at her aunt's for a few days while recuperating from some tests. Jessica managed to get home and spent an hour in the shower, trying to erase her principal's sperm and the feelings of him on her body. She couldn't help but admit that today was the best fuck she had ever had, and that she wanted more. An exhausted but sated Jessica tumbled into bed and passed out cold.

To Be Continued...

This story was split into 2 parts. Jump to any of the segments from here:
1|2
Note: This story was originally submitted as one long story
and it was only broken into 2 parts for faster page loading.

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