Jenna's a Very Bad Girl Pt. 01

This is a work of pure fantasy.

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"You know who I've been thinking about a lot recently?" said Jenna Swanson, an 18-year old senior at Sunset High, a private all-girls school, one Monday lunchtime to her best friend Amber Cook, a fellow 18-year old senior.

"Who?" asked Amber. "Wait - is it a teacher?"

"Yep," Jenna replied.

"Oh my God who?" Amber asked, leaning forward.

"Mr. Reed," Jenna replied.

"Mr. Reed, the math teacher?" Amber asked.

"I know, I know," Jenna said, leaning back and running a hand through her blonde hair.

"You could have any teacher in this school...shit, any man in town," Amber said.

"So could you," Jenna interjected.

"Probably true," Amber replied, prompting both girls to laugh. "We do get a lot of attention from those dirty old men."

"Some of them barely fucking hide it," Jenna said.

"And you're going for Mr. Reed? OK,"

"That's right. And I'm gonna get him," Jenna said confidently.

"Oh really? Well we'll see won't we?" Amber replied. "How are you gonna do it?"

"I was thinking I'll leave him a note at first, and see where that goes," Jenna said.

"What are you going to write?"

"I'll think of something. Something simple, to the point," Jenna said.

"Like 'I want your cock inside me now. Yours sincerely, Jenna Swanson'?" Amber asked, making herself laugh.

"Something a little more subtle," Jenna said. "But not much."

Jenna perhaps wasn't the prettiest senior at Sunset High - that would probably be either Britney Wilson, a brunette whose cheek bones had caught the attention of modeling scouts, or Keisha Palmer, a black girl with flawless skin and features. She also didn't have the biggest breasts, as that was undoubtedly Melissa Butler, whose massive tits aroused attention wherever she went, among women as well as men. But it was the combination of her face and curves - her large breasts and round ass - which made her the sexiest girl in school (and maybe in the whole town). And the fact she knew it drove men wild.

She had noticed older men, including teachers at the school, checking her out on many occasion, some more discretely than others, and enjoyed the attention. The thought of them getting hard over her turned her on and was often the focus of her fantasies when she masturbated.

Amber wasn't far behind Jenna in terms of looks and attention she received. She had a darker complexion than Jenna, and was a brunette.

The next day in Mr. Reed's class, Jenna had her note already written. At the end of class, as she walked past his desk, Jenna discretely dropped the folded up note on it while he was talking to another student. He saw her drop the note out of the corner of his eye, and it distracted him from the conversation with the other girl. All he could think about was seeing what Jenna had left on his desk.

Jenna hadn't noticed Mr. Reed, who was in his late 40s, giving her the same amount of attention and looks as many of the other teachers had, and that was part of her attraction. The challenge. But he certainly wasn't immune to her. He told himself it was wrong but occasionally he couldn't help but glance at her, usually just her face but sometimes allowing himself to sneak a peek at her breasts, seemingly trying to burst out of her shirt, and her legs. Never long enough to arouse suspicion, but he definitely found it very difficult to look away at times.

Finally all the students left the classroom, and he opened the note. His mouth immediately went dry when he read it.

"I want you so bad. Any time, anywhere. J.S."

He couldn't believe what he was reading. Surely it was a joke, he thought to himself, a cruel prank by a girl who must know the effect she has on men. But what if it wasn't, his mind went on, and she really did want him. So what if she did, his conscience told him? He was her teacher and it's wrong, and besides, he could lose his job. But this was Jenna Swanson. He breathed deeply to try and regain his composure and stop his mind from racing.

He folded up the note and put it in his pocket, packed up his things, and left the classroom. He wouldn't be able to stop thinking about the note all day, and had an urge to tell someone about it. Even if it was just to make it seem less surreal.

That evening after school, Mr. Reed joined a colleague, Mr. Foster, at a local bar. Mr. Foster was in his mid 40's and had occasionally talked of his sexual attraction to some the senior girls, which Mr. Reed had found distasteful (without saying anything), but Mr. Reed had to tell someone about the note and figured he would be a receptive audience.

When they were nearly done with their second beer, he felt comfortable enough to bring up the note.

"Jenna Swanson? Jenna Swanson, the hottest girl in school, left you a note saying she wants you?" Mr. Foster asked incredulously. He had nearly spat out his beer when Mr. Reed told him.

"I know," Mr. Reed replied.

"Fuck, man. The number of times I've jerked off thinking of her," Mr. Foster, trailing off as he fantasized about Jenna's curves.

"You don't think it's a prank?"

"Only one way to find out," Mr. Foster said before taking a swig of beer.

"I'm not gonna do anything, if that's what you mean,"

"Why the fuck not? I would, definitely,"

"You would? I don't believe you,"

"If Jenna Swanson - JENNA FUCKING SWANSON - wrote me a note saying she wanted me, she'd be sitting on my cock the next day," Mr. Foster said, and Mr. Reed had to admit, the thought of that was incredibly appealing. So much so that he felt his cock twitch in his pants, hardening ever so slightly.

"Yeah but...," Mr. Reed replied

"But what? If you want to pass up the opportunity to have her ride you while you suck on those big, juicy tits of hers, that's up to you. But what a waste," Mr. Foster said. Thinking about that got Mr. Reed's cock harder, and he had to adjust the way he was sitting.

"I don't know. I bet she's not being serious anyway," Mr. Reed said, taking a final swig of his beer.

"Up to you. But you are one lucky bastard to have this chance," Mr. Foster replied, finishing his beer too.

Mr. Reed didn't answer.

"Well I gotta run. And I'll be jacking off over Jenna tonight," Mr. Foster said, and the two men got up, left the bar and went their separate ways.

True to his word, Mr. Foster did masturbate thinking of Jenna that night, and the conversation with Mr. Reed made it more intense than usual. He fantasized about her getting in his car, and leaning over to suck his throbbing meat, giving him an amazing, long, slow blowjob, deepthroating his cock, until he finally blew his load, filling her mouth with semen.

That evening, and the next day, Mr. Reed still found it hard to think of anything but Jenna's note. He was convinced he wouldn't do anything about it, that it would be unethical, but still he couldn't shake the thought of it. He had got hard thinking about what Mr. Foster had said after all. An involuntary reaction perhaps, but very real and impossible to hide.

Mr. Reed didn't see Jenna all day, which came as something of a relief. He stayed in his classroom for a couple of hours after school ended, grading papers as he often did, and had actually managed to not think about her for about an hour when he heard his door open behind him as he was packing up his things.

He turned, and there she was. Jenna Swanson. Her ample breasts strained the fabric of her shirt and the top few buttons two of which were undone, showing off her cleavage.

"Jenna...what...what are you doing here?" Mr. Reed asked.

"I wanted to make sure you got my note," Jenna replied, closing the door behind her and slowly approaching him.

Mr. Reed's heart raced as he realized she was serious, and here they were, alone in his classroom. He stood wordless and motionless.

"Well, did you?" Jenna asked.

"Uh...yes," Mr. Reed replied.

"So," Jenna said, now barely a foot away from him. "What do you think?"

"We can't Jenna," Mr. Reed pleaded, seemingly trying to convince himself as much as her. By now his cock had grown hard.

"Why not?"

"I'm your teacher," he reasoned.

"I'm an adult. And I know what I want," she said, reaching out and feeling the visible bulge in Mr. Reed's trousers.

"Please, Jenna," he said, catching his breath and stepping away from her, hardly able to believe she had just touched his throbbing boner through his pants.

"You know you want this," she said, looking over her shoulder at him as she bent over his desk.

She wasn't wrong. He watched, transfixed, as she reached a hand behind her ass, pushed her panties aside, and began fingering her wet pussy. Right here in his classroom, this devastatingly beautiful 18-year old was fingering herself.

Mr. Reed knew he had probably already overstepped a line by not kicking her out of the classroom right away, and certainly had now he was watching her masturbate over his desk. He couldn't resist any longer. He was overcome with lust and gave into temptation.

He approached her and Jenna anticipated him freeing his hard member and entering her, but instead he got on his knees behind her and pulled her panties aside. He put his mouth on her dripping wet snatch and began munching on it feverishly. He had completely forgotten his qualms about his doing this and ate her out as he if he hadn't eaten in days. She tasted so good, kind of sweet, and his cock began to leak precum.

"Oh Mr. Reed that feels so good," Jenna moaned, and it really did. He licked her pussy lips, inside her, as well as her engorged clit.

Feeling adventurous, he did something he had never done before but suddenly couldn't help himself. He replaced his mouth on Jenna's pussy with his fingers, to Jenna's initial disappointment, but made his way with his tongue to her asshole. He licked it gingerly at first, fingering her sopping wet cunt as he did, but grew bolder and was soon spreading her ass cheeks and probing her forbidden hole with his tongue, deeper and deeper.

"Oh my God that's amazing," Jenna moaned as Mr. Reed lapped at her puckered asshole. Nobody had ever eaten her ass before.

Mr. Reed's cock somehow seemed to grow even harder and he had to use one hand to undo his pants and free it before it tore a hole in his crotch.

"Oh fuck Mr. Reed," Jenna moaned again as he massaged her clit while munching on her asshole. "I'm gonna...I'm gonna cum!"

Mr. Reed increased the intensity of his licking and fingering, and before long Jenna was in the throes of climax.

"I'm cumming...," she groaned. "Fuuuuuuck..."

Pleasure like she'd never felt before coursed through her veins, in every part of her body. Juices dripped from her twat and down her thighs as her orgasm built and built, making her shudder and squirm, and cry out in ecstasy. Finally it subsided enough for Jenna to speak.

"I need you inside me now," Jenna panted. "Put it anywhere you want!"

"Anywhere? You're sure?" an incredulous Mr. Reed asked.

"Anywhere," Jenna repeated, practically begging.

How could he pass up such an invitation? He placed the swollen head of his hard cock against her anus, and slowly began to push it past her sphincter.

Jenna moaned as he entered her. This was her first time having anal sex, and she responded with a mixture of pleasure and pain as inch by inch he slid the entire length of his cock inside her ass. Her orgasm still reverberated through her body, which helped overshadow some of the pain should might have otherwise felt at being fucked up the ass for the first time.

"I've never done this before," Jenna said, whimpering.

"You haven't?" Mr. Reed said, slowly starting to slide his meat in and out of her asshole. Knowing he was taking Jenna's anal virginity only made it feel better. And it already felt incredible. He had never felt anything as tight and yet pleasurable around his cock before.

"Oh Jenna," he moaned, over and over, almost like a mantra he couldn't help himself from repeating, as her rectum squeezed his throbbing cock.

He pushed it in further each time, slowly, and it was so tight he didn't think he'd be able to go any faster even if he wanted to. It felt so good he knew he wasn't going to last long. And about 30 seconds later, he was proven right as he felt that familiar tightening in his balls and shaft.

"Oh Jenna...Oh Jenna...I'm gonna cum," Mr. Reed moaned as he neared climax.

"I wanna feel your cum inside me," Jenna pleaded, and that was enough to send him over the edge.

"Here it comes," he said, panting, and then a couple of seconds later it happened. He grunted over and over again as he cock twitched and spasmed, spraying an incredible amount of hot jizz deep inside Jenna's rectal cavity. It felt unbelievable to nut inside Jenna after fucking her ass, and he felt like he'd never cum so much or intensely in his life.

"Mmmmm," Jenna moaned as she felt her teacher's cum filling her ass.

Just then, as jets of spunk continued to fill Jenna's rectum, they were horrified to learn they were not alone.

"Well, well, what have we here?" someone said, and Mr. Reed thought he recognized the voice. He turned, his cock still visibly up Jenna's asshole, and his suspicion was confirmed. And it could not have been any worse.

It was Principal Brooks, the school principal. He was in his mid 60s, tall with an atheltic build with broad shoulders. He had silently entered the room 20 seconds previously and watched as one of his teachers sodomized and ejaculated inside one of his students.

"Principal Brooks, I, I...," Mr. Reed stammered as he withdrew his meat from Jenna's asshole, too shocked to form a coherent sentence. And what would have said anyway? That it wasn't how it looked?

"Oh my God," Jenna said as she heard who had caught them. She pulled her panties up and patted her skirt down. Semen leaked out of her asshole and into her panties.

"You what, Mr. Reed?" Principal Brooks asked.

"I...I'm sorry," was all Mr. Reed could muster as he turned away, pulling his trousers up and putting his cock away.

"Please, I'll do anything you want, just don't fire him!" Jenna pleaded.

"Mr. Reed, you can go. And count yourself very lucky I'm in a generous mood," Principal Brooks said.

Mr. Reed and Jenna exchanged a rather bemused look, and then Mr. Reed hurried out the door before Principal Brooks changed his mind.

"So you said you'd do anything," Principal Brooks said a few seconds after the door shut.

"Yeah, anything at all," Jenna replied.

"Well let's see if you mean it," Principal Brooks said, approaching Jenna.

When he reached her at the desk, he shocked her by putting his left hand down Jenna's panties and sliding a finger inside her dripping wet snatch, eliciting a moan from Jenna.

"Mmmm, nice and wet," he whispered in her ear, while he grabbed and squeezed her left breast with his right hand.

Jenna couldn't believe this was happening. She had instigated what happened with Mr. Reed, but now her principal was the one initiating the contact, and he now had two fingers deep inside her cunt. What shocked her just as much was that, as hard as it was to admit it, she actually liked it. A lot. She had pursued Mr. Reed but now she was taking a submissive role, and it was such a turn-on.

After a few seconds of fingering and groping her, Principal Brooks stopped and began unzipping his pants.

"Get on your knees," Principal Brooks said, an urgency in his voice.

"Yes sir," Jenna replied, embracing her new-found submissiveness.

By the time her knees met the classroom floor, Principal Brooks' cock was free and fully erect. It was big, maybe bigger than any cock Jenna had seen.

"Open your mouth," Principal Brooks said as he put his hand on the back of her head. Jenna took a deep breath and did as she was told.

Principal Brooks slid his thick cock past her lips and along her tongue, into her warm, wet mouth. The feeling was unbelievable and he groaned with pleasure as his member was engulfed by Jenna's mouth.

This was of course not Jenna's first experiencing performing oral sex, and she put her cocksucking skills to use, giving Principal Brooks by far the best blowjob he had ever. Long and slow she sucked, no hands, all mouth.

"Look at me," Principal Brooks said, and she obliged, looking up at him and maintaining eye contact while she sucked his cock.

Then he pulled her head closer to him, forcing her to deepthroat his cock. Her eyes watered and saliva spilled out of her mouth. She had to hold his legs to steady herself.

"That's it, take all of it," he commanded as he forced the entire length of his shaft into her mouth.

Jenna gagged and he withdrew his cock, allowing her to breathe. But seconds later he reinserted it and again pushed it to the back of her throat, and Jenna offered no resistance.

"Oh yes," he moaned. "Deepthroat my cock you filthy fucking bitch."

With both hands on her head, he then began thrusting his hips forward, his cock pistoning in and out of Jenna's helpless mouth.

"You cockteasing little whore," he growled as he relentlessly fucked her face, his balls slapping against her chin.

After about 30 seconds of mouthfucking her, Principal Brooks withdrew his cock from Jenna's mouth, a thick trail of saliva linking them. Jenna gasped for air.

"Get up," Principal Brooks said, grabbing her right arm and picking her up and pushing her onto the desk, facing away from him.

He lifted her skirt and yanked her panties down her legs to her knees. She felt the palm of his left hand come down hard on her left ass cheek. And again, and again. He slapped her ass, over and over. Her principal was spanking her, and it felt so good. Her pussy ached as he continued spanking her ass, both cheeks, until it was pink.

Principal Brooks couldn't wait any longer to enter her, and he had no hesitation about which hole he was going to use. With his right hand, he guided his thick, throbbing member towards Jenna's ass, and she gasped as she felt his cockhead bump up against her asshole.

"Was he gentle with you?" he whispered in her ear.

"Kinda," Jenna replied.

"I"m not going to be," Principal Brooks said. "I know you like it hard and rough, don't you?"

"Yes sir," Jenna said reluctantly but almost involuntarily.

And with that he pushed the head of his cock past Jenna's sphincter, eliciting a cry of pain from Jenna. Maybe it was because Principal Brooks' cock was bigger, maybe it was because he inserted his cock more quickly, but this was definitely more painful than when Mr. Reed had fucked her up the ass earlier.

"Oh my God you're so fucking tight," Principal Brooks moaned.

Seconds later he had shoved the entire length of the biggest cock Jenna had ever seen up her hot, tight, anal cavity. The pleasure Principal Brooks felt as her ass gripped his cock was immense, while the pain for Jenna was almost unbearable and she continued to moan.

Her groans and whimpers only grew louder as Principal Brooks began to thrust his cock hard and deep up her ass. He wasn't joking about fucking her roughly, and slapped her ass again as he sodomized the 18-year old.

"You love this don't you, you filthy slut?" he whispered in her ear, after grabbing her hair and pulling her back towards him.

"Yes sir," she said, hiding her intense discomfort, but it wasn't exactly a lie. This was all part of her submitting to him, so part of her was enjoying it.

As the frequency and volume of Jenna's cries and moans increased the harder he fucked her, he was concerned someone might hear, so he covered her mouth with his left hand, while still gripping her hair with his right.

"Fucking take it you nasty anal whore," he growled.

She hadn't had anal sex before barely 30 minutes ago, and now she'd been sodomized by her math teacher and principal, over the same desk.

Principal Brooks knew he wasn't going to last long, so slowed the pace of his thrusts, much to Jenna's relief. But only 30 seconds later, he realized he was extremely close to climaxing, and he had already decided where to cum. He was about to realize a long-held fantasy.