The Adventures of Jenny

Note: All of the characters in this story are at least 18-years-old.

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Prologue

Jenny was once a usual, rather innocent high school girl though she looked anything but. Standing at 5 foot 2 inches, she had long red hair down to her cute bubble butt, green eyes, and DD tits. She looked like a wet dream and she knew it. But she was actually a nice girl.

She had tried dating some of the guys at her school, but they all just wanted to get in her pants. It wasn't until her senior year that she met Steve. Steve was 5 foot, 10 inches with short brown hair. He was an honor student and actually treated Jenny with respect. No one understood why she had turned down so many other guys to end up with Steve, but she saw something in him.

Their relationship started out innocent. He was her first kiss and she was his. He would take her out to nice places and did everything he could to make her feel special. However, Steve was still a teenage boy. Jenny knew the effect she had on every straight male with a pulse so she accepted it when their relationship gradually became physical. Well, to a point she did.

She knew that Steve wanted to fuck her. She recognized the hungry look he would get when they would make out in the back of his car. And while she had never let anyone else go that far with her, she knew what the bulge in his pants meant. The problem was that her father had filled her head with horror stories about sex. How the first time hurt, the risk of pregnancy, STDs, etc. So, she resisted having sex with Steve as best as she could.

One thing she did to protect her virginity was learn to suck his cock. One of her more experienced friends showed her how with a dildo and the next night, she surprised Steve with her newfound skill.

That night, she learned a few things. First, she was surprised that Steve's cock at 5 inches was smaller than the dildo she had practiced on, but she assumed the dildo was just really big. Secondly, she learned that she could make Steve do anything she wanted as long as she would blow him. Thirdly, she learned that she actually liked sucking cock, especially when Steve would blow his load down her throat. It made her so very wet that she started masturbating while she sucked him off.

This arrangement lasted for a few weeks. Then, at prom night, Steve rented a hotel room so that they could have an actual bed to fool around in for once. He said he didn't expect to get laid just because it was prom night, but he had a surprise for her this time. After she sucked his cock, he pushed her on her back, spread her legs, and ate her pussy for the first time. Steve had never touched her there before and while he had no experience, his enthusiastic pussy eating got the job done and made her cum hard. In her post orgasmic state, her cum addled brain momentarily forgot her fear of losing her virginity which led to Steve plowing her virgin pussy while she wrapped her arms and legs around him. It was an amazing five minutes. But then, Steve moaned loudly and blew his load inside her. When she realized what he had just done, her fears returned and she freaked out. He ended up having to take her home and she wouldn't speak to him for a week.

Luckily, Jenny didn't get pregnant and she eventually forgave Steve on the condition that he would use condoms from now on. She couldn't deny that she enjoyed having sex with him. While he would always cum before she could, he would eat her out till she did. So, she was happy.

But all of that changed one day in Jenny's math class.

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Chapter 1-The Teacher

Mr. C, Jenny's math teacher, was passing out the mid-terms her class has taken Friday. Math wasn't one of Jenny's strong suits, but she usually could make due. So, when Mr. C laid her paper face down on her desk, she was shocked to find she had made an F! The test had been hard, but she had never actually failed one of Mr. C's tests before. And being a mid-term, this would seriously impact her grade!

Mr. C's class was the last math class Jenny needed to graduate. It was almost her only required class left. Failing this mid-term meant that she was now just barely passing this class and if she failed another test, she might not graduate on time. Her boyfriend Steve already had an early acceptance to UNC-Chapel Hill and she had planned on joining him. But to do so, she needed at least a B in Mr. C's class if not an A. And now, she had a D. A C at best!

After school was over, she told Steve that she was going to talk to Mr. C about her grade and she would give him a call when she was done. She was dressed in a red t-shirt that strained against her DD tits and a jean skirt that ended just above her knees. She knew she had the body of a slut but didn't intentionally show it off.

She stood outside Mr. C's classroom and knocked at the door. "Come in," she heard him say from inside.

As she entered the room, she saw Mr. C sitting at his desk working on tomorrow's lesson. Standing at 5 foot 8 inches, Mr. C was an overweight black man in his 30s. But when she wasn't fearing about her future, she would admit that he was really cute. He was light-skinned with short, dark brown hair and hazel eyes. Today, he was dressed in a white button-down shirt and grey pants.

"What can I do for you, Jenny?"

"Well, Mr. C, about my mid-term..."

"Yes, I was quite disappointed in you, Jenny."

"I'm rather disappointed myself... But is there anyway I can pull my grade up? I need at least a B in this class."

"Honestly, it would be very hard to get your grade back to a B. And I'm not sure you have the ability."

"But Mr. C! I can't get into Carolina if I get a bad grade in your class!"

"I'm sorry, but I'm not sure what can be done."

"Please, Mr. C! I'll do anything!"

"Anything?" She didn't notice the sly grin that was starting to form on Mr. C's face.

"Yes, anything!"

Mr. C got up, walked to the door, and locked it. Then, as he turned back to Jenny, he somehow looked far more intimidating that he ever had before. "Then take off your shirt."

"My...what?"

"Your shirt. I've been wanting to see those big tits of yours since I first saw you."

That's when it hit her. She had fallen into his trap! And yet, she knew she couldn't prove that he had failed her on purpose. It would be her word against his and he was an established teacher here. With trembling hands, she grabbed the bottom of her t-shirt and lifted it up and over her head. And that's when she remembered she was wearing a cute, lacy pink bra that clasped in the front in preparation for her date with Steve that night.

"Very nice!" Mr. C immediately unclasped her bra and let it drop, exposing her large tits. "Very nice indeed!" He started to grope her tits, squeezing them and pinching her nipples. Her breasts were sensitive and she loved having them played with, so when he put a nipple into his mouth and sucked on it, she couldn't stifle the moan of pleasure that escaped her lips.

After spending a few minutes sucking on and groping her breasts, Mr. C said, "Now, get on your knees, Jenny." Jenny did as she was told and was now eye level with the bulge in his pants. She knew what would happen next.

"If-if I suck you, you'll raise my grade?" Jenny asked nervously.

"Of course," Mr. C replied as he reached for his zipper.

Jenny knew she was an expert cock sucker and while this would be the first cock other than Steve's she had sucked, she was confident that she could give Mr. C a mind blowing blowjob and be done with this. At least, that's what she thought before he unzipped his pants and whipped out his cock.

"Oh my god!" His cock was so big! And brown! It was maybe twice as long as Steve's and a lot thicker. He was easily as long as the dildo she had learned how to suck cock with.

"What's wrong, Jenny?" Mr. C asked with a smirk.

"N-nothing. It's just...so...big!"

"Why thank you. Now, get to work, slut."

Jenny wrapped her delicate right hand around Mr. C's cock and started to jack it slowly. Her hand couldn't quite close around it. While she was certainly frightened, she was also mesmerized by this big, black cock. She was determined to suck it.

First, she kissed the head. Then, she licked his cock up and down. "That feels good, baby. Now, put it in your mouth." She took a deep breath and then opened her mouth wide to take in the head of his cock. She sucked on the head causing Mr. C to moan. Then, she worked about a third of his cock into her mouth. She bobbed her head back and forth on his cock as she sucked gradually working more of his cock down her throat. Two-thirds of the way, she started to gag and had to back off a bit. But then, she started again and managed to swallow his entire cock. "Damn girl, you're a natural!"

That's when she knew she had him. She locked eyes with him and moaned on his cock. Then, she began to bob up and down. This always drove Steve crazy and he would soon blow his load down her throat.

But Mr. C wasn't Steve. As good a cocksucker as Jenny was turning out to be, he wouldn't cum that fast. After 5 minutes of this, Jenny's jaw was starting to get sore. Mr. C pulled his cock out of her mouth and put it between her tits. "Hold your tits together." Then he proceeded to fuck her tits. "Your big tits feel so soft and warm wrapped around my cock!" After a few minutes of this, he finally came. The first short blasted Jenny in the face and neck. Then, he shoved his cock back into her mouth and blew the rest of it. Instinctively, she swallowed his cum and sucked out the rest.

As she pulled away from his cock, she was surprised that while it had softened some, it hadn't gone down much. Then, next thing she knew, Mr. C picked her up and set her on his desk with her legs hanging off. "Mr. C, what are you-ooooh!" Mr. C reached between her legs and rubbed her pussy through her very wet panties.

"He he, you're drenched, Jenny! You must really love sucking my cock." Then, he spread her legs and pulled off her panties revealing her shaved pussy. "Now, this is a surprise!" After Steve had started eating her out, she started keeping her pussy shaved.

"This is getting out of control!" she thought frantically. Here she was half naked on her teacher's desk with her legs spread and her teacher's cum on her face. "I have to stop thi-" Just then, Mr. C shoved a finger into her dripping wet pussy and interrupted her train of thought. "Oh no!" she thought as he knelt down in front of her and slowly licked her pussy. Coherent thought became harder and harder as he eat and fingered her pussy. He was far better at this than Steve. She was powerless to resist even as her last coherent thought was remembering what happened the last time she was in this position. But even that thought was obliterated by the powerful orgasm that Mr. C brought her to.

As she lay their panting hard in post-orgasmic bliss, she didn't notice at first when Mr. C rubbed the head of his once again hard cock against her slit, lubing it up. And then with one, hard thrust, he shoved his big cock inside her tight, teenage pussy causing her to gasp loudly. Half of his cock was deforming the part of her pussy that was molded around Steve's cock while the other half was forced into virgin territory. "God DAMN, you're tight!" He held her down and started to pound her fast and hard causing her big tits to bounce. Her brain at this point was far too broken to think of anything besides how amazing this big black cock felt inside her. All that came out of her mouth were incoherent sounds, moans, and screams until finally, she came loudly with an even bigger orgasm than before.

Mr. C then pulled out of her, turned her around so that she was bending over his desk, pulled her skirt all the way down, and slammed his cock back into her pussy. With his right hand, he grabbed a fist full of her long hair. With his left, he grabbed one of her hanging tits. Then, he proceeded to fuck her stupid, again. "Jenny, your tight pussy is too much for me. I can't last much longer, so I'm going to fill you up with my baby batter!"

This caused her brain to at least partially spark back up and she realized this big cock that was far deeper inside her than Steve ever was about to drop a huge load into her unprotected womb. "No, Mr. C! Please don't cum in me! I'm not safe!" Still, she was powerless to stop him, her body having completely submitted to the powerful fucking she was getting. And the third orgasm of the night that was rapidly approaching.

Luckily for her, Mr. C didn't want to knock her up, so he did pull out at the last instant, cumming on her ass and back. Then, she collapsed from her own orgasm leaving her a shaking, cum covered mess on the floor.

She didn't understand what was happening when he pulled her up on her knees and shoved his cock back into her mouth but she sucked him instinctively. She didn't understand what was happening when he sat her on his desk again. Then, he pulled a bottle of lube out of his desk and coated his fingers with it. "Jenny, you've been an amazing fuck, but you do want that A, don't you?"

"Uh huh..."

Mr. C then pulled Jenny forward so that her ass was hanging off of the desk, found her asshole with his finger, and slowly pushed it in. "Wha...?" Jenny's scrambled brain could barely recognize that this was something different.

"Relax, Jenny. Just relax." She wasn't exactly capable of putting up much resistance at this point anyway, but his voice made her relax as he slowly fingered her asshole. It felt weird, but was starting to feel good causing her to moan. Then, he worked two fingers into her ass. She still didn't understand what he was doing but she liked it. Finally, he pulled his fingers out of her ass and started to lube up his cock.

"As tight as your ass feels, I take it you've never had anything put up there, right?"

"Huh...?" And then, she felt the head of his cock pushing at her asshole.

"Relax, Jenny. Just relax." Then, he popped the head of his cock into her virgin asshole.

"OH!" This caused her to regain more consciousness. "Oh god, you're in my ass!"

"You want that A, don't you? Well, 'A' stands for 'Anal'!" Then, he started to slowly push more of his cock up her asshole.

His big cock was painfully stretching her asshole wide open. And she was terrified that he would do to her ass what he did to her pussy. While she had enjoyed every second of the brutal fucking he gave her, she knew her virgin asshole would be torn to shreds by that.

However...she needed that A. And his cock was already penetrating her ass so she had already lost that virginity. Having gone this far, she might as well keep going. So, she willed her sphincter to relax around its large intruder allowing Mr. C to bottom out in her ass.

Then, he surprised her by gently rubbing her clit. His cock was balls deep in her ass, but he wasn't moving. Instead, he was letting her get used to having him inside her ass. And as he rubbed her love button, the pain started to fade away.

"Just relax, Jenny. I want this to feel good for you." Then, he slowly pulled his cock nearly all the way out of her ass and then slide it back in. As he fucked her ass with slow, long strokes, the pain began to be replaced with pleasure.

"Uuuuhhh, Mr. C!" The pleasurable feeling in her ass began to increase and the pain was gone completely. "Fuck my ass, Mr. C!" She could hardly believe herself as she said that. Her teacher was sodomizing her and she not only was enjoying it but she was encouraging him! Mr. C picked up speed and began to thrust with more force. "Uh! Uh! Fuck me! Fuck my ass!"

Mr. C kept gradually increasing his speed until he was going just as fast in her ass as he was in her pussy. And she loved every minute of it. Then finally, she screamed loudly as her whole body shook with a massive orgasm.

Mr. C pulled out of her ass, sat her on her knees on the floor, and shoved his cock back into her mouth. The conscious part of her brain realized that she was tasting her own ass as she sucked his cock but the lewdness of it turned her on even more. Then, he pulled her up by her hair and bent her over his desk again. But before he mounted her again, he started spanking her ass hard. "You're a dirty little ass slut, aren't you?"

"Yes!"

"Say it!"

"I'm a dirty little ass slut!" Then he shoved his cock back up her asshole and began to pound her hard. "Fuck, fuck, FUCK!"

"This time, I'm going to cum inside you, little whore!" Her mind was broken by his hard fucking yet again, but one thought that made it through was that she WANTED him to fill her ass with his cum.

Finally, with one last hard, deep thrust, Mr. C practicaly growled as he blew his load deep in her ass, which set off yet another massive orgasm for her as well. For awhile, he rested on top of her with his cock still buried in her ass. Then, he slowly pulled out and watched as a stream of his cum poured out of her ass. He wiped a finger through the cum and walked around to the other side of his desk. "Well Jenny, you certainly earned that A. I'll write it right here." With his cum covered finger, he drew an 'A' on her forehead. "Now, you'd better get going. I still need to finish preparing for tomorrow."

With very unstable legs, she managed to dress herself and walk to her car. They had fucked for over an hour, so there wasn't many people left at school. Still, she was careful to not let anyone get a good look at her. She knew the 'A' on her forehead wouldn't be visible unless you got right up on her, but she felt like it was her very own scarlet letter.

When she got home, she was grateful her parents were out of town and therefore no risk of them seeing her like this. Her hair disheveled, cum on her face, and cum leaking out of her ass, she thought she looked as much of a whore as she felt.

She quickly called Steve and told him that she wasn't feeling well to break off their date. Then, she got in the shower to clean up. She felt ashamed at what she had done. And yet, she couldn't help but touch herself as she thought about it. She rubbed her pussy thinking about Mr. C's big cock stretching it. She knew that she would never be satisfied with Steve's cock again. Then, she slowly reached behind her and worked a finger into her cum filled asshole. Mr. C had caused some permanent changes in her both physically and mentally. She had been introduced to anal sex and now she craved it. And she had been introduced to big, black cocks and she craved them, too. Or was it just big cocks? Do white guys get that big? As she fingered herself to orgasm, she knew that she would have to find out.