(S)extending the Curriculum

bynikki_2021©

This story was written by request so its not entirely exactly what I would normally choose to write myself, but having completed it, I thought that I'd share it with you all anyway.

Nikki

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All characters in this story are over 18 years of age

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"Are you kidding me? The woman is a fucking Nazi," Daniel exclaimed.

"So you're telling me you wouldn't give her one if you had the chance?" Pete challenged him.

"Oh I agree she's hot enough, but I just can't imagine ever actually doing it," Daniel replied.

"She's working class," Joe added to the conversation, espousing his so-called inside information that they'd all heard before. "Apparently she busted her ass to get where she is and likes to take it out on all us bright young men."

"Bright young men?" Pete asked with a laugh. "You mean spoilt little rich kids?"

"Yeah, well I prefer being a bright young man myself," Joe said.

"It could explain why she's such a bitch," Daniel replied.

"I for one would still like to show her a good time," Pete said wistfully.

"She'd chew you up and spit you out," Edward joined in with.

"What a way to go though, crushed between those tits," Pete dreamed aloud.

"Or her between her thighs," Daniel suggested.

"She's old enough to be your mother you realise?" Edward suggested.

"I'm not looking to marry her," Pete replied with a laugh, "I just want to empty my sack in her or all over her. I mean shit, none of our mothers are anywhere near as hot as she is. I'd love to have her cooking my dinner!"

"Your mother doesn't cook your dinner anyway!" Daniel accused him.

The sound of the school bell ringing startled them all back to reality.

"Damn, now that's all I'm going to be able to think about all through History," Joe complained. "Especially if she's dressed in one of those tight skirt and blouse outfits."

The four friends gathered their things and headed off to class, tossing the rubbish from their lunch into a trash can on the way.

Pete was almost salivating. He didn't do well in history (mind you he didn't really try very hard either) but he enjoyed the subject if for no other reason than for Ms. Masters being the teacher. Even before he made it to the class room he was picturing her body. Stacked was one way to think of it. Big round tits, a large, firm ass, almost always packed into tight clothing that showed it off beautifully. It had to be deliberate. There's no way she couldn't know what it did to the impressionable (or outrageous) minds of the final year students that she taught history. He wondered if maybe she thought that the guys would be more controllable if her body distracted them. It probably didn't help their grades though given most of them weren't likely to be concentrating on the actual subject matter.

"You still with us?" Joe asked and punched him playfully in the shoulder as they entered Elding Hall.

"Sorry, distracted," Pete replied.

"No shit Sherlock," Daniel said with a laugh.

"Day dreaming about big tits with a load of cum all over them?" Edward suggested.

"Something like that."

They turned from the hall into the classroom and took their usual seats, halfway to the back of the class on far side of the room from the windows. They'd learned early that sitting in the back row drew too much attention and so had shifted around until they were happy with their seats. It was Pete that had first noted that sitting on the opposite side from the windows provided some amazing views as their teacher moved about the room. The girls in the class tended to take up the front row and the true slackers sat at the back and didn't seem to mind that it was a red flag to the teacher to watch out for them.

In other classes it wasn't as much as an issue, but with Ms. Masters, the last thing you wanted was to give her a reason to get upset. She was a stickler for the rules, quick to anger and even quicker to take action. It was rare that someone from the back row didn't end up with detention or a visit to the principal's office.

"Books open," Ms. Masters stated matter-of-factly as she entered the class room. Almost instantly the sound in the room changed from subdued casual chatter to that of paper rustling as books were opened ready for the lesson (they all knew by now that any sort of significant carry on whilst waiting for her to arrive was dealt with as harshly as any true infraction in the class room).

Pete belatedly grabbed his book and opened it, startled from the view that he'd been enjoying. Ms. Masters was wearing a lemon coloured blouse and black pencil skirt. The skirt hugged her ample hips and generous ass and the high waist line pulled her blouse in beneath her big tits. His eyes moved down over her legs, impressed by the shape of her calves, accentuated by the four inch heels that she wore to boost her short stature. He stared at her ass until she started to turn back toward his side of the room. He quickly snapped his eyes to his book.

Ms. Masters had just started to teach when a phone rang. All other noise instantly stopped, only serving to highlight the strains of some pop song that was vaguely familiar to Pete, though not familiar enough that he could name it. The silence was pregnant with expectation. They'd all learned early on to shut their phones off. Having one ring was definitely a red flag.

"Shit!" Holly Wells hissed as she seized her bag to silence her phone.

"Ms. Wells," Ms. Masters said in the crisp, slightly English accent that Joe always claimed was put on to make up for her working class background.

"Sorry Ms." I was expecting a call from Mother called during lunch and hadn't turned it off.

"Excuses," the teacher stated flatly. "Phone on my desk, collect your detention slip at the end of class."

It was a sign of just how often it had happened before that no one in the class expressed any sort of surprise or indignation at the announcement. Even Holly silently accepted the punishment, walking to the front of the class to deposit her belatedly muted phone on the teacher's desk. Pete noticed a number of the boys watching Holly. She was on the cheer squad and one of the hottest girls in school. She didn't hold a candle to Ms. Masters as far as Pete was concerned though. He sighed as he once again wondered what it would be like to get to fuck his teacher.

"Do we have a problem Mr. Irwin?" Ms. Masters asked accusingly, advancing on him from across the room. Even his fright/flight response wasn't quick enough to distract him from noticing the brief silhouette through her blouse that the light from the window provided. Self-preservation helped him recover quickly.

"No Ms, not at all," he said quickly.

She didn't say anything further. She simply went back to teaching the class as Holly took her seat and Pete thanked his stars she wasn't in a worse mood.

"Dude I thought you were going to get hammered," Joe laughed as they discussed his near miss after class on the way to their final lesson of the day.

"No kidding, I was kind of distracted," Pete replied.

"Well she was looking fucking hot today," Edward said.

"Not as hot as Holly though," Daniel suggested.

"Are you kidding? She looked way hotter than Holly," Pete replied, disbelief bleeding through the tone of his voice.

"Only if you're into big older chicks," Daniel said with a shake of his head.

"Whatever dude. You can join every other guy in the school who's had a piece of Holly and I'll stick to the older, experienced, sexy as fuck teacher," Pete replied.

"Holly may be easy, but at least she's attainable," Daniel countered.

"Oh I'm sure with a bit of effort I could bang Ms. Masters."

"Dude, are you going to put money on that?" Joe asked.

"Maybe I should," Pete mused aloud.

"Dude if you nail that piece of ass I'll pay you a hundred bucks," Daniel offered.

"Deal," Pete replied.

"You're crazy," Joe laughed.

"No he's not," Edward noted, "He didn't say he'd pay anything if he didn't nail her."

"Fuck," Daniel stated.

Pete just laughed at him and they headed into their final lesson.

~~~~~

Pete sat in his room and considered his options. He wondered if he'd be able to seduce his teacher. He didn't really expect so. After all, she was such a stickler for the rules that he doubted she'd do something as crazy as put her job on the line for a bit of sex. Fortunately for Pete, he had means other than his charms to help him achieve his goals. His father had been very generous on his 18th birthday.

He lay back on his bed and day-dreamed about what it would be like to undress Ms. Masters. He imagined unbuttoning her blouse and the way it might spring away from those massive tits. He thought about bending her over her teaching desk and pushing her skirt up. He wondered what underwear he'd find. Would it be practical or sexy? He could argue both ways. She was a very practical person, but the way she showed off her figure left the possibility open that she'd be hiding a little something under her skirt.

His hand found his cock and he stroked it idly, feeling it stiffen in his grip as his imagination fuelled his fire.

It wasn't long until he had to grab a wad of tissues to catch his cum. He groaned loudly, wishing that he could explode all over his teacher. He loved the thought of seeing his creamy white goo sliding down into her cavernous cleavage.

Plans started to form in his mind. Ideas solidified. He wondered if he could pull it off. Would she fall for it? Did he actually have big enough kahuna's to even put such a plan into action? The thought of taking a hundred off Daniel was appealing. He didn't need the money and it was like throwing away spare change for Daniel, but just the satisfaction would be enough incentive even if the sex hadn't been (and it sure as hell was).

He decided not to say anything about it to his friends. What they didn't know they couldn't ruin for him. As his father always told him, one person best keeps a secret. He even backed off talking about their teacher for once, but that sent the wrong message. His friends were suspicious, so his silence didn't last long. He limited it to talking about how hot she'd dressed for particular lessons or to theorising what her favourite position might be (he claimed doggy while the others insisted that she'd like to be on top and in control. Edward suggested that if he pursued her to have sex he'd likely ended up on the end of her strap-on). Pete never mentioned his plan and he didn't get carried away. He waited a full week before he even put any of it into action.

He waited after school one day and claimed that he had some stuff that he needed to attend to so that none of his mates would hang around and wait for him. He waited outside Ms. Masters' office, alternately stepping nervously from foot to foot or leaning against the wall in feigned nonchalance until she arrived.

"Mr. Irwin," she said by way of greeting as she finally approached down the corridor, a stack of paper and books clutched to her chest.

"Hi Ms. Masters, I was wondering if you could spare me a minute or two?" Pete asked and quickly moved to stand almost at attention as she closed the last of the space. He fought to keep his eyes from sweeping over her body, thankful that the papers and books hid her luscious breasts from view and therefore removed the temptation to stare.

"Certainly, come on in," she said, awkwardly juggling the paper to open the door. She lead the way in and Pete followed her, mentally chastising himself when his eyes slipped down to the view of her shapely ass. He dragged his eyes back up and sat down in the visitor's chair.

"What can I do for you Mr. Irwin?" his history teacher asked as she sat.

"Well as you know, I'm not really doing particularly well in History at the moment and I was wondering if perhaps I could get some extra help?" The look that she gave him wasn't quite as promising as he'd hoped. Thoughtful, suspicious perhaps, but certainly not excited or in any way encouraging.

"Forgive me my skepticism Mr. Irwin, but I have to ask why now? From what I have seen, you've been happy to cruise through my class without making any particular effort nor perhaps even really caring about the class or your grade."

Pete swallowed his natural instinct to respond in a condescending manner, to try and put the teacher in her place. He decided that a mix of honesty and lie would serve his interests best.

"You're kind of right Ms. Masters, I haven't been all that invested in the class. I guess I picked history because it was mildly interesting and didn't seem all that hard. The reality is that when I finish school, I'll go to pretty much whatever college my father decides he's willing to donate money to, likely his alma mater and so my grades didn't really need to be all that stellar. He could see her fighting to keep from saying something and had a brief realisation as to just how bad that might sound to someone who had had to work hard to achieve everything that they'd managed in life. "Anyway, it turns out that father has decided that if I'm not learning at school then perhaps I'm not learning enough life lessons either, so he's put my college funding under threat against achieving certain standards. History is the weak link in my potential success. So I need help and I was hoping that you could be the one to help me."

"How very interesting," his teacher responded. "I can't really say that I approve of your reasons for being here, but at least you're actually seeking help. My question is this: Why me and not someone external?"

"Well you know the course and grade half my work and stuff, so who better? I mean, someone else might know the syllabus and stuff, but they won't have the same idea of what you're looking for when you're grading my work will they?"

"If I were to do this for you Mr. Irwin you need to understand that it would not be for any advantage over any other student. Don't come here expecting to sweet talk me into lifting your grade. You would have to work for it and I won't be at your beck and call as my time is limited. You may in fact find that a private tutor with the capacity to dedicate time to your cause would serve you better. In fact, to be honest, I think that is your best course of action. Why don't you think about it and get back to me tomorrow."

"I really don't need to Ms. Masters, I'd really like your help please."

"I tell you what Mr. Irwin, you show me what you're capable of over the next week and I'll give it further thought," she replied, her blue eyes boring into his in a challenge to his sincerity.

Pete bit back his protest along with the thought of offering money. He realised that he'd been extended the opportunity that he needed and decided that he'd probably be better served by taking it rather than trying to bully his way past it. That option would always be available later.

~~~~~~~

For the next week Pete worked his ass off in his history class. He spent his time working and listening and resisted his desire to sit and ponder what he'd like to do to his teacher's body. HIs friends noticed and gave him shit about it the entire time.

"So is this how you plan to get into Ms. Masters' Spanx?" Joe teased him during one of their lunch breaks.

"Spanx?" Pete asked.

"Yeah, you know, old-lady control briefs," Joe replied.

"I know what they are, I just can't believe that you'd think she wears them. I personally reckon that she wears thongs."

"Thongs?" Edward laughed, "Dude if she wore a thong that ass would swallow the poor thing whole."

"Dude, you're insulting the future recipient of my sperm," Pete responded.

"Cheekies I reckon," Daniel added to the conversation around a mouthful of sandwich.

"What the fuck are cheekies?" Joe asked with a laugh.

"Don't you ever check out Victoria's Secret?" Daniel asked him. "They're like briefs, but they're cut so that they show off more ass. Fucking hot if you ask me."

"Well clearly you know you're ladies underwear," Edward said.

"He's probably wearing some right now," Joe joked.

"Anyway, back to the topic at hand, what's with the Mr. Try-hard act?" Daniel interrupted.

"I decided that I should do well in History," Pete replied as if it was a logical answer.

His friends continued to mock him and seemed to be on to the fact that it formed some part of his plan to navigate his way into Ms. Master's bed, but Pete remained firm and refused to admit it.

~~~~~~~

After a week of working hard and paying attention, Pete returned again to Ms. Masters' office.

"Come in," she said when she saw him loitering outside her door.

"Hi Ms. Masters, I was hoping that we could discuss tutoring again?" Pete said as he took a seat opposite her. He watched as she leaned forward, rested her elbows on her desk and steepled her fingers as she considered his question. The movement drew his gaze to her fingers, which then put her cleavage in direct line of sight. He snapped his eyes up to meet hers again.

"You know Mr. Irwin, I think if you continued to apply yourself as well as you have for the last week that you wouldn't actually need additional help. I think you'd be quite capable of lifting your grade on your own ability."

"I'd rather not leave it to chance Ms. Masters, can't you please help me?"

She hesitated before answering and Pete sweated through the delay. He was surprised to discover how much he actually cared about the success of his venture. Mostly because he saw his hopes of fucking her pinned to it.

"I will help you Mr. Iwrin, your willingness to improve your performance is encouraging. So for as long as you show the commitment, I'll help you out. I can spare you an hour after school on Wednesdays."

Pete ran through his schedule in his mind. "That would be awesome, thanks Ms. Masters.

"I expect you hear in my office immediately after last class Mr. Iwrin," don't be late.

"Here?" he asked lamely.

"Yes."

"Um, okay," Pete replied.

"Is there a problem with that?"

"No, I guess I just thought it might have been more comfortable somewhere other than school, you know, where people aren't likely to be interrupting or anything."

"It will be here Mr. Irwin." Pete knew that tone of voice. it usually meant that she was about three seconds from sending someone to the Principal's office.

"Yes Ms. Thank you Ms." he replied. She waved him away and he left her office. He was pleased, but not completely satisfied. Somehow, her office seemed like a less than likely place for him to be able to seduce or otherwise talk her into letting him sleep with her.

~~~~~~~

"You need to concentrate Mr. Irwin. 'History isn't math. You can't just learn how to do it and then repeat. You actually have to remember what happened and apply thought."

Pete sighed. It was his third session with Ms. Masters and although he was getting a better grasp of history (and even a B on his last paper, he didn't seem to be getting any closer to his ultimate goal. He dropped his gaze to her ever-present crevasse that was her cleavage. The seductive curve of her ample breast always drew his eye and then snared his gaze. He could just see the edge of a black bra beneath her navy-blue blouse. If only the top button would come off. He dreamed of being able to tear the shirt open to expose her better. Every night after their tutoring session he'd masturbate while trying to picture what she'd look like naked. He'd envision her tits, her large, generous ass. He'd wonder if she shaved her pussy and before long he'd cum hard, wishing he was coating or filling her body with his seed.

He wasn't prepared to play as long a game as the current path would require.

"You know what would help me concentrate Ms. Masters?"

"No, tell me," she replied, clearly skeptical.

"Not being in this office. I think I'd be a lot more productive and successful if we could do this away from school."

"Mr. Irwin," she said formally, "Even if I believed that, the school has rules that I don't intend to break that prevent me from having any sort of private contact with student outside of school hours.

"Rules? Didn't someone say that they're meant to be broken? If it makes you feel better we could enter into a financial arrangement, make it a professional service. Surely if you're being paid they can't worry about it?"

"Mr. Irwin, you may think that money is the answer to all of your problems, but I assure you its not the biggest motivator for everyone in the world."

"That's quite cute Ms. Masters, but I don't think its true. I think everyone has a price, especially people that don't have very much money to start with. I'm sure that there's a few nice things that you'd like to buy that your salary doesn't quite cover."

"You can stop right there Mr. Irwin," she said angrily. "This is officially over. You can leave my office right now and I will see you in class. And so that you're aware, yes, I will be reporting this to the Principal."

Pete met her gaze evenly. He was frustrated. Patience had failed him and now he'd fucked up. With an exercise of will that he hadn't realised he had, he calmly collected his things and packed his bag.

"This isn't over," he said.

"Yes it is Mr. Irwin, now leave."

Pete strode from her office, already plotting his next move. Time to call in a favour from father.

~~~~~~~

"I understand your objections Ms. Masters and I fully support them, but this is one of those moments in life where you have to make a choice and you may not like having to make it or even the result of that choice."

Vicky stared in disbelief at the Principal.

"But it goes against all the rules and everything Bob," she replied.

"Look, there are always exceptions made to rules. They get bent, moved, erased and broken all the time and where money is involved, not to mention the future of the school, that's when they get abused the most. It's not like you're being asked to do anything all that bad. A little off-property tutoring isn't exactly the end of the world. It wouldn't be the first time that it's happened by any strech of the imagination. Hell if more of these rich little brats went to this much trouble to learn we'd be in a far better place.

"You're saying that I should do it Bob?"

"Yes Ms. Masters. Tutor him, take his money, do something nice for yourself with it. You've notified us and so it is now a school-sanctioned activity, so you need not worry about your employment or the board. You're a great teacher Ms. Watson and a credit to this school. I'd hate to lose you over tutoring a student and helping to further his education."

"Can I have some time to think about it please?" Vicky replied, trying to process what she'd just been told.

"Of course you can and don't take this as a threat, because its not intended to be one, but please consider the downside of refusing. From a school perspective there would be no consequences, but if people start throwing money and influence around, well sometimes the board takes a more active interest in the running of the school than I'd like. Do you understand?"

"I do, thank you Bob."

~~~~~~~

"Mr. Irwin, could you please stay a moment after class?"

"Doomed," Joe hissed to his friend as he packed his bag to leave the lesson.

"Somehow I don't think so," Pete replied. He waited for everyone to file out of the classroom and took the time to eye off his teacher again while she was occupied packing her own things. As usual she was in a tight skirt and breast-hugging blouse. He loved her hour-glass figure. He nearly moaned aloud when she bent over to pick something from her desk. He lamented the fact that her skirt was too tight and just long enough to prevent her from exposing anything, but still liked the way the material hugged her womanly ass. As usual, he tried to determine what sort of panty-line it might reveal, but his departing classmates kept interrupting his view.

"So Mr. Irwin, I have been giving some further thought to your proposal to pay me for tutoring services. I have cleared it with the Principal and have decided to accept the offer."

"That's awesome," Pete replied, smiling up at her. Father had indeed come through for him.

"Yes, well that might not be quite how I'd put it, but that's how it is. So, did you have somewhere in mind as to where we will conduct these sessions?"

"Yeah, my house," Pete replied. "We can use my study. Of course, if I'm paying I think that I'm going to need two sessions per week so that I can be sure about getting that grade I need." He watched as she went to reply but bit back the response. He wondered what sort of leverage had been applied and how far he could take it. He decided to try patience again given what happened the last time he had been too presumptive.

"Very well then. Monday and Wednesday. Does that work for you Mr. Irwin?"

"That'd be great thanks Ms. Masters," Pete replied. He scribbled his address down on a piece of paper. He held it out for her so that she'd have to bend over to take it from him. He took full advantage of the view of her cleavage when she did.

~~~~~~~

Pete glanced around his study one final time to make sure that it was tidy. He'd hate for Ms. Watson to be left with the wrong impression. He peered out the window for what seemed like the thousandth time, but there was no sign of anyone at the gate. Satisfied that the room itself was up to standard he went into his adjoining bedroom and checked his appearance in the mirror. He hadn't dressed up or anything, but that was no reason to get caught out with messy hair or food in his teeth or something.

He was just turning away from the mirror when he heard the buzzer from the intercom. He went to the control panel by the front door and confirmed that it was Ms. Masters arriving. He buzzed her through the front gate and walked outside to meet her on the porch. Her little, functional Mazda rolled to a stop on the gravelled drive way. Pete walked around to the driver's side and as the engine died, opened the door for his teacher.

"Thank you Mr. Irwin," she said to him as she stepped from the car. The view down her cream blouse was priceless as she exited the vehicle. She was dressed as if for teaching, but the angle saw the blouse fall away from the generous swell of her breasts enough to show off a lacy white bra beneath. He quickly glanced away before he was busted for looking, determined to rebuild some trust before he pushed things in the direction that he planned.

"Nice house," Ms. Masters stated as she surveyed the frontage of the large, double-storied mansion.

"Its the only one I've ever lived in to be honest," Pete replied as he lead her to the front door.

"What does your father do?" his teacher asked him.

"He's in business. Property development mostly, but there's some manufacturing interests, as well. I think he sits on a couple of boards as well; schools and education based businesses mostly. He's pretty busy."

"Impressive. And are you 'heir to the empire?'"

"Not quite. I have an older brother and sister and they're headed in that direction. I'm not really sure what I want to do just yet, but if I want it, there's a place for me in the family company as long as I get through college."

"Well then, we should probably get working on hat history grade then, shouldn't we?"

Pete led his teacher into his study, enjoying the wide-eyed stares that she cast about the house. He guessed that the proportions were somewhat beyond what she was used to. He wondered what her living arrangements were. As his teacher took a seat and pulled teaching materials from her bag, Pete pulled the door to his bedroom closed. He saw her glance inside and was glad that he'd taken the time to tidy it up. The maid took care of most of it, but that didn't mean it was always perfect. He pushed down thoughts of what it would be like to have her face down on his bed, presenting her curvaceous ass to him and prepared himself to study. He was determined to get through at least four sessions without giving any hint of his ulterior motives.

"That went well Mr. Irwin," Ms. Masters said to him at the end of the session as he escorted her out.

"Do you think you could call me Pete?" he asked. "I mean, I get the school formality and all, but I really struggle with being called 'Mr. Irwin' here. I keep expecting to see my Father standing behind me."

"I'll give it some thought," she replied.

"Thanks for the help Ms. Masters," he said as he closed her car door for her. "I think its really going to help me."

"See you at school tomorrow Mr. Irwin."

~~~~~~~

As he'd promised himself, he managed to get through the next four sessions without doing anything more than appreciate his teacher's beauty with the occasional fantasy of MILF sex (even though he didn't actually know if she was a mother or not - she didn't wear a wedding or engagement ring which might have at least given a clue).

The end of the year approached though and he didn't want to leave his run too late. He wanted to nail her before he lost the opportunity. He'd decided that Monday's session would be the start of it. He adjusted his hardened cock as he thought about the possibilities.

~~~~~~~

Pete decided that it was time. He needed to see how far he would be able to push his teacher. He wanted to know what it would take. If there was one thing that his father had taught him through his business dealings it was that everyone had their price. It was just a matter of getting them to that price without things going to hell on you.

He checked his appearance in the mirror, making sure (as he did before each tutoring session) that he was suitably presentable to receive Ms. Masters. The chime to indicate that someone was at the front gate rang through the house and Pete made his way toward the door. The maid would buzz Ms. Masters through, but Pete liked to make sure that he was there to open the door for her when she pulled up.

He pulled open the door to the Mazda and held out a hand to assist her as she disembarked from the car.

"Thank you Peter," she said as she came to stand on her own. She'd refused to call him Pete. It had taken three sessions just to get her to stop calling him Mr. Irwin, but he'd eventually won that little battle. She claimed that the diminutive form of his name was just a step too familiar for her. He'd asked for permission to call her by her first name, but she'd cut him down at the very suggestion and it was pretty clear that it wasn't going to be a negotiation.

Pete escorted Ms. Masters to his study, letting her take the lead so that he could, as always, eye off her beautiful (and bountiful) ass. He found himself reaching with his hands, palms toward her as if to cup her butt. He snatched them back, knowing that even if he was willing to go through with it that it was too soon. He wondered if he'd ever be able to simply grab her whenever he wanted, or whether as he suspected, it would only be under sufferance resulting from other pressure.

Halfway through the hour, Pete lifted his eyes from the passage that he'd been reading and caught Ms. Masters' eye.

"Can I ask you a question?" he began.

"Of course, you don't learn if you don't ask questions," she replied.

"What do you think was history's greatest love?"

"Oh now that's a bit deep isn't it? And its certainly way off the path of your usual considerations."

"Humour me?" he asked.

"Well its a topic that has been debated many times and by people with a lot more interest in it than I have. Some suggest Cleopatra and Caesar, others Helen of Troy who was stolen away by Paris and started a war. To be honest, its not a topic that I really care enough about to debate. Can I ask why the interest? Is there some great school-based romance that got you thinking about it?"

Pete laughed. "No, there's no great romance. The school-yard debate is usually more about who is the hottest rather than anything deeper. Its pretty much a physical thing too."

"And who is it that they say is the hottest girl in school these days?"

"We'll, the shallow guys who are purely fixated on the physical mostly agree that its Holly Wells, though Missy Angston is either said to be hotter or a very close second depending on who you're talking to. The geekier minded guys who appreciate a bit more intelligence with their beauty mostly agree that its Emma Faringson. Her competition is a close clash between Ashleigh Wu and Yuki Nakamora."

"Interesting and where do you stand on the whole hottest in school debate?"

"Well, I don't think any of them are. I have a preference for women rather than girls." Pete noted that his teacher's eyes narrowed as she waited for him to finish. She was already suspicious. This was where he feared that he'd lose her again. "To me its clear that you're the hottest woman in the school."

She laughed at him. He wondered if she'd been put in such a situation before. He expected that many other boys had had crushes on her over the years. Hell she was sexy now and that wasn't something that developed overnight. Part of her appeal to him was her confidence, the way she seemed totally in control of herself. He hadn't really expected her to laugh though. He expected maybe outrage; perhaps dismissal, possibly a tiny little blush, but not laughter. It threw him off for a moment.

"I'm flattered Peter, but there's no way I'm hotter than those girls. I think that with the evolution of the term MILF there's been something of a renaissance in the desire for an older woman, but trust me, when I undress at night I see all the little flaws that my clothes usually hide away."

"I doubt they're flaws Ms. Masters. I don't think there'd be even one."

"Well you keep that fantasy up Peter, because I'm not about to spoil it with proof."

"That's a shame," Pete replied. "I was hoping to convince you otherwise." He'd said it. It was out there. Silence claimed the room. His teacher looked thoughtful, like she was giving very careful consideration as to what she was going to say next.

"Keep your fantasy. I'm only here to tutor you, nothing else. If you expect otherwise, then I'm afraid I'm going to have to put a stop to these sessions."

"We could come to an arrangement Ms. Masters. I know that you're being well paid to tutor me. That money comes from my father. It's an investment in my education. I have a generous allowance though. I even have some business interests that Father has me look after in order to encourage me to learn more, to appreciate money and to keep me from being a complete sponge. Therefore, I am in a position to offer you money in addition to what he's paying you; a surprising amount of money actually."

"Don't say another word Mr. Irwin," Ms. Masters interrupted him. "I agreed to this despite my better judgment, despite the fact that my instincts told me to turn and walk away. I have even come to appreciate the fact that you're actually putting effort into achieving the grade you supposedly desire. I had even thought that I might have been able to walk away without regret. It appears that that may not be the case."

"Oh come on Ms. Masters, don't be such a stick in the mud. Let me ask you this; are you married?"

"That is hardly the point," she protested.

"But it's a point. I mean, if you were betraying a husband I could perhaps understand some of your reluctance. But you're not married are you? Otherwise you would have simply said yes. In fact, I asked around a bit and no-one even seems to think that you have a boyfriend.

"You asked around?" she asked incredulously.

"Well, kind of, nothing too obvious. Don't worry its not like I tried to find out your sexual history or anything."

"You do realise that relationships between students and teachers are illegal, don't you?" she asked indignantly.

"Its a relationship now?" Pete laughed. "Hell, that's far more than I ever dreamed of. I was thinking more in the short term really."

"Well I think you should be thinking longer term; like your long term future. Nothing good would come of anything between us. So why don't you just drop the whole thought and I'll go back to being your teacher. I'll find a tutor who can help you through the last few weeks until exams and then next year you can snuggle under Daddy's wing and we can laugh about this with our friends in the years to come."

"I think you underestimate my persistence and determination Vicky."

That would be Ms. Masters to you Mr. Irwin," she said cooly.

"But Vicky suits you. It reminds me of that film, Vicky Cristina Barcelona with Angelina Jolie. She nearly has curves to rival yours. Only nearly though."

"Now I know that you're living in a dream," his teacher laughed as she stood to leave.

"You really don't want to walk out of here Ms. Masters. Think about why you agreed to come and tutor me in the first place. I'm sure you received some good advice that helped you to change your mind. Maybe you need to consider if you need to hear that again or not."

"We all have limits Mr. Irwin and I am afraid that I've reached mine." She was half turned to leave and Pete took a chance on checking her out. Her tight black pencil skirt showed off the curve of her ample ass beautifully and the way she was turned pulled her white blouse tight enough against her large tits that he could see the outline of the white bra beneath. He felt himself stirring at the sight. He'd started to harden just from having said as much as he had and from considering that he might have a chance. The vision just sped up the process and it was enough for him to press forward.

"Imagine if I paid you a five hundred dollars just to tutor me with the top two buttons of that blouse undone. Don't tell me you wouldn't be tempted." Pete suggested. There was the slightest hesitation, just enough to give him hope.

"No. It's not a temptation. Do you think I'm a whore? Because its prostitution. I'd be selling myself."

"I think you'll find that its selling yourself for sex that's prostitution."

"The line between them is very thin and its not even well-defined," she retorted.

"Take the money Ms. Masters." Pete pulled his wallet out and counted out five crisp, hundred dollar bills. "Take the money and finish the session. Let's just call it a bonus for the results that you've helped me achieve so far. And you only have to undo two buttons. It's not like I'm asking you to flash me or anything."

She turned and walked out.

Pete jumped from his chair and ran after her, torn between watching her wonderfully fcurved ass as she strode determinedly for the door and trying to talk her into staying. Nothing he said made a difference though. She climbed into her car and drove off. He considered closing the gate to stop her but decided against it. Given the look on her face there was a fair chance that she'd have driven straight through it.

~~~~~~~

Pete sat in history and didn't even attempt to pay attention. He was angry and struggling for ideas. Maybe he'd watched too much porn. Maybe the girls of his era were simply easier. He knew for a fact that if he offered 90% of his female class mates five hundred dollars that they would have done a lot more than undo two buttons of their blouse. Ms. Masters had dressed differently to normal. She was wearing slacks. It was the first time that he could remember her wearing anything other than a skirt. Her blouse wasn't particularly tight either. It was depressing. The only saving grace was when she'd bend over and the somewhat loose slacks would pull tight against her bum or when the light would shine through her blouse.

"Am I boring you Mr. Irwin?" She asked, turning on him suddenly.

"Not at all Ms." he replied.

"Then perhaps you'd care to actually make an effort?"

"Nah, I'm okay thanks," he replied nonchalantly. There was a collective intake of breath around the class. No one said things like that to Ms. Masters. Not ever.

"Principal's office," she said flatly.

Pete stood up and calmly walked from the room. He took his time making his way through the quiet school corridors to the administration area. He ran through the likely discussion he was to face in his head. It was always good to be prepared for these things. It was something else his father had taught him, how to weigh the likely outcomes of a conversation before it happened so that you knew which way you might like to jump in the heat of the moment.

"Hello Peter," the Principal's assistant greeted him when he walked in. "Aren't you supposed to be in class?"

"History with Ms. Masters, Alice. We had a difference of opinion," he said with a cocky smile.

"Ah, yes, well that does happen from time to time," she replied with a conspiratorial wink. He gave her a smile, took a seat and waited until she motioned for him to proceed through the door.

"Mr. Irwin, what brings you here in the middle of class?" he was asked upon entering the Principal's office. He knew that there'd be an email notification on the Principal's computer that told him exactly why he was there. Ms. Masters was nothing if not efficient.

"A difference of opinion really," he replied and took a seat. He saw an odd look cross the principal's face, but ignored it, not knowing what it meant.

"Yes, I see here that Ms. Masters thinks that you should be making an effort in class, but that you don't share that opinion. Unfortunately for you, she's right. I must admit to being a bit puzzled though given it was only a couple of weeks ago that I gave her permission to tutor you outside of school hours. She is even allowed to accept payment for that service so it would seem strange that having asked her to tutor you that you suddenly choose not to participate in class."

"Well it was going well, I was even improving my grade, but it would appear that whatever message you gave with that permission may have been lost. Its okay though, I'll talk to father and I'm sure he'll be able to find a solution. After all, Ms. Masters is a great teacher and I'm sure she'll come around."

"Yes, well I'll have a quiet chat to her as well. I'm sure that she'll see things differently and that we won't need to have your father involved. In the meantime, perhaps show some due respect in class?"

"I can certainly do that Sir."

"Excellent. Well given you haven't been here in quite along with your agreement not to give Ms. Masters a reason to return you to my office, I think we can dispense with any punishment."

"Thank you Sir. I'll pass your regards on to my father."

Pete walked out satisfied. He didn't want to have to speak to his father about the issue. It would lead to awkward questions about why the arrangement had broken down int he first place.

He played one other card that afternoon and hoped that it would be sufficient.

~~~~~~~

Vicky pulled her drawer open to put the last of her things away before heading home and spied the envelope. She took it out and wondered where it had come from. She opened it up and promptly sat back down on her chair.

Cash was the first thing that she saw when she opened it. She glanced to the classroom door to see if she was being watched at all before she counted it. Five hundred dollars. Then she pulled out the paper that accompanied it. It wasn't a note or letter as she'd expected. It was a resume; more of a profile than a resume really. George Irwin. Peter's father. She read slowly through it. It was the recent history that captured her interest.

George Irwin held three board positions in addition to his business interests. The one that stood out was the board of public education. She was taken back to the conversation that she'd had with the Principal; the warning and the threat had gone unspoken. There were two words hand-written at the bottom of the profile.

Two Buttons

~~~~~~~

Pete waited impatiently, wondering if his teacher would show up. He'd not said anything since he'd left the envelope in her desk drawer. He was glad that things had gone so well with the principal and hoped that it would lead to a resumption of tutoring, but there were of course no guarantees. He couldn't imagine asking his father to use his influence and position to sabotage someone's career, but hoped that the unspoken threat would be enough.

"Excuse me Peter, Ms. Masters has just come through the front gate," the housekeeper told him.

"Thank you Maria," he replied. He jumped to his feet and strode quickly to the front door, his heart pounding quicker than he'd expected as his excitement built.

"Ms. Masters," he greeted her warmly and extended a hand to assist her from the car. Even as the door had opened he'd been pleased to note that she was dressed in her traditional outfit of tight skirt and blouse. He noted that there were no more than the two buttons that were usually undone released though as she stepped from the car.

"Peter," she said coolly. He lead her into the house, held the door and then followed her through to the study. As much as he enjoyed admiring her ass on the way, he wasn't quite sure what to expect. He could tell that she wasn't thrilled to be there, but the fact that she was there at all gave him hope that he'd get things his way after all.

He took his seat at his desk and she sat opposite him as she had on every other occasion.

"Two buttons?" she asked without preamble. Pete nodded. He watched as her hands went to her blouse. Blood rushed to his cock and he began to swell as he studied her fingers as they quickly slipped two buttons through their corresponding eyelets. As his teacher sat back, her ample chest spread the navy blue blouse and revealed the edges of a black lace bra beneath. He was suddenly conscious of a need to adjust his cock in his pants, but was too scared to do so immediately. He struggled to concentrate for a while, but eventually Ms. Masters' no-nonsense approach forced him to pay adequate attention to the work that she helped him with.

There were 15 minutes to go when he sat back and took a moment to study her. She sat back as well, clearly wary.

"How much for the rest of the buttons?" Pete asked, sounding significantly more sure of himself than he felt. Without answering, Ms. Masters re-fastened the two buttons, collected her things together, stood up and walked from the room. Pete followed her casually. "I can keep putting money in an envelope until you decide its enough, or you can name a number," he suggested. "I don't suppose you get handed two thousand dollars that you can do whatever you want with very often?"

At the mention of two thousand dollars he detected a momentary hesitation in her gait. She half glanced back, but didn't meet his eye.

Pete watched his teacher drive away and sighed. He'd thought that once he had her accepting money that it would be easy, that it would be a simple matter of escalation. He decided to give it one more go before resorting to other means. After all, each day brought the end of the school year closer.

Pete glanced around the classroom to make sure that no-one was watching as he dropped the envelope into Ms. Masters' drawer. Even though he could able afford it, no-one enjoyed losing two thousand dollars to a thief so he wanted to be sure that no-one had reason to suspect there would be something worth looking at in the drawer. He moved quickly to his seat and sat there casually as the rest of the class arrived and took their own seats. When Ms. Masters arrived she quickly brought the lesson to order and set them some independent work. Pete ensured that he gave her no reason to suspect he was going to do anything other than be part of the lesson, but continually glanced her way to see if she was going to open the drawer. She didn't do so until about two thirds of the way through the lesson. He saw her eyes narrow when she first spotted the envelope. He watched carefully as without taking it out, she peeked inside. He smiled when he saw her eyes widen at the contents. She looked his way and he met her gaze and nodded. She frowned and broke the connection, shoving the envelope firmly back into the drawer.

When the bell rang to signal the end of the lesson Pete left quickly and didn't give her the chance to snag him. He'd expected to be asked to stay behind and have the envelope thrown at him or perhaps to have been sent to see the principal again. Neither happened though and he realised after he left the class that he had no idea what would come next. He was dissatisfied and frustrated by the outcome. He'd hoped for a better indication of whether it would happen at all. He wondered if he should call past her office and find out for sure. He debated with himself, but in the end decided that he'd see if the money and the unspoken threat had been enough.

He waited at home by the front door on the Wednesday for their second session of the week, wondering if she'd show. When she did he walked outside to wait for her to pull up. It was a repeat of her arrival on the Monday with the only emotion displayed seeming to be a cool indifference. Pete followed her into the house after holding the door for her. He stared as her hips swayed and her bountiful ass all but writhed within her skirt. He desperately wanted to lift it to expose her and bend her over. The thought of pulling her ass cheeks wide and slipping his tongue or cock between her pussy lips had him rock hard in his pants by the time they reached his study. He let her take a seat first and just before he sat down he adjusted his erection in his pants, hoping that she'd see it. The fact that she was there at all gave him confidence that he'd broken her; that it wouldn't be long until he would have everything that he'd dreamed of.

Before he had a chance to say anything, Ms. Masters pulled his envelope from her bag and pushed it across the desk. He stared at it. That hadn't been what he'd expected at all. He looked from the envelope to her and was met with a steely gaze. Her lips were pressed firmly together, mere lines instead of their usual full and luscious shape. She took a deep breath and her bosom heaved as she breathed in. The strain against her blouse drew his eye and he recalled how much better it had been without all the buttons done up. He waited for her to say something, but she breathed out slowly as if calming herself and simply sat. Pete reached out and picked up the envelope. He didn't look inside; he just held it a moment and weighed his options. He put it back on the surface of the desk and pushed it back to her. She met his gaze again, but said nothing.

The two of them sat there, staring across the desk at one another and Pete started to wonder if he really had the patience to win. Two more times they each pushed the envelop back towards the other and still neither of them said a word. After he'd pushed it back the second time he saw Ms. Masters reach for it and felt his heart pump rapidly in response. She opened it and very carefully and deliberately counted out five one hundred dollar bills. She placed the envelope back on the desk and undid two buttons. Her white blouse parted to reveal a portion of a white cotton bra; practical and simple. It still made Pete's dick twitch. She pushed the envelope back.

Peter took out his study notes and allowed her to commence, though initially he paid little attention to what was said. He was too busy thinking about what his next move might be.

"Concentrate," she said to him after a while when he'd failed to answer with the level of analysis that she expected.

He pushed the envelope across to her. "Take the blouse off and I will."

She laughed long and hard at that. "What on earth makes you think that you'll be able to concentrate if I take my blouse off?"

"Take it off and I'll prove it to you," he countered.

"And if you can't?"

"If I can't, you can leave, take the money and never tutor me again." That got her attention. He saw the hunger in her expression. It was clear that she wanted a way out, an end to having to do something that she didn't want to be part of. It hurt him a little, but he understood that he'd manipulated her and that it was never going result in friendship. He hoped that he would actually be able to concentrate. It sure as hell wouldn't be easy.

His breath caught as she reached out and pulled the envelope toward her. She picked it up and counted the money inside.

"Its short."

"What?"

"You said two thousand but there's only fifteen hundred in here," she said flatly.

Pete bit back his protest and refused to look at the five hundred that she'd previously counted out onto the desk. Instead he stood up and pulled his wallet from his back pocket. He counted out three hundred then went through to his bedroom. He returned and placed another two hundred with the rest. If Ms. Masters was surprised at how ready to hand one of her high school students had an extra five hundred dollars, she gave no clue. Instead she stood and pulled the blouse from the hem of her skirt.

Pete really stared then. She released each button down the front of her blouse in turn. His eyes were glued to the simple, efficient movements and the bra that was being revealed beneath. It was a little disappointing when compared with Monday's black bra, but as she shrugged the blouse from her shoulders and allowed it to fall down to the back of the chair behind her, he fixed his gaze on it anyway. He studied the curve of the cup where it all but blended with her skin. He decided that she must have had it professionally fitted given how perfectly molded to her it was. There was no sign of the flesh spilling over the bra and each breast sat wonderfully within its cup's confines. Even before he'd had a decent chance to study her properly she launched into the session.

He expected her to pound him with information in an attempt to catch him out, but she had a different, possibly more challenging approach. Rather than give him too much, she spaced it out and gave him too much time to think and observe between bouts of information; ample time to get lost in the beauty of her cleavage. He desperately avoided looking too long at the curve of the bra and the swell of her breasts and focused on the information and instruction that she provided. He was determined to win.

Pete kept half an eye on the clock, seeing time tick away, the hand's staccato movement inching closer to the point where she would leave. He started flicking his gaze to her breasts more regularly, as he sought to inscribe the image in his mind.

When the time came Ms. Masters unceremoniously closed her book and stood up. Pete's eyes followed, glued to her revealed skin. He wished he had a way to get that bra off her immediately, but knew there was no chance. Next time. Next time the last part of his plan would come to fruition. God he disliked being patient. He stood as she reached for her blouse and put it back on. The last thing that she picked up was the envelope of money; a look of distaste on her face. Pete ignored it.

He followed her from the room, satisfied and convinced that the next time he did so he'd have better memories of her visit. He could hardly wait to see that beautiful ass spread for him. He wondered if she shaved her pussy. He hoped so.

"Thanks for everything Ms. Masters," he said happily as if she'd been a completely willing participant.

"Well if nothing else I learned what levels of concentration you can achieve Peter," she said. "I'll expect that same level of concentration in class from now on."

"Well if I had the same incentive I'm sure I'd easily achieve it."

"Yes well that's never going to happen." She pulled the car door closed and drove away.

Pete returned to his study and opened his computer. He was happy to find that the camera had been positioned perfectly. He worked his way through the footage until he reached the moment when Ms. Masters removed her blouse. He watched it over and over, his hand working his hard cock. Once he'd cum, he returned to the footage again. This time he cut it up to match his needs. He made two versions. One where it was evident that his teacher was taking money in return for removing her blouse and one where she simply removed her blouse.

Either video would be publicly humiliating for her, but he wasn't sure which would be the better one for blackmail. He'd find out. He was sure that she valued her job too much to let him do anything with them. He didn't even really want to be that much of an asshole, but he felt his hand had been forced. If she'd just taken the money willingly (or even shown signs of being willing to be seduced) he'd never have taken the step.

He moved to his bedroom and lay back on the bed and day-dreamed of what was to come.

~~~~~~

"So how goes the quest?" Joe asked Pete.

"Quest? What the hell are you on about?" Pete asked with a laugh.

"You know; take Dan's money; Ms. Masters' panties; bone the teacher. The Quest."

"Oh, that," Pete nodded as he came to understand what Pete meant. "Not too bad. Things are on track."

"Things are on track? What the hell does that mean?" Joe replied. "You got some sort of date lined up with her or something?"

"Lets just go with 'or something,'" Pete grinned in reply. Joe looked about to press for more information but Pete cut him off. "No, no more information, I'm not going to have you or any of the others find a way to stuff this up."

"Fair enough man, just, you know, the mind boggles imagining you and Ms. Masters going at it like rabbits."

"Well feel free not to imagine me naked dude, that would be perfectly fine with me." Joe gave Pete a friendly punch to the arm and they each went their separate ways.

~~~~~~~

Pete checked the video at least five times before the tutoring session that Monday. He tried to play out how the conversation with Ms. Masters was likely to go, but kept failing at the part where she would most likely tell him to fuck off at the first suggestion that they have sex. He sighed dramatically and returned to pacing his way through the house as he had been for the hour before he'd checked the video. Maria gave him a few funny looks, but he ignored her just as he did most of the time when he didn't need anything from her.

When the chime finally sounded to announce that someone was at the front gate Pete nearly jumped out of his skin. He took a deep breath and steadied his nerves before heading for the front of the house. He went through the now familiar entrance 'dance' with his teacher, noting that she was still cool toward him. They'd had nothing short of professional student/teacher interactions since the session on the Wednesday prior and Pete hadn't given any indication that today would be anything other than a tutoring session. He'd certainly not given any indication as to any demands that he might make in regard to her clothing.

Ms. Masters was all business. She took out her teaching materials and launched into the session. Pete gave her 10 minutes of dedicated attention before he stopped her.

"Something isn't right Ms. Masters," he said, interrupting her.

"Sorry?" she asked, caught mid sentence.

"Well we made such good progress last time and yet here we are back where we started; you looking as fabulous as ever, yet over-dressed."

"That was a one time deal Mr. Irwin," she replied evenly. "Let's not go pretending it was anything other than that."

"But it was more that that Ms. Masters. It was the a step on a journey. Its time to take another step."