Raising Grades

by Count Doofus

Rating: mature
Tags: Cheerilee, My Little Pony: Friendship is Magic, Other, Romance, Sex
Length: 7300

Filthy Rich and Cheerilee getting 'down'.

*Update: Chapter one has been revised. It's pretty much still the same, just spruced up a little. If you've read it already, you're not missing a thing.*

Diamond Tiara is on the brink of putting the Rich family to shame. Cheerilee informs her father, Filthy Rich, that if she doesn't step up her game soon, she'll have to repeat the grade. Which is something Filthy can help to avoid...

/

Originally written for Sexty Minute Pony Stories. The goal was to write a coherent clopfic with a specific topic within sixty minutes, but I ran out of time while in the middle of it, and had to wrap it up haphazardly.

Chapter 1 is the original story which I have revised to improve the quality, while chapter 2 is a continuation of events.

Front image used with permission, and belongs to Bronystate's talented artist Wrek.

Published 2012-09-19 09:24:03 UTC
Last updated 2012-10-03 21:26:46 UTC

That Cumbersome Filly... (revised)

“Diamond Tiara, please wait outside the building while I talk to your father,” the purple schoolteacher said to the stuffy filly.

The filly in question pouted, though was inwardly happy to oblige. Now she wouldn't have to deal with Cheerilee's berating with her father next to her, giving her glances of disapproval while her teacher talked.

Once Diamond Tiara closed the door behind her and Cheerilee was sure she was out of earshot, she turned to the brown stallion standing in front of her.

“Thank you for coming over on such short notice, Mr. Rich. I know how busy you can get, especially with the Zap Apple harvest around the corner.”

“Think nothing of it, Miss Cheerilee. I can get quite busy as a single parent, but that's no excuse to neglect my only daughter. Though, I get the feeling that is exactly what I'm here for.”

“More or less, yes,” Cheerilee replied. “I'm concerned about Diamond. Not only does she love to berate others that aren't as, shall I say, wealthy as her, but she is starting to neglect her studies as well. Her grades have been in a steady decline for a time now, as you may have seen from her latest tests.”

“I'm afraid I haven't, actually. I've been quite occupied by my work to pay any attention to her results. I had always assumed that while I was working, she'd be in her room, studying.” He recalled last month's phone bill which, though hardly an object, seemed much steeper than usual. “I knew I didn't make that many calls last month. She must've been spending her time calling with that friend of hers... What was it, Silver Fork?”

“Silver Spoon, actually. And your assumptions are probably correct; her grades aren't much better than Diamond's. I intend to talk to her parents tomorrow.”

“Well... Would you mind if I could I take a look at Diamond's results, please?”

“Not at all. They're in my desk drawer. Just a moment, if you please.”

With that, Cheerilee turned around and walked over to her desk. She kept the recent test results in the bottom drawer, so she had to lean down to grasp the handle with her teeth to pull the drawer open. Doing so, she unconsciously raised her rear end into the air, directing it straight towards Filthy Rich.

The stallion followed Cheerilee's every move, mundane as they seemed, until she shoved her rump into the air. Like a set of magnets, his eyes were pulled directly at said area. Thankfully, Cheerilee's tail hid everything underneath from view.

He flinched as he caught himself staring, but struggled to avert his gaze to anywhere else. The last time he had been with a mare - which resulted in Diamond Tiara - had been years ago. Seeing her presenting herself to him like this - accidental or no - made it hard to look away. He felt his face turning red.

Good grief! Why is she doing that? I mean, why would she not get the papers from the other side of the desk? That makes sense, right? Unless she... Goddess, those flanks are so gorgeous- Oh!

Hearing the sound of a closing drawer, he raised his eyes back to Cheerilee's face as she righted and turned around, carrying a stack of papers in her mouth. After putting them on the desk, she opened her mouth to speak, but then noticed Filthy's flustered face. She then immediately realized what she had inadvertently been doing while fetching the tests.

But instead of getting embarrassed, she smiled inwardly, and acted like nothing had happened. Tonight might turn out very interesting...

“Ahem. Well, here are Diamond's results," she said, pointing a hoof at the papers in question. "As you can see, they have been going in a steady decline over the past few months. If this keeps up, I'm afraid she'll have to... well... repeat the grade.”

Filthy's eyes widened. “Oh Goddess, please no. Never in our entire family tree has that debacle occurred. The shame would be unbearable! I, Filthy Rich, father of the first filly in the Rich family that had to repeat a grade? Well, not on my watch. I won't stand for it! Miss Cheerilee, please tell me what to do. I don't care what it takes!”

Cheerilee fiddles with the papers, pretending to make and put them back in the drawer. “Well... Perhaps we could work something out...” she said in a different, softer voice. She lifted the papers to her mouth, but "clumsily" fumbled a few of them. A few errand sheets floated left and right, and one of them even under the desk.

“Oh my, how inept of me. If you'll excuse me...”

Cheerilee turned and ducked again, and reached under the desk, “trying” to fish out the paper from underneath. It was well within her reach, but she strained as if it wasn't, making grunting noises as she faked stretching her limb to its limit, all the while lifting up her rear once more. This time around, she even flicked her tail occasionally, giving the flustered stallion a glimpse at her marehood underneath.

Filthy's mind raced as his eyes were pulled towards her buttocks again. Oh, mother of - she's doing it again! Now I KNOW she's coming on to me. She's not... suggesting that we... do that... in order to raise her grades... Does she? But, on the other hoof... we both know Diamond isn't going to listen to me. Heck, she hardly ever does. I really don't want her to repeat the grade... She sighed. Well... Here goes nothing...

Hoping against hope he wasn't making a bad judgment call, he stepped over to Cheerilee, and delicately slapped a hoof against her rear.

“Oh!” Cheerilee yelped, and bumped her head against the desk (slightly, since there wasn't much room between the desk and the floor to begin with). She righted herself, and looked over he shoulder towards the stallion, grinning as she did. “Why, Mr. Rich. Surely that was an accident.”

“Uhm... Only if you want it to be,” he said, still quite unsure of her intentions.

“I don't,” she replied as she turned around, lowering her eyelids to a seductive stare. “Suddenly, Diamond's latest F got turned into a D minus. Imagine what would happen if more... "accidents" like that occurred...”

Inwardly sighing with relief that he read the signs right, Filthy smirked, closed his eyes, and leaned in for a kiss. He got halfway before Cheerilee threw her forehooves around his neck, and locked her lips with his. Filthy flinched, but quickly eased into the kiss as Cheerilee forced her tongue into his facial orifice.

Moaning softly, their tongues swirled around each other. After a few tense moments, Cheerilee broke the kiss, and sucked in a sharp breath of fresh air. “D plus.”

Next thing she knew, Filthy gently pushed her backwards until her rump bumped against the desk behind her. Wasting little time, he placed his own forehooves underneath her shoulders, pushed her up the desk and resumed his kissing. Cheerilee's cheeks flustered crimson – hardly visible due to her purple coat – as Filthy proceeded to plant little pecks across her cheek, her neck, her chest, and going lower still.

“C minus,” Cheerilee grunted as she bit her lower lip while reclining on her desk. Filthy had reached her nethers, which were already glistering ever so slightly. Feeling his stallionhood beginning to stand at attention from the pleasure running through him, he reached out to it with a free hoof, giving it gentle strokes as it hardened.

“G-Go ahead, Mr. Rich... Earn your daughter a C plus...” Cheerilee groaned as she looked down at Filthy Rich. His nostrils filled up with a musky scent as his mouth hovered just above her moist lower lips. He looked up, and locked his eyes with hers for the briefest of moments. “For now... You can call me Filthy,” he said, before plunging his tongue down Cheerilee's marehood.

“OH!” she yelped, feeling the flexible piece of muscle squirm its way inside her, lapping up the natural lubricant she was producing. She lifted her hoof to bite into it, preventing herself from making moans of pleasure. Diamond Tiara was still in the vicinity, after all.

That concern vanished like snow in the sun as Filthy found his way to her her fun button. Eyes widening like saucers and rolling away to the back of her head, she took in sharp breaths as Filthy alternated between working her lips and her clitoris. Her climax was building fast through his administrations. It had been so long since she had been with a stallion, and while toys offered some compensation, there was nothing quite like the real deal.

“Uh... Deeper...” she moaned, urging Filthy to increase his efforts. He complied by stretching out his mouth to its limits, and then closed it around her nether area, forcing his tongue in as far as it could go. Through this act, he had to resort to breathe through his nose, which tickled her sensitive teats.

Seconds seemed like centuries for Cheerilee as she tried her best not to scream in delight, every lick another stroke of unparalleled bliss as her climax built. Her moaning drove Filthy's tongue to its absolute limits, reaching just a little bit deeper every time. Just when the tongue reached the apex of its flexibility, Cheerilee suddenly shocked and gasped loudly as a salty liquid splattered all over the inside of his mouth. She tried her utmost not to cry out in ecstasy from her sexual release. He closed his eyes, and allowed the liquids to pool up inside his mouth, until Cheerilee grew still. With her eyes closed, one forehoof resting on her chest and the other lolling over the side of the desk, she muttered in ragged breaths, “B... minus...”

Filthy removed himself from Cheerilee's marehood, some of the liquids spilling out before he managed to shut his jaw. With bloated cheeks, he climbed halfway up the desk, bringing his face in front of the teacher's. Becoming aware of the nearby body heat and the sound of hooves on wood, Cheerilee managed to open her eyes to a slit, and saw Filthy's face in front of hers, leaning in for another kiss. She complied and opened her mouth. Filthy did the same, which resulted in letting her own produce spill into her mouth as they locked lips.

When the kiss was broken, Cheerilee swallowed down her own juices while Filthy did the same, even though there was hardly anything left. Both of them savored the sensation, and relished in the moment.

Before either of them could contemplate taking things to the next level, an all-too-familiar voice sounded from outside the classroom door.

“Daaaaaad! Are you almost done in there?! I'm – so – bored!”

Startled, Filthy turned around, trying to think of something to prevent his daughter from walking through the door. “In a minute, honey!” he shouted out. “I'm almost done with your teacher! Uh – talking, that is!”

“Whatever,” she replied huffily, “just hurry already. I don't wanna miss the next episode of NTV's Stables!”

Due to the interruption, Filthy's member had started to retract into his body again, since it was clear it was going to be devoid of action today. Cheerilee grinned at him while wiping her mouth. “We'll have to pick this... 'conversation' up another time. Then we'll see if we can't do anything to bump her grade up to somewhere in the A department.”

Filthy proceeded to clean his own muzzle before he replied, “Looking forward to it, Miss Cheerilee."

“How about next week Friday? I'll be sure not to dish out any detention, as to prevent another situation like this.”

“Sounds fine to me,” he said. He lowered his head to look down at his member, which had fully retreated by now. “Sorry, old fella. You'll be getting some, soon. Promise.” He raised his head back up to address his daughter's teacher. “Tutor's permitting.”

“We'll see, Mr. Rich. Oh, and for the record, Diamond isn't in the clear yet. There are more tests to come, and if she flunks those... well...” she winked.

Filthy Rich smirked as he made his way to the door and opened it, a little pink filly waiting impatiently on the other side.

“There you are, finally! Come on, the show's about to start!”

“Alright, alright, we're going.” He threw one last glance at the teacher before he left the building, and wiggled his eyebrows.

Maybe... repeating the grade isn't such a bad thing...

"Graduating"

Filthy Rich arrived at the schoolhouse, roughly an hour after the final class of the day was dismissed. The sole reason for being here was to let Filthy Jr. out for 'recess,' excusing himself from his household under the guise of an emergency meeting with an associate.

However, somewhere deep in his mind, he couldn't help but feeling none of this was right.

Last time he was here, after enjoying a little private time with his daughter's schoolteacher, his sense of judgment was too bedazzled to fully comprehend the situation he had found himself in. He was doing his part in making sure Diamond Tiara would pass on to the next grade and avoid eternal shame upon his family, while in reality, it was Diamond who had erred and had to repent. If she were to take her studies seriously, he needn't do this. Yet here he was, cheating her way to graduation by the act of bribe-coitus.

No more.

He planned to tell Cheerilee that he was going to make sure Diamond Tiara was going to pass the grade in the way a student ought to - by studying and passing tests. No other way, no way, no how.

... After today's events.

He was still an entrepreneur at heart, and it was simply in his nature to seize any kind of beneficial opportunities that were offered to him. In this particular case, it didn't involve any kind of numbers making their way to his personal funding. No, this was strictly pleasure. Like anypony else, even he needed to unwind in some way - after all, all work and no play...

He winced at the thought of being a freeloader. Deep down, it felt wrong to 'use' Cheerilee like this, then toss her aside like a shredded rag doll. But the gentlecolt in him made sure to make good on the promise he made her a week prior. He planned to tell her after they had their 'fun' to let her know this was the second and last time he intended for them to meet in this fashion. If at all, maybe they could work out a special schedule for Diamond Tiara in an attempt to bump up her grade. If that didn't work, he would, as a last resort, just deny his daughter any kind of luxury until her grades began to rise.

Taking a deep breath, he approached the schoolhouse.

Given that the building only had one classroom, he quickly found himself in front of the door that lead into said classroom. Gulping hard, he knocked a few times and waited for a response.

"Come on in," a seductive voice sounded from the other side. If Filthy didn't know any better, he'd swear he heard Princess Celestia talking.

Opening the door, the first thing Filthy saw was the side of the desk where he had first shown the teacher such a good time before. What was new, however, was the appearance of the teacher sitting behind it.

She wore clothing. Not the type the fancy ponies up in Canterlot would prance around with like overstuffed peacocks, but skimpy, highly suggestive fabrics. It consisted of a barely secured purple necktie and an ivory shirt, the top two buttons undone. The mere sight of her already hazed Filthy's senses as a familiar twinge sparked between his legs.

Cheerilee was working on some pretend-paperwork as Filthy walked in. Turning her head to look in his direction, she removed herself from her desk, revealing a set of frilly stockings traveling all the way up her legs, covering up part of her cutie mark. It caused Filthy to gulp once more.

"Why hello there, Mr. Rich. Welcome to your very own after-school special." Cheerilee grinned, and slowly walked over to him. "What say you we pick up our... 'session' where we left off from last time?"

Filthy glanced around nervously as she closed the distance between them, suddenly not entirely sure if he wanted to go through with this anymore. He opened his mouth to speak, but before he got a chance to even get a single letter out, Cheerilee launched herself forward, swung her forehooves around his neck, and plunged her tongue into his mouth, locking her lips with his.

Filthy initially startled, but quickly eased into the kiss as Cheerilee explored the inside of his mouth.

Well... Maybe I shouldn't be so selfish. Goddess knows how long she's been without sex, and who am I to deny her that. Besides, given her outfit, I'd say she was looking forward to this...

He was broken out of his musings when Cheerilee broke the kiss, and leaned forward to rest her head on Filthy's shoulder. "Thank you for coming back..." she whispered in his ear, "you have no idea how much I've been looking forward to this..."

Heh, called it, Filthy thought. "You're more than welcome," he whispered back. "If I must be honest, I haven't had any myself ever since Diamond Tiara was born... I haven't so much as looked at another mare ever since her mother passed when giving birth to her, and-"

"Shh..." Cheerilee cooed, placing a hoof on his lips to silence him. "Don't talk about that. Let's just enjoy this for tonight."

He nodded, and Cheerilee guided him to her desk. "Put your hooves on the edge, and let me do the rest..."

Filthy complied, and proceeded to place his forehooves on the exact spot where he ate out Cheerilee the last time he was here. She disappeared from his peripheral view, and looked down to see Cheerilee taking an interest in his slowly exposing member.

Cheerilee grinned at the object of her attention. I'm going to have some fun with this... she thought as she put her hooves on either side of it, and started to softly knead it while gently licking the tip.

Filthy failed to stifle a grunt as the teacher began her administrations. Her gentle caressing caused his heart to beat faster, which resulted in more blood being pumped through his veins, which in turn caused his member to grow rock-hard within seconds.

"Oh my, somepony's eager," Cheerilee giggled. "Now be a good student and leave your hooves where they are. You don't want me to punish you... Do you?"

"No ma'am," Filthy said, playing along with the teacher's fantastical indulgence.

"Good boy. Now, hold still..."

Cheerilee proceeded to slowly rub her hooves back and forth across Filthy's member, occasionally lapping up the beads of his natural lubricant emerging from the tip. "Hmm... salty..." she said, relishing in tasting Filthy's produce. She then moved her head to the base of Filthy's shaft, stuck her tongue out and gave his entire length a firm, single lick, finishing the motion with taking the tip in her mouth, and give it a solitary suck before releasing it again. Filthy held his breath during the entire process, releasing it simultaneously when Cheerilee disengaged her mouth.

"Oh wow," he panted, "never had that happen before..."

"Heh, I'm not done yet... Not by a long shot..." Cheerilee grinned, and kicked her administrations up a notch by taking his member in her mouth again. Only now, she kept it there, and swirled her tongue around it as far as it could reach.

Filthy clenched his eyes shut, reveling in the pleasure Cheerilee was bestowing him with. He resisted the urge to shove his hips forward, which became increasingly more difficult as the mare below him worked, his senses getting more and more overcome with a primal instinct.

Moving up a gear, Cheerilee rested his member on her tongue, and slowly began to move her head forward until it contacted the back of her throat. Though Filthy was of average size, it was far too much for her to take completely. So, she resorted to letting it creep forward bit by tiny bit, until her gag reflex was about to kick in, and slowly retreated. Just before fully releasing him, she moved forward again, and started repeating the motion in a steady rhythm.

Filthy was in bliss. His hooves were shaking, his mind screaming at him to move at least one of them to the back of Cheerilee's head. He bit down his lower lip in both resisting that urge, and the enjoyment from the schoolteacher's administrations. His climax started building from deep within his loins. He usually lasted far longer if he ever had the need to 'take care of himself,' but now getting the job done for him, he could already tell he wouldn't last longer than a few minutes.

Cheerilee, ever so slowly, kept increasing the pace at which she sucked on Filthy's penis. Her saliva mingled with his lubrication abundantly, which made her motions all the easier to perform. She could feel his member throbbing in sync with his heartbeat, indicating he was getting dangerously close to ejaculating.

"Unf... S-slow down a bit, Ch-Cheerilee... I'm... I don't want to... Not yet..." Filthy Rich groaned.

Cheerilee, on the other hoof, did quite the opposite.

She firmly wrapped her hooves around Filthy's legs, just above the hocks, and doubled her efforts in sucking him off. She bobbed her head back and forth at a furious pace, taking in as much of the throbbing member her orifice would allow. She panted heavily through her nose, and felt her own marehood starting to gush with excitement.

Filthy groaned loudly as Cheerilee worked his meat. His arousal rocketed sky high at this rate, and his eyes rolled to the back of his head from sheer, blinding pleasure as his impending climax reached new heights. Before he knew it...

"Nng... Unf... I'm-I'M GONNA..." He shouted as he stretched his forelegs and arched his back as he went over the edge.

Below him, Cheerilee knew exactly what she wanted. Keeping Filthy's member in her mouth, she grabbed her shirt with both hooves and ripped it open, baring her chest. Any unfortunate fastened buttons got dislodged effectively, and scattered in every direction gravity took them. Cheerilee allowed Filthy to shoot a few loads of his warm semen in her facial orifice, then pulled out while keeping her mouth open. The rest of his spurts splattered all over her face and chest, while the tie still around her neck changed to a darker hue with streaks of transparent white liquid. She gulped down felicitously whatever of it got caught in her mouth.

As Filthy rode out his orgasm, his semen practically cascaded down Cheerilee's body, trailing all the way down across her chest and stomach, surpassing her moist marehood which was leaking her own produce of natural lubricant, to finally end up on the wooden floor below, joining in the puddle Cheerilee inadvertently had created there. She relished in the sensation of being coated the way she was now.

"Dear sweet Celestia... I can't believe how much I missed this!" she exclaimed.

Filthy, for his part, finally got back on all fours and all but collapsed to his knees next to Cheerilee and laid his head down, utterly spent as his member fell flat.

"Uh... I, uh... Hah... Gimme a minute..." he panted. It was crystal clear to the teacher it had been a very long time for him to have released like this as well.

It took Filthy several minutes of heavy breathing and recovering his wits, while Cheerilee savored on his reproductive fluids. She stroked one of her hooves across her fur, starting from her nethers all the way up to her chin, scooping up whatever beads of liquids she could, and gingerly licked her hoof clean until she had consumed all that she could gather. Meanwhile, she circled her other hoof over her moist marehood, occasionally dipping it in the puddle directly underneath it to add elation to the motion, setting her loins ablaze.

"Oh Filthy, wouldn't you know it. You've up and gotten me so far gone, I can't help but crave for you to be inside me..."

"Just... a little while longer, please..." came his reply, breathing less hard now as his body had nearly recovered. He got back on his hooves, swaying a little as his legs still were somewhat unstable. He turned his head to face the teacher, but what he saw nearly sent him to the ground again.

She glared at him with her eyes locked in a seductive stare as she nipped on one hoof and letting the other one caress her genitalia. A large portion of her coat was matted in a slightly darker hue of purple, for which she had Filthy to thank. Seeing her pleasuring herself, not to mention the sight of her shirt pulled open, one side having slid past her shoulder, Filthy Rich could feel his little soldier standing to attention again.

"Wow..." he uttered as he sat on his haunches.

"Heehee... Thank you," Cheerilee giggled as her eyes stole a glance towards his endowment, "Mmmm... I see somepony's getting ready for round two." She leaned forward to lock lips with Filthy, allowing him a taste of himself as their tongues swirled around one another. Cheerilee moaned loudly into his mouth when she felt the back of his hoof stroke across her lower opening, his fur tickling at her sensitive button, which caused another trickle of her lubrication to emerge.

She broke the kiss, and leaned forward to whisper in his ear, "How do you want me?" after which she playfully nibbled on it. Stifling a chuckle, a naughty idea sprung to Filthy's head, after which he looked towards the empty lecterns.

"Well..."

"Oh, Filthy, this idea is very... well... filthy!" Cheerilee looked over her shoulder, and smirked. "I love it."

Filthy couldn't help but grin like an idiot at the fruition of his idea as he came up behind her. "She'd kill me if she ever found out about this."

"Yes, well, let's do our best to make sure she doesn't, right?"

"Right, rightrightright. Well then... Shall we proceed?" Filthy asked, his eyed glued to the purple rump, which was practically begging to be abused.

"Uhm... Before we do..." Filthy's ears perked up as he noticed the change of tone in her voice. Looking directed at her, he saw she was looking a bit worried, which meant that whatever she was going to say next was important to her.

"Yes?"

"Two things, if you don't mind..." she began. "Could you refrain from going anal? I've tried it before, but I didn't enjoy that one bit."

"Sure. I'm not a big fan of it myself. And what's the other?"

"When you finish, please pull out before you do. Estrus hasn't hit me for as far as I can tell, but I want to reduce the possibility of conception as much as possible."

In his mind, Filthy could already image himself shooting his load all across Cheerilee's rump and the back of her shirt. Maybe even a few strands in her mane... The imagination made him all the more eager to get started.

"If that's what you want, that's what you'll get, Miss Cheerilee."

Her seductive stare returned to her face. "It is. And thank you. But right now, what I want is you..."

She faced forward again towards the empty classroom, adjusting and spreading her hind legs a little as she got more comfortable while leaning over Diamond Tiara's lectern. She closed her eyes and smiled in expectancy...

Filthy, on his part, leaned in at the display in front of him. Brushing her tail aside, still matted from their previous activities, he took a deep whiff from Cheerilee's nethers which accrued his arousal even further. He exhaled his hot breath on the same spot, earning a slight shudder from the schoolmare.

"Please..." she said, a bit annoyed yet still eager with anticipation, "stop your teasing and- HAH!"

Cheerilee got cut off effectively and moaned loudly as Filthy started caressing her marehood with his tongue, lapping up the tiny dribble of her liquids in gentle strokes. With each lick, Cheerilee felt her loins growing hotter and hotter until it felt like it rivaled the heat of Celestia's sun.

A fire that could only be extinguished in one way.

"Please, Filthy..." she begged, "do it..."

Glancing up past the point where the tail emerged from her body to the back of her head, Filthy removed his mouth from her genitals. Grinning mischievously, he repositioned himself behind her by lifting up his forehooves to rest on top of her flanks, inching his eager member closer and closer.

Cheerilee gasped sharply upon contact, but gritted her teeth in sexual frustration when she realized the stallion continued to tease her.

Instead of moving in like she expected him to, he grinded his member across her slit in gentle, fluid motions, moisturizing it to allow for easier access, plus further elating her own arousal. She felt like protesting, but found herself unable to speak as Filthy ever so gently contacted her most sensitive of places - the tiny spot just above her lower entrance.

"Okay... I'm ready now," Filthy Rich announced when he determined his tool was slick enough to allow their genitalia to experience the least possible discomfort. "Just close your eyes... and relax..."

Moving his forehooves to rest on the backrest of Diamond Tiara's lectern, he realigned his approach, adjusting his hind legs as he inched closer and closer, until the tip of his member contacted the pink slot of Cheerilee's marehood. The owner of the latter clenched her teeth in preparation of being penetrated.

"Here it comes..."

Inch by inch, Filthy pushed himself in, stretching Cheerilee's walls around him. Her body instinctively resisted, causing Filthy to enter her at an agonizingly slow pace. But the further he got, the less her body convulsed around him.

Cheerilee's mind was a huge haze. She couldn't think straight. It's been forever since she'd been penetrated. She tried to relax at the feeling of being filled up, but it was so overwhelming, it nearly scared her.

Filthy shuffled closer as his hips closed the distance between him and the teacher's rump. With every inch he managed to work inside, he could feel more of her tail brushing at his belly, and the warmth of her legs beaming against his own. But most of all, he relished in the feeling of his member continuously being surrounded by warm, moist flesh. Undoubtedly the best feeling in the world any stallion could ever ask for, regardless of orientation.

Time flew by as he kept sliding in, until he finally bottomed out. As his testicles touched her inner thighs and his hips rested against her rump, he savored the moment by just holding the position of being buried inside her for a while. He leaned forward towards Cheerilee's ear.

"You okay?" he whispered, genuinely concerned for her wellbeing.

Cheerilee let her head hang down, right between her forelegs which rested on Diamond's chair, and panted heavily. "Mhmm," was all she could manage to bring forth. A drip of saliva fell from her mouth. She didn't bother to stop it.

"Alright," he whispered back, "let me know if I start to hurt you..." With that, he lifted his own rump and began pulling back, a dribble of her juices joining the motion.

Cheerilee clenched her teeth at the sensation. Filthy had moved his forelegs next to her own, and had them clasped around the teacher's frame as he backed out, halting her from pulling back with him. The air brushed around the exposed flesh of Filthy's member, coated in slick liquids, making him wince a little. He remedied this by gently sliding in again.

Cheerilee moaned as he eased in, reveling in the feeling of being filled again. Just as soon as he bottomed out in her a second time, he pulled back out a few inches, only to refill her, again and again, until he found a steady rhythm in his movements.

As far as she was concerned, time had no meaning anymore. She blanked out, unaware and uncaring of where she was in the world. She didn't care if Diamond Tiara, her class - heck, Princess Celestia and/or Luna would barge in right now. All that mattered to her was this moment, right here, right now. If she was able to, she'd feel sorry for anypony who hadn't experienced the act of intercourse yet.

Filthy shifted. He brought himself up, resting his forehooves now besides the purple mare's body. Gradually, he intensified his rhythm, still gentle yet a little bit more firm.

The shift in positioning allowed his member to reach niches inside Cheerilee it didn't touch before. The sensation made the teacher draw her head back, while each thrust had her moaning in ecstasy.

"Yes... Filthy, oh yes... Keep going..."

Filthy Rich grinned, pleased with himself knowing he still knew how to give a mare a good time. It really was like riding a bike... You know, if he ever learned how to ride one anyway.

He kicked his administrations up ever so slightly... but it was enough to drive Cheerilee over the edge.

Head tilted backwards and screaming to the heavens, Cheerilee's body rocked and twitched as she orgasmed. Scores of her lubricational liquids gushed out from her marehood past Filthy's rod, splattering all over his testicles and legs, while it repainted the floor and parts of Diamond Tiara's lectern. But at that moment, neither of them couldn't care less about the possible repercussions.

A switch flipped in Filthy's brain. All sense of gentleness went out the window as he placed his forehooves on her back, clenching the fabric of her shirt and started pounding away, kicking his motions into high gear. He clenched his lower lip so hard, it almost started to bleed.

Cheerilee's eyes widened from his sudden increase in pace. She hadn't recovered from her climax yet, and now her opening was receiving the roughest treatment it had for a long while. She didn't complain, however - the abundance of fluids coating both her walls and his member made sure neither of them experienced any kind of discomfort. Instead, she closed her eyes and let the sensation take hold of her, moaning sharply and loudly with every powerful thrust.

"Oh... Filthy! Oh! I-I want to feel you... all over my back...! Rip it! Rip it!"

Filthy tensed the muscles in his forelegs at her exclamation, gripping the fabric harder. A little tear appeared in between where he grasped her shirt, and, bolstered by the moment, forcefully drove his legs away from each other, resulting in a ripping noise, exposing Cheerilee's perspired back. What was once her shirt now fell in two perfect halves past her own forelegs.

Filthy wrapped his hooves around her hips while continuing to buck her furiously. The act of ripping her clothes off, combined with the caressing of his length against her walls, was getting too much for him to bear. He could feel the head of his member swell up, and groaned loudly as the contents of his testicles began their journey from one body to another.. Cheerilee panicked momentarily as she felt the former sensation for herself, but sighed happily as, in a moment of clarity, Filthy removed himself from her trembling form.

Furiously grasping his hoof around his flaring member to finish the job, Filthy grunted repeatedly as he climaxed, and began painting her back in thick, wet splodges of his reproductive fluids. The first spurt even went as far as over her head, ending up against the lectern on the second row behind Diamond's.

Cheerilee giggled in ecstatic bliss as she felt her back being coated with his seed. It soaked her fur down to her skin, rolling down on either side of her body. Some trails of semen ended up directly on Diamond Tiara's lectern, while others came together on Cheerilee's chest and dribbled towards the seat from there, or ran down the teacher's forelegs only to be absorbed by what was left of her shirt.

After Filthy Rich had ridden out his orgasm and exerted his final spurts which reached as far as Cheerilee's rump, his legs buckled underneath him and he all but collapsed to the floor, utterly spent and panting heavily. His flattening member continued to leak a few trickles of lingering fluids, too late to join the initial bursts.

Cheerilee on her part, panting equally hard, remained bent over on Diamond's lectern while both of their juices trailed down her legs, allowing her body to recover enough energy in order to be able to walk on all fours normally again. She was certain she was going to walk a bit funny after tonight's events, though.

After a few minutes of recuperation, she side-stepped away from the lectern, the fabrics of what was once her shirt dragging across the floor as she walked. She turned to look at Filthy Rich, whom was still breathing heavily, eyes squinted to a slit and smiling happily as he basked in the afterglow of their coupling.

Cheerilee lowered herself on her knees next to the brown stallion, uncaring of the puddles of liquids everywhere, and smiled at him. Filthy had just enough energy to direct his eyes at her, and to utter a few words. "That... That was... I mean... Wow..."

The teacher closed her eyes, and giggled a bit. "It was, wasn't it?" Her smile changed from a compassionate to a sincerely grateful one. "I haven't felt so good in ages, Mr. Rich. And you kept true to your promise. I can't thank you enough for that."

Filthy smiled back at her. "The feeling is mutual, Miss Cheerilee. It's been a long time since I-"

"But I'm afraid it will have to end here."

Filthy closed his mouth and opened his eyes to their normal state. "Uh... I don't follow."

"Don't get me wrong, tonight was extraordinarily special, and I'll never forget it for as long as I live," she said, "but our motivation is wrong. You... well... we've been using sex as a means to make sure Diamond Tiara passes onto the next grade. But you have to acknowledge that this isn't the way to do it. It ultimately falls down to her, and all that we are meant to do is support her to make sure she pulls through." She sighed. "I can't help but think I've failed as a teacher in that regard. Just as nopony in your family ever had to repeat a grade, neither have I ever had a student do the same..." She turned away, too ashamed to look Diamond's father in the eye.

The stallion righted himself to his knees, sitting directly across from the teacher. "You are not a bad teacher, Miss Cheerilee. Your cutie mark confirms that. In fact, I agree with you on every account. Diamond Tiara is the one who has to work in order to graduate, not us. You're not at fault, she is. As soon as I am able, I'm going to focus less on my work and more on her and her studies." He put his hoof on the teacher's cheek, and gently pulled her head back to look her in the eyes. "And that's a promise."

"Hmmm..." Cheerilee smiled and closed her eyes as she leaned into Filthy's hoof, caressing it with her own. She relished in the caring touch, until her eyes shot open in realization.

"Wait a second. You said 'on every account.' Does that mean you agree with what we did was wrong?"

"No. What we did was..." He gulped. "It felt very right. As you said, it was the motivation behind it that's wrong. I'll have you know that I was planning to tell you the exact same thing after tonight's events. I hope that doesn't make you think any less of me..."

"What? No, not at all! In fact, I'm relieved! I wasn't sure how you'd take the news."

Filthy smiled reassuringly. "Have no fear. I agree with you. Though, I don't suppose..." He started to fiddle with his forehooves, not sure how exactly to phrase his next question.

"Don't suppose what, Mr. Rich?"

"Please, Miss Cheerilee. I think after tonight, you're entitled to call me Filthy whenever you please."

"Heehee... That goes both ways... Filthy."

"Okay... Cheerilee. Anyway, what I was going to ask... was... uhm... Celestia, how do I put this... I don't suppose if we can... you know... do this again at some point?"

"Why, Filthy... are you asking me to be your very special..." Filthy's mind went to DEFCON 5-mode when the teacher spoke those last two words. In a flash, he recalled the promise he made to the tombstone that had his wife's name on it. Never again in his life could he love another mare the way he loved her, and vowed on the spot never to marry again. He couldn't stand losing a second wife, if it were to come to that.

"... buckpony?"

Filthy Rich was taken slightly aback at her bluntness. On the other hoof, he instantly felt a great deal of relief when she said 'buck' instead of 'some.' He coughed.

"Ahem... Well, I wasn't going to put it like that... But, since that is what it boils down to... Yes."

Cheerilee smiled, and leaned forward to lock her lips with his own again. When she broke it, she looked into his eyes with the most sincere gaze she could muster. "I'd love to."

Relieved, Filthy smiled, and scooted closer to her to lock her into an affectionate embrace, which she returned.

After a few moments, Cheerilee became aware of a musky smell. She'd smelled it before, but only now paid any attention to it. Releasing the stallion, she glanced around at the various puddles in their immediate area, not to mention the stains in various places on their coats.

"I guess we ought to clean ourselves up... And this place next."

Filthy glanced around for himself. "Couldn't agree more."

The next Monday...

"Hey, Apple Bloom! I see you finally got your cutie mark. Congratulations!" Diamond Tiara said to the yellow, red-haired earth filly as they walked into the classroom, blissfully unaware of the actions that partook a few days prior.

"Huh?" She blinked in confusion, and immediately shot her eyes towards her left flank. "Mah cutie mark? For real? What's it sa- hey!" Her elevated spirit turned into a moody one when she noticed her flank was still bare, and gave the snooty pink filly a glare that could kill if it had the ability to.

"Yeah! Don't you see it? It's nothing, because you're so good at nothing!" She giggled, Silver Spoon giggling with her as well as they made their signature hoofshake. Apple Bloom trotted off angrily towards her lectern, muttering to herself as Diamond Tiara and Silver Spoon walked to theirs.

Diamond Tiara was still smiling as she sat down. But her smile was quickly wiped from her face when a particular scent assaulted her nostrils.

Eewww! What IS that disgusting smell? I think I'm gonna be sick!

From behind her desk, Cheerilee sneaked a glance at the arrogant pink filly, and smirked knowingly.