Cheerilee's Special Valentine's Day Class
Bad Teacher
Previous ChapterNext ChapterRumble stuffed his hands into his football jacket as he walked through the halls, trying to get back some of the warmth the cold outside had taken from him. Doesn’t help that I had to walk all the way from Silver’s. He heaved a sigh of annoyance, recalling the brief glimpse of another stallion, another suitor. He shook the thought away, as he always had in the past, and comforted himself with the simple thought that he would be victorious, someday.
A few fingers stretched out and grabbed part of the note in his pocket. I shouldn’t be here though. I really shouldn’t be here. And yet his hooves continued to noisily clop against the tiled floors. He went into autopilot as he maneuvered the hallways, admiring the place that held his childhood.
A smirk grew on his face as he stopped in front of a trophy case. Rumble breathed against the glass and rubbed part of his jacket on it to get a better view. “Champions. Always were, always will be.” He stood straight, taking in deep breaths as the smirk became a content smile, the taste of SIlver’s lips on his mouth from after that stormball game coming back in full.
“That is a very good attitude to have.”
Rumble jumped at the voice and looked to the new presence. Immediately, his tongue retreated down his throat at the sight of Cheerilee, or, to be specific, the outfit she was wearing. It was a school girl’s outfit, only it was about three sizes too small. Her large bust almost ripped the shirt apart, and just a hint of a darker pink slipped out of the fabric. His heart almost stopped as she came closer and lifted one of her legs, putting her knee on the cabinet.
He tore his head away from the massive cleavage and luscious legs, staring back into Cheerilee’s eyes. He swallowed hard and forced a smile. “H-how are you Cheer-” He stopped as her face got much closer and one finger was placed on his lips.
“Perfect. Call me that.”
His jaw started to ache at how much he fought his mouth’s desire to drop. “Alright, um, Cheer, I-I got your letter.”
Cheerilee bounced away and Rumble had to wonder how in the world her breasts weren’t simply coming out. He had no such thoughts on the miniskirt as he was flashed a pair of moons that were completely uncovered. She glanced back at him. “I am very happy to hear you did. Now, follow me.”
He swallowed hard, but did as he was told. Rumble tried to tell himself this was just his teacher, but the swaying of her blue skirt kept dragging his attention down while his libido begged for another infrequent glance at her large booty. One of these times, Cheerilee’s hand came back and stopped her skirt from moving just as he could see that tempting ass in full glory. A glance up showed her watching him, but before he could say anything, the hand was away.
They burst into the cafeteria and made their way quickly along to the counters where Cheerilee hopped over the serving shields. Before Rumble could jump over, he got a full view of her rump as she bent over to pat her legs. His cock pushed against his pants as his eyes finally went to a small slit between those heavenly thighs, but he managed to dismiss his gaze before long. She turned back to him. “Are you coming?”
“Uh, um, yeah.” He popped his wings open, though how nervous he was already had them tight. She was now willing to squat, which only caused Rumble’s eye to start twitching. “So, why did you ask for me to be, um, your… friend for Valentine’s day?”
She stood, smiling as she handed him one of the two bananas she had, and his veins turned to ice. She brought the stem to her lips and bit into it before pulling it down. Rumbled’s fingers curled as she ran her tongue along the now exposed fruit. He snapped when she let out a moan at the same time she inserted the tip. “Alright, what the fuck is this?”
Cheerilee raised an eyebrow. “What do you mean?”
He stepped forward and spread his wing which was countered by a simple smirk from her. “You know me and Silver are together!”
One of her hands covered her mouth as she looked away from the light gray pegasus. “Now whatever would cause you to remind me of that?”
He almost wanted to pull his hair out from the answer, but then he noticed where her hands drifted to. One gently pulled at the top, slowly revealing more and more of her breast. It was the last straw for him.
Smack!
Rumble stared at his hand, unsure where the action had come from. He had simply reacted, stopped her from doing something so wrong. Cheerilee turned to him and his heart twinged at the pain in her eyes. Something stopped him from apologizing, the same part that said that his teacher had turned into a harlot.
Her fingers laced into his own and brought his attention back to her instead of the action. “You… you got frustrated, didn’t you?”
Finally, his mind started to thaw. “Oh sweet Celestia, I’m so sorry-”
“You don’t care about me enough. I understand that.”
Rumble blinked a few times. “What?”
“I’ve seen you and her around town. She orders you around, pushes you, and if rumors serve right, still won’t let you kiss her around Diamond Tiara.”
He paled as it clicked. “Th-this is diff…” He looked away, the stern stare from her taking away the outfit and reminding him of all the times he had to be told to stop being like Thunderlane. “I-I’m eighteen. I don’t need to listen to you.”
Rumble was almost at the door when his tail got pulled. He turned back and saw the coarse, gray hairs in Cheerilee’s hand. The other hand went up to her cheek as she simply raised an eyebrow. Rumbled swallowed hard. “I, I said it was on accident.”
“And how long before your frustration leads to another accident?”
“It won’t!”
Cheerilee was silent as Rumble panted, having charged his way to just in front of her. His eyes widened in horror, but he stayed due to the soft touch of his teacher. “I know you Rumble. You don’t want to cause problems, you just want to fit in. Silver, Silver Spoon makes that easy for you, but it can’t be so one sided. You need to stand up, show her you’re a part of your relationship, otherwise you aren’t fitting in with the one you love, you’re just their shadow, there because you have to be.”
He looked down, his fists clenched. They soon relaxed though, and he looked back up. “What do you think I need to do? And I mean… I mean to stop this, because I am tired of it.”
She smirked at him. “Well, I believe if your previous actions are any sign, I have been a very naughty girl.”
He swallowed hard and turned away. “Yes, yes I suppose you have, but little sluts,” he paused for a moment as she looked hurt, but a small gesture for him to continue bolstered his confidence to continue, “are very hard to punish.”
Cheerilee hopped off of the desk she had been sitting on. “Well, I guess I can go home teach, can’t I?”
Rumble watched for only a moment as she stepped away before grabbing the ruler from the blackboard and swinging it around. The sick crack sent a chill of excitement up Rumble’s spine.
Cheerilee jumped before placing her hands on her wide rump and starting to rub it, doing so in just a way to ride her skirt up even higher. “Sir! That is highly inappropriate.”
Rumble raised an eyebrow. “You came to school in the middle of the night, dressed as a hooker, and you think this is inappropriate?”
“Of course!”
He raised the ruler to her chin. “Well, two questions then. First, do you really not want this?” He hefted a sigh of relief internally as she bit into her lip and looked away. “Well then, the other one is, who’s going to stop me?”
She swallowed hard and tried to push her breasts forward, getting more of the nipples to show. “Please sir?”
Rumble’s eyes glanced behind him and a sick smile came across his features. “You see that whiteboard? I want ‘It is bad to dress as a whore and enjoy being fingered.’ written fifty times on it.”
Cheerilee chuckled a little bit. “Now Rumble, I’m happy that you’re having fun with this, but-”
Crack!
“Yeep!” She put her hands back on her bottom again and glared at her Rumble. “Yes sir.”
Another ripple went through his body as she blushed a bit. The magenta mare reached up with one hand to write, but the other reached back and now tried to cover her bottom with the skirt. Rumble came up behind her and blew into her ear. “Finally being modest?”
“I-It’s different. Before I was seducing you. I was in control. Th-thiis isn’t how it was planned.”
“But isn’t it better this way?” Rumbled stopped, the words feeling odd to him, as if they weren’t for her. He glanced down and bit into his lip. A quick glance back at Cheerilee allowed him to see her smirking. Is she still manipulating me? Oh Luna no! He shifted the ruler, this time to bring it right between her thighs.
Cheerilee screwed up the word she was on at the same time the wood caught against her nethers. “S-sir?”
Rumble smiled at the reaction and slowly ground it backward, sliding the stiff plank along her crotch. “I really hope you’re continuing with those. It isn’t like you have a reason to stop.” He pushed up extra hard and saw her shift uncomfortably on the stick, also causing her writing to get to the point of scrawling again. “And I expect neat work. None of your normal chicken scratch so you can be done faster.”
Cheerilee shot him a glare from the side of her vision before getting back to work. Rumble currently couldn’t believe his luck to be able to perfectly replicate the worst detention of his life. Of course, with added benefits, he thought as the ruler slid forward now, causing the sensitive mare to wobble a little. “What are you supposed to be learning here? And how are you failing?”
Cheerilee’s legs closed, but the ruler wasn’t about to magically teleport away from her pussy. “I-it says from being fingered, sir.”
Rumble stopped to think for a moment before nodding. “Alright then, a change in terms is necessary. If you can manage to not cum while writing this, the punishment ends. If you don’t though, you have to do exactly as I tell you until you finish again. Sound fair?”
“No… but kind of exciting.”
He shifted closer to her, pulling away her hair and blowing on her neck before licking it. “Good.” One of Rumble’s hands moved up her side, slowly making its way until it found the edge to her white blouse. Pulling the cloth away caused him to lick his lips before his fingers pinched the rigid nipple. A gasp escaped her and Cheerilee’s knees bent slightly.
A small sucking sound could be heard below him that was in rhythm with each push and pull of the ruler. A glistening coat of liquid started to coat the majority of the rough wood as Cheerilee’s breaths started to come in pants. “P-please sir, this is so wrong.”
Rumble smiled at the grin on Cheerilee’s face just before she yelped from her nipple being squeezed harder. The hand then spread out, slowly covering the whole breast before squeezing it in his strong hand. Her pants were a chorus to him as he continued to massage and tease her. To finally have a girl at my mercy… I never thought it’d be this exciting!
Cheerilee’s legs attempted to straighten, and it was only then that he realized that the lightning quick hands of a teacher had almost beat his tactics. She would have to stretch though, and he knew he could stop that. The ruler came away from her for a brief moment, only to come back with a wet, thick smack against her booty. Cheerilee’s knees dropped in time with his free hand.
Cheerilee let out a long, sultry moan as the ruler went back to its job, sliding easily between her lower lips, her juices having thoroughly coated the wood by now. A hand came against her thigh, working its way up, but she gasped as Rumble pushed his thumb into her tight rump. “N-no, that place is, nng.” She couldn’t even try to stand straight as her now free tits smacked against wall, her strength failing fast.
His other fingers wrapped around to squeeze her rear and moved down. The sweet scent of her arousal filled his nose and a one last shiver ran down him as his cock became as hard as it was gonna get. Rumble’s tongue slowly came out and ran along her rump before he simply nuzzled against the large pillow of muscle.
Each moment filled his ears with more eager pants and shivers from the body beneath him. In one final attempt to win, Cheerilee collapsed. Rumble fell with her and watched as the older mare pulled herself up, reaching for the last space on the board. He grabbed ahold of the ruler one more time and acted without thinking.
Cheerilee visibly stiffened as the plank of wood wedged itself between her thighs. She let out an outcry of pleasure as she forced herself to stay up, even as she shook and quivered. Rumble was right beneath her as this all happened and felt a few drops fall on him. One fell into his mouth and he noticed that it tasted slightly sweet. The stream that soon came though was not what he wanted.
He ran a hand over his now wet facial fur and tossed it away, though he was still damp. Once the ruler was pulled away, Cheerilee completely collapsed onto the ground. She glanced his way and chuckled. “You deserve it, you damn tease.”
Rumble scowled slightly. “How far am I going to have to go to get rid of that snark?”
“Well, you’ve got me for one more go. Let’s see what you’ve got.”
Rumble nodded and stood on shaking knees. “Onto the desk, now.” He slumped against the board as Cheerilee stood and sat, crossing her legs. He gestured for them to part and she shook her head. “You need to say it.”
He swallowed hard. I had practically been putting a toy in her a moment ago, so why is this so hard? And yet, he still had problems with the thought of actually doing her. His teacher’s sigh hit his ears and he scowled. She just got to finish while my cock is about to explode. “Show me your pussy!”
One of Cheerilee’s hands came onto his shoulder. “Maybe we should stop. You need this, but go too far and… you might hurt yourself.”
Rumble opened his mouth to respond, but couldn’t come up with an argument. He didn’t want to. He had been mean to her already, and now he wanted more of his teacher, not the naughty schoolgirl. He hugged her tight. “Thanks Cheer. I… I think this will help me.” He then jumped as her hand ran along his crotch.
“You still have this to be taken care of though.” She smiled slightly, her hand still rubbing the front of his pants.
Rumble bit into his lip before growing a big smirk. “You think I’m actually going to risk impregnating you or getting anything you have? Though, you are quite right, I do need to get off.”
“So, continue as is?”
He shook his head. “No. Instead, I want a show, so you’re going to fuck yourself.” He put the ruler in front of her face. “Meanwhile, I’ll do myself, and if I catch you watching me, it’ll be to the board again.”
Cheerilee smiled at him as her hands found themselves covered in her own liquids from the rod. “Silver is a lucky girl to have a guy like you.” She then placed the ruler against her crotch and let out a soft coo, the wood slowly rubbing against the folds. Her breath caught slightly as she pushed the very edge of the makeshift dildo in her. “I-it’s so big Rumble!”
Rumble smiled at the joke as he slid his cock out and let out a small grunt as he touched it. It twitched in the air, already screaming at him to ram it into her. A few deep breaths though, and his hand was decided as an acceptable substitute as he stroked the taut skin. His own breath started to become labored as Cheerilee’s cries became increasingly desperate.
Each movement of the rod came with Cheerilee shaking a little, as if electricity was arcing through her body. She still only had a few inches in, but her acting made Rumble think she was being done by three stallions. “I-it’s so good. I can’t believe what you can do with, nng. Ma-maybe a little to the, Oh yes!”
She started to thrash on the desk, the hand not dealing with the ruler grabbing ahold of one huge breast. She forced it up, her eyes fixed on the pink nub on her body. Her lips barely enclosed the nipple before she threw her head back, forcing the breast to stretch even farther. Rumble saw the large mound quiver and shake as her muffled cries became louder and louder.
Rumble’s own pace tried to keep up with the frantic thrashing of his partner. Loud slaps could be heard as his balls swung against his thighs, a casualty of just how fast he was stroking at this point in anticipation. He started to see decent bit of clear liquid on the tip of his member appear and hoped she was close to being done.
Cheerilee’s free hand left the top of her body and she forced herself to take one more shuddering breath as she looked past the mound in her face to look at the desperate stallion who was panting against the blackboard. Her own body shook with anticipation, knowing its master could finish her off in one moment. Just… a little… longer, for him.
The pressure was too much and Rumbled finally gave up, thinking it was a race he was doomed to lose. His pleasure spiked as he grip his large, throbbing member. At this same moment, an ear piercing scream filled the air.
“Rumble!”
He felt himself spike even harder as the primal cry met his ears and the mare in front of him gushed her own fluids across the table and onto the ground. Rumble focused it forwards and went back one more time before pushing it all forward. Thick, white strands of cum flew through the air and landed on Cheerilee’s lewd body as she spasmed and shook on the table. Meanwhile, Rumble simply collapsed to the ground, ignoring the liquid that covered the floor.
After a few minutes of quiet panting, Rumble stood. Cheerilee opened her eyes and tried to lift herself up slightly. “Wha-what are you going to do?”
He looked into the distance and groaned. “I have flowers and chocolates to buy. If I hurry, I can get back to Silver’s before she does and make me her one and only valentine this year.”
‘And if she says no?”
He smirked. “I have no idea, but I don’t plan on ‘okay’ being my answer to that. Not anymore.”
Cheerilee closed her eyes and listened to the door softly close. “Good luck Rumble, you’re going to need it.”
/\
/ \ /\ /\
/\ / \ / \ / \
/ \ / \ / \ / \
_________/ \_____________/ \___________/ \___________/ \______________
Author's Note
Sorry if I didn't quite deliver well on the fetishes. I'm still working on some, and admittedly, these are not my strongest and criticism is always welcome.
Next Chapter