Author's Note
What lies ahead: Awkward conversations (Cheerilee and Filthy Rich) Straight Shipping (Cheerilee x Filthy Rich), Sexual Intercourse (Cheerilee x Filthy Rich)
Bad Teacher
"Miss Cheerilee! Do we have homework?" Sweetie Belle asked, her hoof raised.
"We never have homework on Fridays." The magenta earth pony smiled. "You know that Sweetie Belle."
"I know. I just like to make sure." Sweetie clasped her hooves together and grinned gently.
"She only wants to do homework because she's got no plans," Diamond Tiara snickered to Silver Spoon. Her best friend giggled and Cheerilee glared at her.
"Well lunch is almost here," Cheerilee announced. "Everypony grab their lunches and head out to the cafeteria." She stood up and picked her own paper bag of lunch up and guided the children outside. She seated herself at an empty table and fished a sandwich out of her bag. The Crusaders plopped down next to her, a smile on their faces.
"So.. Hearts and Hooves Day is coming up again," Sweetie Belle fluttered her eyelashes, pressing herself close to her instructor.
Cheerilee nodded and smiled. She swallowed a chunk of her sandwich. "Do you have your eyes set on any young colts?"
"No.." Apple Bloom shook her head, leaning in.
Scootaloo batted her tiny wings with thought. "We're wondering if you have your eyes on any colts."
"Girls.."
"Aww come on Miss Cheerilee," Apple Bloom urged. "Ah know it was bad last year but this year you can really fall in love. Don't you want a little compassion in your life?"
"I will discuss this topic no further." Cheerilee pounded her hoof on the table lightly and tore another chunk out of her veggie sandwich. Lettuce lingered in between her teeth as she squashed rye bread into mush.
"Sorry Miss Cheerilee," they all apologized in unison.
Scootaloo poked at her own PB & J sandwich.
An awkward vibe spilled into the air. Everypony at the table was silent. The ponies around them were chatting and babbling away carelessly in the midst of munching on their meals.
"We'll just go sit over there.." Scootaloo sliced through the dead-air and scampered away to the next table.
Cheerilee peeked at them with her green eyes. She crumpled the remains of her sandwich into a ball and stuffed it back into her bag, which tore a tiny bit from the impact. She pulled out a squirt water bottle and squeezed it into her mouth.
She watched the children talking to one another. Even the Crusaders had thrown aside their unusual, quick conversation with the teacher and had started talking to Archer and Pipsqueak.
She sighed, squirting more water into her mouth. Her eyes ran over Twist, who was sharing lips with Truffle Shuffle. Their hooves were wrapped strongly around each other in a hug, but their kiss was still school-yard friendly. No, it wasn't the common peck on the cheek, but they weren't grabbing each other's asses and twirling their tongues into each other.
She squirted again. Her lips were now shaped around the top of the cap, the tip of her tongue lightly pressing against the top of the hole that allowed water to pass through. She squeezed the plastic bottle with her hooves. Water surged into her mouth, pouring down her throat. She released the bottle and licked her lips softly. She then pressed the bottle to her lips again and gave it another squeeze. More water traveled into her throat. She continued to squeeze and indulge in the water until..
"Miss Cheerilee!"
Cheerilee dropped the bottle to the ground and wiped her lips. She looked down at the little white unicorn standing in front of her. "What is it Sweetie Belle?"
"I think lunch is over." She pointed to the clock that hung loosely above the entrance to the schoolhouse. "What were you doing? You seemed like you were in a daze."
"Oh nothing." Cheerilee bent down to pick up her trash. She dropped it in the nearest garbage pail and tossed the rest of her bagged lunch into there as well. "Just enjoying some nice water."
"Okay!" The filly ran to the door and waited for her teacher to follow.
"Come on children!" Cheerilee directed. Everypony stood up quickly. The ones who had their lunches in bags tossed them away. Diamond Tiara and Silver Spoon held their shiny, Equestria Girl lunch boxes in between their teeth proudly, as they sashayed to the top of the line.
The rest of the day rushed by. The children were happy when the teacher finally glanced at the clock and saw that it was time to leave. The three Crusaders staggered behind the crowd of rushing "Friday-high" fillies and colts and stopped at their teacher's desk.
"Well hello girls.. Again." Cheerilee chuckled and then blushed. "Sorry for the awkwardness from before."
"That's okay Miss Cheerilee," Scootaloo replied.
"We understand," Sweetie added with a nod.
"But remember to think about it." Apple Bloom winked, as the trio burst into laughter and scampered away mischievously. Cheerilee pretended to laugh along but when they left, she let out a sigh. Her heart lurched as she sat back down, the pile of schoolwork sitting on her table in a cluttered stack.
She grabbed one paper and checked it. Sweetie Belle's.. "A". Cheerilee smiled a tiny bit to herself.
"Like usual," she commented quietly, grabbing another paper. Truffle Shuffle's was sticky with some type of food (he always had some kind of snack to munch on). Cheerilee moistened her hoof a bit and tried to scrub the smudges off to little avail. She marked with a "A", as well, and picked up another sheet, which was on the wrong side.
"omg when is class getting out" Diamond Tiara had scribbled on the back to Silver Spoon.
"i dont know miss c is taking for ever" the silver mare had wrote back.
Cheerilee flipped the side of Diamond's sheet over. Some of the answers were correct and some were incorrect. Half-assed, like usual. She marked a "C" on the paper along with a "Try a little harder!" It didn't matter. Half the time Diamond Tiara didn't even show her father the papers she did from school.
An hour went by, the sun dropping over the horizon. Cheerilee loaded the papers into her file cabinet, standing by the desk, and trotted home with her tiny flashlight between her teeth.
The light emitting from the device allowed the mare a clear walk home, the sky becoming darker with the setting sun. Ponyville glistened and mothers ordered their fillies and colts to come inside for supper.
Cheerilee was too busy admiring her town when she bumped into somepony.
She dropped the flashlight to the ground and it flicked off thanks to the impact.
"Oh! I'm so sorry Rich."
"That's quite alright Cheerilee." The uptight business stallion brushed himself off, though it was quite obvious that the mare he bumped into was not dirty.
"I wasn't paying attention.. I was just admiring the children and-" Cheerilee glanced at Filthy Rich and from the look in his piercing eye, it seemed like he was either bored or he already understood. She chuckled awkwardly for no reason and pointed to her flashlight. "I dropped my flashlight."
"I see." Filthy Rich nodded, his emotion unmolested.
Cheerilee realized how stupid she sounded. "I'm going to pick it up now." She scrabbled to the floor and picked up her flashlight, feeling eyes burning into her skin.. For some reason.
"So.. How is teaching?"
The mare shot up, the flashlight in her teeth. She dropped it into the saddlebag she was carrying. Looking behind her, she noticed Rich staring at her.
"It's well." She flashed an uncomfortable smile and looked in front of her. "Weren't you just standing over there?"
"I was."
Cheerilee raised an eyebrow, but before she could question anything, Rich spoke before her.
"Is my little filly doing okay in school?"
"She just got a 'C' on her latest paper." Cheerilee winked. "Not too be rude, Rich-"
"You can call me Mr. Rich." He walked slightly closer to the mare.
"Um.. Okay.. Mr. Rich.. Shouldn't you be with your daughter right now?"
"She goes straight to Silver Spoon's house almost everyday from school. It's so close to the school, rather than walking all the way down from the schoolhouse to her mansion here." Rich was eyeing the teacher all over, his icy blue eyes venturing every crevice. "Keeps her out of my mane for a good hour or two."
The mare waited a moment in the silence. She could feel Filthy Rich's breath softly on her neck as he crept nearer. "Well that's good to hear. I'm going to head home now. Thanks for the chat." Cheerilee turned around but the stallion rested a hoof on her back.
"Wouldn't you like to come with me? It's not very polite to let a mare like you walk alone in the dark. Something could happen."
"I know my way around Ponyville. But thanks for the offer." She turned away again but this time was pulled back. She blushed as she was taken under the hoof of the older stallion. Their coats touched warmly, as Rich walked her into his mansion.
As they stepped inside, a Persian white cat darted past the two's hooves. It looked much like Opal, only it had a diamond studded collar and blue eyes instead of green.
"You'll have to excuse me if it smells a bit like cat in here." Rich whiffed the air and inhaled deeply. He exhaled onto Cheerilee's neck. "My daughter demands we keep her even though she doesn't give a rat's ass about the feline."
"Oh.. Well.. Okay then," Cheerilee replied slowly. The two walked up the stairs and were greeted by a mare with a feather duster in between her teeth.
"Hello Mr. Rich," she said, putting the duster onto the table.
Filthy Rich tipped his head as to say "hi" and padded into a clean, white living room. The walls were white along with the couch, and the hoof-rests were also the matching color.
"Sit," he offered, pointing toward the couch.
"Thanks." Cheerilee plopped herself down and Rich followed her, wrapping his hoof around her neck and throwing his back hooves onto one of the hoof-rests.
"So have you always liked teaching?"
"Of course! I've always wanted to teach, ever since I was a little filly." Cheerilee tried to use this common-day chatting to steer away from the stallion, but he pushed her snugly against his side.
"I've always wanted to earn money." Rich smirked and looked down at the mare beside him. "Ever since I was a colt."
"That's very interesting." Cheerilee coughed to clear some of the stuffy-air. "It's good to have bits in your pockets sometimes."
"Well I have it all the time." Rich laughed warmly at his own joke, although Cheerilee squirmed a bit. She couldn't honestly relate to it because it wasn't like she was extremely rich. Sure, she had enough to get by, but not to throw away. "So you're awfully quiet, huh?"
"I think you're mistaking me for Fluttershy. I just don't talk when I don't have anything to talk about."
"Well maybe this will give you something to talk about." Rich leaned over and kissed Cheerilee on the lips.
She stood awe-struck, the moistness from the quick kiss still on her lips. It escalated so quickly that Cheerilee was overwhelmed.
"Did you just kiss me?" she asked, trying to scoot away from his more. His hooves had moved down to her hips and were holding her pressed against his side.
"Well what did it look like?" Rich was still remaining perfectly calm, like nothing out of the ordinary had just happened.
"But-"
"You did enjoy it, didn't you?"
Cheerilee noticed he was staring at her again. She felt her cheeks burning hot as Rich's hoof slid around her flank and up her thigh. "I'm not-" She squealed when Rich ran his hoof over her butt.
She stood up, her nostrils slightly flaring.
"Mr. Rich!" She tried to keep her volume down but still thought that the stallion should deserve a proper punishment. "I am not a sexual toy for your amusement! You're nearly ten years older than I am!"
Rich didn't do anything. He shifted his lips a bit and let out a heavy exhale. "Criada!" he suddenly called in what seemed like Spanish.
Criada, the maid pony, rushed in and tipped her head. "Yes Mr. Rich?"
"Could you fetch my box of cigarettes and a lighter?"
"Yes sir." She dipped her head again and sped out of the room.
Cheerilee wasn't sure why she was still standing there, but she felt if she moved, things would get more awkward.. In a way. So with her face flushed crimson, she stood planted to the white, smooth carpet.
Criada came back with a pack of Menthols and his gold lighter and handed them to him. He took one slender, stick out and put it between his teeth. "That's all."
"Very well." She walked out of the room.
Rich looked back at Cheerilee as he lit the end of the cigarette. The heat started to slowly disintegrate the end, smoke flooding out as the result. "Is there a reason why you rejected my gesture?" he coughed.
Cheerilee was still glued to the floor. ".. Well you're older than me. And.."
"And?"
"Do I really have to go through all of this? It's already getting late."
"No sense walking home now." Filthy Rich blew hard on the stick and took it away from his lips. He coughed a ball of grey smoke from his mouth. "It's nearly 5 o'clock."
"That's fine. I can walk. It's not too dark yet."
"You know just as well as I do that's a lie, Cheerilee." Rich was intently looking into her eyes, but she tried to hide that she was looking into his as well. "You needed a flashlight just to get home."
"Well I still have the flashlight." She felt like darting out the door to escape. Making this monotonic conversation wasn't elevating her any further to her release.
He shrugged, puffing out another ball of smoke that smashed into the ceiling. "Feel free to go home. I do have a guest bed, if you would prefer not to sit alone in your house."
Cheerilee swallowed. "No."
"Sleeping in a guest bed does not mean I am going to have sex with you." Filthy Rich pounded his chest to clear some smog out of it. "If that's what you were thinking."
"Uh.. Er.. No," Cheerilee quickly stuttered. "I.. Wasn't thinking that." She popped her knees a couple of times. She couldn't force herself that she didn't want to stay here. She did want to, her mind just refused to accept that. She felt warm being around Rich but nervous at the same time. And.. She was a little lonely. Maybe it wouldn't hurt.. "Anyway, I suppose I could stay here." She sat back down on the couch, hoping Rich wouldn't hold her again, but she was mistaken. He wrapped his arm around her lower back again and puffed on his cigarette.
"Can I.. Uh ask you something, Mr. Rich?" she inquired quietly.
"Of course."
Cheerilee squirmed a bit in her position. "H-have you always found me attractive?"
Filthy Rich took the cigarette from his lips again but this time turned to the side. A clay-made ash tray sat in the middle of the table. He squished the cigarette into the tray, killing the flame that simmered inside. "Well Cheerilee.. You have always been a most beautiful mare."
"Uh.. Um.. Thanks." Cheerilee flattened her ears and felt more blush coming on.
"Your pink mane," he continued. "Your well built figure. Your pretty eyes. And I have always had a fetish for your butt."
A mixture of rage, embarrassment, and compassion clashed inside her stomach. Butterflies choked her throat on the way up, but she remained silent.
"I very much wish to see more of you.. Eventually. Perhaps when you decide you're ready for sex with an older stallion."
Cheerilee felt very uncomfortable. She wanted to break free of his grasp and run, but she had agreed to stay.
"So.. Let me ask you Cheerilee: Do you prefer anal or pussy?"
"M-Mr. Rich!" Cheerilee gasped at the use of his vulgar language.
"It's just a simple question."
"But why?"
"Well when you do decide you're ready, I want to find out what pleasures you most," Rich said dully.
How do you know I'll ever be ready for you? Cheerilee steamed. She calmed herself down, though, and took a few quick breaths before answering. "I.. I never really have had anal.. Or 'pussy'."
"Ah. A virgin I see."
The mare blushed again as somepony walked through the door.
"Hello Diamond Tiara," Criada greeted.
The filly ignored her and walked into her room immediately.
Cheerilee hoped to steer the conversation from sex. "Doesn't your daughter ever say 'hi' to you when she gets home?"
"No. She just walks to her room." Filthy Rich shook his head. "So back onto our topic."
Cheerilee let out the tiniest groan.
"If we were to have sex, would you be willing to try a little of both category?"
"I don't know.."
"No need to be shy Cheerilee. We're adults. Adults talk about sex. It's perfectly normal."
"I need some rest." Cheerilee quickly stood up, the conversation getting too creepy for her.
"I'll guide you to the guest room." Rich grabbed her hoof and led her down the hallway, passing a couple of other rooms. Diamond's door was a crack open, and she was dancing to "Anaconda", the newest pop music song from mare rapper Big Booty.
"I don't know why I let her listen to that shit," Rich grumbled to Cheerilee as he heard the lines "gun in my purse, bitch I came dressed to kill. Who wanna go first? I had them pushing daffodils. I'm high as hell, I only took a half of pill. I'm on some dumb shit." "Anyway, here's the room." He pushed the door open with his nose.
Cheerilee sat down on the bed and dived into the covers. Rich smirked as he flicked the light on. "Can I get you anything before you head to sleep?"
"No thank you.. But thanks." Cheerilee closed her eyes. About a minute later, she felt pressure weigh down the mattress. Something heavier than herself lied over her, hooves stroking her mane.
"G-Gah! M-Mr. Rich! Get off!" Cheerilee felt his legs in curve with hers, although hers were under the blankets.
"Don't you worry, Cheerilee. I'll be gentle with you." He pulled the covers out from under himself and from over her, as his right hoof caressed her body smoothly. It went over every curve the pony had, every crevice. "Such a nice frame.. And so young, too."
Cheerilee tried to squirm out. "I barely know you!" she argued. "Your weight! It's hurting me!" She grunted as Rich flipped the mare onto her back more appropriately, exposing her thin belly.
"Is that a little better now? Wouldn't want your first time to be painful." His back legs were now spread to either side of of her own, his slightly stiffened penis head pressing against her pelvis softly.
"I'm not ready for my first time." Cheerilee felt his cock hardening on her lower body as he resorted to her neck, grasping onto the nape of it with his teeth. They clenched the gentle skin on it, making the mare wince.
"Just calm down, Cheerilee. This isn't even the part that's supposed to hurt."
"Well it does!" she snapped, not feeling how this was romantic at all. It felt more like rape than romance, in her opinion. Rich continued on, though, his teeth sinking into her soft coat.
"Just relax.." he offered, feeling her tenseness in her skin.He wrapped his hooves around her back and slid them up her spine. He brought his lips to hers, locking in for a kiss. His tongue wrestled with her own, fighting over control of the mouth. Rich's hooves slid over Cheerilee's ass again, but this time, she couldn't yell like she had done previously. Her mouth was trapped within another mouth that would not let go.
I can't do this.. He's so old. Cheerilee thought, her eyes wide open and staring at the stallion on top of her. But.. Wow.. This kiss. I can't believe I like it a little bit.
Rich's hooves rode over Cheerilee's slice that cut off her two butt cheeks. In between those butt cheeks was a perfectly penetrable hole that the stallion was longing for. He finally let go of the long held kiss and breathed heavily. "So did you like that kiss, compared to the one in the living room?"
Cheerilee blushed and couldn't help grinning the tiniest bit.
"You know you did." Rich stroked her mane and brought his head down to it, inhaling a whiff of the cotton-candy colored head piece. "Delicious.."
"I'll admit that was a little-" Cheerilee paused herself to breath. The kiss was held so long, she thought she would get enough air back into her lungs. "-It was a little sexy.." Her ears pricked up when Rich's head got to her ear. He was sniffing her mane, licking his lips as he went.
"Alright Cheerilee. Since this is your first, I'm going to walk you through everything. And if it hurts a little, moan it all out."
Cheerilee felt her vagina lips clenched together in fear.
Rich reached his hoof down into her pussy, which was semi-moist with "lady juice." "No need to tighten up," he said. "Doing it in the vagina usually doesn't hurt as much as anal."
You said usually!
His hoof slipped through her lips and swiped gently across her sopping clitoris. By stroking it, he caused more juice to leak from her. "Getting excited?"
Cheerilee nodded a tiny bit, although fear still churned in her stomach uncomfortably. It was all just happening so fast. One minute she had been walking home. Filthy Rich insisted she come to his house, they were having an awkward conversation, and now they were in bed together. The mare was so confused about the sudden events that just seemed to flash by her life.
Rich grasped onto Cheerilee's belly. He lifted his haunches along with his hips and brought his cock down to her slit. The tip touched the opening gently and the mare squeaked a little bit. No words. Just a squeak of randomness.
His penis pushed into her vagina slowly. Hotness rushed up Cheerilee's stomach and exploded in her head. It wasn't as bad as she expected, but it still burned like hell fire. Rich kept pushing it in further and Cheerilee let out a series of moans.
"We've still got more to go. Moan if it hurts."
Cheerilee let out a few moans. Fear that was in her stomach mixed with pain that shot up her body. Her eyes forced themselves shut while Rich pushed harder, getting some of her vaginal cum on his meat stick.
"Almost in there." Rich felt himself getting harder, as the walls of Cheerilee's meaty pussy enveloped around his dick. He reached his limit and let out a sigh, resting his penis in her for a few moments.
"You made it. That part was the most painful, so don't you worry." He patted her mane, which was slightly damp at the base from the previous events. "It didn't take so long, now did it?"
Cheerilee let out some shocked breaths, still shocked that a cock was inside her right now. Physically inside her body. "It.. It was painful.."
"It can be at first. But once you've practiced a couple of times it will stretch out," Rich informed her, still stroking the base of her mane. "Next is just the simple orgasm. It seems you have already started."
"Yes." Cheerilee blushed.
"Now it's my turn. So again, I'll guide you through it. And don't worry. This part doesn't hurt nearly as much."
She took a few more inhales of fresh air and let it out slowly. "..Ready when you are."
"I see you're adapting well for your first time."
For Celestia's sake, are you going to mention you're my first for the fifteen billionth time?
Rich hooked onto her belly with his hooves. He felt his cock twitch inside Cheerilee's moist marehood, as he plunged it and out slowly. It slushed about in her giving pussy, cum leaking onto it from her urethra.
Cheerilee felt horny urges being soothed by the older stallion's genitals penetrating her own. The gentle "slush" sounded as he removed and inserted his erected member into her several times. Sperm rose in his meat stick as he did so, hoping to explode to the top.
Every hump sent Cheerilee's head flicking back slightly from the impact of a penis slamming into her. Every time Rich pulled it out, it was covered with more substance than the last time.
"F-faster," Cheerilee urged.
"Getting more horny?" Rich bounced an eyebrow with a smirk as he quickened his pace in the fucking. His dick was growing warm with the substance that was trying to escape out of his tip.
Cheerilee spread her legs further, allowing the penis to move more freely and rapidly through her. Every move made was shared between the two ponies.
Rich grabbed more of her stomach for more a better hold. He lowered his haunches, slamming more of his long cock into her.
"Rich!" Cheerilee was breathless with delight, her tongue nearly falling out of her mouth. Drool dropped from it onto the bedspread. Her eyes forced themselves shut, not standing to witness the scene.
The stallion's hooves moved down toward her pelvis. He elevated his pace again for one last run before he pulled out. Cum wanted to rush out of his cock. Complying with the needs of his body, he pulled out and pointed his dick with his hands at the mare lying down.
Thick, gooey sperm spewed out of the hole in his tip and onto Cheerilee's stomach and other body parts. She closed her eyes lightly this time, as his load emptied onto her, slowing down as he ran out.
Sperm lingered everywhere on the pony. She opened her eyes wearily, her pussy sore. Rich was staring at her, that cocky-ass smile on his face. He let go of his dick and let it get soft again. He sat down on the edge of the bed, Cheerilee resting her legs from keeping that up during that twenty minutes of sex.
"You're a little messy."
Cheerilee giggled a tiny bit and picked some of the sperm off her stomach. It was in her mane, near her eyes, and some had even ventured to her flanks.
"So you enjoyed it?" Filthy Rich asked.
The mare couldn't speak. She was so breath-taken by the few moments that flashed by that she just nodded.
"Good." Rich smiled, satisfied with himself. "Hope I didn't cause you too much pain."
Cheerilee rested a hoof on her moist chest and grinned a little.
"I see you're tuckered out. When you start with a big cock like mine, that will usually happen." Rich flopped down beside her, feeling her mane again. It was drenched in sweat with a mixture of sperm hanging off the tips. "Would you like to take a shower to clean some of that off? I'll have Criada clean this up."
The mare nodded but her body wouldn't allow her to get up.
"Feel free to rest." Rich dragged her close to his own sweaty coat with his hoof and smiled. "I'm always there to help if you want to.. Er hem.. Stretch yourself out."
Cheerilee nodded. That was okay..
She guessed.
