Cheering Up Cheerilee

by Krystal Clearskies

Rating: everyone
Tags: Cheerilee, My Little Pony: Friendship is Magic, Romance, Original Character, Comedy
Length: 3342

Walking through Ponyville one day, you see a distraught Cheerilee. Deciding to help her, some interesting times ensue.

One day, while walking through Ponyville, you see a distraught Cheerilee, crying at the school house. Deciding to be a good friend, you stop to help her.

Tagged romance for some kissing at the end!

Published 2016-07-19 04:10:01 UTC
Last updated 2016-07-19 04:10:01 UTC

Cheering Up Cheerilee

Author's Note

Hello, Everypony! So, lately I've been doing a lot of reading here on FIM, and I've become enthralled with stories involving OC characters and characters from the show romantically. I figured I'd give one a shot.

I wrote this at about 5AM, so if it sucks badly, please let me know, and tell me what I can do better next time.

Enjoy!

Cheering Up Cheerilee

One day, you trot silently through the desolate streets of Ponyville, two saddlebags attached to your hips, each filled to the brim with groceries, necessities for your home on the other side of town. It was quite a trek to your home, about thirty five minutes from the marketplace.

Alas, twas the price of owning property in such a sought after town such as Ponyville. Ever since Castle Friendship appeared, the real estate market has sky rocketed prices, as everypony seeks to live close to Princess Twilight Sparkle. That was something you never understood before, why so many ponies idolized celebrities. Idolizing the Sister Princesses was one thing; but to you, Twilight was little more than a celebrity.

Anyway, the only way to attain land in Ponyville was to live on the very outskirts of town, not far from Sweet Apple Acres. It was quite the inconvenience, living so far from downtown Ponyville, but to have estate in the quaint town was worth it.

Finally, you reach the front door to your home, snapping you out of your trance inducing thoughts. You use your magic to levitate your key in front of the keyhole, and use your magic to undo your lock. Walking inside, you use your magic once again to close the front door and lock it. You then walk into your kitchen and unload your groceries, humming a light tune to yourself as you did so.

When the groceries are put away, you gasp as a realization hits you. “Oh Ponyfeathers!” You curse under your breath. All of that shopping, and you forgot the most important item; Flour, for your baking!

Walking to the front door, you unlock and open your front door, relocking it thereafter. Cursing under your breath, since you know it was going to be a long walk, you begin your excursion with a heavy groan.

At some point along the way, you get into a deep through about why you weren't very skilled in magic. Sure, you could levitate items and do other essential actions every unicorn should know, but beyond that, you were a stranger. You then think how easy it would be to simply teleport yourself to the market and back. You would save much valuable time everyday. Perhaps Twilight could tutor you, if you ask very nicely. Twilight was known for having a love for teaching magic.

You're snapped out of your thoughts as you hear a voice. Not being able to tell where the voice was coming from, you settle for just listening to it for now.

“Oh no, oh Celestia! This is not good!” A feminine voice says frantically. Using your ears to pinpoint the direction of the voice, you gallop to the Ponyville School house, which was not far from where you were. You get there, to see a heavily distraught Cheerilee in the yard.

Taking a moment to study her, you see that she is holding a stack of folders in her hooves. You also see that many folders are scattered on the ground. You raise your right eyebrow curiously, and walk into the schoolyard.

As you do so, you begin to think about Cheerilee. You knew about her, of course. The teacher of the school children, the one who's always smiling, the one who always seems happy no matter what is happening. That fact startles you; she was always smiling and happy. The fact she was frowning currently, and very distraught sent shivers up and down your spine for a moment; something had to be wrong.

Walking up to her, you survey her before speaking. Her mane was different; instead of it being uniform and curly like it usually was, it was right now ragged with splits in it, an obvious sign she is very stressed out.

Finally, you speak to her.

“Mrs. Cheerilee? What's the matter? Why do you look so distraught?” You ask her in as soft and caring a voice as your husky vocal chords could muster.

She turns her body to look at you, and you see for the first time her bloodshot eyes, bags wrinkled underneath them like bad, crinkled pillows. She finally replies after what feels like an eternity.

“Oh Candle Wick, it's terrible! The supervisor of education is coming here from Canterlot tomorrow for an assessment of my little ponies' learning progress and my competency as a teacher. I have to prepare writing samples from each of my students for her to look over and assess, as well as write a five page paper of why I enjoy teaching, describe my methods for teaching my little ponies, and so much more!”

She stops speaking, as a tear falls out of each of her delicate eyes. “I'm quite frankly having the worst day I can remember. It's been a nightmare trying to find adequate writing examples my little ponies have written! If I don't succeed in this, I could very well be fired from my job! I can't get fired, I can't see myself doing anything but teaching! And if I get fired, what will become of my little ponies? Who will teach them? Will they like their new teacher?! I am so stressed out thinking about it!”

She suddenly falls to the ground, sitting on her flanks as she appears to have a bit of a breakdown. She brings a hoof up to each of her eyes as she starts to sob. Immediately, as you take in this sight, you feel something in your heart. You feel an insane amount of pressure, like somepony was squeezing on it with both their hooves. You feel immensely sorry for Cheerilee and in one instant, you sit next to her on the ground.

Not wanting to invade her privacy, instead of hugging her, you use your hoof to stroke her frazzled mane as gentle as you can, and speak to her in the most soothing tone your throat can muster.

“Mrs. Cheerilee, please don't cry! I'm so sorry you're having a hard day, but I promise you it'll all be okay. I'll help you with this!” You say in as reassuring a tone as you can. She stops sobbing for a moment and looks at you, wiping the tears away from each eye.

“You...You mean it, Candle Wick? You'll help me?” She asks you with a bewildered look it her beautiful eyes, they seemed to be filled with hope, a glint of slight happiness.

That look in her eyes gives you strength, and with a smile you swipe your hoof over your heart.

“Cross my heart.” You start, as you do the swiping motion.

“Hope to fly.” You continue as you use your hooves to make a fluttering with them.

“Stick a cupcake in my eye!” You now have a headache as you finish the Pinkie promise. It's then that about twenty foot away, you see Pinkie Pie herself in the bushes. She glares at you with a serious face and points both hooves to her eyes, before rotating her wrists to you, letting you know she's watching you. With that, she bounds away back to town, singing to herself happily.

After taking a few moments to gather yourself after that random Pinkie Pie debacle, you look back at Cheerilee just in time to see her smile. That smile instantly brightens up your world.

“Thank you Candle Wick. I can't even begin to tell you how much this means to me.” She says with that happy chirp back in her voice. It seems that for now, she was back to her usual cheery self, hence her name.

“No problem, Mrs. Cheerilee. Let me first ask, what's with all the folders? Why are so many scattered on the ground?” You ask her, and she looks at the playground where so many vanilla paper folders have been laid down.

“Well, see, those are all filled with those writing samples I mentioned. I was going to bring them home to evaluate them, and make sure they were adequate to show to the education supervisor. But fate sent a wicked breeze my direction, and they all got scattered! Can you help me get them back, Candle Wick?” She asks you, and you smile at her, giving her a deep, reassuring nod.

“Of course! Let's go herd up some folders!” You say as you stand up, galloping to the first one in front of you. It was about ten feet from where you were sitting.

After that, you shift your walk left ways, scooping up another one. After that, you climb up the jungle gym, collecting the next one which sat on top of a slide. The nearest one after that rested at the crest of the other, tallest slide.

Walking up the stairs to the slide, you extend out your hoof to retrieve the folder. However, just as you are about to snake the thing, the wind suddenly blows it to the bottom of the jungle gym, in the bark below!

“Rats!” You say to yourself, as you survey your options. Jumping off of the jungle gym would only pose the potential of injury. Going back down the stairs would take too much time.

That's when suddenly, without thinking further, you gallop forward once, falling to your stomach and careening down the large spiral slide head first! To say this was terrifying would be an understatement. Because you're a full grown stallion, you barely fit in the slide, andyou bump your noggin on the plastic edge of the slide numerous times, and you're pretty sure you'll have a wicked headache afterwards.

Finally, you get to the bottom of the slide, albeit dazed from hitting your head. Remembering the folder was at the very bottom of the slide, you reach out to grab it.

Your hoof however, grabs nothing but thin air. With a gasp, you shimmy your eyes left and right, trying to see where the folder went. That's when your eyes settle on Cheerilee, who is standing a few feet in front of you, folder in hoof.

She looks at you for a few moments before she brings her hoof to her mouth, letting out muffled giggles from your ridiculous, amusing antics. You laugh with her at yourself, rubbing the back of your neck a tad bit sheepishly as you realize how unnecessarily brash you acted.

As you laugh, Cheerilee removes her hoof and lets out some loud, infectious laughter. Her laughter only makes you laugh harder, until you're both nearly guffawing on the ground.

A few minutes later, you and her finally stop your fits of laughter, and she wipes a few tears from her eyes. She actually laughed so hard she cried, a smile now plastered on her muzzle.

In the next while, you and Cheerilee walk around the school grounds, collecting the folders from rather peculiar places such as the windowsill, the merry go round, and even the oak tree nearby.

When you finally hoof over all the folders to Cheerilee, she gives you as big a smile of appreciation as she can muster.

“Candle Wick, thank you so much! Now I can go home and get this work done. You might have just saved my teaching career!” She says happily.

“Though, I hate to ask more of you. But is there any way you could help carry these folders to my home? They're surprisingly heavy!” She informs you as she's about to drop some of them. You quickly scoop up half the pile from her hooves, and you walk with her side by side to her home.

Her home is actually not far from yours, maybe five plots of land away from it. As you get there, she unlocks the front door and steps inside, turning on the light switch with her rump. Thankfully it was rump-level. You smile and walk in behind her, setting the folders down on her desk.

She does the same, and sighs in relief as she's no longer carrying that heavy load. “Oh Celestia... in one night, I have to read about thirty-three essays, and write a five page essay for the supervisor. This is going to be one long night!” She exclaims with sadness in her voice.

Suddenly, a thought comes to you. “Mrs. Cheerilee?” You asked her, and she looks at you.

“Candle Wick, you don't have to call me Mrs. We're both adults. Please, call me Cheerilee, ok?” She asks you, and you give her a nod.

“Mrs... excuse me, Cheerilee. What if I stayed here and read some of the essays for you? I have nothing better to do tonight, and it would help take some of the load off of you. Seems to me you could use any help that you can get!” You tell her.

She looks at you, truly shocked and surprised by your generous offer. After what felt to you like an eternity of her debating, she nods.

“Yes, I suppose you're right, Candle Wick. I can use all the help I can get. But are you sure you don't mind? You don't have to do this.” She says sadly with her ears dropped down. You shake your head.

“I don't mind one bit, Cheerilee. It's my duty to help those in need, just like Mayor Mare did when I need a home to stay in.”

With that, you grab a stack of the folders and sit at her kitchen table, getting to work on reading them, to make sure they're presentable material for the supervisor. Cheerilee explains to you that, in simple form, the essay simply needs to sound well written. If it flows well, makes sense, and has no obvious spelling mistakes, it's good to show.

So you get working with your reading. You read some very interesting essays, such as one from Scootaloo on why Rainbow Dash is the greatest pony who ever lived, stating reasons for her position, such as she's twenty percent cooler, a wonderbolt, the bravest pony ever, just to name a few. Another one was from Apple Bloom on why it's better to plant apple tree seeds in moderate weather than hot weather, so as to not get too thirsty and tired.

You chuckled a bit. While the childen were simple minded, they were far smarter than most gave them credit for.

You pick up another folder and read yet another essay. This one was from a filly named Peppermint Twist on why pure peppermint was better than wint-o-green for candy cane sticks. Then another one, which detailed the perils of being an amateur photographer. That child forgot to put their name on their paper.

It took many hours for you and Cheerilee to finish the reading, but finally, you hoof over the last of your essays. She finishes up her last essay not long after. You both had bags under your eyes and were both insanely tired, this was very evident, clear as day.

She does smile at you, however. “Thank you so very much, Candle Wick. You're helped me so much today, and I WON'T forget it. I promise you.” She tells you with her smile wide, and you smile back.

“You sure there isn't anything else I can do, Cheerilee?” You ask her, and she shakes her head deeply.

“No. This essay I need to write must be my own work only. I'll get this down in no time, then I'll get my flank in bed. I sure am tired.” She says as, on cue, she lets out a deep yawn. You chuckle a little and smile.

“Well, if you're sure Cheerilee, I'll be heading home now. Please, let me know how it goes tomorrow, okay? I'll be waiting for you.” You say as you start trotting towards the door.

Right as you're about to open the door, you hear her.

“Candle Wick, wait!” She called after you, sprinting to the front of her home where you stood. She slows down as she reaches you, and looks down for a few moments.

You look at her, waiting for her to speak. When she never does, you decide to speak yourself. However, before you get the chance, she in one fluid motion swings her head up to yours and smashes her lips delicately on yours.

It was like a scene straight out of a movie. This caught you by complete surprise, shock plastered on your face. Was Cheerilee really kissing you? Yes, she was, and it felt nice.

While you initially resisted her, you slowly but surely feel yourself succumb to her. You let your eyelids flutter shut and start kissing her back, your muzzles opening and closing as you both passionately kiss. She tasted heavily of daisies, you mentally note.

After what feels like a lifetime, she reluctantly pulls away, her cheeks tomato red from blushing.

“I'm...very sorry, Candle Wick. I don't know what came over me! I just, I wanted to say thank you for helping me, and I couldn't think of another way, I am so, so sorry, please don't hate me-” You cut her off by putting your hoof to her lips, silencing her frantic speech. She whimpers softly as she looks at you. You smile at her.

“Why are you getting so worked up, Cheerilee? Yes, I was shocked at first. But if I'm being completely honest, that kiss was very nice.” You say in a gentle, soothing tone to her. She smiles back at you, tears in her eyes.

“Thank you, Candle Wick. You turned one of the worst days of my life into one of the best. I know you need sleep, so... go home. I'll see you soon, ok? I promise.” She tells you, and you nod, turning around and walking out her front door, trotting down the dirt road to your home not too far from hers.

You get home, unlock your front door, close it, lock it, same routine as always. But this time, instead of your feeling tired and gloomy and fatigued like normal, you feel energetic, upbeat, and happy. You nearly skip up the stairs to your bedroom when you're done locking up, and nearly bounce into bed happily.

As you turn out the lights and lay in your bed, your mind is deep in thought, recounting the days events. You recall your trip to the market, then seeing Cheerilee in the school yard, retrieving the folders while in particular recalling the embarrassing slide incident. Then going to her home, and then the most prominent moment of all.

The kiss she gave you. Your mind swims around that thought like buzzards circling a carcass. As if a phantom sensation, you can swear that you can still feel her lips moving against your own. You swear you can still taste her; daisies. You swear you can still hear her gentle moans.

As you start to think deeper and deeper, a thought occurs to you. Could Cheerilee possibly like you? That thought throws you for a loop. First of all, Cheerilee is quite a few years older than you, about seven. But then you remember your own parents were about that far apart, and they were as madly in love as two ponies could be. If it wasn't an obstacle to them, why should it be to you and anypony you love in life? Age is merely a number.

As a final thought before you fall asleep, you tell yourself that if this kiss leads to something more between you and Cheerilee, you'll be happy no matter what happens.

As you fall asleep, you have the biggest smile of your life plastered on your lips, and you can still taste daisies.