• Published 20th Oct 2013
  • 2,584 Views, 90 Comments

Letters for Cheerilee - MephileztheHam



A lonely Cheerilee has nothing going for her in life as she spends her days grading papers and dealing with rowdy students. But one day she gets a letter from a secret admirer and her life starts to change, but is it for better or for worse?

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Chapter 1: Start of an Interesting Weekend

“Come on, just ten more minutes till class is over! Come on clock, move faster! Come on, come on, come on!” I screamed mentally at the ticking clock on the wall in hopes it would actually adhere to my thoughts. I tapped a hoof against my oak wood desk absentmindedly in time with the clock's ticking, tap bucking tap. Save for tapping, the scribbling of pencil on paper and lets not forget the incessant ticking of the clock the classroom was otherwise silent. Just the scribbling of my students and the ticking clock tickled my eardrums.

Just ten more minutes until I can go to my lonely empty house and spend my lonely weekend alone, fun fun! At least its calm, no questions being asked and everypony focused on their work. But of course the quiet was not going to last, not on my luck.

“Miss Cheerilee! I have a question!” Yelled a voice from the back of the class. Celestia bucking damnit, why!? It's probably Snips or Snails, almost everyday they have some sort of dumb question to ask me. If that's the case should I just pretend I didn't hear them and fake a nap?

“It is your duty as a teacher to adhere to a healthy mind and its questions Cheerilee!” And there goes my conscience. For once can my conscience shut its trap, just for a friday? “If I wasn't around you would be home binge eating on that ice cream again, you know what happened last time!”

Ugh, he had a point about that one. And I was planning on calling in sick and diving into that rocky road tub of deliciousness but I couldn't afford going over my calorie limit again. Nearly gained ten pounds this month! And another thing, why is my conscience a guy? You know what, I don't have time to deal with mental conundrums. So with a groan and a final rough tap on my desk I listened to the voice in my head and scanned the rows of desks for the student who dared drag this class out longer for me. I spotted a single orange hoof in the air above the sea of tired looking children and instantly felt my irritation die out.

Without a word I pulled my tired self away from my sanctuary of a desk and approached the hoof. Passing by my students I noticed everypony understood today's arithmetic judging from the look of the completed worksheets on their desks. That or they just filled in random answers in hopes I would just glance over and grade on completion. I really hope it was the first one. Finally I made it all the way across the sea of students and arrived to the owner of her still raised hoof, Scootaloo.

“Yes? What is your question dear?” I said in a sweet tone to my favorite student in the class. I watched Scootaloo lower her hoof to point at her worksheet, her worksheet that only had the first three questions answered might I add. I sighed, it was going to be a long ten minutes until the bell rings.

“Scootaloo, didn't pay attention today again huh?” I groaned, pinching the bridge of my nose as I did. Scootaloo just smiled guiltily and shoved the worksheet toward me.

“Its just soooo boring! I could have done it if Apple Bloom and Sweetie Bell were here....they always help me with math stuff....” Scootaloo gave me the biggest puppy dog eyes she could muster and blinked them at me along with a pouty frown. I just rolled my eyes, so this is how she is going to play this one?

“Okay, okay I get the message Scoots. I'll extend the due date and I will even get the class to group up together to share answers, but this is the last time okay? You need to pay more attention in class” with that said I made my way back to my desk and cleared my throat. Everypony in the room perked up, all eyes on me and all little ears aimed in my direction. No pressure or anything, this won't backfire at all.

“Now I have an announcement to make before class ends so lets get this out quickly before the bell rings okay everypony? Now this piece of news is not going to make you all happy but I want to organize another group project that will be due next Monday” almost immediately as I said the word 'project' all of my students groaned and whined loudly. Yeah, yeah let it all out you big cry babies. “And the theme for this weekend project will be on the worksheet you were all working on today. So get into groups of three to four to review and create three questions based on the worksheet for us all to go over on Monday!”

Another set of groans erupted from the class and I groaned along with them. They really weren't making this one easy, thankfully nopony had any objections. All I got were angry glares and mumbled curse words. Oh I am so going to call up a parent teacher conference on to talk to their parents about their children's language. I swear it gets worse every year!

“Now go on and get into your groups before the bell rings! Three minutes to choose, so go on!” I said sternly to my young pupils and watched with sadistic glee as they all scattered about the classroom. Well all except for Scootaloo who just sat in her desk and gazed pitifully at everypony grouping with their friends. This was a really bad day for both Sweetie Bell AND Apple Bloom to be away on some family get together leaving Scootaloo with nopony to group up with. Taking one last look at Scootaloo I went about packing my things. I am sure she will find somepony to work with on the project, right? Anyways, now where did I leave my-RING RING RING!

Well I guess its time to leave, jeez why does the bell have to be so bucking loud? Its a surprise how I am not deaf yet. Anyways now where did I put tha-

”And you better get better or your gonna end up dead in the water and fail you chicken!”

Ah Diamond Tiara, I'd know that voice anywhere. The token spoiled little rich kid of ponyville with a heart of coal. Never before in my years of teaching have I ever encountered such a evil little child. And now I have to deal with her, worst Friday ever.

“So you just shut up, you stupid blank flank! Who cares if you fail huh? If school really matters to you you better buck up and get some talent in math! But again who cares right? Just one less blank flank to deal with next year, aren't I right SP?” I cringed as the little brat taunted in that annoying voice of hers. If you asked me what she sounded like I can tell you after a long experience with teaching her I can tell you its like listening to nails on chalkboard. You know at first I was surprised when I found out about her mean streak, but now it was just a annoyance. A very stuck up, tiara wearing bully of an annoyance.

“Mhmm! The less blank flanks the better! Dumb blank flanks and their blank flanks!” and there is the ever enlightening words of Diamond Tiara's dimwitted companion Silver Spoon. Just another child who stays on the bully's good side so they don't get messed with. I watched with a cringe as the two little trouble makers bumped their flanks together and giggled evilly. Guess its time to save Scootaloo from their teasing. Time to demoralize the class bullies!

“Diamond Tiara! Silver Spoon! I am disappointed in you two! Picking on Scootaloo for having trouble in her studies!” I yelled as I did my best commanding adult voice to berate the two miscreants. I nearly giggled in smug glee at the flash of fear in both of their faces. But true to the duos manipulative ways, that look of fear was replaced by a fake mask of innocence. Oh here we go.

“But Miss Cheerilee I was just telling her she had to get better! She just took it the wrong way and started calling us names! She started it because she's just jealous of my good grades!” I facehooved, was that really she could do to persuade me? That wimpy little lie? Not this time you little brat!

“Honestly Diamond Tiara I expected better of you, apologize right this instant!” my voice boomed in a commanding tone as I towered over the bullies. But oh I wasn't going to stop there, now its time for the kicker! “And on top of that I am assigning Scootaloo to a study group, yours specifically, Diamond Tiara!”

“What?!” screamed both Scootaloo and Diamond Tiara, Silver Spoon on the other hoof was just staring at me wide eyed in shock. Oh my Celestia I wish I had my camera right now.

“You heard me little missy! Since you are so concerned about Scootaloo's well being both you and Silver Spoon will help her get better!” I rolled my eyes as I spoke, the very idea of Diamond Tiara giving a rats ass about somepony besides herself? Hah! But hopefully this will help Scootaloo in the end, hopefully. Diamond Tiara's reaction was just a strained smile and a raging fire of hate boiling in her eyes. I'll give her props for keeping a stoic face, it must be hell on her psyche to keep in that anger.

“Fine! Silver Spoon and I will do our best to help you....and I am....sorry” oh my she was trying so hard to be nice, I commend the brat for not exploding in pure rage by now. But oh my Celestia I could barely contain the ever looming giggle fit, would it be wrong for me to laugh at a child's expense? Maybe, but laughing at Diamond Tiara and potentially pissing off her parents isn't worth my job. Oh well, but by the look of Scootaloo's ever growing smirk I can see she was enjoying this as much as I was.

“Pffthaha! Oh my freakin, hahaha! Yeah sure, looking forward to working with you DT” Scootaloo giggled which only made Diamond Tiara and Silver Spoon harumph and leave the classroom stomping all the way out. As the stomping of little hooves dissipated I leaned down to my still giggling student and said “Well that was fun wasn't it? Never gets old to put them in their place huh?”

“Oh definitely, those hoity toity idiots got theirs!” Scootaloo cheered as she hugged me tight, maybe a bit too tightly. She went so far as to nuzzle into my chest, come one I don't need a affliction of diabetes this weekend!

“Thanks for watching out for me again, Cheerilee” she said as she looked up at me with those big purple eyes of hers. Hnng-buck, my heart!

“Anything for one of my favorite students! And I'll walk you home since your friends aren't here too!” I said as I hugged my favorite little pegasus. Scootaloo instantly brightened up and nodded furiously with a bright smile on her face. I knew that would get her excited, and walking home without your friends would be pretty boring. And dangerous depending where you live in Ponyville, this place isn't all sunshine and butterflies you know!

“Yes, yes, yes! That would be awesome! Er, I mean that would be cool” I watched with amusement as Scootaloo caught herself in her giddyness, trying to be all cool and collected. And I emphasize the word “try” by the way. Probably just her trying her hardest to emulate a certain rainbow maned hero of hers.

“Okay Scootaloo, but let me gather up my things for a second okay? Again Scootaloo nodded, albeit a lot less furiously this time. Turning back to my desk I put on my satchel and packed up all of my belongings.

“Favorite pen? Check, papers to grade? A sigh and a check, crossword puzzles for later? Check, and the most important of all? Lusty Equestrian Maid, checkaroo” I listed my things one by one silently to myself. Tossing the items into my satchel, but giving my very special book a little more care of course.

Hey, what book is that?” I nearly screamed at the little voice in my ears that I fumbled the book and ended up dropping the thing. Thankfully it landed on my desk face down obscuring the unmentionable front cover. Letting out a shaky breath I turned to see a hovering Scootaloo, her little wings buzzing as hard as they could to keep her afloat. I forgot she learned how to hover a while ago, Celestia she nearly scared me out of my skin!

“J-Just a boring book for adults Scootaloo, and what did I say about little pegasi flying indoors?” Scootaloo hung her head and landed back on solid ground, muttering her apology with a sad look on her face.

“No flying inside the classroom or halls, sorry Cheerilee”Sweet Celestia she has to stop with the pouty lips, she's killing me with cuteness! But I did feel a twinge of guilt for berating her but I had to enforce the rules, that and I want to change the subject off of my special literature. Imagine if Scootaloo saw the front cover? She would be scarred for life, maybe I should keep my private reading at home from now on.

“Just remember the rules Scootaloo. Anyways, shall we?” with that said we left school and made our way to the glory that was Ponyville . Little was said between us as we walked along the crowded streets of Ponyville, at least the weather was nice out. Everypony looked chipper today, the occasional passerby giving me a nod or a wave and a few winks here and there. Unfortunately those flirting winks came from some pony's I wouldn't be caught dead with. You get drunk one time in some sleazy bar and end up kissing some random stallion then poof! Everypony starts a rumor about how I am a loose mare and all that jazz, none of its true though. Although it would be the last time I went out with Lyra and Bonbon on a girls night out, I can't really handle liquor, period.

“Hey Cheerilee! How many bits do you have on you? I wanna get a snack from that stand over there!” Scootaloo's words tore me from my reminiscing and brought me back to the present. Absentmindedly I looked through my satchel and pulled out a hefty bag of bits. But I had a feeling it wouldn't be so hefty in a few moments.

“Mhmm, how many bits do you need?” I asked the orange filly as I rummaged through the bag.

“How much do you got?” Scootaloo simply said as she gazed intently at my bulging bag of bits.

“How very blunt of you, Scootaloo. Here's thirty bits you little scamp” I teased, dropping the sum of bits into her waiting hooves. The little filly jumped for joy and dashed to one of the nearby stalls. And surprise surprise the pony running the stand was Bonbon, haven't seen her in a week. Time for small talk until Scootaloo finishes spending my hard earned bits I suppose.

“Hey Bonbon! Long time no see girl!” I called out to the cream mare as I trotted along side Scootaloo to her little stall. 'Bonbon's fine gourmet candies' was emblazoned on a cute yet professional looking sign just below the candies themselves. The mare behind said sign gave me a happy smile and a little wave.

“Why hello there Cheerilee, you disappeared on us for a while there! Busy with grading school work and all that?” I nodded at her question, hit the nail on the head right there.

“Story of my life Bonbon, I couldn't even find some time for myself last week! Last time I procrastinate on grading work, let me tell you that sifting through a mountain of paper work is not a good way to spend four hours a day!” I cringed at the memory of all those papers laying on my coffee table, what a bucking nightmare.

“I'll bet, Lyra and I have had our fair share of work but its not so bad with the two of us working together. I gotta say Lyra has been a lot more helpful ever since we started dating, believe it or not she is actually not being lazy for once!” Bonbon said with a dreamy look in her eyes. No doubt thinking about the mint green mare. She told me all about how they finally started dating, something about a confession in the local spa. About time I say, those two are made for each other in my opinion.

“You know Cheerilee, thinking about Lyra and I, I think its time you find some-”

“Ahem! Can I buy some chocolate please?” Scootaloo interrupted as she jumped up and down eying the little candies like a predator at her prey.

“Oh sure, take anything you like and let me know when your ready! Now what was I going to say? Oh yeah, have you found a coltfriend yet?” Suddenly I felt cold inside, Bonbon's question hit me like a sack of bricks.

“No, no I haven't. I just haven't found the time to go out and find that special somepony you know? And I don't know if I can handle a relationship right now, not after....you know....” I couldn't finish my sentence, just thinking about that stallion left a heavy feeling in my gut.

“Yeah, whatever happened to him? He skip town or something after....you know?” I nodded and kept my eyes downcast away from Bonbon's. As a matter of fact he did leave after our little incident, bastard just left me alone with a bad taste in my mouth. I really don't want to talk about him, besides its been a few months since then so it shouldn't matter anymore. And yet I still feel terrible about it.

“Look Cheerilee, I know you don't want to try a relationship again but you can't stay cooped up in your house alone all your life! At the very least just try to talk to somepony, isn't there a stallion you like at your work or something?” not this again, I don't need somepony telling me how I should live my life. Telling me I should just shrug off my hurt emotions and find some random white knight to fall in love with. As if it was that easy!

“Excuse me! I want all of these please!” Scootaloo piped in, motioning to a sack of assorted treats in her hooves. Note to self, do not bring Scootaloo along to important conversations. Bonbon just sighed at Scootaloo's repeated interruptions and wordlessly took the filly's bits and turned back to me.

“I'm sorry that he hurt you and all but you have to stop living in the past! How about Lyra and I take you out to that bar again? Minus the alcohol?” Bonbon offered with a small smile that said, trust me. Going partying with Lyra and Bonbon to the same bar? That's a recipe for bucking disaster.

“I think I will pass, I'm not much for partying anyways. But thanks for giving me the offer Bonbon, but you do have a point on me being lonely and all that. I just need some time to think” I said with a forced smile. Bonbon returned the smile and suddenly disappeared under the stall and came back up with a basket of chocolate. I gave her a confused look and she merely smiled and tossed me the basket.

“Here, something to brighten up your night later! But don't eat it all in one sitting cause I know how you are with sweets, and don't disappear for a week again okay? We are your friends and we are here for you, just give us a call and we'll hang out kay?” Bonbon said reassuringly with a wink. I said nothing but I gave her a genuine smile this time and left with Scootaloo in tow, whom was munching on her bag of goodies. Again we found ourselves enjoying a quiet walk that had the less than pleasing ambiance of Scootaloo's chomping.

“Hey Cheerilee? Who was the guy you and Bonbon were talking about?” I froze, nearly stumbling over my own hooves at her question.

“O-Oh just a old acquaintance that I used to be friends with” I stuttered, damn I stuttered. There is no way she is going to let this drop after that one.

“He didn't sound like just an acquaintance, he used to be your special somepony huh?” Scootaloo whispered curiously. I don't know why she was whispering, probably to seem mysterious or something. But there was no hiding it now, might as well tell her bluntly.

“Yes he used to be, but something bad happened and now we aren't together” I muttered. Maybe now Scootaloo will let this drop.

“What did he do?” bucking damnit. This isn't something I thought I would be talking to a child about. Why won't she just drop it?

“Look Scootaloo it is in the past now alright? It's nothing to worry about now, just some old story that should be left in the past okay!” I couldn't help but raise my voice at the orange filly. But just thinking about that stallion just bothered me to no end.

“Sorry Cheerilee....he must have been a huge ass huh?” I giggled at her hushed saying of her little curse.

“Yes, yes he was” and with that said we went along our little stroll in comfortable silence. Finally after our little trek through Ponyville we arrived to the building we were looking for. A rather large orphanage with a just as large sign out front that read “Young Hearts Orphanage” it may not be a building you'd associate with happiness but at least it looks nice and well kept.

“Aww we are already here? That went by fast!” Scootaloo pouted as she glared at her home. I couldn't blame her for not wanting to come back here of all places but what can she do? She hasn't been adopted by anypony yet and she doesn't have any other place to stay.

“Don't worry Scoots, we can have more of these walks later if you want?” Scootaloo pondered my offer with a hoof on her chin but ultimately shook her head.

“Nah, it wouldn't be fair for me to keep calling on you to keep me company and stuff. Besides, it isn't that boring here, I have other small friends inside and stuff!” Scootaloo said in a happy tone but I knew she was lying. The smile is there and all but the sad worried look in her eyes is a dead giveaway. Such a young filly trying her best to seem all tough and resilient, oh Scootaloo.

“Okay, but if you ever change your mind you know where I live so don't be shy if you need somepony to hang with. And it would be a great way for me to help you with your studies!” I mused happily at the very thought. Visiting Scootaloo to keep her company until her friends come back and I can cure my loneliness with some tutoring. But Scootaloo looked less than pleased at my idea, if the rolling of her purple eyes were any indication.

“Yeah, that sounds really cool and all that but I think I'll pass on that tuitoring. But hanging out sounds cool though, bye Cheerilee!” Scootaloo said as she trotted up to the orphanage and disappeared inside. With a sigh I gave the orphanage one last look and made my way to my own home. On the way home I found my mind swarming with so many thoughts I thought I would get a migraine. Thoughts about Scootaloo, Bonbon's words and most of all how I was going to break this streak of loneliness in my life.

“Why not just go along with Bonbon's advice and go talk to some stallions at the local bar? You might not find Mr. Right but you will at least spend an evening talking to somepony instead of downing ice cream and reading dirty romance novels!” And there is my good old conscience speaking out of turn again. Eh, he does have a point though. Maybe I should get off my ass and spend some time getting to know somepony and see where that goes? Meh, ice cream sounds better to be honest.

“Why do I even bother with you?” my conscience whined as his voice dissipated back to nothingness. I don't know about you but I am glad that voice is gone for the moment, I should probably see a shrink about this voice in my head. After a few moments of thinking about my sanity I found myself in front of my home, well that was a quick trot. Looking up at the lonely magenta hued home I let out a wistful sigh. It was two stories, had a roof like all of the other buildings in Ponyville. But one thing that made it my own was the small little garden out front filled with all sorts of flowers and plants.

All of this to myself, a big two storied home with nopony to share it with. Jeez I am such a bucking downer, I have to see new people or risk going insane at this rate. Shaking those loathsome thoughts from my mind I entered my home and locked the door behind me. Flicking on the lights I found that everything was just how I left it. Two burgundy couches with a coffee table set in between them, a pile of books rested on said table. Besides the living room sat the kitchen and a hallway leading to the bathroom and a door leading to the basement. All in all the first floor was nothing to write home about.

“Time to unpack and get ready for some time alone with myself, again” with a sigh I unpacked my satchel and poured the contents on the coffee table. Placing the satchel and my basket of chocolates alongside my things I made my way upstairs and to my favorite part of my home in my opinion. Not that anypony has seen the inside of my home to give opinions on it but whatever. There in all of its dusty glory stood my own personal library, several bookcases containing a hundred or so of my favorite books I collected over the years. To the first book I fell in love with as a child to the most recent romance novel I bought from my visit to Canterlot last year. Its a shame that I haven't had time to add to my library, I blame the droves of school work this year.

Maybe I'll go shopping this weekend for books and then head to a bar afterward? Yeah that sounds like a plan, but first, shower time. So with my new goal in mind I left my library behind and went into my bedroom, the plainest part of my house. My bedroom wasn't really that special, just a queen sized bed, a little night stand with a just as tiny lamp and a dresser with pictures of my family back in Canterlot. Letting loose another sigh I sulked over to the door on the other side of my room that led to my personal little bathroom. Well its not like anypony else lives here to warrant calling this one a personal bathroom but....okay I'll stop now, I'm bucking lonely!

So after a quick shower I went back downstairs and plopped myself on a couch. Looking over to the pile of books on the coffee table I scoured for a certain piece of literature.

“Now where are you? Ah! There you are!” I said gleefully as I picked up one of my favorites and the very same book that almost scarred Scootaloo for life. “Lusty Equestrian Maid” was written in big cursive letters over the image of a pin up of a red mare in a sultry maid outfit being held in the hooves of a handsome stallion. Both of them locked in a heated kiss of passion. And a well drawn pin up might I add! This thing is known a cult classic based on just the front cover alone but the story of a maid and her unrequited love with her dominating master really hooks you in.

What? Don't judge me, its a good read, honest!

“Yeah keep telling yourself that, you're just indulging in your weird fantasies with books like these. Why don't you try reading a non trashy romance novel for once? Like a story where a downtrodden poor mare gets taken in by a rich stallion or something?” complained my ever so annoying conscience. But before I could offer a witty retort the sound of somepony knocking interrupted my inevitable argument with my psyche. With a annoyed sigh I got up and went over to answer, not even stopping to check myself to see if I looked presentable. Between these interruptions all day and battling my loneliness plus my conscience, I just don't care anymore today.

With a clunk of the lock I swung open the door and there standing in her little mailmare outfit stood Ditzy wall eyes and all.

“Heya Chers! Got mail for ya today!” blurted the mailmare as she thrust a single envelope in my face. Taking the envelope in hoof I gave her a nod and bid her good day. With a awkward salute Ditzy took to the sky and flew in a zigzagging pattern to her next delivery. What a crazy mare, taking her job in stride with such childlike glee. I wish I had that same enthusiasm right now, it would help with grading homework. Shutting the front door behind me I sat back onto the couch and ripped open the envelope.

“Huh, now that is nice stationary. Did the bill company's suddenly become more professional when I wasn't looking?” I said sarcastically as I unfolded the rather extravagant piece of paper, it had purple trimmings on the sides too. Looks like somepony sent this letter with the goal to impress.

“Now lets see here....Dear Cheerilee....what the buck?”

Author's Note:

Oh boy, what could be written in that letter? The suspense! But hey, new story and a new chapter! But now I am going to be honest here, for all of you following me I told you guys I was working on something new. And this is that new thing, but it was supposed to be uploaded four days ago. My excuse? Purchasing a new 3ds along with Pokemon Y, I regret nothing! Anyways I hope you guys enjoy this chapter and let, and to all you reading? Stay beautiful!