• 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 4: Project Troubles and Board Games

I could not believe how bad my luck is right now. It seems like everywhere I go some sort of interruption just comes barging into my life from out of nowhere. And today it came in the form of a little orange pegasus on my doorstep named Scootaloo. Whom was now sitting on my couch doing her best puppy dog eyes and pouty lips routine. With a roll of my eyes I turned my attention to my now sizzling eggs and began to scramble them with expert precision.

“Okay Scoots, enough with the puppy dog eyes alright? Lets just take it over from the beginning, what happened between you and Diamond Tiara exactly?” I questioned Scootaloo as I continued to mix the yellow concoction on the frying pan. Taking a quick glance away from my eggs I watched curiously as Scootaloo wrung her hooves over each other nervously, her purple eyes darting left and right. Ah the tell tale signs of a child fabricating a story when put on the spot. Whether or not the story will be true or just a long winded fib has yet to be seen.

“Well you see, it all happened yesterday. Diamond Tiara, Silver Spoon and I were working together on the project you gave us as usual. It was going surprising well, as well as working with that spoiled brat was anyways. But yeah, it didn't stay that way for long....” Scootaloo went went silent for a moment, she took a long inhale of air and held it for a few seconds before releasing it. It was like she was trying to brace herself, maybe to control her emotions?

“We got into a argument over the graphing portfolio thingy, Diamond Tiara didn't like how it came out. She was all, this isn't how it's supposed to look you useless numbskulls! Anyways we started yelling at each other after that, over who's fault it was and all just the usual crud that Diamond Tiara bullies everypony over ya know? Until....” Scootaloo stopped mid-sentence as she tapped her hooves together before slamming them into the couch. This can't be good, so I stopped cooking and left everything on the back burner.

There is plenty of time for cooking breakfast later. Scootaloo's problems come first.

“Scootaloo, what hap-”

“She made fun of my parents. How I was an orphan, how I was useless. That I was just a pathetic little no talent pegasus that not even my mother and father wanted. Who would want a waste of space like you anyways? You're just a useless idiot that bucks everything up, that's what she said.”

God bucking damnit, sounds like something Diamond Tiara would do. I know she is a rotten little fill, hell everypony knew about it. But this was the lowest of any blow she had ever done, attacking Scootaloo orphaning? What a little monster that tiara wearing little filly was.

“The next thing I knew that dirty little....bitch was on the ground with a bloody nose” Scootaloo cursed, her lips curling into a snarl. Even though she was upset she struggled to try not to curse. Any other day I would have reprimanded her, but right now she has every right to curse until high noon.

“Everything went by so fast, I didn't even know I punched her until she was screaming. Next thing I knew, her dad barged in and she played the innocent little filly like she always does. Filthy Rich threatened to have me expelled for hitting his little girl, so I ran home as fast as I could” as Scootaloo told her tale I went over to her side and sat next to her. So many thoughts buzzed in my head, and all were aimed at punishing a certain tiara wearing filly. However that wasn't what was bothering me right now, it was Scootaloo.

I expected for there to be tears, crying, anything you would expect a child to do in a situation like this. Yet she was the exact opposite of that, she was calm and collected. Her voice showed no sign of wavering, not even a hint of a sob. She was holding everything in, she was doing her best to be strong and hold everything in. But even though she wore a mask of indifference her eyes told another story. The pain was there, and so were the tears brimming in her eyes threatening to spill over.

“I really am useless huh? I can't even do something as easy as ignoring her right. Maybe if Sweetie Bell and Apple Bloom were with me they would have held me back before I did something stupid. But by myself what am I? Just another orphan that doesn't belong, right?”

My heart sank at Scootaloo's words, how could she even think of herself like that? It hurt me to hear her say these things, and that look in her eyes? She was begging for me to say something, and damnit did I have something to say!

“No, you're not just another orphan that doesn't belong. You are a amazing little filly who tries harder than anypony else. I have never seen a student as persistent as you, you are not useless. You are amazing, and damn anypony who says otherwise!” I said as I swept up Scootaloo in my arms. Hugging the little pegasus with all of my heart.

Scootaloo said nothing, which scared me for a moment. That was until she snaked her hooves around me and returned the hug as tightly as she could. And right then and there, she broke down into tears.

“It's alright Scootaloo, it's okay” I cooed, rubbing a motherly hoof through her mane. And so I sat there with Scootaloo in my hooves as she cried her little heart out. It doesn't matter if Scootaloo is a orphan, she is so much more than that. She may not have parents, I may never the best substitute for them. But as long as she needs me to be, I will be here to wipe the tears away.

I didn't know how long it took for her to calm down but eventually the tears had stopped and a comfortable silence befell us. I idly stroking her mane with great care and Scootaloo nuzzling into my chest. Every so often she would squeeze me tightly for just a second. I notched it off as her checking to see if I was still there, maybe.

“Thank you, for putting up with me” Scootaloo's words tore me from my thoughts and back to reality. I looked down to see the little filly regarding me with her purple orbs, her eyes gazing expectantly at me.

“Remember what I told you Friday?” I asked softy.

“That you would always be there for me?” she said with a small smile. That's better, turned that frown right upside down. But I half expected her to have forgotten, to be honest.

“Exactly, I will be there for you no matter what. I may not be your mom, heck I am not even qualified for anything like that! But if you need a friend, I'll be right here” as I said my heartfelt words Scootaloo's grin grew and grew until it turned into a toothy smile.

“That was really sappy, Cheerilee. You couldn't have said that in a cooler way?” Scootaloo laughed. And just like that the moment was gone. Can't say I am surprised.

“Gee, thanks Scootaloo” I muttered flatly. Scootaloo only laughed even harder at my reactions, even going so far as to tumbling out of my grasp onto the floor. Where she continued to literally roll over the floor laughing, sigh. Yep, the mood is definitely bucked.

“No, no I appreciate it! I'm just kidding, you said it in the good kind of sappy way ya know? But um yeah so....ahem, thank you Cheerilee” well at least she said thank you. Alas our little moment of bonding didn't last long, a knock on the door threw that idea out the window.

“I think that's our cue for the sappyness to end huh? Let's go see who it is, come on” I said with a sigh as Scootaloo and I made our way to the front door. With a clink and a clank the door swung open to reveal a familiar purple sight.

“Good morning Twilight, what brings you to my humble abode?” I asked sincerely.

“Yeah morning, hey is Scootaloo with you? Rainbow told me to look out for her. Apparently she saw her earlier running through town like a bat out of tartarus. She said she looked distressed so I have been looking around for her everywhere. If you know anything about her location please tell me” well then, looks like I a wasn't the only one worrying about Scootaloo.

“Well you're lucky you came here first cause she's right-”

“Here!” Scootaloo squeaked from under me. Looking down I saw the orange pegasus peaking out from underneath me with a stupid grin, what a silly filly.

“Oh my gosh, you're alright! Rainbow and I have been so worried!” Twilight exclaimed.

“Rainbow Dash was worried about me?” Scootaloo asked with a air of disbelief.

“Of course she was, we all were! And when I heard that Diamond Tiara was involved, oh I thought something terrible must have happened. Like a prank gone wrong or something!” Twilight's words only seemed to confuse Scootaloo even more. Either she was stunned that ponies actually cared about her or the fact that her idol was worried about her, I couldn't tell. Yet before I could investigate either of those possibilities the sound of wings flapping sounded out nearby.

“Hey Twi! Did ya find the little squirt yet?” a raspy voice called out from above. Not a moment later the voice was followed by a very anxious looking Rainbow Dash nearly crash landing into Twilight.

“Yes I have, and she is safe and sound!” in that instant Rainbow pushed past Twilight, her eyes darting in every direction scouring for a certain orange filly.

“Where?!” Rainbow's voice sounded distressed, almost desperate even.

“Uh, down here? Come on, I'm not even that short!” Scootaloo piped in, annoyance clear in her voice.

“Scoots!” In that instant Rainbow swept up the filly in her arms and hugged her like there was no tomorrow. A second later she noticed Twilight and I staring, big tough Rainbow Dash caught in the act being a big ol softy. And like a filly caught stealing a cookie she dropped Scootaloo, a shy smile on her face accented with something I thought I would never see on Rainbow's face. A raring blush, where is my damn camera? “Eheh, good to see you're okay there Scootaloo.”

“Yeah, yeah I'm fine! I was just hanging out with Cheerilee after a....prank gone wrong. Yeah a prank got messed up and I was scared is all! So I hung out with Cheerilee for a bi-”

“Scootaloo, it's okay. Just tell them what happened, we are all friends here” I placed a stern hoof on her shoulder, to both reassure and stop the train wreck of a fib she was trying to pull off. Scootaloo took a deep breath and let out a shaky exhale. Here we go....

Several Minutes Later....

“SHE WHAT?!” Rainbow screamed at the top of her lungs. Yeah I imagined a reaction similar to this one, although it was a lot quieter in my head. My ear drums are pounding!

“Rainbow calm down!” I watched as Twilight tried to calm the angry pegasus but her actions only worked to agitate the mare even more.

“Calm down? Twi, that little tiara wearing brat went over the edge this time! It's high time somepony spanks that good for nothing little....” already having a good idea where this rant was going I quickly covered Scootaloo's ears. Thankfully I was quick enough because not a moment later the rainbow maned pegasus unleashed every curse word in her vocabulary. And let me tell you she had quite the repertoire of cuss words, I bet she was a sailor in her past life.

“....bucking piece of....okay, I'm done now” Rainbow said as she gasped for air after her long winded cuss fest. Cautiously I lowered my hooves from Scootaloo's ears, just in case Rainbow would start up again. Thankfully she didn't.

“Okay, now that Rainbow is done with that....display let's go back to the problem at hand shall we? First things first I agree with Rainbow, we can't let Diamond Tiara get away with this. Cheerilee, why don't you order a parent teacher conference tomorrow with Diamond Tiara's parents? It would give you the opportunity to confront them about the problem easily. I am sure after you tell Scootaloo's story they will discipline Diamond Tiara accordingly. Any thoughts or objections, girls?” Scootaloo and I both shook our heads, it was a sound plan in my opinion. I was actually planning on calling that filly's parents over for a little conference tomorrow anyways.

And if Diamond Tiara's parents don't discipline her, which they won't, then I will take matters into my own hooves. A few letter grade drops would snap Diamond Tiara in her place in a instant. If there is one thing I can attest to is to never piss of your teachers or your grades go to shit. And flunking class would definitely get her out of her parent's good graces for a month or two.

“Meh, I still say we bend her over a table and take a leather belt to her behind” Rainbow scoffed, crossing her hooves over her chest.

“I think we can all agree that she deserves a good spanking, but this requires a soft touch. Tomorrow I will have a nice long chat with Diamond Tiara's parents and hopefully everything will go right as rain.” I said, the image of Diamond Tiara bent over my knee getting taught a lesson was unfortunately a moment that would have to be avoided. And who knows, maybe her parents will finally grow some balls and spank their rotten brat for once, here's hoping!

“Okay then it's settled! Come on Scootaloo, we should get you back home before they get worried. We can go for ice cream along the way, my treat!” Rainbow said with a beckoning hoof. However, Scootaloo declined with a shake of her head.

“Nah, I wanna hang out with Cheerilee today!” yeah you should go, wait what?

“Yeah lets, wait what?” my sentiments exactly Rainbow. What indeed. Scootaloo denying a day on the town with her idol? Again....what?

“I gotta do some homework and Cheerilee promised to help me with it! It's part of the reason I came over anyways, sorry RD....” Scootaloo lied, and to her idol! All of my what?

“Ok....well if you say so then. I guess I'll be off, see ya later guys!” Rainbow said her goodbyes and took off, her signature rainbow trail flowing elegantly behind her as she went.

“Well I guess I should be leaving as well, unless you want some help with that school work, Cheerilee?” Twilight asked almost a bit too enthusiastically. I just shrugged it off as Twilight being her usual studious self. Always jumping at a chance to do research or do studious....things. I don't know what she does in her free time, get off my back!

“I didn't say anything, sugar” oh he didn't? I guess I was expecting some gay commentary or something....moving on!

“Actually Scootaloo doesn't have any homework, she-”

“Lied! I am actually just going to chill here with my favorite teacher, just cuz!”

“Thank you for interrupting me and who said you were going to stay over?” I said, giving the orange pegasus my best “I am not amused” face.

“Aw come on, we can play games and stuff!” Scootaloo begged as she latched onto my neck, her little body shaking back and forth as she swung. I was about to say no but Twilight stepped into the ring, so to speak.

“I think that sounds like a great idea, doesn't it Cheerilee?” great, two on one. This seems hardly fair. Might as well quit before I am ahead I suppose, just this once.

“You know what? Fine! I have some board games in a closet somewhere that I used to bring out during old parties of mine. We can use tho-” before I could finish my sentence Scootaloo promptly dropped from my neck and galloped back inside my home. I looked to Twilight and sighed.

“Kids huh?” I grumbled as I followed after the orange little blur with Twilight close behind.

“Kids, what a joy eh?” Twilight smiled. Well at least one of us is getting a kick out of this.

“Hey Cheerilee! Which closet has the games in it? There's like four closets!” Scootaloo yelled out from somewhere in the house.

“They're in the kitchen closet! Lower shelf!” I yelled back. A moment later a tumblr was heard and the orange blur that was Scootaloo galloped into the kitchen ahead.

“Why are they in the kitchen closet?!” Scootaloo asked as she swung open the closet and dove inside. I said nothing, merely resorting to just sighing loudly and plopping myself on a nearby couch cushion.

“Why ARE they in the kitchen closet?” Twilight repeated as she took a seat next to me. Please can everypony stop with the questions? I am getting a bucking headache!

“I am curious as well, why the hell do you keep board games of all things in a kitchen closet meant for post and pans and shit?” not now mister!

“Keeps them close to the living room in case I have company over” I stated simply as I rubbed my temples to sooth my oncoming headache. Thankfully Twilight didn't have a comment. But suddenly her horn lit up in a purple hue. It grew brighter and brighter until it flashed brightly for a brief second. In the instant the flash of magic had come no sooner had my headache suddenly disappeared.

“There, that should help with your headache! It's a neural healing pulse that's good for up to two point five meters. I use it on myself sometimes while doing heavy studying, no need to thank me”

“Thanks Twilight, what would I do without you?” I said. Twilight said nothing but blushed, is it hot in here? Maybe I should turn the ac down?

“Okay, I found a game! Hope you nerds like monopoly!” Scootaloo called out from the kitchen. A moment later she came out from the kitchen with a white box on her back. And sure enough in a extravagant old timey picture was the title “monopoly” showing proudly for all to see. Scootaloo lay the box down and tore its cover off, dumping all of its contents onto the carpet floor.

“Lets see here, manual? Check....pieces? Check, fake money? Checky check, cards? Checka check, and most importantly....tadaah! The board!” Scootaloo exclaimed as she presented the monopoly board like a trophy.

“Okay you big screw ball, let's get this thing started shall we?” Twilight teased the little filly with a boop on the nose. And with that little boop the game had begun. Scootaloo chose a lightning bolt as her piece, I wonder why? A book was chosen for Twilight and myself I had chosen a poodle. Well beggars can't be choosers....it was either the poodle or the soup can. Who the hell designed these pieces?

Regardless of who made these idiotic chess pieces we began our little game of monopoly. After a few turns of buying and selling properties there was a knock on the door. Damnit, and right when I was about to get rent for my spot....

“I'll get it, you two keep on doing what you're doing” leaving the two busy bees behind I left to the front door and swung it open. There standing in all her wall eyed glory was Ditzy with a hoof outstretched towards me. In said hoof sat a purple letter, the very same kind of purple a certain admirer writes in.

“Letter” Ditzy simply said, her hoof shaking the letter in my face.

“Indeed” I responded with a curt nod.

“Yes” ah her eloquent way of speech was breathtaking.

“Quite” I offered her a well thought out retort as I accepted her letter, carefully taking it in my own hooves like it would tear at the slightest touch.

“Bye!” with a well said goodbye Ditzy was off like a rocket, spiraling up through the clouds in that signature erratic flight pattern of hers. After that odd exchange of words I shut the door and went back inside to my two companions. And by the looks of the game board it would be safe to say that they are nearly done, looks like we will have to start over soon. But first things first, my admirer's letter.

“Whats with the letter?” Scootaloo's question froze me, oh boy I've been put on the spot. And right when I was about to tear open this bad boy, buck.

“Oh nothing, just a letter from a pen pal of mine: I half lied half told the truth as I ripped open the envelope. They don't need to know about my romantic life, or lack thereof should I say.

Would you just read the damn thing? Stop monologuing internally, sugar” but I like monologuing internally....fine, time to read.

Dear Cheerilee, I am happy to see that you are still writing to me! And to answer your first question on why I chose to write letters instead of just talking to you, well I guess you could say I was nervous. I found the very idea of speaking to my crush was simply terrifying, yet I wanted to tell you how I felt somehow. After pacing in my home for what felt like hours I had a moment of clarity, letters. A simple yet effective way of communication to one another and a fantastic alternative to awkward face to face conversation. Let's just say that talking about these kinds of things in person would just leave me a stuttering wreck.

Well that explains that I suppose. It makes sense, I certainly be nervous as hell if I had to speak to my crush to their face. And Celestia knows that I would have done the same thing, probably.

Next I suppose I should state what kind of pony I am then? I would like to proudly state that I am a unicorn, magic and all.

Ah so he's a unicorn huh? Now that is interesting, I wonder what he looks like? Damn, I should have added that bit to my question earlier. Oh well, I hardly think that he would outright describe himself word for word anyways. A secret admirer is secret for a reason.

The answer to your last question took some time for me to write out, your question simply irked me. But not in a bad way mind you! It's just that I had to rewrite my answer several times, you have no idea how long I spent scribbling away at my desk! And I would like to say bravo for hitting me with the hard interrogation question for your last query. The previous sentence is laced heavily with playful sarcasm if you hadn't noticed, but I merely jest.

That last sentence put a smile on my face. I can picture my admirer now, a handsome young unicorn scribbling away on this letter for hours. His brow wet with sweat as he pondered over the perfect way to answer my question. He's probably muscular, I can imagine his muscles bulging here and there as he flexed in his chair, his body stressed from being forced to sit still for so long. The lovely sinew just begging to be massaged by a lover while he wrote. Hmm....

Focus girl, you're day dreaming again. And in the company of a filly and a princess! Have you no shame?” the drag queen in my head said in a annoyed tone. Damn, he's right. I was about go on one of my day dreaming binges, focus!

But enough of my jokes, onto the serious answer to a serious question yes? You asked what about you attracted me to, well you. Well, I know this will sound cheesy but simply everything about you had drawn me to you. Yet please understand that this was not love at first sight event however, that would be way to stereotypical to that of a cheap romance novel.

Hey! Those are the best kind of romance stories!

To describe my attraction to you, I would compare it to how a stubborn moth is drawn to a freshly lit flame. The moth sees the light but sees nothing more than a flame, something to be ignored at first due its stubborn nature. But soon enough the moth starts to see what the flame is worth, the spark that tugs at its interest. And after seconds, mere seconds that felt like years for the little moth it draws near the lonely flame.

Wow, that sounds romantic in a way. My admirer has a way with words, a unique way but it works.

As crude as that analogy is, it is how I felt. I don't know when it happened but at some point in my time seeing glimpses of you around town....I began to notice you. Your mane seemed as radiant as the sun, your green eyes captivated me for seconds at a time. And your body, dare I say it, aroused a lust inside of me that I had not noticed before. You have quite the curves on you, don't let anypony tell you otherwise."

Oh my, that is....wow. My heart is beating awfully fast right now, I think I just got hit a spell of the vapors! Somepony lusted over me, now that sure is something. I feel flattered, and a little hot for some reason. Did somepony raise the temperature in here?

“You okay Cheerilee? Your face looks all red and stuff!” letting out a surprised squeak I shut the letter. Taking a breath I composed myself and looked up to a worried Scootaloo and Twilight.

“I'm fine, just feeling a little warm, does it feel warm in here for you two?” both Scootaloo and Twilight shook their heads, well there goes that excuse. Quick, make up a lie! “Then I guess I must be coming from under something, a cold perhaps. Don't worry about me, heh.”

Thankfully Scootaloo shrugged her shoulders and went back to the board game. Twilight on the other hand gazed at me for a few seconds longer before shrugging as well, that was close. I didn't want to have to explain to a filly and a princess that I was getting all hot and bothered over a letter. I would just die of embarrassment.

Yeah, but you won't. So keep reading! See if he wrote anything smut worthy!” pestered my ever so annoying conscience.

“I was about to! Shut up will ya?” I mentally berated the voice in my head. All I got on his end was silence. I better take advantage of that quietness and get back to reading before he goes on a shrilly tangent.

And most of all when I found that you were a lover of books I could only become more enthralled by you. You see I am a book enthusiast myself, quite a big one in fact. The thought that I had found a pony just as interested in literature as I was, and such a beautiful one at that, excited me. A chance to be together with a individual that loves the same thing that I cherish, I just had to seize the chance. You simply intrigue me, Cheerilee.

I reread that entire passage twice just to let it sink in. I intrigue him? Nopony has ever said I intrigued them, I hadn't thought of myself as that interesting to begin with. But my admirer seems to think otherwise. He thinks I am physically alluring, and we share a hobby. Although mine is a bit on the smuttier side we still share a common interest on something. I think I am beginning to warm up to this mysterious admirer even more now.

I apologize for taking up so much of the letter with my muses about you. And now it would seem that I am running out of space to write. This would be a good as time as any for my three questions to ask of you. My turn to be the interrogator, I would insert a malicious evil laugh here if I could. But kidding aside here is my first question, what book series do you find your favorite?

Now that is a tough one, I have a lot of favorites but it would be dull just to list them all. I should just name a recent series just to make it simple. Next question!

For my second question I would like to know your favorite food, simple I know but it counts!"

My favorite food? Now that is a easy one, key lime pie, no doubt about it. Just the thought of some pie brings my mouth to water.

Thirdly, and forgive me for this somewhat serious question, I would love to know about your views concerning same sex relationships. Do you think it is wrong for a stallion to love a stallion and vice versa for mares? Honestly, from my point of view I don't see anything wrong with it. If two beings truly love one another then what is there to judge? But alas that is my opinion, what is yours?

Quite the touchy subject you're poking me on mister secret admirer. Now if somepony asked this question in public a few decades ago they would probably be shunned for approving same sex couples. But thankfully times have changed and views concerning such couples are in a much brighter light these days. And I can say that I approve of same sex couples, gay or straight. Love is love, and gender should not be used as a way to deny feelings felt for one another.

That's my girl! Whether you do the horizontal with a mare or a stallion, it doesn't matter if love is in the equation! Buck anypony that says otherwise, buck em in the teeth I say!” I rolled my eyes at my conscience's overzealous words but I had to agree with him. Judging a couple based on what gender they prefer is childish and immature. However, I wouldn't buck anypony in the teeth for their opinion, a few strong words of scolding is enough I think.

I agree with you on everything except for the scolding, really sugar?If somepony judged me on my relationship, a few words ain't gonna settle that dispute I'll tell you that right now! If anypony messes with me or my honey I would destroy them, both emotionally and physically! Buck being civilized, if whoever mocks us isn't going to be then why should I?”

Once again I rolled my eyes, he really is quite the overzealous drag queen isn't he?

Buck yes I am! And don't you dare forget it, sugar!” and with that final sassy comment my conscience went silent once more. Taking advantage of the mental silence I began to read right where I left off.

I suppose that's all I can write for questions at the moment, already I curse myself for even presenting the idea of a three question limit! Is there any way I can convince you to reconsider my previous proposition and increase the question count to maybe, I don't know, ten questions? But then again that would probably result in me sending you two to three letters each day. Honestly I have the time to write, but imposing you to do the same would be selfish wouldn't it? And I am rambling on aren't I, please ignore this sentence if you would!”

Ugh, the very thought of writing three letters a day is excruciating! Add three letters a day to my already heavy work schedule of grading and classroom things? No thank you, I already have a ungodly workload to deal with once a week. Sure letter romance is one thing but a shit ton of paper work is another. Wait, is this thing with my admirer a romance? Or is it slowly growing into one?

Alas this is where I shall start to end this letter, my dear Cheerilee. I am running out of space to write and it is high time I say my goodbye anyways. I look forward to reading your next letter with bated breath my dear. And I hope your work week is a easy one, may fortune smile on your future endeavors. Sincerely with love, your secret admirer” I smiled as I read the last sentence, with love huh? Maybe one day I will write the same back to him, maybe.

With that thought in mind I folded the letter closed and tucked it safely back into the purple envelope. As I snapped it closed a single word popped in my head. Love, could this pen pal situation transform into something like that? Where I would finally have a special somepony in my life? It was hard to say, this is only the third letter I received from my admirer. It is way too early to even say I have the same feelings he has for me.

Not with that attitude you won't! Just keep this pen pal thing going and you will get your answer on whether or not you like like this guy. I can feel it in my nonexistent gut!” well at least one of us is optimistic. Maybe my conscience is right, let's just keep riding this pen pal train to see where it goes. What do I have to lose besides free time? But I have plenty of time to think about these things later, I should get back to the board game.

“Alright, I finished my letter now what did I miss?” I said with a yawn. Looking over to my side I saw that they had started another game of monopoly again, and this time Scootaloo was winning from the looks of all those boulevards she was owning.

“Oh nothing, just me totally owning Twilight over here. Nothing big or anything” Scootaloo giggled as she rolled her dice across the board.

“Owning would be over exaggerating, Scootaloo. I just wasn't paying attention is all!” Twilight scowled. Poor Twilight, getting beaten at a board game by a filly. Can't win em all, princess.

“Yeah, sure you were. Why don't we start over and deal Cheerilee in? It'll give you a chance to make up for your losing streak!” Scootaloo teased.

“Oh yeah? How about we make a wager? Twilight and I against you, if you win I will give you extra credit for all your assignments for the rest of the year. But if we win, you will have to help me grade my papers after school for the same amount of time. How about it Scoots?” after a few moments of deliberation Scootaloo agreed with my terms and we reset the game board.

This should be easy.

Hours later....

“I win again! The orange buzzer triumphs once more!” a very, very happy Scootaloo cheered as she bounced up and down on her side of the couch. Twilight and I were simply dumbfounded, our mouths slack jawed as we watched the orange filly knock our pieces over, again. I couldn't believe it, I lost forty six bucking times....to a filly! And I even changed the game several times to even out the score to no avail. Every game I presented her with she just positively owned us each and ever turn.

To make things even more embarrassing, we lost to a child in chess. Chess! Of all the games to lose to a kid on, the one game I thought for sure Twilight and I could win on! I lost track of how many games we tossed out trying to find one to slip Scootaloo up on. We are literally surrounded by discarded game boxes for bucks sakes! And not a single one stumped her.

“Unbelievable, that makes forty five wins for Scootaloo and....one for us....” Twilight muttered as she stared in disbelief at the notched paper before us. How in Equestria did we lose this many times to Scootaloo of all ponies? How?!

“Okay Scootaloo, tel us your secret. How in everything all good and holy did you manage to beat us so many times? And on different board games ranging from monopoly to chess!” I grumbled while folding the chess board back into its respective box. Tossing the infernal chess set along with the other game boxes scattered about.

“Just practice actually, the orphanage has all sorts of games for us fillies to play with. I played with them a lot with the other kids on rainy days or when Sweetie Bell and Apple Bloom were away or something. I guess you're unlucky to have the same board games I had back home. That and my amazing skill was too much for two grown ups to handle may have had another hand at it!” Scootaloo explained all the while giggling like a mad mare.

“Well that explains that I suppose, you'd think your special talent would be in board games” Twilight said with a tired sigh. As soon as Twilight uttered “special talent” Scootaloo's eyes widened, her gaze flicked to her rump. Unfortunately said rump was utterly lacking a cutie mark of any kind. And this made Scootaloo's triumphant smile turn right the hell upside down, can't win em all, girl.

“Don't worry about it, Scootaloo. Your special talent will show up someday just you wait! Keep your chin up” Twilight remarked with a playful nudge to her shoulder. Thankfully her little nudge reversed her frown, but only just so.

“She's right, just keep doing what feels right, that's how I found my cutie mark after all. I still remember the day, you see I-”

“You guys are right, I just gotta keep tryin like I always do! Just gotta keep trying, can't get a cutie mark on giving up anyways!” Scootaloo interrupted me with a cheer of her own. Interrupted again....well at least she's happy now. Anyways, wonder what time it was? Looking over to the clock on the wall it read half past ten, pm might I add.

“Jeezum crow it's getting late, have we really been playing board games all day?” I uttered in disbelief. Glancing out a nearby window my disbelief was confirmed, it was pitch black outside. Well there goes my another day to myself, again.

“Oh my, it's almost eleven! Spike must be worried sick about me, I should probably get going soon” Twilight said as she got up to leave. Oh no you don't!

“Really? You're just going to leave us alone to clean up this mess? You played on half of these board games too you know!” I said with a cross of my hooves. Twilight's response was a awkward smile coupled with a shrug as she used her magic to pick up a few board games near her. That's more like it. And so after a while of clearing the mess we made and tossing the boxes back in the closet the living room was clean once more.

“And looks like that is the last of that, time for-ahn, bed” I tried to stifle a yawn still ended up yawning all the same. Jeez it's late.

“Don't tell me you're tied? Its' not even midnight yet! Let's do something fun! Like make smores or something!” Twilight and I gawked at Scootaloo. She can't be serious?

“Are you sure? You're not even a little bit tired, Scootaloo?” Twilight questioned with a raised eyebrow. Scootaloo's response was a firm nod and a hearty hoof bump against her chest.

“Not even a little bit! I am tough and full of energy! Gunna stay up all night just like Rainbo-aaahn” and there was the tell tale yawn of sleepiness.

“I think it's time for all little fillies to go to bed. Come on Scoots, I'll take you home” I offered the tired pegasus but she shook her head against the very idea.

“Can I sleep here for tonight?” Scootaloo begged, her purple eyes regarding mine with a flash of neediness. That is not fair! Always with those puppy dog eyes of her's, gets me everytime.

“Oh fine, since it's already late and all you can stay the night” I resigned, pinching the bridge of my muzzle with a sigh. Scootaloo on the other hoof cheered, screaming yes over and over again. I looked over to Twilight with a shrug.

“Kids huh?”

“Looks like you got your hooves full tonight, can't say I envy you” aint that the truth. Twilight can go home but here I am stuck with the orange puff ball until morning.

“Alright Scoots, you can take my bed for tonight while I sleep on the couch. Follow me” I called to Scootaloo, motioning a hoof for her to follow. But Scootaloo had other ideas.

“Noooo, I'm to tired to walk! Carry me!” Scootaloo whined as she dramatically swept a hoof over her forehead. I facehooved, she really isn't making this easy for me. But how could I deny her request? How could anypony say no to those big innocent purple eyes? You'd have to be a soulless bastard to resist such cuteness.

“All right, all right come here you big baby” with that said I picked up the orange filly in my hooves. She was surprisingly light, but then again all pegasi are. Something about hollow bones for flying or something I dunno. I don't teach pegasus anatomy class, don't judge me. So with Scootallo safely tucked under one hoof I began the awkward ascent upstairs. Let me tell you that walking upstairs on three legs was uncomfortable, the things I do for my favorite student.

And Twilight was loving every minute of it as she followed us upstairs. She was trying to suppress her laughter but a few giggles here and there escaped. Go ahead and laugh it up Twilight, don't use your magic to help me carry her or anything. And so after a few close calls with the stairs and a tumble in the hallway we made it to the grandeur that was my bedroom.

“Okay Scoots, time for-aww” I couldn't help but coo at the sight of a sleeping Scootaloo. The poor thing fell asleep in my hooves. My goodness she is going to give me a sugar coma if she keeps acting cute.

“Aw, mommy Cheerilee cradling wittle Scootaloo in her arms. why don't you just adopt her already, blegh you two are going to make me gag!” my conscience teased. I just ignored him, it's too late to start a mental argument at this hour. Turning my attention to the filly snoring in my grasp I carefully put the sleeping little filly in bed. Tucking her in until she was nice and snug in a cocoon of bedsheets. And right then and there I did something I couldn't help myself from doing.

I planted a motherly kiss upon her forehead. Scootaloo mumbled a sleepy mumble and smiled in her sleep.

“You would make for a great mother” Twilight's words froze me on the spot. I completely forgot she was here, damn my motherly instincts! I turned to face my offender expecting to see a smug smile. Instead all I saw was a warm smile on her face. “The way you two acted hours earlier and how you two are now, if I didn't know any better you two would be mother and daughter. It's cute!”

Oh Celestia kill me now....

“Ugh, don't tell anypony about this, it'll ruin my street cred” I whispered sarcastically. Twilight just rolled her eyes and silently nodded towards the door. After that awkward moment we carefully and silently made our way back downstairs. I made it to the front door and ushered Twilight as I said my goodbyes. And just like that I was alone, well not entirely alone. I have Scootaloo sleeping upstairs and I have a gay conscience occupying my mind, so I can never be truly alone unfortunately.

Aw don't be that way, sugar. You need your fairy gay mother to tell you what to do when you need me. And this fairy god mother wants you to take your ass to sleep! Go on, off to the couch you go!” and like the drone that I was I adhered to my fairy gay mother, plopping myself on the couch.

“Yeah whatever, it's too late to deal with your smack talk. Goodnight mister nuisance” I grumbled as I let my heavy eyelids close shut.

Goodnight miss impossible. Sweet dreams, sugar” and just like that I was out like a light as I started drifting into the world of dreams. As I began to lose consciousness one thought ran through my mind.

“Tomorrow better be a good day or I swear by Celestia I am bucking somepony in the gut.”

Author's Note:

And chapter 4 is here! I wonder if things will start looking up for our dear Cheerilee? Will that conference with Diamond Tiara's parents go as planned I wonder? Anyways that is all up for debate until chapter 5, mwuahah! But seriously what is up my readers? Did you all have a wonderful day today? If not I am sorry but it will get better! I also apologize for this chapter coming out a little late, I received three projects from my professors. And lo and behold they are all due next Tuesday, fun fun! But I will keep working on this story regardless of my workload, I actually finished two of the three, so cheers for that one! Wow this author's notes is dragging on, I should probably end it here. Until next chapter folks! (Ps: I don't own monopoly, :p PPS: I might edit this chapter, I was up late turning it in so forgive me, I also italicized the admirer's letters as well as the inner conscience speak. What do you guys think about it?)