Following the Leeder

by gimmick68

Rating: teen
Tags: Cheerilee, Big Macintosh, Slice of Life, My Little Pony: Friendship is Magic, Other
Length: 2936

Parent-teacher conferences have taken a turn for the weird and Cheerilee is trying to figure out why. She pieces the puzzle together to discover why.

The latest round of parent-teacher conferences have Cheerilee perplexed. Something is definitely different about this night. As the night goes on, she tries to figure out what is so weird about it.

Rated teen for adult themes.
Cover art by me.

Published 2016-08-13 23:30:12 UTC
Last updated 2016-08-13 23:30:12 UTC

In Which Cheerilee Ruminates over Curious Occurrences

Something seemed off. She couldn’t quite put her hoof on it but Cheerilee knew something was definitely off. She scrunched her snout in thought. Her mind tried to piece together the oddness of this evening. It wasn’t a surreal kind of oddness but one that instead announced itself as a subtle kink in the status quo.

She idly shuffled some papers on her desk and took a folder from the pile. It contained the grades and performances notes on one of her students. She read the name and took a deep breath. Depending on which parent was coming, this meeting could be tense or less tense. If both showed, it would be downright uncomfortable.

She glanced up to the clock on the wall; still two minutes until the next scheduled meeting. She glanced out the window. No sign of anypony in the evening light. She decided to ruminate. Typically, she enjoyed ruminating – the thrill of pondering, the excitement of musing, and the sheer pleasure of contemplation brought her such happiness and such contentment. However, this evening had caused that enjoyment to give way to intent. She was after something: an answer. What was off about this evening?

She pursed her lips as her mind began its mission. She decided it would be best to start at the beginning, or at least the beginning of the day. Everything to that point had been normal. The fillies and colts had filtered into the schoolhouse and took their seats, waiting for their teacher’s instruction. The day proceeded with little incident, save for some residual snotty remarks from an otherwise reformed Diamond Tiara. (Cheerilee was going to have to talk about that in about one minute). The class still had some leftover excitement from the Applewood Derby, which had taken place the previous week. Fortunately, and despite the distraction it caused, the event seemed to spur their interest in physics. Of course, she toned it down some from her initial lesson on the subject. These were, after all, just children she was teaching.

After a little more thought she found nothing during the day that would be enough to pique her teacher sense. (Her teacher sense, as she liked to call it, monitored the classroom environment to make sure everything remained stable and conducive to learning). There was nothing during the day that posed a threat to her conception of normalcy. So it had to be this evening that was the culprit.

A pony clearing their throat brought Cheerilee out of her rumination. “Oh, Mr. Rich, please come in.”

Filthy Rich stepped into the schoolhouse. She greeted him with her usual smile. As he took his seat she took the opportunity to quickly glance at the doorway. Nopony had followed him in. “Will your wife be joining us?” she asked as nonchalantly as possible.

“No, she felt that only I needed to come tonight.”

Yay! “Oh, that's too bad. Very well, then.” She couldn’t place exactly what it was but she felt like he wasn’t telling the entire truth. But Filthy Rich, despite his shrewd business practices, was an honest pony when it came to one-on-one interactions. That’s something Cheerilee appreciated about him. Still, something bothered her about what he said. It sounded so familiar.

The meeting with Filthy Rich went well. Cheerilee was very proud of Diamond Tiara for turning over a new leaf. She beamed as she told him his daughter was doing much better in class and her demeanor and attitude had vastly improved. Of course, she did have to bring up those remarks she made during class today. Filthy Rich handled the whole conference very well. He listened and didn’t interrupt and he responded in a calm and collected manner. He said he was happy to hear of his daughter’s improvement and that he would continue to nurture her new outlook on life. Eventually, the conversation turned to small talk, of which Filthy Rich was doing the most. After about five more minutes Cheerilee had to cut the conversation short in order to prepare for the next parent.

“Thank you again, Mr. Rich, for coming in tonight.”

“No, thank you, Miss Cheerilee. I’m so proud to hear Diamond Tiara is doing so much better. I almost regret telling my wife she needn’t come tonight.” He chuckled but Cheerilee was a bit stunned by his admission. She chuckled along to keep up appearances.

Mr. Rich left, but not before extolling another barrage of thank you’s, well-wishes, offers of discounts at his store and invitations to his home for dinner. She accepted and reciprocated the thank you and well-wishes but politely declined the discounts and dinner.

Cheerilee sat at her desk and thought about the conference that just occurred. It had gone from fairly formulaic to positively peculiar in a hurry. Between he and his wife, Filthy Rich was the level-headed one. Still, he had managed to get a bit defensive in the past when Cheerilee brought up Diamond Tiara’s bullying and poor behavior. But tonight…nothing but smiles and agreements. Maybe the news that his daughter had turned a corner had nulled any inclination to confront Cheerilee on her accusations. But to offer an invitation to dinner? Highly unorthodox.

She thought about that bit. In her mind it was tantamount to accepting a bribe to take him up on his offer. But it didn’t make sense to bribe her since Diamond Tiara had become a much better student. Nope, not one bit of sense. She thought more.

The minutes ticked by as she prepared for her next conference. She pulled the folder off the dwindling pile. It was the second to last conference. She read the name. She sighed. It wasn’t going to be bad, just…interesting.

In the meantime, she continued her rumination. Armed with a new piece of the puzzle she set to work. Filthy Rich had not been the first parent tonight to offer something to her. Snips’ father offered her free mane cuts and styling for a month. When she refused, he added a month to sweeten the deal, and so on. He also made several remarks on the beauty of her mane - from a barber’s perspective, he was quick to add. But other parents also offered gifts of sorts. For instance, Twist’s father offered Cheerilee two tickets to the grand opening of the Ancient Romane exhibit at the Equestrian Historical Museum in Manehatten. It was an offer difficult to turn down but she did.
However, more concerning was that Filthy Rich wasn’t the only parent to request her company for dinner. Silver Spoon’s father had charmed his way into nearly coaxing a date out of her. Had she not had her wits about her she would have been in a situation she would lament. She scoffed at the thought. Surely the mothers of the children wouldn’t have made her those kinds of offers.

And then it hit her.

The lightbulb shone brightly. The pieces fell into place. She knew what it was. Every parent that had come in for conferences had been the father. Not a single mother had shown up tonight. Sure, she had noticed their absence but didn’t think too much of it. She had shrugged it off as happenstance. But now she saw the missing mothers as a contributing factor to the weirdness of the evening. Typically, mothers outnumber fathers two to one at these parent-teacher conferences. And yet, here not one had shown up. But why not?
Just when she was set to dig into that thought a knock came on the door.

“Miss Cheerilee, may I come in now?”

“Oh! Yes, please do. I’m sorry. I was lost in thought.”

“No problem, dere,” offered Hondo Flanks.

“Okay, well, I’m happy to say Sweetie Belle is doing well in class. She’s still having…” She trailed off and her eyes stared into the distance.

“Miss Cheerilee, ya okay there?”

“Umm…yes. I was just wondering if your wife happens to be around.”

“Nope. She’s back at da house cookin’ up a storm, dontchaknow. Gotta campin’ trip all set up for da weekend.”

“Sounds lovely.”

“Yep. Gonna go with some friends of ours. But there’s a lotta food to be made so I told her not ta worry about the parent-teacher conference, ya know.”

Of course you did. It was all coming together. “Very thoughtful. Now –”

“Yer welcome ta join us, y’know. The more the merrier.”

“Oh, thank you, but I’m afraid I can’t. I, uhh…well, I just can’t. Sorry.”

“Too bad. Woulda loved ta have ya.”

“Yes. Well, as I was saying about Sweetie Belle…”

The rest of the conference went smoothly. Obviously Cheerilee had to discuss some of Sweetie’s shortcomings, especially in math and geography, as well as a few lingering antics she and her friends participated in. Sweetie Belle saw the world differently: if viewing the minutiae of life’s processes could be viewed under a microscope, Sweetie’s microscope was also a kaleidoscope. Overall, Sweetie Belle was slightly above average and tracking upwards. With a final bout of chit chat Hondo Flanks left, but not before offering the camping trip once more. She politely declined and saw him out. Yet another father trying to bribe her. What was it with these stallions?

Cheerilee’s job entailed many a curious occurrence. The children were as anypony would expect: their obedience and attention could be turned off in an instant if given the chance. Her job was to make sure that didn’t happen. Overall, she did an admirable job of keeping her class in line. Sure, once in a while there were some incidents, but nothing she really couldn’t handle. But children were naturally oddballs in their own right and as such put her at the locus of strange things. But this evening was something different entirely. Between the no-show mothers and the fathers who were a bit too forward with their intentions, Cheerilee was experiencing a brand new type of weird.

She shook her head, trying to shake off the weirdness. After all that had transpired this evening she needed a rest. But she couldn’t get one just yet. She reached for the last folder and looked at the name. Her stomach attracted some butterflies as she read the name over and over. If the previous conferences were any indication of what was to come, then she knew exactly who would be walking through the door next. The thought of the next stallion triggered another thought: Maybe it wasn’t her teacher sense that noticed the peculiarity of the evening. Maybe it was another part of her, a part of her which did not see much playing time. Maybe it was a mare’s intuition that noticed the oddity of it all.

She was no stranger to receiving attention from the stallions in town. It was one of the perks and pitfalls of being a single attractive schoolteacher. However, this evening was different because it was so much at once and so sudden, brought on by an unknown force. And for everything that transpired to do so in a setting like this…She’d never even considered it was possible. She ruminated a bit more: So, the fathers had all miraculously convinced their wives to stay home from parent-teacher conferences so they could have some one-on-one time with me in order to get on my good side. It seemed so far-fetched and yet it was what all the evidence was pointing to.

One more conference to go and she could leave. But then, considering with whom the last conference was going be she didn’t really see the necessity in leaving right away.

“Miss Cheerilee?”

“Ah!” She jumped a little. The voice had an immediate calming effect on her, however, and she smiled at the red stallion poking his head in the door. “Big Mac, please come in.”

“Sorry ta scare ya like that,” he quietly said, taking the seat across from her. “Ah wasn’t inneruptin’ anythin’, was Ah?”

“No, Big Mac, it’s fine. It’s been an odd sort of evening, that’s all.”

“Ah see. Well, Ah guess I don’ wanna take up much of yer time, so whenever yer ready…”

“Oh, don’t worry about it. I’m in no hurry with you.” She swallowed her ‘eep’ and blushed profusely in the wake of the last two words that escaped her mouth. She and Big Mac shared an awkward stare. Attempting to recover quickly she began discussing Apple Bloom’s grades. The youngest Apple was similar to her friend, Sweetie Belle. She caused small amounts of mischief and had a bit of trouble in two subjects, history and math. But other than that she was a delight to have in the classroom.

“Big Mac, may I ask you something?” Cheerilee asked, as the official business came to a close.

“Eyup.”

“Why did you come here tonight?” Big Mac cocked his head in confusion. “What I mean is, why you and not Applejack or Granny Smith?”

“Jus’ mah turn, that’s all,” he said with a shrug.

“Oh.” Just his turn. Cheerilee tried to fit that piece in with all the others. It didn’t match.

“So you’re not here to bribe me?”

“Bribe ya? Fer what?” The poor stallion was clearly perplexed.

“Oh, nothing, I guess. Just a passing thought. Like I said, it’s been an odd sort of evening.” The two sat in silence, both listening to the tick tock of the clock, both trying to figure each other out. Cheerilee bit her bottom lip as she mulled over her next move.

“Big Mac, may I tell you something in confidence?” She wouldn’t have asked if she didn’t trust his fidelity to a secret.

“Eyup.”

“Well, it’s been a weird evening. All the parents that came in for the conferences were the fathers. Just the fathers. And they’ve been offering me all sorts of gifts and inviting me to dinner. I don’t what happened to cause this. I’ve never gotten this much attention before, at least not at parent-teacher conferences. Especially not here. I think these stallions were making passes at me.”

Big Mac appeared to find some discomfort in her admission. “W-why would they do that?”

“I’m not entirely sure. Besides the obvious reasons, of course. But this has never happened before. I can’t figure out why all of a sudden they would be doing this.”

“Well, Ah din’t wanna say nuthin’, but Ah think Ah know why. Y’all looked mighty pretty in that outfit last week.” He quickly shifted his eyes away and did his best to fight back the blush. “Lotsa ponies been talkin’ ‘bout it, ‘specially tha stallions.”

“Oh.” Cheerilee blushed as red as Big Mac. Primarily it was Big Mac calling her pretty that caused the blush. However, a small part of it was the realization that it was she that had ultimately been the cause of offness of the night. The culmination of the peculiar evening was wrapped up in a single sentence: “Lotsa ponies been talkin’ ‘bout it, ‘specially tha stallions.”

Cheerilee groaned and facehoofed hard. She’d worn a cheerleader uniform for the Applewood Derby. It wasn’t meant to be anything but a little bit of fun for the ponies, especially the children. She just wanted everypony to enjoy the derby as much as possible. She thought the outfit would add a little more celebratory flavor to the day. Clearly it had an effect that she did not intend and that she had completely overlooked.

“Y’alright, Cheerilee,” Big Mac asked, genuinely concerned.

“I will be,” she sighed. A silence fell over the classroom. She crossed her hooves on the desk and looked intently into Big Mac’s eyes. The red stallion nodded in agreement. “Big Mac, I want you to be honest with me. When did you decide to be the one to come in tonight?”

“Well, Ah guess bin a couple months now. Granny an’ Applejack an’ me decided to do these meetins in a rotation, like Ah said. Ain’t nuthin’ more to it than that.”

“So it had nothing to do with my cheerleading outfit?”

“Nope. Why would that matter?”

“I had thought…that, well, maybe the fathers were coming in tonight not to hear about their children’s performance in class but just to see me. Because of that outfit.” Cheerilee put a hoof to her mouth. “Oh, that sounded incredibly narcissistic, didn’t it?”

“Reckon Ah don’t know ‘xactly what ya mean. But if it’s bad then you ain’t it.”

She smiled. “Thank you, Big Mac.” He always knew exactly what to say.

“Guess yer probably right, tho’. Lotta them stallions that bin talkin’ ‘bout ya also got fillies in yer class. I ken see howya mighta figured they’d be bribin’ ya. Get on yer good side ‘n all, give their kids good grades.”

“I guess now that I know the truth I wish it was just a matter of bribery.” Cheerilee sighed in resignation. “I guess I should have known that would happen. But that doesn’t excuse those stallions’ behavior!” she said firmly. “I’ll have to put a stop to it immediately.” Once again Big Mac nodded his agreement and silence enveloped the two ponies. At length, Big Mac spoke.

“But Ah ken see the attraction, y’al’ bein’ in that outfit ‘n all. Tho’, in tha end, Ah guess Ah don’t see what all the fuss is about. What Ah mean is y’all don’t need it, though. The costume, Ah mean. Y’all are pretty ‘nuff without it.”

Cheerilee short-circuited. Her mind caught his words and framed them behind conservation glass. She let out a happy little sigh.

A+ for Apple Bloom.