You started reluctantly following your future teacher. She seemed to have a destination in mind as she started walking from where she came. She was, like every other mare, a cutie. And since you were going to be her student. You wanted to make a good impression.
"So ummm… what do you want to talk about Miss Cheerilee? Is it about me being in your class soon?"
She shook her head "No, though, now that you mention it… I noticed you don't seem too nervous about starting school in a place you aren't familiar with. I've never seen that before"
...Oh… you were supposed to be nervous about that? SHIFTING GEARS. "W-well, I'm a little nervous. There's gonna be a lot of kids there I never met… I hope they like me… I'm kinda scared that they won't"
"Well don't be. If it makes you feel better, I don't tolerate bullying in my class. And besides, as I understand it. I've heard from three certain students that you joined their club."
This… was a pretty casual conversation… huh. You felt pretty comfortable with this. "Oh… you mean AppleBloom and her friends? Y-yeah, they made me a crusader like them. It was… uhh… Well, it made me feel welcome."
Cheerilee giggled "I heard you actually had a little difficulty with that. Is it true you don't really care about Cutie Marks, Anon?"
...How to answer that?...Seems they have either been blabbing or they have been overheard. "...uhhmm...well. It's not that I don't care. It's just. Well..." She was an adult. Surely she would understand this reasoning. Maybe, you could actually have a sensible conversation without it being "HOLY SHIT YOU NEED A CUTIE MARK ANON!"
"I don't want to be defined by a single skill. I know they represent your "Special Talent". I don't want other ponies to look at me and say "Oh, he does this" or "He's only really only good at this one thing". I've given it some thought. Sometimes I think getting a Cutie Mark is a good idea, but when I'm alone and I think about it. It just seems to be a label to me. I mean, what if I'm equally good at like… five things?"
Cheerilee at first seemed a little confounded by your answer, she had to think. You started to think nobody your "age" has ever challenged such a concept before. "Well, Anon. I can already tell you that you'd be great on a debate team because that's a good argument" Cheerilee said to you, but she was smiling about it.
"Seriously? does that mean… uhhh... That I have a good point? That I'm right?"
"Well, you definitely have a good point. But I can't say if you're right or wrong Anon. There has never been a case where anypony, not even the princesses themselve, have ever been good at five things equally. But, if in the case that a pony was most skilled in five different areas, I would think the skill that ,even by a small tiny amount that goes over the four others, would be their Cutie Mark. Since that would be their "Special Talent". To put it simply Anon, a pony can be good at a lot of things, but they'd also have that one thing they are the very best at."
Ok, maybe five was reaching. "Well...uhh..how about a pony equally good at two things then?"
Cheerilee giggled "Come on Anon, do you know anypony that's equally skilled at two different things, it's a little unrealistic for anypony to have the exact same skill in two different arts, no?"
...ugh… no… most likely not. Even on Earth a guy can be multi talented but to expect them to be equally skilled in two different things. That was only in the movies. "...no, I guess not"
Cheerilee had to stop to laugh. It seems she found something about your answer funny.
It made you feel a little perturbed. "What's so funny?"
Cheerilee had to calm her giggling to give you an answer "Ohhohehe.. It's.. It's nothing. It's just. Here I am walking with a colt and I can swear I actually speaking to a Stallion. You're very intelligent for being very young Anon. Has anypony ever told you that?"
Yeah… Fluttershy… until Discord rekt you with that quiz. Still, even then. You couldn't feel honest about your intelligence since you weren't actually a kid. "Some ponies have..."
Cheerilee noticed your less than enthusiastic answer "What's the matter Anon?"
Nope, you don't want her wondering anything about that. You look up at her and smile.
"Oh no it's nothing. I'm just a little nervous. I mean, I haven't even really met you and now I'm walking with you alone. It's sort of..odd to me"
Cheerilee gave you a big big beaming smile "Well don't, I don't know how it was back at your orphanage. But Ponyville is one of the nicest places you could ever find yourself in. The ponies here, we help each other and look after one another and everypony usually always has a positive outlook on things. So don't worry, I'm not going to hit you… still, I guess you'd be a little on edge after what happened..."
She focuses on your black eye. "Nopony, especially one so young should have to go through what you went through… Anon, I hope those thugs didn't leave an impression on you. That kind of thing is very rare here."
Yeah… thugs are rare. Things like monsters and crazy chaos gods aren't. Still, she took your reaction the wrong way and was only trying to make you feel more comfortable.
"Thanks Miss Cheerilee… You're pretty nice for a teacher"
Cheerilee smirked "That's because you haven't broken any of my rules yet."
And you didn't plan to either. It shouldn't be that hard to obey a few school rules. "I don't plan to either. I don't know what impression you may have gotten due to my Dad, but I can assure you I'm pretty good at following the rules."
Cheerilee didn't say anything though, she stopped, to ponder at your words.
You were wondering why she suddenly stopped, was it something you said? "Anon, did you take any kind of special schooling before you came here?" Cheerilee asked, curious
"What do you mean?" ...You started to think she noticed you're higher than normal kid intelligence.
"Well, It's just very rare for me to speak with a student who can use the words you use appropriately and can do such critical thinking. Usually when I speak to one of my students it's about sillier things. And here we are having a civilized and intelligent debate about Cutie Marks. I just thought you may have had some sort of higher form of education."
You shake your head, you didn't need her thinking into that. "No no nope, I just uhhh..I like to think a lot. Specially with who my dad is. I mean, haha. Being the son of the spirit of chaos really makes a pony think."
"Hmmm..." Cheerilee looked at you as if there was something more. But as she thought, she started to think that maybe prodding would be a bad idea. She actually had something related to Discord to ask you and she had fallen off track. And most of all she didn't want to upset you by digging into you about the subject too much. "Well then, I can only say I expect your work and effort to reflect all that deep thinking you do."
At first you wanted to groan… but you didn't. You didn't need too. You probably didn't need to put in too much effort at all. It was all kid stuff. But like everything else, best to give a smile and a salute. "Can do Miss Cheerilee!" And she followed suit with a smile.
You both arrived at a small garden with a few benches around, and a gazebo as well. The sun was finally starting to set, making the sky turn a golden orange. She sets her groceries down and takes a seat on a bench, and then invites you to sit next to her.
...Well, this was oddly romantic. But you didn't want to hesitate or stand around. Lest yet another female says something about… those kinds of things. But you did have to ask. "Why are we here Miss Cheerilee? I mean, this place seems a little secluded, don't you think?"
She didn't seem to understand your context, and just answered normally while looking up to the sky "I just thought this would be a good place to sit down and talk." She then looked at you, she looked pretty serious all of a sudden..."There's a few things I want to ask about you and your father. I don't mean to pry. But I always want to make sure all of my students, future or current, are doing alright."
So that's it. Even despite Discord's ruse, she still was worried about it all. Well… considering his display back at the school. She probably had good reasons to still worry about it. Being the adopted kid of a former villain would definitely raise some red flags. She was taking the opportunity to talk to you in a nice relaxing place to essentially interrogate you without it seeming too personal. Well, that's fine. You should be able to answer any question she might have without error.
But first, you had a question of your own. You wanted to understand why she took you to this bench..exactly. "Questions huh? Do you take all your students to secluded spots to ask them questions?”
Cheerilee shook her head "Not usually no, I talk to them after school, or if they want to talk to me alone about something they feel is important then I'll let them choose the spot. And I guess since I happened to bump into you that I'd be the one to ask you questions in a place that was serene and relaxing… Do you understand?"
You nod, that seemed reasonable. Miss Cheerilee probably had a deeper connection to her students than most. Considering she seemed to be the only goddamn teacher in town and she always seemed nice and caring on the show. It came to no surprise she'd actually take a more active role in her students care.
"Yeah, I got it. I'll answer any question you might have. I've got nothing to hide"
Cheerilee seemed a little surprised with that answer, she didn't think you'd be so forthcoming. She didn't even know where to start "oh..hmm..So I can ask you any question, and you won't hide anything from me?"
You shake your head. You wouldn't be held back by the guilt of having to lie about your relationship with Discord. The ends justified the means. Just as long as you weren't lying about EVERYTHING. "Nope, I'm like an open book. And just to show you, if you had a question about him abusing me in anyway. Then the answer is a big "no""
Cheerilee didn't say a thing. She had a whole round about way of getting to that line of questioning and you just unexpectedly nipped it in the bud. "Well… that's very good to know. hmmm.."
Seems she was stunned by your straightforwardness. You started to think if you could anticipate her questions. You could get them over with without her getting to a question you'd have trouble answering or make some sort of contradictory statement.
"..oh and he feeds me super healthy food, and he has shown me around town. I even got to meet Princess Twilight! oh, and I have my own room with books and a light and even a nice warm bed. And..AND..." You reach into your saddle bag and pull out the bag of bits and the map. "He gave me these!"
Cheerilee was definitely astonished now. Finally, your initiative seemed to finally pay off. Without a word, she pokes at the bag of bits, and when she heard the clanking of coins… "Wow...that's a pretty good amount of bits he gave you. Why did he give you so much?"
"Dunno… all he told me is that I could use it on whatever I want. I haven't got the chance to spend it… and looking at the sun. I don't think I'll get the chance to. I don't mind though, it's been an interesting day"
Cheerilee just looks up at the sun again. She couldn't think of any questions to actually ask now. You managed to convince her without getting into a whole series of questions you felt would be worthless. Looking at her, she was pretty cute. And being alone with her like this...You felt you had to ask a question of your own… but which one.
"Miss Cheerilee, can I ask you a question?"
She giggles "You might as well, since you just decided to give me all the answers before I could ask a single question"
"Well..uhh..I was just wondering...."
...No, you couldn't ask her about Big Mac...it'd seem to suspicious..But they did make a cute couple. You had to think of something else. You wanted to ask her something that never was addressed in the show… but what?! Dammit, she didn't have much to her… nah fuck it, it's hug time. There was something about these ponies that made hugs extra snuggly and warming to the heart. "...ummm....can I have a hug?"
Cheerilee again was surprised, she didn't expect that after you showed off your "Intelligence". "A hug?"
You nod. "Yeah...I like hugging, it makes me feel warm"
Unbeknownst to you, you had just made Cheerilee feel awful. She concluded the only reason you'd ask for a hug from a pony you barely knew was due to not having a mother. The only other student she knew who didn't have parents was Applebloom, but she had her sister, granny, and brother. You… well, she couldn't imagine Discord being too affectionate. As a teacher who cares about her student's well being, she couldn't say no.
She didn't even say a thing. She just wrapped you around her front legs and gave you a gentle squeeze. Unlike Fluttershy however, it didn't last as long as you'd hope. She gives you a gentle smile
Yeah… that was good enough. Just like every other mare. Her hug was calming, soothing, loving. It had to be this place itself. You knew when you got a hug. It was because they genuinely cared.
But then Cheerilee began to giggle again. it seems something struck her as funny.
"Did I do something funny?" You asked. Confused
She shook her head "No, I actually thought you asking for a hug was sweet. But now that I think about it. It seems pretty funny that'd you'd be so smart and yet ask for a hug. I hope you don't mind me asking what brought that along, do you?" She thought she already knew the answer. But she wanted to know how you felt. Because if it was a mother issue. She wanted to help you get through it with a few more helpful words.
"Umm..well.." Of course she'd ask. Asking for a hug out of the blue? Whatever, it was worth it. Because it also told you what kind of pony you'd be dealing with as a teacher. As long as you followed her rules then you'd have no issue with her. meaning no complications. And her caring nature means you could ask her for help in case you needed it. Equestrian history was, as proven by Discord, a little lost on you. "Well… don't go telling anypony..but I just like getting hugs from mares who are nice..it just makes me feel happy. I guess that's one of the reasons I like my Aunt Fluttershy, she gives me lots of hugs."
You didn't mind telling miss Cheerilee this. If anything you figured she'd keep it a secret and it'd help with making a connection with her. The kind of connection that'd hopefully mean she'd be as gentle natured as possible with you. It wasn't that you didn't mind gruff or hardened personalities. But they were all so goddamn cute. One of the things you remember from the boards you frequent was everyone wanting to hug the ponies, even cuddle fucking was a thing.
Welp, you were living the dream baby. You could even imagine hugging that commie pony Starlight Glimmer… almost… she was pretty sexy but she didn't seem too affectionate. Either way, you doubt you'd ever get a chance to meet her. Sad, you wonder what would happen if you butt heads with her about Cutie Marks… and hopefully not get magic zapped.
Miss Cheerilee gave you a shorter bonus hug and a pat on the head "You know, it makes me feel happy too. I now don't have any kind of worry that something might be wrong. Infact.." She laughs "You might actually make Discord a nice guy if you keep that up, considering he went after those two thugs that hurt you. I can already imagine he's already on the right track to bettering himself."
Miss Cheerilee then looked up at the sky and noticed it was getting dark. "Oh my! I didn't even realize it was getting so late… Anon, do you need me to escort you home? It's the last I can do keeping you here for so long"
You shake your head as you grab your map. "No need" You notice a fountain and walk close to it. All you had to do was toss the map into a body of water you could fit through. This seemed good enough. "In fact, I don't think you could get me home. Considering I live in another dimension. Here, check this out!"
You toss the map into the fountain. Causing the water to turn purple and swirl until it opens up to reveal your room on the other side. Neat! "See? Dad even gave me a super convenient way of getting home. So say, even if I got lost. I could just go home by tossing my map into a body of water. Cool huh?"
Yeah, that was pretty damn cool. This was the first time seeing it. You felt like a cool little magic caster from an RPG. even if the act was simple to do.
Cheerilee just stared at the whirling portal. She wasn't amazed at the portal itself. Magic was a normal thing of course. She was more amazed that Discord was being so generous with you. And looking at your room through the portal. It was just as you said it was. She didn't answer you back however, she just stared at the portal.
You toss your Saddle Bag into the portal, and it goes right on top of the bed… seems safe enough. You look up into the sky, it was indeed getting pretty dark. You look at Cheerilee. You took a moment to think about what transpired. Yeah, It probably wasn't too weird she spoke to you one on one like this. She was just worried about your situation and took the opportunity to make sure things were fine. It's not like she hasn't taken an active roll before. Her and Big mac did end up punishing the CMC for their own crazy antics with that love poison.
"It was nice talking with you Miss Cheerilee… you have a safe trip home ok?"
Miss Cheerilee smiled at you, yeah...she figured you'd be fine. But she was gonna stick around and make sure the portal didn't frag you or something "It was nice talking with you too Anon. I hope when you come to my class that you utilize that brain of yours for creative and wonderful things"
You nod as you begin to climb over the fountain's outer ledge. "I will, I promise. Seeya when I seeya!" And with that, you plop into the portal as Cheerilee waves and watches. The portal instantly closes behind you as it pops and turns back into the map. falling right beside you as you land on your bed
You snuggle up to your pillow a little as it gave off that radiant magical warmth. Everything was going fine so far. Every pony you've met besides two have been nice to you. You couldn't complain. It felt nice to be loved… loved… yeah, actually, there was a problem… two problems… you had to make sure to nip that in the bud tomorrow. For now, you'd relax… maybe see if Discord was home and see what he is up to.