Chapter 1: Dear Miss Cheerilee...
Chapter 1: Dear Miss Cheerilee…
My alarm rang at 5:30 A.M, declaring the beginning of the first day in another week of school. I slapped the clock to a snooze, giving me time to get myself fully awake before I turned it off completely. With a yawn, stretch, and rubbing the crap out of my eyes, I blinked a few times before making a tired smile.
“This is it,” I said to myself. “Today’s the day, one that will change everything for me for the rest of my life.”
I flicked the lights on with my magic and popped any kinks out of my body when I was off the bed. I looked to my desk where there were two pieces of paper: one notebook of a rough draft, and the other a parchment as the final product, along with a short pencil, a bottle of ink, and a blue writing quill still sitting in its stand. I turned to the trash bin next to the wooden desk. Balled up notebook papers filled it up halfway while some strays were littered around it.
It took a lot for me to write out my best letter throughout the break, I thought, but if things turn out the way I hope today, then the work’s worth it.
I rolled up the parchment and levitated a fancy fuchsia ribbon out from my desk drawer to tie it before I dropped the scroll to the top of my backpack along with my other school supplies. I changed from my pajamas into a white t-shirt and jeans, fidgeting my white tail to get through the hole behind me. I made the bed and cleaned up some of the trash that was around the floor, keeping my room clean like Mom would want it, and went to the living room where I set my things on the couch.
I walked to the kitchen and found a note and a pouch on the table. I pick it up and read aloud, “Minty, I will be out of town for a few days attending a publication meeting in Manehattan. There’s money to help you buy lunch and dinner for that time if you’re not up to cook. Don’t spend it all at once. I’ll be back Wednesday evening. Love you, Mom.” I shrugged, picked up the pouch, and jingled it a little. “Fifty bits in here? Sweet.” I floated it over to my backpack and dropped it inside with a thud. I prepared a quick breakfast of toast with blackberry preserves and milk, then cleaned myself up as soon as I was done.
I checked my appearance in the mirror, my wintergreen fur was smooth with a small sheen from the bathroom light’s reflection, my short white mane groomed to a small spike in the front, my horn was well-filed (but not sharp enough to skewer anything), and my sapphire eyes had subtle bags underneath them.
“Could use some more sleep, but I think I’m good to go,” I said to my reflection. I smacked away any hint of sleep left from my face and took a deep breath. “Alright, let’s do this.” I made my way to the front door, floated my backpack over my shoulder in a deep blue aura, and left with the house locked up.
I made a quick trip through Ponyville’s market where businesses were still opening up for the day, which made sense as the sun was just rising over the horizon. I walked over to an orange earth pony mare with a brown Stetson over her blonde mane tied in a ponytail. She had a button-up short-sleeved flannel shirt, opened just below her collarbone to air out the small beads of sweat on it. She saw me coming over and sported a smile on her face.
“Morning, sugar cube. The usual today?”
“Morning, Applejack. Yes please.”
I come to Applejack’s stand at the start of each week. It’s been like that for the past four years, so I became a favorite regular of hers.
She went to her cart full of apples to pick one up from the stock while I reached down my backpack to get my bag of bits. I gave her four bits in exchange for the apple.
“You do know you only need to pay two bits for the apple, right?” Applejack asked.
“I know, but I’m feeling good today. I thought I’d give a little extra for your time.”
“Well thank you kindly, Minty. Much appreciated.” She tipped her hat to me as I put the apple and bag of bits in my backpack. “Mind if I ask what’s got you in such a good mood? Wait, didn’t you turn eighteen over the break?”
“How’d you know?”
“Apple Bloom was telling me about the party Pinkie Pie threw for you last week. Finally became a stallion, eh? You feel like one?”
“Eh, not really.” I shrugged. “I feel pretty much the same as I usually do. The party was good though.”
“Good to hear. Well, even if you’re an adult now, just remember there’s plenty of fun to have while you have the time, alright?”
“Thanks, Applejack. Have a good one.” I made my way to school while I waved to the apple farmer with a smile.
I checked the time on my watch to read it was 7:00. I looked back up to see the large school building before me. There weren’t many other classmates around me that were waiting for the school to open. Not too later though, the janitor inside started unlocking the doors, letting me and the other students inside. More ponies came as time passed, but the room for my first class of the day was still locked. With time to spare, I decided to hang out in the cafeteria. More students were in the building now, especially in the cafeteria where they were grabbing breakfast or snacks to last throughout the day. It was around this time a few friends of mine started to come in.
“Morning, Minty!” a buttercream colored earth pony filly with a red mane and tail called from afar. She had a pink bow tied to the end of her mane, styled the same as her older sister’s, while wearing a flannel shirt of a different color scheme and jeans. On the left was a white unicorn filly with a curly purple and pink mane and tail, wearing a light green sundress that stretched to her knees. Then there was the third filly on the right, an orange pegasus (that was slightly darker in color than Applejack’s) with a somewhat wild violet mane and tail, wearing a sky blue tank with a tri colored lightning bolt at the center and shorts.
“Morning Apple Bloom, Sweetie Belle, Scootaloo,” I greeted as they took seats around the table.
“You look pretty cheerful today, Minty,” Sweetie Belle commented. “Strange since this is the first day of school after break.”
“What can I say? I’m glad I get to be here again.”
“You’re the only colt I know who actually likes going to school,” Scootaloo said. “Didn’t you do anything over break? Besides the birthday party, that is.”
“I wrote some short stories and read a few books. That’s something.”
“Minty, I know writing stories is your special talent and all, but I think you can do a lot more than sit around doing that all day,” Apple Bloom said. “The only other pony I know that does that stuff for fun is Twilight, and even she has fun adventures with our sisters and their friends outside of the library every now and then.”
“Well, before the library got… you know,” Sweetie Belle pointed out. “Her new castle looks amazing, don’t get me wrong, but I sometimes miss that old library. We did a lot of memorable stuff there.”
“I have seen quite a bit of your… adventures, for sure,” I said. “I know Mom and I moved here because it was her hometown, but with all the craziness that happened here, this place is like a gold mine for stories, and nopony would tell whether it’s fictional or not.”
“Just don’t write any stories that involves other ponies’ personal lives,” Apple Bloom suggested. “Trust us, and it wasn’t helpful Diamond Tiara urged us to make them for publicity neither.”
“Did somepony mention moi?”
“Aw, dammit.”
We turned to the filly mentioned who was standing next to the table. Diamond Tiara was a pink earth pony filly with a wavy purple and white mane and tail. She wore a black skirt and matching knee-high boots, with a light jacket that was a brighter shade of pink (maybe hot?) than her fur over a white frilly chemise, all while sporting her signature tiara like her name implied. Next to her was Silver Spoon, a grey earth pony filly with a silver mane and tail, the former braided. She wore aqua blue framed glasses with a matching sailor uniform with a pearl choker looped around her neck.
“Figured you losers did something boring over spring break,” Diamond Tiara scorned. “Our daddies took us on a cruise outside of Horseshoe Bay. We even got to see a school of dolphins swim by.”
“Pod.”
Diamond Tiara raised a brow at me. “What?”
“You mean a ‘pod’ of dolphins swim by. School is usually referred to groups of fish while pod goes to other marine animals like dolphins, whales, and even hippos.”
“He’s kind of right, you know,” Silver Spoon agreed. Diamond Tiara responded with a glare while her ‘friend’ scrunched her muzzle and looked up. The other three girls snickered at the scene.
Ah, the relationship of evil mastermind and henchmare, I thought. It may have become a cliché, but it never gets old if done right.
Diamond Tiara blew a lock of her mane out of her face. “Whatever, nerd. Stuff like that doesn’t make me the popular filly in school, you know. It takes beauty, grace, and…” she trailed off as it quickly turned into a speech of her greatness. I looked over to the girls, and we nodded on cue that it was time to move out. We quietly got up from our tables and left the cafeteria while Diamond Tiara still ranted about herself.
“Ugh, how can anypony think of her as popular?” Scootaloo asked as we walked. “If we’re talking coolness, Rainbow Dash would win by a landslide. How Diamond Tiara won Homecoming Queen earlier is beyond me.”
“Speaking of dances, Prom’s coming up soon,” Sweetie Belle pointed out. “Have you thought about who you’re going to ask, Minty?”
“Nah. I’m not even planning on going,” I answered.
“But you didn’t even go to junior prom!” Apple Bloom said. “This is our last year in high school for Celestia’s sake! We gotta make the most of it while we can!”
“I’ve been to the few dances on our first year with you three,” I said. “If Prom’s anything like those, I’d rather not be a part of it.”
“Well, alright. But if you change your mind, you’re welcome to hang with us,” Apple Bloom offered.
“I’ll keep it in mind, thanks.” I smiled.
With classes starting soon, we made our separate ways to our designated rooms. A warmth welled within me as I smiled and walked, knowing a certain pony I’ve missed over break will be there. I may have gone later than usual today, but I knew she of all ponies would understand. When I opened the door to the classroom, my vision of reality became brighter, almost sparkling as I saw the pony, my beloved, inside.
“Good morning, Minty,” Miss Cheerilee greeted with a smile. “How was your break?”
“It was good, thanks,” I answered with a smile of my own as I took my seat, not too close to her desk to rouse suspicion, but not too far to not see her radiance. More students poured in as class was beginning to start, not giving me much time to chat with her casually. At the corner of my eye was Diamond Tiara with a glare in my direction as she walked past to a desk behind me, probably annoyed for how we ditched during her boast, but I brushed it off. I took my notebook and pencil out of my backpack and began writing notes when class started, making sure I put every word I heard from the lecture onto paper.
Miss Cheerilee taught Equestrian Literature and Social Studies, both classes I was lucky to be in with her this semester as the first and last classes of the day in respective order. I’ve been entranced by her since day one of my freshpony year. Her fuchsia fur that coated her cello-like figure, her cotton candy-like mane and tail that had a certain bounce to them, and eyes that were green like a calm, grassy field that spanned for miles. Those only made up the icing to the delicious cake of her personality though. Cake… I must be speaking with Pinkie Pie too much to make up such an analogy.
Anyway, not only was she beautiful, but like her cutie mark—three smiling faces on daisies—she cared enough for her students to make sure they grew into magnificent, happy ponies in the future. I was a bookworm long before I started high school, and being in a room with so many different ponies on my first day made me choke up to answer any questions she asked over lecture. She noticed my knowledge in literature though, as she peeked at the correct answers I had written down in my notebook, but never had the courage to speak it out. She talked to me after class for why I didn’t speak up that day, and I told her about how I would get made fun of for being a geek back in junior high. She told me her own experiences that were similar to mine, assuring me that even though we’re not perfect, that shouldn’t stop us from showing what we’re truly capable of. She then pulled out a book from her bag to let me borrow, a fiction that accentuated that point as the moral, and that was when my crush for her bloomed.
Ever since then, I read every book Miss Cheerilee suggested to me after class. I would go straight to the library (that now resided in Twilight’s castle) to check them out and read almost immediately when I got home. Every first day of the week I visited Applejack’s stand to pick up Miss Cheerilee’s favorite apple to give while I excelled in her classes, and we talked about the books she suggested to me. She became more of a friend to me than a teacher, and my fondness for her grew stronger by the day. I know my love for her may be hopeless by most. Crazy, perhaps even forbidden for somepony so much older than I am, but that’s one of her best features in my perspective. Unlike fillies around my age, Miss Cheerilee was a mare. Yes, ponies like Sweetie Belle, Apple Bloom and Scootaloo may look cute, and they’ve seen more things in life than other ponies their age did, but not only did Miss Cheerilee have experience, she had the wisdom to back it up too, and was generous enough to share that knowledge with her students so they can grow to be fine ponies as well. That caring, sweet nature of hers was what got me through my school days, even so eager enough to go just to see her smiling face.
And now, I was going to express all of it to her today like I vowed years ago: to profess my feelings for her as soon as I reached the age of adulthood, and I worked through most of my break to write the perfect letter I currently hold in my backpack.
The bell rang in the classroom, waking me up from my note-taking trance throughout the lecture as the other students packed up their things and left for their next class. I stayed behind until everypony left like usual, leaving me alone with Miss Cheerilee for the time until more students came for the next class of the day.
“Here you go,” I said as I placed her favorite apple on the desk.
“Thank you, Minty.” Miss Cheerilee smiled. “You know what’s funny is that I almost expected you to walk into my home just to give me this apple last week. It’s become quite a routine for me to think about something like that.”
If I knew where you live, I’d bring an apple to your door every week, even during school breaks… Wow, that didn’t sound stalker-creepy enough, I thought.
“Oh! Before I forget, I believe I remember it was somepony’s birthday last week.” She reached into her bag with a grin and pulled out a brown leathered book with a red ribbon tied into a bow at the center.
“Miss Cheerilee, you shouldn’t have,” I said as I took the book and untied the ribbon.
“I figured a good fiction writer would need a good journal to write all their story ideas down. You deserve it.”
I opened the book and flipped through the many blank pages. At the inside of the cover I saw a message in beautiful writing.
Make the world yours to create, and show the readers how far your imaginations fly.
Cheerilee
At the ‘i’ in her name was a cute heart in place of the dot on top. I tried to hold back tears welling up in my eyes while a burn was growing hotter in my chest.
This is a gift she gave to me, I thought. I will treasure this journal until the day I die. “Thank you, Miss Cheerilee, I love it.” I smiled with a few sniffles.
“I’m glad. Now you best get to your next class before you’re late. I don’t want to be the cause for your tardiness.” She smirked.
“Y-Yes, of course… but, do you mind if I talk to you after your last class today?”
“Of course, Minty. You’re welcome to come talk to me about anything.”
“Okay. Thank you. I’ll see you later then.” I quickly packed my new journal and supplies in my backpack with my magic and walked quickly to my next class. As I made my way though, I suddenly broke out in a cold sweat, my hands turned clammy and trembled, and my throat dried up. Okay… This just got much harder now, I thought.
I took my seat in the next class for the day. My head scrambled with second thoughts while I stared ahead.
“Hey Minty,” Sweetie Belle greeted as she took her usual seat next to me. Her smile suddenly disappeared as her eyes widened in my direction. “Whoa, are you feeling alright? You don’t look too good.”
“Huh? Me? No, I’m feeling just dandy,” I said while still looking ahead, my eye twitching every couple of seconds.
“Okay, now I know something’s wrong. You’re doing that twitching thing when you lie.”
Crap, is my tell that easy to read? “Alright, maybe there’s something on my mind, but it doesn’t have anything to do with you.”
Class began before Sweetie Belle had a chance to respond. I only heard bits and pieces of the lecture, something about Clover’s law of celestial matter like the sun and moon or other, but I was too distracted by what will come later to pay any close attention… That was until a few taps on my arm caught it.
I looked to the source to see a folded paper that I quickly took without the teacher noticing. I glanced to the corner of my eye to see Sweetie Belle looking in my direction with folded ears. I opened up the note to find a short message.
It may not have anything to do with me, but that doesn’t mean I shouldn’t leave you alone when you clearly need help. Please, Minty? You’ve helped me get through a lot of these classes, at least let me try to return the favor.
I know they won’t understand where I’m coming from if I tell the truth, I thought, but… It’s a little reassuring to know I’m not alone, and I have friends like Sweetie Belle looking out for me. I sighed internally in defeat before I wrote out my response to pass back to her.
I’ll give you and the other two the details over lunch.
“So, something’s bothering Minty?” Scootaloo asked as we sat in one of the cafeteria tables with our lunches.
“Yeah, he was all shaky and sweaty when I talked to him last class," Sweetie Belle explained. “He was defensive of saying anything at first, but I convinced him to at least tell us what’s going on.” The girls looked at me, waiting for an explanation about my troubles.
Crap, what do I say? If I tell them I’m scared of confessing my love to just a filly they’d be all over me and possibly do anything to help make it perfect, and from what they’ve told me about their adventures, help is probably the last thing I need from the three of them. Not to mention, I can’t lie if my lie is that easy to read like Sweetie Belle pointed out. “Uh… Where do I start?” I asked.
“How about what happened in your first class?” Sweetie Belle asked. “You looked fine before that, and it wasn’t until later you looked like you were about to have a stroke or something.”
“Don’t you got Miss Cheerilee for that class?” Apple Bloom asked.
“And Diamond Tiara’s in there too,” Scootaloo deadpanned and widened her eyes. “Wait, that’s it, isn’t it? She’s planning something awful for you, isn’t she?”
At this point, I’d take that as the truth than what’s really going on. “No, it’s not that,” I answered. “The worst she did was give me a death glare for ditching her speech earlier.”
“Alright, then did you find out you flunked out on a test in her class?” Apple Bloom asked. “And Miss Cheerilee asked you to stay after school to talk?”
Oddly enough, she’s on the right track. “You could say that,” I said while scratching my head.
“That’s weird, you’ve always scored high in literature,” Sweetie Belle pointed out, “and I don’t see you as somepony who’d freak out over one or two points off from a perfect score.”
“Twilight was like that once,” Scootaloo said. “Remember when—mph!”
“Scoots, we agreed to never speak of that,” Apple Bloom interrupted while putting a hand over her muzzle, her brow furrowed. “Never again.”
I’m suddenly intrigued to know what happened, but it looks like I won’t get any answers anytime soon. “In any case, I do have to stay after school today to speak with her, but when she asks what’s up, I’m not sure if what I’ll say may be approved.” I looked down with ears folded. “I… really looked up to her for a while, and I’m afraid whatever happens will be responded in a negative way.”
“Hmm…” Sweetie Belle closed her eyes and hummed for a bit.
“I guess that makes sense,” Apple Bloom agreed with a nod. “She’s been a great teacher for us. She may get a little stern with us when we did something wrong, but she’s not one to hold a grudge.”
“Yeah, she just makes sure we learn something from it and move on from there,” Scootaloo added in. “She’s pretty great with things like that.”
“I’m sure Miss Cheerilee will understand if you tell her the truth,” Sweetie Belle said with her eyes open to me. “Even if things may not turn out the way you hope, at least it’s out in the open and know what will happen then.”
“I guess.” The warning bell rang, letting everypony in the building know we have a couple minutes before our next class.
“Guess we should get going. Good luck with her, Minty,” Apple Bloom said.
“Yeah. Hang in there, dude,” Scootaloo added before they took off.
I finished my lunch and heaved my backpack over my shoulder. When I picked up my leftovers to throw away, a hand on my shoulder stopped me. I turned to see Sweetie Belle still there, standing next to me.
“Hey… and just remember that no matter what happens, things always turn out okay in the end, alright?” She gave a small smile that I couldn’t help but mimic.
“Alright, I got it. Thanks, Sweetie Belle.”
“Do you want me to stay behind for moral support?”
“I think I can manage, but thanks. I’ll see you later.”
She then gave me a brief hug before picking up her bag and walked off to her next class. I guess I needed to talk after all, I thought. It’s nice to know you have support from friends like her. I’m sure Sweetie Belle will make a colt very lucky to have her someday. With that, I tossed my trash in the can and walked to my next class, a little better before I came in, but still nervous for what’s to come.
Third class passed by quickly before I made it to the last one for the day. Cheerilee was finishing talking to some students with questions about an assignment as I took my seat. Cheerilee looked over to me after the students left and smiled. I mimicked in return, and though hers was calming, my smile was concealing the nervousness inside me. Class started once the rest of the students for the period took their seats, save for a few that didn’t show for various reasons. Sweetie Belle sat next to me up front, and Silver Spoon was one desk behind on the other side. I glanced up a few times from my notes to momentarily stare at Miss Cheerilee’s butt while she wrote on the chalkboard. I would look back down and continue writing notes once she turned around, and I cursed myself for ogling her like that.
Damn my young colt hormones, I thought as I wrote. I know she’s an amazing mare, but is it even right for me to objectify her like that? It’s her personality and maturity that I like, dammit, not her body… then again, I guess her body’s considered mature, unlike the fillies in the school who may still be developing. And don’t even get me started on her breasts either, if just a few buttons on her shirt were undone—NO! Bad Minty! BAD!
“Minty?”
“Huh?” I blinked myself back in reality to see Cheerilee patiently waiting for something while the rest of the classroom was staring at me.
“The Neighna Lisa painting by Reinardo da Vinci, do you know what year it was created?” Miss Cheerilee asked.
“Uh… Was it in the mid-1500s?” I asked.
“Close. Silver Spoon?”
“The early 1500s, around 1517 to be specific.”
“Correct, and it was one of the biggest influences in the Renaissance period of art in Neightaly, changing the public’s ideal vision of beauty...” Miss Cheerilee went on with the lecture as she wrote more on the chalkboard. At the corner of my eye was Silver Spoon sticking her tongue out while pulling one of her bottom eyelids down.
Oh fuck you, Silver Spoon, I thought. It was just this morning Diamond Tiara almost burned you down with her glare for being smart. Don’t try to push that off to the side like that.
The final bell for the day rang, snapping me out of my thoughts while everypony else started packing.
“Okay class, read pages one-sixteen to one-forty, and we’ll continue where we left off tomorrow,” Miss Cheerilee said. “Have a nice day, everypony!”
As the number of students dwindled down, a touch on my shoulder surprised me, only to find out it was Sweetie Belle with a smile. “Good luck,” she whispered. She picked up her things and left the classroom, leaving only me and Miss Cheerilee in the room once the door clicked shut. My heart started racing like a hummingbird’s wing flaps.
“So Minty,” Miss Cheerilee said. “What was it you need to talk about? Something important?”
“Y-Yes, it is to me,” I answered as I opened up my backpack and took out my scroll. “There’s something I’ve been wanting to tell you for a while, and I think I’m ready to do it now.” I took a deep breath and walked up to Miss Cheerilee who was sitting patiently at her desk with a slightly raised brow. I undid the ribbon on my scroll, set it to the side of her desk, and unrolled the letter. I cleared my throat and started reading from the beginning.
“Dear Miss Cheerilee, I have learned a lot of things while taking your classes for the past four years here in Ponyville High. You taught me how I shouldn’t be ashamed of my strengths when others look down on it, what it means to have a good friend, to be a good friend, and something I didn’t expect that I myself still can’t believe to this day.
“I had little knowledge of what it was at first before I moved here from Canterlot. I was almost scared to even learn about it when my own parents couldn’t maintain it for so long, scared to admit that the feelings you have for them will slowly fade away until there’s nothing left. To this day I still don’t understand why it came to be, and I’m afraid to even ask my mom about it and whether I’ll end up with the same outcome… But then I had my first class with you during my freshpony year.
“I honestly didn’t know what it was at first, maybe a little bit, but I was in disbelief of it even being possible. It grew as I talked to you more over the years, and it was becoming hopeless of me to look away from it when it was so obvious to see. I couldn’t stop thinking about you when I didn’t have school. School breaks—intended to give students and teachers time off for themselves to enjoy—was torture for me for not seeing you in your desk with your cheerful smile. Don’t even get me started on summer vacation either. I’d be the luckiest colt in the world just to say hello to you outside of the classroom. The cheerful smile I mentioned before, your caring nature for us students, your generosity to give us the knowledge we need to harness our strengths, and your kindness to guide us in the right direction despite our wrongdoings. I couldn’t begin to tell you how much of those alone makes you the most beautiful mare in the world, and how it gives me the excitement to come see and talk to you every day at school.
“And now we come to the answers of the burning questions of the day: What is the thing I didn’t expect to learn? The thing that I’m afraid to get my mind around with my parents’ experiences in it? The thing that gives me woe when I don’t see you? The thing that gives me energy to come to school every day? These and other unanswered questions come to one phrase that makes everything clear that I come to you to profess today.
“I love you, Miss Cheerilee. Even if your feelings may not be the same, I hope you’ll at least come to accept mine as fact. Your faithful student, Minty.”
I rolled up the scroll and tied it closed with the ribbon once more, a long breath sighed out for finally getting my feelings out in the open. I looked to Miss Cheerilee with her eyes wide open, her jaw slightly down. After a moment she closed her eyes and took a deep breath.
“Minty,” she said with her eyes open, and a slightly furrowed brow. “We need to talk. Do you have anything important to do later tonight?
I was afraid of this, I thought. “No. My mom’s out of town and won’t be back until Wednesday evening.”
“I see…” She looked up with a flick in one of her ears while rubbing her chin. “Would you mind if we continue this at my place?”
Okay, that, I did not see coming. “Uh... sure, I don’t mind.”
She took out a pen and paper and wrote something down before handing it to me. “Come to this address at 6:00. Don’t plan on eating anything before then. I’ll have some food prepared when you get there. Understand?”
“O-Okay.” I folded the address and slipped it in my pocket. “I’ll… see you later then.”
“Yes. I’ll see you soon, Minty.”
I put my scroll on Miss Cheerilee’s desk and walked out of the classroom. There weren’t any other students in the hallways, and I sighed a shaky breath while rubbing my eyes.
I am totally boned, I thought as I made my way out the school. She must want to take this someplace private so she’d let me down easy, maybe even discuss why a relationship between ponies of such a big difference in ages is taboo and recommend some doctor to check on my sanity. Even if I’m a legal adult now, I’m not sure if she’ll still get in trouble with the public that could lose her job. Crap, I didn’t even think about that. This may be for the best though, I don’t want to cause any more trouble for her than I already have. At least I’ll get to have some of her cooking—probably my first and last meal to be made by her—and I finally got my feelings for her out in the open between us. I guess all I can do now is bide my time until I face the music.
I lost track for how long it took me to get back home, or how I ended up on my bed staring up to the ceiling. There were some moments where I visualized Miss Cheerilee’s glorious ass wiggling in front of my face, how she slowly unbuttoned her shirt down until she let them slip out, leaving her only in a bra of some design I didn’t put much thought into at the time, and for some reason, how she’d spoon feed me oatmeal like we were some kind of lovey-dovey couple. I didn’t care how hard my boner was during that time. If I was shameless enough to fall in love with my own teacher, having a tent pitched out in the open would be the last thing I’d worry about.
I blinked a few times as my senses came back to reality and glanced at the clock, which read 5:00.
It’s almost time, I thought. If I’m going to get turned down, I might as well do it while looking somewhat good. I hopped out of my bed and went to the shower to freshen up. Once I was cleaned, I put on a fresh change of casual clothes and styled my mane with some pomade. When I made sure everything about me was tidy enough, I locked the door as I left the house.
“Let’s see… the place should be around here,” I said to myself as I looked at Miss Cheerilee’s address. I tilted my head up and found a light red house, one story. Small, but pretty much around the same size as any household around Ponyville. I swallowed my anxiety down and took a deep breath before I knocked on the door.
“Who is it?” Miss Cheerilee’s voice called from inside.
“It’s Minty.”
“The door’s open.” I turned the knob and slowly pushed open the door.
The first thing that overwhelmed me was a scent that felt like it exploded out of the house once an opening was found. It smelled familiar, but I’ve never experienced such concentration of it to this degree before. I came to one conclusion to what that smell was to only one simple phrase:
This place smells like Miss Cheerilee.
I was so focused on this somewhat arousing scent I didn’t notice another being mixed into it, which was the food Miss Cheerilee cooked for the evening. It smelled delicious, but I suddenly remembered why I was here and all thoughts on those two scents were shoved aside. I closed the door behind me as I walked inside and looked around. There was a large collection of books in a shelf that almost touched the ceiling along with a few knick-knacks. There was also a small table next to it that had some photos, a coffee table in the center of the living room, and two couches on opposite sides. Further up the room was the dining table, big enough to seat six, and a few pots with food steaming while two sets of plates, glasses of water, and tableware were sitting at one end on opposite sides.
“Go ahead and have a seat. I’ll be up in a second,” Miss Cheerilee said.
“Okay.” I took the seat with the plate closest to me and waited. I looked into the kitchen across from me and saw Miss Cheerilee putting the last touches onto some dish with her back turned to me. I scrolled down her curvy frame until I saw her ass where her tail twitched momentarily. I sighed inwardly while I tried to look away from it.
I hate to admit that I do have some sort of lust for her amazing body, but I still remember why I love her in the first place, which I think is what counts the most, right? Still, I don’t blame her for being skeptical of me even if I try to explain myself.
With pot holders in each hand, Miss Cheerilee carried the last dish to the table and set it next to the others before taking a seat across from me. “Go ahead and have some helpings, and we’ll talk once there’s some food in us.”
“Yes ma’am.” I served myself some mashed potatoes, green bean casserole, corn, and a slice of garlic bread on my plate. Over the next couple of minutes we ate in silence. I was too down to even look up and see her beautiful face, feared that I may only get some kind of disappointing look that could break my heart.
“Is the food okay?” she asked.
It’s so delicious I could cry. “Yes,” I answered without looking up.
“I see you’re understanding how serious this situation is,” she inquired.
“I do understand,” I said. “I didn’t think about it until I got home today how risky it was for me to open up something like that to you, but I just couldn’t keep that a secret anymore, and I didn’t think of any better place to meet and talk than your classroom after school, where we always had our chats. Think all you want, but everything I read out loud from that letter today was entirely the truth.” Tears started to well up while I sniffled. “I’m sorry… if my feelings for you seem repulsive, coming from a high school student like me. Before you do your worst, would it be too much to ask of me for us to just be friends? That much alone would mean the world to me after everything you’ve done, and I just don’t want to lose you.”
I choked on my sobs as I tried my best to not break down with my eyes tightly closed. My salty tears dripped down to my plate, making some of the leftovers on it taste less appetizing.
Suddenly, something dabbed my tears away, making me gasp from surprise. What I saw was the same caring smile that I came to love as Miss Cheerilee was leaning over the table to clean my face with her napkin.
“A pony should never be repulsed by somepony’s feelings towards them,” she said as she sat back down, finished with wiping my face. “Besides, why would I turn down such a handsome young stallion such as yourself?”
“H-Huh? I don’t understand. Didn’t you invite me here to tell me why it’s bad for me to love somepony older than I am?”
“Mr. Minty, are you implying that I’m old?”
“Wait, n-no no! That’s not what I, I mean you don’t look old, but—!” I was suddenly interrupted by Miss Cheerilee’s guffaws. I am so lost, I thought.
“Oh relax, I’m only giving you a hard time,” she said as she wiped her eyes from any stray tears from her fit. “No, Minty, I didn’t call you here to discuss that.”
“Then what did you call me here for?”
“Where things will go between us.”
… Huh?
“You see, I’ve met my fair share of stallions before I became a teacher,” she explained as she looked up and leaned her head on her hand. “A few left me for another, had some one-time flings, and I was honestly beginning to lose hope of ever finding that special somepony, especially after learning how being a teacher is apparently a turn-off. I still love my job though, and I wouldn’t drop it for anypony no matter the circumstances.
“But then I had you in one of my classes.” She looked over to me with a smirk. “You were so cute when you first attended, and I admit, I didn’t have a single thought about seeing somepony younger than me. But then you showed how mature and knowledgeable you are compared to the other students, especially when we talked about the books I suggested. Then you got older, went through puberty, and one day I saw you in class, I thought, ‘You know? I’d probably go for a guy like that. Shame that he probably sees me as an old hag, or I might have given him a try.’”
Am I… Am I hearing things correctly? Did she just say she had some kind of interest in me?
“But you definitely proved me wrong after hearing what you read to me today,” she continued as she placed a hand to her chest with a smile. “I have never seen a stallion so expressive about his feelings before you came along, Minty. I had to make sure you left before I cried from how touched I was. So I did some thinking after I calmed down and came home, and I just need to be absolutely sure.” Her brow furrowed slightly while her smile lessened. “Is everything what you’ve said in that letter true, Minty? Do you really find me beautiful and love me?”
My heart suddenly raced once more as I wasn’t sure where this was going, so I said the first thing that came to mind, straight from the heart. “Y-yes. I have loved you for quite some time, and think you’re the most beautiful mare in all of Equestria. Those stallions you saw in the past had no idea what they were missing out on.”
A moment of silence passed through the air. It was like Miss Cheerilee was holding that expression for hours before she slowly formed a smile while closing her eyes halfway.
“I see. In that case…”
I gasped as I suddenly felt something under the table rubbing my crotch, which was big and hard, but easy as it treated me with care. My pants were suddenly getting tighter as I shivered in place, Miss Cheerilee’s half-lidded gaze boring right into me. “M-Miss Cheer—”
“Shhh,” she hushed me. “Outside of school, you may call me Cheerilee. Now… how would you like to have some fun with a real mare, hm?” My crotch was pressed into me harder as it was rubbed up. I looked down and see a fuchsia colored hoof feeling me up.
Holy shit, my teacher’s giving me a hoofjob, I thought. Did I just die and go to heaven? Dear Luna, if this is a dream, please don’t wake me up. “I… I’m not sure if I know how.”
“I’ll teach you,” she whispered as she slowly undid her buttons from her neck down, far enough to see her cleavage and the laces of the black bra her breasts were squeezed in. She stood up from her seat and sauntered over to my side, my gaze going directly towards her bosom once she turns my seat towards her. “How about it, Minty?” She puts her hands on my shoulders, leans forward to where her breasts were hanging down, and her hot breath on my ear. “Shall I give you a private study session?”
“Oh Faust yes please,” I replied.
She moved down and meshed her lips with mine. My first kiss with her couldn’t have been more perfect. The food from dinner was subtle in taste, but I couldn’t believe how soft and smooth Cheerilee’s lips were. The moan that escaped from her mouth drove me over the edge as my heart was about to explode. Our first kiss ended with a smack, purely drunk from the sensation I open my eyes halfway to meet hers in a daze.
She giggled as she wrapped her arms around my head. “I have to go freshen up. Do you mind clearing everything here and wait for me in my room until I’m done?”
“Of course, my love,” I answered dumbly.
“Oh, and bring some fruit, whipped cream, and wine from the fridge while you’re at it,” she continued. “I believe we should share your first drink before I treat you to some dessert.” She gives me one more brief kiss before trailing her finger up my chin, making my spine tingle. “I’ll see you soon~,” she sang. Cheerilee then straightened up and sauntered to her room with extra movements in her hips. She peeked back to me, cracked her tail like a whip and grinned before disappearing in the next room.
With renewed vigor in my system, I quickly cleared the table with my magic. I put leftovers in tupperware for later, cleaned the pots and tableware, and put them in their designated cupboards and washer. I open the fridge to put the contained food inside, and see a bowl of strawberries, a can of whipped cream, a bottle of white wine still corked closed, and two glasses. I exchanged the items and looked for a wine opener with panting breath. I stopped when I realized I was getting antsy, and took a few deep breaths.
“Okay Minty, calm down,” I said myself. “You’re about to make love with Mi—I mean Cheerilee, but that doesn’t give you an excuse to behave like a wild animal. Remember why she took a liking to you in the first place, and you make damn sure you treat her like a goddess. Now… where did she put that wine opener?” I look around with a clear mind and found it hanging on the side of the fridge. I use it to pull out the cork from the bottle with a pop, and I smelled its scent. Mom wasn’t much of a drinker so she doesn’t carry alcohol around the house. I think she promised to share a drink with me at one point when I’m at the age, but having my first with my teacher, my friend, my beloved, sounds so much better right now.
After I made sure the front door was locked, I carried the things to Cheerilee’s room with my magic and took in its design while I heard the running water from the bathroom to my left. The walls were a nice shade of pink like her mane and tail, her queen sized bed had purple sheets and a large nightstand next to it with a lamp. I decided to set the things there and poured the chilled wine into the cooled glasses. I put the cork back in once I was done and sat on Cheerilee’s bed to wait… and then I fully realized I was on her bed.
This is where she sleeps every night, I thought. I grabbed one of the pillows and gave a few squeezes. Soft, fluffy, seems well used. I pressed the pillow against my face and took a few whiffs. This smells like her too, the whole bed does… Wonder when was the last time she cleaned this? I put the pillow back in its rightful place with a few pats.
Wait, how is she going to come back out? Am I going to see the rest of her underwear? Something else I didn’t think she’d have? Should I strip down? I was at a loss for what I should do, so I just tossed my jacket to the side of the floor. My ears perked as I heard the water stop running. She’s almost here, I thought. After a few moments of silence I heard the door open a crack.
“Minty? Are you there?” Cheerilee asked.
“I’m here. I got the stuff you asked for.” When the door opened fully, my eyes widened while my jaw dropped.
There was my love in all her glory. She had the bra from before on, yes, but from the waist down was eye-catching. Attached to her frilly black panties were garters pulling up thigh-high stockings, fitting all around her legs down to her hooves, accentuating their healthy thickness.
“Do you like?” she asked with a smile as she came up to the bed. She did a little spin so I could see all of her. Along with her cutie marks I saw how her panties were practically disappearing between her cheeks, thanks to her tail moved aside so I could get a full view.
“You look incredible, Cheerilee,” I praised.
She turned around and giggled. “Why thank you.” She crawled on the bed with half-lidded eyes her tail raised extra high, like a predator about to pounce on their prey. When she got next to me, she spun to a sitting position, but not without using her tail to brush up under my chin, giving me a sensual shiver. “Could you pass the wine to me please?”
“Of course,” I took both of our glasses and handed one over to her. She held hers up to prepare a toast.
“A toast to us, to the beginning of our new relationship, and your first step to becoming a stallion,” she declared.
We smiled as we clinked glasses and I took a few sips. I flinched from the first strong taste of alcohol in my system as I finished my sample and cleared my throat.
“Don’t worry, you’ll obtain the taste once you try other options,” Cheerilee assured. “Though it’s not high on the content, I suggest not going through it too fast.”
“Duly noted.”
“So are you nervous?”
“Very. I didn’t think any of this would ever happen. How do you even have an interest in me, if you don’t mind me asking?”
She took a few more sips from her drink before answering. “Well you certainly show more maturity for your age compared to the colts around the time I was your age, while at the same time you get like any other curious colt to get so interested in fillies, like how you stared at me in a particular place sometimes.”
I wasn’t sure if the alcohol kicked in quick enough, but my face heated up as I took a few larger takes of wine than before and looked down. “You noticed even that, huh?”
“Eh, it happens with colts sometimes, but I’ll make an exception for you.” She winked. “Besides, I sometimes notice how cute your butt can be, so I think we can call that even.”
She thinks my butt is cute. I’m not sure if I should be happy, embarrassed, or both… yeah, probably both. “So you’ve never thought of dating a stallion younger than you?” I held up the wine bottle towards her, and she obliged with a nod while holding her glass in front.
“I have dated younger stallions before, just not to such a significant difference in ages,” she answered as I poured her more wine to a good amount before I filled my own glass. “Some of them were pretty immature though, like they were more interested in my body than me before they moved on.” She took a few swigs of her glass.
“That’s awful. You deserve much better than that.” I took a swig of my own wine and set the glass down to pick up the bowl of strawberries and whipped cream. With a few shakes of the can, I squirted a good amount on a berry and held it up to her. “But how do you know I’m not like those other guys?”
“Because they weren’t knowledgeable and mature enough to put so much thought into expressing themselves like you did.” She grasped my wrist and ate the strawberry out of my hand. She moaned while trying to lick the cream out of my fingers in her mouth, and shiver went from there to my spine, down to my member that was already semi-hard since she came in.
Thank Celestia I washed my hands after cleaning the dishes.
She let go of my fingers with a pop and licked her lips while giving me a half-lidded gaze. “Delicious.” She finished the rest of her wine, took another one of the berries and did something unexpected: She dropped it in her cleavage and sprayed a dollop of whipped cream above it, enough where I couldn’t see it. She looked up to me with a grin, I could barely see a tint of red in her fuchsia cheeks while she giggled and pushed her breasts together. “Come and get it. Make sure you get everything off of me too.”
I downed the rest of my wine and put our glasses on the nightstand. I scooted close to Cheerilee enough to come face to face with her mounds. Holding them in my hands, I licked and ate the whipped cream off her cleavage. She giggled once I got between her mounds and ate the strawberry off her chest. The berry seemed to have a different taste that didn’t come from the cream, her sweat probably coated it while it was down there, but that just made it all the more delicious.
When I licked the last of the cream out of her breasts, she chuckled once more as she saw my muzzle covered with the stuff, making me look like a rabid dog. I stopped myself from licking it clean when I had an idea. I took another strawberry and held it in my mouth.
“Hmm?” I hummed as I tapped the berry.
“Oooo, don’t mind if I do.” She held my face in her hands and slowly licked the cream off my muzzle. I snorted from the excitement rushing through me I felt her soft, moist tongue around my lips. When she got to the strawberry, she put her mouth over mine and breathed out heavily through her nose once she pulled the fruit inside her. She chewed a few and licked my upper lip. I obliged and opened my mouth, engaging our tongues in a wrestle while exchanging the strawberry’s juices.
From there we took turns in how we creatively ate the strawberries—or just the whipped cream alone—from each other’s bodies. Cheerilee pulled my shirt over my head and tossed it next to my jacket on the floor, making room to spray whipped cream on my neck and the berries over my chest to eat off from there. I breathed shaky breaths while my body shivered under her thorough, delicate care she delivered with her teeth and tongue. She unclasped her bra to set her amazing breasts free, and I sprayed whipped cream over her tits to lick them off, lingering a bit to give them proper ministrations that made her coo in delight. At one point I put another berry in her belly button and sprayed whipped cream around it, making her chuckle as I licked and ate them off of her. In between our turns she chugged the rest of the wine straight from the bottle, which only had about a quarter of it left. I was both impressed and strangely aroused from how hot she looked while doing that. I heard her younger sister owns a bar in town and she’s quite an experienced drinker. Maybe that kind of thing just runs in the family.
Our eat-off went on until we came to the last cream covered strawberry in her hand, which I ate off of like she did with mine at the beginning. There was something enlightening to licking and sucking somepony’s fingers. Though it was cleaned, you’re licking off of something that’s been in places only its owner knows. Cheerilee, for example, used it to hold the pen she uses to grade our essays, ate something before tonight that she had to lick her own fingers clean, maybe even on some poor lonely nights where she pleasured herself with that same hand. It was one of those times where it’s so wrong, yet so right at the same time, and I was in bliss that it was Cheerilee’s hand I’m doing it with, or it could be that the alcohol’s finally kicking in and I just paid the smaller details no mind.
I let go of her fingers with a pop and sighed. “I’m stuffed… and a bit tipsy,” I said before I hiccupped.
“Told ya it will kick in quickly,” she said with a giggle.
“Hey, you’re in the same boat too, young lady. You chugged the rest of that bottle down like water, and I bet you’ll end up worse than I am.”
“… You think I’m young?”
“Pfft, duh. I may not know your age, but you’re—you’re still in your fucking prime. Everything about you appearance-wise is fucking awesome, excuse—hic—excuse my language, especially your sexy butt.”
Cheerilee paused, then snickered before rolling on the bed laughing. “Are you that into my butt Minty?!” she asked in between laughs. “It’s so fat though.”
“What? What’s that got to do with anything? H-Hold on,” letting the alcohol influence me, I grabbed her cheeks while she was on her stomach, eliciting a gasp from my drunk lover/teacher. “Hmm…” I gave them a couple good groping squeezes with her panties still on, shifted them up and down, open and closed, pressed and rubbed them together, and circle them around, making Cheerilee moan while her tail twitched. “There’s a good balance between firm and jiggly, mobility is a level ten in fun levels,” I said in a different voice, playing like some sort of scientist doing an analysis. “Dear Luna, in all my years of glutitology, I have never seen such a magnificent buttox! We must perform the raspberry test to make my final conclusion.”
“R-Raspberry test?” Cheerilee asked in between snickers. “What’s a Rasp—?”
“PBBBBBBTH!” With my lips on one of her butt cheeks, I blew a ton of air on it to make a loud farting noise, causing Cheerilee to laugh hysterically. If there’s one thing I’ve learned from my tickle fights with Mom when I was little, it’s that no matter the circumstances, the raspberry will overpower anypony. “It’s just as I hypothesized, Miss Cheerilee,” I acted after I was finished. “Your buttox wouldn’t compare to even Princess Celestia herself! You should feel very proud.”
“Why thank you, Doctor Minty,” Cheerilee said after she calmed down and put the empty bowl and whipped cream on the night stand. “I simply must repay you for your professional analysis.”
“And how do you plan on doing that?”
“By doing this,” she gave me one more kiss that was soft and tender, the kind we shared for the first time that I came to love immediately. She slid her hand down my stomach to the hem of my pants, unbuttoning, unzipping, and pulling them down. I helped with slipping them off, leaving me with a tent made from my boxers standing up front while a wet spot was found at the tip. Cheerilee grabbed the waistband and pulled them down, freeing my hardness to stand at attention.
“Somepony looks excited to get started, and he isn’t the only one.” Cheerilee gently pushed me down on her bed, unclasp the garters holding her stockings, and slowly slipped them down with a grin. Finally, she shimmied herself out of her panties, now fully nude, and playfully flung it right on my muzzle. I took a big whiff of her soaked undergarments, catching a strong scent of her raspberry flavored musk.
“Mother of Celestia,” I breathed.
“Is this your first time, Minty?” Cheerilee asked as she straddled the top of my erection, her wetness coating it as she grinded, making me groan.
“Y-Yes, and…” My face heated up and I glanced to the side. “Though it’s shameful for me to admit, I sometimes masturbate to fantasies of us doing something like this.”
“Aww, well let me tell you two things, Minty,” she bent down, and with a finger under my chin, directed my gaze to her caring smile. “One, there’s nothing wrong with masturbating to things like this. Everypony does it, including me, and it’s normal to have such urges. Two, as of tonight, I’ll be making your fantasies come true.” Our lips connected with soft and care, I brought my arms behind her to get a feel for her ass, eliciting a moan from her as we kissed. Our mouths parted and Cheerilee moved up to my ear. “Relax, and let me take care of everything. I’ll be gentle,” she whispered. She gave my ear a gentle nibble, eliciting a shallow gasp from me before she pulled back.
With my hardness lubed enough with her liquids, she rose up and directed my flared head to her core. Cheerilee slowly dropped down, moaning with a bit lower lip while I gasped from the softness that was pulling me inside. She stopped right at my medial ring, and with a little force, she screamed as I popped right inside, fully bottoming me out.
“Goodness, you’ve got quite a girth. My clit just rubs right over you, I can barely stand it,” she breathed as she grinded up and down. My hardness rubbed against her moist softness that was getting wetter, while at the same time getting squeezed from the bottom up. The throbs from me was against her pulses enveloping around me, as if her insides got smaller for just an instant, but the moment was long enough for me to experience and save it in my memories to remember for quite some time.
“I… can feel everything inside you,” I grunted. “Your heartbeat, heat, softness, wetness, your desire to milk me dry, I’m loving all of it.”
“I want you to fill me up inside, Minty. Fill me with your love enough so that they never leak out. Give it all to me, Minty!” She started to bounce on top of me, the sounds of our bodies coming together, Cheerilee’s pants with her tongue lolling out, and my grunts as I helped lift her up by the ass before the drops were filling the room. She rose up just above my medial ring before dropping down, the up and down squeezes from earlier intensified with the addition of going further up her core. More of her warm liquids were oozing out and coating my girth, slick enough to cause wet, smacking noises upon contact, and the sensations all the more sensitive for me—and hopefully Cheerilee as well—to experience.
“Cheerilee!” I grasped her cheeks harder and pumped her faster on top of me. I felt something build up in my loins. I gritted my teeth and tightened my entire self to reach the final stretch. “I love you!”
“I love you too!” We screamed in sync, I thrust up inside her, and unloaded my load. Cheerilee’s body shivered, pounded herself down, and as soon as I climaxed, her orgasm came in a burst. Our expulsions mixed together and leaked out as our bodies clapped the last few times with our spurts. With little energy to hold up, Cheerilee fell down on top of me and wheezed while her arms were around my head. My own arms wrapped around her middle while I caught my breath, the hard thumps from our heart beats settled down to harmony with our chests pressed together, savoring the warm, messy, but delightful afterglow.
“Cheerilee?”
“Yeah?”
“Are we dead?”
“No, why?”
“I thought we came ourselves to heaven for a moment there.”
Cheerilee giggled and shifted herself to where our eyes locked onto each other. “I felt the same way when I had my first time.”
“Was this okay?”
“It was wonderful.”
“I’m glad. Though next time I’ll pull my weight to give you the treatment you rightfully deserve.”
“I’ll take you up on that.” We connected lips and I savored the warm feelings that added into the wonderful afterglow inside. Cheerilee then nuzzled against my chest and I stroked her slightly frazzled, but still lovely mane while she swished her tail across our legs.
“I should probably get home before things get too dark, huh?” I asked.
“Probably, but let’s just stay like this for a bit longer.”
“I’m okay with that.” I kissed the top of her head and sighed. “I love you, Cheerilee.”
“I love you too, Minty.”