Cheerilee knows two things: she's an earth pony and she loves being a teacher at Ponyville Elementary. Nevermind the fact her mother was a pegasus and both her father and older brother are unicorns, the latter of whom just got married to an earth pony with a better teaching job than Cheerilee. It doesn't bother her, because she just loves being unable to find a higher paying job than what she has now. Really. She isn't that serious when she absentmindedly wonders if being a unicorn would improve her job prospects.

So with all that in mind, she isn't happy at all when she wakes up to discover she has spontaneously turned into a pegasus, a change that goes far deeper than just sticking wings on her back. And the trials she has to go through as a result of her new status will make her call into question just who she is and what she really wants out of life.

Rated Teen for references to alcohol and minor sexual humor.

Credit for the Cheerilee vector used for the cover image goes to J-Brony

*Featured 7/18/14 and 7/19/14*

One night, as Cheerilee is grading her students' papers, Apple Bloom arrives at her home and shows her a new contraption: a portable oven that holds many different items and keeps them warm at the same time. Cheerilee is selected to sample some of them, and soon, Cheerilee finds herself sampling more than "some" of the treats.

This is written specifically for the group My Not-So-Little Pony. It is meant to appeal to the fat/feederism fetish. This is a warning.

It was only a few days ago when I lost my voice and Fluttershy had to sing in my place with the Ponytones. Then, just the other mornin', Rarity's asked me out to a big fancy dinner in downtown Ponyville. What could this mean? Have I done somethin' wrong? Is she finally kickin' me out of the quartet? Or, even worse, could an elegant unicorn like that actually be interested in a stallion like me?

I ain't no good at reading ponies, and I'm even worse at speakin' my thoughts out loud. Rarity is a nice, elegant lady, and I'd be a plum fool to hurt her feelings. Still, the truth's gotta come out somehow. There's only one mare in this-here town who strikes my fancy, and it ain't her.

Based on an idea given to me by Propmaster.

Sometimes I just hated going to school with all of those stupid foals. None of them were as pretty or awesome as I was back then. They all thought that I was really mean to them, but what did they know?

At least, that's what I thought at the time. One day I had to have a talk with Ms. Cheerilee about it, and I didn't like what she had to say...

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Now with a dramatic reading!

Twist has been waiting for something for a long long time. Now, it appears that that day has finally come, and the little filly can barely contain herself throughout the school day.

It's been a crazy Hearts and Hooves Day for Cheerilee and Big Macintosh thanks to the antics of the Cutie Mark Crusaders. It's been a while since the two have had a chance to catch up, so they use their picnic at the gazebo to talk. Turns out there is a good deal to talk about.

It really was a very nice hat she'd given Spike.

Even though Twilight gave it back to her after his rampage was over, Cheerilee doesn't want to keep it.

She really should give it back to him.

*An alternate ending to The Secret of My Excess

Editing and Idea wall support given by Minds Eye
Pre-reading and adding a missing 'i' done by Syeekoh

Cheerilee, the local schoolmare, finds herself feeling abnormally lonely on Hearts and Hooves Day. However, a note she finds may change that.

One shot of CheeriMac.

Cover art by Luuandherdraws. Now with a live reading! Link

On the last day of school before summer vacation, Cheerilee informs her students that she's going to pursue her doctorate in Fillydelphia, and won't be returning as their teacher in the fall. Her friends and students alike spend her last night in Ponyville bidding farewell and showing their appreciation for her, each in their own unique way.

But one student, in particular, has a hard time coping.

Originally written for the Writeoff Association's July 2016 prompt* and published under the title Bonitatem Doce Me, this story has been revised, rewritten, and expanded from its previous version. Featured on EqD on 8/9/16. Also featured in the Royale Canteloupe Liberty.

*which it won!

It's the end of the week and Cheerilee is enjoying a drink at the bar. Her mellow mood is soon disrupted. The seat next to her is taken by none other than Princess Luna, who has her own drama to unload on anypony who will listen. Or understand her...

Rated Teen for drinking and adult situations
Cover art by me.

Reading by McClain Media.
Featured in an article on Equestria Daily on 12/21/2022.