This story is a sequel to On Wings
Following a crazy week where her entire being was turned upside down, Cheerilee is perfectly happy as both an earth pony and as the one mare faculty of Ponyville Elementary. Now that the school year is through, she makes her annual plans to volunteer in the town's summer school program, even if it means having to possibly deal with the clique of three unicorns who fancy themselves her professional betters and belittle her constantly. But this is nothing new, nothing she can't handle.
However, when Mayor Mare pulls Cheerilee aside and informs her about Rainbow Dash having lost the ability to fly due to an on-the-job incident, it becomes clear that this is not going to be another routine summer. Forced into being Dash's last hope of ever flying again, Cheerilee is going to need all the help she can get to take education to new heights in Ponyville. The only recourse she has is to regain her wings and hope that she can pass this challenge with flying colors...if she doesn't just crash and burn in the process.
Rated Teen for swearing, minor sexual humor, and Cheerilee's love of alcohol.
You get an automatic thumb up for the title reference.
You were the one lauding your talent of being a quick study, Cheers. Time to prove it. Help her, Cheerilee, you are her only hope.
Yes, I loved the first story and can't wait for it to be continued here
Cover art by Shinzakura?
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No, actually, most of that is done by me. The only things Shinzakura originally made was the upper right portrait and middle bottom - recolors of the "Medallions" he made for Minty and Champagne Dreams, respectively, and used with his permission. Everything else was made entirely by me from reworked vectors, but the "portrait frame" style overall is from scratch.
Glad to see a sequel to Winged, it was a fascinating character piece into the experience of families of different tribes. I also like the worldbuilding of the elementary schools, Ponyville is pretty large to have a one-room school house with 12 kids teaching all the children in town. I'm always a fan of Mayor Mare as the aunt of Pinkie as well.
One thing I never brought up on the last story that seems like it will be relevant here as well: What's up with the racism from unicorns towards earth ponies in education? Despite being the smartest pony ever no unicorns will hire Cheerilee to be a teacher anywhere nice, even in areas that have nothing to do with magic. In your story do unicorns control the educational establishment somehow, or are most unicorns (who don't have earth pony siblings) just generally racist towards earth ponies, and personally offended that an earth pony would get good scholarships and become a valedictorian? I would guess it's because she's looked for nicer jobs in Canterlot, which is predominantly a unicorn city, but it seemed like this rule that unicorns got all the best teaching jobs applied everywhere, so Cheerilee couldn't just get a fancy teaching job in Manehatten.
Oh, and I have to ask, is Breakfast Club supposed to be a ponified Molly Ringwald? Because if so that is awesome!
Whatever Cheerilee's second wing is, way to f
king go, Twi. 
Waiting for more!
Oooooh shit, Twilight dun goofed.
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*Desk slam*. In this latest testimony, you stated that Dusty and Silver had met Princess Twilight before. However, this completely contradicts your earlier statement!
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I ask the court, how is this possible?!
Other than that little gaf, I'm interested to see what happens next!
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Good catch, fixing.
EDIT: I just removed Twilight's line outright to fix the problem.
Cheerilee is prepared.
And please don't tell me Twilight turned her into a draconequus...
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Discord - Of course I can fix Rainbow Crash it'll be a snap... well hubba hubba who is this lovely vision of chaoticness?
Are all the chapter titles going to be plays on songs from the Top Gun soundtrack?
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Mayyyyyyyyyyybbbbbbbbbeeeeeee...
Your snarkey Cheerilee makes me very happy. Sometimes you can just tell she's holding back when we see her in the show.
I can't help but wonder: is Discord donning Italian attire for making his exit a reference to John De Lancie's role as evil time-traveling Leonardo DaVinci in NTSF:SD:SUV? Probably not, but the coincidence is amusing
Please... Please don't let that trio of teachers meet DT and Spoony. They don't need examples of the kind of adults they can legitimately and successfully mature into...
Oh? Is that someone knocking on the fourth wall I hear? Quite a subtle knock that can easily be dismissed as not knocking at all. Very fitting for Fluttershy.
Greatly enjoyed this chapter. It seems that Ruby Minotaur's older brother really gives a pony wings.
Not sure that's really a knock at all, greycalt.
Another great chapter, I loved the teasing of Big Mac by Rarity and Applejack.
Again, I do hope you address the underlying reasons unicorns in the education system seem to be prejudiced against earth ponies, I feel like it will help fit the story together, especially if Cheerilee starts looking for a job in Canterlot.
That's a shame because I think Spike probably has a few plans for Rarity's plumbing.
...Well, Rarity, I see your ability with projections has improved vastly.
I wonder what's up with Cheeri and cider.
So, Cider makes Cheerilee think she can fly? As in, even when she doesn't actually have wings? Interesting...
So, what show were you watching in November?
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So...what story are you reading again? You know, the alternate universe one where she got wings magically....
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I'm well aware that Discord has given Cheerilee wings twice now. I was making some inferences from Cheerilee's thoughts and actions last chapter and her and her brother's conversation this chapter that Cheerilee may have, in times past, attempted to take flight without having wings when she got hammered on cider. Between those things and the fact that she has pegasus heritage makes my idea not-too-unreasonable.
I respect you as a writer, but please give me a little credit before jumping to conclusions.
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Easy, that was meant as a joke.
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Alas, the woes of conversing solely through text...
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Unfortunately they haven't perfected the art of interpretive dance via Fimfiction yet.
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Think you missed a closing quotation there. Other than that, I didn't see any glaring errors. Good chapter.
5650558 Yes, Rarity is certainly projecting a lot in this chapter.
Oh, hi there AAG reference!
Childish pranks are childish.
That said, I'm glad to see Cheerilee's parents again. It's amazing how useful parents are for setting one's head right, whether in reality or in a story.
I really hope this goes well but Mac's timing is bad, you don't ask a mare out while her mum and dad are present that's just asking for the Inquisition.
The CheeriMac here is just so adorable! Somehow I'm hoping the sabotage plans backfire to make the date better for them, like in The Lion King 1 1/2.
It's great seeing your Rarity do things like give the advice to be themselves, too. There are reasons she's 2nd best pony in my mind.
Damn straight. You keep that little creep away from your plumbing, Rarity.
Sir Grand Macintosh, of the largest Apple Estate in Equestria.
You've managed to make me dislike those teachers even more than I already did. Well done. (I really hope Diamond Tiara never finds out about them...)
Poor Cheerilee.
I hope Big Mac can catch up with her before she gets incredibly anti-drunk.
You have created a masterpiece!
PD needs to suffer, really suffer, how can he do that to such a sweet couple?
We need Big Mac and Pinkie to turn up with a music system to serenade Cheerilee, she seemed rather impressed at the Pony Tone's concert even if that was Fluttershy.
Pft, that's all he did to ruin the date? Make the silverware slippery?
Granted, it snowballed hilariously, but that wasn't even his intention. AND he didn't get away with such an innocuous plan, either.
D for planning, C+ for execution.
I'd grade his exit strategy too, but I have to be fair; there's no way he could have measured up to Pinkie's reality-violating powers.
Slowly working my way through the backlog of updates on my time off. One thing to watch out for:
You have a few moments where the paragraph splits like this one. Also, the bolded you should be your. Other than that, things are getting interesting. Looking forward to Cheerilee and Mac's date. That should be an interesting night, though something tells me they won't be going back to that restaurant afterwards
Good chapter. Whatever's going on with Rainbow being unable to say that word is interesting; either this is an effect of her accident, or she's been brainwashed by the [LA LI LU LE LO]. And I wonder what Applejack would think about her brother speaking fancy.
Oh? More reasons to strongly dislike Breakfast Club and her pals? I'll just add it to the pile.
Big Mac, on the other hand? I love your version of him. And that moment in the kitchen was pretty priceless too.
Why does this make so much sense?
5791534 This has been my headcanon for years.
Wait, I'm confused: The maitre de deliberately over-polished the silverware, and gave Cheerilee a pair that's meant to be used only for unicorns. That's nasty, but why are they talking about bringing in the guard? The only actual crime committed was when Big Mac punched that dude. Is Perfect Demeanor not knowledgable of the law, or does he think that friends of Twilight Sparkle will be held above it?
The speech between Big Mac and Cheerilee was really sweet, by the way.
Argh! Curse you, Mayor May Mare, and your unconscionable interruption of cliché kiss scenes!
Love how you write Big Mac and Cheerilee's dad. And now you've given me the headcanon that different users of unicorn-style magic have different, shall we say, dietary needs.
Regarding Twilight: Grease for the Grease God! Books for the Book Throne!
I wouldn't feel reassured by that. Big Mac's a freaking mountain. He probably needs to drink manticore venom just to get a good buzz going.
And Twimac has been out of style for like, two seasons anyway.
So he says at the end of his big, chatty, extremely eloquent "you're awesome and you just don't realize it" speech.
How the blazing hay did the antagonist ponies convince the council to council to set up a (presumably mandatory) three versus one competition that has absolutely nothing to do with their curriculums while Cheerilee is in the middle of sensitive and super-important therapy classes?
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Because those are the only things we ever really see the princesses eating.
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The guard is, as far as I can tell, the closest thing to a provisional police force that exists in canon.
And thanks!
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Well, after Rarity chugged down enough ice cream to quantify an entire aisle from my local grocery store (she's still a horse so just ONE of those containers was probably equal to several gallons to a human), you gotta wonder how she retained her figure...
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A cockatrice one used its Medusa Stare on Big Mac. After three days of agonizing pain, the cockatrice died.
And as for the council, you gotta remember these are the same idiots who thought that making Cheerilee go through changing pony subspecies again all to help Rainbow fly again - despite the fact Cheerilee knew jack squat about flying and doesn't even fully qualify for being a physical therapist - was a good idea. That, and one of the unicorn teacher trio is married to a pony who is on the council so they have a bit of additional influence there.
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Okay, I get that the council is being strung along by the three bad pones, but the "three-on-one" aspect kind of threw me for a loop (unless I misinterpreted that part). A team competing against a lone individual would be bizarre under ANY circumstances, but the fact that the plot has to have a veneer of legitimacy makes it extra weird. They're hardly even trying to disguise their harassment at this point.