My Fair Mare

by FlutterPie10

Rating: everyone
Tags: Cheerilee, Big Macintosh, Slice of Life, My Little Pony: Friendship is Magic, Comedy
Length: 2021

Cheerilee was in the 'Sisterhooves Social' when Apple Bloom and Big Mac (dressed as Orchard Blossom) competed.

Cheerilee was in the 'Sisterhooves Social' during the events of 'Brotherhooves Social'. What's gonna happen if she finds out about 'a certain red mare'? Let's find out!

Published 2015-11-15 09:00:01 UTC
Last updated 2015-11-15 09:00:01 UTC

My Fair Mare

Cheerilee's POV

I was in the Sisterhooves Social just to see some of my students competing with their sisters. I always liked this kind of events, it teaches teamwork and sport spirit. I was sitting among the crowd, watching the event and, oddly enough, I saw Sweetie Bell.

"Hi, Ms. Cheerilee!" Sweetie Bell greeted.

"Hi, Sweetie Bell" Cheerilee greeted "What are you doing here? Aren't you suppose to participate in the Social with Rarity?"

"Sigh...she's with Applejack in Manehattan" Sweetie Bell answered with a sad tone.

"Oh, I'm sorry, Sweetie Bell" Cheerilee said.

"It's okay, I can always participate next year" Sweetie Bell said "But I'm happy to see my friends Apple Bloom and Scootaloo to participate!"

"Wait, didn't you say Applejack is gone to Manehattan too?" Cheerilee asked "Also, Scootaloo doesn't have a sister...does she?"

"Well, Rainbow Dash will pose as Scootalo's sister and Apple Bloom...well, she brought her long-lost...COUSIN!" Sweetie Bell explained "Her name is Orchard Blossom"

Orchard Blossom? Hmm...that's not a usual name for the Apple family. But anyway, the event was about to start and that's where I saw Scootaloo with Rainbow Dash and Apple Bloom with her cousin Orchard Blossom: red coat, blonde mane, she was wearing a white blouse with a pink scarf, a sky-blue skirt with blue apple prints, pink bloomers, dress shoes and a lot of make-up. I'll be honest, she's the weirdest looking mare I've ever seen. In fact, she looks extremely familiar.

The first part of the event was singing the Social's official song. I gotta admit, Apple Bloom and Orchard Blossom were singing very beautiful. But when Orchard Blossom sang the last note, her voice suddenly sounded...deep. Hearing that voice reminded me of certain stallion's voice...could it be? Nah, maybe it's just my imagination.

As the event went on, Apple Bloom and Orchard Bloom were failing in every challenge, mostly because of Orchard Bloom's un-mare attitude. Whoa, I wonder if her parents wanted a colt. Anyway, the face off final challenge: the obstacle race. Scootaloo and Rainbow Dash were very determinate to win. But as the race started, Orchard Blossom was even more determinate to win that she basically destroyed every obstacle in the most brutish way possible. Sweet Celestia. And that wasn't all, but she was also losing clothing in the process, even revealing her Cutie Mark that looks extremely familiar. Could it be...? No, that's not possible. They eventually won the race and then...it happened...her clothes were completely torn apart (even her blonde mane was actually a WIG!)...Orchard Blossom...WAS BIG MAC!

But believe it or not, that wasn't the most shocking part, the most shocking part was that EVERY PONY KNEW HE WAS CROSSDRESSING! Every pony, except ME! And maybe an old pony judge who was a little dreamy for him, but I didn't know it was him despite my suspicion! But the judges told them that they would let him compete since the definition of being sisters can apply to anyone who has a strong connection to a little filly. Unfortunately, they got disqualified for destroying the obstacles in the final challenge and as a result: Scootaloo and Rainbow Dash won the event, so good for them. Sadly, Apple Bloom seemed very upset to Big Mac before they were gone home. I'm not gonna lie, today was one of the weirdest days of my life and weirder things happened in Ponyville. But I guess I can't blame Big Mac for that. He thought the Sisterhooves Social was a mares-only event and Apple Bloom wanted to participate. I thought the intention was very sweet, but Sweet Celestia that was very awkward.

I felt kinda bad for him that he destroyed his own disguised after finishing the race. So, while everybody was leaving, I recovered every piece of clothing of 'Orchard Blossom', I got a really cool idea.

Big Mac's POV

After Granny Smith called us by sayin' Applejack came back from Manehattan. Apple Bloom and Ah went back home to see her, we had A LOT to tell her what we did today. During dinner, after she tol' us about her Cutie Mark mission with Rarity, we tol' her about our participation in da' Sisterhooves Social'. Her reaction was exactly what we expected.

"HE DID WHAAAAAAAAT?!" Applejack asked, extremely shocked.

"He thought da' Social was fo' mares only, so he puts on some mare clothing to participate" Granny Smith explained.

"At first it was very awkward for me since he was wearin' mares clothing, but as we sang together, Ah felt very confident!" Apple Bloom said.

"And...didn't da judges suspected you were a...ahem...stallion?" Applejack asked.

"Nope" Big Mac answered.

"Well, we thought they were buying the whole thing" Apple Bloom answered "Until we got busted and disqualified. But it wasn't because he was no mare, it was because we...kinda...destroyed some...things...in the final race"

"So Scootaloo and Rainbow Dash won the event?" Applejack asked.

"Yes, they did..." Apple Bloom answered with a sad tone.

"Oh, don't put dat face sugar cube, Ah promise Ah'll participate with you next year" Applejack said.

"Really?" Apple Bloom asked, despite she knew about that.

"Sister promise!" Applejack said as she hugged her. But then she turned her face to Big Mac "And YOU, MISTER!"

Big Mac got very nervous, thinking Applejack is gonna yelled at him. But instead...he got a hug from her.

"Thank you for takin' my place in the Social" Applejack said "You are the best brother any filly could have"

That comment made me tear some salt water out of my eye. Applejack couldn't lie to me. After all, her element is Honesty.

"But next time, be sure about the rules before you try to do somethin' crazy" Applejack said "Do you promise?"

"Eeyup!" Big Mac answered.

Cheerilee's POV

The following morning; I found out Rarity came back from Manehattan. I went to her house and I brought the pieces of clothing with me.

"Hi, Rarity" Cheerilee greeted.

"Oh, welcome Ms. Cheerilee" Rarity greeted "What can I do for you?"

"Well, you see, I brought this shredded clothing" Cheerilee said, taking out the shredded clothing out of the bag.

"OH DEAR!" Rarity screamed of horror "What on Celestia's Heavens happened?"

"I'd like not going on details, but I was wondering if..."

"Don't worry, I can fix this!" Rarity said "I don't care if it takes forever!"

"Actually, this outfit is too big for me, I was wondering if you could do the same outfit, but with my measures" Cheerilee said.

"Oh, absolutely, dear!" Rarity exclaimed.

So Rarity took my measures, so she can recreate the outfit for my size. Where am I going with all this? You'll see soon...

Big Mac's POV

A few days passed since da Sisterhooves Social and nobody who went there remembered the...reveal. One day, Ah went to da market in Ponyville to buy da groceries. Everything seemed normal until...Ah saw her, Cheerilee, Apple Bloom's teacher and da mare dat Apple Boom and her friends set up a date with me. Just to be clear: we're not datin' or anythin'...but Ah admit she's very pretty and kind.

She looked different today, she was actually wearin' clothes, which it's unusual in Ponyville, even for mares. She was wearin' a blouse with a scarf, a skirt, bloomers and dress shoes...wait a minute, THAT'S THE SAME OUTFIT I WORE AS ORCHARD BLOSSOM! I don't know where did she get them or how she was able to fit them perfectly since I'm obviously bigger than her. I tried to avoid her, but...

"Hey, Big Mac!" Cheerilee greeted as Big Mac stood very nervous "Are you buying groceries in the market?"

"Uh...eeyup" Big Mac answered, nervously.

"What do you think of the outfit I'm wearing?" Cheerilee asked, doing a twirl "Do you think I look nice?"

"Eeyup...!" Big Mac answered, getting more nervous.

"Thank you, I actually asked Rarity to make the exact same outfit that certain mare wore in the Sisterhooves Social" Cheerilee said as she went closer to Big Mac "What was her name again? Orange...Blossom, perhaps?"

Ah was busted! She knew Ah was Orchard Blossom! She was gonna laugh at me in front of all da ponies in da market! So, what did Ah do? Ah ran away as fast as possible.

Big Ma ran away from Cheerilee.

"Big Mac, come back!" Cheerilee exclaimed as she followed him.

The chase continued until Big Mac went to an alley and without looking at it, he crashed against a wall. He passed out unconscious.

...

Big Mac slowly woke up and the first thing he saw was Cheerilee.

"Are you okay, Big Mac?" Cheerilee asked.

"Eeyup..." Big Mac answered.

"Sorry if I scared you out" Cheerilee said "I'm just gonna say it: I was there in the Sisterhooves Social. I was there when Orchard Blossom's outfit was torn apart and...well, you already know. Listen, I know why you did that. Your little sister wanted to participate and you took Applejack's place since you thought this event was for mares only"

"Sigh...eeyup" Big Mac said, very ashamed.

"Look, when it's about helping your family, there's nothing to be ashamed of" Cheerilee said "Apple Bloom is very lucky to have a big brother like you. Anyway, again, sorry for scaring you out. I better go..."

Cheerilee was about to leave. Ah admit at first Ah dressed up as a mare to be in da Social...but there's somethin' else and it was something my family don't know about...yet.

"Cheerilee!" Big Mac called as Cheerilee turned around "It's true dat Ah did what Ah did to make Apple Bloom happy. You see, she always looked at Applejack as her heroine and...Ah admit Ah was a little jealous. Ah wanted Apple Bloom to look at me as a hero and when Ah found out Applejack was unable to participate in da Social, Ah thought it was da perfect chance to make Apple Bloom see me as a role model. At first Ah ended up goofin' up da entire Social, but at da end, Apple Bloom told me how a great brother Ah am. Ah was...very happy for dat"

"It is the most beautiful thing I've ever heard" Cheerilee said.

"But wait, there's more" Big Mac said "When Ah was Orchard Blossom, when Ah was wearin' mare's clothes, Ah found myself very confident. Ah felt strong, Ah felt that Ah could conquer EVERYTHING! Ah was feeling...brave"

"So...do you wanna be a mare?" Cheerilee asked, raising an eyebrow.

"What? No!" Big Mac answered.

"Are you sure?" Cheerilee asked "Because I can completely understand"

"No, Ah'm proud to be a stallion" Big Mac said "But...sometimes, despite how strong Ah am, Ah'm kinda shy. But as a mare, Ah could express myself, feelin' a lot more confident. Even Ah had a dream dat Ah was an Alicorn princess..." then he saw Cheerilee with a very confused face "Ah think Ah said too much...good-bye, Cheerilee"

"Wait, Big Mac!" Cheerilee called "It's okay if you like wearing mare's clothing. In fact, they're just clothes! I know they're made for a specific gender, but who gives a flying feather? If you wanna wear pink bloomers, then wear pink bloomers! Any piece of clothing you find comfortable!"

"Wow, Cheerilee, Ah never thought you could be so open-minded" Big Mac said.

"Hey, I'm a teacher, I have to be open-minded to help my students" Cheerilee said "Hey, I just got an idea: how about if we go shopping together?"

"Uh...you and me?" Big Mac asked, nervous.

"Well, I was talking to Orchard Blossom" Cheerilee said "What would she say?"

"She'd say she would LOVE going shopping with such a lovely mare!" Big Mac said with his Orchard Blossom voice "Especially during such a beautiful sunny day in Ponyville!"

"Hehehehehe!" Cheerilee giggled "I think this is the start of a beautiful friendship"

They both walked together as they laughed.

End of the story

Author's Note

(A/E: I hope you liked my one-short story. In case you wonder the bad grammar in the Apple family's dialogue, that was intentional to imagine their Southern accents easily. Sorry if they annoyed you.)