A Guest Chapter written by Jondor
Cheerilee looked over the crowd from behind her mask. In a corner of the hall, the quartet began to play a waltz and masked ponies from all across the room began flocking to the dance floor. Cheerilee’s eyes drifted over the few scattered stragglers, mare and stallion alike, still lingering in the wings.
She sipped her wine, wondering if the night had been worth it. After a day at the spa and much lamenting over her horrid love life, Rarity had insisted on obtaining an invitation for her. Fresh faces at a masquerade ball in Manehatten had seemed like a good idea at the time, but Cheerilee was doubting the wisdom after nearly two hours and no luck.
Fresh faces weren’t much use when everypony was masked, and rich Manehattenites weren’t good company unless you liked snobby snootiness. Cheerilee sighed and set down her nearly empty wine glass, intent on leaving.
She heard a crack of breaking glass and swore loudly as the stem of her glass broke, splashing the last of her drink over her foreleg. Several ponies turned to sneer at her outburst, but one in particular caught her eye.
Her blue eyes twinkled behind her mask and her bright pink ponytail bounced against her withers as she trotted closer. Her dress was provocative rather than elegant, and was barely long enough to cover her cutie mark, showing off her hind legs and her long, pink tail. This was no snooty Manehattenite.
Cheerilee quickly wiped away the wine and did a little fast primping of her mane and dress. Rarity had insisted on not only lending her the outfit for the evening, but also took time to style her mane into large, elegant curls that emphasized the lighter whitish shades in order to match the dress. Cheerilee barely recognized her own reflection.
“Hey, there.” The pink-maned mare slid smoothly into the opposite chair at Cheerilee’s table. “I’m guessing you’re not from around here.”
Cheerilee blinked, still temporarily dumbstruck, and then smiled. “What gave me away?” She asked, winking and giving her curls a playful bounce.
“Little things. Your lack of unnecessarily expensive jewelry. Your colorful choice of words. The fact that you didn’t even bat an eye when another mare came over and started hitting on you.” One blue eye winked at her from behind that intricate mask.
Cheerilee giggled. “It’s true. Any other mare in here would be utterly scandalized.” Somewhere in the back of her mind, Cheerilee couldn’t shake the feeling that this mare’s voice sounded familiar, but she was quite mesmerized and disarmed by her simple, but highly charismatic charm.
“Since I’m not supposed to ask where you’re from, how about I ask you for a dance instead?” The mare extended a tan hoof across the table and fluttered her lashes behind her mask as an up tempo song began to be played. “Unless that would be too scandalous.”
Cheerilee hesitated a moment at the mention of the masquerade’s rules. It was a shame and just her luck that she wasn’t supposed to ask any personal questions or even properly see this charming mare’s face, but she grinned and winked anyway, taking her proffered hoof and standing.
The two mares joined the other couples on the dance floor and took each other’s hooves, dancing together in defiance of the stares and gasps of the other guests. Song after song they danced with each other, holding each other closer and closer as the night wore on. They completely ignored all of the sidelong glances they continued to receive from the glowering Manehattenites.
Some time later, the two mares ended up alone on the patio, gazing up at the night sky as they stood pressed close together and gently nuzzling against each other.
“To think I was about to leave before you came over. I would have missed out on such a wonderful night. Thank you.” Cheerilee sighed happily.
“No. Thank you,” the mare replied, raising a hoof to wrap around Cheerilee’s withers. “You were a much better dancer than any of those starch-collared stallions.” She ran a hoof along the edge of Cheerilee’s curls, drawing her attention. “And much better looking.”
Cheerilee held her breath and parted her lips just a touch as the other mare leaned in slowly, giving her time to refuse. She accepted the kiss gratefully and gave as good as she got.
Long moments later they finally broke apart. As they pulled back, their masks caught against one another and pulled away from their faces just a touch before coming free and snapping back. Both mares rubbed their noses, giggling and blushing.
Returning her hoof to the ground, Cheerilee sighed audibly. Her lips suddenly curled into a frown. “The night is almost over and it’s just my luck that the one time I meet a wonderful partner, it’s at a masquerade with silly rules that keep me from ever seeing her again.”
“I don’t see why not,” her partner countered. “I doubt they’re going to invite either of us back after tonight.”
Cheerilee’s eyes widened for a moment, considering the possibility. Then she nodded and both mares removed their masks.
As she focused on and recognized her dance partner, her eyes widened in surprise.
“Mayor Mare?”
Cheerilee’s eyes roamed over the young mare before her. Without her glasses and her mane dyed prematurely grey, she looked much more like a filly just out of college than the venerable, middle-aged statesmare she appeared as in town.
The mayor, however, looked on in shocked horror, eyes bugged out and mouth agape.
“Cheerilee?!” Her voice was shrill and piercing. “Nononono, this can’t be happening!”
“What’s wrong, Ms. Mayor?” Cheerilee chided herself internally for slipping into her public servant mode when the mayor was obviously trying to avoid her public persona tonight.
“What’s wrong?!” she shrieked, hyperventilating. “Can you imagine the scandal?! Everypony will be up in arms! The Ponyville Express will run slanderous stories for a month or more!”
“I’m sure it can’t be that bad. After all the disasters and invasions we’ve survived, nopony is going to bat an eye at the mayor dating the schoolteacher.” Cheerilee reassured, reaching out a hoof to pat her shoulder.
The mayor took no notice of her words, continuing to rant. “They’ll think it’s some sort of tax scam! I’ll be audited, blacklisted, condemned, and deposed! I’ll have to move to Las Pegasus, get cutie mark alteration surgery, and hope to live it down!”
Mayor Mare stopped suddenly, her eyes coming to rest on the gentle hoof stroking her shoulder. She froze for a moment, then let out a scream of terror, vaulted over the patio railing, and bolted into the night.
Cheerilee wondered and puzzled at the mayor’s behavior, not even moving until a stallion poked his head out of the door and spoke. “Madam, I heard shouting, are you alright?”
“Just wonderful.” Cheerilee replied through gritted teeth, turning to walk back inside.
“You aren’t supposed to take off your mask!” he exclaimed, catching sight of her bare face. “Nopony is to know your identity, that is the whole point.”
“Don’t remind me,” Cheerilee growled as she stomped past him, back to the bar.
Damn you Mare, that could have been perfect.
Do you think Mayor Mare knew ahead of time that Cheerilee was cursed? Because that's the vibe I'm getting.
It went wonderfully until they took off their masks.
Maybe it's Cherilee's face.
A date for each chapter? Like, legit 1000 chapters? Count me in!
I hope this fanfic goes on until the world ends or something.
3814236 Well, I'm not sure I'll actually get to 1,000 but I'm going to keep going until everyone can't stand me anymore.
3814244 You WILL get 2 a thousand becuz i'll never tire of these
Pfffttttt.
Welp... Almost, Cheerilee, almost.
~Skeeter The Lurker
You know, the funny thing is, there's one fanfic where Mayor Mare is Cheerilee's mother. So imagine if that was the case for this chapter.
3814482 It'd be chapter 10 all over again! The horror!
And thus, the (mis)adventure continues!
Mayor Mare and Cheerilee both deserve a special somepony. Darn the Mayor's concern for politics over feelings. Sometimes the heart wants what the heart wants. Besides, it's not like there's been an election in Ponyville in over four years. Darn it to heck.
fc02.deviantart.net/fs71/f/2014/013/3/6/schmoopie_by_comeha-d7213zs.png
3814665 Can ponies flip the bird? What is the hoof equivalent?
3814702
When extra avatistic digits appear on a horse, they show up as small digits on one to the other side of the large main one.
Therefore a regular horse's hoof is the middle one by default.
They can't do anything but flip the bird.
3814838 Rarity is going to be mortified when she finds out how rude she's been all this time!
3814199
3814693
Mayor Mare is just a tad too concerned about her public image what with the new princess in town whom she fears might be called up to replace her at the drop of a hat.
3814446
Maybe if they'd gone out for a game of horseshoes 'almost' would have cut it.
3815074
Or used a grenade. Seemed like the party could have used it.
~Skeeter The Lurker
3815091
A grenade would definitely have livened things up... for a moment at least.
3815097
A quick, suspenseful moment.
~Skeeter The Lurker
3814702
Probably this:
static3.wikia.nocookie.net/__cb20130217131748/mlp/images/e/e1/Sassaflash_shakes_hoof_at_Caramel_S03E13.png
3815097
3815105 They just need one of the Party G.R.E.N.A.D.E.s from WoW.
3815132 No wonder Caramel looks so irritated. Or maybe this is after his latest date with Cheerilee…
Sea Swirl's the one who should be pissed. He's blocking her shot!
3815132
3815153
Or this:
gyazo.com/16bcaae6d7a4deeb1e2c91d5b17fefff.png
3815133
That'd probably be the better grenade. Or the Holy Hand Grenade.
~Skeeter The Lurker
3815179 Well, that works for pegasi, and I suppose unicorns could use magic to flip you the bird.
Earth ponies… hmmmm. Well, both Pinkie and Applejack seem to have prehensile tails. I'm sure they could manage some rude gesture with them.
That is, if you could get Pinkie to even consider a rude gesture...
3815199
Do like in Mr. Bean. Make her think it was a new way to say "hi".
~Skeeter The Lurker
Phew. I thought for a sec it was going to the Cheerilee's mom or something. The Mayor needs to chill. Nothing wrong with a marefriend. Heck, if you're a politician it's normal to have multiple partners.
Fun fact: Mayor Mare's ranting includes three interrobangs. Best. Punctuation. Ever.
3815473 THIS IS TRUTH, PEOPLE! All punctuation bows before the mighty interrobang!
3815217 There's not a lot to get. Cheerilee had a terrible date and then was harassed by an jerkwad cop who was trying to find something illegal to pin on them.
3814244
My bet is by chapter 506 we might start to get tired, if the quality stays at this level.
Don't fret on it, Cherilee. If the shallow foal isn't willing to take the risk for you, then she isn't worth your time.
Just tell everypony about how she hit on you but backed out when she realised you were from Ponyville anyway. It will ruin her reputation and make everypony look on her as a tease too!
3815825 I got the comment section version of rotten vegetables thrown at me for that shipping tease.
3815868 i'll do my best, though I fear to speculate what the stories will be like by that time. We'll have reached some extreme weirdness at that point.
3816157 Hey! Union regulations are union regulations! They did offer to demolish the ride for them...
3818886 It's my pleasure to ruin Cheerilee's life for your entertainment.
Are you seriously going to write a thousand chapters for each date?
3819120 I'm going to write until I, or everyone else, gets sick of it, so maybe...
It all really depends on if people still like it or not.
These are great but truthfully sad stories.....she reminds me of my younger life and the opposite sex. (Ugh, what luck!) I sure hope Cheerilies' gets better soon!
3819524 That's the thing about this story. They are funny now, but I'm thinking about how readers will feel on Cheerilee's sixtieth date. It might turn from funny to cruel at that point. We'll see, I guess.
It's Las Pegasus, not Los Pegasus.
3820018 I did that on purpose, actually. I got yelled at once for writing Bon Bon instead of Bonbon. However, I just went to the wiki, and Sweetie Drops is listed as Bon Bon, so I think I'll change it. I prefer it with the space.
3820039 Fixed! Thanks.
3820199
That's kinda how I felt about it...
3820199
3820207
i was being facetious
3820277 Oops. Sarcasm detection fails again. My bad.
Will this story really have a thousand chapters?
3820558 I have my doubts as to a thousand chapters, but I'm going to continue write it until either I'm tired of it, or everyone else is.
Or Cheerilee comes to kick my teeth in...
3820569 If it's Lunaverse Cheerilee, you'll be lucky if all she does is kick your teeth in.
I feel really bad for Parallax, and Caramel. I mean, both of those sounded like alright dates.
Everypony else was a right Bastard though. No sympathy at all.
You should totally hook Cheerilee up with Spike next. Only he keep insisting that Cheerilee dress like Rarity, or something equally creepy.
3822903 Of course there is a trope about sinister ducks.
Friggin' tropes breed like rabbits!
Pink mare, blue eyes... Oh god its Pinkie, isn't it.
Okay, tan hoof so I guess not.
Bwhahahahaha!