• Published 15th Nov 2013
  • 8,725 Views, 2,787 Comments

Cheerilee's Thousand - xjuggernaughtx



Cheerilee goes on one thousand terrible dates.

  • ...
19
 2,787
 8,725

PreviousChapters Next
Date Nineteen - An Affair to Forget (Guest Chapter by Jondor)

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.

PreviousChapters Next