• Published 15th Nov 2013
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Cheerilee's Thousand - xjuggernaughtx



Cheerilee goes on one thousand terrible dates.

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Date Seven - The Will to Succeed

“So, you’re Ponyville’s teacher, then?” Dusty said, spearing a potato with his fork. “You must really enjoy foals, huh?”

“Oh, my, yes!” Cheerilee answered, breaking another piece of the restaurant’s delicious bread off from the loaf the waiter had left at the table. “Each one's so full of potential! It’s almost like a puzzle, you know? You have to examine each one to find out just what makes them tick and use that to help them grow.”

“I just find that so admirable,” Dusty said, dabbing at the corner of his mouth with his napkin. “Ponies today are so caught up what they’re doing that they never take the time to help the next generation.”

Cheerilee beamed. Oh, he’s so caring! she thought as she chewed on her delicately sautéed wheat stalks. She’d been worried when he’d asked her out, since her love life had been so… turbulent, but the night had been wonderful. Keep it up, buddy! she thought. You’ve just about got date two on lockdown.

Dusty signaled to the waiter. “Would you mind bringing us another bottle of this wine? It’s excellent.”

“Of course, sir,” the waiter answered, trotting briskly off.

“So, what brings you to Ponyville?” Cheerilee said, swirling her glass before tipping it back and draining in the last of the marelot. “I don’t believe I’ve seen you here before?”

“I’m looking for work,” the stallion said, shrugging ruefully. “I’ve been living off of savings for the last eight months, but I’m starting to get desperate. I can’t find—”

STOP RIGHT THERE!” a voice thundered, causing Cheerilee and Dusty to jump in unison. “You’ve shot yourself in the hoof, and only Iron Will can save your chances for a night of love!

“What?!” Cheerilee said, her hoof pressed firmly against her chest to still the rapid beating of her heart.

“What are you doing here?” Dusty hissed, glaring at the minotaur.

“Saving you,” Iron Will returned, thrusting his enormous face directly into Dusty’s, “from future nights of celibacy! As agreed, I’m here to coach you! To mold you into…” Iron Will placed his hands on his hips, thrusting his pelvis forward in rapid succession. “… an irresistible stud! Your bits paid for the secrets to get laid, and I promise to deliver!”

What is going on here?” Cheerilee said icily, burning a hole into Dusty with her eyes.

“I… heh-heh… I have no idea!” Dusty replied, sweating profusely and scratching his mane.

“Rule one!” Iron Will thundered, drawing the attention of the few restaurant patrons that hadn’t yet stopped eating. “You won’t get flank with an empty bank! Never admit that you are unemployed!” Iron will leaned over the table, tapping the furiously blushing stallion in the chest. “You were doing well. You were a polite, pleasant, conversation machine, but your poor decision sent this date into a tailspin!” Iron Will spun suddenly, looming over Cheerilee. “I could see it! This mare was about to send you trotting to the doghouse!”

“Would you get—” Dusty yelled to the minotaur, before turning to Cheerilee. “I don’t know what—”

“Paid for the secrets to get laid?” Cheerilee said frostily as she crossed her legs over her chest.

“That’s right!” Iron Will shouted. “This stallion’s on a two year dry spell, and desperate times call for expert advice! Iron Will’s course on seduction is money well spent. A bankable program that has mares putting their socks on for stallions all over Equestria!” Jumping on the table, Iron Will pointed to Dusty, who had slumped so far down into his seat that his eyes were barely visible above the tabletop. “Down to his last bits, this stallion had the sense to spend them wisely. Iron Will guarantees results!”

“Oh, I don’t think this one will be getting the ‘results’ he was looking for!” Cheerilee spat, tossing her napkin down on the table before hopping out of her seat. “I think you’re going to have to give his bits back!” Cheerilee shot a withering glance Dusty’s way and he shrank down in his seat another inch.

“This is all your fault!” Dusty growled at the minotaur. “She was warming up. I almost had her!”

“How dare—” Cheerilee began, snarling.

“My course guarantees nothing less than third base within three mares,” Iron Will shouted, plucking the stallion from his seat and holding him several feet above the floor, “and you struck out! We’re moving on to your next at bat!”

“You were supposed to review this stuff with me after the date!” Dusty cried, kicking his hooves futilely over the restaurant’s hardwood floor.

“Time is bits,” Iron Will shouted. “You didn’t know it yet, but the date was over the minute you said you were an unemployed lowlife! If the mare’s turned cold, it’s time to fold!” Iron Will pivoted on his hoof, thrusting Dusty at the fuming teacher. “Is this the kind of stallion you’d give the time of day to?” he asked.

“Now that you mention it? No,” she replied, scooping her saddlebags from beneath the table.

“No, this isn’t what it looks like!” Dusty said, wiggling.

Cheerilee answered with a half-lidded stare.

“Well, okay,” the stallion said, hanging his head, “It is, but I didn’t mean for it to go this way.”

“Oh, I think I see how you meant for it to go!” Cheerilee replied acidly. “Good thing you have an expert to guide you!” Cheerilee swept her hoof in front of her, drawing Dusty’s attention to the cool expressions around the restaurant. “I’d say you're going to need some good advice for getting future dates in this town.”

“You see?!” Iron Will thundered, tucking the grimacing stallion under his arm as he strode out of the restaurant. “You’ve got a lot to learn about the female psyche, but one strike doesn’t end the season! If you’d followed my course to the letter, that mare would have been dessert! Instead, you’re having humble pie!”

Been his dessert!” Cheerilee muttered, moving to leave. “In your dreams, buddy!”

“Madam?” the waiter said, trotting up to the table, “I’m sorry to have to bring it up, but will you be settling the bill?”

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