“Please don’t fire me. Please don’t fire me. It was just the one time and I sprayed everything down afterwards. Please don’t fire me!” Cheerilee repeated her mantra in a worried hush as she hurried through the streets of Ponyville.

It was a bright and sunny day -because wasn’t it just always?- and while Cheerilee certainly liked sunny days just as much as the next pony, today all that sun did was beat down upon her. She was sweating bullets, both from the heat and from her own nervousness.

The Mayor knew. She had to know. Why else would she leave such a short message? “Miss Cheerilee, please come to town hall as soon as possible.” That was not a ‘Come on by, we’ll do lunch,’ sort of message. That was a ‘You left your bodily fluids all over school property. And much like then, you are fucked,’ sort of message.

“Fuck, fuck, fuck!” Cheerilee swore under her breath as she dodged a passing cart filled to the brim with apples.

Cheerilee soon arrived in the town square and barreled right through it to town hall. The magenta mare found herself lucky as someone was leaving just as she was approaching, allowing her to sprint right through the open door.

The schoolteacher nearly lost her balance as she skirted the receptionist’s desk, ignoring the earnest young mare’s attempts to assist her. Cheerilee knew the way just fine, avoiding the too slow elevator and unintentionally slamming herself into the door to the stairs. Luckily, the unyielding door offered something sturdy to lean against.

Cheerilee drew in a deep breath. Once she had regained her footing, she very carefully pulled the door open and stepped into the stairwell. Once the stairs were in front of her, Cheerilee bolted up them. Two, three, sometimes four at a time. She was pulling open the third floor door in no time.

The third floor of town hall housed a boardroom, a relatively small office for the Mayor’s secretary, and the Mayor’s office proper, with a hallway connecting the three rooms to the elevator and the stairs.

Cheerilee paused at the mouth of this hallway, panting. She took a steadying breath, trying to even out her shallow breathing, and ran a hand through her messy mane. She smoothed out the front of her shirt, as best she could anyway. She traversed the hallway as quickly as she could without running, stopping to poke her head into the secretary’s office.

“Excuse me, Raven, is the Mayor in?” Cheerilee asked in as steady a voice she could muster.

Raven looked away from her computer screen and gave Cheerilee a friendly smile. “Yes, she’s expecting you.” Raven then tilted her head, bemused. “Miss Cheerilee, you didn’t run here, did you?”

“No,” Cheerilee replied easily. A lifetime of lying to foals came in handy on occasion.

Raven gave Cheerilee a knowing look and waved her towards the Mayor’s office.

As Cheerilee approached the frosted glass, she could hear muffled voices.

“More to the left. The left. Ah, right there, perfect. Sweet Celestia, you’re good at this,” said the voice of the Mayor. Was she talking to someone?

“You embarrass me, miss Mayor,” an all too familiar voice replied.

Cheerilee sucked in a breath. “Fuck,” she swore again. Well, this was it. She had a good run in the education business. There were plenty of other jobs for a mare with her skill set though, right?

Cheerilee steadied her breathing, made a little finger gun gesture to her temple, and opened the door.

The first thing she noticed was the Earth Pony stallion. He was wearing a slightly rumpled black suit, his dark brown mane already halfway returned to its usual messy state, and he was engrossed in the construction of a sandwich. It was all pretty much par for the course with him.

Cheerilee looked from the stallion to the mare sitting opposite him. Mayor Merry Mare was wearing her red suit today. The one that showed off a bit more cleavage than one would think appropriate. The cream-colored mare was leaning back in her chair, arms folded behind her head, and legs crossed and feet resting on the edge of her desk.

The Mayor only seemed to take notice of Cheerilee when she heard the door close behind her. She looked in Cheerilee’s direction and smiled widely.

“Ahh, Miss Cheerilee, you’re earlier than we expected.”

Upon hearing this, the suited stallion perked up and turned around. He smiled happily once he saw her.

“Hey there, Cheer,”

Cheerilee returned his smile weakly. “Hi, Reuben,”

Reuben’s smile faltered a little as he tilted his head, like a puzzled dog. “You okay there, Cheer? You look like you just ran a marathon.”

Cheerilee shrugged. “I was, uh, out for a run before I came here.”

“You must be famished,” the Mayor interjected. “Reuben?”

The brown stallion jumped a little, suddenly remembering where he was. “Oh, right,” He turned around and scooped up a completed sandwich from the desk. “Honey hay, nut and grain bread, mayonnaise, lettuce, no tomato,” he rattled off as he offered the sandwich to Cheerilee.

Cheerilee hesitated for a moment before shrugging mentally and taking the sandwich, biting into it hungrily. If she was going to be fired, she was going to do it on a full stomach. Reuben watched her devour the sandwich with a look of concern, silently handing her a glass of water once she had eaten half of it. Cheerilee mumbled a word of thanks past a mouthful, washing it down with a gulp of water.

It was only after she stuffed the last morsel past her lips did Cheerilee realize both Reuben and the Mayor had been quietly watching her. She chewed slowly and awkwardly before giving one last dry swallow and setting the now empty glass back on the desk.

“You look better already,” the Mayor noted with a smile, only now taking her feet from her desk and resting her arms upon it. She cleared her throat, getting Reuben’s attention and giving him a ‘carry on’ gesture.

Reuben smiled awkwardly and quickly tended to the partially completed sandwich still sitting on the Mayor’s desk. In a few moments, he was laying the top slice of bread on and handing it over to her.

“White cheese, white bread, little bit of pepper, hay burger patty, and cucumbers,” Reuben recited, making the corners of Cheerilee’s mouth twitch upwards.

The Mayor took the sandwich without a word and took a bite. After a minute or two of thoughtful chewing, she swallowed and gave Reuben a smile. “This right here?” she held up the sandwich “This is art in a deliciously edible format. Honestly, Reuben, I don’t understand why you bother with all this lawyer business.”

“Money,” he replied with a shrug.

The Mayor laughed and nodded. “Fair enough,” she then looked to Cheerilee, “Cheerilee, dear, why are you still standing there. Sit, sit!”

Cheerilee hesitated for a second before doing as the Mayor commanded, Reuben taking the seat beside her. He quickly swiped what remained of the sandwich ingredients into a nearby wastebasket and put his briefcase in their place

The Mayor tapped the tips of her fingers together. “Now, Cheerilee, I’m sure you’re wondering why I called you here.”

Cheerilee nodded, glancing between the Mayor and the briefcase.

“Well, a friend of mine called me just the other day. It was a rather long conversation, so I’ll sum up the important bits. She’s recently inherited an old coastal castle. Now, as I’m sure you can imagine, the property tax on such a thing is more trouble than its worth. Not too long after, our friend Reuben here was giving me a hand with office taxes. And when I mentioned my friend’s plight…. Well, I’ll let him explain.” she gestured for Reuben to begin.

The stallion cleared his throat and shifted in her seat to face more towards Cheerilee. “Okay, Cheer, get this: Celestia’s all about keeping her little ponies educated about the past, right? Well, in the interest of that, historical sites are granted a quite generous property tax breaks. Especially if these historical sites also give educational tours to our impressionable youth.”

Cheerilee’s eyes widened as Reuben’s words sunk in.

Reuben chuckled. “Yeah, you get what I’m getting at. A field trip or two-”

“Educational field trips,” the Mayor interjected.

Reuben nodded, “Right, educational field trips. One or two of those and the castle belonging to miss Mayor’s friend can be declared a historical site. With all the tax breaks that entails.”

Cheerilee looked between Reuben and the Mayor, trying to keep her expression neutral as relief flooded through her. When she spoke, she did so slowly to keep her tone even. “So, I take a class on a field trip to your friend’s castle, they learn a bit about Equestrian history, and your friend cheats the taxpony?”

Reuben scoffed and waved Cheerilee off. “Cheer, come on, it’s not like that. This poor mare just suddenly has some old castle dumped in her lap; she has no idea what to do. I spoke with her on the phone and she told me she damn near had a heart attack when she looked over the tax forms. She’s thinking that family thing or no, she cannot hold on to this place. And if she sells it, it’s gonna get torn down and made into beachfront condos.” Reuben opened up his briefcase and pulled out a few photos. “She sent these over. Look at this place, Cheer.”

Cheerilee sighed and took the proffered photos. They were shots taken some distance away from a modestly sized old-fashioned castle, sitting on a little island just a stone’s throw away from the nearby cliffs. It was likely done at such a distance so that one could appreciate just how high above the waves the place was. Cheerilee had to admit, looking at it; it would be a shame to see such a place disappear.

Cheerilee sighed again and handed the pictures back. “I understand what you mean, Reuben.” she chewed on the inside of her cheek a moment before looking to the Mayor. “There is some historical value to the place?”

The Mayor nodded. “Architecture and craftsmanship aside, I’m told it did house a few interesting if relatively minor figures of history.” the Mayor tapped her fingers against her desk a few times before leaning forward. “Listen, don’t think of this as being used to help preserve a bit of history and a good pony’s coin purse. Think of it as a paid vacation.”

Cheerilee’s ears perked up. “Paid vacation?”

The Mayor grinned and nodded. “Yep. You’d spend the night, maybe the whole weekend if you’re up for it, in the castle. Give the students time to really soak in the place, right? And you would be there too, of course. To supervise.”

Cheerilee was just about to say yes when a sneaky thought wormed its way into her mind. “But, a bunch of foals on an overnight trip to a place like that? Even if the parents sign off on it, if one of them-”

“Foals?” the Mayor interrupted. She thought for a moment before laughing and grinning wider than before. “Ha! Who said anything about foals? You’d be taking that senior class of yours.”

Cheerilee raised an eyebrow. “Them? But, there’s only seven of them.”

“The forms I’ve been looking at say that’s more than enough,” Reuben said.

Cheerilee nodded. “Well, that would be a lot easier. But, seven eighteen year olds in an old, dusty castle for a weekend? I’d almost pick the foals over them.”

“You wouldn’t have to watch their every step. The Mayor’s friend is excited to do the whole tour guide thing, apparently. And, it’s not an old, dusty castle. It’s a big, spooky castle. Probably filled with ghosts and goblins and all other sorts of scary things.” Reuben chuckled. “The Mayor’s friend has you slated for a Nightmare Night stay.”

Cheerilee thought about that. She was sure some of the students would go for that. Probably all of them, even.

“Well…” Cheerilee smiled. “That actually does sound rather nice.”

“A favor for a favor,” the Mayor said. “My friend doesn’t bankrupt herself holding onto the castle and you get a relaxing few days of time off. With pay.”

“And the kids learn something. And we preserve a little bit of history.” Reuben added.

The Mayor waved her hand dismissively. “Yes, yes, I suppose that too.” she laughed again. “So, do I take it you agree, Cheerilee?”

The magenta mare nodded. “You can count me in. Although, I suppose I’ll have to print up the sign off sheets.”

“I took the liberty,” Reuben said as he pulled the papers from his briefcase.

Cheerilee smiled as she took the papers. A paid stay in a castle, on Nightmare Night to boot. Just rest and relaxation, far away from any foals. But, with her students no doubt policing themselves when they weren’t being force fed facts, she’d probably be lonely.

Seeming to read her thoughts, the Mayor spoke again. “You know, Cheerilee, it might be prudent to take Reuben with you. Just so he can dot all the tees and cross all the ies.” the Mayor gave her a wink.

Cheerilee blushed. She didn’t even want to know how the Mayor knew about her and Reuben. Maybe he told her. Oh, he was going to get such the spanking for that.

Cheerilee made a small production of sighing. “Well, if you insist, I guess I’ll take him too.”

Reuben chuckled as he closed up his briefcase. “I know I’m a real drag on ya, Cheer.”

The Mayor clapped her hands together. “Now that that’s all settled, I’m afraid I’ll have to shoo you out the door now. I have some important mayor business to attend to.”

Cheerilee and Reuben stood up from their seats, and after an exchange of goodbyes, were out the door. The Mayor waited for a few moments, eyes glued to the door, before she turned to the phone on her desk. She quickly tapped in a number and waited with held breath as the line rang.

Four rings later, someone on the other end answered.

“It’s me,” the Mayor said in a hushed voice, almost as though she was afraid the walls really did have ears. “We have to meet.”

She listened a moment.

“The usual spot. How soon can you be there?”

The answer came quickly.

“Really? Perfect,” the Mayor glanced at her clock. “Just, one last thing. …Is, ah, is everyone going to be there?”

The Mayor grinned widely at the answer.

“Good, good. I’ll see you soon, then,”

And the line went dead.

“Shit,” muttered Merry as she fumbled with the cheap plastic lighter in her hands. The thing was stubbornly refusing to work properly, leading to the tried and true method of making things work:

Verbal abuse.

“Come on, fucker. Light!”

And like that, a small flame burst from the tiny hole on top of the lighter. Merry was so overjoyed she nearly allowed a sudden gust to blow it out. Muttering more swears past the cigarette in her mouth, she cupped a hand near the lighter and brought it to her lips. She held it to the end of the cigarette for a few moments and took a few puffs. Satisfied it was lit, she allowed the lighter to go out as she leaned back against the hood of her car, taking a proper drag.

She closed her eyes, savoring the first puff of the first and last cigarette of the day. She gently took it from her mouth and exhaled, opening her eyes again. She tucked the lighter in the pocket of the grey overcoat she wore and stuck the cigarette back between her lips.

Merry looked around, chuckling softly. Who would have thunk that a respected politician like herself would be sitting on a lonely country road at dusk, awaiting the arrival of a shadowy figure.

Another drag, another exhale. There was a name for this time of day. The time when the sun had barely set, leaving the sky still light, but the land dark. What was it? …The magic hour, that was it.

Merry fiddled with her ascot and then smoothed her shirt and pants. She puffed a few times as she regarded her watch, tutting at the time. They were usually quite punctual.

Then, as though the universe had heard her thoughts, a black limo cleared a line of trees and turned in her direction. Merry shielded her eyes from the limo’s headlights as it came to a stop. The driver helpfully switched to low beams after a moment.

She heard a door open and close and the sound of footsteps approaching through the dirt. A figure walked out towards her, their features quickly becoming visible.

“Hello, Setter,” Merry said as she pulled her cigarette from her lips.

“Evening, Miss Mayor,” Wire Setter replied in that smooth whiskey voice of his.

Merry smiled. She couldn’t help it with Setter. He just had an air of… sharpness about him. Which was something for a Pegasus. He wasn’t going to grace any magazine covers, but he certainly was pleasing to look at. And he was always wearing a green button up shirt to match his green fur. But his eyes were the best part: a most pleasing shade of yellow, and glittering with intelligence.

“You said you had something for us?” Setter was saying as he ran a hand through his shaggy yellow mane, bringing Merry back to the moment.

“Yes, and you are going to love it,” Merry said as she stuck her cancer stick back in her mouth and crossed her arms in a cocky pose. “I can get you nine.”

Setter was silent for a moment, head slightly cocked to one side. “Did you say, nine?”

Merry nodded. “When you said this was going to be our last deal for a while, I thought I might as well go all out.” She rested a hand on the small metal case that sat beside her on the hood. “I got all the files right here.”

Setter was quiet for a few moments more, and then he smiled. “She feels that same way.”

Setter looked over his shoulder and nodded. There was the sound of another car door opening and another figure approached holding a duffle bag. The figure quickly handing the bag off to Setter and retreated before Merry got a good look at them.

Setter took a moment to heft the bag before offering it to Merry, who grunted a bit louder than she liked as she took its weight.

“It was supposed to be a goodbye present, but she feels like you’ve more than earned it.” Setter said with a smile as Merry set down the heavy bag.

Merry nodded and fidgeted for a second before speaking. “I, ah, was wondering something.”

“Yes?”

“I want to… meet her.”

Setter blinked, but otherwise his expression remained neutral. He tilted his head, listening to his employer speak into his ear. After a few moments, he nodded, more to himself than her, and indicated for her to follow him.

Merry followed Setter towards and past the limo’s headlights, moving along its body until they came to the door near the back. Setter stopped at the door and awkwardly cleared his throat, scratching his cheek. Merry raised an eyebrow. Setter looked embarrassed for a moment before whispering: “She hates smoke.”

Merry let out a soft ‘oh’ before pulling the cigarette from her mouth and tossing it to the ground, grinding it out with her heel. Setter gave her something of a charming smile and opened the door for her. Merry climbed inside and pulled the door closed.

The interior was pitch black. Merry sat there on what were some quiet comfortable seats for a moment before she heard a click and the light on the ceiling came to life. Aside from the soft creamy coloring of the interior, the light made something else apparent: she was alone.

Before Merry could ask aloud if this was some sort of joke, the soft crackle of a speaker drew her gaze in front of her. It seemed Setter’s boss had retreated behind a privacy wall that cut the passenger compartment of the limo in half. Just below a blacked out window was a small speaker.

“You wanted to meet me?” a distinctly female voice asked, filtering through the speaker.

Merry inspected the privacy wall for a button before the voice clarified itself.

“Just talk, dear,”

Merry cleared her throat. “I did. Want to meet you, that is.”

“Why?”

Merry chuckled nervously. “Well, it’s just that, even after all of the, uh, transactions we’ve done, we’ve never met face to face.”

“Would you really want to?” the voice asked. “You haven’t been told what it is we do, but I imagine some one like you could make… inferences.”

“Oh, I have,” Merry paused and took a breath. “That’s actually why I wanted to meet you. I have a, request of sorts.”

“Oh? And what sorts are you requesting?”

Merry tripped a bit over her next sentence. “I want to come with you. On this next, ah…”

“Hunt?” the voice supplied.

Merry smiled nervously, almost like a foal with a hand in the cookie jar. “Yes. I want to come with you on your hunt.”

“Hm,” the voice sighed, accompanied by a fizzle of static. “Did you want to participate?”

“Goodness, no,” Merry said, adjusting her glasses. “N-not to mean anything bad by that, it’s just not my, uh, thing.”

There were a few breaths of silence, and then there came the soft hum of a motor coupled with the gentle scrap of glass on rubber as the glass window descended just a few inches. Merry heard the voice again, but now unmarred by electronics. It tickled her senses as though speaker’s tongue was in her ear.

“So, you like to watch?” the voice was amused.

Merry felt a hot blush begin to color her cheeks. “Y-yes,” she admitted.

The glass descended further, giving Merry at least a partial view of her client. A reptilian face all but leered at her; golden eyes sparkled with amusement while green lips pulled back in a smile that revealed a mouth full of sharp, white teeth.

“Then I look forward to seeing you there.” Her host paused, a fleshy red tongue moving behind her fangs as she thought about something. “Mmm, and do me a favor, dear. Wear something slutty.”

The Mayor and her client shared a laugh.

“I’ll make sure to do that,” Merry replied with a smile.

“Well, I suppose I’ll be seeing you again come Nightmare Night,” her client said, letting out another soft chuckle. “Until then, my dear Mayor.”

“Until then,” Merry replied, taking the cue to open the door and exit the limo.

Setter was waiting for her outside, standing straight-backed with his hands folded. He looked towards her as she clamored out of the vehicle and shut the door, but was otherwise silent. A moment later, he tilted his head again and then broke out into a wide grin, his shoulders shaking with quiet laughter.

“Oh, miss Mayor. If sources are correct, you’re some sort of sexual deviant,”

Merry returned the grin and waggled her finger. “Now, now, Setter, don’t act all surprised. I am a politician, after all.”

Setter snickered. “Fair enough,”

Merry started walking back towards her car, Setter following beside her. When they arrived at it, Merry took the small metal case and handed it off to Setter. After that, they both turned and faced each other, something of an awkward silence stretching between them. Setter managed to say something first.

“I look forward to seeing you on Nightmare Night, miss Mayor,” Setter said, his wide grin fading into a gentler smile.

Merry returned the smile. “As do I, Setter,” she said as she leaned in closer and dropped her voice to a huskier tone. “And call me Merry.”

Between his fur and the glare of the headlights, it was practically impossible to tell, but Merry thought she saw the stallion blush.

“Alright then, Merry,” he replied, putting just enough emphasis on her name to send a shiver down her spine.

And then, with a tilt of his head and a nod, turned and made his way back to the limo, vanishing behind its lights. She heard the engine purr and the dirt shift beneath the tires as the vehicle backed up. It managed to find a level enough spot to turn itself around and head back the way it had come, vanishing behind the line of trees.

Merry leaned back on the hood of her car again, blowing out a breath. Of all the creatures she imagined her client was, a Lamia was not among them. She reached for a cigarette, only to remember she had already ground out her last one. She snorted and pushed herself off the hood of her car, making her way towards the driver’s seat.

She climbed in and started the ignition, the radio clicking to life. She shook her head and muttered.

“Should have known it was a big fucking snake.”

Author's Note

You may remember a story called The Serpent and the Cheerleader from last year. I found it difficult to finish partly due to being a lazy bastard and, upon reflection, because the concept was quite flawed. Anyway, I threw out the original set up and replaced it with The Most Dangerous Game.

Okay, I say The Most Dangerous Game, but what I mean is Hard Target, but you get the idea.

Anyway, this Author's Note is dragging on. So I'll just leave this here: