Miss Jackson

by schmitthappens21

Rating: teen
Tags: Adventure, Alternate Universe, Romance
Length: 3117

Twilight Sparkle--head investigator of the royal guard-- is sent to catch an illegal prostitute. But Twilight finds out finding is a helluva lot easier than catching.

In the world of Equestria, prostitution has always been illegal. Not only is it a grave sin, but it's apart of federal law. Breaking the prostitution law can result to serious consequences. Everypony obeys it.

Everypony but one.

Twilight Sparkle–head investigator of the royal Guard–is assigned by the princesses themselves to put a stop to pony deemed as Law Breaker. But Twilight never expected finding the criminal would prove to be so hard.

As the chase for the criminal continues, Twilight doesn't know who she can believe or who she can trust.

All she knows is that prostitutes can be pretty damn cunning. In more ways than one.

Note: I don't know a hell of a lot about detectives or prostitutes and the like. But it's AU and Equestria and ponies so…I can do whatever.

Published 1970-01-01 00:00:00 UTC
Last updated 2015-05-24 20:22:32 UTC

Chapter 1: There's A New Investigator In Town

Twilight Sparkle was a smart, clever, strong, crafty pony. But Twilight Sparkle never expected to get into the Royal Guard Investigators, let alone the head of it all.

Only the royal Guard had heard about the prostitute. Most didn't believe it, after all, there had not been a prostitute in Equestria for decades. Lots of the guards were not even born when the last prostitute existed. Others did believe what they heard, but only half of them wanted to do something about it. Of course the other half would never let the princesses know their thoughts on the matter.

Princess Luna had not been banished to the moon when the law of no prostitutes had been passed. Luna stood strongly for the rule and demanded they do something as quickly as possible. Princess Celestia also strongly agreed, but she took some time to determine which ponies to send for this case.

Soon, Celestia had Twilight Sparkle--head of royal investigators--and Trixie Lunamoon--deputy of the Canterlot police--sent to her and her sister. Celestia believed the two would get the job done quickly, for she knew of their past assignments.

"I cannot believe the princesses choose us! They choose us out all ponies, Twilight!" Trixie exclaimed as the two trotted through the castle. Twilight calmly agreed, though she was shaking with excitement. This could be the case of the century and she was leading it!

"Agreed. But we must act professional Trixie. This is the most important case we've ever had," Twilight said, raising her head and walking ever so faster.

"We got to make a good impression." Trixie nodded firmly.

The two unicorns came to a halt when they approached the doors of the throne room. Two unicorn guards stood straight in front of the doors. Twilight trotted up to them, confident.

"Hello sirs. I am Head Investigator Twilight Sparkle, and this is my partner-"

"They're good," one of the guards interrupted. The two guards levitated the doors open. Twilight blinked in surprise before muttering a "thank you" and entering the room; Trixie at her side.

Princess Celestia and Princess Luna looked up when the doors slammed shut behind Twilight and Trixie. "I'm glad you're here," Celestia began.

"Of course, princess." Twilight and Trixie bowed before stepping closer to the princesses. "What is it that you wanted to speak about?" Twilight already knew the answer to that, but it was the only thing that came to mind right away.

"There is word of a prostitute going around all of Equestria. But of course, my sister and I cannot abandon our thrones to put a stop to it. That is why we have chosen you two find the pony and bring them back," Princess Celestia continued.

Out of the corner of her eye, Princess Luna saw Trixie's eyes glimmer.

"Alive," Luna deadpanned. She gave Trixie a firm, yet amused look.

"We trust you can get this done. Quickly," Celestia said, seriousness stuffed in her tone.

Twilight gave the princesses a small salute. "You got it, princess. We'll get this done in a matter of no time."

Celestia smiled. "Thank you. I believe the prostitute was last seen in Ponyville. Try there first, the train leaves in three hours."

Twilight and Trixie walked calmly out of the castle; but once out of view, Twilight smiled widely.

"Oh my gosh Trixie. Do you know how big this is? I feel so accomplished! If we get this solved, you and I will probably get promoted!" Twilight grinned and was shaking with excitement. Suddenly, her smile fell.

"Or-or maybe we won't get it done. Maybe we'll take too long. Or maybe the criminal will escape Equestria. Or the princesses will recruite somepony else! Or-or maybe-"

"Twilight, calm down!" Trixie put a hoof over Twilight's muzzle. "We'll get it done. Or else my name isn't Deputy Trixie Lunamoon!"

Twilight rolled her eyes. Trixie could sure brag sometimes. Correction, a lot.

"Alright." Twilight took in a deep breath. "Let's catch that train to Ponyville!"

Trixie found herself bored on the train, the scenery wasn't anything special. Just the same old, same old. Turing her head away from the window, Trixie saw Twilight looking through the notes they had so far.

Age: Unknown

Sex: Unknown

Race: Rumored to be a unicorn or pegasus

Color: Unknown

Family: Unknown

Last seen: Ponyville, Equestria

It was barely anything, and what they did write down mostly consisted of unknown. But, it was something.

"Do you think they're in Ponyville, Twilight?" Trixie pondered, stifling a yawn.

"Perhaps, if it's an earth pony. If the prostitute is a unicorn or pegasus, then they might be gone." Twilight did not look at Trixie, she simply stared holes into her seat. "Luckily, the train ride isn't a whole day."

"But it is boring," Trixie groaned.

When the train screeched to a stop, Twilight and Trixie were the first ponies out. Trixie snorted at the sight of such a country town. Twilight looked everything over, almost as if she was trying to photograph everything.

"Come on, let's get a hotel." Twilight began a slow trot, levitating her light luggage behind her.

The two mares came across a fairly decent hotel soon enough, they had only passed a few houses and a library that Twilight looked at until it was out of sight. Trotting up to the front desk, Trixie asked the earth pony mare for a room.

The mare looked over to Twilight. "Why are their Canterlot police in Ponyville?"

Trixie blinked in surprise. "Why do you think that?"

The mare nodded at Twilight's bag. "She has a Royal Guard Investigators star on it."

Trixie did not even have to look to know what the mare meant. "Of course," she muttered under her breath. Then, so the mare could hear: "We're hear to for an investigation."

The mare cocked an eyebrow. "Why? Nothing worth investigating had happened here for a while."

Trixie shook her head. "I cannot tell you that, ma'am. But you needn't worry."

The mare sighed. "Follow me."

When the three got to the room, the purple mare stopped them before giving them the keys. "If you're looking for news, talk to Miss Rarity at Carousel Boutique. She always keeps up with the latest gossip."

Twilight smiled. "Thank you." Not many ponies knew about the case yet, but there would always be noisy ponies who would find the latest talk of the town.

The mare gave Twilight the keys and shut the door. Only when the sound of hoofsteps disappeared did Twilight turn to Trixie. "Okay, let's find this mare."

Maybe the case of The Law Breaker wouldn't be as hard as the princesses made it out to be.

Chapter 2: Two Down

"Hey um, Twilight?"

Twilight turned away from the window to the sound of Trixie's voice. "Yeah, what is it?"

"I found that mare we were looking for."

Twilight straightened her back, surprise in her eyes. "Show me."

The two unicorns were treading down the street to a fancy looking house. It was probably the nicest house in the town. When they approached the door, Twilight noticed it was called Carousel Boutique. The sign in the window read: CLOSED.

The door opened with the ring of a bell. Hoofsteps could be heard coming towards them.

"Did you read the sign? We're closed." The voice sounded as if it belonged to a pony who belonged in Canterlot, not Ponyville.

A white unicorn with purple mane turned the corner. To Twilight, she was beautiful. But in a slight slut way. No matter, she was still beautiful.

"Oh, it's just you," the unicorn said to Trixie. She glanced at Twilight. "I see you've brought a friend."

"This is Miss Rarity, Twilight," Trixie introduced. "Miss, this is Investigator Twilight Sparkle."

Rarity looked Twilight over before sighing. "I suppose this will take long." She floated a drink to her muzzle. "Follow me darling."

The three unicorns settled down in what Twilight assumed the living room. Trixie and Twilight took the couch while Rarity sat across from them in a chair.

Rarity took a sip of her drink. "Okay, what is that you want."

"I've heard you've interacted with the Law Breaker," Twilight began.

"Indeed I have."

Trixie began her writing.

"When and how many times, exactly?"

"Three times now. All happened five days ago. You're a little late, darling," Rarity chuckled.

Twilight frowned. "And who is this pony?"

"Ha! I thought you would've came up with a better way to get it out of me. Don't you wish you did know," Rarity said.

Twilight smirked. "As soon as I saw your face I knew you would never give me a direct answer. It was no use to beat around the bush."

Twilight saw Rarity's eyes glimmer with surprise.

"Can you describe them then?" Twilight continued.

"I can. But not in too much detail. Otherwise your little game would not be much fun then, now would it?" Rarity batted her eyelashes.

"Her mane glowed in the sunlight, along with her eyes. Her eyes are wide and bright." Rarity pondered for a moment. "And seductive."

Trixie's pen scratched against the paper. Twilight never took her eyes off Rarity. "Her?"

Rarity hesitated for the slightest moment. "Yes, her."

Trixie wrote that down as well, Rarity continued. "Her fur is silky soft, and practically made of muscle. Quite fun if you know what I mean." she winked.

"Can you give me a name?" Twilight pressed.

Rarity hesitated before leaning in. She smelled of cigarettes and vanilla. "Miss Jackson."

Back in the hotel, Twilight lit up a cigarette as Trixie searched for the pony Rarity named.

"There's no pony with the first name Jackson, Twilight," Trixie reported.

Of course Rarity would not give her an easy name. She promised to be indirect.

But they did know one thing, it was a mare. In all honesty, Twilight did not expect a mare.

"Damnit. What's the closet to Jackson then?" Twilight asked from the balcony.

"Um...Applejack. She's right here in this town too"

Twilight took a drag. "Then we'll find her tomorrow."

The next day, Twilight and Trixie trotted down the dirt path to the farm Sweet Apple Acres.

There was a big red barn and a house next to it. Twilight took the latter on which to knock on.

When the door opened, Twilight expected to see a pony around her height standing there; but that wasn't the case. Looking down, Twilight saw a small fully with red mane staring up at her.

"Hello there, could you please bring Applejack to us?" Normally, Twilight would've showed her badge, but she wasn't sure if the filly was old enough to understand. She never had a younger sibling.

"Sure," the filly responded in a country accent. Seconds later, she returned with an orange earth pony with blond mane and a brown cowboy hat to top it off. She was quite pretty.

When the filly left with a slam of a door, the mare's green eyes looked from Trixie to Twilight.

"What do y'all want?"

Twilight and Trixie showed their badges in unison. "Investigators of the royal Guard. May we ask a few questions?" Twilight asked.

The pony sighed. "Sure. But not here. Follow me," she said in an accent as well. She lead them to the big red barn.

"So what did y'all want to ask me? Oh, and ah'm Applejack."

"Head Investigator Twilight Sparkle. And this is Deputy Trixie Lunamoon," Twilight gestured to her partner. Trixie nodded stiffly.

"So ah'm guessing y'all are from Canterlot?" Applejack guessed.

"Indeed we are. We're here to investigate the Law Breaker crime," Trixie said.

"So ah figured," Applejack huffed.

Twilight blinked in surprise. "How would you know? Not many ponies know of it."

"It's because ah've met her."

"So you aren't her?" Trixie said.

"Nope. Ah'm not. Who told you ah was?" Applejack asked.

"Miss Rarity."

Applejack's ears flattened with annoyance. "'Course she would."

"But...is she still Miss Jackson?" Trixie asked.

"Yup. But that's her last name," Applejack said.

"Well then we're done here." Twilight got up to return to the hotel for more research.

"Wait! Aren't ah gonna get like a punishment or somethin'?"

Trixie and Twilight exchanged a glance.

"Did you have a sexual encounter?"

"Perhaps."

Twilight only shrugged. "The system is messed up."

With that, the unicorns left.

Chapter 3: How To Get A Prostitute's Attention

"Ugh!" Trixie groaned. The door glowed blue and it banged shut. "That Applejack basically sent us in a circle!"

"Not necessarily." Twilight opened the computer and typed in 'Jackson,' "Applejack said that Jackson was her last name."

Trixie cocked her head and looked over Twilight's shoulder at the screen. Oddly enough, only about ten ponies with the surname Jackson popped up.

"All we really need to do is figure out some color on the culprit's body and then we can really narrow it down," Twilight said. Her eyes gazed intently at the ponies on the screen.

Twilight was right. Each Jackson pony had different color pelt and. Their manes were different as well, except for two.

"So...how will we not make it obvious to the culprit themselves that we are looking for them?" Trixie inquired.

"We have to look like regular ponies. We can't look like officers," Twilight said, she glanced up at Trixie. "Got it?"

Trixie nodded. "Loud and clear."

Later that day, Trixie and Twilight went their separate ways in hopes of having a better chance at finding the prostitute. Twilight got a spellcasting book from the library and went out to eat at an outside restaurant. She had no luck whatsoever.  Twilight had burned the images of the Jackson ponies in her mind, but she had not found any that looked like the ponies.

Twilight thought intently as she walked through the park. How would they be able to lure the prostitute out? What was something that'd get her attention?

Twilight glanced up to see a couple kissing roughly on a park bench. Only then did an invisible light bulb spark above her head.

"We need to make out!"

Trixie was staring up at the ceiling on her bed when Twilight crashed through the door. She sat up with a start and wide eyes. "Wha-what?"

"I know how to attract the prostitute!" Twilight squealed.

Trixie raised an eyebrow in confusion.

Twilight huffed. "What does a prostitute do? They get payed to have intercourse with ponies. So what will attract them?"

"Ponies fucking in the open?" Trixie tried.

"Well yes, but no. Ponies who practically are but aren't. And if they aren't, that means the prostitute has a chance to get some money and a pony to fornicate with," Twilight explained.

"Ohhhh. So we need to fuck?" Trixie gulped.

Twilight was broken out of her daydream of how brilliant she was. "What? No! We just need to like makeout...like a lot."

"Oh," Trixie deadpanned. "Okay. But like, I'm not interested in you that way Twi..."

"Yes, I know! It's only for the case. So, what do you say?" Twilight said, her eyes pleading.

Trixie sighed. "Fine, but only at night and where no pony can see us."

"Deal!"

That night, the two mares made their way to an alley Twilight said was one for the more popular ones. Or at least the one a pony may be hiding or occupying.

"So, how exactly is this gonna work? I'm not too good with er, sexual encounters; or love in general." Twilight's eyes fell when she muttered the last part.

"Just roll with the punches," Trixie said. She glanced around to make sure nopony besides them was in or by the alley.

"What do you-mpmh!"

Trixie's lips pressed against Twilight's own. At first she didn't kiss back, but when she realized how good it felt, she slowly began to.

The two kissed softly for a few minutes before Trixie decided they weren't making enough noise to draw a prostitute in. Trixie gave Twilight and rough kiss before breaking away. Twilight was already panting. "What are you-oh-oohh." Twilight groaned when Trixie began nipping at her neck. Trixie smirked.

"What are you gonna do for me?" Trixie panted against Twilight's neck.

Twilight quickly shoved Trixie to the ground and pushed her hips into Trixie's. At first the blue unicorn yelped in surprise, but it hastily turned into a moan of pleasure.

As the two continued their makeout session, Trixie found out Twilight wasn't the best at this stuff, but she sure could moan loud. That made up for it. Twilight learned that Trixie's soft spot was right above her private area.

When Trixie figured this was enough before she actually did screw Twilight, she pulled away to see her companion's face flushed. "Shall we take this somewhere more private?"

"Sure," Twilight giggled.

As the two unicorns made their way back to the hotel, Twilight could of sworn she felt eyes burning a hole in their backs. Hers in particular.

Twilight couldn't sleep.

It was nearly 2:00 a.m. Her and Trixie had gotten back to the room at midnight and gone right to bed. She was thinking about the pony who was present during her session with Trixie.

Sighing, Twilight got out of bed and grabbed the keys. Perhaps taking a walk would help clear her mind.

Only by chance did Twilight end up returning to the alley from earlier that night. Curious, she walked slowly into the alley.

Twilight froze when heard wing beats. "Who-who's there?"

When the flapping stopped, Twilight turned her head to see a pair of violent eyes right in front of her. She gasped but didn't move.

"You don't really love that unicorn. Not romantically. Correct?" the pony's voice was raspy, but clear. It was the voice that could be seductive when the owner wanted to be. Although the voice was husky, it was definitely a mare. But besides that, this was the pony who had been watching them.

"Are you- are you the illegal prostitute?" Twilight said. She stuttered at first, but her voice became more strong the more she spoke.

White teeth to accompany the eyes smiled. "Smart one aren't we?'

Twilight frowned. "You won't get away with this for long."

"You sound so sure of yourself," the mare said. "I'm the fastest pegaus there is. Good luck with that."

"Well, you've never met me," Twilight countered.

"We'll just have to see what happens. Catch me if you can, Twilight Sparkle." The pegasus took off into the night, leaving behind a fallen blue feather.

Twilight watched the pegasus fly away, even though she could not see her.

Looks like the prostitute did some research as well.