Notes: I'm back with my first pokefanfic in... Years. Check my profile if you're really curious, lol. This was a random what-if idea I've been working on for a while, a pre-canon divergence AU if it wasn't obvious from the summary. I finally finished [the draft of] it a few weeks ago and now I'm posting. It is a Jessie/James story, or it gets there eventually. I'll try for updates every other week, but even though it's mostly done, after 2020... Haha... Not going to count on personal or even world circumstances not slowing me up. But still, that's the plan for now. I hope you all enjoy.

Though it's not the ultimate focus of the story, fair warning for some depictions/mentions of various types of abuse. This will be the only warning for all chapters.


1

Jessie slammed the door to the meeting room open, not caring what anyone's reaction would be. Two agents sat with Meowth, each pouring over a different set of papers. One immediately left, and Jessie didn't stop him. "Hey," she began, glancing at the note clutched in her hand before glaring back at Meowth. "What is this you've got me doing?"

"Hello Jess, what's the issue?" Meowth said, leaning over with a smile as the remaining agent, Mondo, pushed back from the table as if to remove himself. "Well, you're good at this kind of stuff, right? This should be a piece of cake for you."

Upon hearing the compliment, Jessie calmed down from her initial anger, but still scowled. "I know I'm near perfect at playing a part for anyone, for an afternoon, maybe even a whole weekend event. I can pass as someone familiar from a distance, or make up a whole new persona." Jessie sighed happily as she complimented herself, then opened her eyes and glared at Meowth. "Neither is what you're suggesting here! Can't you think of a better plan than this?"

"H-Hey, it's not just because you're my best bud or something, but you're really perfect for this part. Take a look." Meowth offered a picture.

Jessie studied the image as Mondo looked back and forth from his own copy to Jessie. "Wow, I thought so before, but seeing Miss Jessie now, she really does resemble this person. She could fool anyone, they look like twins!" he commented.

Jessie rolled her eyes as she studied the person in the picture. The woman with curled hair wasn't just dressed fancy, she also had quite the self-involved expression. "I don't see that much resemblance."

"Well, of course, you're much more beautiful. But Master Meowth is right, you could play this part perfectly," Mondo gushed.

Meowth sighed after Mondo's words diffused things. "Right," it agreed. "Couldn't you just listen before you say no? There's more to it than what's on the memo!"

Jessie still folded her arms, though she relaxed and sat down with them. "Fine, I'll hear it," she agreed.

Meowth nodded. It slid some papers around before finding the newspaper article. "This family that has really pissed off the boss recently, but not on purpose. It's not like they want to go against Team Rocket, but they've become a wild card. They've been getting in the way, you could say."

"And what does that have to do with the 'undercover' thing you want me to do?" Jessie asked, glancing away from the paper without interest.

"That family you'd be going into is the one! They're buying what the boss wants as 'investments', then not investing in his science projects."

"The parents of this guy, you mean? You think I could change their minds undercover?" Jessie said. That might not be as bad as what she was thinking.

"That's part of it. You could influence them to do what the boss wants. Even if that doesn't work, maybe you can make plans for us to steal a bunch of valuables from them. This family is majorly rich!" Meowth passed over more paperwork which Jessie declined to read.

"So, I'd have to pose as this guy's fiancée? First of all, I don't think I can trick someone that's that close, and second of all, what if the real fiancée shows up?"

Meowth nodded. "Here's the story. They've been engaged since they were kids, and from what I found out, they're not close. They should have married as soon as they grew up, but then she decided to go study in Kalos. She's done with school now, but decided not to come back for almost a year now. We'll gonna have you be her, finally returning!"

"It's still weird," Jessie said, shaking her head. She did have fantasies about being someone's fiancée, and maybe it wouldn't be so strange to just play the part for a day... But this long term thing, being with a guy that thought they'd get married for a while... That could get uncomfortable.

"Come on, Jess! This is our chance to turn things around for us!" Meowth pushed. "Just give it a chance. You could leave any time once we get started."

Jessie sighed, then nodded. They were having a streak of bad luck as far as their work went. The disaster on the St. Anne was blamed completely on them, and they hadn't had a successful mission since. This really could help them. "Fine," she said, scowling again as she looked at the picture of the person she was going to 'be' for a while.

"Thanks, Jess!" Meowth said, tapping its friend's hand with glee.

"I envy this guy... Getting married to the lovely Miss Jessie," Mondo said, sighing as he stared out into space.

"Mondo!" Jessie shouted loud enough to shake the thoughts out of her junior's head. "Don't go thinking any weird things. Same for you, Meowth! I mean it. There's not going to be any wedding. I want to get in and out of this assignment as soon as possible."


Walking up to the mansion from the limo, Jessie was sure she perfectly fit the part. As much as she hated to admit it, once she'd done her hair and put on this kind of overly fluffy dress, she did look a lot like that woman in the picture. Any differences should have a minimal impact, since this loving fiancée hadn't visited her suitor for half a decade or so. This idea wasn't nearly as bad as Jessie had considered it to be before.

Or so Jessie thought for a few minutes, before she rang the doorbell and the couple answered it. "Jessebelle!" the woman said, giving Jessie a hug. "It's been so long, and it's so good to see you."

"Yeah, I mean..." Jessie froze a second. "Yes, I'm happy to see you again, Miss, um-"

"Oh, dear, I know it's been a while, but there's no need to be so formal. Just call me 'mother', as usual."

This really was weird, Jessie thought, but took a deep breath before she truly dove into her character. "Mother, Father, I can't tell you how overjoyed I am to be back!"

"As are we," the father spoke up. "I know our son has missed you as well. He's so undeserving of your hand, so we'll thank you in his place."

"Oh no, I'm the one that's undeserving," Jessie said. As the man raised his eyebrow, she laughed to cover up any unnoticed faux pas. Her new 'mother' began to laugh as well, and stepped aside, inviting Jessie into the house and down the hall where a delicious looking lunch was already prepared. Jessie made sure to eat daintily, following any high class rules for eating that she'd studied.

If she made any mistakes, they didn't appear to notice. Jessie's new 'parents' just engaged in small talk with her about various things, such as the weather. It was pretty tedious, but Jessie was sure to lay on the politeness and not go into detail about 'her' stay in Kalos or all the things she'd studied in school. Everything was just so beautiful, her schooling was just so valuable.

Eventually, the conversation faded, long after they'd finished their lunch. As the father took his leave from the room and the servants cleaned the dishes, the mother turned to Jessie. "You must be so tired from your travels. Do you want to go upstairs and unpack? Oh... I'd just thought of this, dear. When will your luggage arrive?"

Jessie froze, mentally berating Meowth for the oversight. Of course a rich girl should have a lot of luggage and she'd just come in this costume with a small purse. "The airline lost it, but they'll deliver it soon!" Jessie quickly thought of an explanation.

"How troublesome. Well, perhaps you'll be able to manage with what you left in your room. We can go out tomorrow for anything you might need if your luggage hasn't been delivered by then. Have a nice rest dear, we'll call you for dinner."

Jessie nodded. She stood up, and hesitated at the door. There was another oversight of Meowth's 'perfect plan'. The Jessebelle girl knew this house well, having visited regularly since she'd been young. She even had her own private room. Jessie wasn't sure which way to go in this ridiculously sized mansion. "Excuse me," Jessie began, improvising. "Would it be too much trouble to have help carrying my bag up?" Maybe that request was too weird, but it was the best Jessie could think of.

"Of course not, dear! I'm sorry I hadn't thought to offer it in the first place." The mother nodded to butler before turning back to Jessie. "I can't imagine why he decided not to join us, but James should be upstairs. I'm sure he's looking forward to seeing you."

Jessie tried to appear thrilled, but her face settled into an anxious state as the help led her to her destination. She tried not to stare too much at the fancy displays and decor in the hall, and look like this was all normal for her. "Um, where is..." Jessie paused to remember 'her' fiancé's name. "James?"

"Master James's room is the same place as before, connected to the same sitting room as yours."

Jessie nodded. Once they came to 'her' bedroom, she let out a brief noise of surprise despite herself. The place really was impressive. The bed seemed far too large for one person, and there was enough space for a decent sized apartment otherwise. The room was similarly adorned to the outside, and perfectly clean. It was almost like a museum. Jessie took a look outside the window in the expansive garden, and then took a peak at the large private bathroom with both a generous soaking tub and decoratively titled shower.

"I'm sorry, Miss Jessebelle, I had almost forgotten to pass along the message."

"What's that?" Jessie asked, turning back to the man who had just dropped her bag on a table.

"Master James said he was going to wait to greet you in private, in the sitting room. I believe he's there now."

Jessie nodded. She'd almost been getting caught up in all the luxury. She could get used to this kind of lifestyle. But she was here with a job to do, and that involved making nice to the family's bratty heir. As a fiancée, no less. How did these two greet each other? Was it something like a handshake, since Meowth had said they weren't too close? They were getting married though. He might expect a hug, or a kiss. Maybe he'd even expect the two of them to get really close and personal, though that wasn't happening.

Still, she had to greet him. For all she knew, that servant had gone right off to tell this guy that his long awaited fiancée was there at last. She could put him off a while, but too long might arouse suspicion. She may as well get it over with. Jessie approached the door which likely led to their connected sitting room, opening it without further hesitation.

Inside, a long haired man sat, his back to her. Jessie noticed him shudder as if in surprise as the door opened, but then he didn't acknowledge her further. She stood, frowning at the rudeness. Maybe he was asleep, since he didn't bother with even a hello. Jessie might have believed that, other than the initial reaction.

What a jerk. If he really were her fiancé, she'd greet him with a slap upside his head. But he wasn't, and she had to play the part. "Well, if it isn't James! It's been so long. How are you, my darling?"

Even though Jessie laid the sweetness on thick to her greeting, the guy still sat motionless, not replying at all. Well, maybe she had made a mistake, in how she'd acted or reacted, or maybe in the facts. The two of them could have met with each other privately without James's parents knowing, Jessie guessed. She walked around the other side, taking a look at his face.

He didn't look confused, and he wasn't asleep. Rather, he stared at the ground, moving his head away as Jessie came closer to him. How long was he going to keep up the cold shoulder routine? Jessie tried not to take it personally, but the guy still grated on her nerves. Still, she'd play the part of the loving fiancée. "Darling," she began, placing her hand on his shoulder.

"Don't touch me!" James shouted harshly. Jessie pulled her hand away as he swatted at it violently.

With all that force, he only managed to knock himself to the floor. Jessie couldn't laugh, just react with her own confusion at his reaction. Luckily he didn't look her way as he fumbled to get back up.

"What are you doing here?" James asked in a low voice.

Jessie thought about just leaving, since she didn't know why it was even a question. Then she decided to put on the sweet voice again. "What do you mean, dear James? I've finished my schooling, and here I am, for you." Jessie paused, and James didn't respond. "I'm sorry for leaving you for so long," she said, in case that was the problem.

A single sob came out of James's throat. Jessie noticed the tears in his eyes. "You said you'd never come back!" he spoke in an almost whine.

Jessie remained silent from there. There was definitely something that had gone on, something that the parents didn't know about. Still, Jessie had to be here, for her own reasons. "Well, here I am," she said. "It's not so bad, is it? We never canceled our engagement, so you must still feel something for me," Jessie recalled that part of what Meowth had told her.

Finally making it to his feet, James wiped his eyes, regaining composure. He frowned, still turning away, refusing to meet Jessie's gaze. "Don't think I won't tell," he said. He moved his head toward Jessie, though he still looked to the ground rather than make eye contact with her. "I wasn't just making idle threats! I'll give you a chance to go, but if you're here after tonight, I'll tell my parents tomorrow."

Jessie thought a moment before responding. "Tell them what?" she finally asked.

"As much as I need to," James said, picking his head up. Though it appeared he tried to, he couldn't quite make eye contact with Jessie. He turned toward what Jessie assumed was his bedroom door. "I'll tell them everything if I have to!" he said as he put a trembling hand on his door. "So just leave. Now."

As James went into his room, Jessie heard the door locking. She went into her own assigned room, locking it the same, both to the sitting room and the hallway. Sitting as far as she could from both, she turned on her communication device.

"Hey Jess! What's up?" Meowth's voice answered.

"You didn't do nearly enough research! There's something really wrong with this engagement."