Author Notes - We'll be jumping back-and-forth between Jessie's POV and James's quite a bit throughout the story, because I find both of their perspectives too interesting to only focus on one of them. That being said, I'm pretty sure it focuses on Jessie's POV just a bit more. I guess I just find her perspective a little more interesting?

I realised I accidentally made Jessie and James's first meeting rather similar to Jessie's initial encounter with Dr White in the episode 'A Fork in the Road, a Passing of the Ways'. I hadn't rewatched that episode until very recently, but it's more-or-less my favourite episode of the whole show so I'm not really surprised.

CHAPTER TWO - RICH BOY MEETS THIEF

James had not been having a good day. Then again, he couldn't imagine ever having a 'good day' when he was stuck on this property. A good moment between him and his beloved pet Growlie was frustratingly interrupted by his parents demanding to see him. And he knew as soon as he walked into the mansion, and saw them sitting there, that it was going to be horrible.

He tried his best to look as interested as possible as he stood there in front of them, but he was never any good at hiding his emotions. The way he slouched and struggled to look his parents in the eyes gave away his true feelings, he just knew it. But his parents didn't comment on it, aside from one little thing.

'No slouching, James,' His mother said, in a painfully cheerful voice.

He groaned as he righted himself up. Couldn't even slouch in this cursed house.

'We've been thinking…' His father began.

If James didn't hate where this was going to begin with, he certainly did now. There was only one place this conversation could possibly be going. He shuddered just thinking about that name.

'You're almost 25 years old, son,' His father continued. 'And we think it's about time you settled down.'

25… as if that was an incredibly late age to be getting married. With the way his parents talked about it, you'd think the average age of marriage was 15.

'And,' His mother said. 'It's important that there is an heir to pass your fortune down to. You wouldn't want all your money to go to waste, would you?'

It took great effort on James's part not to say 'yes'. A grandchild. That was all they wanted from him, as their only child. A grandchild who'd have to deal with the restrictive and rule-laden life he had to suffer through, and not someone he could simply love for being his child.

And, of course. That meant dealing with her.

'So it's about time you got married!' His mother said. 'It's been arranged for years, and it's about time we did it. Your lovely Jessebelle has been waiting for so long!'

'We're just thinking about what's best for the family,' His father said.

James couldn't take another second of this conversation.

'You mean what's best for you!' He cried.

He didn't give his parents a chance to reply. Heck, he didn't even want to know what they were saying, if anything. If they could respond to that, it'd probably just be denial. He turned around and rushed back out the door as fast as he could, making sure to slam the door behind him. His grip on the door was shaky, like the rest of him was. Once the fury coursing through his blood wore off, he stopped shaking. But he felt exhausted. He sat down on the stairs leading up to the door and sighed.

'What's best for the family…' He muttered. 'Yeah, right.'

He buried his face in his arms. Je- His fiancé was not a patient person. That Arceus-forsaken wedding would be happening before he knew it. And that was when his life would really take a horrible turn. He winced just thinking about her whip. That crack was burnt deep into his memories.

With another sigh, he stood up and walked forwards. No reason. No destination. He just wanted to move. Maybe a chat with Growlie would make it all better. Without that dog, he may have taken far more drastic measures years ago. Speaking of which, where was that little guy? James opened his mouth to call his name, but was interrupted by a loud sound.

'GROWL-GROWL!'

James couldn't help a small groan; Growlie was barking at wild Pokémon again?

'GROWLIE!'

But then he saw exactly wha Growlie was barking at. It was not a Pokémon, but a human who had ended up in the pond.

'What in the world…?

He ran over to the pond as fast as he could, ending up on the opposite side to where Growlie was.

'What are you barking at now?' He asked.

The woman who had ended up in the pond turned around at the sound of his voice. As soon as he saw her face, he gasped. His heart rate spiked. Terror began to overwhelm him. No. Not her. Anyone but HER. There was no doubt about it. The face was identical. So was the shade of red for her hair. It was none other than the woman whose name he could hardly stand to even think about.

'N-Not you!' He shouted. 'What are you doing back here?'

But it took no time at all for that terror to be replaced with - or at least accompanied by - fury. Fury that this lady would dare show her face around this estate again.

'I told you to leave me alone!' He cried.

'W-What?!' The woman said. 'What are you talking about? I've never seen you before in my life!'

'Growlie!'

Growlie was by his side in moments, still growling at this despicable woman.

'Growlie!' He said, pointing at her. 'Use Flamethrower!'

'Flamethrower?!'

Perhaps unsurprisingly, the woman reached for her own Pokéball. James shuddered just thinking about that Vileplume. What a shame, he thought, that such a pretty Pokémon would be forever associated with this devil woman.

'Go, Wobbuffet!'

There was a brief moment where James stopped being angry. Or terrified. For that brief moment, he was just confused. Since when did that woman have a Wobbuffet? And why would she be using that instead of her beloved Vileplume? But Growlie still used Flamethrower.

'Wobbuffet!' The woman yelled. 'Use Counter! … Or Mirror Coat. Whichever one it's meant to be!'

Next thing James knew, the Flamethrower was coming right back at him.

'AAHH!' He cried. 'D-Dodge it, Growlie!'

Which Growlie did with ease. The little Growlithe may not have been trained for serious battle, but he would win any fight if it meant keeping his owner safe.

'I can't believe you!' James said. 'You never give up, do you?! Growlie, use Flamethrower again!'

But then, Growlie stopped attacked. He just stood there, staring at the woman in confusion.

'What are you doing, Growlie?!' James yelled. 'A-Attack her!'

Growlie sniffed at the woman a few times, and then turned to his owner with a shake of his head.

'Wait…' James said. 'Y-You mean, that she isn't really…?'

He knelt down before the woman, who seemed partially worried and partially pissed off. It didn't make any sense. She had the exact same face! But then he looked closer. The hair was too long, for starters. And those clothes… that awful woman would never be caught dead wearing something so raggedly and torn. Then there was the Pokémon. A goofy blue blob was certainly not the type of Pokémon she would never dare to raise.

After a little while, he finally found the words to speak. But not before tumbling backwards like a fool.

'You're… you're not Jessebelle, are you?' He asked.

The woman, evidently, did not like this question very much. She slammed her fist into the water so hard that it almost splashed up into James's face.

'Of course I'm not Jessebelle!' She shouted. 'I don't even know who that is! The name's just Jessie, alright? No pretentious 'belle' at the end of it!'

'Woooob-buffet!' The blue blob said, apparently trying to back her up.

James stared in shock. Their faces, as it needs to be repeated, were identical. And yet this woman wasn't the one he was supposed to marry. He was so shocked by this revelation that the reality of the situation didn't sink in for a few minutes. And when it did…

'Wait a minute!' He said. 'Then what are you doing on this property anyway?! You don't look like the kind of person my parents would invite.'

'Not for anything that concerns you,' Jessie said, crossing her arms. 'Now, leave me alone so I can tend to my business, before I make you leave.'

Somehow, she seemed even more volatile than Jessebelle did. But she didn't have a whip, so that made her a lot less scary in his eyes. Once he (sort of) got over the similar faces, he really noticed Jessie's clothes. They were an utter mess. The kind of clothes he'd imagine someone, anyone, would want replaced as soon as possible. Unless, of course, she couldn't replace them.

His train of thought was interrupted when the woman sneezed. It was more of a squeak, due to her attempt at hiding it behind her hand. Then James realised that she was still in the pond, and soaked to the bone. And the breeze was a little chilly too. No wonder she was sneezing.

'Here,' He said, holding his hand out for her. 'Come with me. Let's get you dried off.'

For her part, Jessie just stared at his hand, and then up at his big-eyed face. Over the course of her nomad life, she could count the number of people who offered to help her on one hand. And that was if she was counting that sweet elderly couple in Hoenn as two different people. She narrowed her eyes at him. There must've been a catch. No way some rich kid would selflessly help a homeless person like her.

But those eyes didn't betray any malicious intent. He had the eyes of a little Lillipup who only wanted to help people. When she looked at Wobbuffet, he was nodding.

'Well?' James said. 'Do you want my help or not?'

Jessie huffed, and got herself out of the pond by herself before recalling Wobbuffet to his Pokéball. She was absolutely dripping, and the sun wasn't doing a very good job of drying her off. James figured that she was denying his help and got up to leave, so he was quite surprised when she spoke next.

'Alright,' She said, sounding like she was accepting under protest. 'I've learnt a lot of things over the course of my life, and accepting help from whoever's willing to give it is one of them. What's the catch?'

James blinked at her a couple times. '... Catch?'

'What do I owe you?'

'... Nothing?'

Jessie cocked an eyebrow, but she was complaining. If he was telling the truth, then there was really no reason to deny his help. James reached out to grab her hand, but stopped himself.

'I can dry you off in the doghouse,' He said.

Jessie chuckled. 'The doghouse? Really? I didn't expect you to bring me into your great big mansion, but the doghouse?'

'Oh, I… the doghouse is that building over there.'

Her jaw all but fell to the ground when he pointed at the smaller manor.

'That's the doghouse?!' She cried. 'Your Growlithe gets a bigger house than most families do!'

James frowned, just a little. 'I didn't build it for him or anything. It was already there before I was even born, and because no one was using it… it's Growlie's dog house. So, uh, if you want, you can come with me.'

While James led Jessie over to the 'doghouse', he couldn't keep his mind from wandering a bit. Whoever this 'Jessie' woman was, it was obvious that she had a wildly different life to him. Most people had a different life than him, but this lady especially. It was clear just from her clothes.

'Well,' He said, when they arrived at the dog house. 'Here it is.'

He opened the doors and brought Jessie inside, who spent all of two seconds in the building before she started gawking at… well, everything. Despite being a mere 'dog house', it was fully furnished and expensively at that. The rooms were big, and were much cleaner than you'd expect a doghouse to be. She didn't seem to notice that she was tracking water everywhere, but Growlie didn't seem to care. He just hopped onto a nearby couch and got himself comfortable.

As soon as Jessie eyed that expensive couch, she settled herself on it too. It was so much softer than the hard dirt she usually had to sleep on. James left, but only for a minute. He came back with a big towel that Jessie swiped out of his hands and wrapped around herself. She let out a sigh of relief and blissful contentment. Aside from that elderly couple, she couldn't remember the last time she felt this much comfort.

James stared at his fidgeting hands, wanting to speak up but not quite knowing what to say. It was dawning on him that he just invited a strange woman into Growlie's dog house. If his parents were to find out, they would not like it.

'Do… do you have anywhere to go?' He asked.

Jessie shrugged. 'Eh. I don't really have a destination in mind. I just wander around.'

'No, I-I mean…' He took a deep breath. 'Do you have a home to go back to?'

He regretted saying those words as soon as they left his mouth. And he really regretted it when Jessie stopped smiling and stared at the floor instead.

'I'm sorry,' He said, quietly. 'I-I didn't-'

Jessie gave him a dismissive wave. 'Nah, it's fine. That's just how I roll. Like I said, I just wander around. It's just me, myself, and my Pokémon. Plus whatever goods I can get my hands on.'

'... Would you…?'

He stopped himself there. It was an insane thing to offer, especially since he had a feeling that the 'goods she could get her hands on' were not exactly obtained legally. Unfortunately, the words had already left his mouth and now he was just standing there. Jessie waited for the rest of it, only to get nothing but silence.

'Would I what, James?' She asked. 'Don't leave me hanging!'

'... Would you like to stay for the night?'

Jessie couldn't believe it. People offering to help her was rare. People letting her stay for a night was even rarer. She could only count two people ever doing that, and they were - you guessed it - the elderly couple from Hoenn. An offer she took without hesitation, because why wouldn't she? An opportunity to sleep in a bed for once? She never expected to be offered it again. And now that she was…

'You'd only be able to sleep here,' James said. 'If my parents saw you, they might-'

'I'd like that,' Jessie said. 'This 'doghouse' will do just fine, I think.'

'Do you want something for dinner, or…?'

He was quite surprised when Jessie reached into her bag and pulled out an unopened cup of instant noodles. That was her definition of 'dinner'?

'Usually I eat these with a campfire,' She said, rather nonchalantly. 'Do you have a kettle or something around here?'

'Uh, yes,' He replied, still a little surprised. 'I'll boil some water for you.'

This 'dog house', meant to be a manor all on its own, had plenty of kitchens. Including one that was only a few rooms down. It never made any sense to James to relegate this entire building as Growlie's dog house, but today he was finding himself somewhat grateful for it. If only because it gave this lady a place to stay for the night.

He thought about her more as the kettle boiled. If his parents found out about her, they'd kick her from the lot right away. He couldn't begin to imagine what kind of life led her to living like this. Let alone a life she seemed to enjoy.

Once the kettle was done boiling, he returned to the room. And promptly let out an unmanly shriek when he saw the gigantic purple cobra just casually curled up next to Jessie.

'Oh, don't freak out,' Jessie said, not even looking his way. 'He's mine.'

James didn't not take his eyes off the Arbok and simply put the kettle down on the floor next to Jessie. She paid no mind to his obvious terror and just poured the water into her noodle cup. Fortunately, it came with disposable chopsticks. As soon as she began slurping them up…

'WOBBUFFET!'

That blue blob emerged from his Pokéball without a command or even a warning. James jumped back with another unmanly yelp. His cheeks turned red - imagine getting spooked by an Arceus-damned punching bag.

'He doeth that,' Jessie said, with her mouth full. 'A lot.'

'R-Right…'

'You might ath well meet the whole crew.'

James held his hands up. 'Now now, that won't be-'

'YAN YAN!'

For the third time in five minutes, James shrieked. A massive dragonfly was high on the list of the scariest Pokémon Jessie could've possibly had. It wasn't any less unnerving when the Yanmega perched on the couch.

'Alright, you can stop that now,' Jessie said, finally having swallowed. 'She's not going to hurt you. If she wanted to hurt you, you'd be dead already.'

'That's, uh… reassuring,' James said, starting to regret letting her stay.

'Okay, my Pokémon are clearly freaking you out. I'm good now. You and your little guard dog can go back to that massive mansion of yours.'

James crossed his arms. 'I may have let you stay for the night, but I don't totally trust you to leave without trying to swipe anything. I'll have to get Growlie to keep watch, just in case.'

Growlie yipped in response and growled at Jessie. Albeit, not nearly as harshly as he was growling when he thought she was 'Jessebelle'.

Jessie just shrugged. 'Fair enough, I suppose. There had to be some catch to letting me stay here, free of charge.'

'It's getting late,' James said. 'If I don't get back soon, my parents won't be happy.'

Jessie looked at the massive window. Late, he said. The sun was just starting to set. Perhaps the rich had a different definition of the word.

'Alrighth then,' Jessie said, once again through a mouth full of noodles.

'And you better not break anything!' James said. 'If anything gets broken, they'll pin the blame on my Growlie.'

'Alrighth! I get ith! I might uthe the thower, but that'th iff!'

James could not believe the total lack of manners on display. The one time he tried talking with his mouth full as a child, he got a smack from his tutor for it. He couldn't help feeling just a little bit of envy for her.

'Goodnight, then,' He said, heading for the door.

She didn't even look up from her meal. 'Night!'

'Wobba-wobba!'

'Charrrr!'

'Yan-yan!'

He smiled. He didn't know why, but he smiled. Despite all being terrifying or at least downright bizarre, those Pokémon were strangely adorable. He left the doghouse and closed the door behind him.

'I can't believe it…' He muttered to the door. 'I'm letting her stay.'

'MASTER JAMES!'

Sebastian the butler was calling out for him, again. James never liked it, learning early in childhood that hearing his name being called out meant another lesson or another meeting.

'I'm coming!' He said, running across the garden. 'I was just saying goodnight to Growlie!'

He tried to tell himself that this didn't mean anything. That next morning, that woman would be long gone and he'd never see her (and maybe a few valuables) ever again. And yet, part of him seemed to think that was wrong.

Meanwhile, Jessie finished off her meal and went searching for a shower. Just a quick one, of course, lest the rich people wonder where their water is going. She wasn't making that mistake again. It was just going to be a short stay. Like spending a night in the inn.

But she could certainly get used to this.

Author Notes - I'm sure at least a few people are wondering this, but don't worry. Meowth WILL be in the story at some point. Very soon, actually. When and how, exactly? Well, for that, you're just gonna have to wait to find out.

Fun fact: Jessebelle got described as a 'harlot' initially. Then as I proofread the story, I realised that wasn't exactly the BEST word to use. It kinda seems mean to ACTUAL harlots, ya know?