Author Notes - It's been HOW long since I wrote a Rocketshipping fic?! And it was that hilarious little oneshot I literally wrote in a single day? Well, that ain't right. Let's fix that!

I'll admit, as I started writing this fic, I realised I basically just recreated 'Lady and the Tramp' but genderswapped. It won't be following that movie too closely, but there will definitely be some references and a couple borrowed story beats near the end. Also I'm crossposting this to AO3, which I should be getting into the habit of doing.

CHAPTER ONE - THIEF MEETS ESTATE

Jessie settled down on a fallen tree and searched her small bag for the can opener. Pineapple. Sliced pineapple in a can. Not exactly a five-star course meal, but plenty enough for her. The sun was still high, shining through the thick trees of the forest and covering her with speckled shadows.

Without any knives or forks on her person, she settled for using her hands. Far from her ideal circumstances, but she couldn't be a chooser. After swallowing the first slice, she reached into her bag again and pulled out three Pokéballs.

'Okay, guys,' She said. 'It's time for lunch.'

She tossed the Pokéballs in the air. All in a single swoop and with one hand, impressively enough. The kind of thing only Jessie could pull off so nonchalantly. All three Pokémon emerged at once.

'Chaaaarrrr-bok-char!'

Her Arbok was the first one to cuddle up to her. Despite his mighty size and intimidating appearance, he was quite the cuddle bug. He rubbed his head against her shoulder, and she couldn't help but to pat him on the head.

'Yaaan-mega!'

Her Yanmega took the opportunity to spread her wings, zipping around in the air before settling on a nearby branch. The underside of branches had always been her favourite place to rest.

'WOOOOOB-BUFFET!'

And her Wobbuffet… just kinda stood there. He was her weirdest Pokémon by far. Just some dopey little guy who liked to pop out of his Pokéball announced. After a moment, Jessie realised he was staring at the can.

'Oh, alright,' She said. 'We can share.'

'Wobba!'

He held out his arm, and Jessie placed a couple slices of pineapple in his… well, he didn't really have hands. Still, he took it graciously and gulped it down in seconds.

'Wobba wobba!'

'You're welcome,' Jessie said.

She let out a blissful sigh. This was the life. Roaming around, swiping goods, with just her and her Pokémon against the world. Speaking of which…

'Oh, Yanmega,' She said. 'You can go hunting now, if you'd like.'

'Yan yan!'

Truth be told, Yanmega was quite hungry. So she took this invitation and flew off into the forest in search of prey. What kind of prey? Well, there was very little she couldn't hunt.

'Char-bok?'

Arbok gave Jessie impressive Baby-Doll Eyes, especially impressive as that wasn't even a move he could learn. She scratched the underside of his chin, prompting him to (for all intents and purposes) purr. Despite being a snake.

'No, Arbok, your last meal was only two weeks ago.'

'Charrr…?'

'Yanmega's a quick hunter. She won't be gone long. In fact, she should be getting back here in three… two… one…'

'YAN-YAN!'

Speak of the darner, Yanmega returned right on cue and full of her latest hunt. Of what, exactly? Jessie never knew and never cared to find out. Whatever it was, you can be assured that nothing was left behind. With all her Pokémon back, Jessie finished her meal - if you call it that - and got up to stretch her legs.

She breathed in the wonderful fresh air. This may have been her favourite part of her nomad life - walking around the fresh forests, finding new things and having no idea what was to come. There was only one way to find out, and that was to keep walking. And speaking of which… she reached out for her Pokéballs, but stopped and put them away instead.

'You know what?' She said. 'I think you guys could use a little walk. It's been a while since we've all walked together, hasn't it?'

All her Pokémon cried out in agreement. It was rare they ever disagreed with her, and even rarer that they'd deny an opportunity to roam about. So, it was Jessie and her Pokémon waltzing through the woods together. They stood closely by her side as she walked, making sure they weren't going too fast or too slow.

'So, what are we in for today?'

'Charrr?'

Arbok looked down at her body. Specifically, her clothes. Unsurprisingly, spending your days roaming around without a place to call home was not conducive to the health of her clothing. The pretty shirt and pants she was wearing had faded and worn. There were even a few tears left behind from tussles with wild Pokémon and a close call with a Jenny. A tiny bit of blood too. What a shame. It was a really nice shirt too. The lady she swiped it from had very good taste.

'Yeesh… this look didn't last long. Looks like we're gonna need to find some other schmuck with good taste. What do we think? Go to a good store, or find some socialite to rob?'

The Pokémon seemed quite excited by that second option. Robbing from rich people was the best. After all, if she could live an alright life with hardly any money at all, those people certainly didn't need those massive mansions or buckets of caviar. As tempting as those things sounded at times. Why not swipe a little of it? Call her a modern day Decidueye Hood.

'Alright, Yanmega, see if you can find a fancy looking house anywhere. The bigger, the better!'

'Gah!'

With that, Yanmega took to the skies once again and zoomed off. Jessie had no worries about her finding her way home. Though she did expect Yanmega to be out there for a little while. Scratch that, more than a little. It was exceedingly rare that they'd find some snazzy looking rich place, and unfortunately they had a disturbingly high chance to be home to nothing but Ghost-type Pokémon. That was a night Jessie would rather forget.

So imagine her surprise when Yanmega returned just a few minutes later. Not only that, but was also zipping around with the most excitement she had felt in months. If not years.

'YA!' She shrieked. 'YA YA MEGA!'

She came flying at Jessie faster than she hunted prey. And when Jessie saw the ogre darner rushing at her…

'AAAHHHH!'

She made a sound that she'd never admit to making and jumped back. It was a shriek so loud that Arbok, on instinct, slithered in front of her and prepared to attack. He was just about preparing a barrage of Poison Stings before he realised it was a friend.

'YAYAYA!'

'C-Calm down, Yanmega!' Jessie cried, flailing her arms in a rather inelegant manner. 'What's the matter?'

'YAN!'

'Oh, I barely understand you as it is. I really can't understand you if you're YELLING!'

Once Yanmega realised she wasn't getting her message across, she flew behind Jessie and pushed her body with enough force to make her tumble.

'Ma! Ma!'

'Alright, alright, I'll follow you! You better have found something good.'

Yanmega led the team through the woods while her teammates struggled to keep up. Wobbuffet in particular had to use every bit of strength he had to keep his stubby legs moving fast enough. Soon, the trees grew further and further apart. The sunlight had less to obstruct it. Jessie was getting quite fed up with her bug before - finally - Yanmega slowed down just a little.

'Mega-mega!'

By the time she stopped, Jessie had a harder time catching up with her breath than her. And the boys were positively winded. But Yanmega still hadn't stopped yelling. They arrived at a brick wall, a tall one but nonetheless a wall that Jessie could climb over without any effort.

'This better be good, Yanmega!' Jessie said. 'Or I swear to-!'

She couldn't finish her sentence. Something had caught her eye as soon as she lifted her head up over the fence. Something big. Right before her was the biggest, grandest, most gorgeous estate she had ever seen. The grass was fresh, if mowed a bit too short. There was an artificial pond with a lovely bridge. And, of course, there was a giant manor right at the end of the beautiful garden. It was one of the biggest houses Jessie had ever seen in her long years of travelling. It must've been at least four or five storeys tall!

Her jaw was practically on the ground. Arbok and Wobbuffet shared her stunned expression.

'Oh my Arceus…' She murmured.

'Ya… meg mega.'

Yanmega tapped her shoulder and pointed to the side. Jessie turned her head to look.

'WAH!'

There, right next to the big manor, was an even bigger mansion. It made the manor look like a doghouse by comparison! It. Was. Huge. Breathtakingly massive. Seven, eight… nine?… storeys tall. And drop dead gorgeous too. Jessie (and the boys) must've been staring at it for several minutes just to comprehend the whole thing.

And when she did, she grinned. It was her widest grin yet.

'Oh, Yanmega!' She said. 'I can see why you were so excited. Looks like we hit the jackpot! You did well today.'

Yanmega appeared to blush at this, believe it or not, and her blushing only got more intense when the boys cheered her on too. If the owner or owners of these two gigantic buildings was willing to spend all that money on the outside, imagine all the money they must've had on the inside! Jessie could picture now. Caviar for every Monday. The loveliest clothes for any night out. And, perhaps even a good room she could spend the night in if she so chose.

She was just about getting her leg over the wall when she heard a sound.

'GROWL! GROWL-GROWL!'

It was the sound of barking. The super rich people apparently had a guard dog. Not something Jessie hadn't seen before, but not exactly something she liked dealing with. She flung her leg back over the wall and ducked down until only her eyes and the top part of her (gorgeous) hair could be seen.

There was a Growlithe in the garden, and he was staring right at her. Just a Growlithe, huh? Jessie had dealt with much scarier things before. Manectric, Lycanroc, and even an Incineroar just to name a few. Some things she even handled with her bare hands. And even if she couldn't, her beloved trio of 'Mons certainly could. A Growlithe would be no match for even her fire-averse Yanmega.

Jessie lifted herself back up and readied herself for a proper fight, when a voice - a human voice - stopped her in her tracks.

'Growlie! Stop barking at the wild Pokémon!'

The (slightly whiny) voice belonged to a man, who Jessie had been too distracted by the massive mansions to notice. To be specific, a man dressed up in the fanciest wear Jessie had ever seen a man dressed in. It was so fancy that she barely even noticed his short and distinctly lavender hair. He must've been about her age, perhaps slightly younger. As soon as this fancy man called out, the Growlithe ran over to him.

'Oh ho ho!' Jessie said, as quietly as she could manage. 'Look at the clothes on that guy. If that's the kind of thing he can just wear casually, then he must be loaded with cash! And he looks like he won't be hard to deal with at all.'

The man knelt down and gave his Growlithe a pat on the head. 'Growlie', as he was oh-so-creatively named, yipped with glee. Jessie had to admit, it was cute. Arbok was even watching it all goo-goo-eyes. But as much as she liked geeking out over cute little Pokémon, there was no time. She needed new clothes and soon, and she had no issue at all wearing a man's clothes.

The front door to the bigger mansion opened up, and a much older man in a suit emerged. A butler, no doubt. And for some reason, he had a megaphone. That was how Jessie could easily hear his words.

'Master James!' He said. 'Your parents are requesting to see you at once!'

The man, who Jessie now knew was named 'James', stood up with a sigh. Resignation was written all over his face. Jessie couldn't help the twinge of jealousy at the word 'parents'. Lucky guy.

'Coming, Sebastian…' He said, sounding as resigned as he looked.

It didn't take long for him to disappear inside the building. A small part of Jessie felt kinda bad for the guy, though she couldn't imagine why he'd look so sad when he lived in a place like that. But only a small part, because Jessie had things to do. The garden was seemingly empty. It was time to go looking around.

'Alright, guys,' She said. 'I'll need you to return to your Pokéballs for now.'

Her Pokémon didn't complain for a moment, allowing her to recall all three of them. On her own, she could easily vault over the fence. And she did. Once on the property side of the fence, she felt a thrill run through her. The thrill of 'you shouldn't be here, and that's what makes it fun'. She wasted no time making her way across the yard.

'Geez… are these people show-offs or what.'

The yard didn't seem so big compared to the mansions - she still couldn't get over that - but it was still gorgeous. She found herself getting a little distracted by the topiaries shaped like different kinds of Pokémon. Mostly the 'regal' looking ones, like the Nidos and Gardevoir. Not even something cooler like an Aegislash, and certainly not a 'common' Pokémon like her beloveds. Very pretentious, but if Jessie ever told you that she didn't find them beautiful or want one for herself, she would be lying.

They had a fountain. A gorgeous, clean fountain, shaped like a Horsea. The garden path was perfectly paved and had almost no dirt on it. The whole yard was free of any litter. It didn't take long for Jessie to forget about her 'rob the rich to give to the poor (me)' plan and get distracted with the pretty sights instead.

'I gotta come back here again. This is too good to only steal from once!'

She got so distracted, in fact, that she didn't quite realise where she was standing. Nor did she realise that she wasn't the only one standing in the middle of that garden. Not until she heard a rather familiar sound.

'GROWL-GROWL!'

'Ah!'

That blasted 'guard dog' was running up behind her. Jessie could not believe how unobservant she had been. Years and years of constantly getting away with all sorts of theft, followed up by forgetting that a guard dog existed? She blamed the pretty decorations. It was their fault for distracting her so much!

The sudden bark of the Growlithe, combined with him charging for her, surprised Jessie so much that she fell backwards.

SPLASH!

Directly into the artificial pond she didn't realise she was standing right next to. It wasn't that deep, but she fell right over and was fully submerged for a few moments. Once she got her head out of the water, her gloriously-long hair had collapsed all over her shoulders and back.

'Hey!' She shouted at 'Growlie'. 'You're going to pay for that, you mangy little mutt!'

Her threat seemed to fall upon deaf ears, for the Growlithe kept growling and snarling at her. If that thing had Intimidate for its ability, it must not have realised that Jessie was rather Scrappy.

'Oh, would you shut up!' Jessie yelled. 'If I wanted to, I could kick your behind from here all the way to Alola. Now stop your yapping or I will kick your-!'

'GROWLIE!'

She shuddered. 'Master James' had returned, far earlier than she thought he would.

'What are you barking at now?'

Once again, the decorations distracted her so much that she forgot he was even an element at play. Until, of course, he had shown up at an awful time. She spun around, still sitting in that pond, and saw the fancily-dressed man from before. As soon as he saw her face, he let out the most unmanly sound Jessie had ever heard. A sound that could best be described as a shriek.

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

Jessie flinched and missed her turn. He recognised her? There was no way. No way in the Distortion World that some random rich kid was about to identify a thief notorious for evading people's grasp. His expression shifted to fear. No, not fear. More like outright terror, like Jessie was a famous serial killer instead of a mere petty thief. But then his face contorted with absolute fury.

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

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

'Growlie!'

The loyal guard dog rushed around the pond and stood by his owner's side, still growling at Jessie. She had no idea what this man was talking about. She hadn't even heard of him until now, let alone met him. And certainly hadn't made him angry enough to warrant a reaction like that. But he wasn't convinced.

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

'Flamethrower?!'

He didn't seem to care that she was as soaked as could be, so a Flamethrower likely wouldn't do as much harm as he'd like. But that didn't mean it still wouldn't hurt like hell. With no time to lose, Jessie grabbed her most powerful Pokémon.

'Go, Wobbuffet!'

The blue blob emerged from his Pokéball right on the edge of the pond, standing between her and the Growlithe. For a moment, the fury on James's face was replaced by confusion. Good. He was starting to get that she wasn't whoever he thought she was. Still, the Growlithe unleashed a great big stream of fire from his mouth.

'Wobbuffet!' Jessie said. 'Use Counter! … Or Mirror Coat. Whichever one it's meant to be!'

Fortunately for her, Wobbuffet knew a lot more about the difference than his trainer did and used Mirror Coat. His whole body was coated in a rainbow light reminiscence of oil on water. His rubbery skin suffered only a few scorch marks before the mighty flame was turned around and aimed right for the Growlithe instead.

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

The agile guard dog dodged the counter attack with ease. Jessie gritted her teeth, but didn't lose her cool just yet. With a Pokémon as powerful as her Wobbuffet, it didn't matter what move that Growlithe used. Unless 'Growlie' was just going to Leer at them all day.

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

Growlie stopped growling. He stopped snarling. He simply tilted his head and looked at Jessie in confusion. Jessie breathed a sigh of relief - hopefully, this whole mess was going to end soon.

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

The dog leaned over the edge of the pond and sniffed at Jessie, who stood perfectly still in case he was still prepared to attack. After just a few sniffs, he looked back at his trainer and shook his head.

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

He knelt down so he could get a better look at her, narrowing his eyes. Jessie tried to keep still, but she couldn't help the little twitchy movements. If she recognised him as that notorious thief, then she'd really be in hot water. But, after a little while, he gasped and leaned back so much that he almost stumbled over.

'You're… you're not Jessebelle, are you?'

Author Notes - You kidding me? Growlithe STILL can't learn Growl?! I... It's right there in its name!

Jokes aside, I've been having a LOT of fun writing this one. For the first half (maybe first two thirds) of it, it practically writes itself. What can I say? I love playing around with AUs like this, especially if it's a 'they have a totally different first meeting' kind of deal. I eat it up. So, hopefully, the first few chapters will get here quick! Then I'll reach the point where I'm not entirely sure where to go, but we get there when we get there! I'm just kind of winging it like always.