AN;

Hello readers! Just a few things to help with the story.

First of all, this fic will take place on the same night the V.K.'s chose 'good'. So it's basically the in-between of the end of Descendants and the beginning of Descendants 2, and it's strictly Isle-based.

Warnings; T+
. Language
.Violence
(There will be warnings at the beginning of each chapter so you guys have a heads-up)

Anyway, thank you for reading!

The Isle of Lost was, more often than not, deathly silent when the sun went down. Whether it was because of the fatigue every villain, V.K., and follower felt at the end of such a long and draining day of 'hard work', or because many assumed the worst of the worst roamed the island at night, no one knew. For whatever reason, when night came and the moon shone brightly, the numerous stores and café's on the Isle closed and every single door locked.

But this night was different. Instead of quietness and empty streets, it was now filled to the brim with villains and others alike, hollers, screams, and crashes echoing through each alley and from around every corner. Nothing was left untouched, either. Store windows were being smashed, trash cans were kicked over, and the weaker of the Isle residents who were unfortunate enough to be stuck outside in the cold were beaten down to nothing and robbed of the very little they owned.

The night sky was lit up with a thousand lights, an odd shrieking noise accompanied by a loud 'bang' and a flash of colourful neon dust. The source seemed to be the Auradonians, throwing yet another extravagant get-together. But their ways of celebrating only illuminated the horrific acts being displayed on the Isle, many unfortunate souls only having a glimpse of their attacker when the flashes blew up in the sky.

In the centre of the Isle and tucked safely away in the attic of Bargain Castle, the sixteen-year-old daughter of the Cheshire Cat watched the pretty lights with utter fascination, her dark-brown eyes darting to different parts of the sky as each cloud of beautiful bright dust exploded and disappeared into the night, a thundering 'bang' silencing the screams below after every one.

"Pretty," she hummed in wonderment, slowly reaching out her arm as if she'd be able to catch the falling 'stars' before they disappeared. She couldn't deny that the loud noises scared her sometimes, especially when one of the strange lights came too close to the Isle border, but the alluring colours of bright blues, greens, pinks, and every other colour she could think of truly made it worth it.

Cassie carefully retracted her hand and placed her palms on the cold ledge, pushing herself up and out of the 'window'. She closed her eyes and purred in contentment, the chilly breeze soothing her warm skin.

A deafening 'boom' shook through the broken castle, startling the young girl. She hurriedly came back into the attic and lowered herself to her hands and knees, moving her face closer towards the small gaps in the floorboards to see who had been stupid enough to break into Maleficent's lair.

Since her little 'hideaway' was placed above the top of the stairs, all Cassie could visibly see was multiple men and women rushing up the stairs. She couldn't make a safe guess as to who any of them were; there seemed to be such a mix of Isle dwellers, and, for reasons she didn't know, they were in such a hurry that she barely managed to see any of their faces. From what she could see, however, they were ransacking every room at the top of the castle, pillaging and dismantling whatever they set their minds to.

Cassie didn't know Maleficent or her daughter on a personal level; far from it. All she did was make a home in the small space above their rooms, coming in through a small gap in the wall during the day and leaving quietly down the side of the building at night. They had absolutely no idea she was hiding in their home, and she planned on keeping it that way. She hadn't even thought to question it when neither Mal nor Maleficent came back to their castle that day; she'd just gone about her routine as usual.

Something was going on—something big. The Isle residents never came to Bargain Castle unless they were invited, a very rare occurrence when it came to the women who owned it, and those barging their way in now were hardly worthy. For reasons unbeknownst to Cassie, the two women she prided herself on avoiding weren't in their home, and suddenly the Isle had fallen into complete chaos.

'I have to get out of here,' Cassie thought to herself.

When a fight broke out down below, Cassie slowly and cautiously backed away from the scene and sat up against the window. The pretty glows the Auradonians were sending out had long since disappeared, leaving her with no reason to stay where she was. After all, the fumbling thieves arguing downstairs were hardly interesting, and she had no desire to sit still and watch. She had to get out of the castle, but walking around the Isle when it was in such disarray—and in her human form no less—was a serious risk to take.

'Then again,' she thought as she rolled her eyes skyward. With the majority of the whole island intent on stealing and harming others, there was no certainty that she'd be seen, much less caught by one of them. She was much better on two legs than she was on four, and if the situation came to it, she knew she could get herself out of there. All she had to do was stroll around until a 'special thing' caught her eye, and then she could go home, play with it for a while, and then add it to the growing pile of 'old special things' in the corner of her hideaway.

With her mind made up, Cassie quickly pulled her black flats onto her feet and tied the laces.

Going out when the Isle was in such a state wasn't a good plan, but even though she fully knew that, she couldn't quite sway herself from going out anyway. She couldn't spend another minute in her hideaway with all the ruckus going on down below, and she couldn't possibly do it when she had nothing else to play around with when they eventually went away. Cassie just hoped that, by the time morning came, the thieves would be gone and she could return home for a few hours of sleep before she had to go back out again. After all, her night-time 'walks' were hardly easy, they more often than not took her all night to complete, and this particular night she wanted to bring home something truly beautiful. Something that would keep her unwavering 'needs' satiated for a good few hours at least.

Cassie gave one lingering glance at the pile in the corner of her room before nodding to herself, cementing her decision to go and find something new. She quietly moved up and crouched on the very edge of the window, pressing herself back against the wall as she gracefully walked down the thin, wooden ledge leading to Mal's balcony. From there, she easily manoeuvred herself onto the metal railing, keeping her footsteps light as she bounced down the stairs and onto the ground.

She did question the fact that no one seemed to be following the same path up to Mal's bedroom since they seemed so eager to trash the entirety of the castle, but she decided to store that thought in the back of her mind for now. It didn't interest her one bit, especially since she had a much larger goal in mind, but she'd certainly find out tomorrow when the chaos had died down.

Cassie slowly trailed against the wall until she came to the end, her body firmly pressed back into the stony wall as she quickly peered around to see the main entrance of the castle. With all the thieves trailing in and out of the castle with their arms full of objects and clothes, the young girl knew she couldn't follow the main path out into the main street. If she wanted to keep her chances at survival high, she'd have to take the back alleys and simply hope that there weren't too many villains thinking the same thing.

After sucking in a deep breath of reassurance, she moved, constantly looking around her to make sure she hadn't been spotted as she snuck into the nearest alley. Only when she was a good few steps into the narrow space did she finally ease, blowing a fidgety strand of mousy-brown hair away from her face as she kept her eyes ahead.

When Cassie came to the end of the alley and out into the market, she finally caught a glimpse of the damage that had been done to the Isle.

Ever since she could remember, the Isle had always been in shambles, with the majority of the buildings covered in tags. The old pain chipped away until she had to squint to see it, and whenever she came through, there was always someone cleaning up any remnants of destruction from their front doorstep. But the Islanders had certainly done quite the number on the Isle tonight.

Cassie warily strolled along the street, keeping close to the walls as she occasionally looked down at her feet, making sure she didn't accidentally step on any broken glass as she looked for a 'special thing'. She now knew that, just from seeing the clutter around her, the chances of her finding something truly beautiful were scarce. It seemed that while she was occupied with staring at the pretty lights earlier on, the rest of the Isle had set to work almost immediately, taking the best of whatever they could find in each store.

'Damn it,' she thought with a frustrated grimace. She already knew before leaving the castle that finding a 'special thing' would be hard, what with the Islanders roaming about the place. But she knew now she'd have to work just a little bit harder to find something worth taking since anything worthy had already been taken by someone else.

An echoing thud sounded from just around the corner, and Cassie paused in her steps, slowing her movements as she neared the right turn leading into another street. She crouched low and took a little look around the wall, slightly curious to know what was going on only a few feet away from her.

A little way down the street was a group of five people, three painfully attempting to shoulder-barge their way into Jafar's Junk Shop while another yelled at them to 'put more effort in'. In her human form and without the aid of her feline senses, Cassie could only manage to see the outline of the group.

It amused her somewhat to see how much effort they were putting into their thievery, especially since it was no secret that Jafar liked to securely lock up his store. As far as Cassie knew, it'd never been broken into, and with the owner's son being a thief himself, it only made sense for them to take great precaution when it came to guarding their own 'goods'. But if people were mad enough to go break into Maleficent's castle, then a few random thugs trying their luck at busting into Jafar's place wasn't too surprising.

"Idiots," Cassie quietly remarked with a giggle. Even she wasn't stupid enough to try taking something from Jafar's store at night. She'd only ever gotten lucky once, and that was during the day. And all she'd managed to take was a silly little golden coin from Jafar's back room, with the villain himself chasing her around the store with a broom when he caught her with his precious possession. She'd barely managed to escape him then, and she hadn't been back since. Her eagerness to remain alive outweighed her need to take something 'pretty' from him, and the choice was also a lot easier to make when she soon realised how rusty and fake everything in his store was.

"Would ye' hurry up?!" Cassie heard one of the men growl towards the three trying to break the door down.

"We're trying; it's nailed shut," another moaned in reply.

"Well, then try harder," the first man demanded.

"Hard to bust down a door when you can't see shit. For all I know, I've been throwing myself against the wall."

Cassie stayed where she was, slightly intrigued to see if the group would be successful in their efforts. She was betting that they'd lose to the steel-like door, but the Isle had turned upside down tonight, and anything was possible.

The group fell into silence and Cassie heard something similar to a match being lit. And she found she was correct in her assumptions when a soft glow illuminated the thugs, a small wax candle hidden inside a lantern the only source of light in the street.

With the group now in full view, Cassie took the time to further inspect the bunch. Four guys and a girl. They looked like every other villain on the Isle, with their tattered and torn clothes and dark shades. But the things that set them apart from the others and raised many red flags in her mind were the oddly shaped hats and red bandanas they wore on their heads.

"Pirates," Cassie breathed, a small twinge of apprehension settling in her stomach. She hadn't ever had a run-in with them since they stayed closer to the edge of the Isle and near their ships while she remained in the centre. And to now see them so far from their usual territory was truly a terrifying thing. But she once again reminded herself that everything was in disarray tonight.

"There, now ye' can see what ye're doin'," The biggest pirate of the group, and the apparent leader, took a step towards them and leaned against the wall next to the door, raising the lantern high. "So get movin'."

The banging started up again, the pirates rather persistent in their task to get the door down, and Cassie stood straight, turning to fully hide herself behind the corner.

She knew she had to walk away, leave them to their pathetic attempts and go find her 'special thing'. But there was a small voice in the back of her head urging her to stay where she was, and what was worse was that she knew exactly why she was hesitating.

Cassie had been born and raised on the Isle of the Lost, just as all the other villain children had, and during her travels, she'd also heard about the pirates living near the water. They usually moved in groups of two or more, they never left home without their swords, they were fiercely loyal to whichever Captain they'd devoted their lives to; and—the fact that stood out to her personally—they always sought the best treasure.

Cassie frowned and looked down at the floor, a little unsure about the choice she was about to make. If she walked away, there was no guarantee she'd find her 'special thing'. By now, the whole Isle had been searched and everything worthy had already been stolen. But if she stayed where she was and decided to follow the dreaded pirates, there was a small chance she'd find the beautiful thing she'd set out to find.

The thought of finding her 'special thing' soon floated to the top of her mind, pushing away the small niggling in the back of her head that told her this was a very, very bad idea. So she went back into position, eagerly waiting for the moment they'd give up on the door and go back to wherever they came from.

"We're not getting in there," one of the pirates mumbled, stopping in his task on the door to knead his right shoulder, a flicker of pain crossing his features.

"Sorry Harry," another pirate, dressed in different shades of brown, muttered apologetically.

The pirate who'd lit the lantern gave a loud yell of annoyance, kicking his boot-clad foot against the sturdy door. It was a good and hard kick, but even Cassie knew there was no getting it open.

"We told Uma we were gonna tag all of their turf," he said, his back still turned to Cassie as he leaned his side against the door. "An' that's what we're gonna do. Tag it."

A shorter and skinnier pirate stepped forward, shaking the can of spray paint in his right hand before he set to work, spraying whatever mark they all followed on the front door of Jafar's store.

While the little one set to work, Cassie sat down on the cold floor and turned away from the group. She'd never 'tagged' anything before, and she had no idea how long it'd take, but she was rather set on finding her 'special thing'. All she had to do now was sit and wait.

After what felt like an hour, when in reality it could've only been minutes, Cassie finally heard the group begin to move.

"About time," she whispered, moving to her feet to peer around the corner. She wasn't a very patient girl, and for a good few minutes, she'd considered the idea of abandoning her earlier decision and moving on to another place. But her itching stubbornness had forced her to stay put, and she was somewhat thankful that she had.

She watched as the pirates began to walk away from Jafar's Junk Shop, shouting and hollering and laughing to themselves about all the hard work they'd done tonight, and she began to follow them silently.

The group of pirates still held the lantern with them, and Cassie mentally thanked that very fact as she carefully took the same path as they did. In her human form, she could barely see in the dark, and following them was easier when they were in plain sight than it would have been had they been submerged in the darkness the Isle had caused.

Cassie followed the bunch as they walked further towards the edges of the Isle, wrinkling her nose with slight displeasure as she began to realise just how popular the streets had become. She couldn't possibly force her way through the retiring crowd as they did; she'd just draw too much attention to herself that way, and she needed this task to go as smoothly as possible.

She gave a small huff and kept a close eye on the still-moving group, her head turning quickly as she looked for a way up and onto the top of the buildings. Following the group on the ground would be tough, but stalking them from up high would be easy.

When her gaze finally zeroed in on a rickety wooden ladder, Cassie's eyes practically lit up at the sight. She quickly rushed forward and jumped, gripping the bottom of the ladder and lifting her legs, tucking them into a higher step as she pulled herself up and onto the useful object. She quickly climbed up onto the roof, keeping close to the edge of the building to make sure she didn't lose the pirates.

Following them was relatively easy. The entirety of the Isle had been darkened, with only a few lights here and there illuminating the path. But the pirates were surrounded by the glow of the lantern and, much to Cassie's delight, were very loud as they walked. She couldn't understand how spray-painting one door could make someone so excited, but she also didn't care. Their obvious and audible happiness just made it that easier to track them, so who was she to complain?

As Cassie moved further away from her home and closer towards the edge of the Isle, her surroundings changed drastically. The air got colder—if that was even possible—and before long, an odd and displeasing odour filled her nostrils. She hadn't been this far out before in a long time, so it took her a little longer than she was proud to admit for her to realise that she was smelling the ocean.

With the harsh reminder that she was now in unfamiliar territory drilled into her mind, Cassie took great caution as she continued to follow the pirates. She focused more on the ground beneath her feet, making sure she stayed in the safe spots as she moved when it became clear that wood had been used for the majority of the buildings on this side of the Isle.

As they got closer to their home, the pirates got louder—if that was even possible. Where they'd been rather tense and aggressive further into the centre of the Isle, they were now filled with joy, a strange lightheartedness in the air when it hadn't been there before.

Cassie watched as the group strolled through a small marketplace of sorts, her wary gaze keeping watch as they stopped in the middle of the path.

The ocean was loud; she realised as she kneeled to better hear what was said. But anything they told each other was inaudible to her ears; the rushing of waves and creaking of wood were the only things to fill her ears at that moment.

Cassie stared down curiously as a tall pirate dressed in red and black separated from the group, taking the lantern with him as he walked in a direction opposite theirs. The others didn't seem to mind too much; they just carried on their way with a small nod to him, heading back to wherever they came.

She had every intention to go the same way as the group, knowing that when someone on the Isle was alone, they were a lot more likely to sense some kind of threat, and one pirate alone would easily manage to pin-point her if she wasn't careful, whereas a much larger group would ignore their warnings, falling back on the idea that there was safety in numbers.

However, as the taller pirate moved in a different direction, Cassie saw a glimmer of something in his left hand the moment the light touched it. She was surprised she hadn't seen it sooner, but they'd been moving rather quickly, and this particular pirate seemed to keep whatever it was close to his body. Either way, the young girl's interests had been greatly piqued at the sight, her attention leaving the loud group in favour of the tall pirate who'd left them to go do something else.

The pirate strutted away from his 'crew' and moved back in the direction they'd come, whistling a loud tune that Cassie didn't recognise. She balanced precariously on the questionable wooden beams she now relied on for support, praying with every fibre of her being that gravity didn't fail her. She'd come too far to lose now, and she was most certainly not leaving without her 'special thing'.

Cassie found out soon that this pirate was not, by any means, an idiot. Now and again he'd stop walking, his whistling dimming to nothing as he slowly moved his head around, making sure there was no one following him. When he did that, Cassie made sure to stay quiet, kneeling on the beam that held her until he started walking again. Surely he could feel her intense stare, and he wasn't being an idiot; she'd almost fumbled many times as he attempted to trick her. He continued to mix his actions, sometimes whistling but stopping to look around, or he'd stop making any noise and keep walking. It frustrated her immensely, and she just hoped he'd soon arrive at his destination.

Cassie's hopes were soon answered when the pirate slowed to a stop. He took a quick look around once again and turned to the right, crossing a small wooden bridge.

She quickly crouched down and held onto the beam, her brows raising as she drank in the sight of something she'd only ever heard of but never seen.

"Wow," she muttered quietly. She hadn't ever seen a pirate ship with her own eyes before, and even though this one was quite small in size, it still managed to surprise her.

The ship wasn't very clear, but there were a few small lanterns here and there that shed some light on deck. When Cassie saw the pirate disappear below the surface, she decided to take a small break and wait for him to leave. After all, she wasn't stupid enough to go running into a pirate ship with a pirate inside, especially after seeing how sharp their swords were. Once again, she had to wait, but she had a small feeling it would be worth it.

Her moment came when, not even five minutes later, the pirate came back out from below deck. He whistled again and moved away from the entrance, crossing the small bridge and heading in the same direction the others had gone. And only when his voice had faded, along with his footsteps, did Cassie move.

She held onto the beam and lowered herself to another, continuing the routine until her feet finally landed on solid ground. She took a glance at her surroundings and double-checked that no one was around. When she determined that she was, in fact, alone, she carried on towards the pirate ship.

Cassie hesitated as she stood at the end of the bridge, her gaze often returning to the rushing water only a small drop away. Even in her human form, she despised water, an odd trait she surely kept from being in her feline state for so long. Either way, she had no desire to fall in, and the water served as a harsh reminder of just how far she was from home. She couldn't take any risks out here; she had to be careful.

"C'mon girl," she urged herself, quickly turning away from the sight of the water when she became a little nauseous. She held her breath and moved quickly across the bridge, her anxiety heightening a little as she took in the scene around her. All she had to do was get in and get out as soon as possible, hopefully with her 'special thing'. But no 'special thing' was worth her life, and if push came to shove, she'd leave everything behind and go home.

Cassie ignored the slight awe she felt at actually being on a pirate ship and concentrated more on fulfilling the task she'd gone out of her way to complete.

She looked to her right and saw the entrance to the ship, the hallway leading down illuminated by numerous lights. She took a deep breath of reassurance and slipped down the small steps and into the hallway.

Cassie tried her luck with every door she could find. All seemed to be locked, and, much to her irritation, she was very close to calling it a day and going home. But when she twisted the doorknob of the very last room and it came open with a 'pop', she almost jumped and squealed with glee, though she resisted the urge to do just that and instead entered the room, gently closing the door behind her.

Cassie couldn't assume which pirate the room belonged to, though she took a quick guess that it was the one she'd followed. He'd been the last one to come in, and, for reasons unbeknownst to her, the lantern in his room hadn't been blown out. The thought that he'd be returning soon made Cassie move quicker. The utter dread she felt at knowing there was a risk of her being caught by a pirate ensured she kept her eyes from wandering to anything that didn't appear to be a 'special thing'.

Her dark eyes quickly closed in on the desk in the corner of the room. She quickly walked over and scrutinised the many objects laid out on the desk, disheartened to find only trinkets, maps, and other random things she had no desire to take. And for a moment, she wondered if this had all been a complete and utter waste of her time.

Until she saw it. Carefully hanging down from a hook messily hammered into the wall was a pretty, golden necklace of some sort. It wasn't like the other things on his desk, this one was so neatly hung up and meant more than all of the others. But the way it shone in the light had her so captivated, and she knew she had to have it.

Cassie took a step forward and held the necklace in her fingers. It was so smooth and clean, not like everything else on the Isle that was worn and dirtied. She furrowed her brows in confusion as a small and faint ticking came from the necklace, and her hands probed the object until she pushed down on the small button at the top.

The palm-sized and circular charm popped open, and Cassie smiled widely as she realised that it wasn't a necklace at all; It was a pocket watch.

A long time ago, before her father had lost his sanity completely, he used to tell her stories of the white rabbit he knew back in their homeland. A speedy, frantic little creature that was constantly obsessed with punctuality and who always carried a pocket watch around his neck to remind him of the time.

Cassie had many things in her growing pile back at Bargain Castle. Necklaces, rings, earrings, coins of gold and silver, and a few pretty gems here and there. But she didn't have a pocket watch.

Not until now, anyway.

Cassie removed the watch from its place on the hook and pulled the chain over her head. She gently gripped her hair at the nape of her neck and pulled, removing each long strand from underneath the chain until she was satisfied. She didn't have any pockets on her dress, so taking things had always been a rather small nuisance, but this very special thing fell comfortably around her neck, the watch itself resting against the space above her belly button.

"Well, well, well," a deep and mocking voice sang from behind Cassie. She jumped high and turned swiftly, the familiar nausea returning as she found herself facing the very pirate she'd followed almost all night. "Hello, kitty, kitty."

'Oh shit.'

AN;

So, that's the end of this chapter. Quite uneventful and short, so for that, I'm sorry. But the first chapter is always to introduce you to the OC's personality and whatnot.

If you have any questions, please feel free to PM me or leave a review, feedback is always appreciated. But please no flames.

Thank you for reading!