From Trainer to Beast Tamer Pokémon Trainer! Reader x Twisted Wonderland

Special Event: Tsum-Mania Vice Dorm Leaders

It's up for the Vice Dorm Leaders (And Ruggie since he's practically that)! I own nothing.
Special: Tsum Mania With Vice Dorm Leaders (And Ruggie)

Usually when some massive catastrophe happened on Night Raven College, it had the decency to occur during the day (the Ghost Groom fiasco notwithstanding), but as (Y/N) came to realize, Twisted Wonderland would continue to find ways to drive her bonkers. After managing to wrangle the baby Pokémon to bed after having a particularly powerful bout of zoomies, the Pokémon trainer was heading upstairs to turn in early when she heard rumbling from the sky that shook the dorm.
"What in Arceus's name!?" She growled, running out the front door.
There was a flash of bright light as a portal cleaved through the sky, and small shadowy figures began to float down in a burst of sparkles. Hearing a crash from inside followed by the squeals of the baby, (Y/N) gripped her nose and sighed.
"This is tomorrow's problem."

Trey

Crowley was kind enough to send her a text explaining what was going on. Apparently Twisted Wonderland loved playing host to travelers from beyond their world, because now the school grounds were filled with little pillow-like creatures called Tsums...who inexplicably looked like her friends. (Y/N) was not about to call into question cosmic level coincidence of that, she was fairly certain there were a few versions of herself running around the universe somewhere, and just resolved to take a look at the newcomers and see if she could help. Naturally, Heartslabyul was her first stop, and she brought a few choice Pokémon to help make the rounds. The scent of baked goods hit her like a truck the moment she set foot in the lounge and Alcremie decided to let herself out of her ball, making a break for the kitchen. Following, (Y/N) was not surprised to find Trey at his usual station, though the amount of sweets was a shocker.
"Hey, Trey!" She greeted, making the green haired male turn and smile.
"Hey, (Y/N)." He returned, immediately kneeling down to pet Alcremie's head. "What brings you here?"
"You know the crow. If something weird happens, I'm the one expected to deal with it. Though, I don't think excessive sweets coming out of this kitchen is what he had in mind. Did I overlook another Heartslabyul event? I thought I was getting better at that."
"No, no, you've been doing great." Trey assured, rubbing his neck. "I just...this is the only way to get them to stay in one place."
The pair turned to see a tiny creature working diligently on a cake. Despite having nubs for hands, it was shockingly dexterous, and like the headmaster had mentioned, it looked like a mini Trey, right down to the outfit.
"Aw! Look at him!" (Y/N) squealed, running up close to admire the Tsum. "He's a mini you, Trey! He even had mini glasses! Hi there, little guy!"
The Tsum halted its progress to wave politely at the girl as Alcremie made her way over with Trey.
"Yeah, it's been a big help around the dorm, though, these Tsums are way quicker than you think." Trey explained as he helped Alcremie on to the counter. "I figured it would be easier to keep an eye on them while making some treats. They've been a big help."
(Y/N) smiled. "Guess they also take after a certain someone's hard worker attitude."
He blushed. "Hey, knock that off."
Tsum Trey stared at Alcremie, who waved a greeting, before zipping off to another part of the table, returning with a bit of wax parchment on its head. It made a motion to the fairy type which stumped the humans, but to her credit, Alcremie was able to figure it out, making a decorative swirl on top of the parchment. The Tsum then bounded up the cake, somehow leaving the frosting undisturbed, and slipped it on top. It leapt for joy, jumped down to make happy circles around Alcremie.
"Not bad." Trey told his counterpart. "Seems like I could learn a lot from you. You guys wanna try some desserts?"
(Y/N) looked extra pumped. "Like you need to ask!"
"Creamie!"

Ruggie

(Y/N) was munching on some of the cookies Trey and Tsum Trey were happy to send her off with (with the stipulation she brush her teeth when she was done with her rounds). Of course, the scent was all too tempting for a small, shadowy figure that sneakily entered her bag as she walked. Unfortunately for it, it had the misfortune of tapping a certain Pokeball, letting out Typhlosion, who immediately stopped his trainer and fished out the offending Tsum. (Y/N) held Tsum Ruggie in the palms of her hands as it clung to a cookie, smiling.
"Well, well, looks like someone was hungry."
The Tsum made puppy eyes as its beastman counterpart came running in.
"Hey, (Y/N)! You managed to catch it! Man, that Tsum has been causing nothing but problems today!"
The Tsum let out angry squeaks at having been thrown under the bus, but (Y/N) was sharp enough to not take Ruggie entirely at his words.
"I see. Well, I don't see a problem sharing sweets, IF I'm asked politely. That seem fair, little one?" The Tsum nodded eagerly, holding out the cookie and motioning towards it. "Okay, go ahead."
The tiny creature seemed to inhale the cookie, unsurprising since the Tsum didn't have a visible mouth. The Pokémon trainer didn't question it as she turned to Ruggie, who seemed to be pouting.
"You want one too, Ruggie?"
He perked up immediately, grinning. "Well, if you're offering!"
They laughed as (Y/N) fished out the remaining cookies from her bag and headed them to the hyena, who began to scarf them down. His Tsum counterpart leapt at him, also seeming to demand a fair share, which Typhlosion had to parcel out. In a few minutes, only crumbs remained, which Ruggie was already licking from his lips.
"Shishishi! Your generosity never fails to fill my belly, (Y/N)!"
"Well, it's Trey and his Tsum you really should be thanking. Now, Ruggie, getting back to all this 'trouble' you mentioned your Tsum getting into, he would happen to be rummaging around other people's bags, would he?"
Ruggie's ears went flat as he suddenly felt the girl looming over him. "Um...no?"
"Then you'll have no problem turning out your pockets to prove it? Typhlosion would be happy to help."
The fire type banged his fists together with a dead stare. With a gulp, the hyena took off, leaving his betrayed partner in crime to be handled by Typhlosion as (Y/N) ran after him.