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

Special Event: Tsum-Mania Dorm Leaders

Yup, these little menaces get their own batches of chapters to fill in the gaps. Since everyone has gotten a Tsum at this point, we're breaking these little side stories down into dorm leaders, vices, then everyone else. Comment what kind of interactions you want for the tsums.
Special: Tsum-Mania With Dorm Leaders

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."

Riddle

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 made certain to bring Shaymin along with her. Peaking into the rose garden, she spotted Riddle having his usual tea, albeit with a few more sweets.
"Riddle!" (Y/N) greeted as Shaymin bounded from Swampert's head to paw at the red head's chair.
Riddle smiled, scooping Shaymin into his lap. "Good day, (Y/N)."
She walked over to join him, only for a small form to scuttle along the table to the edge. Just as Crowley described, it was a round, plush version of Riddle, dorm regalia and all, with a set of adorably stubby limbs. Despite this, the little one rose up, pawing towards the girl, who smiled.
"Oh, hi there, little one!" She reached out and allowed the Tsum to rest against the palms of her hands, which made it squeak happily. "So you're one of the Tsums I've heard about. Oh, you're so cute!"
The Tsum hopped happily, climbing up the girl's arms before resting against her neck and nuzzle into her cheek. Riddle blushed at the sight, setting Shaymin onto the table as he cleared his throat.
"I would warn you, it's a bit violent."
"What, this little guy? How can you possibly call that face violent."
"It tackles any student caught breaking rules."
(Y/N) blinked before chuckling. "Well, it's a good thing I'm not a rule breaker."
The Tsum nodded in agreement before bounding off its perch, off Swampert's head, and back onto the table. Shaymin sniffed curiously at it before initiating a play bow. The Tsum wriggled, already on its belly, before pouncing towards the mythical. The pair zoomed across the table as the two dorm leaders shared a cup of tea.
"Despite my...apprehension at being compared to the Tsum, it certainly shares my affinity for Shaymin." Riddle admitted before taking a cookie. "And sweets."
(Y/N) chuckled. "Well, it's kinda hard not to like either of those things in my opinion. Besides, you can just pretend every compliment the Tsum gets is for you."
Just as she said this, Shaymin and the Tsum suddenly rolled over towards them, knocking over the teapot and spilling tea everywhere. The pair immediately jumped up, but too little, too late as every was splashed. Contrasting his fondness a second ago, Riddle gritted his teeth and had an irk mark on his temple.
"Though I do detest how mischievous my counterpart has proven to be."
(Y/N) merely scooped up Shaymin and Tsum, both clearly uncomfortable and trying to shake off the tea.
"You know, if your Tsum is like this, I don't even want to know how chaotic Ace and Deuce's are...and Arceus, what is Tsum Floyd like!?"
The red head merely sighed. "Why do you think I've been hiding in the garden all day?"