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

Special Event: Glorious Masquerade

Sooo....long....
All joking aside, you all were really excited for this event. May the RNG gods have mercy upon us all when it finally releases over here. Also, colds suck!
I own nothing.

Somewhere beyond Night Raven College, a short boy stood in a shadowy room, staring into the swirling flames of a fireplace.
"Just a bit more..." He muttered. "We're almost there. Just a little more, and I shall be rid of those dastardly bugs. Only then will we be truly free. I will bring peace back with my own hands!"
He began laughing maniacally as a knock came at the door as a student walked in.
"Excuse me. The Night Raven College students have arrived. Let's go and welcome them."
The other one's laughter was cut short as he cleared his throat.
"Ahem. Of course. Hmph, why oh why is everyone in such a cheerful spirit? Nevermind. I truly am looking forward to meeting him." His fists clenched as he reached for the door. "Just you wait...Malleus Draconia!"

(Several Days Earlier)

A swarm of Night Raven students were packed into an unsuspecting classroom like sardines, muttering and moaning about being woken up so early.
"Sheesh!" Grim whined as he was laying on Houndoom's back. "Headmaster's got us all out here so early in the morning! What's he mean by 'something important'?"
"Nothing good if I had to guess." (Y/N) said, prepared to hear Crowley beg to be bailed out of a mess again.
Ace sighed. "Yeah, probably. Every year level is present. Nothing good usually happens whenever he calls for gatherings like this."
"Quiet!" Deuce warned as the door opened. "He's here."
The headmaster sauntered to the front of the class, causing the students to quiet down slowly. His grin only further made the Pokémon Trainer mistrusting.
"Hello, everyone! Good morning! It seems we've been blessed with wonderful weather today. Truly marvelous!"
Grim shook his head. "Oh, man. He's grinning like a madman already."
"Doom..." The Dark Pokemon muttered in agreement.
"I have some good news for everyone." Crowley announced. "It has been decided that we will be participating in the Mage Development Training and Cultural Exchange in a month's time!.
"Cultural exchange!?" Everyone repeated.
Riddle, who was at the front of the class, raised his hand. "A cultural exchange between schools? How is it any different from our previous cultural festival?"
Kalim, who was sitting next to him, beamed. "Will we get to make new friends? Now that sounds like fun!"
"Your attention, please!" The headmaster called. "Now this cultural exchange, rightfully dubbed, 'The Inaugural Gathering of Prospective Mages' came to be after a certain school's proposal. Are you familiar with Noble Bell College from the City of Flowers? Noble Bell College will be hosting said cultural exchange."
"City of Flowers?" Vil said, as if testing the name on his tongue. "Yes, I've heard of it. It's quite well known in the Shaftlands."
Lilia descended from on high right behind the blonde. "Indeed!"
Vil, of course, nearly had a heart attack. "Oh, my goodness...! I wish you wouldn't sneak up on me like that!"
"The City of Flowers is quite an historic place." The fae explained, ignoring his victim. "Yes. Noble Bell College may not be as huge as Night Raven College, but it has got quite the history. However, I myself have not stepped foot inside of it. We have been blessed with quite the opportunity, indeed."
The crow nodded. "It is as Vanrouge says! Similar to our school, Noble Bell College is off-limits to outsiders, save for special occasions. Now, imagine my surprise when such a college suggested hosting a number of prospective mages. I was worried that our prestigious school was being treated like a common college, so I thought of refusing at first, however, 'Who else but Night Raven College could produce such talented young mages? Please do consider!' Well, how could I refuse after such a spiel? How could I say no when they praised me for my wonderful upbringing!"
"You mean you were afraid that we would be overlooked as a school of delinquents and crazy people led by a morally bankrupt crow." (Y/N) snarked.
Cater rubbed his head, unable to disagree. "Yeah, headmaster is an easy fellow. No wonder he's in such a good mood."
"Hah." Leona huffed. "Who in their right mind would join an annoying field trip?
Idia's phone proxy was practically flipping about the table. "This is the worst of the worst! Yeah, the word 'exchange' is already a hard pass."
Sebek, as per usual, stuck up his nose. "There is nothing that their students can teach our Young Master. This is a pointless excursion!"
"You all are just proving my point!" The Pokémon trainer called out. "Still, what do you think, Grim? You up for a field trip?"
The cat monster tilted his head. "Hmmm... I don't care about that at all, yanno. It's a small school, right? I bet it's plain and boring, too."
That finally caught Crowley's attention. "My, my. What are you saying? A cultural exchange means you get to talk with other students. It is not a difficult task. After the exchange will be the masquerade ball. You can dance, eat, and socialize as much as you like! As a student of the prestigious Night Raven College, imagine yourself in a place where mages-in-training all over the world have come to gather...'Amazing!' 'You're my idol!' 'Please give me your autograph!' People will fawn over you!
Grim gulped. "F-for real...!?"
"Will you stop feeding his ego!" (Y/N) yelled. "It's hard enough to keep him grounded without your interference! If you want me to babysit the field trip students, just man and ask like an adult!"
The headmaster cleared his throat, dodging her challenge. "More importantly, this is a special time for the City of Flowers."
"Special how?" Grim asked.
"They will be hosting their annual festival soon. Beautiful decorations, breath-taking performances, souvenirs unlike any other, delicious food. You'll get to enjoy all of that for three days and two nights!
Grim immediately began hopping, promptly getting him kicked off of Houndoom. "I WANNA GO!!! Pick me, pick me! I wanna go to the Bell-whatever! I wanna eat good food!"
"If it's free, then I'm all in, too." Ruggie volunteered.
Azul had his usual scheming smile on his face. "Getting to know prospective big shots is a good opportunity for me as well."
(Y/N) gave him a disappointing look. "Of course that's where your mind goes."
"Indeed. This is a good learning opportunity, Malleus. I suggest..." Lilia trailed off, noting the tall fae was not in fact in the room. "Hm? Where is he?"
Silver stood up. "Maybe he hasn't seen the announcement yet? I'll go look for him quickly."
(Y/N) sighed as he left, before putting on a smile. "Well, this does sound fun."
Ace nodded in agreement. "All right! Let's go get packin'!"
"Ah, not everyone can go." The headmaster informed, causing everyone to cry out.
"WHAT!?"
"The cultural exchange occurs on Halloween. Our school is also hosting a Halloween event, so we can't leave the place empty now, can we? I will be choosing only ten people to participate in this exchange."
Epel shot him a dirty look. "Wow, way to build everyone's hopes up"
"What will be your criteria for choosing, if I may be so bold?" Rook asked as Crowley held up his hands.
"Of course, I will be deciding using the fairest of means."
Trey tilted his head. "That being? If I were to guess, it must be a strict screening based on overall grades, personality, and behavior..."
"By drawing lots!"
Grim crossed his arms. "You just wanna have fun, dontcha!?"
"Five madol it's rigged." (Y/N) whispered to Ace, who shook her hand, discreetly.
"You're on."