Twisted Wonderland Scenarios

Asking them to wear a dress/skirt

Heartslabyul
Riddle
Excuse me, have you seen that outfit? The only questions he needs to ask is about your suggestions.
He doesn't have them in his regular wardrobe, and he probably wouldn't buy them off of his own accord, but if you suggested it first, he'd indulge.
He eventually decides on a black pleated skirt with a bright red petticoat.
Tell him he looks nice, he's already fairly uncomfortable.
"How does it look?... No, I do not look cute!"

Trey
He choked on his rule approved drink, before adjusting his hat and staring at you.
"I'm sorry come again?"
Unfortunately, skirts aren't really his thing.

Cater
He already owns three. He was surprised you hadn't seen them yet. He got up, and ran away. You saw him bolt down the hallway, vanish behind his door, and emerge after two or so minutes in a jean skirt.
"Whaddya think? Last time I wore this I got mad likes on Magicam~"
He also revealed that it used to be his sister's. Not like he minds the hand-me-downs., they're vintage!

Ace
He froze. For a moment, it seemed like you broke him. After sitting in silence for a moment, he finally spoke.
"Can you say that again."
And so you asked again. Would he ever wear a dress. He said no.

Deuce
He choked on... something. You weren't certain what it was. He smiled anxiously, asking for clarification. You restated the question, and he mumbled an answer you couldn't quiet hear.
Eventually, he took you up on your question... request? Offer?
Whatever it was, he offered to give a dress a try. He doesn't own any though and he's too insecure to buy one himself.
Eventually, you got your hands on a dress that would fit him.
"How does it look?... don't laugh at me please."

Scarabia
Kalim
His friend wanted him to wear a skirt. He was doing something for his friend. That was the logic.
He saw himself in the mirror, and thought it looked cute enough for a confidence boost. You nearly choked when he walked into class in a deep red skirt.
"Good morning! What do you think? I really really like it!"

Jamil
"... no."
He does not.

Octavinelle
Floyd
When you asked him, he simply said he'd consider it. The topic was dropped there.
Then he actually thought about it. A skirt seemed like it'd be less effort than pants. Plus it'd be like his true form, and that was a bit of comfort. He now wears them regularly.
"Jade says it looks ridiculous, but I enjoy it. What about you?"

Jade
His face turned bright red, covered his hat with his face, and walked away.
Yes, he walked into many walls.

Azul
Don't even ask him. The minute the word "skirt" left your mouth, he gave you the look. The same one Jade gets when he mentions Azul's childhood. The same one Floyd gets when he does... anything.
"What were you about to say."

Diasomnia
Sebek
You never saw him so quiet. He froze. You definitely broke him.
After a minute, he stood up, pat your head, and gave you an awkward look.
"They look better on you. As far as anyone needs to know, this conversation did not happen."

Silver
He was genuinely shocked when you asked, and politely declined.

Lilia
He cocked his head.
"Is this because I look like a woman?"
You clarified that it was not. He considers it, but you haven't seen him in one yet.

Malleus
"You are... certainly a strange one."
But he considered it.
Congratulations. You've seen Malleus Draconia in a black and silver evening gown.

Pomefiore
They do. On a regular basis. Have you met a Pomefiore?

Savanaclaw
Leona
"You interrupted my nap for this?"
If you want him in a skirt, talk to Ruggie about getting one.
Ruggie laughed at you.
Unfortunately, Leona will not be in a skirt.

Ruggie
Ruggie Bucchi already owns a skirt.
Granted, it does not fit him, but he owns one.

Jack
"..."
He got up and walked away. You swore you saw him blushing.

Ignihyde
Ortho
He seemed confused.
But he gave it a try.
It wasn't his thing.

Idia
"Wh-Wh-Wh-What???!??!"
He had to go back to his room for a moment.
"A moment" was actually a week. People are concerned for his well-being. Shame.