Hard to believe how far back I started this but I'm seeing it through to the end at least. This motive for this prompt actually came the easiest to think of considering the discourse over Kaito's hatedom hyper exaggerates some of kaito's negative traits to kingdom come. One specific reason is dialogue that was said in the Jap dub between him and Kiyo. So in a weird way I kind of have to thank them I guess? There's a form of irony in there but I can't pin point what kind. Anyways lets all sit down and make an astronaut cross dress which he's actually hinted at doing in-game by the way in chapter 2 but the hatedom isn't ready for that talk.
pupupupupupupupupupuppupppupupupupupupupupupupuppupuppupupuppupuppupupupuppupupupuppupupupuppupppupuppuppupuppupupupppupupupup

"That is very fragile please stop shifting it."

It felts like the seven hundredth time to this week that Korekiyo shinguji had to say that to someone while trying not to shout. He liked to think of himself as a person of high patience. Ever since he stepped into Hope's peak however, it dawned on him just how limited his patience bar truly was. Not that he honestly minded to much mind you. Humanity and all its sides from the good, bad, and the things in-between was what he enjoyed witnessing. This didn't mean he wasn't aloud to be annoyed at times like anyone else.

Currently he had been granted the rare chance to put on a play set in Kabuki style wardrobe and story telling. There was a chance to mix a bit of a traditional with a few modern elements of story telling that he was extremely eager to have done. The people he had helping were a bit clumsy though. Those few people that were interested enough to audition weren't ultimate actors or actresses by any stretch of the imagination either but they would have to do.

"HEY KIYO CHECK TH-" *thud*

The familiar voice of a friend who spoke far to loud being indoors broke his thoughts. The noise that cut off Kaito's yelling hopefully didn't mean that he broke something on his person. Again.

"I'm okay! I didn't rip the outfit and I am okay."Kaito assured to those within earshot. While seeing for himself that the assigned outfit was okay, Kiyo was not impressed with the make up job. That and it looked like he tied the long ends of the robe to look more like pants without asking.

"What exactly were you doing up there and why are only your eyebrows done? I also know you pretended not to sleep during my lecture on the history of the outfit your wearing but the picture sheets I handed out should of stuck." Kiyo asked with a raised eyebrow.

"I know, I know, I just thought since you said you wanted to give it a more modern less sissy school look I added my own touches." Kaito said confidently. When he saw the unimpressed look Kiyo was giving him all he could do was shrug. "What? You didn't really clarify what "modern touch" meant so I thought that could mean like a modern rock hero look. I thought it was cool at the time."

"I have many questions on what exact rock star from anywhere your trying to copy but more so on how you thought it related to drama story themes. Regardless I'm going to have to redo those clothes now." Korekiyo being the expert in knots that he was, had little trouble untangling the mess Kaito made of his makeshift pants. As he grabbed an emergency make up kit for his face foundation something made him pause in thought.

"You know, it isn't lost on me that history and cultural stories that go with them aren't everyone's cup of tea. I also know that my stories aren't something you like hearing when they are unpleasant or about something supernatural things. Don't give me that look I know you aren't just "getting the flu" when I bring up the cult legacies. Even so I'd think you'd be a bit more mindful on what things mean to people kaito, no matter your beliefs on the matter. I'm not forcing you into this role but if you don't plan to take it or its history serious because of your prejudices to the traditions then you are free to leave at any time." Explained the anthropologist.

"Wait what?! I love history dude and I wouldn't be here if I didn't find it interesting. The luminary of the stars is my number one dream but actor has kind of been right behind it as a kid so I want to give it my all. What do ya mean by prejudices by the way? I'm not biased to your style but my dad might see this and the last thing I need is him questioning why a boy is wearing make up even in a play. Its just the way he is."

While reading Kiyo's expression was hard at times because of the mask it was clear that he was looking at kaito with a mix of amusement and annoyance. Kiyo signaled with his fingers for the other boy to stay still as he applied the first layer.

"If you really enjoy history Kaito then you should know that make up use to be primarily worn by men in the past. Not just in the sense of war paint which I'm going to assume you were going for since that's an influence to at least a few 80s groups I know of. Its was and still is a symbolic thing for Japanese men today but society from outside religions from here have made mock of these traditions in labeling things like lacey material and make up. Not only is it an insult to your own history to say they are "sissy" but if I were to guess you got that word from your parents then it makes you prejudice as well. You do know what that term means correct?"

To his credit it seemed like he was trying to think before he spoke this time and waited until Kiyo put his brush down before answering.

"Eh, I didn't really know that besides the war paint part. Are you saying that word doesn't just mean a guy who's goofy and girly then? My dad use to say it a lot when we'd watch the olympics." Kaito finally replied.

"No, it's an old but still somewhat common term hate slur against gay men though. Considering some of our classmates are in same sex relationships I'm surprised you use the term that casually if you knew what it meant."

"Really?! I mean my old man use to use it whenever we'd watch the Olympics or any sports games together. It was usually whenever the dudes would cry on one another or just had multicolor hair. Always thought it was weird since it was usually while watching what he himself called the manliest of sports to. Damn, I'm sorry about that. That does explain the weird looks Miu gave me once when I said it in front of her and tenko. I'll have to find a way to apologize later." Kaito started to move his palm up to his neck to rub at it out of habit before realizing he had some make up there already.

They walked to the changing room as they talked for a bit more privacy.

"It's quite fine, the meaning of many words today have been changed or forgotten overtime either for better or worse. You should probably do some research in your free time though just in case any other terms you've picked up from you parents slip one day. While we are on the topic of dated and changing things, Japan is rather stagnant on what masculinity means over the years in some locations more then others. It can mean whatever you personally want to make it for most people though. Limiting to things like having to wear pants or scary paint jobs is fairly limiting. You weren't raised in this area correct? Its possible the traditions of your family came from one of the more bias cultures in that location."

As Kiyo spoke he began adding a bit of the red lining around kaito's nose, jawline and eyelids. There seemed to be some kind of internal fight going on in his eyes if the mixed look of guilt and frustration was to go by. Once again Kiyo gave a two fingered gesture to speak when he was done. Stubbornness, ignorance, and bias were human nature which wasn't something new that Kiyo didn't see everyday. Despite seeing this in Kaito like many other people he never got a feeling of malice or true hatred from him. If korekiyo really thought kaito's ignorance was that high and built on one of those houses he'd of ignored him the week after meeting for the first time in class.

Since kaito didn't speak about his home life often other then how good his grandparents baking was, this felt like a rare sharing moment he was getting. There were only so many things you can tell about a person who was an otherwise unapologetically open book about himself.

"Nah, we lived slightly close to the city for my mom's job but like one the outskirts a bit. We live a bit closer now that I'm coming here but still a pretty long train ride away. Your right about my dad though. I love him but some of the things I've had to fight him over letting me do cause they might not be "manly" can get exhausting to be honest. I know he can only have as much control as I let him but...there's just not a lot I can do other then nod along so I can get by." Explained the trainee.

While Kiyo knew there wasn't much he could do for Kaito's home life there did seem like a trick he could try with making him less awkward. When finally finding the right lipstick, he turned it around in offering as kaito was now facing a mirror.
"I originally meant for the hero of this to be woman you know. The right kinds of make-up and clothing could make you to unrecognizable to make anyone upset. You'd have to give up having your name mentioned in the after credits though. Its your choice if you want it to be."

The look of shock on Kaito's face was a little more comical with how big the eyeline make-up made his eyes look. Still his smile was that of appreciation as he took the lipstick with a nod and smile.

upupupupuppupupuppppupupupupupupupupupuppupupuppupupupupupupupuppupupupuppppuuupppupupupupupupuppupupupuppuppuuupppuppupup
With this done I don't know if I'll put this on hiatus for a but or keep going. I'm pretty inconsistent with things but have been trying to get a bit better with it over the years.