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It was movie night, but Black Hat wanted no part of it. In fact, he had other plans in mind. For the past several days Black Hat just wanted to feel pretty, and this was the perfect time to do it, while his bafoon-for-minions were distracted. Black Hat opened a portal to a pocket dimension, where he stored the other half of his wardrobe. It had to be in its own pocket dimension because he's had employees like Demencia breaking into his closet for centuries.
Did he feel like the glittery red dress, or the china poblana dress? He could put on the latter and perform his favorite hat dance, but he didn't feel like it doing it by himself at the moment, so he didn't pick that dress. Instead he grabbed a long black dress that flowed out at the bottom. Ah screw it, he grabbed a red feather boa and a fedora hat with a feather just as red. And a corset too while he was at it.
Black Hat took off his suit and trenchcoat and tossed them to the side. He then put on his corset, tightening it as far as it would go and bending at impossible angles to do so. Next he slid on the dress, but then he stopped for a moment to admire himself in the mirror. He really was quite fetching. He traded his signature top hat for the fedora, treating the top hat with much more care than his discarded clothes. The scarf he would put to the side for now.
Black Hat sat himself down on the bench before his vanity. Unlocking the drawers with his powers, Black Hat carefully selected which of his make-up he'd be applying tonight. Black Hat would keep his make-up on his pocket dimension with the dresses, but everytime he did they would go missing, never to be seen again. Which really irked him because his make-up wasn't cheap. Not that he didn't just steal it in the first place anyway.
Black Hat carefully lay down a coat of black lipstick, brushed on some dark purple eyeshadow, and penciled in his eyeliner, a millennia of experience bearing its fruit. But as Black Hat was applying the mascara, the worst case scenario happened. Demencia came loudly barging into his room, completely disregarding the locked door. Black Hat panicked, he tried to quickly wipe off his make-up, as if that alone would get rid of the evidence, and he only succeeded in smearing his make-up anyway. Demencia's strut came to a halt the moment she laid eyes on him. Black Hat felt his face flush from embarrassment.
"Well you look pretty." That... wasn't the reaction Black Hat had been expecting.
"You really think so?" This had slipped out before Black Hat had a chance to think about what he was saying. He was absolutely mortified at this point. Seeking validation from someone who could barely think straight. He should be yelling at her, no wait, making up some sort of excuse. He opened his mouth to speak but realized that he couldn't find any words to say. He felt too hot, his corset too restricting.
"I mean, yeah, duh. You look hot in any outfit. And let me tell you are rocking that dress. Say, why don't you dress like this more often bonbon?"
"I... have always presented myself as a man. As such it would not be proper to go around wearing a dress."
"Pfft. Are you really that concerned about what other people think? You're Black Hat! You do whatever you want whenever you want. You like wearing dresses? Then wear dresses it's that simple."
"You're right, I am Black Hat. Er, thank you. I suppose I needed to hear those words more than I thought. If you like I could do your make-up for you as a token of my gratitude."
"Ooo, we could have a girl's night out!" Demencia squealed with joy. Black Hat nearly had to cover his ears.
"Don't call it that." Black Hat grumbled like the old man that he was. Then he had an idea. "You wouldn't know how to perform a hat dance, would you? I could lend you my china poblana dress."
"Black Hat, are you flirting with me?" Demencia bat her eyelashes at him.
"Of course not, I just happen to like the dance. Now sit here and sit still." He sat Demencia down on the bench and once again opened up the vanity drawers. Most of his make-up was black or some other dark color, but for some reason there was a tube of a bright green lipstick that had been there for years. Black Hat honestly couldn't remember how it got there in the first place. But Black Hat was sure that the color would suit Demencia, in fact it might have very well been Demencia's once. Perhaps she dropped it.
"It's 'cause it has to do with hats, doesn't it." Demencia's talking was making her whole face move, which in turn made trying to apply the aforementioned lipstick more difficult than it needed to be.
"Maybe. Do you want this done or not? Stop moving." Black Hat brushed on a maroon eyeshadow. A darker, more natural color to balance out the green.
"You know, I never could open these drawers." Black Hat really wished she would stop talking, he nearly messed up with her eyeliner and almost stabbed her in the eye instead.
"That was the point. Talking is moving, shut up or I won't be able to finish your make-up."
Black Hat worked on some finishing touches to Demencia's make-up, recreated the portal to his pocket dimension, and then grabbed and threw the china poblana dress at Demencia, who caught it. He then hastily fixed his own make-up as Demencia worked on switching clothes. Once they were both done, Black Hat turned to Demencia. She was very pretty, as was he. He took Demencia's hand and they proceeded to dance the night away.