Day 6 of x Reader Week.
Design wise, I LOVE Chisaki. The stuff he's done, not so much. There's very few anime villains out there where I Iove their design cause most of the time their designs are either too cringy, stupid, or too 'over the top'/busy. It says alot if Chisaki and Dabi are in my top 5 alongside Rob Lucci from One Piece, Lunatic from Tiger & Bunny & Chrollo Lucifer from Hunter x Hunter.

You’ll never forget the day you met Kai Chisaki. Although, he kept stressing how badly he didn’t want to go by that name, you still call him Chisaki just because. It was quite an eventful day that happened many weeks ago. Tomura Shigaraki, your leader, had set up a meeting with the Yakuza. Chisaki wanted to speak of a potential partnership between both of their infamous organizations even though Shigaraki made his point clear beforehand that he had no interest in a partnership. Still, you can’t go wrong and at least hear the man out right? You were chosen as Tomura’s one and only guest, and that’s how it all began.

Chisaki paid you no mind at the meeting except for the very beginning as introductions were exchanged. The rest of the meeting consisted of bickering, potential agreements and a poor attempt on Chisaki’s end as he tried to play a board game. Only to just sit back with his fingers intertwined in one another as he heard your leader out. Such a boring meeting, everything went on as expected. Of course Chisaki and Tomura disagreed on much, in fact, you’re sure they didn’t agree on a single thing. Although, you’re not very sure how, somehow Chisaki got to Tomura and he got on board. A partnership was created between the two organizations as long as Tomura gave Chisaki a few of his trusted disciples. Immediately, your name was thrown onto the table with a large mix of League members names along with Toga, Twice and Kurogiri. It was disgusting how you’re being thought of as an item to be won. These boys ought to be lucky if you don’t straight up ditch them both.

“Kurogiri and (Y/n) aren’t for negotiation,” Tomura lied down his boundaries quick and made his point clear. You’re surprised with his stand to keep you and Tomura must’ve surprised his own self as well. You could very well tell the tension was too much for him with the way his hand was shaking horribly in restraint to scratch his neck.

Chisaki finally paid you some valuable attention as his hand adverted to your direction. “What if she wants to be one of us? You gonna keep her then?”

“That’s her choice and I know she doesn’t...” Tomura’s crimson gaze narrowed in on the boy across from him.

“Hmmm… Let’s see what she says,” Chisaki hummed.

Of course, everyone within the room began to stare at you longingly for a response as you sat beside your Leader. You sighed, “I’m only gonna say this once… Keep treating me like a prize to be won and nobody will get me.”

“Point made,” Chisaki shrugged and continued to argue with Tomura over who will be the new members of the Hassaikai. Thankfully, you were dropped from the argument for good and joined in with two of Chisaki’s Hassaikai members, Chrono and Mimic, for a cup of tea. Mimic was on edge the entire time and death stared your leader. Then again, you were too. After long deliberation, Tomura had agreed to let Twice and Toga go which was sad. You’ve came to like Twice enough that you hang around with him outside of the League. That meant it was time to leave, but before you could, Chisaki separated you from the pack to share a few words of his own.

Chisaki’s amber eyes bored into your own. They were curious yet also tired with annoyance. “May I ask your reasons for following that childish man?” Chisaki questioned your motives as to him you were a woman with great potential and that’s saying numbers when there’s not a single woman in his gang.

“I hate heroes,” you shrugged and purposely held out on details. “Why ya askin? I thought I told you I’m not a woman to be bought!”

“Don’t play hard to get,” Chisaki instructed as his voice was airy within his mask. “I figured you’d be better off under my command. Unless you like the lack of respect as Tomura only holds onto you for your strength.”

“You’re not wrong,” you admit without a thought. “I have no room to talk since I too am only using Tomura for personal gain. I’m doing whatever I can to keep myself out of harm's way. I didn’t choose the villain life after all.”

“I know who you are,” Chisaki recalled a story on the news and newsprint with your face all over it inked in black and white. “Your husband to be was a serial killer. His profile wasn’t as high as Stain but he came pretty close,” You got the chills just listening to Chisaki speak of you as if he knew your entire history. “Once caught, he put the blame on you to take you down to hell with him. He only wanted to marry you as to have someone to pin all the crimes and to run a free man. Such a pity… If you join me, I can clear your name in no time,” Chisaki’s skills of persuasion was scary. That offer is one you’d jump at...

“No,” you began to walk away. “I’ve spoken with a few of your members today… It sounds like you don’t give a damn about most of them. I won’t be one of your pawns alright… Not again. That’s why I’ve locked up my heart.”

“If your mind’s made up, it’s made up. I just find it funny that you’re Tomura’s right hand and he refuses to explain why. That must mean you’re special,” Chisaki hummed with his minor compliment. “This won’t be the last you’ll hear from me.”

“Take my number then,” you flashed the man one of your personal cards from back when you used to be a free woman and was close to opening up a company of your own. “Admittedly, I’d love to hear from you again. I’ve never seen a man try so hard to win me over like this in such a long time.”

“Oh trust me… I’ll win you over.”

From that day on, Chisaki made his point clear that he wanted you on his side. You’re not entirely sure how he learned of your address, let alone the alias you went by. He sent you letters as well as crimson roses as gifts. The letters outlined the subject about the next time you two would meet again, even set up times you can drop by his base or times he’d be available to meet up with you.

“I thought this man said he wanted me on his team,” you picked up a rose carefully only to figure out that it was trimmed as no thorns were present. Such a deep crimson, like blood. “Now he’s sending me flowers. Roses are my weakness…” It was such a foreign feeling as your lips began to curl upwards. “Even my fiance never got me flowers… I’ll… I’ll give Chisaki a chance.” You sat down the lone rose you had picked from it’s extravagant bouquet as you went to give this man a call. You had neglected to notice a note that dangled from the bouquet of roses.

I’ll be the man who treats you right. I will and can mend your broken heart.