(I had a tad bit of asssistence from Chat GPT on what to do with these two and it did help a little on what to have their conflict be. This ship was requested by I_love_shiggy. I hope you likie what I wrote. Do not be afraid to throw out idea's or ships! Thank you!)
(Art and characters do not belong to me.)

As the darkness of the sky rises from the sunset of the day, another day has passed is the current city of Musutafu, Japan. During the day the city normally is filled with peace and occasional villianous activities. However, at night is where the bigger one come out. using the darkness around them as a tool to fool and trick heroes. This is no different then our two power struggling leaders. Tomura Shigaraki and Kai Chisaki, also preferred to be known as Overhaul. While they may have their differences and did meet on the wrong foot, the two have been together as a couple some time after Overhaul lost everything. Instead of taking his arms, the league of villains captured Overhaul and helped him while also taking the drugs for their own use.

They have stayed in their separate paths, groups, and goals, but would meet up with each other at least twice a week to build their bonds whether it was a date, talking out their problems, or just simply existing in eachothers presence. Whatever their meet ups had in store, they both mainly enjoyed it and once in a while would end up bickering about something such as their goals and any future plans they may want later on. Despite the twisted and evil love they danced in, Shigaraki couldn't help but feel like he finally had someone outside of his league who cared about him. Chisaki on the other hand, was slowly understanding the concept of love and what it meant to actually care about someone rather than himself and his work. It was difficult, but he tried whenever he was with Tomura.

Recently though, things have not been going the way they were supposed to for either side of their coin. Shigaraki has been having issues with getting stronger and has been forced to fight battles that were challenging for him and the league, leaving him and his group beaten up. Regardless, they won and gained numbers within their ranks, becoming what was known ats the Liberation Army. However, he had been having trouble with his quirk in terms of strength. Overhaul, howver, had lost everything from the heroes and was left with nothing as he was imprisoned and had his drugs and his whole operation stripped from him after being put in the hospital. He was treated from his damages and had been injected with one of his permanent quirk destroying bullets, leaving him quirkless.

Though before he could sent to prison afterwards, Tomura found out where his boyfriend was and had snuck into his hospital room during the night hours. Overhaul looked over, a glimmer of hope in his dull eyes before he glanced away. The two had been so busy, they haven't seen one another in at least a few weeks.

"Let me guess...you're disappointed in me...?" Overhaul muttered, sitting up so that Shigaraki could sit on the bed with him. The shorter male did as such, glaring at Overhaul before examining his condition. A feeling of disappointment, anger towards the heroes, and some sort of concerned washed over Shigaraki as he spoke.

"What. Happened..?"

"Huh-" Overhaul was then cut off, "I said What happened..? Why are you in here..?"

Kai huffed and looked away, "I was outsmarted by a boy from UA...severe case of hero syndrome. Even convinced Eri to help by rewinding his body while we fought. I almost had him, but he dodged me and landed a blow to my head...then suddenly I woke up in a police car while being taken here." He muttered, slight anger in his tone, "They took my life work and used one of the bullets to take my quirk away..."

This caught Shigaraki off guard. The heroes took his quirk? Why? Wasn't that against their code or something. Hearing this from Overhaul made him boil a bit, but he had to stay calm, not wanting to concern his healing partner. He was then snapped from his thoughts when he haerd Overhauls voice calling him.

"Tomura? Hey, you alright there...?" He asked with a head tilt. 

Shigaraki sighed and shook his head. "No...and you aren't going to like me for this."

"hm..? What are you talking about...?"

Shiggy hesitated before glancing at the window he snuck in from, "I won't be able to get you out of here...if you were hoping for that."

Overhaul looked puzzled, "I wasn't completely expecting it...but is there a reason why?"

"I'm going to be put in a coma for four months...the doctor said that I would be put through immense pain the whole time in order to mutate me and my quirk...though he said if I live, I would be unstoppable. I've been working on that the whole time. Increasing numbers and fire power in order to overwhelm the heroes and destroy society to it's max.." 

Kai felt a bit of worry when his ears heard that his partner would be in immense pain for the next four months. It pained his heart as well to know that they would be separated until then. He frowned and looked away, "You better live...I don't need to lose you too..."

"Don't worry about me...you need to worry about yourself until I can get you out of prison."

"I'm serious Tomura...I better not hear you being dead...besides pops, you're the only other person I care about..." Overhaul muttered, catching the silver haired male off guard again. Shigaraki was then pulled by Kai into the bed, slightly wincing as he held onto Tomura. He didn't like being touched usually, but at this moment, Chisaki didn't care. They both knew deep down this was their last night together for a long while. Normally Shigaraki would cuddle much like this, but he didn't care either.

The two spent the next few hours cuddling in Chisaki's hospital bed, being lucky that none of the police or docters came to check on him. Though they knew they couldn't stay like this forever, both Tomura and Kai wanted this moment to last as long as possible. When they broke from their snuggles, Kai handed Shigaraki his Overhaul mask while Tomura gave him some gloves that matched Tomura's wearable hands: white with yellow cuffs on them.

"Thanks...i'll try not to dirty them in my cell.."

"Good. And I'll keep your mask in great condition."

Overhaul nodded as Shigaraki went to stand and make his escape. Though the silver-haired male paused by the window, setting the mask down and going back to his partner, shocking him as their lips collided in passion. They didn't kiss much either, but with this being their possible last moments together, Kai didn't protest, returning the kiss with just as much passion. Their connection never broke, the two staying lip locked for a minute before being forced to break for air. With a slight fluster in their face, Shigaraki grinned, "I'll see you in a few months, bird boy."

Overhaul only smirked back with his heart smiling in warmth, "see you soon, angel..."

With that, Shigaraki went towards the window and snuck out, leaving his partner in the hospital to rest as he goes to prepare for his intense training with the doctor.

(1177 words in total. Hope you enjoyed this.)