Hello!
To be clear - Chuuya doesn't push Dazai into *anything* he doesn't want to do, is more him teasing, understanding and letting Dazai take his time/control's what happen. This fic is based off a backstory I mentioned in my fic Confused (Akutagawa/Atsushi) but these are two separate stories so you don't need to read one to understand the other.

POV does shift in some chapters but hopefully it's clear where it does shift.

Mentions of sex are briefly in a conversation in ch4

Sixteen

Chuuya had never been shy about exploring his sexuality. Granted when he was with the Sheep he didn't really have much chance, but now he was settled in the Mafia, the world and everyone in it was his.

With all this choice, who did he want?

Dazai. The insufferable brat Osamu Dazai.

He knocked on the door to Dazai's room. It was only a few steps from his own, on a high floor of the mafia headquarters, as Mori wouldn't let them get their own places until they were eighteen. Dazai opened the door, still in his suit. Like Chuuya's own room there was a small living room/kitchen area, and a short corridor leading to the bedroom and bathroom.

Dazai had a bowl of freshly popped popcorn in his hand

"You're late." Dazai greeted him

"Well considering your meeting ran over I thought you'd like some time to change and relax."

"Ha! Chibi wants me to dress up allll fancy for him, does he?

Chuuya blushed, "Pfft! You need some fashion sense first. What game have you picked to lose today?"

"Mario Cart," Dazai grinned.

"Best of three?" Chuuya asked as he flopped on Dazai's settee, glad that Mori had furnished the rooms as it was actually comfortable. Dazai nodded as he sat down placing the popcorn between them, two bottles of chilled Ramune were ready on the side table.

"No cheating this time" Dazai instructed as the game loaded.

"I'll play as fair as you do,"

Three games later and Chuuya had wiped the floor with Dazai on every lap. Dazai had declared they needed a break, going to get more snacks and drinks. When Dazai returned to the settee Chuuya decided it was time. He took a deep breath, he could do this. He was only nervous because Dazai was notoriously quiet about his dating life and he wasn't really sure that Dazai actually liked men.

"Dazai…?" he trailed off, confidence waning,

"Yes chibi?"

"Can I kiss you?" he blurted out.

Silence.

A strange look on Dazai's face, a mix between fear and want.

"You, you don't have to, I just…"

"I, we're only sixteen, I'm not ready, I mean I've never thought of it, the work Mori gives me takes up all of my time, and it's not like…" Dazai's rambling trailed off, he took a sip of his drink, "You want this sort of thing then?" he asked.

Chuuya felt like it was a trap, but there was genuine curiosity in Dazai's voice, like Chuuya's request was a puzzle for him to figure out.

"Yeah, it's nice, you can lose yourself with someone for an hour or so. I don't know, I've never really thought about wanting to kiss, touch and date, beyond just wanting to."

"Huh," Dazai was quiet as he mulled over Chuuya's reply.

Chuuya helped himself to some more popcorn, afraid to speak. Dazai finally zoned back in, shock his head, and grabbed his controller.

"Best of three?"

"Sure," Chuuya smiled, glad his request hadn't made things too weird between them.

"I went easy on you to begin with so get ready to lose!"

"Ha! Keep telling yourself that."

Chuuya could live with this. It wasn't an outright no. He'd just come back to Dazai when he was ready.

In the end Chuuya managed to beat Dazai in all bar one game, he was looking forward to gloating and rubbing it in Dazai's nose until their next game night.