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Itto's serious tone can especially be rare, but when one of the members of his gang are hurt, especially his pride and joy, he can often put on a serious tone and expression.
Itto had noticed that Shinobu hasn't been acting like herself recently. She's usually needed quite a few moments alone, has gotten more irritable both towards him and his gang and... she's now almost about to cry...? Oh no, this really isn't good.
"Ushi, I may need to count on you for this."
"Moo moo, moo! (I know you will.)"
Itto and Ushi ran over to Shinobu, going down to her level and putting a hand on her face while using the other hand to slightly pet her shoulder.
"It's okay Shinobu, you can let it out here." Itto assured her.
"Moo moo!" Boss is right!)
After those words, Shinobu started slightly crying. "I-Itto.. i can't anymore..."
"Why Shinobu? Why..?"
"Moo.. Moo..? (Is everything alright?)"
"My family... Everyone keeps talking about how their family supports them and what they do for a living.. but.. mine doesn't.. they fucking don't and they never fucking will..."
Itto's face turned into a concerned one as he picked up Shinobu, and placed her on his lap, hugging her from the sides and using one of his hands to pet her hair, and to rest her head on his chest. As he was doing this, he felt a warm sensation on his face, the same one he feels when he's around her. He knew he loved her, but how did she feel about him..?
"Family can be a very hard topic for some people, if you don't have one that loves you and supports you, me and the gang will be your family, right ushi?"
"Moo moo.. moooo!"
"See, Ushi says him, me, and the gang will always love you and cherish you. No matter what."
At this rate, Shinobu practically burst into tears and buried her head into Itto's chest. He kissed the top of her head and leaned onto it. Shinobu took her head off of her Boss' chest for a bit to take a few hyperventilated breaths.
"Shinobu, your breathing's a bit too fast, have some water and take deep breaths."
"Moo mooo! (He's right, take a rest."
Itto then kissed Shinobu on the forehead and it seemed to him that her body temperature was increasing.
"Your face is getting all hot and red, are you sick right now?"
Ushi then gave Itto a waterbottle.
"Here, take a drink. You need to stay hydrated."
Shinobu was usually the one cleaning up after the boss' delinquent messes, but now Itto was cleaning up her emotional one. She felt so small when she was held by him and always had a crush on him, this crush was growing too obvious now, so she just had to tell him through trembling tears.
"Itto.. I- Itto... I love you..."
"Of course! I love you too Shinobu."
"N- n- not as friends..." Shinobu cried even more.
"Lovers.. Lovers..."
"Oh.. Well, I've also been thinking about dating you, I mean, who wouldn't want to kiss your cute little face?" Itto then kissed Shinobu on her lips and chuckled slightly after.
"Boss-"
"Yes, I love you like that too."
Itto then kissed her again near her chest.
A couple of minutes later, Shinobu fell asleep in Itto's grasp, and was carried to his bed, where they both slept together for the whole night.