It took time. He would always feel the pain of their death. He could agree that time could lull a sharp pain into a dull ache. The hole in his heart could change and shift it could slowly heal and scar over, but he would always feel a twinge of pain when it rained.
The thing that started to heal his broken heart was a brown-haired boy and a distant look in his equally soft brown eyes. His name meant Heavenly Creation, Tenzo. Creation he could make mixing earth and water type chakra creating wood style jutsu. He watched in awe as this boy smaller than he could even remember being, creating a giant tree-like box to catch the fragments of a little girl turned into gas. His eyes must have been playing tricks on him cause golden hands turning into golden branches reached out trapping the gas and reforming the girl. The girl called him Tenzo or sometimes little brother.
It wasn't until years had passed that he saw Tenzo again and for some reason, that child had drawn him in. He went out of his way to free Tenzo from the darkness of the Root, only to bring him into his own branch of the shadows. Tenzo would be on his Anbu squad and later take over the squad when he was reassigned to be a jounin sensei to the son of his previous sensei, a fangirl and the last Uchiha.
He tried to space himself away from the blonde focusing on Sasuke, the younger brother to another part of his past. Yet another part of his past that couldn't stay silent.
But again he watched his team fall away, and he could help the way that pain tugged at his heartstrings. The lone genius becomes cold and leaves the fangirl and his only friend for power.
His students became other people’s students and he faded back into the shadows of Anbu. Back into his role as Hound. When Naruto returned to the village he was away on mission and Tenzo stepped in.
When he returned both students and team leader were hospitalized. Tenzo was able to move around and Sakura was acting like nothing was wrong. When he went to check on the bright and shining light that was Naruto, he wasn't ready for the dull gaze and unseeing eyes that looked out the hospital window. He could feel those eyes when they turned to look at him and could feel the knife cut open wide the stitches on his heart. When the slow and sluggish movement of his genin turned into a hug that crushed his ribs, he felt his arms circle the now larger frame Naruto. He rubbed the shaking shoulders and lowered his head to rest on the smaller boy.
When Gaara died the first time Kakashi reached out with his chakra like Minato had when Obito died, steading the wave from grief to rage. Rage would be more helpful than sorrow right now. Sorrow came after. Sorrow was for the safety of a defended place and him. Sorrow was for Lady Chiyo.
Sorrow was for the death of Jiraiya.
When he found out that Obito was alive, Naruto found him and pushed away from the mask made up of Icha Icha and self-hate and dragged him to his place where he laid on Naruto's bed and cried. Naruto stroking his hair and wiping away his tears. At some point, there was a gentle press of lips over his eyes, the tip of his nose, the crown of his head, and the tip of his hand.
He gave back those kisses of his own to the whisker-like marks on his cheeks, the scar over his heart, the palm of his hand and his lips.
When Neji died, They held hands and mourned in the silence of the night sky.
When Tenzo or Captain Yamato to Naruto was kidnapped, the sky rage with lightning and gales of wind that howled but there was no rain until later.
When peace had been reached, the goddess defeated, Madara dead and his team was together; he thought it was over. He thought he would go home his a little place with room for his pack, him, and Naruto. When he turned to smile at his golden malestorm, he found a body that looked far too much like Naruto for comfort. This body couldn't be Naruto because Naruto couldn't be dead. He was far too important to be dead. This person wasn't smiling or laughing. His eyes were glazed over and lifeless, his skin was cool to the touch and tight around the bones from a lack of eating.
There was lighting, falling trees, fire, and rain that night. But no wind. Not one breeze.