He might meet Goku first. Goku is often the main character in DBZ and is usually the first to approach new people or challenges. So it's likely that Goku would be the first one Naruto encounters, and they'd probably start off with some kind of misunderstanding due to their different cultures and fighting styles.
It could be Krillin. Krillin is a friendly and approachable character in DBZ. He's often out and about, and since Naruto would be an unfamiliar presence, Krillin might be the one to approach him. They could start a conversation about their respective powers and how they train. And Krillin could show Naruto around the area a bit before introducing him to the rest of the group.
I think Naruto could meet Bulma first. She's always around, inventing things and getting involved in various adventures. Since Naruto would be a new face in the DBZ world, Bulma would be curious about him. She might try to study his ninja gear or ask him about his world. And then through Bulma, Naruto could be introduced to the other Z - Fighters.
Perhaps Naruto would meet Rukia first. Rukia is often out on missions and is one of the more accessible Soul Reapers. She would be really curious about Naruto's strange appearance and abilities. And Naruto would be equally intrigued by Rukia's spiritual powers and the way she handles her zanpakuto.
Naruto could meet some young and upcoming Iwa ninja trainees. They might be curious about Naruto and his abilities from Konoha. These trainees could either look up to Naruto or be jealous of his fame, leading to various interactions. Also, there could be some old - timer Iwa ninjas who remember past events involving Konoha and have their own views on Naruto's presence in Iwa.
There's a possibility that Naruto meets some of the younger generation of shinobi in Suna. These new characters could be eager to learn from Naruto or challenge him to a friendly spar. He may also come across some of the elders in Suna who have their own stories and wisdom to share with Naruto.
In this fanfiction, Naruto might run into Arthas Menethil before he fully turned into the Lich King. It would be a very different kind of encounter compared to what he's used to in his own world. He could also meet Uther the Lightbringer. Uther might be curious about Naruto's unwavering will and Naruto could be in awe of Uther's connection to the Light. Additionally, he could meet many of the adventurers and common folk in Azeroth, each with their own stories and skills.
He could meet some new and powerful shinobi who have different fighting styles compared to those in the Hidden Leaf. For example, some shinobi who are experts in wind - based jutsus that are unique to the western regions.
There's a chance he could meet an older and wiser Kakashi. Kakashi might have new insights and stories to share with Naruto from all the years that have passed. And also, he could run into future shinobi who look up to him as a legend from the past.
Naruto might meet Itachi in heaven. Itachi could finally reveal all the secrets and the true intentions behind his actions to Naruto. And they could become true friends without any misunderstandings. Additionally, Naruto could also meet Neji, and they would talk about how the ninja world has changed since Neji's sacrifice.
Naruto could meet some young Uzumaki ninja - in - training. They would be excited to meet someone as famous as Naruto and might learn a lot from him. Also, there could be some reclusive Uzumaki who have been hiding special abilities that Naruto discovers during his stay.
Naruto might meet a wise alien sage who has knowledge about a different type of energy that could enhance Naruto's own powers. This encounter could lead to Naruto's growth and development in new and unexpected ways. He could also meet some friendly space creatures that help him on his journey through space.
He could meet a strict teacher who doesn't understand his unruly ways at first. Maybe a shy student who he befriends and helps come out of their shell. And there might be a rival student who challenges Naruto in various aspects like grades or popularity.