Utsuro and the young Oboro are discussing about Shouka Sonjuku, and the former promises to make the child the eldest disciple. The prospect of having juniors excites Oboro greatly, and he is looking forward to meeting them. Shortly after, Oboro notices the Naraku pursuers under the cliff while guarding the sleeping Utsuro. Believing that his teacher will not be able to escape if he tags along, the child comes up with a plan using a trap taught by Utsuro despite the latter’s disapproval in using it for killing.
Stabbing himself with Utsuro’s sword, Oboro approaches Naraku’s 9th division. He lies that Utsuro has deemed him a hindrance and attacked him. However, one of them managed to see through Oboro’s lie and on cue, the division stabbed him as Utsuro watches in horror atop the cliff. Revealing his true intention, Oboro activates the trap just as Utsuro rushes to the ground. Boulders begin falling onto the pursuers and killed almost everyone nearby. Believing that the child has died, Utsuro left in despair.
Oboro survived the attacks due to Utsuro’s blood he received awhile back, and was taken in by Naraku. He began taking on various assassination roles in order to build up his status within the organization to keep them away from Utsuro, determined to protect his teacher and his will despite his absence. It was until one day when he encounters Utsuro, who is now Yoshida Shouyou, and his three disciples that he realized he was wrong – he wanted his teacher back. He ended up betraying Shouyou by revealing his location to Naraku, thus causing the series of events leading to his execution and his resurrection as the current Utsuro.
Looking upon the fallen Takasugi in the present, Oboro admits that he was the one who killed his teacher. Although their weaknesses resulted in Shouyou’s death, Oboro notes that both him and Takasugi vowed upon extreme ends in order to get their teacher back – one will protect the man despite his identity, while the other will kill the man who assumes Shouyou’s identity. Oboro then pulls out the shikomizue on his neck while Takasugi picks himself up and pulled out the katana on his cheek. As both poise themselves for that one last clash, Oboro reaffirms his commitment to his teacher and silently encourages Takasugi to fight on as well, as fellow disciples of Yoshida Shouyou before both charge at each other.
A flashback occurs: Right before Shouyou’s execution, he left a will through Oboro by thanking the latter for allowing him to be Yoshida Shouyou and being able to meet those children he has taught. He also apologized for not being able to let his disciples meet up with Oboro, his first disciple that he is proud of. As the scene cuts back to the present, Oboro silently told Shouyou that he has already gotten a good look of the juniors he is proud of, before collapsing onto the ground from Takasugi’s attack.
- Oboro: (To Shouyou, in thoughts) Sensei, I broke our promise. Ever since my life was saved by you back then; I decided I was dead and that I would throw my life away for your sake, Sensei. Unless I protect sensei's will, unless I protect the disciples I have not met yet, I cannot call my self your first disciple, can I? Sensei; I'm sure you will take care of our school, Shouka Sonjuku......
- Yoshida Shouyou: (To Oboro) It was thanks to you that I was able to meet those children. It was thanks to you that I was able to become Yoshida Shouyou. Thank you. And... I'm sorry. If possible, I would have liked for you to meet. Those children... And the one I'm so proud of, my first disciple.
Characters in order of appearance