For this reason, she says that she has no problem with letting Issei see her naked and even lets him touch her breasts from time to time.
In Volume 8, Issei and Rias go through a ritual where they are tested to see if Issei is worthy of being a candidate for Rias' future husband.
They both passed and although Issei remained oblivious to the situation, he had mentioned that he would like to marry Rias one day.
In Volume 10, Issei was given permission from Rias's mother to start a harem to keep the girls around him happy.
In response, Issei will do anything to protect her, as he loves her just as much as she loves him.
To add to that, Issei usually sleeps next to her naked.
This causes tension to form between Rias and Issei until he proclaims his love for her in front of the audience during the Rating Game against Sairaorg Bael.
In Volume 17, their relationship has improved to the extent that despite going out on a date with someone else, Rias chose to believe in Issei and the fact that he will still love her.In fact, when Asia was supposedly killed by Shalba Beelzebub, the negative emotions of losing Asia made Issei enter the Juggernaut Drive and brutally mutilate him, nearly killing him.Issei often has lecherous thoughts about her, but tries to block them, believing that he must protect her from everyone, including himself, and tries to think of her as a younger sister.When she learned that his spirit is alive, she cried loudly out of relief, joy and regained hope, embracing him when he returned.Asia desires to stay with Issei forever, even if it means becoming one of his peerage, which happens in Volume 22 when she became his official Bishop.
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During this time, Issei was struggling to overcome the trauma that was caused by Raynare.