This was fun and could always be expanded upon, IF desired. In a way it could be considered a far away side story to your VN. While possibly a dumb idea, could make a sequel with one the premises being the Jailer and Jailed falling for each other Trope. In which a lot of time (years) have passed, and can tie into guilt, and repentance, and rehabilitation. The love may form loosely through the Fact that he was bested and has found someone he can consider an equal, and in turn proving himself to be genuine will get the love returned. This all of course wouldn't be without trials for the both of them to trust each other enough. The end goal would be that they use talents as a team and make each other's life easier. Fighting for what is right, but only with themselves do they do any "injustices". New path, but still keeping up its kinkiness. In the end this is only an idea.