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How do I obtain the new outfits for both characters and access the new job?

1) Perversion 40+ (both characters).
2A) With Cassiel, recieve a punish and a prank in her Waitress Job.
2B) With Saaphire, recieve a punish and a prank in her Nun Job.
3) After that, just go to sleep and you will recieve the quest.

Thank you for replying. I would like to know about more thing if you don't mind, how do I increase perversion? Do I just repeat scenes? Thank you.

(+1)

just, try to find every H scene, complete the 2 specials (halloween and christmas), and that's it.
Ohh! repeating H scenes will not rise their stats, unless the scene has added content the 2nd time (or 3rd or 4th... etc)