EDIT - Kinda miss read this sorry, But info might be useful to Goji16
The nun is the librarian in the District > Library. Do not quote me on this but I think you have to max out Smart with her (futa) in the Library. You will then get to confess your sins to her in church (select the I cannot stop think about you option) from there you can fuck the shit out of her in the Library when ever you want. The sins option becomes a random event.
I think the guy just turns up at the public pool, and should have some share options with Anna and Norah but I have not seen anything happen with this yet.
The guide has a screenshot of Anna at the Pool, so maybe something happens eventually 🤔
