To my awareness there are no clear announcements on the next update. However, the last public Patreon announcement (from 16th October) shows the new pool location: https://www.patreon.com/posts/pool-time-9110159 So my guess would be that the next update involves the pool in some way. But that's just speculation at this point.
Regarding your title question: The developer has stated multiple times that this is to come at some point in the future, but for now they're still expanding on the "getting caught" theme for all 3 female characters.
Halloween themed content hasn't been confirmed anywhere yet. But I'd very much like to see that as well.
