Yes. Started with Armor rep(Angelica) soon after she was introduced, and same with Dancer Girl(Nefe). Actually, the latest novel volume out in English was half about him having a threesome with those two(other half dungeon floor clearing, mc making pieces of clothing(swimsuits, underwear, bras..), measuring the whole girl ensemble's bodies(lots of moaning and such..), tentacles, jelly tentacle baths(for measuring purposes, ...supposedly), catsuits, whips, some other...). For some reason this manga omitted the whole volume, it starts and ends at the start of the current, church girl, arc.
Armor rep and and Dancer Girl in the novel are desperate to push the rest of the cast as his wives, particularly School rep, as they feel the two alone aren't quite able to keep up whit the aforementioned 'night-time activities', and also, because, as dungeon emperors, they can't have children and thus think themselves unworthy of being his primary wives. Unfortunately for them, at least at that point in the novel, they haven't quite succeeded in that. Though I'm not personally sure how different the 'measuring sessions' are from it at this point, to be frank...
