OP, you want to look up "
redirected aggression in cats" - there are far, far too many good articles out there for me to post links to all, but just pick a few and read. It's certainly one issue your male cat has.
I have a male very, very similar to yours. He will have a go at one of the two other cats (both females) pretty much whenever the mood strikes him. He used to have a go at both, but one had a guts-full and flattened him. He's left her alone, or only sort of play-attacks her now. The most submissive one is the one he'd like to shred. The more she hides and runs away from him, the worse he becomes it seems. He was raised with her - he and she lived together in a "condo" in rescue before I took them both and that was nigh on three years ago now. Both ended up in rescue when they were just months old, so age was on their side too. Both fixed young.
With ours, the piddling isn't a litter-box issue, a health issue or anything other than a pure behavioural issue. He will piddle to mark territory (door frames, bits of furniture, the sewing machine
) and the amount of piddling varies in direct correlation to when the last time Stripey Cat was around. Stripey Cat is a big feral tom that our cat hates/is terrified of and is the root cause of 99.9% of the trouble we're having. Our cat's redirected aggression waxes and wanes depending on when Stripey Cat was last seen. It isn't that it just goes away when he's not around, but attacks are somewhat less frequent, and piddling will stop altogether.
I don't have an answer or a quick fix (there isn't one) but you'll find helpful suggestions in some of the articles I'm sure. I seem to remember finding this site's article on redirected aggression quite good - but do search around as some will be more "illuminating" than others.
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