Wanted to do similar mechanic in similar way for my jam but never managed to pull it off. So I'm happy to see someone executed this in a neat way :D Took some runs to get into the groove. Sometimes a bit unresponsive and janky to complete a loop, but at least nice that you can continue to hold down mouse after a loops is completed so you can continue drawing after executing your damage.
Game I worked on can be found here for Review 4 Review https://loopypeople.itch.io/loopy-pirate