I imagine it's building up to him having a 'willing' harem lol
100%. It's already been established that they retain some semblance of memories from the time they're hypnotized the longer they're under its influence; and Aisaka's become proactive in getting involved with him even while not actively being hypnotized.
Eventually, they'll probably end up more or less immune to the hypnosis, but they'll be so smitten with him that they won't really care. Same thing happened in
Sex & Dungeon; main difference between the two, really, is that the MC there actually went all the way and became a full on rapist (somehow, it still ends up kinda heartwarming in the end).