Dominate Demon

You target up to 5 fiendish creatures you can see within range, and force them to make Wisdom saving throws. On a failed save a creature is charmed by you for the duration or until they take damage. If this spell is cast on the same creature on consecutive rounds, and the creature's CR is less than or equal to half of the level this spell was cast at rounded down, the charm becomes permanent assuming the creature fails its saving throw both times.

At higher levels, increase the number of creatures you can target by one for each level cast above 3rd.