Maou Tasogare

He kidnapped Syalis in her sleep so he has hardly ever seen her awake and has never had a proper conversation with her. He is always thinking of ways to make the hero get to him and gets worried if he is going to lose he even puts weapons and tools to make the heros quest easier. Apart from that he is a good leader for the demons of the castle but even he cant go against Princess Syalis and is shown to care for her to a certain point. Source: Wikipedia