Malachai

Malachai was originally Mana, a devoted house wife and petty thief with a husband and child. One day, she stole a ring that slipped on her finger and caused her to gain terrible power, but also to become male and, not to put too fine a point on it, fairly evil.

Malachai had a grand reputation as a courageous, if id-driven hero. In truth, by the end of his life, he was a monster. He'd killed, manipulated, raped, and abused countless innocent and undeserving people simply to feed his own ego and appetites, and despite his high position in the guild he was disliked by many who had worked with him. Among his notable victims are Nelliel’s parents, whom he murdered when she was just a young girl, and Raine, whose nymphomania he frequently took advantage of against her will, and who believed she'd killed him by throwing him off a cliff during their last meeting. Raine could have overpowered Malachai at any moment, however her nymphomania did not allow her to protect herself from his rapes. Eventually, he was assigned Maylis as a guild squire and sent off to slay the dragon wrecking Orolthine. After failing to slay the dragon and then losing to it in a brawl, he took to Gelethe, drowning his rage in a bar before an old flame's brother walked in.