Raynare

Raynare was a Fallen Angel and the first antagonist of High School DxD.

Appearance
Raynare was an attractive young woman with violet eyes having a slender body. She had long silky black hair down to her hips and possessed two black feathered wings.

Her attire consisted of a short black dress with a small, light purple jacket on top, which was worn throughout most of her appearances in both the light novel and manga.

In the anime, she had a slender body with a large bust. Her initial attire (as Yuuma) was her school uniform, which consisted of a dark red jacket with the letter "P" embroidered in gold, a white undershirt, a red bow, and a green skirt with a thin white strip around the lower end of it.

Upon the climax of her date with Issei, she shredded her clothing and changed into her alternate (and more common) form. In the process of transforming, she grew taller, taking on a more mature appearance, and her eyes changed, taking on a darker, more evil look. Her clothing also changed dramatically, now consisting of black, strap-like objects (resembling leather) around and under her breasts, a thong-like piece held around her hips by three thin straps, gloves that ran right up her arms with small lengths of chains hanging from them, shoulder guard-like objects on her shoulders with three large spikes sprouting from her right shoulder, and black thigh-high heel boots.

Her voice also tumbled to a lower pitch when in this form. This form is best described as a very erotic and revealing version of her disguise.

Personality
Raynare seemed like a sweet and rather attractive young school girl at first, but this was just a disguise to hide her true nature. Her true personality revealed that she was vicious, petty, sadistic, treacherous, vindictive, cruel, barbaric, and very deceptive. As shown when she successfully manipulated Issei Hyoudou's mind in order to get close to him and kill him. She also laughed cruelly at Issei, believing him to be "weak" or "A waste of her time killing him". This shows how Fallen Angels like her can manipulate the will of mere humans with ease.

She is loyal to her superiors, Azazel and Shemhazai, and would go to great lengths for them. However her loyalty may come into question as she tends to take action without their consent, believing it's for the good of all Fallen Angels.

She has been seen as overconfident and tends to look down anyone who is inferior to her, as well as torment and taunt them when she mocks Asia's death to Issei out of spite and shows no remorse.

She had also demonstrated herself to be a coward at the most desperate moments, as she begged the man she betrayed to save her life, only to be obliterated by Rias.

History
Not much was known about Raynare's history, other than the fact that she was banished from Heaven for an offense of some sort. Shortly before the series began, Raynare came into contact with Freed and Asia at some point who became her subordinates.

She was sent to spy on Issei by Azazel because of his Sacred Gears dangerous potential, however she mistook this as a means to eliminate him. Raynare secretly gathered and led an independent group of Fallen Angels and Exorcists who assisted her in attempting to steal Asia's Sacred Gear; Twilight Healing, believing she was better suited for it to serve her leaders.

The Red Dragon Emperor's Awakening
In Volume 1, Raynare disguised herself as a human named Yuuma Amano and becomes Issei's first girlfriend. However, at the climax of their first date, she kills him, revealing herself as a Fallen Angel and explained to him the main reason being the Sacred Gear residing within him posed a threat to the Fallen Angels.

Raynare later appeared after Issei spent the day together with Asia, surprised and disgusted at the fact that he was reincarnated into a Devil, and easily overwhelmed him while revealing the Sacred Gear he used was a Twice Critical before whisking Asia away.

Later, at the abandoned Church, she took Asia's Twilight Healing, killing her in the process, before proceeding to fight Issei in a one-on-one duel with Asia's life on the line. Although she overpowers Issei once more, in the climax of the duel, Issei's true Sacred Gear, Boosted Gear, activates, and she is swiftly defeated by his new power. At her most desperate moment, Raynare demanded Freed to help her, but instead runs away. Before being terminated by Rias, she desperately pleaded Issei for mercy using her Yuuma persona, even going as far as to say that she loves him and could defeat Rias together. Ultimately, Issei replies by telling Rias he is at his limit and leaves it to her, leading to Raynare being turned into ashes by Rias' Power of Destruction. Issei looked in sorrow as remains of her black feathers float around the Church.

Birth of the Breast Dragon Emperor
In Volume 4, Azazel revealed that he sent Raynare to keep a close eye on Issei, but she disobeyed his orders and killed him on her own accord. He reveals that the surveillance was just to make sure that his Sacred Gear remained dormant as there was a high risk of it going out of control or making him go berserk if it awakened while he was still human.