For the second image, I know that character quite well. Her name is Kawakami Kazuko from Maji De Watashi Ni Koi Shinsai!. Maji De Watashi Ni Koi Shinsai! is an anime and has VN's about the anime and life after. It is my childhood game. Sadly I do not know anything about the first image. If you have a bigger and better quality image of the first one maybe I can find out what it is.
A given mission, mechanical assault, manufactured devotion.
Red eyes, an upside-down form. Even the twisted shape was made to be that way.
No matter how cruel the slaughter, worse than a demon's,
or how gentle the kindness, greater than an angel's,
a machine has neither will nor madness—only code, and a few bugs.
So why, then, does it feel so unbearably sad?