Caroline, The Latex Sister

Her mother was killed when they were attempting to leave Skyrim. A imperial ambush caught them near the border and took them back to Helgen, where Cassandra was executed. She was seven when the legion sent her to the orphanage in Riften, the same day a dragon destroyed her birth town.

Eight years passed when she ran away from Riften with one purpose in mind: take revenge against Empire. The knowledge acquired when practicing with the Guild was very useful and she used to sneak into imperial camps at night and kill many soldiers as she could, what brought the attention of Dark Brotherhood to her.

One day, the Falkreath Sanctuary was invaded by the legion, and almost everyone were killed. After that she decided to stay alone for a long time until the day she created a new clan, the Sisterhood, to spy the Empire and the Thalmor when contracted by them.