Aunt Hester, Douglass’s aunt, is an exceptionally beautiful woman. Because of her unrivaled beauty, Captain Anthony is extraordinarily interested in Aunt Hester. After disobeying Captain Anthony’s orders one night, however, Aunt Hester is severely whipped, and Douglass is forced to watch. Though Aunt Hester only appears briefly in the opening pages of the book, the violence inflicted upon her leaves an indelible mark on Douglass as it marks his first encounter with the brutality of slavery. As Douglass describes, bearing witness to Aunt Hester’s beating at the hands of Captain Anthony “was the blood-stained gate, the entrance to the hell of slavery, through which I was about to pass.” Aunt Hester’s whipping inaugurates Douglass into the reality of the slave system and its vicious treatment against slaves. It instantiates the moment where Douglass’s knowledge of slavery moves from blindness to insight, from ignorance to knowledge.

Aunt Hester’s whipping also exemplifies how female slaves’ bodies and sexuality are viewed as objects to be controlled and when, as Aunt Hester does, they resist, they incur the ire of their masters. Aunt Hester not only defies Captain Anthony’s orders to not go out that evening, but she is found with another man, Ned Roberts. More than disobeying Captain Anthony’s orders, Douglass suggests the possibility of Aunt Hester being courted by another man poses a threat to Captain Anthony’s ownership of her body. Rightly so, Douglass earlier alludes to the sexual violence inflicted upon female slaves by their masters, especially as many male masters were the fathers of slave children. By placing this scene early in his autobiography, the audience is forced to grapple with not only the brutality of slavery, but with the particular kind of violence slave women are forced to endure. Douglass’s description of Captain Anthony’s sadistic whipping of Aunt Hester and the perverse pleasure he seems to derive from it reflects how desire, intimacy, violence, and sexuality are complicated under a system of slavery.