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Douglass had two masters, the first being Anthony (called "Captain Anthony"). Anthony only had a few slaves on a small farm. The overseer, Plummer, looked after the slaves. Plummer was an awful man, given to drinking, swearing, and intense violence. His exceedingly cruel behavior was barely restrained by Anthony, who did not much seem to care how his slaves were treated. He also occasionally delighted in viciously beating his slaves. No amount of tears or supplication or streaming blood would cause him to cease his whipping.
Douglass recalls how his own aunt was often prey to these whippings. The first time he witnessed this outrage, it "struck me with awful force. It was the blood-stained gate, the entrance to the hell of slavery, through which I was about to pass. It was a most terrible spectacle. I wish I could commit to paper the feelings with which I beheld it."
This event took place when he was very young. His aunt had gone out one night but did not have permission to do so. She was romantically involved with a man named Ned Roberts, who belonged to Colonel Lloyd. There was some suspicion that she was also forced to have sex with Anthony, as she was beautiful and noble in appearance. When Anthony discovered her absence, he punished her upon her return. He stripped her naked to the waist, tied her hands to a hook, and began viciously whipping her, crying out that she was a "damned bitch." Douglass was utterly scarred from observing this spectacle; since he had never seen it before, living on the outskirts of the plantation with his grandmother, he wondered if he was next.