Pee Wee Gaskins
Gaskins' serial crime began before the concept was even realized, as a juvenile, which included along with a group of other youths: robberies, assaults and a gang rape.  In prison, he was regularly raped.  He escaped from prison in 1955 by sitting in the back of a garbage truck and fled to Florida; he was re-arrested, remanded and paroled in August 1961.