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Originally from Naperville, Illinois, Hillary Scott grew up in Chicago, Illinois. It was here that she had her first lesbian encounter, with her best friend. She states she lost her virginity at age 16, then afterwards started dating a girl who became her "high school sweetheart for the majority of high school". She worked in a bank selling mortgages for two and a half years after graduating from high school, but became bored with it and resented having to wear formal attire and remove her body piercings. However in 2006, she said that all her piercings except her ears had closed up. In a 2005 interview, she stated she has social anxiety disorder. She came to Los Angeles in late-August 2004 to try out the adult film industry. Scott's first scene was in the film Double Play #2 for Digital Sin, which paired her with Mark Ashley. She moved to California for good around November 2004. After acting in numerous gonzo films which featured her performances in anal sex scenes, she starred in the larger-budgeted feature Darkside with Penny Flame in 2005. At the AVN Awards 2006, Scott won awards for "Best Oral Sex Scene – Film" and "Best Group Sex Scene – Film" for her role in Darkside. She also was awarded the XRCO Awards for "Best New Starlet" and "Orgasmic Oralist" on April 20, 2006. Scott often uses dirty talk in her scenes, and works without condoms in all her boy/girl scenes. Scott replaced Jessica Sweet in the role of "Britney Rears" for the movie Britney Rears 3: Britney Gets Shafted. Scott announced on the Howard Stern radio program on April 23, 2007 that she had signed what she called the largest porn contract in history – $1 Million over four years. The contract was with SexZ Pictures. Hillary Scott and SexZ Pictures parted ways just a little over two years into the five year exclusive performance and directing contract; Hillary is now booking her own scenes. In a 2007 interview, Leah Luv claimed that Scott has a daughter.