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In May of 2006 Grey moved to Los Angeles and started her career in adult films just after turning 18. Her first scene was an orgy with Rocco Siffredi for The Fashionistas 2 by John Stagliano. It has been reported she "shocked" her fellow performer by requesting to be punched in the stomach during fellatio. Though Grey does not deny saying this, she emphasizes the request was "an exercise in improvisational fantasy." This resonates to what Grey once wrote in regards to herself as a person and as an artist: "I wanted to express my sexuality as a strong woman, to push my own boundaries and see which part of my psyche would take me to my next euphoric sexual experience." Nearly six months after entering the adult industry Grey was featured in the November 2006 edition of Los Angeles where she was flagged as a potential major star, perhaps the next Jenna Jameson, making her one of the fastest rising stars in adult film history.
Less than a year after entering the industry (January 2007) Grey was the recipient of awards for Best Three Way Sex Scene and Best Group Scene at the prestigious AVN adult movie awards.
In 2008 she became the youngest person to win the AVN Female Performer of the Year award.
In October 2008, it was reported that Steven Soderbergh has cast her as the lead actress for his upcoming film entitled The Girlfriend Experience.