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Ireland returned to Colorado to continue college partially in Boulder, Colorado, partially in Fort Collins, Colorado, and began to dance in a Fort Collins strip club. One of her first female lovers was a waitress at the same club who would become the pornographic actress Juli Ashton. She entered the pornographic film industry in 1994, through an acquaintance with glamour photographer Warren Tang.
From 1995 to 2000, Ireland performed in exclusive contracts, starring in a few films per year, while traveling across America and Europe, strip tease dancing and promoting her films. When her contract with VCA expired, Kylie shattered her "girl next door" image by directing her first movie, The Whore Next Door. In this movie, she performed many sex acts on-screen for the first time, including her first double-penetration, double-vag, double-anal, and gangbang.