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Pressler hails from Franklinville, New York. Her first major pageant title came in 1994 when she won the Miss New York Teen USA title. At the national pageant that year, she failed to make the top 10. She ranked 45th in the preliminaries, almost dead last.

In 1999, Pressler went on to win the Miss New York USA pageant, which allowed her to compete at the Miss USA pageant held in Branson, Missouri. She became the fourth woman from her state to win the Miss USA title, beating press favorites such as Miss Tennessee USA Morgan Tandy High (the eventual 1st runner-up) and Miss California USA Angelique Breaux (the 2nd runner-up and later American representative and semi-finalist at the Miss World pageant).

Pressler later competed in the Miss Universe pageant held in Trinidad and Tobago. She became only the second Miss USA not to place at Miss Universe in the history of the pageant, where her preliminary performance was generally regarded as poor and too conservative. She did however manage to place 19th in the preliminaries in a field of 84 contestants.

Pressler later moved to Los Angeles, where she embarked on a movie and entertainment career. She has been featured in a number of national magazines including People magazine and was voted one of Stuff magazine's “101 Sexiest Women in the World”. She is currently owner of a promotional talent agency based in Los Angeles that specializes in motor sports events.

Pressler has also hosted a number of Miss USA state pageants, including Miss Massachusetts USA 2006.

In 2007, Pressler was heard as a reporter for the X Games XIII for ESPN. She was also a reporter for 2008.

In 2008, She was given the award for 'The Best Porn Star of the year' and was given a 10 year contract with the playboy TV show'sexcetera' that will

begin in 2009.