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James was a self-described dork during her teenage years. Her breasts grew to a D cup by the time she started high school. After high school, the age of 18, James moved to Nashville, Tennessee, where she worked as a nanny.

In her 20s, James made an attempt on becoming a professional beautician; however she became disinterested and dropped her pursuit because she did not want to hear women "bitch all day long.

James decided to become an exotic dancer under stage name Jesse James in the early s. She noticed the emerging trend of dancers getting large breast implants and decided to get herself a pair of implants.

It was until two years later that she began using the stage name Casey James. In , James joined the Miami-based Scoreland magazine as a centerfold.

During her time with Score, she maintained an official website, but later shut it down due to her iFriends venture. Besides that, James made television appearances in Germany during the peak of her modeling career.

For the rest of the s, James maintained a relationship with her fans though nude webcam sessions. In , James returned to the modeling when she posed for nude videos for BoobTrifecta.

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