Oshima was relocating to Miami Beach from Playa del Carmen, Mexico where she was living and working. Through a mutual acquaintance she met Playboy photographer, Jarmo Pohjaniemi. Oshima stated in her Playmate appearance interview, "I could never have been a model in Japan. I would be considered too busty." After her discovery, she was brought to California for a test shoot as a candidate for The 50th Anniversary Playmate Hunt in the December 2003 Playboy, her first magazine appearance was the pictorial of models auditioning.
In addition to her Anniversary Playmate search pictorial, she also made several appearances in other Playboy editions. Oshima was the covergirl of the 2003 Playboy Special Editions Exotic Beauties and she has also starred in a number of Playboy videos.
In June 2004, she became the second Japanese-born Playboy Playmate. The first Japanese-born Playmate was Lieko English who appeared in the June 1971 issue of Playboy.

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