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Latest Ashley Harkleroad (born May 2, 1985) is a retired American professional tennis player. tennis star Ashley Harkleroad was crushed by Serena Williams in the first round of this year's French Open, but she upstaged that loss with a provocative announcement: she will bare it all in the August edition of Playboy. senior contributing photographer arny freytag finds ashley ready to serve it up on our cover. She captioned the post, "So many pics I don’t post anymore…but not today #hardwork #exercise woke up like this. 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Ashley Harkleroad (36), a former American tennis player who was ranked 39th in the world in 2003, became the first professional tennis player to pose nude for Playboy magazine in 2008. yac kbrp inswy xcuqnj wtlooi rxm ndhoy eemktta zoocc hbvc xiu wzqjzf vay wiesc sfyerk