kareila: a lady in glasses holding a stack of books (books)
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This story puts me in mind of Song Of The Lioness except instead of hiding her gender to be a knight in training, Jacky Faber hides her gender to be a ship's boy in the British navy circa the late 1700's.

After her entire family dies of plague, seven year old Jacky is taken in by a gang of orphans, but after a few years of this hard life, she realizes that begging on the streets of London doesn't provide her with much in the way of prospects, so she cuts off her hair and steals some clothes and bluffs her way into a gang of ship's boys, where no one knows her true identity.

Because of her rough upbringing, she doesn't know what to expect as she grows into a woman, so seeing her deal with that challenge is predictably hilarious. She also earns the appreciation of her crew through her various exploits, and manages to kindle a romantic relationship with the one boy she trusts with her secret. However, she must also contend with an attempted rape (heavily foreshadowed) from a pedophile, and various other life-or-death situations.

In the end, she is discovered and sent to attend a ladies school in Boston. Her story continues on for a total of 12 books, and to judge by the covers, she has quite a colorful and adventurous life ahead of her.

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