Mary Read came to life as the illegitimate child of her mother, and was dressed as a boy to impersonate her deceased (legitimate) brother, to hide her mothers indiscretions from her sea-faring father. She was thus brought up as a boy, a disguise that she was to maintain the greater part of her life.
The military and naval adventures seemed to hold a fascination for her. Hence she chose to serve as a "Foot-boy" aboard a man-of-war until becoming a cadet in a regiment of foot, where "she behaved herself with a great deal of Bravery". She fell in love and married one of her messmates, whom she had informed of her secret female identity earlier. Together with her husband, she opened up a tavern, "The Three Horseshoes" near Breda Holland.
Her husband’s early death, and waning prosperity of the tavern, saw the young widow once again acquiring a male persona, and joining another regiment of foot, on garrison duty in Holland. There was however an interlude of peace, which caused Mary to grow restless. She made a resolution of seeking her fortune another way, and shipped out as a sailor aboard a Dutch vessel bound for the West Indies. The ship was stopped by pirates, and she being the only English ‘seaman’ on board, was allowed to travel with them. Soon after, she heard of a commission for privateers against the Spanish. Once aboard a privateer, Mary joined others of the crew in a rising against the ship’s captain.
Eventually she found herself under the command of Captain Calico Jack Rackham (thus called because of the striped material he used for his trousers). She held herself somewhat aloof from the rest of the Company, and was pretty much accepted as a man.
It was on this ship that she met Anne Bonny, who was Rackham’s mistress aboard, also disguised as a man. At first Anne Bonny mistook Mary to be a handsome young pirate, and begun to make advances, revealing her own sex. Thus Mary was forced to reveal that she was also a woman in disguise, to the great disappointment of Anne. But even so they became good friends quickly, but this closeness disturbed Jack Rackham to jealousy, that he threatened to slit the throat of Anne’s lover. In this way Rackham too was quickly made aware of Mary’s true identity.