Mary Read led most of her exciting life as a man's life. Her mother and father are unknown The little information known about her widowed mother was that she raised Mary as a boy.

Mary was born in London, and when she was 13 she was working as a foot boy for a rich French woman. But soon she ran away to sign on board a man-o-war. A few years after Mary jumped a ship, but only to enlist in a foot regiment. She fought showing great bravery. Mary later joined a horse regiment where she then fell in love with a soldier. She confessed her womanhood to this man and they were married. The two of them opened up an inn called the Three Horseshoes near the Castle Breda.

Mary's husband eventually died, and once more she wore men's clothing, and attempted once more a life in the Army. She failed at this, so she shipped off to the West Indies. On her way, her ship was taken by Captain Calico Rackham. As fate would have it, another woman pirate, named Anne Bonny, was part of Calico's crew. Anne saw a young strapping sailor among the newly-captured prize and decided that she would have her way with him. To Anne's surprise, when she got the man alone, he opened his blouse and he exposed to Anne that he too was a woman. Then Mary confessed that she would rather join with Rackham and Anne than lead the dull life as a woman and she too became one of Calico's pirates.

Calico was a fairly successful pirate and his crew managed to capture many different ships. Mary fell in love with a newly captive sailor who had recently signed the articles of the ship. The young fellow got in a quarrel with an older pirate with more experience while at anchor one night, and as the laws decreed, a duel was to be set the following day. Mary realized that her lover wouldn't stand any chance againt the other pirate, so she began a quarrel with the bigger pirate, and she demanded settlement on the spot. The quartermaster rowed the two ashore, with pistols and cutlass, and the duel started. They both discharged their pistols for naught and then continued the duel with cutlasses in their hands. The man had strength yet Mary was more agile and cunning. The duel had been going on for a long time. and when the larger pirate made a thrust, he stumbled. He would probably have managed to recover from his slip if it were not for what Mary did next. Before the unbelieving eyes of this pirate, Mary ripped her blouse open and the pirate, not believing what he saw, hesitated for a second. In that instance, Mary grabbed her cutlass and with just one swing of her blade, nearly cut the man's head off. He lay on the ground gasphing for breath, still astonished that he had been duelling with a woman.

Mary's lover was no coward. He showed up to fight the duel that would have meant his death on time, only to find that the duel was with a dead man.

Mary and the sailor were married. Shortly after Calico Jack and his crew were taken prisoner. They were tried at St. Lago de la Vega in Jamaica on November 28 where they were all sentenced to be hanged. Mary, instead of pleading for mercy, told the court, "As to hanging, it is no great hardship. For were it not for that, every cowardly fellow would turn pirate and so unfit the sea, that men of courage must starve."