She could be the captain of a penalty ship, taking the petty thieves of Britain to a life on botany Bay. However she makes some cash on the side by selling a few of the more aesthetically pleasing to wealthy Foreign slavers on the way.
A particularly bad commute gave me these ideas for you Warden. 1) The Thief in the Sheets. Seducing either the Governor, the Governor's son, or the Guard Captain, she manages to acquire vital information in order to rob the Vault blind. 2) Crossing Swords and Shot. Fighting gets her hot. And everyone knows that if you can fight her to a draw, she will reward you with a blowjob. Bus since she's never been defeated, no one knows what happens if you win... Until now. 3) Last Breath at High Tide. There is a perverse kind of joy she gets when she takes her captive's last orgasm before having them thrown overboard. 4) Ivory Pearls. A young noble bachelor has been kidnapped, and she plans on retiring soon. Might as well get started on that rich-man's wife's lifestyle by having that brat early. 5) Betrayal on the Miss Royale. Finally at breaking point, the sexually frustrated crew of the Miss Royale mutiny, and use their former captain as a relief station. 6) Swimming in Sea-men. Morale has plummeted after several unsuccessful raids, and the captain has to take steps to keep her crew's spirit's up. 7) Windswept Sails. Spotting the Jeweled Unicorn's colours on the horizon, the two captains arrange to have a private meeting in one of their cabins that will last all night long. Do you know how rare it its to find your spouse out in the middle of the ocean?
8) Untitled Femboydom Futasub humiliation story. A crew of futa pirates attempt to capture a ship of femboys. Unfortunately, they have grossed underestimated their would be captives when it turns out those femboys have monster cocks that they use to dominate the futa crew and expose the futa captain's 2 inch penis.
It was not surprisingly a very grey area. To take two of the better known pirates as example Captain Kidd started his voyage as a privateer charged with hunting pirates. Captured a French ship that had an English captain and had been leased to an Indian noble, on his return to England, peace having been concluded in the meantime was charged with piracy and hung. Captain Morgan also began as a privateer and sacked several towns along the Spanish main. He was also charged with piracy, but received a hero's welcome when returned to England exonerated, knighted and later served as governor of Jamaica. Another complication for the British was that after James the sixth or first (depending which side of the border you stood) they had one king but separate English and Scottish parliaments. There was a lengthy time delay between England making war or peace on a nation and Scotland following suit. Also the time delay between nations making peace and the news reaching a privateer captain at sea or colony meant attacks might occur months after a war had ended.
Sinbad-style fantastical adventures? If you don't want it to be too rapey, just have a crew of sexy and willing side characters.
The character in the prompt suggests someone who constantly wins through trickery, guile and a smooth tongue, rather than overwhelming force. How about something like, A small band of independent pirate ships being harassed by the superior British navy. Captain (pictured above) suggests to the others if they can engage them briefly to provide a distraction she will take their flagship and get them to withdraw. She does this by subtly coming around behind them and instead taking the comfort ship which is carrying all the officers wives and daughters, which is following the Fleet just over the horizon. British surrender and hand over flagship after a good bit of fun
I'm kind of intrigued by the pleasure ship concept in the first place. Maybe she was one of the wives and daughters, committed mutiny, and now she and the other womenfolk are rampaging around the Caribbean chased by their exes.
