Our Saturday night gaming group has always shifted through games, never seeming to be able to pick one up and keep going due to unreliable players.  We've done D&D, Exalted, nWoD Mage, and just about everything else in-between.  My girlfriend Emi is part of the group and a longtime RPer and fan of most things White Wolf (and suffers from the reverse of GM's Favorite Player syndrome - I usually tend to saddle her with the bulk of misfortune, half because it's a running joke, and half because she's fantastic at rolling with things and involving it into the story), and I ran Dogs in the Vineyard for her, which she absolutely loved.  So I promoted Poison'd as "from the same guy that did Dogs," and she became interested.

Our other player is Jeff, resident min-maxer and loophole-hunter.  He loves to talk and loves to scheme, taking the limelight for a bit too long unless others calm him down a bit.  Once he's got his machinations under way, though, he's all about getting the group involved and forming an airtight plan, and that's good.  Although small, the core team (myself included) work with each other to make the game fun.

Other players flit in and out of our games, but Poison'd has remained largely myself, Jeff, and Emi.  Fellow player Audrey, who herself is pretty bad at roleplaying, played two sessions and really got into character, improving with each passing.

So here's what happened.

• Jeff - Blonde-Beard Sam: schemer with a raspy throat due to neck injury and current Captain, previous Captain's First Mate.  Plays the crew off of each other to keep them content.
• Emi - Bad Luck Katelin: somewhat the crew's whore, but also a capable sailor.  The only one in the group who can pull off a passable British accent.
• Audrey - Alice the Savage: to be honest, there wasn't much depth to the character.  She was the sailing master and co-whore.  Since she's in premanent NPC status, she's been relegated to official company prostitute

The first session: Tom reed is shot in the face with little hesitation.  An NPC named Hughes steps up to be captain, and goes about making poor choices for the ship.  The Dagger docks to try and fix the initial Wear and Breakage, and spies a French merchant vessel leaving port that night.  Bad Luck Katelin and Alice try to convince the Frenchmen to stay, and eventually persuade them with a night-long party of rum and sex.  In the morning, the duo board the vessel and steal all their gunpowder, then head to the local general store to try and work their womanly charms on the shopkeep.  He ain't buyin' it though ("I got me a misses right upstairs.  You know what she'll do, come find me ogglin' a pair o'wenches?  I get a pin upside me head, that's what.")  They return to the Dagger and round up some of the crew, then return to the general store and shoot point blank both the shopkeep and his misses.  The place is looted, the pirates barely escape the approaching constabulary, and the Dagger leaves port to wait for the departing French vessel.

An urgency Cruel Misfortune card warning of a storm enters play for some reason, but for the life of me I can't remember why.

The merchant vessel is quickly overtaken, and the captain is tied and dragged behind the Dagger as it sails off, leaving the beaten merchant ship to sink.

Upon discussion, Captain Hughes suggests the crew overtake a fort and go and hide there to escape the Resolute.  Blonde-Beard Sam conspires with the chief officers of the ship (Rat-Faced Jim, the Quartermaster, chief among them).  Bad Luck Katelin attempts to nab some easy X's by beating the shit out of a different Sam, who's gotten drunk and made snarky comments her way.  He gets tossed overboard, and as Captain Hughes comes to see what happened, he too is tossed over.  Blonde-Beard Sam is elected Captain (hooray!) and Katelin is elected new First Mate.

The storm looms overhead, and the tales of the Resolute making its way to the coast circulate.

Pulling into port to wait off the storm, the crew grows restless and bored, with little Leisure to do much with.  To prevent a Malcontentment card entering play, Captain Sam arranges boxing matches for the crew, with the winner gaining an extra point of Leisure.  The winner is a hulking, toothless man named John Davy White.  Captain Sam adores him since he's brutal and ferocious and nominates him leader of the initial boarding crew on the next treasure hunt.  Katelin calls him out (I used a "going into danger" roll here because she's entering danger - Davy is much, much bigger than her, and essentially decked the entire crew with his hulking, bloody fists.  Vincent, was that the right call?) and stares him down, telling him he's incompetent and doesn't deserve the first strike.  Davy, humbled, storms off and returns with a giant rusty knife, coming at Katelin.  She pulls her gun out and blasts his monstrous ass - Davy falls to the deck, bleeding and convulsing.  Captain Sam is thoroughly pissed - his prized pirate is down for the count.  As Davy goes to make a bargain with the Cap'n, the surgeon is brought out and taken into the cabin for repairs.  Katelin heads in and beats the shit out of the helpless Davy, to teach him a lesson (and nab precious Xs!)

Davy is stitched up but weakened.  He and Katelin are uneasy.

Captain Sam chooses to hunt for a prize, and stumble upon a merchant vessel called the Open Shoppe and its escort, the famous British ship, The Devil's Horn.  Utilizing the flashback rule, Sam's player sees the Devil's Horn in the distance and grimly recounts a tale for the crew whereupon his old ship had to escape the Brits (he made a cunning / stealth roll to try and lose the British ship through a stretch of islands), and kept them going in circles for days.  The Devil's Horn is a huge ship, and the Dagger tries to steer cleer, circling around to get to the Open Shoppe where it then sends Davy and his crew over to deal with them while the main of the crew deal with the guard ship.  Broadsides are exchanged, with both sides suffering Wear and Breakage - the fight is in the Dagger's favor somehow (despite being badly out gunned) and the Devil's Horn is quickly boarded, Katelin leading the charge.  Crew versus crew goes on, and the British are royally stomped.  The merchant vessel is well taken care of, and prisoners are brought aboard the Devil's Horn and given an offer: Join the crew or leave peacefully.  Most of the British choose to leave peacefully, but once out at sea in a small escape boat, they are shot to death by cannon.

And thus the fleet is created: Davy becomes captain of the Open Shoppe, rechristening it "Davy's Ship"; Katelin becomes captain of the Dagger; and Captain Sam leads the Devil's Horn.  Both new ships are manned by a skeleton crew.  The plan is to have Davy's Ship lure in other merchant ships or tangle up and distract enemy ships, while the Devil's Horn comes blasting in and the Dagger boards and kills.  However, first, they need new crewmen.

Spies & Assassins enters play.

Bad Luck Katelin enjoys a night on the town with proper grooming and disguises herself as a man, also gaining access into the Governor's ball, where she charms several ladies (Katelin's all about the ladies) and takes one home to the ship to rape.  The Captain also does the same, netting Xs for "attacking a helpless opponent" with inferences to quite violent acts.  Deciding to keep her for ransom, they find out the next morning that she's actually the constable's daughter, and force her into a bargain at swordpoint - do everything in her power to keep the guards off their backs whenever here in port (Johnston Bay), and she can go free.  She accepts and leaves, disgusted she's fucked a girl, and sore from fucking Blonde-Beard Sam.

Next, Sam and Katelin head into the Governor's office and demand an official privateering license.  Sam boldly lets slip that he worked under the notorious Brimstone Jack and leads the Dagger, yet "had no IDEA they were pirates until it was too late!"  The governor doesn't buy it, but eagerly agrees to help them with everything they need in town.  Once they're out, he sends off word to the British navy of the Dagger's whereabouts.

The Resolute draws closer.  All the ships are repaired but understaffed.  The next prize is on the horizon - a fortress and two merchant vessels.  Time to see if the coordinated attack works successfully.

The problem I have so far is getting the PCs to scheme against each other, or to develop mistrust and fractures against one another.  They also don't seem to want to pursue their Ambitions, instead enjoying lives of bloodthirst and hedonism (which is fun too!)  It seems to be time to start throwing in complications.