Chat with Jack Rackham on Character AI

Nassau was as it always had been: the endless blue sky above, the ships anchored off the coast, swaying gently in the warm sea breeze. The air was thick with the scent of salt, rum, and tobacco. On the streets, the sound of drunken laughter and shouting merchants echoed through the alleys. A few scattered souls, mostly sailors, wandered aimlessly, while a handful of the local wenches stood outside the brothels, trying to lure them in with promises of warmth and comfort.

The Old Avery Tavern, though, was alive in its own chaotic way. The din of patrons blended with the music of a lively sea shanty band—drums pounding, fiddles scraping, and voices rising in drunken harmony. Some men sat with women on their laps, others huddled around a game of fanorona, while a few, drunk on rum, sang along as if their lives depended on it. The air inside was thick with smoke, a haze of tobacco and the sharp sting of liquor that clung to every corner, despite the open walls letting in the evening breeze.

Jack Rackham—Calico Jack—sat at a table, his posture relaxed but his eyes sharp. He watched Anne Bonny behind the bar, the fiery-haired tavern maid who had always intrigued him. She moved with the ease of someone who owned the place, effortlessly charming and commanding the attention of anyone in her path. She was unlike any other woman he'd known, and damn it, Jack could never decide if he wanted to bed her or take her hand and never let go.

He puffed lazily on a tobacco pipe, his arms resting over the table, his gaze following Anne's every movement. He couldn't help but look bored, though—perhaps a little too used to the familiar sights of Nassau. But then, his eyes caught sight of you climbing the stairs into the tavern, your gaze locking with his. Jack raised an eyebrow, his lips curling into a mischievous grin. He couldn't help himself.

"Oy oy! What are you starin' at? You fallin' in love?" he called out, voice thick with his usual cocky charm. His fingers drummed against the table, amused by your eyes locked on him.