The Crimson Cutlass eased towards the dark silhouette on the horizon. The Isle of Shadows was exactly the kind of place that would have sent any sane person turning their ship the other direction. Jagged black cliffs rose like teeth from the ocean, shrouded in mist. The trees beyond were gnarled and twisted, their canopies forming a shadowy green wall. Even the seabirds circling overhead here looked meaner, sharper beaks, hungrier eyes. 

Naturally, of course, Vail loved it. 

She was already lowering the longboat into the water by the time Tom had finished checking their gear. He climbed in after her, wary but resigned to the adventure. 

“You know,” he said as he rowed them ashore, “This place looks like every bad idea in a holonovel rolled into one.”

“Exactly,’ she said, grinning, “It’s perfect.”

The boat scraped against black sand. They disembarked, their boots sinking slightly into the gritty earth. Ahead of them, a half-buried stone arch marked the beginning of the jungle. Moss-covered etchings covered its surface – faces of old gods, perhaps, with wide, hollow eyes. 

Tom stepped closer, brushing his fingers over the etchings. “Holodeck program’s got decent attention to detail,” he admitted.

“Don’t act like you’re not impressed,” Vail replied with a smirk 

He gave her a sidelong look, and the corners of his mouth curled up into a smile. 

They entered the jungle. The canopy swallowed the sunlight, dimming the path ahead. Vines hung like curtains, and strange bird calls echoed in the distance. The air was thick and humid, clinging to their skin. 

Within minutes, the island began throwing obstacles at them. First, there was the quicksand. Vail nearly stepped into it but stopped short when Tom’s arm shot out, blocking her. “Ground’s too soft,” he warned. 

She crouched, poking the ground with the toe of her boot. The sand shifted and bubbled ominously. “Nice catch,” she said. 

“Stay close.”

“Oh, I am close.”

Then came the bridge, if you could call it that. A series of half-rotten planks stretched over a ravine whose bottom was lost to the darkness. Vail went first, leaping from plank to plank like a cat. 

“Come on, Grey Tom, try to keep up!” she called over her shoulder. 

Tom followed, more carefully at first, then, realizing the planks were giving way, sprinted the rest of the distance in a blur of speed that made Vail laugh. 

“You’re faster than you look,” she told him. 

“You’re reckless,” he responded.

She shrugged. “Part of my charm.”

The jungle around them only got stranger.

At one point, a flock of brightly coloured parrots dive-bombed them, shrieking insults at them in three different languages while they snatched at anything shiny. One actually grabbed Vail’s cutlass and tried to fly off with it. She leapt, caught the bird in mid-air, and yanked her sword back. “Not today, featherbrain!”

Tom snorted despite himself. 

Finally, after what felt like hours of traps, vines, and monkey harassment (one particularly bold monkey stole Tom’s tricorn hat and wore it proudly from a tree), they reached the heart of the island. A massive stone chamber lay ahead, half buried in roots. Torches flickered to life along the walls as the ducked inside. At the very center of the chamber stood a pedestal, and on top of that, a heavy, ancient-looking chest. 

“Well,” Vail said, clapping her hands, “There’s our payday.”

They approached together. The chest was sealed with a complicated puzzle lock – rotating rings etched with symbols. Tom crouched beside it, fingers brushing the carvings. “It’s a code,” he murmured, studying the sequence. 

“Can you open it?” Vail asked. 

“Of course,” he said, already twisting the dials into place with focused precision.

While he worked, she wandered the chamber, tracing her fingers along the stone walls. “You know,” she said, “This is the part of the story where the hero and heroine are supposed to share a moment.”

He didn’t look up. “Hero and heroine?”

She shrugged, smirking. “Depends on who you ask, which of us is which.”

There was a soft click as the last ring fell into place. Tom exhaled and glanced up. “That’s it. It’s open.”

They both reached into the chest a the same time. Their hands brushed. 

Vail froze, her grin softening for just a moment. “Tom,” she said quietly. 

He held her gaze, his expression unreadable – but there was something in his eyes, something warm that cut through the harshness they usually carried. Slowly, he leaned in and kissed her. 

When they pulled back, Vail said, “See? I told you pirate stories can be romantic.”

He was about to reply when the holodeck flickered.

The torches dimmed. The walls shifted. For an instant, the jungle outside flashed back to a wireframe grid before snapping back. 

Vail’s smile faded. “… that’s not good.”

Then, a new voice echoed through the chamber. 

“Well, well,” it drawled, “looks like you found my treasure.”

They turned in unison towards the chamber’s entrance. Blacktooth was back, but this time… he was different. His eyes were sharper. His movements were more precise. The way he stepped into the torchlight wasn’t the stiff, pre-programmed swagger of a Holo-NPC. 

The holodeck’s failsafes had indeed failed. 

[I know, typical right?]

Tom stepped in front of Vail, his hand tightening on his cutlass. “Stay behind me,” he murmured to her. 

“Not a chance,” she whispered, drawing her own blade.

The chamber filled with the sound of approaching footsteps – Blacktooth’s crew, moving with a new, unsettling awareness. 

Vail smirked, but there was an edge to it now. “I guess we’re finishing this the hard way.”

Tom’s grip tightened again. His blood was humming, Klingon instincts rising.

Blacktooth smiled, half-teeth and all hatred. “Ready to die, Redfang?”

Tom answered, his voice low and dangerous. “No, but I hope you are.”