Chancing Fate - Jack Sparrow x OC

Part 1 - Chapter 5

The sun was low in the sky by the time Caroline spotted the first signs of Tortuga. After nearly two full days out at sea with only Jack and Will for company, she was almost glad to see land. However, she had heard enough to know the type of place they would be landing in, and it had never been high on her list of places to visit. In fact, it would probably be listed somewhere near the top of places she would never willingly go, yet here she was.

The island sat dark against the horizon at first, little more than uneven shapes and scattered lights in the distance. But as the Interceptor cut closer through the water, more details slowly revealed themselves. Lanterns flickered along the docks. Buildings crowded tightly together near the shoreline. Smoke drifted lazily upward into the evening sky while distant sounds began carrying across the water.

It seemed fitting somehow, having to spend the night in an awful town after spending all the daylight hours in her own personal hell. True to their word, she had spent much of the day paired with each of them, learning tricks and lessons to use later on. The previous afternoon had only allowed brief conversations and scattered instruction. Today had been entirely different with nothing ahead of them but open sea and time.

The morning had been spent with a sword in hand, taking swings at Will as she adjusted to the unfamiliar weight she was expected to control. The first hour had been manageable enough, focused mostly on remembering old lessons and letting her muscles fall back into movements that still felt faintly familiar. Of course, that had not come without corrections. And once Will seemed satisfied enough with her grip, he wasted no time putting her on the defensive.

That was when everything began falling apart.

It had started simply enough. Small strikes. Straightforward blocks. Controlled movements. Then Will began moving faster.

There had been no shortage of encouragement. Despite her struggles, he always corrected what she needed to alter, where her footing should shift, how she needed to move differently to absorb impact instead of fighting against it. But positioning was only part of the problem. Her labored breathing and shaking arms made the rest painfully obvious. This sort of physical strain was nothing she was accustomed to. Every strike she blocked threatened to buckle her arms inward, and she knew the entire time that Will was still holding back.

“Don’t lock your elbows,” he corrected again after another harsh impact rattled painfully through her arms. “You’re taking the full force of it.”

“I noticed,” she snapped between breaths.

Will only sighed patiently before stepping closer and nudging one of her boots farther back with his own. “Wider stance.”

She adjusted reluctantly, fingers tightening painfully around the hilt. Even the leather wrapping had begun rubbing her palms raw after hours of gripping it.

Again and again, he struck.

Again and again, she blocked too slowly.

The worst part was not even the exhaustion. It was how quickly her body betrayed her. Her shoulders burned constantly now. Her wrists ached every time steel collided with steel. More than once, the force behind Will’s strikes nearly knocked the sword from her hand entirely.

And every single time she reacted too slowly, embarrassment followed close behind.

There had been one particularly humiliating moment where Will disarmed her completely. The sword had flown from her hand and clattered loudly across the deck while Jack, seated near the helm at the time, looked up just long enough to witness it.

She still regretted how quickly heat had flooded her face.

To Will’s credit, he had not laughed. He simply retrieved the weapon and handed it back.