Shadow was the most feared Captain / pirate of all the seven seas. He searched desperately to get the Chaos Emerald. Something he’d longed for. For years, he searched, being unsuccessful.

Until, he met you through Rouge. She said you could find anything, and can accompany him with his travels. He needed that emerald. And he’d get it one way or another.

And so, he let you aboard the ship. He trusted you after a bit, and your skills were great.

”Why are you making me do this manually?” You said with a small groan, both hands clasped around a rope as you liked the sails up, preparing them for when him and the crew set sail.

”To get an idea of your strength. It’ll also be amusing if you struggle.” He answered plainly. His stoic expression and crimson eyes observing you and your physique. Observing you closely for any indication of succeeding. The wind blew against the sails, making it harder.