Harry Hook x Reader One shots {Happy to accept requests}

Harry x Assassin in the Isle

A/n: i know this is a little out there but I kinda liked the idea

Being descendant of the Cheshire Cat made you the perfect assassin. You are light and quiet on your feet, can see in the dark and are very calm and emotionless majority of the time. You would receive names in an envelope which was slid under your door along with some sort of payment, whether it be food, money or jewellery. From the decadent envelopes you soon learnt that your customer was someone from Auradon. But you were getting paid so you didn't ask questions.

Majority of your kills were lesser known people who could disappear of the grid without to much hassle making your kills easy and quick. You had never gotten anybody who was really dangerous and well known. Until one day when you had accidentally fallen asleep on your hidden outlook on your roof. You woke up during the night shivering and climbed down to your front door. As you shut the door and turned around you heard the noise of metal. You look down at your feet and see a bag of coins and an envelope. You carefully opened it and your eyes widen as you see Harry Hook written on the page in elaborate hand writing. Harry Hook was a big name around the Isle as he was Uma's first mate. And Uma rules the Isle. You were hesitant about taking the case, but after you counted the amount of money you were paid you decided to go through with it in the morning.

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Time skip
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You woke before sunrise and strapped a dagger to your arm, leg and ankle before making your way to Uma's ship. You waited in a hidden part of the docks before Harry arose from below decks. You trailed him to the fish and chip shop and sat at a table up the back to watch him. He ate breakfast before Uma was by his side and whispering things in his ear. He gave her a nod and made his way out of the shop, grabbing his sword. You were quick to follow.

You followed Harry around for the rest of the day, looking for opportunities for your assassination. It was only when it started to get dark that you followed him down an alleyway that lead to a dead end. As he reached the wall he turned around and looked you in the eye.
"Tell me lass, am I so intriguing that you couldn't help yourself but follow me all day?"
You roll you eyes and pull out your dagger from your arm, spinning it quickly in your fingers first.
"I have other intentions, but don't worry I plan to make it quick."
He chuckles and pulls his sword out from his belt.
"Oh you will have to do more than that to get to me." He gestures towards your dagger. You gave him a 'try me' look and he lunges at you with his sword. You swiftly dodge his attacks, staying light on your feet and would use the small dagger to stop the sword from coming down on top of you. After about 10 minutes You managed to get a scratch on Harry's cheek with your dagger, taunting him. He got more angry with you. After more scratches and cuts, his anger slowly turned into desperation as he started to realise the seriousness of the situation. In one last movement you took his feet out from underneath him and pinned him on his back on the floor. He tried to struggle but it was no use. He looked up at you with fear in his eyes. As you brought your dagger up to his throat he suddenly looked like a young child, trapped and afraid. He pressed himself as far away from the knife as possible and you saw the acceptance start to creep into his eyes.
"Just please, make it quick." It was barely a whisper. It sounded like a person who had given up. A person who wanted out of life, and it made you stop and stare at him. Your knife was still at his throat and you still had him pinned but you couldn't bring yourself to kill him. Your emotions started to rise as you watched Harry. Your heart started beating fast and you quickly jumped off Harry. He let out a sigh of relief and looked at you surprised. You look at him lost behind you sprinted away and climbed on top of an abandoned building. You sat down and brought the knees up to your chest. Tears silently streamed down your face as Harry's reaction replays in your head. You had broken down an unbreakable pirate and made him vulnerable, but you couldn't kill him. You just couldn't do it. Your heart started beating crazy every time you thought about being as close to him as you were.