Boots Made for Walking

A fan fiction based on Pirates of the Caribbean. Story starts before "The Curse of the Black Pearl," but may travel through the movies later on.

Disclaimer: I do not own anything by Disney, Gore Verbinski, or Jerry Bruckheimer.

Rating: M

Summary: Gwyn Thompson has been a whore in Tortuga for 9 long years. She meets Jack Sparrow and stows away on his ship, hoping to find adventure with this intriguing rogue. Little did she know that this would be a journey she'd never forget…

Chapter 3: Stowaway

Jack stood at the helm of his precious Pearl. It was already afternoon. He and his crew had departed Tortuga in the early morning hours and made a quiet exit at that. He didn't want any other pirates to follow him if they happened to hear where he was heading and what he would find there. He delicately held the helm steady before turning it a few times to the right. He then steadied the wheel and stared out at the horizon line. This is what he loved about being a pirate…his freedom.

A small part of him realized that he was missing something though. He had cringed when he left that morning, knowing that he was leaving an innocent woman behind. She may not have been innocent in a physical sense, but she still had the innocence of a girl hidden beneath her dark lashes. It was intriguing to him, but at the same time it was all too ordinary. Ah well…I'll never see that lass again he thought.

Down in the cargo hold of the Black Pearl, Gwyn was huddled up behind a large quantity of crates and barrels. Her knees were drawn up to her chest and she was shivering. Water was slightly leaking in through small holes in the ship whenever a strong wave was hit. She was soaked from head to toe and knew that she couldn't take much more of living down in this dank place. Half a day hadn't passed and she was already losing it. It was dark and cold down there.

Gwyn still didn't fully understand why she had stowed away on Jack's ship. She had awoken to an empty bed when the sun was rising. By the time she had made it down to the docks, the Pearl had just cast off. Luckily she was a fairly good swimmer and managed to catch up to the ship before it had gotten far. How she had been able to sneak by Jack and the crew was beyond her comprehension, but she had made it to the cargo hold without a problem. Her only issue now was that she was cold and hungry. Sooner or later she was going to have to emerge and reveal herself to Jack…but not yet.

"Who are you?" a voice shouted. Gwyn jumped to her feet and then stumbled backwards over a crate. She smacked her head against the side of the hull and winced. "I say again, lass…who are you?" Gwyn stared up at the man and tried to scramble along the side of the hull to get away. It wasn't that the pirate scared her. He was actually a decent looking man. His long dark hair contrasted nicely with his glowing blue eyes, and his clothes weren't terribly worn out. He was older than Jack by at least ten years…maybe more.

"Sir, I…"

"You stowed away on this ship, didn't ye?" Gywn nodded. "Alright," he began as he reached down and picked Gwyn up by one of her arms, "Time to take ye to the captain." He pulled her across the floor, and she struggled the whole way. She wasn't ready to face Jack. What if he got angry at her for stowing away on his precious Pearl? What if he threw her overboard for this? Either way, it wasn't a win-win situation.

"Let me go!" she screamed as the pirate began dragging her up the stairs. She tried desperately to wriggle free by kicking her legs and pulling in the opposite directions. "I didn't mean any harm! Please! LET GO!" Before she knew what was happening, she was being yanked across the deck of the Pearl toward the helm. Her frightened eyes scanned the open deck and she found herself shaking even more. Grimy and ruthless pirates were eyeing her like a piece of meat. This can't be good she thought.

"Oi, Bootstrap! What you got there?" a slurred voice shouted. Gwyn gasped and tried to hide her face beneath her long hair. She kept her eyes focused on the wood beneath her feet until she saw a flight of stairs in front of her.

"Found her in the cargo hold, Jack. She stowed away when we made port in Tortuga."

"Ah," Jack said as he raised one hand in the air and swaggered down the stairs. Gwyn felt her heart race again. Jack was going to kill her. It was the only obvious choice. She had overstepped her boundaries by sneaking onto his ship without asking for passage. When she saw a pair of brown boots standing at the bottom of the stairs, she steadily raised her head and looked into Jack's eyes. "Gwyn?" he asked.

"Nice to see you, Captain," she replied, her eyes pleading for him not to hurt her.

"Jack, what should we do with her?" the man known as Bootstrap Bill Turner asked as he lifted Gwyn up so she was standing up straight.

"I say we throw her in the brig and then let her out for playtime!" Ragetti said joyously as he walked up behind Gwyn and started fiddling with her hair. An eruption of laughter came from the crew.

"I say we tie her up and toss her over, Cap'n!" the greasy man known as Pintel stated, causing more laughter. Gwyn began to feel completely violated and looked around with an expression of innocence. The pirates were laughing at her; all but Jack and Bootstrap. She gazed up at Jack and swallowed a lump in her throat before noticing that Jack was gesturing for her to do something about this. He didn't like her being treated this way, but he couldn't very well just stop all of it either. Gwyn took a deep breath and nodded once to the captain.

"She's a worthless whore, Cap'n," Barbossa stated from the helm, as he was steering, "Might as well toss her. She ain't that good in bed for what I 'eard in Tortuga."

"Alright…that's it!" Gwyn screamed as she stomped down hard on Bootstrap's foot, causing him to release his hold on her. She reached out and grabbed Jack's sword before turning around and facing the crew. "What the hell is your problem, gents?" she asked, completely outraged. She narrowed her eyes, which were now more silver than grey. "Who shoved a pistol up all yer asses? You never speak to a lady like that!" Jack was smirking at her. She was amusing now that she was showing some spine…and he liked it very much.

"Maybe we should teach ye a lesson, poppet," Pintel stated as he unsheathed his sword.

"Bring it on, fat boy!" she yelled as she braced herself in a fighting stance. The crew backed away, knowing that this whore would be on her back and begging for mercy within seconds. No point in wasting their time helping Pintel. There was no way she could fight. She was thin and acted helpless. Gwyn stayed still until Pintel charged at her. She simply stepped to her left and watched him run into the railing of the stairs. A round of whispers seemed to echo across the sea…along with some muttering "That musta hurt."

"Alright, poppet," Pintel complained as he regained his balance and turned to face Gwyn again, "Time for ye to learn a lesson!" He charged again, but this time Gwyn held up Jack's sword and blocked his swing. She stumbled a bit and her legs shook, but she stood her ground and pushed the pirate back. "Ye shouldn't know 'ow to do that!"

"When you live in Tortuga, you learn a lot about pirates and their swordplay," she replied with a smile as she lunged at Pintel and met him blade-to-blade. The two stared at each other for a while. It was like they were trying to look into each other; like they were looking for their adversary's next move. "Now take back what you said about me."

"I won't apologize to a lady like ye!" he shouted as he pushed Gwyn back and began to fight more fiercely. Gwyn was shocked at how insecure this pirate was. He was a fairly good fighter as well. The only problem with fighting this man is that Gwyn didn't know how long she could last. She had been taught the basics of swordplay, but too much fighting would tire her and she'd be killed. It wasn't an ideal situation.

Jack could see that as Pintel began giving Gwyn more challenging strikes to block, the more she was tiring. He knew he would have to stop this battle before someone lost an arm or a leg. He watched Gwyn duck another heavy blow from his crewmember and began to feel pity. This whole fight was partially his fault. He had given her a look that said "start some trouble" loud and clear. This was getting to be too much to deal with.

Gwyn dove on the ground when Pintel swung around and almost took her head off. She landed hard on her stomach and rolled over with just enough time to block her adversary's sword once more. She felt sweat dripping from her brow into her eyes and didn't know how much longer she'd be able to keep herself focused. She was so exhausted and felt as if she was going to die. "Alright! That's enough!" Jack shouted. Gwyn sighed in relief.

"But, Cap'n…can't I just-?"

"No! Now sheath your sword, savvy?" Pintel reluctantly put away his sword with anger gleaming in his eyes. Jack knelt down and took his sword from Gwyn's shaking hand before helping her to her feet. "I think you've proved yourself, love. You're coming with me." She winced as she took a step and leaned further against Jack, her hands gripping his jacket with the Jaws of Life. Jack smirked and then felt all eyes on him. He looked at his crew and noticed that they were all staring. "On deck, ye scabrous dogs! Back to work!" They all immediately scattered and went about their business.

Gwyn let Jack walk her into his cabin and let out a huge sigh when he sat her on his bed. She almost fell onto her back like a doll, but Jack kept her steady and held her against him. His eyes traveled over her body and he smiled a toothy grin. She was sweating like a pig and her makeup was running all down her face, partially from being in the damp brig for all those hours. "You need some cleaning up, love. You're a mess."

"Thanks," Gwyn muttered, trying not to laugh since she knew that she looked terrible as it is. She watched as Jack walked over to a cabinet and opened it. He pulled out a bucket and grabbed a cloth from his desk before walking back and sitting down next to her. He dunked the cloth in the water and wrung it out. When he reached out to dab the cloth on her face, Gwyn slightly moved away.

"Dearie, I'm only trying to help." Gwyn eyed him carefully, even though she knew that she could trust him. He hadn't killed her for sneaking onto his ship. He had seemed amused by her stunt. Reluctantly, she nodded and let Jack run the wet cloth over her face. The water was a little warm, but it felt so good…so refreshing. She closed her eyes and let him continue.

Jack carefully looked over Gwyn's face as he cleaned her up. Underneath all that makeup was a delicate flower. Her skin was a light tan that complimented the grey eyes he remembered from Tortuga. Her lips were a soft, pale pink underneath all that crimson rouge she wore. It was amazing. Jack had never seen a whore without makeup. He removed her eyeliner and almost instantly she opened her eyes. Jack's heart could have stopped. She wasn't pretty…she was drop dead gorgeous! She looked so much better without the mask she had been forced to put on for so many years. "What are you staring at?" Gwyn asked, noticing the pirate studying her face.

"It's nothing, lass. I'm…I'm just shocked at how amazing you look. You should never wear makeup again." Gwyn felt her face flush a little and averted her eyes.

"I'm not that beautiful, Captain Sparrow. I'm…I'm decent."

"Bollocks! Any man would have to be a complete git not to see that." Both of them started laughing softly, except for a slightly louder outburst by Jack. "So…you decided to follow me, love?"

"You said you wanted to help me, Jack. I figured you wouldn't mind if I came along. I couldn't bear living in Tortuga anymore."

"You still should 'ave come to me instead of stowing away below deck. Suppose someone else had found you? Bootstrap Bill isn't a cruel man. He's like me brother. But if it had been someone like Barbossa or Ragetti…you might not be in such good shape."

"I…I never thought about that," Gwyn said as she looked back at Jack and gave him a sincere smile.

"You can stay for now, but I think you'd be better off in a place like Port Royal or something. After we find the treasure, I'll take you somewhere better and make arrangements, savvy?" Gwyn's smile grew and she gently leaned her head on Jack's shoulder. "I take that as a yes?" he asked.

"Yes."

Author's Note: The story is going to start moving rather quickly soon because I have decided that it will also follow The Curse of the Black Pearl, Dead Man's Chest, and also the third movie when released next summer, which I am guessing will be called World's End. I mean, I can't go through ten years of life and then the movies. It would be too long. However, there will be a couple more chapters before The Curse of the Black Pearl.