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…

Author's Note: Thank you to all my reviewers. Hope you all continue to read and review. On that note…Chapter 2!

Chapter 2: An Evening with a Sparrow

The evening arrived rather quickly and Gwyn was sitting on a bench outside The Faithful Bride. It was going to be a night of flirting, flaunting, and sex once again. She didn't mind the flirting and flaunting so much. That was almost second nature to her. It was the whole idea of sleeping with drunken pirates that disturbed her. Nine years as a whore and she still couldn't comprehend the idea very well. It wasn't an uncommon situation.

Gywn took in a deep breath and stood from the worn out bench. It was time to get to work. The only relief for her was that she didn't have to stay in the whorehouse and wait for grimy men to come to her. She had a little more choice while working in a bar. Not many choices, but it was better than being assigned to someone.

As she opened the door to the Faithful Bride and entered, she was shocked to see that no one even looked up. Usually when a whore entered, all the men were drooling like animals. It must have been an off night or something. Gwyn shrugged it off and made her way over to the bar. Her boss, James, was standing behind the counter and cleaning out a glass that he would soon fill with rum for a customer. "Gwyn, you should be working the tables," he said without taking a single look at her.

"I just wanted to come over and say hello. You are my boss after all," she replied.

"You know that I don't care whether you come into work or not. It's your life and you pay me the rent. You come up short…you're out on the streets. You're not my problem, Gwyn."

"James, I-"

"Get to work!" She jumped at the sound of her boss' shout and backed away. Gwyn had always been a hard worker for James, and she gave him more respect than any of the other whores. Still, he couldn't care less about whether or not she was alive or dead. It didn't seem fair. Yet, she couldn't argue. This was her life.

Gwyn's eyes traveled the room slowly. Most of her fellow workers were sitting on the laps of grimy pirates and holding back looks of disgust. She shook her head slightly and began to walk through the crowds of people. Suddenly, a man flew across the room and landed at her feet. She jumped and then quickly stepped over him and leaned against a wall. She took a deep breath and then looked down the stone flight of stairs on her left. After glancing around the room again, she strolled down the stairs at a leisurely pace, hoping to catch the eye of someone. She knew that even if she did end up with some nasty pirate or local drunk, at least she was getting paid for it.

She managed to avoid the groups of people fighting and knocking each other down and made it over to the other side of the room. She braced her hands on an empty table to expose her cleavage a little more and looked around. No one even looked up. She knew that this night was going to be pure Hell if she couldn't even get one man. "Damn it all," she said to herself as she turned around. She almost jumped when she did.

"Well, Gwyn…how lovely to see you again," the man said, grinning an awful smile of teeth that were beginning to rot.

"Hugo, right?" she replied.

"Did ye forget me name already, darlin'?"

"How could I? You slept with me last night and ripped me off." Gwyn placed her hands on her hips and stared deep into the eyes of a man who she resented with passion.

"Come now, dearie…you weren't exactly giving it your all."

"Just leave me alone," she replied as she tried to walk passed him. However, Hugo grabbed her arm and twisted it behind her back before pulling her against him so she was facing away from him. Her head was leaning back slightly over his shoulder and she was wincing at the pain shooting through her arm. "Let me go," she said quietly.

"Gwyn, I'm afraid that you owe me another night."

"I don't think so. You had your night and I don't service the same man more than once." Hugo leaned over and roughly bit down on her neck, causing her to yelp. "Stop!"

"I think it's time we-" Hugo stopped speaking when he felt a pistol against his temple.

"Now, now…I believe the young lady said no." Hugo turned his head to his right and his eyes widened at the sight of his attacker…Jack Sparrow.

"Jack, why don't you just mind yer own business for a change?" Hugo asked. Jack cocked the pistol and smirked. "Okay, okay…" Hugo quickly spat out. He released his hold on Gwyn and stormed off. Gwyn, on the other hand, was now leaning her head against the wall and taking deep breaths. She hated being handled like she was worth nothing.

"Love, it seems that we keep running into each other," the rogue whispered. Gwyn's eyes bugged out and she turned around with a sigh of relief.

"Captain Sparrow, what are you doing here?"

"Apparently coming to your rescue, love," he said while waving his arms around and a famous smile plastered on his face.

"Well, thank you again. But I must now take my leave. I have to get to work."

"And where exactly are you working?" Gwyn was shocked. Surely Jack should have figured it out by now.

"You mean you don't know?" Jack shrugged. "How could you not know, Jack? Don't you see what I'm wearing? I'm a whore. I work in the whorehouse usually. I only work in the bars a couple nights a week." Jack stayed silent and just stared at her. "And now I bet you want me to sell my body to you now too, right?" Gwyn asked as she averted her eyes. It was then that she felt a warm hand lift her chin. She once again found herself staring into Jack's deep chocolate eyes. His gaze was somewhat comforting, but terrifying all the same. He wasn't saying a word, and that's what worried Gwyn the most. She decided to break the silence between them. "What are you thinking?"

"Come with me, love," he whispered as he placed his arm around her waist and walked her over to a table in the back. He sat down and before Gwyn could react, he pulled her onto his lap. He felt her entire body stiffen and began to run his hand up and down her back. "Relax, love…just relax."

"I'm trying, M-Mr. Sparrow." Gwyn wrapped one arm around his neck to keep her balance and looked down at the pirate. He gave her a small smile and then leaned up to her ear.

"Listen carefully, love. I'm not going to hurt you." Gwyn swallowed a lump in her throat and tried to stay calm. "Just go along with whatever I do. This way you don't have to spend tonight with anyone."

"I…I need the money," she whispered back.

"I'll handle it, savvy?" Gwyn nodded slightly and almost jumped out of her skin when Jack began to suck on her neck. She was shocked, but it actually felt nice. Jack wasn't being rough with her. He was being sweet. But what if later he turned out to be just as perverted as the other pirates and drunks she dealt with everyday? What if he was trying to sleep with her and then rip her off? She had nothing to lose though…except her self-esteem and dignity. What the hell? I lost my dignity nine years ago she thought.

Slowly she began to warm up to Jack's offer. She began fiddling with the trinkets in his tangled hair, which turned out to be thick and soft. "Jack Sparrow!" a voice shouted. Jack turned from Gwyn's neck and gave her a squeeze on the hip to encourage her to keep up the act. She nodded and leaned forward to kiss his neck as she ran one hand up and down his chest.

Jack was busy looking up at a member of his crew. "What is the problem, Ragetti? Can't you see that I'm busy at the moment? And it's Captain…or have you forgotten?" he asked.

"Sir…the thing is…Barbossa sent me."

"What does he want now? We spent the day talking over mugs of rum."

"Captain, he believes that you should tell us more about the quest we're on. Where is the island, mate?"

"Ragetti," Jack began as he leaned into the ministrations that Gwyn was applying to his neck, "I already told you and the rest of the crew that I will get us to the Isla de Muerta. The treasure will be more than we've all dreamed of. Now if you don't mind, the lady and I have some business to attend to…so if you'll excuse me-"

"Captain," Ragetti said as he watched Jack stand up and hold Gwyn bridal style, "I fear that you may suffer a dangerous fate if ye don't start being honest with us, mate." Jack just let out a hearty laugh and walked up the stairs and out of the Faithful Bride. He carried Gwyn the entire way and walked into the whorehouse.

"May I help you, Captain Sparrow?" Jacquie asked with a seductive smile as she leaned over the counter. Jack turned to look at her.

"I'm taking Miss Gwyn here up to her room for a bit of fun, aye?"

"Oh, of course, Jack. Do have fun," she replied sweetly. Gwyn, of course, was now panicking. Jack had promised he wouldn't do this and now he was? She knew she shouldn't have let herself trust a pirate…even for a brief moment. It was all a huge mistake. Before she knew what was happening, she was staring at her bedroom door.

"This your room, love?" Jack asked. She nodded gently before Jack took his lead and kicked open the door, which Jacquie had unlocked once business hours truly started. He placed her on the bed and walked back to the door. He locked it and then turned to face Gwyn again. She wasn't on the bed though. She was standing against the wall by the window with a horrorstruck look on her face. "Something wrong, love?"

"Jack-"

"Captain!" he corrected with joy in his tone.

"Captain Jack," Gwyn said again, "You told me that you wouldn't do this and here you are in my bedroom! Why did you lie to me?" Her voice was trembling.

"Love, I'm not-ow!" Jack didn't even see it coming. Gwyn had walked forward and slapped him across the face. "I'm not here to sleep with you, darling."

"What?" Gwyn asked. She was completely confused now. Why would he have brought her back here if he had no intention of sleeping with her? Jack reached into a small pouch he kept under his belt and took out quite a bit of gold. He placed it in her hand and closed it into a fist. "What are you doing?" she asked.

"I only want your company…not pleasurable company, savvy?"

"W-Why would you do this? You're known for bedding the whores here, not talking to them."

"You seem like a nice girl, Gwyn. I know you didn't want this life, so I decided to give you a break from it tonight. You'll just have to put up with ol' Jack." Gwyn laughed at his words and threw her arms around his neck. Tears were pricking her eyes, but she wouldn't let them fall.

"Thank you, Captain Sparrow. Thank you so much. I can't even begin to-"

"Then don't," he said as he braced his hands on her shoulders and stepped back, "Let's just lay down on your bed and talk." Gwyn nodded and they both laid down on her old and worn out bed. "Not the most comfortable, aye?"

"Try sleeping on it every night, Captain. I'm surprised I haven't broken my back." Jack chuckled slightly and turned on his side so he was facing Gwyn. He braced one arm behind his head and stared down at her. He had to admit, for a whore, she wasn't terrible based on looks. She was fairly pretty. He had a feeling she was prettier, but it was hard to tell. She had caked on her makeup. "So, what would you like to talk about?"

"Well, for starters…you."

"Me?"

"Aye. How long have you been in Tortuga?" he asked as he waved one hand in the air.

"I've lived here my entire life. My family and I owned a small house on the other side of the island. Then one day, when I was sixteen…they disappeared." Gwyn averted her eyes and fiddled with the thin blanket on the bed. "They were just gone. No letter saying where they were going or when they were coming back."

"So you chose to come and work here? You didn't think of traveling to another port and starting a new life?"

"What real business would hire a sixteen year-old girl from a pirate island? I didn't know where else to go. It's not like I wanted to become a whore, you know. I hate this job more than anything in the world. Sometimes I think about just slicing my wrists, but then I realize that I couldn't bear to kill myself. I'm not worth much, but I'm worth more than that." Jack slowly reached out and brushed a stray hair from Gwyn's face as she continued to speak. "I just wish that all of this could go away. I never wanted to sell myself and live this life. I guess when you're young, you make foolish choices."

"Dearie, you did what you could to survive. Your family leaving you…well…it wasn't right. Still, I know you can do better. I wish I could help you, I really do. I'm leaving tomorrow."

"Where are you going, Jack?" she asked as she looked up at him. Jack was tempted to correct her for not calling him captain, but he let it slide and smiled down at her.

"I'm heading to an island…and island that cannot be found except by one who already knows where it is."

"I imagine there's a valuable treasure buried there."

"The treasure of Cortez. Aztec gold, love…mountains of gold." Gwyn smiled and leaned her head back on her pillow, her eyes staring with wonder up at Jack. "I can't wait to set foot on that island and claim one of the greatest treasures of all time."

"Sounds wonderful," she replied with a soft yawn as she curled up closer to Jack and closed her eyes.

"It really is, love. I don't think I've ever been so happy in my entire life. I'm the captain of the Black Pearl thanks to ol' Jones…and I'm one handsome devil if I do say so myself." Jack smiled to himself and absentmindedly put his arm around Gwyn and caressed her shoulder. "It'll almost be as joyous as the day I sacked Nassau Port. I didn't even fire a shot. Can you believe that, love?" No answer. "Love?" Jack asked again. He looked down at Gwyn and couldn't believe what he saw. She was sound asleep! It was the first time that any woman had fallen asleep during one of his stories. She looked so peaceful. "Goodnight, love," he whispered before closing his eyes. He needed his rest.