(A/N: Warning, There's a small, possibly triggering part mentioned in this chapter that may be a bit explicit for some. Just thought I'd put a warning here.)

It was the next afternoon and the evening of Jack's date was approaching quickly. He spent a while in the bath, cleaning up weeks, or months worth of stink, dirt, and grime. He then got dressed in whatever shirt had the least amount of visible holes in it, his best breeches and waistcoat, and put on the only pair of boots he owned and his belt. He brushed his hair as he heard pounding on the washroom door.

"WHAT?" Jack yelled through the door.

"I need to pee!" It was Valerie.

"You just went pee before I came in here!" Jack complained as he continued to brush his hair.

"Well, I have to go again!" Valerie began pounding on the door again, making Jack wanting to rip his hair out in frustration.

Jack topped off his look with the cleanest bandana he could find. He tied it around his head and adjusted his hair, properly laying it over the bandana. Jack threw the door open while Valerie was in mid-pound and got him right in the face.

"Ouch! Are you trying to give me a bloody nose right before I have to go out?!" Jack fumed, rubbing his face.

"Well, I have to pee!" Valerie shouted.

Jack marched past her and he was pulled back by the arm.

"Wait," Valerie stopped in a change of tone. She put her face up close to Jack and sniffed. "You smell...good?"

"Yes, so?" Jack retorted. "A man deserves to be clean once in a while!"

"Keep calling yerself a man, it's never going to happen," Valerie said, shaking her head.

"GO PEE!" Jack snapped. He pulled away from her and took off downstairs.

"Ugh, her bladder is the size of a bean!" He grumbled to himself as he was careful to tiptoe through the living area.

The room was only lit by a couple of lanterns, and some of the family were passed out on the couches or the floor. He got to the stairs going down to the Great Chamber when he felt a knife quickly whistle past his ear from behind and stuck to the wall in front of him. Jack whirled around to see Grandmama in her usual rocking chair.

"Teague! Your misbegotten whelp is trying to escape!" Grandmama yelled out, glaring at Jack.

"Escape?! Am I caged here like some bloody animal?!" Jack accused angrily.

Teague went down the stairs as Jack and Grandmama drew their attention to him.

"What is your business leaving, boy?" Teague questioned, folding his arms and looking down at Jack.

"Well, I'm leaving to go...um...go out with some friends!" Jack answered, attempting to lie his way out.

Teague raised an eyebrow. He looked at Grandmama, back at Jack, then back at her and they both laughed. Jack frowned at their response. Teague and Grandmama slowly stopped laughing and looked back at Jack, who was glaring at them.

"Oh, you were serious?" Teague said flatly.

Jack folded his arms and raised an eyebrow back at Teague.

"So my Jacky-boy has friends now? That's great!" Teague beamed.

Jack then turned to the stairs "Alright, I've gotta head out—"

"Wait! Since you have...'friends' now, what are their names?" Teague asked curiously.

"Uh..." Jack turned back to Teague and looked around the room, searching for some sort of answer. He spotted Uncle Jack sitting up in the corner, passed out drunk with a half-eaten sausage still in his hand. Jack looked at the sausage and back at Teague.

"Um...Richard,...Willie, and Johnson! Those are my friends' names!" Jack replied semi-confidently with a fake smile.

The room was silent. Jack gulped as he feared Teague would catch on. Instead of raging, Teague smiled again.

"Alright, Jackie. Don't be gone for too long," Teague reminded him.

"I won't...unfortunately," Jack mumbled the last part under his breath as he went downstairs and ran out of the Great Chamber, on his way to the brothel.


The Madams at the brothel went to work on Jack as soon as he arrived, straightening out his clothes and hair, and hyping him up for the big date.

"Are you nervous for tonight, Jack?" Lavina asked, sitting next to Jack on the couch smiling. The other girls caught her up on what has been happening with Jack.

"Me? Nervous?" Jack replied quickly. "No, no, no, no! I'm fine—dandy even! Not nervous whatsoever, lass!"

"Aw! Jackie's sweating!" Abigail giggled, taking a handkerchief from her petticoat and wiping his face.

"Okay, fine! I'm a little nervous—just a little bit," Jack admitted, putting his hands up. He then felt a spirt in the face. He coughed and his eyes watered from the spray.

"Sorry!" Claire apologized, holding a small perfume bottle. "It's a new thing called...cologne. It's like perfume!"

"Remember, she's the first priority, you're the second priority," Lavina lectured.

Donna took a seat next to Jack, on the other side of Lavina. "Right! Don't hit it and quit it. It's all about making her feel good."

"Keep it at her pace, don't rush her," Abigail continued.

"And if she's concerned about size, remember that it's not the size of the boat that counts, it's the motion of the ocean!" Claire interjected.

All the girls giggled at Claire's contribution and Jack spoke up. "Do you all really think I'm going to bring her to bed on the first date?"

The girls silenced and stared at each other with confused looks, as if they have never heard of the concept of not sleeping with a partner on the first date.

"Okay! If she wants to do anything, remember what we taught you," Lavina smiled and winked.

Donna and Lavina got up from the couch and helped Jack up. Abigail brought out a picnic basket.

"Here! There are sandwiches in there, chocolates, glasses, and a bottle of wine," she said, handing the basket to Jack.

Jack walked to the door followed by the girls, and stealing a handful of flowers from a vase on the way. The girls walked Jack out of the door and cheered as he waved and made his way down the street.

"Bye, Jackie!"

"Have fun!"

"Remember what we taught you!"

"Go get 'em, tiger!"


Jack went around to the other side of the island, opposite from the tunnel the ships entered through. Usually on that side of Shipwreck Cove, there wasn't a way to get down to the water. However, Jack had found some caves that led him behind a cliff, climbing down the narrow caverns until he got to the bottom where it opened up to a little beach. His boots sunk into the sand as he surveyed the area. The sands were white and the water was a turquoise blue, however the waves weren't very nice around the Cove and it was advised to not go swimming in them, although Jack did anyway.

He was nervous about whether Anne would show up or not, or if she was able to find the place or if she got lost. This was the first time Jack had ever revealed any of his secret little inlets to anyone.

He looked to the left and saw her in the distance looking out to the water. She looked absolutely gorgeous in her pink gown, and the front of her long brown hair was braided and tied to the back, letting the rest of it out blowing in the wind. She looked over to his direction. Her slightly freckled face lit up as she waved him down. Jack smiled and ran down the beach towards her, with the flowers and basket in hand.

They had set up a little picnic area in the middle of the beach. Jack pulled out the sandwiches and chocolates, and poured glasses of wine. Things were quiet at first, but after finishing the first glass, they began to strike up a conversation.

"So, Jack. What do you do?" Anne asked as she looked at him with her beautiful light brown eyes.

"What do I do?"

"Yes, as in like—what's your story?"

"My story...hm..." Jack thought for a minute, staring off into the distance with a finger on his chin. "Well,...a long, long time ago...there was my mum, below deck of a ship in the middle of a typhoon. She was screaming...and crying,...and there I was! I WAS CHARGING MY WAY THROUGH AND—"

Anne interrupted him, bursting into laughter. "Hahaha! NO! Not your life story! What do you do now!"

"Oh bugger! I was going to publish that into a book!" Jack laughed jokingly.

They both wept in laughter together. It was apparent they were a bit tipsy off the wine. They finally gained control of themselves when Jack found something to say.

"Well, in all seriousness," Jack began. He wiped his eyes with his sleeve, still recovering from their fit of laughter. "I, for the most part, have lived here in Shipwreck Cove my entire life. I've been on and off of ships starting from a very young age."

Jack looked at Anne, who was staring intently at him, listening to every word he said. He felt proud to finally feel like the center of attention rather than being in the shadow.

"When you say you've been on and off of ships, you take trips often? Where have you gone to?" Anne asked, intrigued.

"Sort of trips," Jack answered. "Like most everybody else on this godforsaken island, my whole family is a bunch of cutthroats, criminals, scoundrels, drunkards, pillagers, and pirates. Some are even Pirate Lords," Anne's eyes lit up at the mention of Pirate Lords. Jack turned and looked out at the sun, which was barely above the tall mountains of the island that enclosed Shipwreck Cove, as he went on.

"They're now more 'sit-at-home' pirates, and I nowadays mostly employ onto my da's ship, or ships of other Pirate Lords we are friends with, but when I was just a little shaver, we would all sail aboard dear old Grandmama's ship as a family. They were disguised as family vacations for us younger ones, me and my cousin Valerie. Although in reality, it was all pirating business. Pillaging and plundering, looting, and Valerie and I had even watched some towns get sacked from the ship. As a family, we also sailed across oceans to many counties visiting different Pirate Lords and such. Throughout our journeys, Val and I had seen and heard things no young one should ever have to see or hear, but that was all we ever knew.

Only once in a while did any of the exciting stuff happen though. Most of the trips were just smuggling, and all around just underground illegal activity. We often went to other pirate havens that were like here or Tortuga, but they were smaller and more unknown. The activities at those places were much more gruesome and shady. They were even rubbed off of most maps making them impossible to find. Here, would be just all your normal taverns, pubs, gaming houses, brothels, and the like. The worst you would see on the streets here is the occasional silly drunk pirate, stumbling and throwing up, or some washed up, nearly naked prostitute at the side of the road. On the streets at the towns we went to, there were bodies on the streets. Some were clothed, some were naked, some missing limbs, and some were still twitching. My da' often covered our eyes with his hands when we walked through those streets, but sometimes, I could see through the cracks between his fingers."

Jack looked over at Anne with wild eyes as he continued to tell his story.

"There was one particular town on an island I loved going to. It was probably because there weren't as many bodies on the streets so we didn't have to have our eyes covered very much. It didn't mean that town was any better than the others though. I don't really remember the name of it since I was so young. The last time I went there, I was probably about five or six, and Valerie was about seven or eight. I remember it was that time in particular when we had went to smuggle rum because a family friend was with us. He was in the Royal Navy, but he was also in the rum smuggling business and he often helped us out.

Me, Val, Da', and this family friend, we all went to this little broken down shack in the back of the town. We went downstairs into the basement, where there was an older..." Jack squinted his eyes and gestured his hands, struggling to find the words. "...half-dead looking man—pirate, sleeping in a chair with a bottle of rum in his hand. Another older pirate, who was still awake, was there as well and assisting my da' and the friend, while Val and I were left to our own.

We got bored so we explored the basement area a bit. There was a main room the stairs initially went down to, and there was a hallway with multiple doors. We opened up one door, there a ton was cargo in that room, probably full of rum. We opened another door and there was nothing in that room all. Nothing! The third door we opened,...we couldn't see anything at first, but there was a small lantern hanging from the ceiling. It was dimly lit, revealing three small children—younger than us, sitting on the floor in a line, cross legged with their backs facing us. They looked native, I think. Other than that, there was something really wrong with those kids. One boy was stick thin. You could see every bone in his body through his skin. The girl had burns all over her body. The other boy had no limbs. They all sat together and contently watched whatever was in front of them. Val and I went and sat behind them to see what they were watching.

There was a bed on the other side of the room. On the bed, was a girl, probably around fifteen. She seemed to be native like those kids, and she was very thin,...naked, and beaten. All her limbs were chained to the bed, and there were two pirates, one on each side of the bed. Ghastly looking pirates indeed! One of them was flogging her with the cat. The other one was on the bed doing...disgusting things to her. Valerie looked away and closed her eyes. I sat there frozen...and afraid, as I watched and listened to this girl scream as those pirates tortured her. When my da' called for us to go, Valerie gave the doll that she had brought with her to the girl with the burns and we left," Jack paused for a moment as he relived those memories.

Anne's eyes were wide, full of fear and shock, and her hands covered her mouth. "That is horrible! How could they do that?!" She gasped, with tears almost filling her eyes.

Jack shook his head and shrugged. "I knew the Code quite well as a lad since my da' is the keeper of it, and all pirates had to follow and abide by the Code. I wasn't exactly sure whether what those pirates were doing to that lass over there was against the Code or not, but that gave me nightmares for months! It was unnerving to me how those kids were just...watching it. Valerie and I swore to never tell anyone about what we saw because we were afraid the family wasn't going to let us go on adventures with them anymore. Anytime we ported at those islands since then, Val and I always requested to stay on the ship."

Jack looked back at Anne again and smiled. "But hey! That was only one story out of the millions of adventures I've had and they were all great! Being out at sea,...it's like a home away from home. Every time I'm out there on a ship, feeling the world rock below me in the waves, the wind on my back, the spray of the sea, the sun beating down on me,...it makes me feel...feel..."

"Free?" Anne finished for him.

"...yes...free," Jack looked into her eyes, breathing heavily.

For all those years, he had been struggling to find the words to sum up the feeling that he had. He now finally had a name to it. Free...

"I definitely get that," Anne agreed. "I grew up in Europe. My father was English and my mother was French. I'm not sure if it's like this here, but women where I was raised have a ton of restrictions. I was determined to have a proper education, and not without some struggle, I ended up being one of the first women to ever attend University in Britain."

"University?"

"Yes, it's a lot like school."

"School? Never been to one, but I've heard terrible, terrible things about," Jack jokingly said, shaking his head. Anne laughed at his response.

"Well, it's pretty boring, but it's not that bad," she shrugged. "I was so close to completing my education when my parents decided to drop everything and expand their holdings out to the New World. I did not agree to moving out there with them and my sisters at all, so when we moved to Virginia, I parted ways with my family. I told them I left for theatre studies. What I actually left for is adventure...and freedom."

"But wait. How did you get here—to Shipwreck Cove?" Jack questioned.

"Stowed away," Anne replied like it was nothing.

Jack stared off into the distance, still confused about something. "One more question, love. How old are you?"

"Twenty-three," she answered. "How old are you?"

Jack looked back at her, surprised by her age. "Oh, well same as I!"

"Hm...You look pretty young for twenty-three," Anne pointed out, puzzled.

"Oh, you know,...I'm quite known for my baby face," Jack laughed a little.

Anne reached into her crossbody bag she laid in the sand and pulled out a book. She pressed the book against her chest and closed her eyes.

"Before we left Europe, I was also in theatre. I've loved it since I was a little girl. When I was old enough to perform, I was the only girl to act on stage in my town. Shakespeare's work has always been one of my favorites and I always carry this book around to read."

Anne looked down at the book, flipping through the pages. She turned to a certain page and handed the book to Jack. Jack quickly skimmed through the page. It was a scene from Romeo and Juliet. Jack looked up at her as she gestured him to read the page. He cleared his throat and began to read Romeo's part.

"If I profane with my

unworthiest hand

This holy shrine, the

gentle sin is this,

My lips, two blushing

pilgrims, ready stand

To smooth that rough

touch with a tender kiss."

Anne took the book and laid it in between them. She began to read Juliet's part.

"Good pilgrim, you do

wrong your hand too much,

Which mannerly devotion

shows in this:

For saints have hands that

pilgrims' hands do touch,

And palm to palm is holy

palmers' kiss."

Jack and Anne continued back and forth. The more they read, the closer their faces drew to each other.

"Have not saints lips,

and holy palmers too?"

"Ay, pilgrim, lips that

they must use in pray'r."

"O then, dear saint,

let lips do what hands do,

They pray—grant thou,

lest faith turn to despair."

"Saints do not move,

though grant for prayers' sake."

"Then move not while my prayer's effect I take..."

Their lips were just barely an inch apart. Before Jack could finish his line, he went in for the kiss and he was stopped by something in his way. His eyes opened to see Anne smiling, as her finger was pressed against his lips. The skin on her finger felt so soft against his lips.

Anne turned and carefully took off her shoes and stockings. She stood up, picked up her dress, and walked down the beach to the shore, stepping just above ankle deep into the rising and receding water. Jack kicked off his boots and did the same, following her down to the water.

They looked out to the water together as the sun set behind the outer island, and they noticed the tide began to rise. Anne continued to look out at the water when she felt something splash on her leg. She looked over at Jack, who was facing her with his arms crossed and a smirk on his face. He was the one who kicked water at her.

"What do you think you're doing?" She asked, smirking back and raising an eyebrow.

"Nothing," Jack said. He kicked water at her leg again.

"If you do that one more time, you are done, Sparrow!" Anne warned.

Jack stood still for a minute, as if he wasn't going to do anything. He then bent down to the water, dipped his hands in, and threw a large splash at her, making part of her dress wet. Jack straightened back up quickly as he saw her face. Her jaw was agape. She tried to look angry and hide her laughter, but it wasn't working well. She quickly let go of all the fabric in her dress she had all gathered in her arms and grabbed Jack's arm.

"That is it, sir! YOU. ARE. GOING. DOWN!" Anne yelled out as she tried to drag Jack down onto his butt in the water.

"NO! NO!" Jack laughed, resisting her strength as he was being pulled around in circles.

Anne let go of Jack and he stumbled a couple steps back as he laughed. Anne then regained her strength. Instead of trying to drag Jack down again, she went behind his back, and started to push him out towards the sea.

"Hey! What are you doing?!"

"I don't give up that easily, Sparrow!"

Her strength was too strong for Jack to resist. Every time he tried to turn, Anne moved a little, keeping him straight on path. Jack was so focused on trying to get out of her grip, he wasn't paying attention to how far out to sea she was pushing him to. Anne picked back up her now soaking wet dress and ran back to shore before Jack could realize where he was.

Jack looked around. He looked by the shore and saw Anne, already all the way down by the beach, laughing and waving at him. He looked down to see he was crotch deep into the water.

"HEY!" Jack exclaimed. He looked back over at Anne, who wasn't laughing anymore. She was still waving, but much more frantically. She was yelling out something he couldn't understand.

Jack looked behind him and his eyes widened when he saw a giant wave, almost a whole foot taller than he was, creeping up on him. It was much too close for him to attempt to run away. The wave slammed down onto him and he disappeared beneath the waves.

Anne gasped and her hands flew to her face. "JACK!"

She looked around, scanning the water for any sign of Jack. He seemed to be nowhere. She began to panic as she called out his name a few more times. Anne then saw something that gave her hope. Further up the shore, Jack's head was barely poking out of the water as he crawled on all fours back to the beach. Anne picked up her dress again and ran back down the water to Jack.

"Jack! Are you okay?!" Anne asked, still nearly panicking as she lent Jack a hand.

"Yes, yes. I'm fine!" Jack coughed as he took her hand and she pulled him up out of the water.

"Oh my! I'm so, so sorry!" Anne frantically apologized, laughing at the same time as she looked up and down at the now dripping Jack.

"Why so sorry, lass? I don't mind an unexpected dip!" Jack laughed, still coughing up water.

They continued to laugh as Anne dusted some sand off of Jack and pulled a string of seaweed off of his belt. Their laughter slowed down into giggles and they looked into each other's eyes. They fell silent as their bodies, and their faces drew closer together. Their lips were barely touching. Jack figured this was finally the right time. He went in further, pressed his lips against hers, and pulled back as quickly as he in. Jack remembered the scene they had read earlier and he finished his line.

"Thus from my lips,

by thine, my sin is purg'd."

Anne's face lit up. She picked up where they left off.

"Then have my lips the

sin that they have took."

"Sin from my lips?

O trespass sweetly urg'd!

Give me my sin again."

Jack kissed her again. They slowly closed their eyes as they continued to kiss. Her lips were so soft, he wished he could never let go of them! Jack slowly opened his eyes a little in the middle of their kiss and he swore he could make out the brothel girls poking their heads out from behind some rocks afar, quietly cheering him on. He was too focused on Anne to wonder how those girls got here. He then closed his eyes once again.