A/N: I know, I know...it's about time I updated, right? Well, things have been busy...good, but busy. As a result, this chapter has been a long time in the making. It's a bit longer than the last ones and it answers some of those questions you've all been asking :o) (This was another reason it took so long to write and edit...I desperately hope that I meet your great expectations). Enjoy and I promise to have the next one up very soon.

fearlessfreak...Sorry to keep you waiting so long! Glad you're enjoying.

Indy Croft...It's good to see you back :o) I thought that adding some characters from Jack's past would add a little twist to the story.

C'lyn...A nice mix, eh? Sex and violence...that's all a story really needs, right? I guess this is why I love pirates so much :o)

Cal...Made it through another hurricane! How is your family doing? I hope they are safe and well. I'm glad you're enjoying Ana's ability to be a bad-ass pirate when she must. I really hope she makes an appearance in the second films because she's by far one of my favorite characters. ..that coupled with the sexual tension I can feel when she and Jack are on screen together :o) Of course since it's a Disney film we won't get to see any of that :o( Damn rat....

Kungfuchick...kept you waiting a while this time, didn't I? :o) Sorry about that mate...Enjoy!

Rose Noire le Mort...Hope I didn't keep you waiting too long. I do rather admire the way Anamaria handles herself...such a strong, bold lass...and she gets to sleep with Jack. I'm incredibly jealous ;o)

Drink up me 'earties, Yo Ho!

Chapter Nineteen

An hour later, both ships had weighed anchor and were on their way to Tortuga. They couldn't have asked for better weather. The sky was clear, the sun burned bright and for the next few days there were perfect sailing winds against an ocean that stood almost completely still. It was perfect for getting the two half manned ships to the port city.

The two captains were unable to see or talk to one another for the three days it took them to reach their destination and Jack found that he missed not only Anamaria's company, but also her counsel. Gibbs was a skilled sailor and served as a good first mate, but Anamaria was wise beyond her years. Together they would always have made an unstoppable team.

When the boats were docked, Jack met Anamaria on the pier.

"Are you going to stay with her tonight?" she asked him, nodding towards The Pearl.

"I might," he smiled back as they began walking towards the town. "'ow is she?"

"I'm already in love," Anamaria said.

Jack nodded, "I thought you might like 'er."

"I thought she was going to be too big, but she's perfect. And the crew, the ones who are staying at least, are great. Hard workers," she added.

"'ow does she feel?" he asked.

"So smooth," Anamaria said. "She's amazing. You have to sail her at some point."

"She'll never be The Pearl," Jack said.

"I know, but she's damned close."

They stepped inside The Briar Rose and checked to make sure that Mr. Gibbs and Nuri had followed them. The two first mates had wanted to give the captains room to speak privately in the town, but knew their presence would be required at the meeting once inside the tavern. Anamaria chose a table while Jack went to get the first round of drinks.

He returned soon with four mugs of rum. Mr. Gibbs lifted his to prepare a toast.

"To our newly named Captain, Anamaria Saldana and to Commodore Jack Sparrow," he said.

Jack smiled widely: he was enjoying the title already. The pirates raised their mugs and then brought them to their lips. Mr. Gibbs and Nuri only took brief drinks, but Jack and Anamaria drained every last drop of theirs in one long gulp. Jack finished first, only by a second, but slammed his mug down on the table to celebrate his victory none-the-less.

"The next round's on me," Anamaria stated, rising to get more alcohol.

When she returned, the pirates were ready to begin a more serious discussion about future plans.

"I've got to find a crew here," Anamaria started, "and that could take some time. You need to go to Port Royal."

Jack nodded.

"What if we sailed to Port Royal while Miss Anamaria found herself a crew," Gibbs suggested.

Anamaria could tell that Jack was turning the idea over in his head.

"It would save us both time," Nuri added. "You could go ahead and get the trip to Port Royal out of the way and by the time you got back we would have a crew put together, waiting on you and ready to go."

Jack studied Anamaria carefully, "How do I know for sure that you'd wait on The Pearl?"

"Oh Jack, please," Anamaria said. "If you don't trust me by now, we shouldn't even attempt to sail together."

Jack nodded. In truth, he did trust her. She knew that, but she also knew that he would never let on to anyone that he believed in her so strongly.

"It's a fine plan," Jack said. "It makes sense. The trip should take us about a week and that gives you more than enough time to find a full crew. There's only one problem."

"What's that?" Nuri asked, still feeling a bit new to the pirate's important meetings.

"I'm not going to enjoy the week in Tortuga," Jack said, a sly grin spreading across his face.

The other pirates shared a laugh.

"So I suppose you won't be leaving this afternoon," Anamaria joked.

"Are you kidding? Definitely not," Jack confirmed. "You have to allow me to enjoy at least one night's worth of fun in my favorite city."

Anamaria nodded, smiling, and then took a long drink of her rum.

"So that's the plan?" Mr. Gibbs asked. "We sail for Port Royal tomorrow?"

"Aye," Jack agreed.

Mr. Gibbs finished his rum in one final long swallow and stood to leave. "I'll meet you tomorrow afternoon," he said to Jack. "Best of luck to you Miss Anamaria."

"Thank you Mr. Gibbs," the new captain responded.

"That's all?" Nuri asked. He had not expected the meeting to end so soon.

Jack nodded, "Actually, if you don't mind Anamaria, I'd like to speak to Nuri in private for a moment."

Anamaria eyed her former captain for a moment before agreeing, "I'll go get the next round."

"Thank you Captain," Nuri said quickly, "but this one is all I need."

"Are you sure?"

"Yes, yes ma'am, I'm just fine. Thank you."

Mr. Gibbs accompanied her to the bar before making his way out onto the rowdy streets. As soon as they were out of earshot, Jack leaned closer to Nuri.

"Don't you dare breathe a word to Captain Saldana what I am about to say to you," he began.

Nuri nodded slightly. Jack had peaked his interest.

"Nuri, you were always an excellent sailor while on my crew and I'm sure you will do the same for Anamaria. She's a strong lady and she'd rather die than have anyone's help, but you keep an eye out for 'er none-the-less. The crew you pick this week is going to be essential. Anamaria was key to attaining almost all the crew for The Pearl last time around and I'm sure she'll do a great job once again. Just keep a sharp eye. If anything 'appens to 'er, I'm going to 'old you personally responsible."

"She's a strong woman Cap'n," Nuri agreed. "I'll keep me eyes open, but she's probably much more capable than me of stayin' out of trouble."

"Aye," Jack nodded, pausing briefly to take a drink of his rum. "I'm going to miss you Nuri. You've been a good sailor."

"Thank you Captain. I'm going to miss sailing on The Pearl as well, but Miss Anamaria needs me," he stated.

"I know," Jack said, "and you'll do fine by 'er."

"I'll try me best Cap'n."

Jack nodded just as Anamaria returned with two mugs full of rum.

"Are you giving my first mate a hard time?" she asked.

"Me?" Jack returned, his eyes immediately reflecting innocence. "I would never."

"Captain, do you mind if I go spend the night in the town?" Nuri asked.

"Of course not," Anamaria replied, waving her hand to shoo him away. "Go, have fun. Meet me in my cabin in the morning. After we see The Pearl off, we'll discuss plans for recruiting crewmembers."

Nuri smiled as he stood, "Thank you. You two have yourselves a nice evening."

"Oh, we will," Jack failed to hold back, immediately receiving a sharp smack to his arm by Anamaria.

The remark appeared to make Nuri uncomfortable and he smiled awkwardly as he left the table.

"Jack!" Anamaria scolded, hitting the pirate again.

"What?" he said, remarkably managing to maintain his innocent features.

"Nuri doesn't need to know those kind of things."

"Are you sleeping with him?" Jack asked, a tinge of jealousy in his voice.

"What?!" Anamaria was shocked that even Jack would ask a question such as that. "No! Why in the world would you even think something like that Jack Sparrow?"

"Just wondering," Jack said. He took a long sip of his rum before meeting her eyes again. She was quietly fuming. He could tell, but he managed to side step around her anger and change the topic, "So, you like being on your own again?"

Anamaria's eyes softened and she ran her finger around the rim of her mug, carefully thinking of the right way to answer Jack's question. She finally settled for, "Yes, I do."

"I'm glad you're happy then," Jack said. "We miss you on The Pearl."

"I miss being on The Pearl," Anamaria said, "but this is good for me. It was time for me to be on my own again."

"I miss you," Jack said suddenly, surprising himself as well as Anamaria.

Her remark was witty and quick, "You just miss having someone to fill your bed every night."

Jack smiled. "Never luv, never!" he chuckled.

Anamaria shook her head in wonder at the captain's cockiness, but cracked a small smile.

"Speaking of empty beds though," he pulled his most pitiful poor me expression, "I 'ave been kind of lonely lately."

"Oh yeah? And what's that supposed to mean?" Anamaria asked ignorantly.

"Are we going to stay on The Sea Wench tonight?" he asked.

"Who says we're staying anywhere?" she replied, carefully stressing the "we".

"Are you finished with that?" Jack asked, ignoring her last remark. He picked up her mug and drained the remaining contents.

"Jack! I was going to drink that!" she exclaimed.

"I'll buy some bottles on the way back to The Sea Wench. You should keep a good supply on hand anyway." He stood to leave. "Come on, let's go."

"Well, well, if it ain't Captain Jack Sparrow," a female voice called.

Jack turned to see Giselle standing behind him, her right hand holding several mugs of liquor and her left propped on her hip. He stumbled over a few attempts at words first and Giselle took advantage of the situation.

"And if 'e ain't with the same girl. I'll be damned Captain, it's been over a year now, 'asn't it?"

Anamaria was enjoying watching Jack squirm, but she decided to briefly interrupt. "We may be here together, but I'm not with Captain Sparrow." She paused before deciding to add, "My tastes run to much higher bred men."

Jack snapped his head around to meet her eyes and it only made him angrier to see a joking twinkle there. Her facial features, however, made no betrayal that her remark had been made in jest.

Giselle poorly managed to stifle her laughter, "Still can't manage to get your hooks into this one, eh? Well, you're a smart woman Miss, knowing not to get involved with a man like him. 'e'd be out to steal every woman's 'eart if 'e could."

Jack was quite ready to leave at this point. "I must be returning to me ship now," he said. "If you two ladies will be so kind to excuse me."

He walked away from the table and was halfway to the docks when Anamaria caught up with him.

"Hey! There's no need to get all upset," she joked with him.

Jack kept up his pace, answering as he walked, "I don't like being made a joke of."

"I wasn't trying to make a joke of you," she apologized. "I just like to see you squirm every now and then."

Jack didn't reply.

"Look, I'm sorry, ok?" she offered. "I didn't know you were going to get all moody on me."

"I'm not moody," he defended. "I just don't appreciate you helping 'er out."

Anamaria almost thought that Jack may have forgotten about the rum, but they stopped in the last small tavern on their way back to the ships. He bought eight bottles of rum for Anamaria to keep on board her ship. He had intended to buy more, but the dark-skinned lady assured him that six would be enough. Still, he had picked up two extra bottles just in case.

Anamaria did allow him to join her once they arrived back at The Sea Wench. As they entered her cabin, she noticed that he was intent on taking in the surroundings. He was still impressed by the ornateness of the room, not to mention slightly jealous.

Anamaria gave him a moment to take it all in as she stored the bottles of rum in a cabinet close to the portion of her room that served as a study. She then met Jack in the center of the room. He was studying a piece of artwork that she supposed was possibly her favorite in the room.

"It's nice, isn't it?" she asked.

"Why is it that I decided to give you the new ship?" Jack asked, turning to face her.

"Because you love The Pearl and wouldn't give her up for anything, no matter how jealous you are right now," she answered simply.

"Ahh, I suppose I do," Jack said, pulling her into a loose hug.

"So I guess you're not still seeing her? The girl from The Briar Rose?" Anamaria quizzed. "What was her name again? Giselle?"

"No, I told you that's been over. She said I broke 'er 'eart," Jack wrapped his arms around her waist, pulling her closer to him.

"Yes, I've heard you're quite the romantic," she joked with him, nipping at his neck.

As it turned out, they didn't drink any of the rum Jack had made a point of purchasing that evening. Instead they made their way straight to the bed, taking their time this time and christening the room properly.

As they laid side by side several hours later, both of their bodies still glistening in the moonlight from their combined sweat, Jack thought of how much he was going to miss these times shared between them. He wouldn't lie; he was going to miss having her in his bed every night. She was the one woman he had met in his life that shared his extremely high sex drive and they had been enjoying each other's bodies every night for months now. But there was more to it than just sex, Jack was going to miss her companionship and more importantly, her counsel. How many times had he gone to her in the past and asked for her advice on a matter? How many times had she saved him from making a stupid mistake in regards to the crew? Or a navigational error? She had been his right hand man, his most important, trusted, and closest confidant. He had no idea how he was going to make it without her. And yet he didn't have a choice. She had her own ship now, her own priorities, her own life...different and separate from his.

"Ana?' he asked softly.

"Mmhmm," she mumbled, already well on her way to the land of the sleeping.

"Are you still awake?" he asked.

"Mmhm," came another, and shorter, mumbled reply.

"She was going to be my wife," he said.

Anamaria was confused and she wondered if she had dozed off at some point in their conversation. "What?" she asked.

"Maddy, or Madelyn. We were engaged to be married," Jack said quietly.

Anamaria had to strain her ears to pick up his words. But she had heard the name and now finally, after all this time, she was going to get an explanation. She rolled onto her side so that she could hear him better, but he pulled her closer to him and she ended up resting her head on his chest.

"What happened?" she asked.

"She found someone else," Jack said.

Anamaria wondered if he was going to end the story there, if he felt that he had shared enough of his past with her at that moment. She decided to press her luck.

"Tell me," she whispered.

Jack let out a heavy sigh and for a minute she thought she was going to be reprimanded as she had been the last time. The remark had stung and she almost cringed in anticipation, but then he continued in his soft whisper. It was a tone she loved for it's ability to inspire so many different responses from her.

"We were young, so young," he started. "Back when we thought that love was all you needed, that love was all that mattered. Before you find out that it can crush you, that it can bring you to your knees and break you in half in a moment's time."

Anamaria thought she might have heard the pirate's voice crack, but she couldn't be sure and she tossed the thought aside, crediting it to her own imagination.

"I was sixteen when I met Madelyn and she was fifteen. We met at the docks, down by the ships. She was there to inspect one of 'er father's newly purchased ships and I was there looking for a job on a merchant crew. I would say it was love at first sight, but it wasn't. It was a basic attraction. What she saw in me I'll never know, but for me, she was the most beautiful girl I 'ad ever seen in my life."

Jack paused to scratch his chin before continuing, "I didn't grow up around girls like that you know. I was raised on the streets. My mother was a gypsy and I never laid eyes on nor 'eard anything about my father. That's why I was down at the docks that day. I was tired of moving around from town to town with my mother and our surrogate family. I wanted some stability to my life and I know 'ow strange that must sound to you. I moved from one traveling life to another, but I guess looking back on it, I've never really known another way.

"The second I noticed Madelyn staring at me I felt my whole world turn upside down. Here was this girl in this beautiful dress, hair styled, holding an umbrella to shade 'er ivory skin from the sun and she was showing interest in me. It wasn't a curious sort of interest either, or that sort where you stare at someone like they're out of place. Even at sixteen, I was well experienced in the sexual realm and I had seen that look of desire before."

Anamaria smiled to herself at the thought of a sixteen year old Jack. He was bragging on himself now, but she would have been willing to bet that he had been more than a little awkward at the time.

"The problem was that I wasn't sure of whether to approach 'er or not. As I said before, she was inspecting 'er father's new ship so I couldn't very well go onto the ship to speak to 'er. I continued about my business and it was much later on in the day when I was about to steal my lunch from a vendor's cart that she came up behind me, giving me such a scare that I dropped the apple I was trying to slip into my pant's pocket and almost got caught red-handed. She giggled a high girly laugh when she saw what she'd nearly done and when I looked into her eyes I saw such an innocent twinkle there that I thought I could spend the rest of my life gazing into those bright blue orbs."

It was odd to hear Jack talk so openly and to hear his thoughts as he reminisced. Anamaria was enjoying hearing him recount the tale.

"She asked my name and what I was doing there at the docks that day. Apparently she was accustomed to spending time there because she commented that she had never seen me there before. Somehow we ended up on a secluded little part of the beach just sitting on the rocks and talking. We lost track of time and it wasn't until the sun began to sink that we realized 'ow late it was. She got upset because she thought 'er father would be angry with 'er and she dashed off before I could find out when I would see 'er again.

"I went back to the docks the next day, still searching for a crew I could join, but also in hopes that she would stop by. She was there, with her father again, and I tried to keep myself busy, all the while hoping that she would find me. It was after lunch when she finally caught up with me, but we spent another wonderful day on the beach together. We shared our first kiss that day," he added, "under the sinking sun and it was pure magic. I 'ad never known that feeling…but I knew when she kissed me that it was love. There was no other explanation.

"We spent nearly every afternoon together that summer and I only grew to love 'er more. Her father was a nobleman in the town and I should 'ave known better than to get involved, but she 'ad me wrapped around 'er finger from the beginning. I adored 'er. I met 'er family after several months and her father immediately disapproved. I wasn't the type of person that 'e even wanted to see hanging around his daughter, much less having a romance with. He forbid 'er to see me, but she defied him and we kept seeing each other anyway. It wasn't long before we found out that we couldn't live without one another. I proposed to 'er early that winter and she accepted, much to 'er father's disapproval. We couldn't 'ave been happier though. We were young and in love and that's everything you need, isn't it?" Jack let out a tiny scoff, mocking himself.

"The only real problem we saw at that point was money. I 'ad nothing and 'er father had cut 'er out of his wealth. He didn't banish 'er from his life completely, but from the beginning he made it clear that I wasn't welcome to anything that belonged to him. Maddy and I agreed that it would be best if I went off to sea for a few years and earned a good living. When I came back, we would be married.

"I 'ad found a good crew to sail with, but I 'ad only been making short trips with them, earning just enough money to get by so that I could see Maddy as much as possible. It was 'ard, but I agreed to write as often as possible and she agreed to wait for me. She told me that it didn't matter 'ow long I was gone, she would wait forever if the need be.

"We 'ad planned to wait until we were married to be together, but several weeks before I was to sail out she said that she couldn't wait. We ended up making love a few times before I left town. I was so in love with 'er. She meant everything to me…the whole world."

Jack paused in the telling of his story. The memories were so vivid to him at that moment that it was starting to scare him. He could almost picture Maddy at his side right then, could feel the weight of her head on his chest, her warm breath at his throat. But no, it was Anamaria, not Madelyn, and it relieved him somewhat to realize he was not disappointed in his discovery. He cared for Anamaria just as deeply as he had Maddy. She stirred at his side and he remembered to pick up the story again.

"I was gone for nearly three years. I wrote to Maddy almost every day and thought about 'er constantly. I visited 'er several times during those long years and each time we both feel deeper in love than we 'ad ever been. As she grew into a woman, she became increasingly beautiful. The last time we were together I realized how stunning she had truly become and I remember thinking that it wasn't possible that she could really love me, that she would really want to be with me. She 'ad these huge blue eyes and long dark brown hair. It was a unique combination and I think she was probably the most beautiful woman I 'ad ever known up until then. I admired 'er…doted on 'er…and she knew it.

"What happened?" Anamaria asked, interrupting for the first time.

"We 'ad a few days off at one point, after almost a solid year of never going home. She didn't know we were coming and I was going to surprise 'er. I went by 'er father's house to see 'er and I was told that she had married. I was in shock. I couldn't believe what I 'ad been told and I thought that perhaps they were all playing some sort of cruel joke on me and that her father was at the crux of it all. I gathered myself together and asked where she and 'er husband were living. Amazingly, the butler told me and I headed across town to find 'er.

"The house 'e 'ad given me directions to was a mansion. I knew I must 'ave been in the wrong place. My heart still told me that this couldn't possibly be happening and then I saw 'er. She was standing in the garden, picking flowers and placing them in a little vase. She was radiant, more beautiful than I 'ad ever remembered 'er and in that instant I forgot everything I 'ad been told. She was mine and I went running to meet 'er. I was only a few feet away from reaching out to hug 'er when I saw the sparkling ring on her finger and even closer before I realized that she was several months pregnant, 'er large belly bulging out from the long white dress she was wearing.

"She looked surprised to see me and I felt a complete fool all of a sudden, standing there in 'er garden, thinking that she might possibly still 'ave been mine. It 'ad been over a year since the last time we had made love.

"She started to try to explain everything to me. The distance had been hard. She 'ad had to wait so long and she didn't really know if I was ever going to come back. Her father had pressured 'er and at one point even told 'er I 'ad been proclaimed dead at sea. None of it mattered. I walked out on 'er as she screamed her love to me out loud on the street. It was the worst I've felt in my entire life. To be betrayed like that, by someone who is supposed to love you…nothing burns hotter.

Jack drew in a deep breath, trying to focus on not getting upset again, and then he continued.

"I 'ad saved up a lot over those three years and I took my money straight down to the harbor and I made my first investment on a little three master you now know as The Black Pearl. I poured everything I had into her and she became my love, my fixation…a positive bright light to come out of all that darkness. The first day that The Pearl was to set out with me as 'er captain I awoke from my cabin to find Maddy standing in front of my bed. She was dressed in rags and she was crying. 'er eyes were bloodshot and puffy as if she'd been crying for days. She looked entirely disheveled and my 'eart immediately went out to 'er before I could stop myself.

"I listened to 'er entire story, that she still loved me, that she didn't want to be with anyone but me, that she would leave him right now and sail all the way around the world with me and only me. She begged and pleaded but as she stood there all I could focus on was his ring that had replaced mine. She was pregnant with his child, wasn't she? Therefore, she must 'ave 'ad some feelings towards 'im. She insisted there were none and I think I believed 'er. The simple fact was still 'er betrayal however. She 'ad forsaken our love, 'er promise to me, to be with another man and no matter 'ow badly I wanted to, I could not forgive 'er.

"I personally rowed 'er back to shore and after I 'ad dropped 'er off on the shore with a relatively difficult struggle, she dove into the water and attempted to swim out to the boat. It was a very hard day, but I left her there in the town, with her husband and future child. I left 'er with the life she 'ad chosen over me."

Jack stopped there. He was pondering whether or not to continue when Anamaria asked him, "Did you ever see her again?"

"It was almost a full year before we came to port there again. I was reluctant to go into town, but I got drunk one night and felt inspired to search 'er out. That's when I found out that she 'ad hung herself…not long after I left apparently. She 'ad penned a letter to 'er husband telling 'im that she 'ad never loved 'im and that if she couldn't be with me, she would rather die. Then she hung herself from the rafters inside their barn."

Anamaria didn't know what to say. The ending to the story had really surprised her.

"I'm sorry," she offered.

"For what?" Jack said. He shifted his body and when she lifted her head he rolled onto his side, putting his back to her.

"It was 'er choice. She chose to be with him."

"I guess she couldn't live with the choice she had made," she whispered softly.

Jack shrugged, sighing heavily.

"I'm still sorry," Anamaria said, pulling his body to hers. She kissed him softly on the cheek.

"I suppose it's as much my fault as it was 'ers. I just couldn't forgive 'er for what she'd done."

"It's not your fault," she said. "I know you'll probably always feel in some way that it was, but it's not. Like you said, it was her choice."

Jack remained silent.

"How long will you be gone to Port Royal?" she asked.

"Not long," he answered, glad for the change of subject. "A few days maybe."

"Then we'll put back out to sea?"
"Yeah," he said quietly.

She moved to kiss him on the lips, "Then I guess I should make the most of my time now, shouldn't I?"

Jack returned the kiss, pulling her roughly into his arms.