Pirates Of The Caribbean Fan Fiction ❯ Lost in Translation (Pirates of the Caribbean) ❯ An Illicit Affair ( Chapter 14 )

[ Y - Young Adult: Not suitable for readers under 16 ]

Chapter Fourteen:
An Illicit Affair


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Jack put his compass away and looked out at the horizon. He wondered how much of her request had to do with him and how much was merely her own way of rebelling against her father and her intended marriage. After several moments he called Gibb's over and asked him to take the helm for awhile, saying he wanted to get a bit of rest. He didn't turn the helm over any more than necessary, but he had been there a good part of the day so Gibb's didn't second guess his motives.



Jack wandered around the deck, checking over a few things before heading to the cabin and knocking. He thought it might be best if he at least spoke to her, rather than having her getting upset at him for doing nothing. She looked a bit surprised to see him when she opened the door then stepped back so he could enter.


He stood silently contemplating her as she fidgeted nervously and looked around the room. He, himself, wasn’t sure how to approach this. Oh, he knew how to handle whores; they were always ready and willing, knowing exactly what to do.


“Tell me, love, what exactly are you expecting? Do you have some romantic notion about soaring into the sky, seeing stars and clouds and other such drivel and nonsense?” He asked while gesturing widely with his hands and stepping a bit further into the cabin. Normally, she would laugh at his description and gestures but not right now, she was far too nervous.


“I...expect it to hurt actually...my mother said the first time does. And I...know that...well...” she stopped talking not exactly sure what else to say and feeling more and more embarrassed by the moment. He was experienced and the more she thought about it, the more she felt like she would only manage to disappoint him.


He grinned at her, not that he found her embarrassment humorous, but because of the sudden silence.

“Don’t think I’ve heard you speechless before, love,” she looked at him feeling her self caught between the desire to come up with a retort and still not exactly sure if she could trust herself to say anything.


He began removing his hat and effects, even if she changed her mind he had half a mind to sleep in the cabin tonight. Hell of a lot better than bunking with the crew. He then kicked his boots off and removed his vest, leaving himself only in shirt and pants when he turned back to her. She hadn’t taken her eyes off of him and, honestly, looked frightened. He walked over and plopped himself onto the bed, leaning back on his elbows.


“You’ve got nothing to worry about, love. I find no pleasure in forcing meself on women,” he said, reassuring her that he wouldn’t be making her do anything she objected to. She watched him make himself comfortable on the far side of the bed then lay there with his hands behind his head. Between her conflicting emotions, her body’s natural desires and her fear of the unknown, she wasn’t sure if she should join him or leave the cabin. She believed what he said; the idea of him raping a woman was almost laughable. But she also wouldn’t feel right leading him to believe something would happen and then changing her mind.


After a moment of her silent contemplating Jack looked her way and grinned again. “Plan on goin’ out to steer the ship, love?”


“No, why?” She asked giving him a confused look. Jack directed his eyes at the ceiling again before replying.


“You keep staring at the door, thought maybe you planned to take the helm for me tonight,” he teased. She looked from him back to the door.


“You mean there’s no one at the helm?” Jack couldn’t help chuckling at the question. It wasn’t really her fault that she was naïve about the ship and the way he ran things, but no other person aboard would have even bothered asking such a thing. She looked back at him, knowing he was laughing at her just not sure why.


“Course there is, lass, Gibb’s can handle it for tonight,” he said, letting himself relax. The bed really did feel good, but he was fully prepared to hear her ask him to leave. Instead he felt the bed move a moment later as she sat beside him. He kept his eyes closed for a moment before he could feel her watching him and opened them. She was gazing down at him and smiled when he looked at her.


“I have something I’ve wanted to ask you for a long time,” she said. Jack cocked an eyebrow a little but said nothing.


“Why do you wear this?” She asked motioning to the kohl on his eyes. She hadn’t seen any other crewmen wearing it and had wanted to ask for quite some time. He smirked a little and closed his eyes again.


“Keeps the sun’s glare down, a trick me father taught me years ago,” he said sounding a bit more tired after lying there comfortably. “Can’t very well have a captain that can’t see where he’s goin’ now can we, love?”


“No, I suppose not,” she replied while watching him. Her entire life she’d been told that pirates were nothing more than blood thirsty brutes and there was little doubt in her mind that there were probably many that wouldn’t simply be lying half asleep after she’d made such a request. The idea of asking him to leave felt wrong, it was his cabin after all and he was here because she had invited him.


Rather than saying anything more to him, she reached over and dimmed the lantern before lying down herself. It took a few silent minutes for her to relax. She’d never shared her bed with a man before, even if that’s all she was doing. Jack’s sudden voice nearly startled her as it filled the air.


“Probably for the best, darling, you don’t need some ol’ scallywag complicating your life,” he said in a tired voice. She turned to face him, not sure what to say to that, so she said nothing. She realized that this statement was made, at least in part, because of his mother and the life she’d been forced into.


“Good night, Jack,” she said rather than start talking about something that would only manage to upset him.


“Night, love,” he replied and closed his eyes again. He planned to be up before dawn and simply pretend this night had never happened. However, no more than two or three hours after he’d fallen asleep he was jerked awake again. The room was dark and it took him a moment to figure out where he was and what had woken him. He then realized that Kaitlyn was sitting up trembling, her breath coming in gasps.


“What goin’ on?” His voice was still slurred from being in a deep sleep as he sat up to find out what was wrong with her. Instead of answering she stood quickly and walked around the room, trying to calm herself. Jack stretched and tried to wake him self, it had been awhile since he’d actually fallen into such a restful sleep. Finally, he stood and less than gracefully made his way across the darkened cabin.


“This dream is driving me mad,” she said in a shaky voice when he approached her.


“It’s only a dream, lass,” he said, trying to calm her down and see it for what it was. She took a deep breath and looked at him.


“No, it’s not. I can’t breathe when I wake and it’s so...real,” she said, knowing that it really was only a dream and her irrationality was only due to the vividness of it. Of course she would keep having the same dream; it overtook her thoughts so often that it shouldn’t be a surprise that it would do the same while she slept.


“I’m sorry I woke you,” she said, now feeling badly. It was silly to make such a big deal over a dream and she’d been using his cabin since she got on the ship, a night in his bed was probably something he was looking forward to. She didn’t wait for a reply, merely walked back over to the bed preparing to simply go back to sleep. However, she stopped and stood there for a moment, again feeling her curiosity rising. It wasn’t merely a physical attraction, though she did find him attractive in a rough, unkempt way.


There was something about the way she could easily talk and joke with him. No need to pretend to be something she wasn’t, even though she was nothing like him. The fact that he allowed her to remain on a pirate ship unharmed and did his best to be patient with her impressed her greatly. And above all, she trusted him, pirate or not. He’d never given her reason to doubt his word and proved just how trusting he was this very night with the way he had treated her.


So many little gestures he’d made, times he’d offered her his hand when helping her from a boat or across rocks, showed what a gentleman he really was, despite his appearance.


“I did mean what I said to you earlier, I just... got nervous,” she said not looking at him. Jack stood silently, mulling over his own thoughts and conscious. He was a man first and couldn’t help having a selfish desire to take her up on her offer. Though the idea of being with someone such as her, someone that was educated, intelligent, and most of all still a virgin, intimidated him. He could barely remember the last time he’d been alone and sober with a woman, so the idea of having her was almost enough to make him nervous as well.


“Nervous, love? What exactly is it that makes you nervous, huh?” He asked, trying to silence his own thoughts on the issue. She turned and looked at him, not speaking for a moment.


“You’ve been with other women,” she replied hesitantly. Jack was honestly surprised at her answer. He had assumed it was simply because she was inexperienced and feared the pain and even the repercussions. He stepped closer to her, still unsure himself what would happen.


“There’s been a few, love, no point in denying that. But I don’t take just any woman into my bed,” he said. It was true, he was Captain Jack Sparrow, not just any whore or strumpet would do. Some were every bit as rough as men where, others had let their years of work sour them and then there were ones he simply didn’t trust enough.


“So then I would have to consider myself privileged for the opportunity?” She asked, attempting to lighten the mood with a joke.


“It would be me feeling privileged for the opportunity, love. It’s not often someone such as your self even looks at an ol’ swashbuckler like me,” he said honestly.


“You mean someone rich?” She asked. It was true that most women from her class would rather see a pirate dead than consider sharing a bed with him. Jack smirked a little then shook his head.


“It’s not about the money or where ya came from, love. Intelligent, pretty young lasses that take care of themselves don’t waste their time with pirates for a reason. They can have nicer things...better lives for ‘em selves.”


“If I were only interested in having nice things, I wouldn’t have left my home to live with someone that used to be my maid,” she said. “I wanted to go see Isabel because I care for her, love her like a mother.”


“You’re not like most young lasses,” he said.


“Well, you’re not like most pirates,” she replied.


“Maybe...” Jack said with a slight pause as he stepped closer to her. “That’s why we’re here havin’ this conversation in the first place, aye?”


“Aye, maybe it is,” she replied with a grin.


“Not sure what I’ll do if ya start talkin’ like a pirate, love. I’ve grown a bit fond of hearing you insult me politely.” Kaitlyn laughed a little then looked at him seriously. As crazy as it might have seemed weeks earlier, she cared for him. She trusted him and she couldn’t say the same for the man she was intended to. She didn’t want to give herself to a man she didn’t trust, let alone a man she didn’t even know.


“I do want to be with you, Jack,” she said quietly then let her fingers begin touching his chest. She vaguely remembered touching him before but the rum had made her memories foggy at best. His reaction wasn’t what she had expected. She half expected him to come alive at her words and try to get her to the bed, but he stood silently watching her instead.


“You sure this is what ya want?” He asked. “It won’t be easy for ya if anyone caught wind of it, lass.”


“It is what I want,” she said. “I don’t want the only man I’ll ever know to be a man my father forced me to marry.” Jack nodded, understanding her reasoning then watched as she continued to touch him shyly. He found himself intrigued with her. He’d never had the pleasure of having a woman that had never experienced being with a man before. Every encounter he’d known had been drunken romps with women he’d rather not grow familiar with. He had to admit to himself that there was something erotic about having such an innocent young woman to him self. Whores were only interested in earning their money and going on their way. The idea of being able to take his time and enjoy teaching her was something he was beginning to eagerly anticipate.


He could tell she was nervous and not entirely sure what she should do. Her tentative and unsure demeanor was foreign and yet slightly arousing to him. Finally, he reached down and took her hand then grinned at her.


“Afraid you won’t enjoy this much if you’re scared of me, love,” he said. She let out a slight laugh, almost happy he had responded to her in some form.


“I’m not scared of you,” she replied.


“Then I’m not doing a very good job of being a pirate, now am I?” He asked, still grinning at her.


“A pirate? And here I had you mistaken for a gentleman,” she said playfully. Jack cocked an eyebrow then leaned closer so he could whisper.


“Think in all me years, yer the first to accuse me of that, lass.” Kaitlyn watched him for a moment, taking in the depth of his eyes. Everything she’d ever been taught, told her that this was wrong. He wasn’t her husband, he wasn’t even her betrothed. Her parents certainly didn’t approve of him and mostly, he was a criminal in the eyes of the law. Everything she’d done would no doubt haunt her remaining days. She’d be shunned by society and possibly face hanging herself for consorting with pirates.


“My mistake, Captain Sparrow,” she said with a playful smile and then kissed him. Jack couldn’t help but grin, hearing her call him that, but quickly found him self returning her kiss. The absence of rum didn’t make this one any less enticing than the last. His hands quickly became restless and began rubbing her back before moving to her sides, however the second he began lifting the thin material of her shirt, she stiffened.


“You want me to stop, love?” He asked, not entirely certain he would be able to stop himself if it went much further and wanted it to end now if need be.


“No,” she said. She’d be lying if she said she wasn’t nervous, though a part of her was strangely excited as well. Like all young women, she’d been curious about men and sex for quite some time but lived a life that kept her from asking too many questions, let alone exploring her sexuality. Jack watched her closely and then let his hands wander back to the hem of her shirt and begin to lift it. The second he had it off, her arms instinctively covered her bare chest but he decided it wasn’t an appropriate time to be teasing her about her modesty. Rather, he let his hands rub her arms gently while he began kissing her neck.


Kaitlyn closed her eyes and felt her body relax and then began tugging at his shirt, which he quickly pulled off and tossed to the side. He went back to kissing and nipping at her neck, letting his hands roam over her back and sides before moving to her ribs. A slight grin overtook him when her breathing quickened and he let his hand brush the underside of her breast. The anticipation and her reactions were something he actually found himself enjoying. He stepped closer to the bed then lowered her to it, grinning the whole time. Kaitlyn blushed at the silly look on his face and the fact that he was hovering over her.


“Gettin’ a bit warm, love?” He teased, causing her cheeks to turn a shade darker. Her blushing caused Jack to grin even more wickedly and then he started kissing her neck again. She closed her eyes when she felt his lips traveling down to her chest; part of her was still telling her how wrong it was, while the tingling feeling inside of her was saying the opposite. She couldn’t help but let out a giggle when Jack began teasing her nipple with his tongue. The sound was surprising to him, he’d had drunken whores before that laughed and carried on but he had never paid much attention to the way they responded to things he did.


He continued his teasing and tormenting for a few moments, paying attention to the soft giggles and whimpers that were almost involuntarily escaping her lips, before moving down. He was grateful she’d put her ‘ship clothes’ back on and he didn’t have to fight with layers of fancy clothing. Her nervousness was quite apparent as his hands slid down to her hips and began pulling the pants away. He quickly tossed them on the floor and moved back over top of her. She was watching him anxiously and the realization dawned on him that it was probably the first time she’d been fully unclothed in front of a man.


As mindful as he was trying to be of her nervousness, he couldn’t ignore his own needs much longer. He was practically in silent prayer that she wouldn’t ask him to stop because a part of him wasn’t sure that he could, while another part knew he couldn’t force himself on a woman. He quickly reached down and unfastened his breeches and began removing them, leaving them on the floor with the rest of their discarded clothes. He lowered himself to her again and began kissing the soft skin near her collarbone until he heard her voice.


“Wait…” she said quietly. Jack closed his eyes, trying to regain his composure, and then pulled himself up and looked at her.


“Change yer mind, love?” He asked, trying not to sound irritable.


“No…it’s just that…I’ve…never,” she said and looked down at him. He watched her for a moment and then realized what she meant.


“Ah...” He moved to the bed beside her and leaned back, watching her as she looked at him. He could see that she was honestly curious about his body and he wasn’t going to stop her if she wanted to become more familiar with it. An involuntary shiver passed through him when she ran her fingers over his chest and then down to his stomach. He noticed that again she was blushing as she let her hand wander lower, and then he closed his eyes and took in a deep breath. It had been a very long time since he’d had anyone touch him and he couldn’t remember a time when it had felt so sinfully satisfying.


Kaitlyn felt like her cheeks were on fire as her hand moved down his body and then began touching him. It wasn’t something a young, unmarried woman did every day and it was certainly the first time she had ever seen, let alone felt, a man aroused before. She glanced up and saw that he had his eyes closed, clearly enjoying what she was doing. The idea of bringing him pleasure felt oddly empowering and was making her own desire grow even more apparent to her. A soft moan escaped his lips and the sound made her feel less tentative and nervous about her inexperience and what she was doing.


After a couple moments he leaned forward and kissed her again, moving her back to the bed in the process. If he let her continue with that, there was a possibility that he wouldn’t last long enough to help her experience much of anything.


She was fidgeting beneath him, mostly from her nervousness he assumed. Jack continued kissing her then positioned him self between her legs and entered her, doing his best to be careful. Instantly, he could tell that it was painful for her; her muscles tightened around him and she took in a sharp, pained breath. He held himself still, not sure how long it would take the pain to pass, and then brought his mouth close to her ear.


“Alright, love?” He asked quietly. She blinked back the tears that were stinging her eyes and nodded; waiting for the pain to dull. Once it had she began moving slightly, still getting used to the feeling of him being inside of her. Jack began moving with her, making sure he kept his movements slow and careful. After a few moments he felt her body relax and decided that he could hold back less, though, he knew he shouldn’t be too forceful with her. Despite keeping his enthusiasm and pace to a minimal; the long, lonely months at sea caught up to him and he struggled to hold himself back, for her sake, but finally came. He could tell she hadn’t gotten any real pleasure out of the experience, though there was little he could have done to ease the pain and nervousness she had felt. After catching his breath, he lifted himself up and looked down at her.


“Gets a bit better, love,” he said and then moved to the bed beside her. She looked over at him when he ran his hand across her stomach and then moved it down further and began stroking her softly. He didn’t particularly want her first experience with a man to be disappointing, especially since it had been with Captain Jack Sparrow. Again he found her responses interesting. Every time he had been with a whore, they would mindlessly scream out his name, just as they did with every other paying customer. Whores weren’t only paid to give a man pleasure, but to boost his ego and let him live in complete fantasy.


At first Kaitlyn simply closed her eyes and relaxed, allowing him to touch her. Shortly after though, her breaths were coming in shorter gasps and her body was moving somewhat restlessly beside him. Despite the lack of screaming or calling his name, he couldn’t help but grin smugly while he watched her. Soon her entire body became ridged and she was holding her breath for what seemed like an unnaturally long time, until finally she let out what almost seemed like a painful cry and began trembling slightly as her body began to calm itself again. Jack’s eyes never left her face, finding him self truly interested in watching her while she experienced being pleasured for the first time. After she got her breathing under control she opened her eyes and looked at him. She looked as though she was bordering between being a passionate woman and an innocent girl; leaving him almost feeling guilty for what they’d done.


Rather than dwell on it, Jack made him self comfortable on the bed, feeling tired and content. He hoped Gibbs didn’t mind being in charge for awhile because he had no intentions of heading back out to the helm until he’d finished his night’s sleep, not that he had minded the interruption of course. He nearly jumped when he felt Kaitlyn rest her head on his chest. He had grown accustomed to whores that simply took their money and went looking for their next customer and hadn’t been prepared for the affectionate gesture. He glanced down at her, not really minding her being there, and having no intention of pushing her away. It wasn’t every day someone like him got to experience something even remotely meaningful.


He let his hand rest on her back, occasionally rubbing it sleepily, wondering if she would regret what had happened when she woke in the morning.