jackxwill - pirates of the caribbean slash

Title: To Win You Over
Author: Mahie (persefone_rj@hotmail.com)
Pairing: Jack/Will for sure
Rating: NC-17
Summary: Jack woos Will.
Archive: Anywhere, just ask me. After the ficathon ends, I'm willing to post it on the lists I'm in and at Aff.Net.
Warnings: Slash, and a bit of angst. Also, this is a bit sappy. So, be warned.
Beta-reader: Melannen.
Feedback: Please, I really love it!! But don't flame me hard... Disclaimers: all of them belong to Walt Disney, not to me. The plot belongs to me. And Jack Sparrow belongs to wonderful Johnny Depp. :) No infringement is intended and I'm doing this for fun, not for money.
Notes: Written for the second Jack/Will ficathon for Brie, whose request was: "I'd like a Jack and Will romance, including their first time, with Jack wooing Will. No character death please."

'thoughts' "speech" /emphasis/

The cabin was dark, and the ship swayed graciously on a calm sea. It was late at night; but neither of them could say how late.

They were very enthralled with one another.

The darkened cabin was utterly silent, except for the mild sounds of kissing. Not passionate-sucking kisses, but loving kisses. Will didn't like to go fast...and they didn't /need/ to go fast.

They were in love and now they knew it.

Hands touched Will's back caringly, caressing every bit of flesh, and came back to his hair, curling it on the fingers. Will moaned happily and broke the kiss softly, bringing his forehead to rest on Jack's shoulder.

"Can't believe I didn't know..." Jack murmured, holding Will tightly. "Can't believe we've waited this long..."

"We are together now," Will kissed Jack's shoulder, shifting closer to him. "And I want more than kisses."

Jack closed his eyes, relieved to know his 'Will Turner tension' would be released /very/ soon, and they relaxed? on the bed.

Little did Jack know Will had a...restriction.

He wouldn't let Jack bugger him.

When Will joined the Pearl, Jack had been very happy. The boy he had secretly loved all those impossibly long days of sailing on the Interceptor, looking for a crew in Tortuga, and chasing Barbossa after that, was there on his ship, with him. He hadn't married. As the boy didn't want to talk about it, Jack didn't push him, and never knew exactly /why/ Will hadn't married Elizabeth Swann, but...it didn't matter! Will had looked for him and asked for a place on his crew, to which Jack couldn't say 'no' not even if his life depended on it.

And so they became closer, and closer friends very soon. Only six months after Will joined the Pearl, he already fought like a pirate during raids, wasn't /very/ upset about killing people when it was needed and actually cared about Jack's saftey during those battles as well. Will was always watching his back. He knew that if Jack died he wouldn't want to go on with his life as a pirate and wouldn't have anywhere to go. Not to mention he cared about Jack the same way Jack cared about him. They just...didn't know that before this day.

Although Will was truly becoming a pirate, he was still reserved about many things. He didn't like to drink rum, nor to go to brothels while at shore, and couldn't even think about sodomy...he knew it happened on the crew's quarters, but it disgusted him. His upbringing had never allowed much /thought/ about that, let alone /practice/.

Anyway, he didn't feel guilty for wanting Jack. He just wouldn't let Jack bugger him. They would do anything, except that, period.

Sadly for Will, it was Jack's favorite entertainment in the bedroom - cabin. And he wouldn't let Will win him over by lack of attitude.


Firstly, Jack tried the easiest approach to him: 'get the boy aroused and he's going to open his legs.' So, every time they were together doing wicked things, Jack did his best to get Will /very/ aroused. He sucked his neck and nipples, took off Will's clothes carefully kissing every bit of flesh that was being exposed, touched his cock expertly. Anything just to make the boy let Jack bugger him.

Will wasn't a fool. He noticed Jack's intentions. He let Jack do what he wanted to arouse him, but when he realized Jack's fingers were very near the /forbidden/ place, Will said: "Um, Jack?"

"Mmm...?" Jack moaned, kissing Will's shoulder, caressing his bum...with fingers that were nearer and nearer...that place.

"What are you doing?"

"Why, luv, I'm kissing ye, aren't I?"

"With your fingers." Will said, glaring playfully at Jack.

"Um...touching ye?" Jack replied with his most innocent face.

Will looked at him in a way that Jack knew Will /knew/ what his intentions were. Jack sighed: "Alright, luv. Sorry. Just...couldn't resist."

Will smiled and held Jack tightly while touching his lover's cock again. Jack sighed. He loved Will, but he wanted more than hand-jobs...Will had given him blow-jobs as well, but they were rarer. Trying to forget those thoughts, Jack concentrated on Will's hands and on what they felt for one another. Maybe, in time, he would break through Will's resistance.


Jack wasn't one to give up on what he wanted so fast. He would break through Will's resolve and the sooner the better.

Next thing Jack decided to do was to talk to Will. Okay, he had failed in his first tentative, so he would try to be honest; Jack would tell Will he wanted him more than anything and that buggering was not dirty or unmanly, or anything Will thought of it. Hell, Jack would /beg/ him if he needed to. He loved Will; he didn't care if he needed to beg.

Jack spotted the object of his thoughts on the deck and felt love swell in his heart. He loved him. He loved Will. And, God, he /wanted/ him. But as he wasn't /very/ impatient that day, he approached Will calmly: "Hey, luv," Jack embraced him from behind. Will smiled, and turned around so that he could embrace Jack too.

"I want to talk to ye," Jack said, just a bit nervously.

"What's wrong?" Will kissed Jack's neck, still embracing him. "Any problems on the ship? Do ye need me to fix that sail that ripped yesterday?" Will asked, sure that it was the problem.

"No, luv, it's not the sail. I asked Mr. Gibbs to fix it. It's nothing with the ship."

Will led them to the cabin they shared, Jack's cabin. "Let's go to your cabin, drink some wine - he glared when Jack suggested rum instead - and then we can talk."

Jack let himself be dragged by Will and didn't say a thing while Will poured the /wine/ for them both. Jack sighed. Will always won him over, in all situations. Jack must've been very much in love. He didn't remember the last time he had let someone have this control over him - it was just...frightening.

But Will seemed oblivious of the power he had over Jack. He didn't use it for his benefit, not in a wicked way. And that was what made Jack fall more and more in love with him.

Will was pure. He wasn't a pirate to the core. Not yet, at least.

Jack found himself /again/ being drowned by those beautiful eyes and smile. And face. And lips. But why was Will snapping his fingers in front of him?

"Jack!!" He cried.

"Wh-what is it, luv?"

"Well, you seemed to be in another world. Here's your wine."

Will sat beside Jack on the bed, drinking as well. They drank in a comfortable silence, and when they finished drinking, Will pulled Jack to lie down, and lay beside him. They kissed and caressed, and Will was so happy and caring with him that Jack simply /forgot/ they had to talk about the buggering thing.

Will put his head on Jack's chest and Jack tightened his hold on Will. The easy silence continued, but then, sleepily, the boy asked: "What did you want to talk about, Jack?"

But Jack was already asleep, his hands on Will's hair.


Jack awoke very irritated the next day. He'd had many opportune moments to talk to Will the night before and he just...couldn't, because that boy made him drown, made him forget himself and do everything for him. Ah, that wasn't going to work this way. 'Get a grip, you're Captain Jack Sparrow!' Jack told himself.

Will didn't understand Jack's irritation that day. He was barking orders to the crew, getting irritated with the smallest mistake one made, and Will decided he would keep his distance or Jack would take it out on him as well. So, Will disappeared from Jack's sight all day.

By the end of the day, Jack was missing Will so much that he realized he was completely in love with the boy. He sighed. 'Alright, then, it seems I can't help it. So, let's try another approach.' Jack grinned wickedly to himself.

After he finished his work, he told Annamaria, who was at the helm, to stop at the nearest port. None of the crewmembers understood it very well; what was Jack up to? But they didn't push the matter because their Captain gave them leave for the night, so all the crew could think was about whores, and rum, and taverns.

Jack went another way, while Will slept peacefully in his bed.


'Alright, here's the next step,' Jack thought while walking to the city. 'I'm going to give Will presents. Woo him a bit, make the boy happy and he'll let loose. After all, ye love him, don't ye?' Jack smiled to himself. He /knew/ how much he loved Will; he knew he wanted to make Will happy. He didn't want him just to open his legs; he wanted to share good moments with his lover.

Jack came back to the Pearl later, a long box hidden behind him. Will awoke as soon as Jack entered the cabin. "Hey," Will smiled beautifully. "Where did you go?"

Jack grinned playfully, and showed Will the box he had been hiding. "What's this?" Will asked, frowning.

"It's for ye, luv." Jack offered the box to him. "Take it."

Will's smile lit up all the room, and Jack felt his heart melting. 'Oh, God, this has no price.' The Captain thought, happiness written all over his face.

"Thank you," Will hugged him tightly. "But Jack...why are you giving me a present?"

"Why, luv, do I need an occasion to dote upon ye?"

Will smiled and opened the box. It was a new sword. Truth be told, it was even better than the ones Will made. Not that the swords he made weren't good, but this one was better. Jack had looked for it in all blacksmiths shops in town, and had only gone back to the Pearl when he found the best one.

"I can't believe it!" Will said, stunned. "This sword is perfect."

"Isn't it, luv?" Jack hugged him and lay down with him on the bed.

"I love you," Will kissed his mouth lovingly.

The night went on for a while...but no buggering yet.

Truth be told, Jack was so happy that Will had been ecstatic about the new sword that he almost didn't care they didn't have sex.


Jack was sure he had chosen the right approach this time. He had bought a lot of presents at that first port, and then bought many more in other ones. Every day he gave Will something, and Will was like a puddle in his arms. The boy felt more and more in love each day.

After some weeks, Will started to realize that something was a bit weird... why was Jack wooing him so? Will started to wonder why. Not that he didn't like it; he loved it. He trusted Jack, knew that Jack wouldn't try to charge him with anything - would he?

The next day, Will received new clothes. Lots of them. Beautiful shirts with pants and even a bandanna, so that he and Jack would look the same. The quality of the clothes, and the quantity of them made Will wonder again why Jack was giving him all of this. He tried to ask Jack, but the Captain wouldn't let him speak. He said he'd leave so that Will could try on his new clothes. And left the cabin.

Shrugging, Will did just that.

The crewmembers looked at Will oddly that day. He was truly beautiful. Dressed in his new clothes, he spotted Jack at the helm and went to join him. Jack hadn't acknowledged his presence. So, Will heard him talking to Gibbs: "And I'm trying to woo him a bit..."

Curious, Will didn't let Jack see he was watching. It seemed now Will would know exactly /why/ Jack was wooing him so.

Jack spoke: "He doesn't want to let me bugger him."

Gibbs grinned wickedly at Jack: "Eh, mate, so he needs a bit of wooing so that he opens his legs..."

"Don't talk like that!" Jack said irritatedly. "You make it sound like I don't love him and I'm just doing that to fuck him. If he doesn't want me to bugger him, so be it. It's his decision. I'm just trying to woo him. Because I love him and I want us to share that moment."

Although Jack had confessed his love, Will didn't like what he heard. So, all those presents weren't gratuitous. Jack wanted something, and he wanted to fuck him.

Will felt so bad that he wanted to throw himself off the ship and never have to look at Jack's face again.

Unable to hide any longer, he let Jack see he'd been hearing everything. "Will..." Jack left the helm and went after him, but Will had run to Jack's cabin and wouldn't let him enter.

"Will, open it, luv. It's not what yer thinking."

"What?" Will shouted. "That you tried to buy me with your presents? Well, you don't need to bother anymore. I'm leaving at the next port."

"No, Will, don't say these things, luv...please, open this door..." Jack was almost begging, tears forming in his eyes. "Don't do this t'me, Willie. I love ye."

"You're a liar!" Will shouted again. "You're only trying to get inside my pants and then you'll leave. I should have known. You're a bloody pirate, and I'm going back to Port Royal."

"Will, open this door, luv..." Jack tried not to cry, but it was becoming more and more difficult each minute.

"GO AWAY!" Will yelled, and Jack jumped and released the doorknob. "I hate you!" Jack heard him before sitting miserably on the floor and putting his head in his hands. He cried out loud, not caring if his crew could hear him. Right then, Jack couldn't care less about his Captain's title.

He just wanted Will's forgiveness. But it seemed it was over for them both.

Head low, eyes red with tears, Jack stood up and went to grab some bottles of rum. It was going to be a long night.


The next day, Jack awoke around noon, with a terrible hangover. He had passed out on the deck after drinking himself stupid. Some crewmembers helped him lie down on another cabin, since Will had locked the Captain's cabin and wouldn't let Jack sleep there with him.

Jack groaned in pain as he woke. His head wasn't just hurting; it was /pounding/ all the time. It seemed his skull would break into a million pieces.

But Jack couldn't give a shit about the pain. Despite his hangover and headache, he noticed the ship was stopped at a port. Looking around like crazy, he spotted Mr. Gibbs on deck and asked him: "Where's me Will? Has he left?"

"No," Gibbs replied, and Jack sighed in relief. "But, Jack..." Gibbs said. "He's packing."

Jack didn't reply, and ran to his cabin. The door was unlocked and Will was there, eyes red and swollen. His expression was tired, as if he hadn't had much sleep at night. The bed was full of Will's clothes and he was packing them. When he noticed Jack had entered the cabin, he just sighed tiredly. "Would you leave me alone? I need to pack."

"Will, me love, please don't do this." Jack knelt before the bed, where Will was sitting, and took the boy's hands on his own. Even though Jack's head was pounding madly, he said weakly: "Ye are right, Will. I tried to buy ye with me presents. I tried shamelessly to woo ye so that ye would soften a bit and let me make love to ye."

Will looked at Jack, astonished. The bloody pirate still dared to admit it in front of him!! Will was going to yell some nasty things to him, but Jack took his hand and kissed it, and Will's words died on his tongue. That caress was soft and unexpected, and Will softened a bit. Then, Jack said: "What ye don't know, me love, is that sex for me is not dirty in any way, neither is it sinful." He kissed Will's hand again. "All I wanted was that we share a different kind of pleasure together, because I love ye, and I want to share it only with ye."

Jack raised his hand, and touched Will's face. Will was crying, and Jack wiped his tears. "What you don't know either, Will, is that even if my plans went wrong and you kept your position, I'd remain with ye, because I love ye. Is it so difficult to forgive me? Because all I wanted was that we share this moment together? Because I wanted us to be closer?"

Will remained silent for a long time, thinking about Jack's words, and his pain. God, Jack's eyes were so sad that Will felt his heart clenching. He didn't want to see those pretty eyes look so sad anymore. Even though, Will said: "You could have talked to me. You could have said all these things before you tried to buy me with presents."

"But I couldn't." Jack said. "I didn't talk to you, Will, because I did not want to push ye...I did try, once, but then I decided I wouldn't because I don't want ye to do it only because I'm asking ye to. I wanted ye to think about me reasons and decide fer yerself."

"What about /my/ reasons, Jack?" Will said, still serious and sad. "Have you ever considered them?"

Jack remained silent this time. The truth was that he didn't understand Will's reasons. They were so full of a moral Jack considered hypocritical. Why did Will let him suck his cock, but didn't allow buggering? It made no sense to Jack.

"Because I can't understand why ye do all the other things, and won't let me inside ye." He simply said. No need to upset Will even more by saying he was a hypocrite.

"I was told it was dirty, Jack. Unmanly."

"When ye suck my cock, is it unmanly to ye? It could be as well, couldn't it? That's what I can't understand."

Will didn't say a thing, but let Jack climb beside him, and they lay together along with the clothes. Will looked at the ceiling, considering Jack's words, letting Jack stroke his hair and neck.

"Are ye afraid?" Jack suddenly said.

Will looked at him. "Afraid of what?"

Jack avoided Will's eyes. "When I make love to someone, it means a lot to me. I put all my heart in it."

"That's what I like most about you," Will said tenderly, taking Jack's hand in his. They looked at one another in the eye. Their faces were inches apart, their breaths on each other's faces. Without fear, Jack pressed their mouths together, pulling Will closer to him. Will kissed back, hesitating once, but then melting in Jack's love for him.

They kissed for a long time, caressing one another, and Jack ended up above Will. Will's put his arms on Jack's neck and held him tight. "I love you." Will said, emotion in his voice. Jack kissed the side of his neck and said: "Are ye afraid of deepening our relationship?"

Will sighed: "Maybe I am."

They stayed there all day, together, embraced tightly. Jack was feeling so well that he didn't even care if they didn't do anything more sexual. Being embraced with Will was enough to him that day.

The crew was in port, buying things to restock the ship, and they would leave that night. When they left, after midnight, Will was still with them, embraced tightly with Jack, sleeping peacefully in his lover's arms. Jack was awake, despite his tiredness, running his hands on Will's hair while he watched his lover sleep. When he couldn't stand to stay awake any longer, he pressed a kiss to Will's forehead, made the boy put his head on his chest, and slept with a hand locked in Will's curls, just like he used to do.


The days passed slowly on the sea. Will and Jack were closer than ever, so in love that they elicited jealous grumbles from the crew. It seemed the fight had only brought them closer. Now they talked much more about their feelings, their disappointments, their opinions on subjects that each had his own point of view, which included sex. And though Will hadn't let Jack bugger him yet, he was giving more thought on the matter, and Jack was calmer, enjoying everything else he did with Will. Not only in bed, but the way they held one another, the way they kissed, the way Will held his hand. Both were trying to understand the other's reasons, and the relationship was much easier this way.

So, one day, Will entered Jack's cabin at night. The pirate was fully asleep, and Will smiled. He had been working until late, and Jack had gone to sleep, since he was very tired because he'd been at the helm all day.

Will took off all his clothes, and lay beside Jack in the dark. He wanted, more than anything, to wake Jack up and do wicked things with him. But he didn't want to wake his lover. So, he waited.

He didn't have to wait for long. Jack awoke, feeling Will's warm naked body beside him. He loved when Will did that. He always awoke already hard, because Will kept teasing his cock while he slept.

'Little minx,' Jack thought fondly, and kissed Will full on the lips, while he let his lover remove all his clothing as well.

Will grinned playfully and lay above Jack. They were so light with one another that they didn't expect anything, only to stay together, and to share good moments with one another. Jack loved to run his hands over Will's entire body, awakening his length, to rub their cocks together playfully. And Will just sighed in contentment because he was with the man he loved and desired.

Kissing Will's mouth, Jack changed their positions and lay above Will. Their caresses had become hotter and hotter during their 'entertainments' in bed. With Will's earlobe inside his mouth, Jack grabbed the boy's cock and started to stroke it. Will moaned aloud, and Jack kissed him again to cover those hearty moans. Much as he loved to hear them, he didn't want the crew teasing his lover the next day.

Feeling Will's breath quicken, Jack asked him, also breathing hard: "Tell me what ye want, luv. Tell me what to do...I want ye to lose it."

"Suck me," Will said, panting.

Jack did so, engulfing Will's entire cock in one swift movement. He tasted the drops of pre-cum, savoring Will's taste, and took all of his cock, only stopping when it reached the back of his throat.

Jack deep-throated him, suckling avidly, desperately. Jack was hungry for Will that night. He wanted to eat him alive, to engulf all of his cock inside his mouth, to swallow him whole until he choked. He wanted to swallow Will's seed, to make him lose control.

And Will was losing it. He bucked off the bed, fucked Jack's mouth with his fully erect cock, and moaned loudly. Jack gave him fingers to suck, and Will sucked them desperately, almost biting his lover.

Finally, Will released himself in Jack's eager mouth and lay tiredly on the bed. Jack was as hard as a rock to see Will losing control, coming inside his mouth, all sweaty, exhausted and utterly beautiful.

"I love ye," Jack said, lying beside Will, tracing the few hairs on his lover's chest. "Mmm, love you, Jack." Will replied, full of passion, and lay above him again.

They didn't stop there. Jack was still fully hard. He needed Will. "Suck me, darling," He said.

Will leaned over Jack and kissed him on the lips. Then, smiling slightly, he said: "I know you want more than that, Jack, and tonight I'm going to give it to you."

Jack's eyes were unreadable. He had stopped his caresses on Will's face. He seemed to be trying hard to control himself.

Jack looked into Will's eyes and saw the truth there. Saw the sincerity, though he saw fear too. Will wanted to do that. He was afraid, but, unequivocally, he wanted it. He wanted Jack.

He wanted Jack inside him. He'd finally understood. He felt Jack's love mark him so deeply that he couldn't shy from it. He knew he was loved, and he loved Jack in return. So, he wanted to try.

Jack didn't say a thing. He couldn't. He was overwhelmed with emotions, so deep they made his blood run hotter and hotter, making him entirely aroused just at the thought of finally having his Will that way.

"Kiss me," Will asked him. "Kiss me and do what you want to my body."

Jack looked at him, his eyes prickling, and kissed his lover like the world would end the next second. Will moaned happily inside Jack's mouth, feeling surer and surer of his decision. Jack felt a mix of happiness, relief...and, most of all, love. He had to make this perfect for Will. And he would.

Jack kissed Will for long minutes, running his hands on his lover's back. He could feel Will's nervousness, and stroked his hair to calm him. Jack assured Will they were going to do it slowly, at his pace. Feeling relieved, Will kissed Jack one more time and lay on the bed on his back. He was fully hard again, and Jack couldn't wait another second.

He grabbed the oil he kept on his pocket - he never knew when or /where/ Will would let him in - and coated his fingers. Will was looking at Jack nervously, biting his nails. Jack found that image so hot - Will with those long fingers in his mouth - and tried not to come right then.

Burning hot with Will all spread on their bed, Jack probed Will's entrance slowly, and the boy was so tight, and so aroused! Jack had to control himself not to grab him and fuck him without preparing. But he couldn't. Will would never forgive him if he did that. Maybe when he was more experienced...

Jack prepared Will carefully with one, two and three fingers. When it ended, Will was already bucking off the bed, begging for more. Jack had found his pleasure spot, and was teasing him there mercilessly. Will grinned at him, and moaned loudly.

When Jack withdrew his fingers, Will was tense again. Jack coated his member, and looked at Will in the eye. They were finally going to do it, and he was so happy! He wanted to say those things to Will, and so he did: "Will, me love, don't be afraid. I won't hurt ye..." And he kissed his lover slowly, softly, reassuring him. "I love ye so much...wanted this for so long...ye gave it t'me, and I love ye for this too."

Will, though still tense, softened and melted when Jack said those words and kissed him again. He barely felt the tip of Jack's cock touching his entrance, for he was so enthralled in the kiss that he just knew he was with Jack and nothing else mattered. Jack would never hurt him, not intentionally. Will had heard it hurt the first time, but he tried to relax his muscles and gave way to Jack's cock.

Still kissing Will, Jack entered him slowly, stopping whenWill tensed or moaned in pain. Jack reassured him with soft words, that the pain would only last for a few moments, and then he'd feel only pleasure. Will believed him, and let Jack take care of his body like no one else would. Will knew that. Jack was so patient with him. He felt loved.

After entering Will, Jack stopped for a moment so that his lover could adjust to his size. He stroked Will's hair, feeling his legs tightly wrapped around his waist, and Will felt no shame, that he was not commiting a sin, but actually practicing an act of love.

At Will's nod, Jack started to move. First, just a few, slow thrusts. Then, Will relaxed more, and Jack thrust harder inside him, feeling fully connected with his lover.

They looked at one another and smiled. Kissed. Grinned. Jack was pumping hard into Will now, and all the boy felt was pleasure and bliss. He closed his eyes, laying his head on the pillow, and just...felt, while he urged Jack faster by grabbing his butt and pushing Jack to him.

They kept that sweet, loving pace for a long time. In and out, in and out, and they didn't want it to end. They closed their eyes, feeling deeply connected, feeling that the world had stopped. It was only them, inside that room, on that bed, making love to one another. Jack took Will's face in his hands again, kissed him again, and said: "Thank ye."

Will replied by hugging Jack tightly, urging him deeper again, caressing his butt and his opening with slick fingers. Jack moaned loudly every time Will did that, pounded harder inside him, and babbled incoherently: "I love ye, luv ye, do that again, Will." And Will grinned and did just that. He loved to see Jack breathless.

"I'm gonna..." Jack groaned loudly, and came inside of Will, who held him closer. Just moments after, Will's release followed Jack's. Jack collapsed, exhausted, above him, and Will just stroked his hair and back, tears already starting to form.

In the aftermath, they held one another and Jack had no need to ask Will if he had liked it. He knew Will had. He just knew it. They kissed again, and stayed there, staring at one another for a long time, until the sun rose in the sky and they finally slept.

The End

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