The first night on their way to Tortuga they quarreled over sleeping arrangements.
Jack maintained he had dibs on the captain's quarters, since he was /Captain/ Jack Sparrow, even if his rank wasn't a position the Royal Navy would ever legally recognize and they both were very well aware of that fact. Will "should just find himself a sleeping place somewhere else on board, a hammock or a coil of rope, something like that, you know". This, of course, did not go down well with Will. A short struggle at sword's point convinced Jack that since each of them was going to have to stand watch part of the night anyway, they might as well both take alternate turns at sleeping in the captain's bed.
That seemed to have settled the discussion and after feasting together on cold cuts, fruit and a rather excellent French red they found stacked away in the captain's liquor cabinet, followed by a nightcap of Port Royal's finest rum, they ran a last check on the ship together, securing the sails so one single man would be able to sail The Interceptor by himself while the other one slept.
Jack took first watch while Will closed the door on the sight of his unlikely partner standing at the steering wheel, the pirate's face a faint blur, his body carving out a black space in the star-filled night sky; he crept under the covers and fell asleep, the red wine and the events of the day proving a more than exhausting combination.
To be woken by a warm hand sneaking over his body. Over a particularly private part of his body to be precise.
He sat up with a start, swatting away the roving hand, fumbling for his sword, not finding it where he had left it before he fell asleep, and his face was very very close to Jack's, the pirate's breath striking over his cheek like an invisible caress.
"What the devil?" he demanded, rather more confused than angry. "Jack! What are you doing!"
Jack's hand snuck upwards again, gripping him firmly through his breeches and Will...
Gasped loudly at his own reaction to this unexpected action.
"Just checking some facts, my boy. Gotta know what's going on aboard my ship. Captain's duty, savvy?"
Will tried to wriggle away from Jack's hand, but not too hard, because, to be honest, the feeling was /very/ pleasurable. And it had been a long time since someone else had put his hand in that particular place. A /very/ long time. So, actually, it seemed his body tended to wriggle /towards/ Jacks hand and not away from it.
"Since we're sailing to Tortuga, the place where a man needs to be able to hold his own or be eaten up alive, and since any bad behavior on your behalf will poorly reflect on my reputation, there are a few things I need to know about you, Will. Move over."
Jack (a very very naked Jack) lifted the blankets and tried to slide into the narrow bed, but Will just lay there, stunned, unable to move, a stone in the bed, so in the end Jack just gave up and crawled on top of Will, the grin on his face only barely visible in the moonlight that shone daintily through the cabin windows. The pirate started to move his body over Will's, slowly, languorously, evoking another gasp from Will's mouth, even though the shocked expression on his face grew even more pronounced.
"Well, that answers at least one of my questions, boy. You're not a eunuch. Good for you. At least you'll be able to have some fun in Tortuga. Would've been a shame if all you could have done was drink the ale and watch. Unless, of course, you think sex's just a spectator sport, but judging from this," he said as he ground his pelvis once more against Will's suddenly painfully straining erection, "I doubt just watching will be satisfactory enough for you."
And it wasn't. It had been enough to watch Elizabeth grow up, become a woman whom he could secretly anguish over, but it wasn't enough just to watch Jack's face as he closed his eyes in ecstasy, his head arched upwards exposing a disconcertingly vulnerable throat.
Not nearly enough to just watch.
His hand slid upwards, all by itself, betraying him by its very movement and he pulled Jack's face against him, drawing in Jack's exhaled breath, tracing back the source of that still sweet scent of rum and red wine with his tongue. He never thought it would be like this, kissing a pirate. But he sure as hell wasn't a eunuch and really quite desperate to prove that fact to Jack. Not that Jack needed any more proof than his pleading noises and his pushing up against the lithe pirate's body.
"Whatever gave you the idea that I would be content just to watch, Jack Sparrow?" He whispered.
"Oh, you know," the muffled pirate's answer came, as he kept blowing hot circles of air on Jack's chest, heating up the thin fabric stretched over it with his devil breath. "I've seen you watch Elizabeth, seen your eyes glide over that luscious body of hers, which, I can tell you without hesitation, feels just as delectable as it looks."
"You lying bastard!" Will shouted, but his curse turned into a moan as Jack's lips reached his breeches and the other man tried to take Will's cock into his mouth right through the coarse fabric.
"Many things they say about me are true, and many are not. I am not a lying bastard, Will: In the end I always come true," Jack grinned and he quickly untied the laces of Will's breeches, his seaman's fingers deftly untying the knots, removing Will's pants in one swift move and throwing them carelessly on the cabin floor.
Jack grinned again, squatting on Will's legs, as the moonlight played over his high cheekbones, highlighting them, hiding his kohl-rimmed eyes in even darker shadows than usual.
"Off with the shirt, boy, I want to take stock," he announced and reached up, pulling Will's shirt over his head and throwing it on the floor as well, leaving Will lying on the bed, naked, his cock springing up as if to greet the other man.
"Well, the parts seem to be in working order," Jack stated as his hands slid over Will's chest, fingers caressing his nipples, gliding down over his abdomen, and reaching Will's cock, one hand cupping Will's balls, the other hand gripping him firmly.
"Now we only need to find out if they actually do what they were made for. I assume you are a virgin, Will?"
"I most certainly am not!" Will said indignantly and with a swift move he pushed Jack up with his legs, flipping him over so he landed on his stomach, evoking a heartfelt "ouch" from Jack's lips as he did so. In his turn Will now straddled Jack's legs, his hands resting on the other man's hips, kneading them gently, his fingers tantalizingly slipping forward, teasing the sensitive spots just above Jack's legs.
"And how can I conclusively prove to you that I am neither a eunuch nor a virgin Jack?" Will asked as he bent forward and started to lick his way down over Jack's naked back, tasting the scars, the ragged edges of flesh a path for his tongue to follow.
"Well, you could, of course, bugger me, Will. You know, it's actually quite confusing because when a eunuch is being buggered he takes it like a man, which he isn't anymore, at least not in the area that counts. Tongues, that's a whole other thing, you can lose your tongue and still be a man. Lose your manhood, however, and you lose your manhood. And don't you get me started on virginity. But do you know by any chance how it feels to get blown by a man without a tongue, Will?"
Will slid upwards again over Jack's body, feeling the soft swell of Jack's ass under his stomach, and he let his body rest on Jack's, lifting the hair and kissing the nape of his neck.
"Don't you /ever/ shut up, Jack?"
"No, I don't. Unless someone makes me. Or makes me come. I'm usually silent after a fuck. One minute after a bad fuck, ten minutes after a good fuck, and I have been known to shut up for half an hour after an amazingly good one."
"Well, if I want to get any sleep at all tonight I'll probably have to give it my best shot, don't I?" Will grinned as he sat up on his knees, squatting on Jack's hips, feeling the warmth of the pirate's body underneath him, the clenching of Jack's buttocks a delightful pressure against the spot between his legs.
"You do just that, boy, and I might show you the true highlights of Tortuga," Jack said and closed his eyes, his body turning limp and heavy, his breathing light and regular.
For a moment Will was at a loss because of Jack's odd reaction, but his interest in this man had been raised and demanded immediate satisfaction, judging from the sight of his straining cock.
He sat back on one knee, raising the other and pushed it between Jack's legs, a barely audible moan the only response. Emboldened he put his other leg between Jack's legs as well, spreading them with his knees. Jack groaned softly, his breathing hitched, then returned to the same light pattern again.
"You can do this, Will," Will thought to himself. "You know the theory, you know the practice, even if it's from the other side, it's not that hard. As long as you are, that is."
And with that thought he put his fingers on Jack's buttocks, spreading them and bending forward to lick Jack's cleft, tasting salt and Jack until he found the entrance, his tongue teasing the taut muscle, exploring the possibilities there.
"I have nothing to ease it, Jack," he murmured and sat up between Jack's legs, a hand resting on Jack's ass, kneading the muscles, the other one wrapped around his own cock.
"Check the left hand cabinet," the dreamy answer came, "if the captain of the Interceptor's a captain who's worth his salt there's bound to be some ointment. It doesn't do for a captain to bugger his cabin boy until he can't work or even sit. What's the use in that, eh?"
Will reached backwards and opened the door to the cabinet. Just like Jack had predicted there was a bottle of salve standing on the shelf, nearly half full. He took it, his hands shivering with anticipation and lust and something akin to fear.
"How did you know there would be salve in that particular cabinet?" Will asked as he opened the little bottle and spread the slick contents over the palms of his hands, over the tips of his fingers.
"First thing a cabin boy needs to learn, my boy. Put the ointment in the left hand cabinet so the captain knows where to find it and you don't have to take it without. Now will you get on with it? I'm starting to feel quite uncomfortable in this position. Do something useful, Will, bugger me, or go stand watch."
With those words Jack lifted his hips, presenting himself to Will, his head lying sideways on the bed, his hands on his ass, spreading himself wide for the other man.
The sight of Jack's naked body before him, being offered to him, nearly sent Will over the edge, and with a groan he slid a salve covered finger into Jack, another one following quickly, preparing the way for his twitching cock that lay against the back of Jack's leg.
"Are you sure, Jack?" Will growled, barely controlled passion corroding his voice.
"Don't you /ever/ shut up, Will?" The lofty answer came and after that it was like nothing he'd ever felt and done before.
He grabbed Jack's hips, already invitingly lifted towards him and positioned himself, the tip of his cock pushing against Jack's entrance. There were no more thoughts of restraint or fear or insecurity as his cock slid into Jack's body, past the muscle into the incredible heat that was Jack. By sheer power of will he managed not to come right away as he slid inside, becoming engulfed in a tight moist warmth that was beyond anything he had ever experienced. He owed it to Jack, he owed it to himself to make this into a night to remember for both of them. So he thought of drunken sword smiths and evil fathers-in-law, and, oddly, even of Elizabeth's smile, as he buried himself further and further in and started to thrust, angling himself so he would reach that point of pleasure that no man could truly enjoy until he had been taken like he was now taking Jack.
He didn't last long, though, and neither did Jack, for it had been a long time for both of them and when Will came, hard, his scream startled the rats that moved silently behind the wooden planks, causing them to scurry away as quickly as they could. Jack followed right after, his hand gripping his cock, spurting gaily over the linen sheets, while Will collapsed on Jack's body, completely spent, the sweat on his body cooling quickly in the cold night air. Until Jack started to move under him, groaning softly. Jack rolled over, pulled up the bedsheets over their sweaty bodies and he lay there, on his back, one hand over his head, touching the wooden headboard, the other hand drawing meaningless circles over Jack's stomach, his fingers entwining themselves into Jack's moist curls.
Jack turned over as well and lay silent, his eyes closed as if fast asleep, his legs slightly spread, hands folded under his head.
"You liked it, Jack?" Will asked softly.
"Ssshhhh," was the only answer. "Sshhhh."
And Will closed his eyes and drifted off to sleep, a satisfied smile still playing around his lips.
Until he was pushed out of the narrow bed, tumbling on the floor, his legs awkwardly tangled in the bedsheets. As he tried to get up, indignant, Jack raised himself slightly, his head resting on his hand, a cascade of beads and feathers and night-black hair falling over his grimy fingers, and grinned.
"Three quarters of an hour, I'm impressed. We are definitely going to try and break that record, boy, but right now I am going to sleep, and you're not because it's your turn to stand watch."
And with those words he turned around, pulled the bedsheets over his shoulders, leaving Will standing there with naught but a bedsheet to cover his shivering naked body, and fell soundly asleep.