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“Hey, I’m Jack,” Jack said, smiling his best winning smile. “I’m real sorry about this, but I’m going to have to fist you in a sec. That okay?”
He watched as Izzy tore his gaze away from the cabin window and the turbid waves below, and finally looked at him. Izzy's face twisted into a confused scowl.
“Do I really have a choice?”
“Hm,” Jack rocked back on his heels, the mattress bouncing beneath him. He tapped two fingers on his chin. “I mean, not really. Oof. Bit of a tricky one, hey. But I still think it’s polite to ask, don’t you reckon?”
Izzy’s scowl faltered just a fraction.
Jack chuckled good-naturedly. “I can at least try to make it nice for you, work you open slowly for him.”
He nodded to the thin purple curtain that separated the bed from the rest of the captain’s quarters.
“I hope you’re being respectful of my property, Rackham,” Hornigold called from beyond.
“Oh, yes sir! The utmost respect, for sure,” Jack called back. He turned back to where Izzy was laid out between his legs and lowered his voice. “He’s not such a bad, dude, despite the… well, you know.”
“Despite obliterating my ship, killing my captain and half my crew, and now forcing me to fuck him?”
Jack sucked his bottom lip in solemnly. “Yeah, I guess there is that.” He shook his head, trying to shake off the bad thoughts like a dog shaking off rainwater. “Okay. Mind if I touch you now?”
“If you must,” Izzy grit out.
Jack shrugged, grinned, and then dove in face-first, threading his arms through Izzy’s bent knees and hooking over his thighs. He buried his face in Izzy’s cunt, lapping with a long wet tongue.
Izzy jolted. “The fuck are you doing?”
Jack raised his head. “Oh. Yeah. Sorry.” He chuckled. “I just thought maybe this would feel nicer to start with. Do you mind?”
Izzy gave him a withering look but his knees fell open a little wider.
Jack dove back in. The guy tasted amazing. Kinda perfumed but in a guy way, like amber or resin. Maybe even honey. Not that Jack ever got to smell the good shit; it was only when he was running a bath for the boss that he could steal a quick whiff of one of his bottles of perfumed oil.
Izzy squirmed, but he didn’t seem to be ticklish.
Jack tried not to stare up at him. He concentrated on the task at hand, but it was hard not to focus on the way Izzy’s hips rolled whenever he licked over the guy’s clit. He brought his mouth up higher, sucking the small mound into his mouth while flicking it with his tongue.
“Is the new boy being cooperative, Jack? You have my permission to persuade him if not. Just don’t mark up that pretty face.”
“He’s being real good, boss!” Jack winked at Izzy. “You are, you know. Real good.”
Izzy glared.
“Would you mind if I used my hands too?” Jack whispered.
“You just said you’re going to fist me.”
“Oh yeah, I guess I did. Well, let’s work our way up to that, okay? Old mate’ll be busy for a bit yet. One of the other lads is giving him a shave.”
Jack strained his ears. Sure enough he could hear the splash of water and lathering of shaving soap.
“Plenty of time,” he added. He nodded at Izzy’s cunt. “May I…?”
“Oh. Yeah. I guess.”
Jack beamed. He returned to sucking Izzy’s clit, occasionally dipping down to swipe below it with his tongue. He waited until Izzy relaxed a fraction before he brought a hand up, rubbing over Izzy’s hole with his thumb.
From beyond the curtain, Hornigold began humming. It was a bouncy, carefree tune, one that Jack had heard many times. It wormed its way into Jack’s head and he found himself bobbing his head along, licking Izzy to the rhythm. Soon he was humming.
Izzy moaned.
Jack pulled back, surprised. “Was that good?” he hissed.
Izzy flushed and looked away, turning his head to the window again.
“I spose,” Izzy replied.
“Oh! That’s great then. I’ll keep humming.”
Someone began stropping a straight razor against leather. Seamus probably, or maybe Briggs. People were always falling in and out of favour. Jack was never a favourite, but he seemed to be kinda trusted at least. Although, maybe trusted was a stretch. Tolerated, the way a spider was left alone because it took care of pesky flies.
Izzy parted his legs wider, so Jack eased a finger in, curling it to follow the shell-like curve of Izzy’s cunt. Jack followed the slick pathway from Izzy’s clit downward, licking around his fingers. He sucked at Izzy’s inner labia, pulling his head back to see how long the folds would stretch.
“I hope you don’t mind me saying,” he said between sucks, “but you are really wet. You always like this or is this like a just when it feels good kind of thing? Like getting hard?”
Izzy’s mouth twitched upward. “The latter.”
“Oh fuck yeah! I’m doing this right then!”
“You don’t do this often?”
“I mean, I do, but like… well, he gets me to help out prepping guys sometimes and this is the first time in ages we’ve had someone with a cunt, you know?”
Jack added another finger, marvelling at the way it slid in like a razor through lather.
“How’s it going in there, boys?” Hornigold hollered, not sounding nearly relaxed enough.
Jack paused, feeling Izzy tense around him.
“Good!” he called. “He’s opening up for me real good.”
“You fisting him yet?”
“No, boss. But I’m nearly—”
“Hurry up and fist him. Seamus is nearly done with this shave.”
Jack grinned. Seamus was always meticulously slow, so ‘nearly done’ was more likely to be ‘barely started’. Plus Seamus always added in a massage at the end. If he took long enough, the boss might even doze off for a bit.
“And Jackie…”
“Yes captain?”
“I want all the holes open for me.”
“Right-o.”
Jack resumed fingering. He waited for Izzy to sink into it again and then slid a third finger in. Feeling no resistance, he slipped his pinkie finger inside as well and drew his fingertips together.
“You’re like really wet. I can fucking hear it.”
He pulled his hand out and held it up to the window—the late afternoon light soft and golden. He flexed his fingers wide, watching how minute strings of fluid webbed across the gaps.
“Beautiful,” he sighed. “Okay, here’s the bit where I fist you. Is that still okay?”
Izzy actually laughed. It was a short, hollow sound, but not without warmth. “Again, it’s not like I have a choice.”
“I guess you kind of do. Technically, you could refuse. There’d be bad shit that would go down from Captain H, but you could still say no.”
“That’s not actually a choice, Jack.”
Jack hesitated, the five fingers of his right hand lined up with Izzy’s hole but not yet pressed inside. “I think… Yeah, actually, I think you might be right.”
“I’m guessing you don’t have a choice either, though.”
Jack stared at him, his shoulders drooping. He felt a sudden pang in his chest. “Yeah. I guess not.”
Izzy’s expression seemed to soften. He bit his lip and rolled against Jack’s hand.
“Fuck, you really do like this.”
“I don’t hate it,” he said.
Izzy grabbed him by the wrist and angled his fingers in, twisting his fist and wincing. He guided Jack’s free hand to his clit.
“I think I’d like to kiss you,” Jack said suddenly. “Oh. But, no. I should probably—yeah.”
He frowned down at Izzy’s cunt, pressing in with gentle, shallow thrusts while rubbing circles over Izzy’s clit with his left hand.
Izzy still had Jack’s right hand by the wrist. He guided Jack deeper, tilting his wrist slightly. He arched back with another moan.
Jack could feel himself thickening in his pants at the view of Izzy basically fucking himself on Jack’s fist. This was bad. Jack wasn’t meant to be enjoying this.
Hornigold’s humming stopped.
“You lads aren’t having too much fun in there, are you?”
“No, sir,” Jack called. “I’m just getting him prepped for you like you asked.”
“Hm. Mind you don’t overstep, Rackham.
Jack waited until the humming restarted. He tried to shrug at Izzy without moving his hands too much.
“Don’t mind him, he’s actually a real softy underneath.”
“A real softy who wants me fisted open for him?”
Jack scratched his nose with his left hand, considering, then resumed rubbing Izzy’s clit.
“Yeah, okay, so he’s not the best guy in the world. Come to think about it, maybe he’s not that good of a dude. Then again, I’ve had worse.”
“Really?”
“Oh yeah. One captain used to whip us a lot—that was shit. Not even as a punishment neither, just like, for fun. Another guy would withhold food if he thought you were getting too chummy with another crewmate—he was always terrified the crew would mutiny, which we did, of course. Stupid fuck thought we’d be too weak from hunger. At least Hornigold feeds us.”
“Does he whip you?”
Jack twisted his fist just right and Izzy’s cunt seemed to give in just the right way, swallowing his whole hand up. Izzy winced. Jack tried to ease back but Izzy held him tight, keeping him in place.
“No, stay,” Izzy said.
Jack gave him a weak smile, his heart heavy.
“Was it alright for you, on your ship?” he asked.
“I liked my captain,” Izzy said. “He was… I liked him.”
“Fuck. I’m real sorry about that. I’m sure he was a tip top guy.”
He shuffled on his knees, trying to drop his shoulder lower. This fisting was real hard work. He wanted to say something about how he wasn’t the one who actually offed Izzy’s captain, but thought Izzy might not want to talk about it.
“You feel real good. Just in case you were wondering.”
“Yeah?” Izzy looked genuinely unsure.
“Yeah. Like, really warm. I reckon I could fall asleep like this. I mean, not actually sleep or anything coz I’m like, wrist-deep in you right now. But I could just be warm and stuff with you. Fuck, I don’t know what I mean. Don’t listen to me.”
“You’re sweet.”
“Oh my god, you’re gorgeous.”
Jack clamped his mouth shut, afraid he’d say more.
Neither of them spoke for a while, Izzy making needy little humming sounds while Jack tried not to moan along with him. Jack rocked his fist an inch backwards and forwards, feeling how Izzy’s body stretched to accommodate him. He’d done different versions of this so many times, and yet he was suddenly struck with how intimate it felt, being wholly inside someone.
He began pulling all the way out and sliding gently back in. He watched the way Izzy’s hole partially closed between thrusts in and out. He looked so different from when they’d started: all pink and slick and puffy.
“Oh shit!” Jack smacked his forehead with his left hand. “I totally forgot, I need to do the back too. Um, just let me… Here, breathe out with me coz it might feel weird when I pull out.”
He held Izzy’s gaze, modelling a long breath out for Izzy to follow along with. At the same time, he withdrew his fist.
He yearned to lick his hand clean—maybe even coat his dick with the slick and fuck himself through the best orgasm of his life—but unfortunately he had a job to do.
“How’s this feel?” he asked, drawing a tight figure-of-eight pattern over Izzy’s asshole.
Izzy smirked. “I’ve had worse.”
Jack grinned back at him.
“How about if I…” He flattened his fingertip and applied pressure.
“Yeah, that’s… mmm.”
“Okay, so, problem: there is oil here but it’s out there with him.” He laughed, the sound flat. “I can go get it, but it’s kinda nice just being in here with you. And I reckon you’re wet enough not to need it. But, if you want it, I can—”
Izzy reached down and began rubbing slow circles around his clit.
Jack lost his train of thought completely.
“I can… umm… Yeah, how about I just… just stay here with you?”
“I think you should stay.”
Jack’s dick skipped a beat.
He trailed his fingers higher, collected up as much slick as he could and swiped over Izzy’s asshole. He plunged a finger in.
“Mmm… I haven’t been touched like this in so long,” Izzy moaned.
Jack curved his finger slightly upward, trying to do all the things he liked. Prepping people for the captain was usually transactional or mindless at best—though he did like to keep it conversational—but he wasn’t used to thinking about pleasure.
“Can I add another finger?”
“Mmm… yes…”
Jack added another, and soon another after that, slowly working his way up to five. Outside, the sun was setting over the ocean, streaking gentle fire over Izzy’s skin. The silhouetted shapes beyond the curtain moved slowly in rhythm with the waves below.
“Hey, Jack?”
Jack started, lost in reverie. “Yeah?”
“Can you finger me again?”
“Can I—oh my god, fuck. Yeah, I can. Yes. Of course.”
He cursed himself inwardly for sounding like such a dickhead, but Izzy’s expression was dark and sultry. It was hard to get lost in self consciousness with this absolute fucking knockout laid out in front of him.
He slid two fingers back into Izzy’s cunt while he kept fisting Izzy’s asshole.
“Oh god, Jack… fuck…”
“Shh,” Jack hissed, smiling. “He’ll hear.”
Izzy writhed, his eyes sparkling. He planted his feet on the mattress and angled his pelvis up, rolling against both of Jack’s hands.
“God, please don’t stop…” Izzy moaned.
“I wasn’t gonna.”
“Oh right there… there… oh god, Jack…”
“Izzy, please…”
Hornigold’s chair scraped shrilly. “Too much mirth, boys,” he barked. “You better not be enjoying yourselves, either of you.”
“No, sir!” Jack called back.
Izzy was writhing all over the place. A breathy sob escaped his lips.
“Fuck, Izzy, you really can’t—”
“Jack, oh god, right there… right… there…”
“Izzy…” Jack cautioned.
“Don’t stop. Oh god, don’t stop! I’m going to… I’m gonna…”
Jack panicked, needing to quickly suppress Izzy’s wails while not having the use of either hand. There was a pillow—but, fuck, he didn’t want to suffocate the guy. Fuck! He withdrew his fingers from Izzy’s cunt and clapped his hand over Izzy’s mouth, muffling Izzy’s orgasm. For a second, he worried that he’d ruined it, but Izzy flailed through it, gaping against Jack’s palm.
With his hand over Izzy’s lips, all his attention narrowed down to Izzy’s eyes looking up at him with unmasked satiation and need. His eyes were wide but soft, his pupils unbearably dilated. Jack withdrew his other hand and crawled up the bed, suspending himself over Izzy. He ducked his head and kissed the back of his hand where it still covered Izzy’s mouth. He closed his eyes, kissing like there was nothing between them.
He pulled back. “I want to make love to you,” he whispered.
“I can go again,” Izzy breathed back.
Any thought of self-preservation was gone. Jack undid the top of his breeches with one hand and shoved them down only far enough to expose his dick. He took himself in hand and lined himself up with Izzy’s cunt.
“Are you sure?” he asked.
Izzy nodded. “I’m sure.”
“Wait. Fuck!”
It dawned on him that, despite the setting sun plunging them into twilight, their conjoined silhouette was equally as visible through the curtain as Hornigold’s. Jack strained across the bed to reach the curtain and pulled it back an eyeball’s width.
Hornigold was slumped back in the chair, a white towel wrapped around his head and neatly folded over his face. Seamus had his back to them, washing and wiping his razors.
Jack replaced the curtain and turned back to Izzy.
Izzy blinked slowly, his eyelashes fluttering. Jack’s heart fluttered and his dick throbbed.
“Please,” Izzy whispered.
Jack anchored his weight on his elbows. He leaned down, time moving impossibly slowly as their lips met and his dick slid home. They kissed passionately, Izzy’s lips parting for his tongue.
“If he catches us,” Jack panted, “he’ll kill us.”
He moved with Izzy, each long, deep thrust aching with pleasure. He arched back, looking up at the ceiling in an effort to block out the twin fear of getting caught and of not getting caught and taking this too far.
It already was too far.
Feeling Izzy’s hand against his face, looked down.
“Forget him,” Izzy said, stroking the stubble of his cheek. “Just be here now.”
He brushed his thumb over Jack’s lips. Jack caught it and sucked it lightly.
“I want you,” Jack moaned.
“You have me.”
Izzy trailed his hand down Jack’s chin and chest, before letting it fall back to the mattress.
Jack took Izzy’s face in his hand and pressed their foreheads together. His other hand sought out Izzy’s, their fingers interlocking.
“Jack… fuck me, Jack…”
Jack slid up deep into him, over and over, angling to the spot that made Izzy’s cunt tighten and Izzy’s knees squeeze against his hips. Every moan and choked-out whimper from Izzy was even more gratifying than the slick warmth enveloping his dick.
“Fuck, Jack… I’m gonna…”
“He almost ready for me?” Hornigold boomed.
“Ye—” Jack cleared his throat. “Yes, boss.”
Izzy ran nails down Jack’s back while his cunt clenched even tighter.
“Almost…” Jack called, his voice quavering.
“Jack… Jack…”
Jack kissed him, not trusting either of them not to scream. Izzy moaned into his mouth; Jack swallowed it down.
Izzy was thrashing now. Jack sought his other hand and held both above his head. He tried to still Izzy’s torso with his body weight.
Suddenly, Izzy broke from the kiss. He tipped his head back, his entire body arcing into a silent orgasm.
Jack clung to him, trying to keep pressure on the same spot inside him to help him ride the wave of it. He felt like a man clinging to a beautiful siren; hanging on for dear life to the very thing that was threatening to drown him. And fuck, was he happy to drown.
“Please… please, come in me,” Izzy whispered, recovering.
“Fuck.” Jack stalled. He looked into Izzy’s eyes. “I can’t. He’ll know.”
“I need it…”
“I should stop. We should stop. Christ, he’s already going to be able to smell me on you. And he’ll know that you came. Fuck.”
“Please Jack. I need it.”
Jack let go of Izzy’s hands. He pulled out and shuffled back, sitting up at the far end. It was dark outside now, at least no one would see him. He should pull up his pants up and pull back the curtain and get the fuck out of here before he said or did something really bad—like fall in love with the guy.
Izzy rolled over onto his hands and knees and crawled towards Jack. Jack tried to back up further, but he bumped up against the wall.
Outside, a chair scraped back. Jack could hear Hornigold standing and stretching.
“How’s my prize?” Hornigold asked.
Izzy placed his hands on Jack’s ankles, and caressed up his legs.
“Yeah, almost done, boss!”
“You were almost done a few minutes ago. What the fuck are you doing in there, Rackham? I don’t have all night.”
“I’m, uh…”
Izzy slid his hands beneath Jack’s thighs, and dipped his head, his mouth closing around Jack’s dick.
“I’m just experiencing some… minor complications.”
He glared down at Izzy, mouthing for him to stop while only half-heartedly pushing him away.
Izzy raised an eyebrow, his eyes daring Jack to refuse him.
“What kind of complications?”
Izzy wrapped a hand around the base of Jack’s dick, jerking and bobbing his head with one smooth motion.
“It’s, uh, all in hand, boss!”
“Should I come in there?”
“No, no! No need to come! No one’s coming!”
Jack looked down at Izzy and mouthed, stop please.
Izzy blew him faster, the corner of his mouth tugging wickedly upward.
I mean it, Jack mouthed, unable to wipe the smirk off his own face.
Footsteps sounded toward them.
Jack’s eyes widened. He looked at Izzy, pleading with him. He hunched forward, actively trying to drive Izzy back, but Izzy clung to him.
A hand touched the curtain.
Jack started, throwing his head back to smack against the wall.
At the same time, there was a knock on the door.
“Christ, who the fuck is that. Hold on, Rackham, I’ll deal with you in a moment.”
The footsteps retreated.
“I’m holding on,” Jack said quietly, unsure who he was even talking to. “I’m… holding…”
Jack ran his hand through Izzy’s hair, following the bobbing of Izzy’s head. He could feel Izzy’s lips travelling over the ridges of his dick and how blissed out he looked, like he was enjoying this as much as Jack was.
“Fuck, baby,” Jack hissed. “If you keep going like that I’m gonna—”
Izzy grinned around him and quickened his pace and pressure.
It was Izzy’s smile that tipped him over the edge. He bowed back, his hips stuttering and dick spurting while he shoved his knuckles in his mouth to stifle a screaming groan.
Izzy sucked him through it, swallowing every drop and only slowing once Jack’s body had finally stopped surging.
“Fuck, baby, I… fucking hell.”
Izzy sat up, rocking back on his heels. Jack barrelled forward, shoving him onto his back and covering him in kisses. He kissed into Izzy’s mouth, chasing the taste of their sex.
“Alright, that’s fucking done,” Hornigold announced from across the room. The door slammed. “Have you opened my boy up for me, yet Jack?”
“I’ve cracked him open like a barrel of rum, sir!”
Izzy giggled.
“Shut up,” Jack hissed, kissing him again.
Izzy wrapped his arms and thighs around Jack.
Jack kissed his mouth and cheeks and nose and forehead and back to his mouth again.
Footsteps sounded, coming closer.
“I really have to go, baby. I’m sorry.”
Izzy squeezed him and then relented, relaxing back on the mattress.
“Can we do this again?” he asked.
Jack pushed up to kneeling and did up his trousers. He leant over and kissed Izzy on the cunt and then flashed him his winning grin.
“It’s a small ship, baby. I’m sure you’ll work out where to find me.”
The footsteps stopped. The curtain tore open.
Jack looked up at Hornigold and let his expression fall into indifference. “He’s all yours, boss.”
As he walked through the captain’s quarters towards the door, he reflected on what Izzy had said about choices and the various bosses he’d had over the years. He caught Izzy’s eye as he closed the door behind him and winked. Maybe it was high time for another mutiny.