Dan stopped, and within a split second, he pushed Kyle’s face against a small mirror on the wall. Kyle blinked and fogged up the glass, staring into his own face, horribly painted with bright red color. He looked like a drunken whore.
”Answer the captain,” demanded Dan in that voice he never used with Kyle out of a scene. Aggressive and merciless.
“No!” Kyle yelped despite his whole body yearning for cock. “I’m just a farmer,” he whimpered, but it got him a slap on the ass.
“Tell me how much you want my cock,” Leo said in a cooler voice, and Dan’s grip tightened on Kyle’s hair.
“I want it …” Kyle muttered, watching his own face, which looked as shaken as he felt.
“How much?” Dan pushed Kyle’s face into the mirror, smearing the lipstick on the surface and all over Kyle’s face.
“A lot, I want it a lot.”
“Maybe you should kiss the captain’s boots then?” hissed Dan and brutally pulled Kyle deeper into the cabin.
He pushed Kyle down to his knees and then lower until his lips and nose pressed against Leo’s ankle. The leather smelled of polish and was warm from the flesh it hid, and Kyle couldn’t help himself. He moaned, brushing his lips against the smooth surface.
“Both the tips,” growled Leo above him. ”Ass up higher.”
Kyle arched his backside up as he left lipstick stains on the captain’s boots. His anus throbbed with anticipation and slightly chafed from the panties. Just as he thought of that, Dan pulled the back of his dress up unceremoniously, startling Kyle so much that he yelped and tried to back away, only to bump into the captain’s legs.
“That looks good enough,” muttered Leo before yanking Kyle up. “Mr. Cocks, fetch me the oil,” he commanded, pushing Kyle toward the bed, which was covered with red velvety fabric. Tulle curtains were fastened to the ceiling around the bed.
“Aye, Captain,” said Dan, but that was all Kyle saw of him before collapsing on the soft mattress.
Leo pushed him farther and climbed on the bed after Kyle, pushing Kyle’s thighs apart without a shadow of hesitation. Kyle could only imagine how he looked with the smeared makeup, stockings over his legs, and the pink panties digging into his crack. His face throbbed with the mixture of arousal and humiliation, and his dick was rock-hard, already leaking pre-cum. Soon enough, he’d have cum dripping out of him to finish off the picture. After the captain was done with him, he would be fair game for any crewmember, and all of them would be allowed to unload on him however they wished. He tried to pull his thighs back together, but Leo pushed them farther apart again.
Leo’s face was already flushed, and as he looked down at Kyle with the single uncovered eye, the unfamiliar moustache only strengthened the sense of being overpowered by a complete stranger. Kyle tried to close his thighs, to keep the evil captain out, but when he felt the mattress dip close to his head, he knew it was a lost cause. Dan’s big palm closed on his mouth.
“Shut up or we’ll keelhaul you,” he said in a way that made Kyle almost believe the threat.
Dan could have been an actor with that big, menacing presence and the way he transformed so easily from a loving boyfriend into a cruel monster of a man.
Leo laughed and took a bottle out of Dan’s hand. “You’ll get your turn, but it’s my duty to make the hole big enough to fit all of my crew,” he said, and Kyle stirred when he felt touch through his lacy panties.
Fingers probed, bugged, but he still screamed when Leo tore the thin fabric open just enough to have access to Kyle’s anus without undressing him.
There would be nothing keeping him decent, and with his anus visible through a hole in the lace, he felt even more naked than when they’d undressed him. He squirmed away from the touch, but it was no use. Leo teased his hole with his fingers, smiling wildly.
“I’ll rip into that virgin hole. You’ll be no good for nothing but serving my crew after I’m done with you.” Leo breathed heavier, eating Kyle up with his eyes. “You’ll see what a real man can do to you, Princess.” He laughed and Dan undid the front of Kyle’s corset, revealing the top of his chest. “Good, Mr. Cocks, I love to see those nipples stiff for my dick.”
Leo put his thumb against Kyle’s lips while his other hand kept teasing him between his legs. Once he got a smudge of lipstick on his finger, he rubbed it onto Kyle’s nipples, making them red and prominent on the pale background.
“He’s no different from that wench we marooned on Tuesday. She was so used up no one wanted to fuck her anymore,” said Dan as his thick fingers slid over Kyle’s throat, pressing gently.
Leo cackled and opened the bottle, gathering some of the lube into his hand. The curly wig was stirring with each of his moves, the hair tossing around like that of a real pirate. Kyle was so captivated he lost track of what was going on and screamed when something pulled on the torn lace again.
Leo licked his lips in the most obscene way and pushed Kyle’s legs up. “Mr. Cocks, hold this bitch open.”
Dan moved quickly, the bulge in his pants brushing over the top of Kyle’s head as he grabbed Kyle’s ankles and pulled on them, leaving Kyle’s poor ass exposed and ripe for the taking.
“No, no, no!” Kyle whined, looking down his body at his own erection staining the lace with pre-cum and Leo’s thick dick disappearing between his ass cheeks.
The strong hold on his legs only added to the sense of complete helplessness. Leo’s cockhead pushed on his lubed-up anus, and there was no gentleness when Leo thrust it inside with a sated groan.
“Oh, this princess was definitely a virgin,” Leo muttered, pushing his cock in farther with a wolfish grin. “Go on, take it all, bitch. How’s it feel to have me inside, huh?”
“Answer the captain,” hissed Dan and pulled on Kyle’s legs until the muscles in the backs of his thighs screamed in protest.
His ass was now like an offering, completely open for the captain whether Kyle wanted it or not. He felt every ridge of Leo’s thick cock burying itself inside of him. And for the first time, someone other than Dan would be leaving him dripping with cum.
“It’s too big!” Kyle whined, uselessly writhing to move away.
“Just wait ‘til I actually start fucking that tight hole,” Leo said with a gasp when he pushed his whole cock inside. “You feel that? That’s all you’re worth to the world, gone. You’ll be a cumrag for my men from now on. Everyone will have a piece of you whenever they want. You’ll suck their cocks, take them up your ass, jerk them all off before bed if they want it. You get it, whore? You don’t even need a name anymore. Now tell me what you’ll be, or you’ll regret it.” He underlined his words by pulling out a bit, just to shove his rock-hard dick right back in.
Words rained from Leo’s mouth, and it already felt as if Kyle was being covered by hot, delicious, dirty cum. His imagination was working at full speed, and the way Leo was moving in his tight, unprepared hole only fostered the fantasy. Dan’s groin was shifting against Kyle’s head, but as much as Kyle longed to beg for it, for Dan so slap his dirty mouth with his thick meat, he couldn’t do that without breaking the illusion. So he thought of his boyfriend’s heavy sac dipping into his mouth and his cum on Kyle’s neck and whimpered, “I’m a cumrag for your crew. Please, don’t toss me into the sea!”
“What else?” Leo insisted as he began moving his cock in and out, ramming it in hard every time. He grabbed Kyle’s cheeks and squeezed them.
“I’m a whore, I’ll take anyone’s cum,” Kyle whimpered and he imagined his cock getting a lace pattern from the way it was straining against the panties.
“If I choose to spend a few day in Tortuga, I’m gonna make you the cheapest whore out there. You’ll be earning your keep in a tent at the pier, client after client, you little bitch,” hissed Leo, riding Kyle at a punishing pace.
Each time he slammed in, the mattress shook under Kyle from the power behind that movement, but even as he became sore, his whole body was elated, warm from excitement.
He imagined Dan as the pimp, sitting next to him and watching Kyle take dick after dick with his hands tied back, no clean up, just more and more cum pumped into him, spilling out on his balls and thighs. He wouldn’t even get to see the faces of the strangers who would fuck him. No, he’d just feel the pool of cum at his feet grow deeper throughout the day.
“Why?” whispered Leo, pulling out almost completely before pushing in so hard Kyle screamed.
“I’m a good boy, I just want to live.” Kyle closed his eyes tight and curled his feet.
“You will live,” said Leo, who suddenly arched over him, trembling. “You’ll just stop walking after a while,” he hissed out, closing his eyes.
His cock twitched inside Kyle’s hole, and Kyle shivered, realizing what the heat inside him was. Leo was coming inside him. He’d have all the guys do that. He’d have their cum inside his body.
“We shouldn’t let our princess wash, Captain,” Dan whispered and slipped his thumb into Kyle’s mouth. “Just leave cum to crust on his body in the sun. Filthy little cumhole.”
Kyle couldn’t help wiggling his hips at those words. Dan knew exactly how to get to him, but with his prostate only nudged every now and then and no one touching his cock, he wasn’t coming no matter how much he squeezed around the thick dick pumping cum into him.
Leo pushed his hair back and pulled out so abruptly, Kyle whimpered, shocked at the sudden emptiness inside him. “No. I want him to understand his place,” he said, but before Kyle could protest, Dan flipped him over and pushed on the back of Kyle’s head, shutting him up with the bedspread.
The skirt was lifted from Kyle’s ass, and he froze when something soft made a vertical line on his left butt cheek.
“There. Mr. Cocks, I need to keep track of the usage of this one so that we don’t end up with a ripped-up hole in the middle of the ocean again. All my men need to make use of their markers and tally every time they unload inside him. For the ass, marking at the back, for the mouth, tally at the front. And I am not joking this time. I will be making surprise inspections, and let no one underestimate the seriousness of this issue.”
“Aye, aye, Captain,” said Dan. “Should we limit it to twenty uses a day?”
Kyle whimpered and Leo gave his ass as slap so he settled down. Cum drizzled over Kyle’s balls, and he breathed harder at the thought that both Leo and Dan were watching him this way. Well used, with his legs spread, and a mark on his ass so everyone knew he’d been fucked.
Leo hummed as if he were giving the question a lot of thought. “There is five of us, so that sounds reasonable.”
Kyle squeaked when Leo dipped a finger between his ass cheeks and spread the cum over them.
“Some whores tell me my seed makes them feel energized. What do you think?” he asked, playing with Kyle’s ass.
Kyle pushed his face into the bedding, humiliated by the position he was in. On his stomach, with the skirt pulled up, and another man’s cum soaking into a pair of torn women’s panties he’d been forced to wear. He was so far removed from his usual prim and proper self, yet exactly where he wanted to be.
“I think he’s so amazed with your vigor, Captain, that he can’t speak yet,” said Dan, much to Leo’s apparent amusement.
“Very well. I think the crew waited long enough,” Leo said, and Kyle shuddered as soon as he felt Dan’s big, strong hands pull him up.
Chapter 3
“If you spill in the princess’s asshole or mouth, remember to record that. We don’t want to end up without a hole to fuck,” Leo said and patted Kyle’s ass through the skirts. Dan was carrying Kyle over his shoulder, and with his bound hands, he couldn’t possibly save himself if his man lost his balance. Still, Kyle never felt like Dan would drop him.
“Is the princess tight, Captain?” asked Derek. “Was he a virgin?”
Leo patted Kyle again. “Oh, yes, very tight. Took all my seed, whimpered, and cried. Didn’t you, you cock-hungry slut?”
Kyle’s eyes itched at the words. He knew they weren’t real, yet they stung somewhere where they both ached and created arousal. “I did. Please be gentle with me, I’m still sore …”
The pirates laughed, and a few tears spilled down Kyle’s cheeks when he felt Leo hitch his skirt up and expose him to everyone. As the wave of embarrassment hit him, it became even worse—or better, he didn’t even know anymore—when Leo pushed a finger inside of him in front of everyone.
“He’s not sore. He can take all your cocks and milk them dry. If he doesn’t do well, he’ll get whipped, so that’s what I call incentive.”
The pirates shouted their enthusiasm, their eyes hungry, their big cocks straining the front of their pants, leaving Kyle breathless with need.
“Did he bleed?” laughed Derek, but it was Dan who answered, slapping Kyle on the ass.
“He’s practically still a virgin.”
“Please, I really am sore,” cried Kyle, wiping his eyes on the back of Dan’s shirt.
Leo sighed. “Very well. How about a game? I do love games.”
“What are you thinking of, Captain Dick?” asked Jon, who Kyle knew was extremely excited by the way Kyle was exposed now.
Sloppy seconds were Jon’s thing, and until now, he’d only ever had a go at Kyle after Dan, but had to wear a condom anyway. Today, he’d get to fuck Kyle after four other guys filled Kyle’s insides with their spunk.
“Maybe we’d have the princess guess whose cock is fucking her? We’d agree to leave her alone for the day if she’s right.”
Derek growled. “If that happens, we’ll get to fuck her over the limit tomorrow!”
Dan put Kyle down, but he had to hold on, as his knees went so soft they slightly buckled. One by one, the captain introduced Kyle to all the pirates, so he’d know what name to scream when guessing. It always turned Kyle on to be fucked by strangers, and even the fantasy of it was hot. He’d have someone take his ass, and not even introduce himself, degrading Kyle completely, making only his body matter.
His heart hammered in his chest when Dan pulled him to a wooden chest with a rounded lid and had him bend over it. Soon enough, his skirts were hitched up and thrown forward, covering his head. He was yet again exposed to all the horny men behind him, and each one would get to have a go at his asshole, as he lay helpless and bound.
Someone pulled Kyle’s legs apart more. Someone teased his asshole with a coarse finger and laughed. Someone ripped a hole in one of his stockings and tickled his skin through it. Someone wiped him between the ass cheeks with a wet cloth. All the anonymous hands had him moaning and barely able to choke out a breath. He needed to get off so bad his whole body throbbed with need.
Kyle whimpered when warm hands closed leather cuffs around his ankles. Then, with a metallic clang, something was attached to one of them. He lost his breath when his knees were pushed even wider apart for the spreader bar. He loved this accessory. It left him completely exposed to violation, without a way out. He’d be bent over and waiting until they decided they were done with him, because there was no way for him to close his legs now.
“How do we decide who goes first?” asked Sam, and a thick-soled boot dug into Kyle’s exposed buttock, kneading it as if it were a mound of dirt.
“Let’s pull straws,” suggested Dan, and everyone hummed in agreement.
It was the captain who did the honors while Kyle waited motionless, spread out and blind to whatever was happening behind him. It was only his hole they were after, and they’d get it no matter what. He couldn’t flee while they were in the middle of the ocean on a vessel he couldn’t even operate. Only now it hit him there was probably someone else on the yacht with them if the ‘captain’ was busy fucking. Embarrassment at that thought was a wave that went all the way to the tip of his dick.
In any other setting, in his hometown, he’d never allow an
yone he didn’t know to see him this way, but here? No one knew him here. Even if they caught a glimpse of the action, it wouldn’t hurt Kyle in the long run. In the short term though, his arousal spiked at the fantasy of some middle-aged captain seeing what was happening and sneering at him, at what Kyle was allowing others to do to him.
The decision seemed to have been made, and the moment cold lube drizzled all over Kyle’s crack and spilled down his balls, he knew it was on. A pair of hands gripped his hips, and there would be no foreplay. A cockhead pushed at his sphincter, and then in one hard thrust, it was in him, forcing a yelp out of Kyle’s lips. He tried to assess the length, the thickness of fingers. It could be Sam or Derek, as Leo and Dan had bigger hands, and Jon wouldn’t go first.
“Captain! Captain Cock!” Kyle moaned as the man behind him began a punishing rhythm, which combined with the lack of pubes, told him at once that it had to be Derek. Kyle didn’t want this game to be over.
“Captain Cock?” Leo hissed, and smacked Kyle’s head through the dress. “That’s Captain Dick to you, slut! I hope you’re enjoying that cock up your ass anyway, ‘cause it’s not mine.”
Derek pushed his fingers firmer against Kyle’s flesh, holding him in an impossible grip as the thick column of his dick rammed in time after time again. “I will destroy your ass, whore,” he muttered, and Kyle didn’t even try to hold back his moans as his thoughts drifted between the humiliation of being raped by pirates, who didn’t even care to look at his face as long as the hole was available, and the illusory captain who wouldn’t participate in the play.
Or would he? Maybe not without a condom, but it would be exciting to have someone completely anonymous plow him, so Kyle yelled even louder, calling to the anonymous sailor. Derek didn’t last long and thrust in and out even as he came, which ended up with most of the hot cum sloppily dribbling down Kyle’s balls.
Kyle’s thighs trembled, and his balls ached for release, but he knew no one would care to give him relief. The next person to approach him started with pulling the lace panties under Kyle’s buttocks, giving him even easier access to his throbbing anus. Kyle clenched it almost involuntarily and got a harsh slap for it. The man had to be Dan or Sam.
Crazy Kinky Dirty Love Page 15