On his birthday Jim Hawkins reckoned himself a man, and ran away from home to become a pirate. As long as he could remember, Jim had dreamed of life on the open sea. After his father died, Mrs. Hawkins had her hands full running their Tavern/Cathouse, The Admiral Bimbo. She spent all her time serving drinks and changing linens, and so Jim was left to watch after himself. Countless hours he spent listening to the wild tales of adventure on the open sea that the drunken patrons would spin, heroics exaggerated for the benefit his mother’s serving wenches (and full service wenches).
All his life Jim listened to those tales and dreamed of adventure beyond his seedy home town. In his daydreams Jim formulated a wild plan to become captain of his very own pirate vessel. So he packed a satchel with food, and a small bottle of the house’s cheapest wine, swiped a large carving knife out from the kitchen and left on a grand adventure.
The Admiral Bimbo was slumped along the road in the hills just outside of Port Flint. Sneaking carefully along the ditch, Jim was sure his mother would notice him gone and come looking for him, spoiling all his preparations. Ducking from hedgerow to hedgerow Jim carefully made his way into town and from there, down to the docks to find a pirate ship.
Now, Port Flint was well known to be the home port of all sorts of disreputable types, (and indeed many of them stayed at the Bimbo while on shore) but even so you couldn’t sail into port flying the black flag. Jim’s plan was simple enough: if you can’t spot a pirate ship at least you can spot a pirate, he figured. So he waited by the docks trying not to attract too much attention while he looked for a Pirate amongst all the seamen flowing in and out of port.
The afternoon faded to evening and a cool breeze blew in from the bay. Jim grew chilly in the shadows and despaired of ever finding a real pirate. He considered just going home, but he knew that mother would tan his backside something fierce and so he resolved to wait a little longer.
The Moon was just coming into view when Jim finally saw what he was after. Swaggering in from town with one hand on the cutlass in her belt and the other clutching a rolled parchment was the most piratical woman he had ever seen. Tall, her skin darkened from the sun, she wore breeches instead of skirts, and, from a distance Jim might’ve thought she was a man if not for her massive upper deck which was just barely held in check by a crisscrossed harness of knives. Her charcoal black hair was run through with ribbons and beads, and pulled back under a bright silk bandana over which she wore a fine felt tricorner. What made Jim certain that he had it right was the black leather patch over her left eye detailed with tiny jewels in the shape of a skull and crossbones.
Jim slipped from the shadows and tracked the pirate across the wharf, hiding behind cargo whenever he thought she might notice him. Finally she bounded up the gangplank of a two-masted frigate. Jim hid and watched as the sailors on deck saluted the pirate as she walked by, and headed to a cabin in the stern. “She’s the Captain” Jim thought as he lurked in the darkness.
Night fell swiftly after that, clouds blew in from the sea covering the moon. On board, the gang plank was raised for the night, and most of the crew disappeared into the hold. Jim crept up to the edge of the pier and reached out and grabbed the line tying the ship to the pier. He intended to climb hand-over-hand up to the deck as he had heard in so many tales, however this was harder to put into practice than he had anticipated; and he promptly fell into the bay with a loud splash.
While Jim struggled to pull himself out of the water and up to the ship, on-deck the evening watch had taken notice of his activities. Deciding that this would be boarding party was of no danger to the ship, the Captain and crew were fetched out to view the rather amusing spectacle. Eventually Jim looked up from his struggles and noticed the entire pirate crew looking down at him and laughing; indeed,once he stopped splashing it was impossible not to hear the gales of laughter rolling over the deck like waves in a storm. At first he thought to hide, but as he had already been spotted, he just swam in place, his face burning with humiliation even as the rest of him shivered in the cold water.
After the laughter subsided a bit, the Captain called down. “I say there, having a bit of trouble are you? What exactly are you trying to do?”
Jim, cold, embarrassed and thoroughly unsure of what to say replied with frank honesty.
“I was trying to board your ship.”
Fresh laughter erupted on the deck but the Captain was un-phased.
“So you’re a stowaway then?”
Jim didn’t know what to say–he knew that stowaways were usually dealt with severely, but stowing-away was precisely what he was planning on doing.
“I wanted to join your crew.”
He shouted, hoping to avoid punishment. though by this point, he had given up all hope of anything but going home with his tail between his legs by this point.
“Join my crew lad, why didn’t you say so?”
The Captain gave a number of orders and various crew members rushed about until a rope ladder was tossed down. Numb from the cold and and exhausted from his struggles, Jim made slow progress up the ladder and soon the crew began to pull it up, along with him, speeding his ascent. Hands gripped Jim all over as he spilled over the rail. and onto the deck like a dead fish.
“You must be freezing” cried the captain, with what was possibly mock concern, “get him out of those wet clothes, and bring some warm blankets.”
Lanterns soon lit up the deck as the hands of the crew quickly stripped the wet clothing off of Jim’s body and roughly dried him off with blankets, which were whipped away when he was dry, leaving him nothing to cover himself with.
Standing naked in the cool night air on the deck of the pirate ship he had worked so hard to board, Jim became acutely aware of two things: one, the entire crew of this ship seemed to be made of of women, and two, the cold salt water had shriveled his cannon and balls to an unflattering size for a boy even half his age. He awkwardly tried to cover up as the captain and crew appraised him like a freshly, won bounty.
The Captain struck one leg out swept off her hat, and bowed deeply.
“I am Captain Giovanca Belladonna Ramsey and I welcome you to my ship, the Hidden Pearl.”
Shivering, Jim bowed, though not as deeply and replied:
“Jim Hawkins, at your service.”
While the crew snickered, and whispered amongst each other, Captain Giovanca was completely nonplussed.
“Young Master Hawkins, if I may inquire why do you want to join my crew?”
Through chattering teeth Jim stammered out:
“Y-yyou’re p-pirates right? I want-t-t to be a p-p-pirate.”
This response brought laughter forth from the crew, but Captain Giovanca just smiled. “You want to be a pirate, aye? Do you think you’re up to the challenge?” She sneered as appraised the boy’s shriveled wedding tackle
“I don’t think you’re equipped even to be my cabin boy.”
The crew laughed even louder at this. Jim almost wanted to cry, but he managed to get out
“Please ma’am, I’ll do whatever it takes.”
From the appreciative chuckles that spread amongst the crew, this seemed to be exactly what everyone onboard wanted to hear. “Very well,” said Captain Giovanca.
“Let’s have a challenge to see if you’re capable of the duties of my cabin boy. Kylie!”
she said to her first mate: “Fetch Long-John Silver from my Quarters, and someone grab some grease from the galley. Sammie,” indicating her red headed quartermaster. “Get him warmed up for me.”
Jim was too stunned to react as several of the pirate crew picked him up by his limbs and laid him out on a blanket in the middle of the quarter deck. Just as quickly lines were produced from all sides and lashed to his wrists and ankles leaving him supine and helpless, pressed in on all sides by the warm bodies of hard pirate women who looked at him with hungry eyes.
Sammie, who had been standing to the left of Jim, began pulling off her clothing as smartly as she could muster. Her creamy, smallish, breasts popped into view from beneath a rakish leather vest. A dewy thicket of red pubes followed as the quartermaster dropped her breeches on the main-deck and stepped out of them, towards the defenseless lad.
Several other crew members were also disrobing, and fondling themselves and each other as they looked on hungrily.
Sammie meanwhile, stepped wide to either side of Jim’s shoulders and dropped to her knees. Lowering her foxtailed womanhood onto Jim’s face she said: “Come on lad, it’s well past suppertime, you best eat up.” The pirates all yelled similar encouragements as she ground her musky cunt into Jim’s face.
For his part, Jim had never even seen a girl naked before. His mother might be running a cathouse, but she kept Jim away from the guest rooms. Once, he saw a customer pull one of the girls, tits out of her blouse on the tavern floor and start sucking on it, before the girl pulled him up stairs. That memory was still what Jim masturbated too. The most he had ever done with a girl was kiss the cook’s son on the lips. Suddenly having a wet girl grind herself into his mouth, was a bit overwhelming, to say the least.
“Come on, boy,” Sammie worked her fingers through his hair and pulled him into her cunt. “If you want to be a pirate, you’d better learn to use your tongue”
Jim parted his lips and was immediately rewarded with the taste of Sammie’s cunt, which were spread thick over his face by now. She was salty and sour but Jim was eager to taste more of her. The action had brought some wind back into Jim’s sail, and he gasped when he felt a warm mouth envelop his five-inch main-mast in one go. Instinctively he thrust into the mouth of the unidentified pirate, while Sammie’s cunt ground harder into his face to make up for his sudden distraction.
“Lick, Damn-you, I’m almost there!” she snarled.
The warm mouth on his cock went away and was replace by a strong hand gripping positioning it upright as the crew member unceremoniously took his virginity. The woman fucking Jim leaned forward and kissed Sammie on the neck. Sammie tried kissing over her shoulder but couldn’t get enough of her crew-mate, so she swiveled around, crushing Jim’s head against the deck until she was facing her crewmate, Juliet, a curvy blonde whose tits she attacked with her mouth immediately and voraciously.
Sammie began to shake and shudder on Jim’s face. His tongue was bathing her clit with attention when she squirted right in his mouth. Moaning, she rubbed herself gently along his tongue until the Captain’s voice rang out, “Sammie, Juliet, get off the boy, it’s time to see if he can handle Long-John silver.”
The girls reluctantly got off of their ride, Jim still humping vainly at Juliet’s receding pussy. They rejoined the crew who, Jim could see now that Sammie’s thighs weren’t the way, were fingering and licking and rubbing against each other as they watched the action unfold.
Kylie, held in her hands a heavily ornamented little chest, about a foot wide and eight inches deep. She opened it for Captain Giovanca at an angle so that Jim could see what it contained.
Inside nestled in velvet, was a large, curved, silver phallus with a head at each end. Long-John silver was just over foot long. It curved smoothly with a raised ring and apparatus about a third of the way along its length separating the two ends. The shorter, curved-end had a wider head flaring out from the shaft, whereas, the longer, straighter-end was more like Jim’s own penis (though a good deal larger).
A stark-naked young man, infact the only male crew-member Jim had seen, appeared at Kylie’s side and plucked the dildo from the chest and walked over to Jim’s head while Kylie helped Captain Giovanca into a belt and harness apparatus also from within the chest.
“Open wide!” Said the young pirate boy kneeling beside Jim’s face. Jim however was revolted at the idea of anything cock-shaped coming near his mouth, and tried to shy away. His reluctance was useless, tied to the deck as he was. “C’mon lad,” the boy chided “you’re going to want it warmed up, I know from experience.” He rubbed the cool metal of the short fat end on Jim’s lips till he finally relented and opened his mouth hesitantly.
Immediately, he shoved the entire five inch length of the short side all the way into Jim’s unwilling mouth. Jim gagged and spit and bit the silver cock in his mouth but it was no use. The boy held it firmly, the cold silver ring separating the two sides resting on his lips, the tip tickling the back of his throat. Then, just as quickly, he swallowed his way down the long end until their lips were pressed together in a gentle kiss. He looked up at him with watering eyes and she gave him a wink and then started bobbing her head up and down the length of the shaft, giving the watching crew a show, but keeping it firmly in place as Jim sputtered and gagged on the silver cock.
Another crew member sidled up behind the the young boy and roughly gripped his cock, causing him to moan appreciatively around the phallus in his throat. His drool dripped down and mingled with the cum already covering Jim’s face.
Jim throat was just beginning to stop spasming when Captain Giovanca called out. “all right Charlie sweetheart it’s warm enough bring it back to mommy. The Captain’s son bottomed out on the silver cock and holding it in his throat pulled away from Jim. He kept it in his throat as he crawled on her knees over to where his amazonian mother stood naked except for the gold bangles on her arms, her boots, hat, and the queer leather harness around her waist and thighs.
Giovanca was being serviced by her first mate, Kylie, who was licking away between the straps of the harness.With a precision that comes from years of experience, charlie scooted in and using just his mouth inserted the fat head into his mother’s waiting cunt.
The Captain snapped the harnesses apparatus into place holding the tool fast inside her. Her son bobbed his head a few times fellating his mother (as he no doubt might have done for his father if anyone knew who the hell he was). Giovanca patted her son’s head gently as she pulled her silver cock from his slurping mouth.
A few crew members lifted Jim’s hips, and pushed a rolled sailcloth under his tail-bone, Another swooped in and smeared a scoop of grease between his butt cheeks. Jim strained against his bindings and Giovanca knelt between his legs. Charlier rushed forward and whispered in his ear, “Try to relax and it won’t hurt as much, try to enjoy this.” and then he kissed him on the mouth. The older boy’s tongue probed into his mouth and jim was surprised to find himself opened to it. Charlie sucked Jim’s tongue into his mouth, and then Jim felt the warm tip of Long-John press against his hole. Charlie tweaked his nipples, while Giovanca stroked his cock with strong fingers.
Jim tried to relax to the sensations enveloping him, then Giovanca struck home. It didn’t hurt immediately, but then Jim he realized the silver cock was inside his ass and panicked, his ass tightened and tried to repel the invading cock. Jim cried out into Charlie’s mouth, and he pulled away to let his mother fuck the young boy.
“Oh hush up, you scurvy bitch. Relax your fuckhole, and this will get better in a hurry.” Giovanca pushed steadily into his tight ass, and Jim cried like a boy being buggered on the deck of a pirate ship. A lot of the crew seemed to enjoy the sadism of the act and there were quite a few climaxes going on as Captain Giovanca leaned in and smothered Jims cries with her massive mammaries. “Jim lad, nurse on my tits till the pain goes away.” she said, grinding into him all the while.
Jim did begin to suck on the nipple in his mouth, the pain in his ass was unbearable so he focused on sucking as hard as he could. Giovanca finally bottomed Long-john silver into the teens ass. He was crying and sucking on her nipple so hard it hurt. God, she loved virgins. She ground her clit against the apparatus and waited for Jim to relax so the real fun could
Eventually the pain in his butt faded to a burning warmth and a fullness unlike anything Jim had ever felt before. He breathed in deeply and tore his mouth from one tit to the other. Sucking and licking Giovanca’s tits like he had always wanted to do to any of the girls working for his mother, this was so hot. the memory of pain fading already.
Giovanca for her part took his lack of sobbing and enthusiastic mauling of her breasts as a sign to proceed. and she withdrew a few inches and slid back in, nice and easy in and out she humped steadily into the young boys ass reveling in the power she exerted. his dick rubbed and poked at her navel with every thrust.
Increasing speed Giovanca pulled her breast back from Jim’s mouth and called “Give more slack on his legs.” She lifted him up by the waist improving the angle so she was pulling almost all eight heavy inches of the long side out of Jim, stopping with just the head of the cock still inside him.
Jim was groaning now. Captain Giovanca fucked him silly, the Silver cock that had hurt so bad was now rubbing his insides so good.
Giovanca was fast approaching climax; cheered on by her loyal and horny crew. She squeezed her end of Long-John tight as she began to cum torrents. Buckets flooded out of the Captain, a veritable white-squall dribbled down the strap-on apparatus, soaking the confluence of their bodies. She pounded ever faster as she came hard into the boy.
Jim let out a sharp cry, and his bouncing cock throbbed and spurted so hard that the first glob of cum flew almost five feet to land on Juliets fine bosoms where it was quickly sucked up by an appreciative sailor. Several more bursts flew through into the watching crowd, before his range was shortened so that the last of his jizz landed on his face and in his open mouth.
Captain Giovanca sighed and withdrew from the boy’s sweet little fuck-hole, she got to her feet unsteadily and asked “So Jim lad, do you still want to be a pirate.” Jim could only nod. “Welcome aboard then, from now on you will obey any order given by any member of my crew at any time. You will lick, suck, drink, or do anything they tell you to. Is that clear?”
“Aye-aye Captain” Jim sighed happily.
“OK crew he’s yours for the night, anchors away at dawn, so don’t stay up playing too late.” She noticed Charlie eyeing Jim’s softening erection. “Charlie come with mommy, you can play with him in the morning. Let the crew have some fun tonight” Charlie pouted for a second until he noticed that his mother had not removed the strap-on as she sauntered to her quarters.
He scampered after her mother as the the crew surrounded young Jim. It would be a long night for both of them.