2 comments/ 71761 views/ 16 favorites The Makings of a High Seas Whore By: Twisted_Mistress Caitlin has run away from her strict father to join the man she loves in America. Without help from her father she had no money to pay her fare so she decided to work her way across the ocean. There was, however, precious little work for twenty one year woman without references, none that she cared for anyway. Caitlin hurried through the galley carrying the sack of flour she had been sent for. Life on the seas was not the adventure she had thought it would be. Despite her attempt at speed she still received a clout across the ear for her tardiness. Mr Phelps was an impatient taskmaster and Caitlin tested that patience more than anyone else on board, or so it seemed. Though to the slap happy cook on the SS Good Morrow Caitlin was Craig; the cook's boy. Caitlin had thought that working aboard a ship would be an easy way to make her way to the new world. She had cut her hair and strapped her breasts flat to her narrow ribs in the belief that there was little else to worry about. In six weeks she would be in New York and able to find Michael, her soon to be husband. But life on board ship was not that simple. With her shorn hair and her newly flattened body she looked like a boy despite her twenty one years; in the mirror she looked no more seventeen. The short hair, calling herself Craig and wearing men's clothing was not all there was to working in the galley below decks. The hours were long; from dawn to long after dusk. The work was hard, she had thought her father to be a demanding man but he was almost placid in comparison. Caitlin's arms ached as though they might fall from her very shoulders, her back protested every movement and her head thumped with the tension from keeping her voice low and manly. If that wasn't bad enough she needed to pee and she couldn't do that until everyone else was asleep. How else would she explain the need to crouch and pee instead of standing at the rail and relieving herself like everyone else. She longed for her hammock and the short nights sleep it offered. It had taken her awhile to be able to sleep in the quarters with the rest of the men. Their bawdy talk had made her blush deeply, it became even worse once some of the men had noticed her, or rather Craig's, reaction. Fortunately they simply thought her, or Craig, to be a virgin. Unfortunately, they had also decided to take her to the first cat house available on the next shore leave to relieve Craig of that burden. With her ears still ringing Caitlin headed back to the stores to fetch a bowl of sugar for the apple pie Mr Phelps was making. The food was nearly ready; the officers had been served and the rest of the crew were tucking into their broth. There was only the washing up to be done before she could climb into that hammock and get a few hours sleep. Caitlin wiped the last pan dry, hanging with the others over the vast stove. A noise behind made her jump and she dropped the huge pan. It clanged louder than Big Ben itself making her jump back with shock. "Stupid boy." Cursed Mr Phelps. He grabbed Caitlin by the upper arm and swung her back from the stove, hitching the large stockpot to its hook with only one hand. "Give me one good reason for not whipping you boy." Hissed the cook. Caitlin looked at the floor, her eyes wide with fear. She shook her head fiercely. "I...I can't think of one sir. But please.." "Please what?" The cook knocked the cap from her head in loose-fingered swipe. Caitlin could smell the rum on his breath as he loomed into her face. Mr Phelps was as wide as he was tall with a huge belly. He was a petty impatient man during the day but he was not so pleasant when he had a drink inside him. Caitlin had heard tales of how the last cooks boy had nearly died at his hands just for breaking one of the officers wine glasses. "Well?" Phelps gave her arm a shake, it was like being held by a rabid dog. He looked down at her fearful expression and licked his lips in a manner that made Caitlin's stomach roll with fear. "I...I am very sorry sir. I am trying really hard." She whispered, trying hard not to squeak. Phelps looked down at the young boy, his eyes glittering with malice. He raised his hand, making Caitlin flinch for the blow to follow. She opened her eyes in shock when the hand that touched was not a blow but light fingers trailing her jaw. Her breath caught in her throat as fear for more than the accustomed casual violence welled inside her. The fingers trailed lightly down her throat and slid along to cup the back of her neck. "Such a pretty boy; how old are you Craig?." Phelps murmured his eyes looking Caitlin up and down. The strange expression on his face making her tremble with unknown terror. She had been warned many a time by her stern father about the uncontrollable urges of men around young women, but what could possibly happen to her when all around thought that she was a boy. "Nineteen." She said quietly. When she had first signed up she had told the man her true age of twenty one but with her soft face and delicate bones the man had not believed her. He had rolled his eyes when she told him nineteen but he had not questioned her further. The hand gripping her neck suddenly pushed her sideways against the large pastry table. Like the rest of the furniture on board ship it was firmly bolted to the floor and as such did not give way as she fell against it. She caught her ribs hard on its edge and felt the air fly from her lungs. Before she could draw air into her burning chest Caitlin felt the large hand return to her neck. No longer stroking her gently, now it pressed down firmly holding her down against the table. Phelps ran his other huge hairy hand across her back. He stroked downwards until his free hand cupped her buttocks. He gripped and kneaded her soft flesh as though it was dough. "Such a pretty boy." Phelps leant over her and muttered into her ear. Caitlin could feel something long and very hard pressing against her bottom. Fear held her still as Phelps slid his hands between them and fumbled with his belt. His breath was hot fumes on her cheek. His hand moved to the front of Caitlins trousers. As his fingers found the knot of the cord holding up her own trousers he pressed himself harder against her. The thick hard column rubbed her, parting her buttocks and pressing against her through the rough cloth of her breeches. Wild with panic Caitlin wrenched herself from under the coarse man. "No!" She screeched. In her panic she stumbled over the mans foot and was sent sprawling to the floor. She hit her head on the door of the stove and had to fight to stay conscious. Phelps loomed over her, his fingers gripping her arm tight enough to bruise as he dragged her upwards. Pulling against him Caitlin was only just able to stop him dragging her to her feet, desperate to keep him away from her body. It was not just the fear of his perverted violation but also the fear of discovery that filled her. However, the sight of her cowering before him on her knees seemed to give Phelps fresh incentive. Keeping his fingers around her elbow he fumbled with his trousers. Caitlin looked up at him in confusion. With a cry of triumph Phelps gripped her other arm and pulled her against him. Caitlin was pulled headfirst into his exposed crotch. She screamed as his hard cock pushed against her cheek. She could smell stale piss and worse as he ground against her, forcing her to close her eyes to him. "You want to protect your virtue young man, then fine. We'll save that fun for another day. For now you'll suck it." He hissed. When Caitlin shook her head he cuffed her hard around the ear causing her to see bright lights. "We can go back to my original plan if you prefer." He began to drag her back towards the table. Caitlin tried to dig her heels into the wooden floor but couldn't stop the large man from dragging her. She shook her head desperately. He stopped half way to the table and jiggled his cock before her eyes. With a glance towards the table and what she imagined might happen there Caitlin let out a deep breath and gave a small nod of resignation. Phelps pulled her up to her knees once more and stroked his erection over her face causing her to shudder in disgust. "Anytime sign of teeth and I will beat you senseless and take your arse anyways I like." He growled at her. His tone was softer now that he was close to getting what he wanted. Blinded by tears Caitlin nodded her understanding. Before she could brace herself she felt the hot gritty cock pressed to her lips. She was overwhelmed with the smell of piss emanating from him and opened her mouth with a reluctant moan of disgust. As soon as she unclenched her jaw the cock was pushed deep into her mouth. Caitlin had to fight herself not to pull away. For a few moments she stayed on her knees with her mouth open allowing the cock to be thrust in and out of her mouth. The taste of it on her tongue made her want to gag, the smell of Phelps' crotch and the sight of his huge hairy belly bouncing before her eyes sickened her. Phelps dragged her from her shocked daze by grabbing her by both ears. "Use your tongue boy, suck on it and let me feel your tongue." He hissed. Tentatively Caitlin poked at the filthy cock with the point of her tongue, Phelps issued a deep groan and thrust forward. This was the first cock Caitlin had ever seen let alone tasted, she was unclear on just what exactly was happening. She was almost confident that if Phelps enjoyed it then it would be over sooner. More than that though, she was definite that if Phelps didn't enjoy then she would suffer for it. Closing her eyes to her own humiliation Caitlin curled her tongue around the shaft and allowed Phelps to move her against him in a bobbing motion by tugging on her ears. The thick cock slid between her lips, across her tongue and pushed against the back of her throat. Rolling her eyes upwards she watched the huge man standing over her with a glazed expression. Caitlin began to bob her head independent of the horrible man and was rewarded with another deep groan. He spread his legs as wide as he could with his breeches at half mast and thrust his hips against her rhythm; forcing the cock deeper into her mouth and making her gag. Again and again he pushed into her. She closed her lips around him, careful to keep her teeth from his flesh, sucking hard as he pistoned deep into her throat. The more excited he got the harder it was for Caitlin to try and draw breath as the thick cock pushed down into her throat. Her throat felt raw with the pressure from his thrusts and the need to keep swallowing back the bile that rose from her belly. After what felt like an eternity she became aware of some change that occurred, Phelps' thrust became more savage and his cock seemed to grow even thicker somehow and then he thrust deep and didn't pull back. With his hands on the back of her head the man gripped her fast to him pushing himself ever down inside her. Caitlin swallowed and tried to draw breath but couldn't. She tried to push herself away, beating her hands against that huge round gut before her but was no match for his strength. Just when she thought that she would pass out she felt a hot rush of thick viscous liquid pour down her throat. It was too deep for her to taste any of it, and for that she was thankful. Phelps withdrew a fraction allowing her to drag air into her burning lungs before he plunged back inside. He continued to pump his softening cock between her lips, wiping foul tasting salts onto her tongue until his cock had finally stopped twitching. With a satisfied sigh he pushed her to the floor, laughing at her shocked expression and her burning cheeks. "Not bad Boy!" He laughed with an evil smile. "We'll add that to your chores from now on." With that he left for his bunk adjusting his trousers as he left her in despair. Caitlin stayed on the floor of the galley for a long time; not wanting to creep to her hammock until she was certain he would be asleep. This ship that she had thought to be nightmarish before had become Hell itself for her. The next morning after she had stoked the fires in the stove Phelps cornered her in the depth of the stores. Without a word he knocked her to her knees and raped her mouth once more. Thrusting even harder and deeper than he had the night before. This time after he had sprayed his filthy seed into her throat he stroked his wet cock across her cheek. Caitlin was able to smell him on her for the rest of the day until after dinner when he forced himself on her once more before retiring to bed. The Makings of a High Seas Whore Ch. 02 Twenty one year Caitlin has run away to join her love but without help from her father she was penniless. So she had joined the SS Good Morrow disguised as a cabin boy. She planned to work her way to America on board but could not have planned for a cook with a taste for cabin boys. Only days after Mr Phelps' rough induction to his brand of oral sex Caitlin's days had assumed a new and decidedly unpleasant routine. Rise at five to stoke the kitchen fires, wait in the store room on her knees for the cook to fuck her mouth until her spewed his seed deep into her throat. Thankfully, with the practise she was getting, her technique was improving and Mr Phelps had stopped threatening to force himself inside her arse. Caitlin had tried to avoid him, attempted to stay close to the other men working below decks but to no avail. It seemed that trying to elude him only resulted in his attentions being even more ardent at the next opportunity. The sea was so rough when Caitlin fell from her hammock at dawn that morning that she had difficulty keeping upright as she staggered to the galley. It was with great caution that she poked at the fire to reignite the embers. She added fuel and quickly closed the door; she knew that they would most likely be having cold cuts today. The weather was such that Phelps would not risk the chance of flying pans of boiling water. With a deep sigh of resignation Caitlin dragged herself to the stores. Moving slowly towards the high shelves at the rear of the room Caitlin knelt down between two barrels of rum. Her stomach roiling at the smell; she would forever connect the thick smell of dark rum with her humiliation. Only moments later she heard the deep rumble of Phelps' footsteps on the boards. She heard him press the door closed and then felt the boards tremble beneath her knees with each swaggered step he took. Her stomach rolled with fear and disgust, a part of her was ashamed that she would kneel in wait for Phelps to abuse her whilst another part was grateful that the man used only her mouth and not her body. Maybe there was some chance that she would find Michael with some of her virtue, if not her innocence, intact. Phelps was already unbuckled when he rounded the corner. As he stood grinning widely at her, his cock already standing to attention. He stroked it like some kind of pet as he watched her kneeling on the floor, waiting for him. Phelps swayed with the motion of the ship, only when the ship levelled out once more did he close the distance. The man waved his cock towards her lips and Caitlin resignedly shuffled forward on knees until it touched her on her lips. Looking up at him she stuck out her tongue and began to lap at it. Small short movements, from base to bulbous tip until the Phelps was panting. He braced himself, each hand gripping a shelf on either side of them to steady himself as the 'boy' worked on him. Only days into their 'arrangement' and he suckled like a prized whore. He had thought he would have to wait for the Indies before he got such a good mouth. Caitlin began to suckle the bulbous head, she licked the drop of moisture that had formed. She was hopeful that this would not take long. Wrapping her tongue around him she began the rhythm that he had taught her. She blanked her mind to the taste and feel of him, the only good thing to have come from her attentions was that the mans cock was cleaner than ever before. She ignored the coarse promises the fell from his mouth. Caitlin could only think about the rhythm, the one that made him grunt and spew his seed as quickly as possible. Phelps had a death grip on her neck. He was close to fulfilment. Then the ship lurched dramatically, pitching them both with it. Caitlin bumped her head on a barrel of rum. She felt Phelps try and shove his cock back into her mouth but she was at the wrong angle now. His cock shoved hard into her cheek. He cried out loudly making her look up at him. She barely saw the fist before it struck her. Caitlin was thrown backwards, her hands rising to her jaw. Phelps was shouting and cursing her, his cock held in both hands. She held her breath as she watched a thin trickle of blood slip down one hairy thigh. Caitlin backed away form him shaking her head. "I'm sorry sir," She cried in terror, "It was an accident. I didn't mean to..." Fat tears spilled down her cheeks. "You stupid little bastard." Phelps roared. He lunged forwards and grabbed her. Dragging her from the corner as though she weighed nothing at all. Caitlin cried and begged and pleaded but he merely continued dragging her from between the shelves. There was a thump on door and someone called out from behind it. "You alright in there?" "Piss off will ya." Phelps roared. He flipped the key in the lock and gave Caitlin an evil smile. "I warned you what you would get if you used your teeth on me." Caitlin tried to protest but a slap caught her on the cheek. Once he had unleashed his hand on her it seemed he couldn't stop. Caitlin curled into a tight ball as he laid blows onto her back and thighs, she screamed. She was vaguely aware of someone thumping at the door but she could not move to open it. She barely registered that the blows had stopped until she felt Phelps using both hands to rip at her trousers. Caitlin screamed in earnest once more. She felt the cord around her waist snap. She struggled to crawl away from him but he held her fast to the floor. Phelps gave a cry of triumph as he ripped the trousers down her legs. Using one hand to pin her down he used the other push his cock between the cheeks of her arse. The door broke open and three crew men flew into the small storage room. "Oh my God!" Somebody cried at the vision of the cook holding himself erect over the cabin boy. Strong arms pulled him off of her and someone leant over her. "That bastard should have been left ashore. You alright lad?" He asked. "Um Jim, that ain't no lad." Caitlin gave a moan of despair and passed out. She woke much later in a real bed with real sheets on it. She tried to sit up but her head spun and she felt sick. She lay still with her eyes closed until she felt the nausea roll away again. She could see darkness out of the small window and wondered how long she had slept. Caitlin noticed that the ship had returned to its usual pitch and roll, they must have run through the bad weather. Slowly Caitlin did a check of her body, it seemed there was hardly a part of her that did not ache. The worst was her back but her arms and legs felt bruised and battered. Her jaw ached like a bad tooth and she was sure it too sported a large colourful bruise. Taking a deep breath Caitlin raised herself up until she could prop herself onto the pillows. "So you're awake." Caitlin jumped at the voice she looked up to see a man sat at a desk by one of the windows. He wore breeches and an undershirt but his hair was tied neatly to his neck. He was older than her father with a thin slash of a mouth and grey hair. "I am Captain Jones and you are a stowaway." He said dropping his quill back into the ink pot and looked at her with disgust. "I never... I was, am prepared to work. I couldn't afford a ticket." Caitlin stumbled on her words, the job was made harder by the pain in her jaw. "Hmm, no doubt. But you lied didn't you? Pretended to be a lad and caught the attentions of our cook." The hard tone made Caitlin flinch. The captain raised his hand to ward off any objections she may voice. "He will be replaced as soon as we can reach land. We don't condone his sort." The captain rose from behind the desk and walked towards the bed. Caitlin thought for a moment that he would climb in with her but he merely stood beside her, watching her with an expression not dissimilar to Phelps. "You've been injured and need rest. I will be back tomorrow to check on you. We can discuss your plan to work your passage to America then." He smiled darkly at her and then turned and walked to the door. As it closed behind him she heard the snick of the lock fastening. Caitlin slept all night and much of the next day. She was roused briefly by the ships doctor. He examined her briefly but thoroughly, removing her shirt and cutting through the bandages she had used to tape down her breasts. Caitlin blushed furiously as she held her arms up to cover herself. The man raised a brow at her modesty but pronounced her fit. She was lucky to have survived Phelps at all, he told her, the last boy didn't. She was even luckier to have survived with no broken bones. Caitlin struggled back into the dirty shirt and hid beneath the covers as soon as the doctor left. An hour later two men walked through carrying a tin bath. The water sloshed over the floor and she could smell perfume rising from it. They leered at her briefly but left quickly, locking the door behind them. On the chair next to the bath sat a towel and a fresh shirt that appeared long enough to double as a night dress on Caitlin's tiny frame. She washed quickly but thoroughly, under any other circumstances she would have revelled in the perfumed water. She had nearly four weeks of dirt caked to her body. The hot water helped to ease some of bruises as well. She was dressed in the fresh shirt and hidden beneath the bedclothes once more by the time the two men came back to retrieve the tub. It was near dark when the door opened against. It was the captain; he carried a plate with a domed silver lid over it. He set it down on the desk and motioned for her to join him. Caitlin hesitated until her stomach growled loudly. She hadn't eaten in two days and she was starving. She slid from the bed and walked to the desk hesitantly, her arms crossed tightly over her chest. Captain Jones watched every move she made until she sat opposite him at the sturdy desk. As she sat he removed the lid from the plate and she smelled the mash potatoes and gravy, her mouth watering at the sight of a small lamb chop. Without waiting for permission she snatched up the silverware and began to eat. It wasn't until she had cleared the plate that she realised that the captain had moved to sit on the bed. When she looked up he was removing his hose and shoes. She blinked at him, her stomach lurching in dread. "Don't look so surprised, my dear. Did you think you could travel for free?" he gave a dry laugh. "My good doctor claims that you have been bruised but not abused. I am interested to see how you escaped Mr Phelps' attentions. How old are you my dear?" Caitlin paled. "Twenty one." She replied nervously. Very carefully she set down the knife and fork, the urge to wipe her finger across the plate to taste the last smears of gravy had dissolved. "Come on girl." Snapped the man impatiently. "The men tell me you were often alone in the store with Mr Phelps yet you bear none of the marks of his attentions and apparently your maiden head is still in tact. So how did you keep our cook entertained?" That last word was said with such disdain that Caitlin blushed deeply. "Oh come now. Don't play the innocent with me. A proper young lady does not stowaway on board ship. A lady would have a chaperone and a ticket." "Please sir. I am travelling to the man I love, we are to be married." Caitlin cried. "Then where is the ticket that he sent you?" "My father sent him away, refused his offer for me. Michael wrote to me when he reached America; he will have my letter telling him of my plans by now." Caitlin sobbed. "Well there are ways for you to work for your ticket and keep you ... virtue." The captain smiled coldly. "Now stop wasting my time." Caitlin rose from the desk, her shoulders slumped in defeat. Wordlessly she moved to kneel before the old captain. He looked down at her with a cold smug smile. He leant forward and pulled the shirt over her head and then leaned back to unfasten his breeches. The cock that sprang free was longer than that of Mr Phelps and thinner. Caitlin looked up at the captain, waiting. When he nodded hurriedly at her she shuffled forward on her knees and pressed her tongue to his erection. Her first thought was that at least his cock was clean. As she tongued her way along his length she heard the captain gasp with delight at her ministrations. She took him deep in her mouth, relieved to notice that she could still breathe even with him in her throat. The captain gasped loudly and clutched at the sheets beneath his hands. Caitlin felt a small thrill of power run through her. She closed her lips over his cock and began to work at the bobbing rhythm that would cause the mans climax. She listened to his ragged breathing and knew he would not last much longer. He startled her by pushing at her shoulders, holding her away from him. "Do not think to distract me from your body my dear, though I see now how you kept Phelps from it. You, my girl, are a born whore aren't you?" He looked down the length of her body with glee. A knock at the door made Caitlin jump and the captain curse. "Sir, pirates." Came the cry. "I will be there shortly Mr Marks." The captain called. He listened the footsteps trailing away. "Looks like you will have to distract me after all. Make it quick; you don't want to be in the hands of pirates do you?" Caitlin didn't answer, she couldn't decide between them right now. As she took his cock back into her mouth she felt his hands reach down and grip her bare breasts. She worked up her rhythm once more, pushing his cock into her throat with long slow moves. The captain pinched and tugged on her tight nipples, matching his rhythm to hers. Caitlin flushed deeply at the touch on her body, but despite her dislike of him she felt something flutter through her at the touch. She was breathing hard when his cocked twitched deeply inside her throat, her nose pressed to his belly. She thought it could be her own exertions but was not fully convinced. With only a moment to enjoy his release the captain quickly pushed her aside and dressed. "Stay here, my dear, I shall be back before long." The Makings of a High Seas Whore Ch. 03 I would like to dedicate this story to wyldrover who emailed me to ask for more Caitlin stories. I was particularly inspired when he explained that he had read previous encounters over the phone to his wife whilst working away. I truly hope this lives up to expectation for you both. * Twenty one year old Caitlin joined the SS Good Morrow disguised as cabin boy. Unfortunately she caught the eye of the ships cook from whom she was rescued but not before he had forced her to learn the art of oral sex. Her rescue brought her to the attention of the ship's captain. Caitlin narrowly escaped the loss of her virtue when they were interrupted by a pirate attack. In all her twenty one years Caitlin had never heard such sounds. It seemed that the whole world rocked from the ferocity of the battle that raged. Male screams and yells filled the air interspersed with the sound of steel on steel. For an hour Caitlin quivered beneath the blankets terrified that the door to the captain's bedchamber would be flung open and she would be discovered. The silence after the fight was unnerving. She heard the shouts of victory and then nothing for what felt like an age. She had almost worked up the courage to creep out from under the covers and listen at the door when it flew open. There was a crack of wood as the lock gave way was followed by a crash as the whole door slammed back against the wall. In stumbled three of the most dangerous looking men Caitlin had ever seen. All three had wild hair that streamed over broad shoulders. One wore a scarf tied to his scalp and his dirty yellow tresses poured out from beneath it. They all gave a cry of mirth at the sight of her in the bed with the covers pulled up to her chin. "The captain's whore!" One shouted. "Aye; an' our Cap'n will thank us greatly for her." Sniggered another. The bandana reached her first with each other man taking a place on the other two sides of the bed. She was trapped. Before she could lunge away Bandana slid his arms under the blankets and pulled her from the bed. Caitlin screamed and kicked like a devil but she could not break free. The men laughed heartily as her shirt rode up to her waist. Caitlin froze rigid which made them laugh even louder. Strong arms gripped her around the ribs and held her as though she were his jacket slung over his forearm. Unable to cause damage with her feet or fists Caitlin sagged in the vile mans clutches. She was forced to cover her face as the pirate carried her from The Good Morrow to the pirate ship. Her captor laughed at her shame as she struggled to cover her bare body and she would swear that he swung her more than necessary just to display her naked lower half. Cheers went up as he finally stopped; he swung them round in a full circle playing up to his audience. Caitlin screamed and held her knees tightly drawn together to save worse embarrassment. "The captains whore my Captain." Caitlin felt a chill run through her body. Very slowly she raised her eyes to the sight before her. The imposing figure stood with his back to her, he was dressed in full black. Shiny black leather boots covered both feet to his knees where they disappeared beneath his long black frock coat. The coat fitted his triangular torso like a glove. Tapered to his narrow waist before outlining his broadening expanse of back to hang from strong wide shoulders. Dark curls hung free to the centre of his spine, this was no gentlemanly braid or tail but his hair blew free like that of a savage. Caitlin's breath was tight in her chest with her fear as the pirate captain paced a few steps away from her and then turned. Her eyes widened in surprise as she gazed on the face of a man who could easily be a Spanish prince or some such noble. His milky coffee coloured skin taut over the high plains of his cheek bones, almond shaped eyes of the richest chocolate; the likeness even more apt since they held such a richness of colour but also the surest sharpest bitterness. He held a thin cruel mouth that was framed by the finest sliver of a moustache that bled down to a narrow pointed beard that cover only the point of his chin. "You are the whore for the captain of the SS Good Morrow?" His voice was ice over frost, the clipped precision of his words gave him away as English. Caitlin shook her vehemently. "She was dressed as she is and lying in the captains' bed Sire." Her captor gave her shake. "Take her to join Bertha." He said dismissively. Caitlin wondered with some hope if Bertha was the cook. There was a loud cheer from the watching men and her hope flickered. The pirate carried her through the throng and men reached for her and leered at her, hands pawed at her face, her breasts and her naked thighs. Caitlin screamed. She was limp with exhaustion when they finally stopped. She had struggled like a Hell cat as they travelled into the bowels of the ships. The door before her was kicked open and she saw what she recognised as the bunk room. A maze of hammocks were strung across every available bit of space. From the furthest darkest corner of the long room the came the sound of animal grunting. Caitlins entire body trembled at that unearthly sound. As she strained her ears and eyes she heard whispering and low male laughter. Caitlin writhed desperately against the arm that held her. There was no stopping her progress through the room and she sobbed anew with her fear. "Missy meet Bertha." Her captor's rough voice laughed. Caitlin looked in all the hammocks but they were empty. A slight movement from the floor caught her eyes and Caitlin peered into the dark. As her eyes adjusted to the gloom she saw a faint glow, another few steps and she could see it was the sheen of sweat on a naked back. Closer still and gasped in horror. There was a woman crouched naked on the floor, at first she looked as though she were rocking herself for some form of comfort. If she were then it was not a comfort that Caitlin would recognise. Stretched beneath her she could see long thin hairy legs stretching out from under the woman, the naked woman knelt astride a mans waist and crooned at him as she rocked her body over his. Two other men were crouched low beside them urging on one or the other of them. Sobbing silently with fear Caitlin was carried alongside the group. The woman looked up at her a grinned with wolfish delight. Caitlin cried out in shock at the sight she made. Bertha sat bare skinned astride a dirty looking thin man, his eyes were half closed and his stubbled scrawny face wore a blissful expression. He grunted and coughed with every move the woman made. It was the sight of the woman herself that terrified Caitlin, a glimpse of what new hell to befall her. Bertha was not much older than Caitlin judging from her unlined skin but there the similarities ended. The woman's dark hair hung in deeply knotted tangles around her pale face giving the impression of an ill-kept animal pelt. She grinned up at Caitlin showing a near toothless mouth, Caitlin could see a hint of tooth stubs in the back of her jaws. What shocked Caitlin most was her body; as Bertha rocked over the pirate on the floor she swung her huge heavy pendulous breasts. Those fearsome breasts rested just above the swollen mound of her heavily pregnant stomach. The two watchers turned their attentions to Caitlin. They moved towards her with hands outstretched. Caitlin cried and began to beg them to leave her alone. "Oh don't play coy honey," Bertha crooned, she ran a finger up Caitlins exposed thigh. "You'll love it down here with me, won't she boys?" Caitlin scissored her legs, trying to flee the woman's touch without lashing at her. "You'll be taking over whilst Bertha tends her bairn." Laughed the man holding her. Caitlin shook her head desperately. "No, I can't do ... that!" She cried. Bertha threw her head and roared with evil laughter. "This is only the start isn't Barney? We was only getting started." Barney stepped back from Caitlin as though he had just remembered something important. He tugged at his trousers and freed his engorged cock, grinning at Caitlin he waved it at her enjoying her disgust. He turned bodily towards the woman who had begun to buck with more vigour and offered his filthy cock to her. Bertha made a show of licking her lips at the terrified woman cackling at her terrified whimpers. The man grew impatient and gripped Bertha by hair pulling her to him. His cock slipped deftly through her gappy teeth. Caitlin widened her eyes in fear, her brief memory of Mr Phelps let her know that this woman's teeth had been knocked out so that her mouth could be fucked with no fear of sharp teeth to mar a mans experience. Bertha moaned and sighed around the thick shaft, the man below her tugged at one huge breast pulling the woman down onto all fours. Looking up at Caitlin he tightened his grip on the enormous breast and closed his mouth around the thick fat nipple. Caitlins eyes widened in horror as he began to suckle deeply at it. The man's constant swallowing letting her know that he drank milk as the pregnant whore writhed on his cock. Bertha bucked and moaned at the attention, her bare backside rising and falling as she began to bounce in earnest. The man holding her head began to rock his hips and Caitlin knew enough to know that he was shoving his cock deep into the woman's throat. Caitlin swallowed at the sight, her memory still fresh as to how it felt to have thick swollen cock shoved so deep that you could no longer breathe. Bertha, however, moaned and sighed as the two men worked at her. "Jake, are you forgetting what you came here for?" her captor called with a chuckle. The third man, a short but broad bellied man grinned. "I thought to sample the new whore." He chuckled. "Show her what she can expect, she seems like she has only been serving one sailor at a time." The man holding her chuckled at his joke. He bent his head to Caitlins ear and whispered. "You watch carefully now; you'll be next." Caitlin whimpered at his words and trembled further as the man shoved his free hand inside her shirt. His rough calloused hand grazed her skin until he cupped her breast and began to knead her soft flesh. She thought to struggle but as she moved she felt the unmistakable bruising hardness of his aroused cock press onto her bare bottom. Jake took one last lascivious look at the her before he tugged his own cock free of his pants. Hacking a cough he spat viciously into his hand and then wiped the phlegm over the bulbous head of his ready cock. Watching her closely he placed both hands on Bertha's arse cheeks. The woman pushed herself back into his hands, he gave a chuckle and held his cock to the exposed entrance to the whore's arse. Caitlin shook her head in shock, she had never even seen that tiny puckered hole before but she could not take her terrified gaze from it as the Jake split it open before her. She could not believe that something so large could push into something so very small. It seemed like a horse fitting through a keyhole to Caitlin's innocent eyes. Bertha groaned deeply. "You make sure I get mine before you fill me." She growled. The man standing before her cuffed her lightly about the head and pulled her nose to the wire haired nest at the base of his cock. Caitlin was horrified. Was this what she would become? A whore available for every man on the ship, with every hole in her body plugged with fat ripe cocks. Not just available but eager, even when her body was about to burst with the bastard child she carried. Bertha groaned deeply. Jake thrust fully into her widely stretched arse he made a show of spreading the woman's arse cheeks to show Caitlin just how widely he pierced that tiny hole. He leered at up at her as he ground himself against those soft round cheeks. He reached one hand around and began to knead at Bertha's free breast. The woman bucked and moaned at the abuse of her body. The kneading brought a trickle of milk to the puckered nipple and Caitlin watched as it trickled down the underside of the fat white breast. The man standing cried out and thrust deep into Bertha's mouth. He stood shivering and panting for a few moments before dropping to his knees in apparent exhaustion. He took in the sight of the woman still rocking, two men thrusting into her body as they fought to soothe the ache in their cocks. With her mouth free Bertha began to urge them on. "Come you bastards, make me cum on your cocks." She hissed. Barney grinned the words. "I'll make you cum you evil witch." He pushed the groping hand from her breast and used both of his to hold it up. Chuckling he opened his mouth a wide as he could and sucked in as much flesh as he could manage. Caitlin watched as he bit down, he bit and chewed and suckled until milk seeped from his jaws. The fingers that clutched Caitlins own small breast dug deeper at the sight of the wanton display. Bertha screamed, she snarled and growled so viciously that Caitlin though it was through pain but then she made out the words and was even more shocked to see that the woman was gripped in a frenzy and urging the men to take more from her body. Jake began to pull out of her abused arse far enough that Caitlin could see all but the mushroomed shaped head of his veined pulsing cock. Once almost free he plunged savagely back inside until once more he was pressed belly to spine with the woman. She tried to look away but every time she did calloused fingers would pinch sharply at her pink nipple, Caitlin began to cry in sheer hopelessness. There was a scream from Bertha, a deafening bellow, there was an answering chorus of shouts from somewhere on the higher decks. The woman bucked and shook, throwing her back head in her abandon. There was a look of such innate bliss about her features that Caitlin could not equate with the awful scene before her. The men burrowed deep inside found something exciting about it because they both grunted their approval and worked faster than ever before. First one cried out, a sign Caitlin recognised signalled the spewing of his foul tasting seed, and then the other. "And now for you." The man holding Caitlin suddenly dropped her to the floor. Caitlin screamed and began to back away. The man dropped to the floor before her and began to crawl towards her with an expression of naked lust. She held her hand out to hold him back as she scrabbled away from him. "No, please God no. I am a virgin." She screamed. Five heads turned to her in surprise. Shoving the men from her Bertha crawled towards the tiny blonde woman. Ignoring her protests the woman pushed Caitlin down, before she could struggle Caitlin felt the woman place her hand to the private folds that guarded her womanhood. She screamed as Bertha pushed one long finger inside of her. "She's right. Go tell the captain." Bertha said with amazement. "He sent her here." Caitlin's tormentor cried. "He didn't know what was on offer. Do you want him to find out there was virgin cunt aboard after the fact?" Bertha spat at the man. The man narrowed his eyes angrily at the woman and turned back to the other men. "Jake go tell the captain the news." Without protest the man ran from the room, tucking himself back into his trousers as he fled. Caitlin waited for what seemed like an eternity before she heard footsteps running back down towards them. "Captain says... take her to ... cabin." The pirate puffed and panted. There was a string of vicious curses around the room as the breathless man tugged Caitlin away from the bunk room. She was dragged stumbling back up the steps and along the innards of the large ship until the man stopped outside a large wooden door. Caitlin had no time to enjoy her reprieve; a voice called for the pair to enter. Caitlin was dragged into the room, the handsome pirate was seated at sturdy table that held a selection of maps. She stumbled towards the desk and gasped at the sound of the door closing behind her. The Makings of a High Seas Whore Ch. 04 Twenty one year old Caitlin had joined a ship's crew disguised as a cabin boy. She was attacked by the ship's cook who had a taste for the type of young man as he believed her to be and she was unwillingly initiated into the art of fellatio. Her skill saved her virginity through first the ship's cook and then the captain once she was 'rescued' from her torment. Following a pirate attack she has been taken to the Pirate Captain but only after she witnessed the heavily pregnant ship's whore enjoying her duties to the men aboard. So far it is only her maidenhead that keeps her from the bowels of the ship and sexual servitude to a ship full of pirates. * Caitlin stood before the dark pirate in only her borrowed undershirt. She was highly aware of her nakedness beneath that thin cotton. The shirt came to her knees and was no longer as white as it had once been. Her hands still shook from what she had just witnessed below decks. A picture of Bertha, the ship's whore, heavily pregnant and being fucked by no less than three men. Worse still the woman had writhed with pleasure as those men had sucked and chewed at her heavy milk laden breasts; she had revelled in the taste and feel of those men and Caitlin was terrified of the mere memory of it. She risked a glance at the pirate before her; she blushed as she realised he was leaning on his folded arms and watching her coldly. "They tell me you are still virginal." He said coldly. Caitlin nodded. "But you were found like that," He indicated her shirt and half-naked state. "How do you explain that?" He rose from his chair and studied her impatiently but Caitlin shrank back and shook her head in refusal. "Do you understand your current circumstances here? You have been brought here because it is well known that I will not avail myself of the syphilitic whores in port. Do not think I won't toss outside this door to take your chances with nearly a hundred hot-blooded sailors who are six weeks from port with only one whore to serve them all." Caitlin clutched at her stomach with both arms, gripping both her elbows with her cupped hands as all her hopes of surviving her adventures were dashed. Despite her situation she found she had run dry of tears as though her experiences over the last weeks had drained the salt from her body. With a quivering voice she told him of Mr Phelps and his threats, she blushed deeply as she confessed to the man taking his pleasure in her mouth. Then the day Phelps attacked her and she was 'rescued' into the captain's custody and having no choice but to pleasure him with her mouth also. He watched her apparently unmoved by her story. "And you expect to leave this ship with your 'innocence' intact?" Caitlin raised her large blue eyes to his. "Could I?" She breathed. He laughed. "Of course; why you only have to make it passed the sailors and jump overboard." He said sourly. "Go ahead see what happens but leave my cabin now." "What? I don't understand." Caitlin gasped. The captain stalked around to front of his desk he leant his hip on the edge and regarded her sternly with folded arms. "Understand this wench. You are here because I am in need of a whore. If you are unwilling to be that whore then I have no use for you, so go." "But my love; in America." Caitlin babbled uncomprehending. "Best get swimming." He turned his back to her. Caitlin swayed on her feet; in that instant of hopelessness she knew that she could not hope to even survive long enough to reach America alive let alone find her love. "I agree." She whispered. "To the swimming?" He turned his near black eyes on her. Caitlin shook her head. "Then tell me what it is that you agree to." He asked suspiciously. "To the ... other." Caitlin stammered. He arched one long dark brow and gave her a scornful look. "Tell me what it is that you agree to woman or I shall toss you overboard myself." "To be your whore." Caitlin muttered. To her humiliation her turned his head and placed his hand behind his ear as though he couldn't hear her words. "I agree to be your whore." She said louder. "And how are you to be a whore when you are a virgin?" The question shook Caitlin though she knew that he baited her. "Teach me." She whispered. Watching his stony gaze Caitlin shook with the fear that he might yet hand her over to his pirates. Closing her eyes in prayer she dropped to her knees. She took a deep breath and looked up at him. "Please Captain Sir, please teach me to be a whore. I want to be the best whore you ever had." Jack Baxter, the notorious Black Wolf, controlled the smile on his lips. To the woman on her knees he showed nothing but a brief tight smile. Inside he felt a fierce joy at the sight of her on her knees begging him to become his whore. When she had been brought aboard half naked with her long lean legs flailing and the swell of her breasts on display he had felt only disappointment that such a woman would be whore to the petty tyrant that captained the Good Morrow. The news that she was almost untouched made his heart and his loins soar. Having listened to her story he knew that her naivety was his blessing. "What is your name whore?" Caitlin flinched and answered him, not moving from her knees. He gave her his full title and watched her wide eyes shimmer with fear; she knew of his reputation. "Take off the shirt Cate." She froze but recovered quickly to pull the shirt over her head. Jack looked down at her naked body, he had to let out his breath slowly so as not to show his reaction. She looked up at him with a deep blush on her cheeks as his gaze roved her pale body. Her shorn hair gave her a boyish look but her body was all woman. Small high breasts swelled over narrow ribs and her gently curved belly flared into her hips which led his eye to dark blonde triangle of hair at apex of her thighs. In the coolness of the cabin those pink nipples tightened to taut nubs giving the illusion of desire. She was his whore, she knelt before him awaiting his demand and he couldn't decide just what he wanted to sample first. To buy some thinking time he casually walked around her taking in her slender back and plump buttocks as he did so. As he walked around to her face he held out his hand. She blinked up at him in confusion but laid her own small hand in his. He pulled her to her feet and led her to his bed. Caitlin lay back in the middle of the bed. Her mind so numb that she was no longer aware of her nakedness, she didn't think to cover herself up and all she could think was that she would never marry her love. The whole reason she was in this situation was because she had not wanted to be separated from Michael when her father sent him away and now he would never want her. She would be another man's whore instead of her love's wife. She chewed her lip and the pain brought her thoughts back to the room. She turned her head in time Captain Baxter pulling his shirt from his back, his long curls spilled over wide muscled shoulders. He looked nothing like either Phelps or Captain Jones, her only real experience of male bodies. She was sure she had seen heat in his eyes when he had looked at her body but she was less sure now that he was once more restored to his frosty demeanour. Taking a calming breath she smiled wanly at him; she had begged him for help and she simply had to fulfil her bargain with him. If she was to be his whore then she would be the best whore she could be; just as soon as she found out how she was to do that. He looked at her with surprise for a split second before his features shuttered down to arrogance once more. He folded his clothes ad placed them carefully onto a chair before walking towards her naked. Caitlin swallowed, she had never seen an entirely nude man before. She supposed she thought he would look like her; with the obvious differences. But his body looked nothing like her own; his was hard packed with muscle and coarsely haired; a man who had worked hard for many a year. She felt the bed shift under his weight and held her breath as he crawled up the bed towards her. As he drew himself over her body he pulled her knees wide apart; Caitlin closed her eyes in the shame of her exposure. She shivered at the feel of his breath so close to that intimate part of her. "Open your eyes." His cold commanding tone brought Caitlin's eyes open with a start. "A frigid woman has no place warming a mans bed." Caitlin stared along her body to his eyes, she let out a shaky breath and nodded her understanding. She couldn't help but continue her stare down the length of his broad torso to his rigid member. It twitched and bobbed as though her gaze were a physical touch. She darted a look at the pirates face, his expression was as neutral as ever but there was a heat to his eyes that she had glimpsed before. It spoke of the pleasure he intended to take from her. As she watched him he continued his advance towards her; she could feel the heat radiating from his skin as he moved only inches above her. She thought for a moment that he sought to kiss her mouth, she felt the weight of his gaze on her lips so strongly that she wet them with her tongue but he stopped level with her chest. His eyes dropping from her face to her breasts. Caitlin's eyes widened as she watched the heat in his eyes turn searing. She jumped even as she watched with rigid fascination when he lowered the point of his tongue to one taut peak. Unwillingly the image of Bertha and the two men suckling hard at her milk tautened breasts came to her mind not just the wide stretched jaws and dreamy expressions of the men but the reactive writhing of the woman. Caitlin gasped at the sharp tingle that shot through her flesh from that slightest of touches of his tongue on her teat. Her nipple puckered and tightened almost painfully beneath his tongue and then once more at the feel of the cool air on wet flesh. He licked her with the flat of his tongue; one long stroke that slid from her ribs to almost her shoulder. She swallowed convulsively as the action seemed to transfer the wet heat of his mouth on her breast to her centre; her breath shivered from her lips. When she looked at his eyes he regarded her with such arrogant smugness that she feared she had already done something wrong. She widened her eyes with her question. He fought to keep the smile from those cruel lips. "You like that." He stated with a hidden humour she didn't understand. "Should I not sire?" He didn't answer her and instead placed his lips around her painfully pointed teat, he drew that puckered flesh into his mouth and the sensation made her gasp in shock. Tingles of shivery heat ran from her breast to her the very centre of body where she could feel moisture gathering at her core. She was confused by the many sensations; her breast felt as though it was created for this man to feast at. With no conscious thought her hips were tilting upwards towards him as though drawn by some magnetic force. With the new angle of those hips the pirates hard length pulsed only a hairs breadth from that most intimate part of her body. She cried out as he stroked his length along her opening. When she pulled back from him he held her firm with one cupped hand on her bottom. As he gripped her his fingers kneaded at that soft rounded globe. The pirate did not move his mouth from her breast or his hand from her arse as he dipped and stroked his cock over her. Parting her sensitive folds and spreading the strange musky moisture along his solid length. Caitlin heard him make an unconscious noise in his throat, as you would when sample some new delicate morsel of food. Caitlin's breathing matched his for it harsh nature, the rising of her chest pulled at the breast in his mouth which drew yet more tremors from her. It bowed her spine with its intensity and she couldn't decide if she liked it more when she pushed up at him or when she pulled from him. She moaned low in her throat at the devious torture her body had invented for her. She felt a flash of panic as the stroking of his cock changed in nature. He began to rub that fat bulbous head in circles pressing purposefully at her opening. His hand under her hip stopped her moving but it couldn't stop her trying. She heard his breath hiss against her the wetness he had made over her breast and finally she realised that her struggles were affecting him. He drew back pulling her breast with him until the skin was a stretched almost painfully tight and as she stared in morbid fascination he dipped his hips and pushed himself inside her. The movement so sudden and swift that there was a delay in her recognising the stab of pain for what it was. Tears filled her eyes; they were not just for the pain but the loss of her virginity and the life she left behind her. As the pain ebbed she slowly became aware of the thickness of his cock as it pulsed solidly within her, just his pulse and nothing else and the feel of it seemed to coax her inner walls to tremble around him. She looked into his eyes with confusion, before she could read his expression he shoved further inside her. She screamed and pushed her whole body upwards, she had thought herself to be filled with him before. Caitlin could not bear that terrible stretching, she felt as though her hips would pop from their sockets. Before she could adjust he began to move in long slow relentless strokes. He moved his body higher above her, pinning her knees almost to her chest and she felt each stroke as though it were a punch in the stomach. She thought she would die from the pain of it, from the humiliation of him holding her so widely open as he stabbed relentlessly deep into her belly. Just when she thought she would truly die of her shame Caitlin felt the strangest sensation. Heat poured into her centre, her body began to tighten around that thick thrusting cock like fingers closing into a fist. She could feel panic rising from within as she fought to understand what was happening to her. Caitlin could still feel every inch of his solid length stretching, probing and pounding her insides and she wondered if he would tear through her if she continued to shrink around him. She gave a short cry of real fear as liquid heat poured through her belly, her walls pulsed around the thick shaft and instead of willing him to pull out it felt as though her body was trying to draw him in. That long thick cock jerked and twitched inside of her which in turn made her shudder. The pirate plunged deep and ground against her as he hissed out a long breath through his gritted teeth. Caitlin watched him as he held himself so still above her his eyes hooded and hidden from her. Slowly her breathing settled and her fear returned; what if he thought she would never be good enough to be his whore? He might still throw her to his crew, to join Bertha. He pulled away from her and rolled to his side. Caitlin lowered her aching hips from the hated position and lay silently waiting for him to send her from his bed and back to the bowels of the ship. Wiping away a tear from her cheek she finally turned towards him. A soft snore rose from him; he slept. Completely unaware or unconcerned by the torrent of emotions running through her. The Makings of a High Seas Whore Ch. 05 Caitlin has conceded her maidenhead to the pirate but now she must keep him happy or he might throw her to his crew. Caitlin barely slept. Though the 'Black Wolf' slept soundly, a huge trunk of a man. His coarse naked body pressed tightly against her slim frame. The pirate ship was a smaller vessel than The Good Morrow, it pitched and rolled with barely a breeze to be felt. She pitied the day they ran into poor weather. As the blackness of the portholes slowly changed from deepest navy to a pink tinged azure his body shifted against hers. His hip nudged her and Caitlin gasped when he swung one mighty leg between hers. Caitlin's body ached. The pain centred between her legs and deep in her belly. Biting her lip she mourned her maidenhead. Michael would turn her away. A soiled woman. She might have hidden the abuse she had suffered but no more. She could have disguised the talents learned by her tongue but she could not explain away the loss of her virginity. She had felt her body tear open as the pirate forced his cock into her body. Her throat tightened and a soft whimper escaped her lips at the memory. Not far behind that memory was the stirring of those strange sensations that had licked at her insides. The pull of his mouth on her breast, how it had caused her hips to tilt and her back to arch. The sleeping man uttered something harsh and unintelligible into her neck, his hand tightened against her ribs. Caitlin held her breath hoping that sleep would drag him under once more. Her body was stiff and sore, her arm was losing feeling trapped beneath her captor. Captor? She should think him her saviour. She would be below deck with a cock in her mouth, cunt and arse if not for the captain. A vision of Bertha flashed beneath her gritty lids. Sweaty, toothless, and rocking against two fat cocks whilst sucking another, her milky breasts being suckled and fondled with a violence Caitlin had never witnessed before. Caitlin gasped as a large hand thumped against her bare breast. Long, thick fingers found the soft flesh and squeezed. She had thought the captain's body to be a hard bed mate through the long sleepless night but suddenly she grew aware of how parts of him had been much softer than they were now. His cock, barely noticeable throughout the dark hours, pressed hot and turgid against her thigh. Caitlin's eyes sprang open. He might want to force her body open again. She wasn't ready. She ached. Deep in her belly her body throbbed, her hips felt like they had been torn from their sockets and nipples were sensitive even to the soft cotton that covered them. Caitlin knew of cocks now. She may have only just lost her virginity but she had spent weeks distracting Phelps and then Captain Smith from using her body. She felt the pirate's cock jump and twitch against her skin, like it was sentient, seeking her sore folds without its owners knowledge. Instinctively she grabbed it. Closing her fingers around its length to keep it from finding its goal. The pirate groaned and bucked against her grip, the cock was so hard that it felt it would bruise her skin if it thrust against her once more. The skin was taut, stretched so tightly over his engorgement that it was softer than any leather she had ever touched. She marvelled at how something so shockingly thick could have fit inside her body. It was larger than Phelps and his cock had choked her on occasion. The pirate's fingers squeezed painfully into her breast, Caitlin gave a testing squeeze of his cock and the fingers responded, a tightening then loosening their hold. Kneading her newly unbound breasts. His fingers were strong, they made deep furrows into her soft mound. The captain rolled further into her, pressing his thigh to her centre and rocking his hips against her hand. Caitlin's eyes bugged. He was so solidly heavy that she felt he would smother her, his knee pressed painfully against her tender folds. If she did not act soon he would find his way into her body and reawaken all the pain of the night before. With a cry of effort Caitlin shoved him away. He moved but only by an inch. His fingers tightened possessively around her breast, still asleep he grunted his displeasure. The noise stilled Caitlin. She wanted to push him away. She wanted to run, for a terrifying moment she considered swimming from the boat to escape. Caitlin whimpered. She wouldn't kid herself that it would work. She couldn't even swim. Even if she could make it past the boat full of sailors she would drown. She would die or the sailors would catch her and drag her down to the hold. She would spend the rest of her days in darkness with nothing but stinking men and hard ceaseless cocks for company. Her fingers tightened around the captain's erection. He may not be Michael. He may never love or care for her. But he was only one man. Only one cock. If she could keep him happy she would only have to pleasure one cock. Maybe not forever but for now. Now was about all she could cope with. Caitlin struggled out of his hold. She peeled his hand from her breast and rolled out from under his leg. A hand shot out and grabbed at her wrist but she evaded it, rolling to coolness of the unoccupied sheet at the edge of the cot. Her breath was tight in her chest, her heartbeat loud in her ears but she lay still wondering if he would fall back to sleep. His eyes opened. Simply snapped open and stared straight into hers. She watched confusion cloud them before they narrowed in suspicion. Caitlin licked her lips. One cock or many? She thought to herself. With a nod of decision she slowly slid down the sheet. She would think of Michael and she would do anything that she had to do to survive to see him once more. She wrapped her hand firmly around the captain's swollen cock. He lifted a brow in question, silently watching her. She blushed at her boldness but shook off her shame and slid further down the cot until her face was level with his hip. She had never swallowed a cock at such an angle before, it had always been presented to her when she was kneeling. They looked smaller that way. Less intimidating. A bead of moisture oozed onto her thumb, she watched its gelid trail fill the creases of her hand. She rolled her thumb over the hole in his shaft and heard him hiss in surprise. She glanced up, worried that she had done something wrong but he merely watched her. She held his eye and repeated the move, his long lashes fluttered against his cheek and his breath rasped. Slowly he opened his eyes once more, his mouth twitched at the corners in what might have been a smile. Still watching him closely Caitlin lowered her head and touched the seeping bulb of his cock with her tongue. It twitched mightily in her hand. She did it again, lapping more thoroughly, tasting his salt. He groaned and raised his hips. She moved with him so that he could not thrust between her lips and choke her. She rocked, touching her tongue to his hot tight skin with every forward motion, squeezing his thickness with her fist with the backward motion. She built a soft gentle rhythm. To her surprise the cock grew even more. It swelled in her hand, its pulse thickening against her grip and the pirate's breathing grew to steady rasp. Closing her eyes against him Caitlin took his cock deeper in to her mouth. Its swollen head pressing against her tongue. The captain groaned aloud. When she snuck a glance his eyes too were closed, a look akin to pain stretching his features. His hips rocked up to meet her and she closed her lips around him. Her tongue swirled the length of him. She began to suckle. His cock felt like stone in her mouth. It could not be flesh and blood. Something so hard and unyielding could never belong to a body like an arm or a leg. She traced every ridge, every vein, took him deeper until he pressed against the back of her throat. She swallowed around him. She heard a shuddering breath and glanced upward along the hard length of his body. His arms were stretched out wide, his hands curled into the sheet, dragging it free from beneath the mattress. His eyes were closed yet his face was tilted to the ceiling as though her were straining to see something between the planks. Sweat beaded his chest, rolling down the hard ridges of his stomach, his breathing was ragged as though he'd been running. Suddenly his head jerked down to stare at her, confusion tightened his eyes. Inside Caitlin smiled at her tawdry success. Holding his eye she lowered her head and dragged her lips along his swollen cock. It twitched heavily, bouncing between them. She did it again. His cock jerked. It bounced off his stomach and strained back to her lips. Caitlin licked, tiny little cat licks over the throbbing bulb. The captain hissed but he was smiling at her. He reached for her, closing his huge hand around her breast. He squeezed. It was not unpleasant. A vision of Bertha flashed behind her eyelids and she mimicked the sound the woman had made, a purring groan. The captain gasped and his whole body jerked against her. She repeated the sound and this time took his cock wholly into her mouth and sucked deeply. His calloused thumb grazed her nipple and Caitlin squirmed against him in surprise. She built a rhythm. Pushing herself up until his cock nearly popped free of her lips then sliding down until he filled her almost to her throat. As she moved her breasts swung against his hand. She became so fascinated in the feel of the weight of her flesh against his palm that only his sudden death grip on her breast alerted her to his imminent completion. Caitlin doubled her speed. With less finesse and more urgency she pumped her mouth down his cock. It filled her. His hand twisted and pulled at her tender breast. He tugged her hardened nipple between thumb and forefinger creating tiny sparks of fire in her belly. Her jaw locked tight, aching at being held open so long but she could taste the salt of his body. Smell the tang of his sweat. His breath was an engine, revving in his chest. Blindly he gripped her. She burrowed down taking him as deep as she dared. Her throat burned with the pressure. Without warning a hand gripped the back of her head. Caitlin panicked. She been choked like this before. A thick cock forced too far into her face. Cutting off her air until she thought she would die. But he didn't pull her. Didn't hold her in place so that he could force his cock into her. He tightened his fingers into her hair as he cried out. His cocked pulsed against the roof her mouth. Her tongue filled with salt. He was done. Caitlin swallowed rapidly, trying not to drown in his seed. It poured into her mouth steadily. He groaned deeply. His fingers massaging her scalp but still not hurting her. As his cock began to deflate he rocked his hips reflexively and sighed deeply. Only when she was sure he was done did Caitlin let his cock slip from her lips. The captain gave a heavy sigh. "If you ever learn to fuck as well as you suck you would be a dangerous woman." Caitlin waited until the pirate had dressed and left the cabin before she wiped her mouth with the back of her hand. The taste of a man's cum had once made her want to vomit. As she heard the door lock behind him she thought only that it might have dried on her chin. With a sigh she lay down and finally slept. It was noisy in the ship but Caitlin had been at sea for months now. Neither the shouting of the men nor the creaking of the ship disturbed her sleep. Yet she sat bolt upright at the snick of the key in the lock. The pirate captain stood in the doorway, a tense smile on his lips before he glanced over his shoulder and stepped inside. He ran a hand over his face. "Bertha had her baby." Caitlin went cold. All blood drained from her face and goose bumps prickled over every inch of skin. "And you need me for...?" "She needs tending. There's a swell up and I can't spare anyone." Caitlin let out the breath she been holding. Her body sagged like a windless sail. "I'll need clothes and I will see to her." She sagged back onto her elbows, her relief leaving her weak "Clothes?" The captain frowned at her. Caitlin waved her hand to indicate her nudity beneath the sheet. "Will you guarantee my safety if I waltz out of this cabin as I am?" She laughed at the absurdity of the idea. The pirate nodded distractedly. He jerked open the door and called out to a passing sailor. "Fetch a dress from Bertha's cabin." "And underwear." Caitlin prompted. With a hiss the captain added the extra command. "I don't have time to play maid." Caitlin had truly thought she had been called to take Bertha's place in the hold. The thought still had her limbs trembling. "I'm sure you don't have time to beat your men unconscious if I go strolling the deck in the altogether." He pursed his lips and gave an acquiescent nod. "It would be a distraction." He smiled, fully. Dimples pinched his cheeks in the most unexpected fashion. Caitlin was still staring when the sailor returned with an armful of fabrics. They were gaudy reds and golds but they rustled beautifully. The captain snatched them up from the sailor and tossed them on the bed. "Five minutes. No more." He snapped. "I'll be outside." Caitlin gave a surprised gasp. He was nervous at being alone with her as she dressed. She shook her head with confusion. He had seen her naked, watched her as she sucked his cock but couldn't sit and watch her put on her stockings. She might never understand men. It took a longer than five minutes to dress. It had been a long time since Caitlin had worn a dress much less the dozen petticoats that came with Bertha's outfit. Bertha was broader than Caitlin and shorter. The dress was ill fitting and would have caused a scandal, even at the docks, but Caitlin made as many adjustments as she could without using scissors and a needle to begin again. The bodice dipped low but the myriad of ruffles and bows added a modicum of modesty. On Bertha it would have displayed her ample breasts teasingly but on Caitlin it made her swells appears almost boyish. Even with the petticoats the dress flounced high, revealing far too much of Caitlin's borrowed boots. Caitlin had been so long out of a corset that she had to sit and wait for her head to stop spinning whence she finally tied it in place. Her heels rang out on the boards as she knocked on the cabin door. The ship was silent. Her fear of being lynched by deprived sailors was needless. She suspected that the captain had ordered the men to other side of the deck for her journey. She followed his stiff shoulders through the maze of the holds until the stopped outside a roughly hewn door. When it opened at the captain's knock Caitlin thought it must be a cupboard it was so small. Though the ship's whore probably didn't usually rate a room of her own. The elderly man that open the door was visibly relieved to see them. He pulled the door wider so they could see Bertha laid out on a tiny cot. The bed was so small that even the short woman had her knees bent to fit on the mattress. Her lids fluttered long enough that the effort seemed to exhaust her and her head rolled on the rough pillow, turning away from them. "Her fever is down but she's delirious." The sailor croaked. His voice cracked so badly that Caitlin wondered at the man's age. His scrawny frame and rough beard made him appear to be older than Methuselah but surely such an old man could never get work as a sailor. The old man shook his head sadly and gazed back at the dark skinned woman. Bertha groaned loudly and muttered something that sounded like "four armadillos and a sandwich." The captain blanched and nudged Caitlin forward. "Make her comfortable. Stitch will be outside if you need anything." Caitlin looked at him and then at Bertha. She had no idea what to do for a delirious woman with a fever. "Hot water and two rounds of bread and meat." She snapped at the old man. He nodded gratefully. "Lock the door behind you." Caitlin locked the door as soon as Stitch ran off towards the galley. She drew in a deep breath and stepped the small distance to the cot. Bertha opened one eye and groaned weakly. Biting her lip Caitlin picked up the cloth sitting in a bowl on the floor beside the cot. She gave it a squeeze and dabbed gently at Bertha's brow. The hand that swiped her away was surprisingly strong. "Get away wit' you." Bertha hissed. Caitlin took a step back nearly stumbling over the small crate at the foot of the bed. The blankets within stirred and a high whine sounded then tailed off. "You wake that baby and I'll keel haul you." Bertha sat up and scowled fiercely. "Why are you wearing my best dress?" "So I'm not naked when I play nursemaid." Caitlin snapped in response. "You are perfectly healthy aren't you?" "I just gave birth to a small whale. I'm entitled to a few days in bed." Bertha scowled indicating the crate. Caitlin peered at the bundled blankets tilting her head left then right until she finally made out the crumpled features within. After a moment she blinked in surprise. "He does have a big head." "Shame he'll only use his little one to think with." Bertha muttered, more to herself than to Caitlin. She looked up with narrowed eyes. "Well? Will you give me away?" Caitlin watched her shrewdly. "What's it worth?" "It's been a while since I worked on a woman but I guess I could give it a go." Bertha gave a tired sigh. Caitlin squeaked in shock. "Worked on a...? That is NOT what I meant." She straightened imaginary creases from her skirt as she fought against the blush that fired her cheeks. "Do you have another dress? I don't want to ruin your best one. And some... advice. And half your rations." She added hastily. Bertha smiled as if she was pleased. "You've found your feet already." She said. She nodded sharply to the shelving on the wall behind Caitlin. "Them bags up there, second one in, there's a blue dress. It belonged to a skinny bitch. Should fit you too. It's a deal. Just mention the blood when they ask, it makes their eyes cross and they won't ask any more questions. What advice?" Caitlin held up a hand, footsteps sound beyond the door. Sure enough there was a sharp knock a moment later. Caitlin opened it just enough to see Stitch gazing back at her. He thrust a bowl of steaming water at her. It slopped around and Caitlin set it down beside the bed. She was about to close the door on him when more footsteps sounded. A boy of about fifteen skidded to a stop and jerkily handed her a sack. He blushed deeply as he tried to peer around the door. Catching Caitlin's eye he ducked his head and then gave her a bowl wide enough that Caitlin had to open the door fully for it to fit. She gazed at the meat and fruit it held. Her stomach growling at the sight. The boy risked another look inside the room, blushed again and then ran off. "She'll be alright won't she?" Stuttered the old man. Caitlin smiled at his obvious concern. "She bleeding badly." She said watching the scant colour drain from his face. "I've done this before, she should pull through." She added. "Just shout if you need anything." He patted Caitlin's hand nearly the tipping the bowl from her grip. "My wife was like an animal when she had a bairn, ate everything but the plate." The memory made him smile. Caitlin felt bad for lying to him so she just smiled until he sighed wistfully and walked away. She closed the door with her hip and held it up to Bertha. The food would have been more than a week's rations when she worked for Mr Phelps. Bertha beckoned her over and snatched the bowl from her as soon as it was in reach. "Get out of my dress and then you can ask your questions." Caitlin found the dress. Having rooted through Bertha's clothes she guessed what she owned had been stolen from others. Not too surprising for a pirate's whore. Caitlin flushed at how easily she had judged the woman, after all she was no better now. A pirate's whore; and not necessarily a very good one either. The Makings of a High Seas Whore Ch. 05 Lack of teeth made eating difficult for Bertha. The woman sucked on every mouthful, noisily, until it was soft enough to swallow. Her distaste made Caitlin take her time over dressing so that she would not have to watch her as well. The bread was not so fresh but it was free of weevils. In her old job she used to sieve them from the flour each morning. The memory turned her stomach but Caitlin didn't stop eating. She sat on the floor of the tiny storeroom whilst Bertha nursed her baby. At first she had been horrified at the sight of the woman's swollen breast being suckled but like everything else in her new life Caitlin looked away and pretended it wasn't happening. It was not the worst thing that had happened to her lately. "What advice was you after?" Bertha spoke over the greedy sucking of the baby. Caitlin licked her lips, wondering at how to say the words. "My position relies on..." "You want to know how to fuck a man good?" Bertha interrupted with a chuckle. Caitlin gasped at her bawdiness but eventually nodded. "He must have fucked you. Did the Black Wolf do anything that made you purr?" She looked squarely at Caitlin. Instinct made Caitlin shake her head violently in denial. "Well you aint gonna keep him happy if you just want to be hating him and his fucking." Bertha sighed and switched the baby to the other breast. "Let me tell you that a cock in the right spot and a good tweak can give you a few minutes of sheer happiness. With all these men about that's a lot of happy." Caitlin licked her lips. "I don't understand. What is the right spot? And I don't think I want a tweak." She grimaced. Bertha rolled her eyes. "You carry on like that an' he'll drop you on the first lump of land we hit, with a fat belly and nothing to your name." She pointed to the shelf where her duffel bags sat. "Check out that dark one with the patch. There's some stuff might help." The sack was smaller than the bags holding her dresses but it was still a weight to pull from the shelf. It rattled and jangled when it hit the floor. Bertha hissed and bid her be careful. Caitlin pulled a few bottles out of the sack and peered at them in the dull lamplight. The other woman settled the baby into the makeshift crib and snatched the sack from her. She held up a jar of creamy ointment and some kind of decorated horn. Caitlin peered at it in confusion. "Take that dress off and pull that stool closer." The woman ordered. Resigned Caitlin did as she was told. She sat on the short three legged stool in her borrowed bloomers and corset. "This," Bertha held up the jar. "Will grease the path of whatever hole gets used." "Whatever? You mean...?" The older woman rolled her eyes. "Don't get prissy with me. That captain is going to fuck you whatever way he wants. And there aint no man that can resist that tight little ass hole for long. It's gonna stay tight much longer than that pussy of yours." She laughed at Caitlin's horror. "Now you grease it all up and it'll be easier. Go on." Caitlin gasped. "You mean now? But?" "You want talk or do you want to know?" Caitlin swallowed. She paused thinking it over. "For pity's sake child this is going to be a long few days." Caitlin took the jar and dipped two fingers inside. It was thick, fatty, and didn't smell too alluring. She eyed Bertha nervously before lowering her fingers to her bloomers. Bertha nodded. Closing her eyes Caitlin swiped the grease along her folds briskly. "And the other." Caitlin's eyes popped open. "Now?" "Just do it." Bertha snapped. "You need to be ready at all times. That is what you do now. You take cock in whatever way you are told. Even if you aint told, you don't want nothing going up there without a little help." Caitlin scooped some more grease, stood up and dabbed some gingerly on her bottom. She quickly sat back down again. Bertha gave a coughing chuckle. "You ever touch yourself before?" Caitlin shook her head, no. Bertha chuckled again at her vehemence. "Take this." She handed the horn to Caitlin. It wasn't quite a horn, it was shaped, slightly rounded and the carvings stood out black against the dirty grey of the material. It was a tooth, a carved whale tooth. It was shaped like an angry cock. Thick and round but not as long as a real one. Caitlin peered at the designed, her eyes rounded in dull surprise as she made them out. Carved into the tooth were drawings of fucking. A stylised woman with her legs spread wide and an arrow pointing to the shaded triangle between her stick legs. A woman on all fours with a thick pole skewering her bottom. Caitlin stopped looking. "Now stick it in." Bertha prompted. She hesitated a moment but didn't argue. She pushed the crude cock between her legs. The grease made it glide inside without effort. "Move it about." Bertha gave a tired sigh. After a few moments of Caitlin moving the tooth back and forth she rolled her eyes. "Girl if I was a man I would rather drill a hole in a bucket of rotting fish and stick my cock in that than fuck you." Caitlin stood up and placed her fists on her hips letting the carved tooth drop to the floor. "You make this sound like an art when he's just going to stick his cock in me anyway. What difference does it make?" Bertha licked her lips. "I hear that cook taught you to suck cock." She waved away Caitlin's surprise at the knowledge. "It's a ship, sailors are worse than washer women for gossip. What did you learn sucking his cock?" "That he should bathe more often." Caitlin muttered with a shudder. Bertha glared at her. "That if I did nothing he took longer." "Why was that?" "Because it was more pleasurable." Caitlin said miserably. She glared defiantly. "Though he liked it almost as much if I cried." Bertha nodded her acceptance. "Do you know what is more pleasurable than a woman's skill? Her enjoyment. Her participation." She didn't bother to wait for Caitlin's response and waved at the many duffel bags lining the shelves. "Do you know what happens when they finally dump me ashore? I shall have another life, that's what. I have clothes and enough money to buy a small house. I have those because I make these men happy. They fight each other to make me cum." Caitlin sagged at the comparison. She thought of the pirate captain when he left her bed that morning. 'If you could fuck as well as you suck..." She blew out a determined breath and retrieved the gaudy cock from the floor. "I don't expect to enjoy it but I should at least learn to pretend." The Makings of a High Seas Whore Ch. 06 Bertha likes her job. She tries to train Caitlin but can you teach a woman to enjoy life as a whore? Caitlin awoke sore and disorientated the next morning. Stitch came to collect Bertha's dressings and sheets and to deliver another mound of food. He warned them that there was another ship ahead and that they would be boarding it within the hour. Bertha made Caitlin take the cock once more. Though her body ached from her 'practice' the day before she dutifully picked it up. The day before she had learned to move her hips and to sigh with feigned excitement but she'd felt nothing. Without complaining she dabbed the grease on her tender parts. She sat on the stool and pressed the cock to her nether lips. Bertha groaned. "You'd never get a bed in a house of mine." Caitlin thought to tell the woman she wouldn't want a bed in a whore house but stilled her tongue. "What should I do?" "Put down the cock. Touch yourself." Caitlin gaped. The order seemed even more humiliating than ever. She sat frozen, just watching the other woman. She set aside the carved tooth and reluctantly rubbed her slit with her fingers. "You're fucking it not wiping it." Bertha barked. "Damn it, I think I'd rather go back to work." She swung her legs over the side of the cot and groaned at her aches and pains. She crooked her hand and beckoned Caitlin closer, pointing at the stool when she merely shuffled forward. Bertha made her sit down in her underwear on the stool, much as she had done the day before. This time Bertha dipped her fingers deep into the jar and motioned Caitlin to open her legs. "When a woman is ripe for fucking she gets wet." She slathered the ointment along Caitlin's slit making her jump and squeak in surprise. "It feels much like the lotion and most men won't tell the difference. But when she's wanting, she moves different. She squirms and writhes, you need to know how that feels even if you only intend to pretend." Caitlin gripped the edge of the stool as Bertha stroked along her folds with her strong greased fingers. Two fingers parted her folds and settled on the tiny button at the very tip of her core. Fire sparked at her touch. Caitlin gasped and tried to wriggle away. Bertha nodded. She repeated the move and again, something prickled within Caitlin's belly. It was shocking, fleeting and a little uncomfortable. But not horrible. "Stop fighting it you silly cow." Bertha hissed at her. This time Caitlin made herself sit still. It was not easy. Bertha's fingers ran up and down her slit, distributing the oil and slicking her folds. As she slowly got used to being touched Caitlin started to relax. The fingers slid up, brushing against her nub but not pressing it, then back down, tracing her opening but not entering. After a short while this started to irritate. Caitlin tilted her hips trying to nudge Bertha's finger against her nub once more, the other woman chuckled. "Now that is how you move when you want it." She murmured. This time her finger traced around Caitlin's nub, stroking it more firmly, laying her finger along it and gently rubbing. Caitlin trembled, something deep in her belly clenched. More immediately her body bucked under Bertha touch. The centre of body seemed to heat, her legs shivered with the effort of raising up to meet the touch. She gasped when Bertha slid one finger inside her. It felt good but she wanted more. Her body felt empty, and... itchy. Like she needed something inside her to scratch that tickle. The pressure on her nub made her ears throb. Blood pumped hard, her breath caught in her throat, when Bertha stroked her and missed that extra sensitive spot she moaned with disappointment. Bertha chuckled and dug her thumb over the spot. Sparks lit behind Caitlin's eyes. Her hips bucked, desperate to feel more. Her muscles clenched against Bertha's finger, trying to hold it in place. Bertha murmured to her but she couldn't hear the words over the ringing in her ears. Her body grew tighter and tighter, she was almost standing, she'd leant so far into the woman's touch. Heat bloomed, sweat licked her skin. Every part of her body was hot. She felt weak. Her limbs trembled. Still the fire grew. She worried that she would just burn until she ignited. Then Bertha sat back. Caitlin cried out in shock. Bertha waved her protests away. "You're close, now you finish it." Caitlin sat for a moment. Her skin cooling, between her legs she still tingled. Slowly, almost suspiciously she slid her hand between her thighs and touched. She jumped at her own contact. Her skin was oiled and warm. Liquid coated her fingers. The tingles returned. She slid her fingers along her slit, exploring. She gasped when they brushed her nub. She lingered there, feeling her body tighten. Her hips lifted. Encouraged she rubbed harder, worrying the tiny button between two fingers. Her breath caught in her throat. She risked a glance at Bertha. Like she needed to confirm she was doing it right. Her chest tightened. It felt like panic but the slow burn between her legs didn't feel scary. Something good was nearby. Just out of reach. She rubbed all four fingers along her folds. Wanting, needing something more. She was almost lifting off the stool now. Her heels dug into the floor, her palm pressed to the seat to stop from falling over entirely. Her body jerked in shock when Bertha cupped her breast through her chemise. Her nipples were tiny rocks and even the lightest touch magnified the fire inside her. Tiny strings ran down her body from her teats to her belly. Every brush, every little rub of a thumb caused her body scrunch inwardly. She shook with effort. But still nothing more happened. "Is that it?" Caitlin hissed angrily. "Lots of tingles and emptiness." Bertha laughed, throwing her head back. "No, child. That is not it. That is the beginning. Turn around and start again." She guided Caitlin into position. Bending over the stool with her backside facing the other woman. Confused she began to rub her fingers along her folds once more. She slid her fingers inside just to fill her body. It felt good but it was not enough. She tried two fingers and then three, but it still wasn't right. She went back to pressing her index finger to her button and was rewarded by hot licks of flame in her belly. She worked it some more. Something cool touched her slit but she was too lost in sensation to think what. The coolness pushed inside her. The tooth. It slid in easily. It touched her more deeply than her fingers and Caitlin sighed. Her body clenched. Bertha pushed more firmly. She pushed it as deep as it would go and Caitlin growled with relief. Her hips rocked and it made her whole body shudder. This was what Bertha had meant by little moments of happiness. Her whole world froze to that moment of time. Bertha started to rock the tooth, like the Captain had with his cock. Only this time with every stroke Caitlin's eye fluttered. Her insides gripped so tight that it hurt, but it still wasn't enough. She rubbed furiously at her button of flesh. Each press drew more and more sparks. She could taste her pulse on her tongue. Her ears rang. Her hips matched the rhythm that Bertha set. Suddenly everything changed. Bertha pulled the cock free. Caitlin, still rubbing her swollen nub, tilted to try and look at her. With a hand on her spine Bertha pushed the cock in deep and held it there. Then withdrew. And entered once more. Caitlin gasped. Her body responded with a ferocity untold before. Her body had tightened and tightened and finally it snapped. Pulse after pulse rocked her body. Her eyes rolled back into her head as her body trembled in pure pleasure. She stood, bent double gasping for air when Bertha leaned against her and chuckled. "You want to know the best thing? You can do that over and over again, not just once like a man does." Exhaustion sent Caitlin to sleep. When she woke Bertha was nursing and there were sounds of fighting above deck. Small pops and cries sounded. The pirates were taking another ship. Caitlin stretched out, her body ached deeply. This time she had to smile at the cause. Her body had bucked with sheer, delirious pleasure. "He'll be coming for you after this." Bertha said nodding to the ceiling. "They're always hard and hot after the fight." "But I need to tend you." Caitlin sighed. "After all, there's just so much blood." She grinned at the other woman. Bertha shook her head. "I'm not dead. You'll be in the captain's bed before supper." She gazed wistfully at the ceiling. "I'm going to miss all the spoils this time." "You sound disappointed." Caitlin reached for a lump of bread. Bertha shrugged, rousing the bairn to another hearty suckle. "It's just business. The boys snatch up all manner of stuff thinking to outbid each other for first dibs on a fuck. Without me they'll lose it all to cards and fighting." "What if they lose?" Caitlin said, the thought only just occurring to her. Bertha shrugged as if the question was nonsense. "The Black Wolf lose a ship? Never." Caitlin paid more heed to the noises now, almost wishing that she could see what was happening. Sure enough only a few hours later there was an impatient knock on the door. Mumbling apologies Stitch announced that he was to escort Caitlin to the captain's quarters. Biting her lip Caitlin gathered up the small sack that Bertha had put together for her and with a deep breath she stepped in the hold. For an old man Stitch walked briskly. He pressed his hand to her back and hurried her through throng. Several men lay on the floor, bloodied and groaning. Some took turns bandaging each other. Hands, arms, faces; the fight had taken its toll. Other were laughing, jingling coins and various knick-knacks. Candlesticks, silverware, some jewels. Barrels were being tied down, apparently the other ship had lost its stores in the battle. The scent of sweat and blood filled the cramped space. Though they looked at her hungrily nobody molested her progress. It was a relief to get to the deck. The wind blew the stench of below decks from her nose. Caitlin scanned the horizon and gasped as she saw the burning sails of the other ship. Though they were already a distance away Caitlin could see men running back and forth, probably with buckets. Without sails they would never catch the pirate ship. The plight of the other ship was already lost to her thoughts as Stitch hurried her along the deck. Before she was ready he stood at the captain's door and was raising his fist to knock. She didn't know what to expect but she nearly dropped her bag when the captain leered through the crack in the door. His eye was blackened, blood dripped from a cut near his brow, dirt and smoke covered the rest of him. He took her arm and all but dragged her inside the chamber with barely an acknowledgement of her escort. Even behind the locked door Caitlin could hear the cackles and catcalls from the men outside. All offering to service Caitlin if the captain were unable. Almost before the locked clicked into place Caitlin was shoved hard against the wall. The captain kicked her ankle aside and nudged his leg between hers. His face burrowed into her neck. "Your wounds needs tending." She said weakly. "The only part of me you need tend is my cock." He growled, licking a long wet line down her neck. His hand fumbled her breast, shoving her harder against the wall as his fingers dug deep into the soft flesh. "You'll fuck and then you'll suck it hard so you can fuck it some more." Caitlin swallowed hard. His hand was rough and impatient, she heard the fabric rent as he sought to bare her flesh. "Don't rip it!" She cried in alarm. "It's all I have." The pirate leaned back from her, with his cuts and bruises his leer was a terrifying thing. He jerked his head to a pile of fabric near his desk. "I've a dozen to replace it. Perhaps I'll rip those from your tits too." He gave a growl and dragged at the fabric separating him from his quest. Buttons popped and spilled to the floor, they rolled and clattered across the boards. He gave a sigh as her small rosy nipple was exposed. Without pause he bent his head and suckled loudly. Wetly rasping, dragging her flesh deep between his teeth. Caitlin gasped at the suddenness of the onslaught. As he suckled he further rent her new gown. Dragging first the sleeves and then the bodice away, tossing them behind him, kicking her skirts when they dropped, and hissing at the barrier of her petticoat until finally she stood in her corset and bloomers. Most of her chemise lost to his haste. It hung loose over one breast and absent from the other. Caitlin could do nothing more than try and keep upright as he sucked and chewed at her. His knee nudged her legs wider apart and suddenly his fingers were searching her drawers. He growled as he brushed the soft hairs between her legs, grunted as he forced two fingers in deep. Caitlin gasped in shock at the sudden intrusion. She had greased her parts in readiness so his entry was smooth, his fingers thicker than either hers or Berthas. The fullness reminded her body of the pleasure she had felt the day before. Her hips bucked against his hand. The captain paused a moment, feeling her nudging his palm. Then he delved deeper, rubbing his palm over her nub, doubling his efforts when she groaned in response. Caitlin's body responded as it had done yesterday. Her belly tightened, her hips tilted and her breath grew shallow in the confines of her corset. She could hear each slick pump of his fingers into her body. She thought she might have used too much lotion before she understood that this was her body enjoying his attention. Bertha had said a woman grew wet when excited, this must be what she had meant. Tingles lit a path from her nub to deep in her gut, her legs grew weak holding her up, and her covered breast ached to be suckled like the other. She arched her back in offering. The captain hissed and took a deep bite of swollen teat. When she cried out in pain he eased back and suckled more gently. With a growl of impatience he stepped back, put an arm around her waist and lifted her of her feet. Caitlin shrieked her surprise. "I'll be gentle next time." He snarled, tossing her to the bed. Caitlin barely had time to work out which way was up when he grabbed her again. Rolling her on to her stomach and then lifting her bottom high. When he finally set her feet on the floor he pushed her knees as far apart as they would go. Looking over her shoulder at in him in trepidation Caitlin watched him stand there just looking at her. She had a moment to think that he may not like what he saw when he began tugging at his clothing. He cursed and hissed until finally he pulled his cock free of its confines. Then he met her eyes. They were glazed, as if fevered, and all the while he looked at her his fingers handled his cock. Stroking it to shocking fullness. Caitlin thought back to the carved tooth Bertha had used on her, remembered the pleasure it had delivered when thrust into her body, and her only thought was that it had been so much smaller than the monster that reared at her now. There was little time to think of it. One moment he was staring at her exposed body the next he fisted his cock and ploughed it between her thighs. Caitlin gave a gasp. Her body suddenly filled. Stretched. She panicked thinking that he would burst through her parts and out through her belly. He paused. His cock buried deep. His stomach pressed to her bottom. His fingers held her hips in place. Only their breathing filled the room. Outside, on deck, the men called to each other and worked the ship. Inside there was only the panting of their breath and stretch of her body around his. He held true for a long moment. She could feel his pulse inside her. The thud of his heart deep in her gut. Then he ground down. Stretching her further, making her squirm to find some ease from his size. Then he pulled back and the discomfort dissipated. But her traitorous body leaned back to find him and he thrust deep once more. Caitlin moaned at the predicament. It hurt when he thrust deep but when he withdrew her body quivered to be filled again. Tingles grew to be tremors. Caitlin gave in to the predicament entirely. She rocked back, skewering her body on his, feeling every ridge stroking her tightly clenched muscles. His cock jerked and flexed like a snake deep in her belly. Jack stood mesmerised by his virgin whore. Her cunt was split wide open by his cock. He had thought he was at full mast when she'd writhed on his fingers. Watching her rock back against his cock, leaving a shiny trail of juice as she moved. Through the split in her bloomers he watched the curve of her arse flex, they eye of her backside clench, and the fabric of her underclothes sticking to her wetness. Even though his eye was still swelling and it hurt to keep it open he didn't stop watching. Over and over she rocked, her eyes glazed and unfocused, her cunt tightening painfully around his throbbing cock. It hurt to be buried deep inside her, like someone had closed his cock in a vice. Yet he couldn't stop watching how that tight cunt suckled his cock. Her moves grew shallower, faster. Her breathing changed, Jack found he was holding his breath waiting to see what she would do. His balls ached with the need for release. When he stepped on board he'd had her brought to his cabin for the sole purpose of fucking her. Of ripping her damned clothes off. Of jamming cock into her body until his balls caught fire. Yet here he was. His cock half buried in white hot, slippery cunt. His rod stiffened and twitched. He could bear no more. Jack gripped her hips tightly. When she moved to ride back up his cock he held her still. With slow deliberation he pulled back until the mushroomed head of his hardened member began to pop free of her body. He held it there, the widest part of his cock stretching her opening. He could see her cunt lips flexing, suckling him, and trying to pull him back inside. With a grunt of impatience Jack rammed his cock all the way inside. Shoving past her tightly drawn muscles, all the way to the end of her opening. Then he pushed some more. Grinding against her plump bottom. She gasped, hissed through her teeth. It was not what she wanted but it was just what he needed. He pulled all the way out again. His blood thickened pole popping free of her hole before he forced it all the way down again. He did that once more just to feel the whole length of her wet cunt stretching around him. He grew fascinated at watching the head of his cock force open her lips as he pulled almost free before slamming to the end of her body. He'd never fucked anything so tight in his life. He licked his lips wondering how it would feel to fuck her arse. Another time. Jack slammed home. The force knocked the air from her lungs. She whimpered. His cock burned at that small helpless sound. His eyes grew bleary. He bucked deep. Ground his hips to her arse. Watched her fingers make fists into the blankets. His balls clenched. He grunted in pain. He bucked, grinding her against the softness of her bottom. He pulled back. Only halfway. His cock trembled. He slammed it home. His eyes nearly rolled back in his head. He could feel the muscles moving in her legs as she tried to pull away and it inflamed him further. Lost in the feel of her body he slammed again and again until finally his balls erupted. He ground down into her. Forcing his cock ever deeper into her cunt. Over and again his cock spewed seed into her belly. It pumped and pumped like he had never cum before. He held tight, felt her quiver and shake beneath him. He knew it was not from pleasure but in that moment he was beyond caring. Jack did not let go his hold on her hips until his cock finally softened inside her. His entire body felt numb, spent. Even then he stood, his fingers still running grooves into her hips, and he watched his thick viscous juices sliding from her body. He smiled territorially at the sight. The Makings of a High Seas Whore Ch. 06 "And what are you looking so bloody pleased at?" Jack blinked hard. He looked about the room, left and then right before looking down at his virgin whore. Her eyes were narrowed, her lips a thin line above a jutting chin. He shook his head trying to recover the image of his helpless whore-in-training. Quick as a whip she rolled on her back. He was too slow to move out her way as she reared up and slammed the heel of her hand to his chest. The blow was unexpected and he hadn't braced for it. That was the reason he went careening backwards. It would only have been a step or two had it not been for his breeches about his knees. He landed, bare arsed on the floor. "If you could fuck as good as you suck you said. I'd be a dangerous woman, you said." She all but growled at him. She stood over him, bare feet braced wide apart, wearing only her corset and bloomers. Jack was mesmerised by the sight of the sodden, cum-soaked fabric, made translucent across her pale golden triangle of hair. He licked his lips, his cock stirring again. Apparently it was not the reaction she wanted because she jabbed him in the chest with her pointed finger. He recoiled. "Well if this is as good as you fuck then I'd be better off out there." Jack opened his mouth to retort but his mind, like his balls, was totally empty. His teeth clicked as he closed his mouth. "YOU ARE MY WHORE!" He bellowed finally. "WAS!" She yelled back, her fists on her hips. "I've more chance of enjoying a cock out there. They might have enough gratitude to wait for a woman to finish before pounding on her like a battering ram. You might as well have been fucking your fist." She looked like she had more to say but, instead, she merely clenched her fists and made a growl deep in her chest. She stepped over him and stomped to the door. "Stop right there." He ordered. "Or you'll what?" She snapped. "Throw me to the evil pirates out there? Too late." Jack rolled to his feet and stumbled. With a frustrated hiss he dragged his breeches off entirely and chased after her. He reached the door at the same time she did. When she dragged it open he threw his palm against it, slamming it shut. She pulled with all her might but he was stronger. He could hear the catcalls of his men, offering to take over his woman. He growled in his most intimidating way. Caitlin paused, looked him all the down and then up again. Apparently unimpressed she pulled uselessly on the door again. "Just what is wrong with you?" He gave a tired sigh. Only moments ago he'd been lost in a fog of sexual euphoria, now he was facing down a mad, and slightly alarming, woman. Caitlin blew out a breath and sagged against the door. "I came here determined to be a good little whore. I didn't fight you when you touched me, actually I liked it. All that practice with Bertha and, what do you know? I was right. You don't want someone wet and willing, who might enjoy have your mighty cock wedged into places it doesn't fit. You want a receptacle. A cup or a bottle could do the job you want. It's not worth the effort." Jack choked on his words. His cheeks flamed like a boy caught playing with himself by his mother. He was shamed like he'd never been before. Apologies tripped over his tongue so quickly he slapped his hand to his mouth to hold them back. Then his eyes bugged as he fully absorbed her words. "Practice? With Bertha?" The images in his head were so startling that he let up his hold on the door. Caitlin grabbed it and he had to slam his shoulder to it before his men caught sight of her. "You know half those men have syphilis." Caitlin shrugged. "I was that close." She narrowed her eyes to slits and held up her thumb and forefinger, squeezing them together. "That bastard buggery close to taking pleasure in your cock." She snarled wordlessly again. "If that's what it means to be your damned whore then bollocks to it. I got used to one cock, I'll get used to three. At least then I'll get some nice clothes and some money to my name." Jack gaped at her. Unable to connect this bad-mouthed harpy to the whimpering virgin who'd laid rigid beneath him only the other night. For a whimpering virgin she'd sucked him good the next morning, he remembered. "They fucked your damn mouth just to keep you quiet is my guess." He said sullenly. "Well at least I wasn't disappointed." She retorted sharply. He laughed. Unable to stop himself, he threw back his head and laughed out loud at her cheek. He shook his head in bewilderment. "You are my whore." "Deal's off." She folded her arms across her bare breast and slumped her back to the door. He laughed again, surprised. He slid back the large bolt across the door and took her elbow, brooking no resistance he led her back to the bed. "You want to renegotiate?" "No." She sighed sulkily. "I want to leave." She nodded to the door. Jack rolled his tongue along his teeth and eyed her warily. He'd interrupted her pleasure, he knew that. He'd been damned turned on by her taking some pleasure in something he thought she'd never enjoy. Watching her body rock against his cock had driven him to the brink of his control. He shouldn't feel bad for fucking his whore. Conflicted, he folded his arms stubbornly. If she left the cabin she'd have the syph by the time he'd reach the door. Then he would never get to fuck her again. Something in his gut curdled at that thought. But she was his whore! The other part of him declared. He was entitled to fuck her any which way he chose. Arse, cunt, hard or soft. He held up a hand. Not just to keep her quiet but his inner turmoil too. Taking her by the elbow he led her back to the bed. Holding his hand up for silence once more he stepped over to the heap of frills and lace dumped at the foot of the cot. "Dresses." He snapped. He picked up a handful of fabric, and then another. He stalked back to her and dropped it at her feet. He stepped back and picked up another handful of frothiness. "Underwear and stockings." He stalked back and lifted a purse from the floor. "Gold." He dropped coins in a shower over her head. "You want payment? There." Caitlin jumped as the cold coins hit her skin but she remained, arms folded and mutinous. Jack grew aware that he was standing before her with his cock hanging out, arguing prices. He chewed the inside of his lip. "You'd rather go out there and get fucked by twenty sailors than stay here with me?" She looked him up and down blandly. "Really?" "If that is the best that you can do then yes." She pouted and turned away from him. He closed his mouth before he could challenge her to prove it. "A full share of the spoils." He said abruptly. After a full minute's silence he sighed his frustration. "And I will be more considerate of your pleasure." He ground out, wondering why he didn't throw her to sharks and have done with it. Finally she turned and looked at him. He could not fathom how she could look so haughty in her torn chemise, corset and bloomers. He tried not to stare at her one exposed breast, the nipple drawn tight in the cool cabin. Quickly he raised his eyes to her face. She noticed. She nudged a pool of fabric with her toe, eyeing the pearls and beads adorning the bodice and her eyes softened. He hadn't realised he had been holding his breath until she quietly said, "Deal." Jack grinned, his face stretched wide in triumph. He frowned a moment wondering how he had bargained away a full share of spoils for something he'd had for nothing only the day before but he shrugged it off. Instead he reached out for that tightly budded nipple and felt it pucker under his thumb. She didn't pull away. He stepped closer, his gut as tense as when he'd stepped aboard ship only a few hours ago. Braced for a fight. He paused, considering. He was distracted by the soft fullness of her bare breast. I sat perfectly in his palm, the hardening centre nudging for attention. He circled his thumb around it, it grew harder still, begging for a squeeze. He pinched it between his fingers, watching it grow, the nipple distending whilst the skin around puckered so tightly as to disappear. He could feel his cock grow with fresh vigour. His hand curled around the breast, he tightened his grip and watched the soft creamy flesh spill out between his fingers. Caitlin arched her back, pressing the hard bud of nipple to his palm and he growled in response. Her head dropped back, her eyes closed and lips parted. He was fascinated. She was enjoying his touch. He pinched her offered nipple, tugged it, watched it stretch and listened at the soft gasp that she issued as he did so. A woman suffered through a man's pleasure. She cried and whimpered for help or she bore it with experienced weariness. Jack grabbed the remaining chemise and dragged it free of the corset. The fine fabric shredded noisily. Caitlin issued a gasp of surprise that dissolved into a soft moan as he caught hold of her other breast. He stood before her, a breast in each hand, the heels of his thumbs working the sharp little points as he weighed and pummelled the soft delicious flesh. Her back arched further, offering him more, he took it. He pressed the soft mounds flat just to feel them bounce back as he let go. He tugged the hardened nubs, watched them stretch until Caitlin gave a soft hiss, he let them go and rubbed them gently until she moaned once more. He liked the sounds she made. He squeezed and pinched some more. To his surprise Caitlin opened her legs and tugged him closer. He nearly stumbled in his haste to close the distance. His cock was at full mast once more. It jutted just below her chin and he'd a thought to slide it into her mouth. But her head was tilted back, her eyes closed as she offered her breasts to his busy hands. His teeth ached, wanting to bite down into her flesh. So he took his cock in his hand and rubbed it against once diamond tipped teat. Watched his stickiness coat the puckered nub. Caitlin gasped at the new pressure on her body and rolled against him. Fascinated he rubbed it again and then again, felt the soft weight of her breast give way to the hard length of his cock. The tit jiggled deliciously under the impact. A soft shimmy. He dropped to his knees between hers. His face level with her breasts. He leaned towards the one not coated in his cock juice and licked it. There was no taste to discover but the response inflamed him. Caitlin lifted her hands from the tangles she'd made in the sheet to cup his head. She held him at her breast whilst he suckled like a hungry bairn. His licked smacked noisily as he broke the pressure he'd built up. Caitlin held tight, her fingers tangled in his long hair, her hips rolled until her centre bumped the hand that held his cock. He thought to slam it all the way home, to bury it in that tight wet hole, the memory so sweet that his fist tightened around his cock. He paused. Consideration, he'd just made a bargain for consideration, damn it. Taking a steadying breath Jack released his cock. His fingers were wet with its juices, he would shoot his load in a moment if he didn't hold back. Gritting his teeth against the idea of consideration he began to lap at her breast once more. Consideration, he grumbled to himself. He slid two fingers down her corset ties until he reached the damp edges of her bloomers. Damn but she was wet. He pushed two fingers against her slit and nearly jumped at the gasp she let out. He'd thought for a moment it was a complaint, tetchily he snapped a look at her, pulling free from her death grip on his hair. But her face was soft and dreamy, her lower lip caught between her teeth. He swallowed hard. Rocking his fingers in and out of her body made her cry out. Her fingers dropped to his shoulders and dug in, as though she feared she would fall. He wanted to jam his cock in her cunt and pump till he was emptied once more. Jack growled with frustration. He altered the angle of his hand so that he slid along the hard button at the apex of her slit. In reward her hips tilted in greeting, allowing him to slide deeper. He built a rhythm. Long and slow, running the length of her slit before plunging deeply into her cunt. His fingers dripped with her fluids. He'd never felt a woman that wet before. She began to shake. Her moans grew loud enough for the men on deck to hear. She lifted her feet from the floor, lay them flat on his thighs and then pushed. She lifted bodily until she matched his rhythm raising up when he pressed down and rocking away as he withdrew. She was fucking him. She hissed with annoyance as his rhythm faltered. Jack doubled his efforts, fascinated in just what might happen. She rocked with a fervour that he recognised. Her body tightened around his fingers. She moaned deeply and lifted her feet from his thighs to his shoulders. Jack was lost. She lay back on the cot, her soaking wet cunt inches from his face. He'd never witnessed such a wanton woman in his life. His cock ached just watching her. Tension tore at his shoulders. He was sure she was only a hairsbreadth from completion, if a woman could achieve that, but she'd moved out of the angle that had made her moan. He could smell her musk. Her musk and his cum. Unsure what to do pulled his fingers free and buried his face in the short soft curls of her cunt. The taste of his own seed made him grimace in distaste but the way Caitlin levered upwards the moment his mouth touched her body tore the thought from his mind. He found the nub of her cunt with his lips and suckled. She screamed. Her legs clamped about his head. Holding him tight in place. Barely able to breath Jack sucked and nibbled. The woman arched like a bowstring, grinding her body to his face. Fists banged on the cabin door. Lewd comments were shouted. Jack ignored them all. Caitlin whimpered and sobbed but her tension didn't ease. The woman was frenzied. Unsure of what else to do Jack pulled free of her legs and thrust three fingers deep into her cunt. With his thumb he pressed the hooded button standing proud of her folds. Caitlin wrapped her legs about his waist, her fingers made fists in the sheet. Her body was stretched so taut that she barely made contact with the bed. Her cunt was so filled with the captain's fingers whilst his thumb worked tight little circles on her nub, yet her body just grew more and more tense. She opened her eyes to see him watching her. It was not a horrified look, not confused, just a fevered excitement. As though they were both racing from the same thing. His face was shiny with her juices. His eyes alit with baffled excitement. And she was his whore. This man working furiously for her pleasure. She gave a shocked burst of laughter. And then her body ignited. Something deep within her snapped and heat and pleasure spilled out. Centring on her cunt but spreading outwards to encompass all of her. Her entire body shook with wave after wave of mind numbing pleasure. She rocked against his hand milking every last drop of sensation from him. Several long minutes passed before she could focus clearly. Even then her body still trembled with delicious aftershocks. "Holy shit." Hissed Jack, making her laugh. "Consideration." She said on sigh. Her eyes were heavy, she felt like her limbs were under water, they were so hard to move. Even so she reached between their bodies and took a hold of his bobbing cock. The tip dripped with juice, she rubbed it into the smooth skin of his swollen tip and tugged him closer. She thought that fucking was the last thing she would want to do but as his engorged cock pressed into her body all the pleasure returned. Every nerve ending was alit with awareness and his engorged member stroked each one. She pulled him closer. His cock filled her. Though her body still stretched to accommodate him the sensations it evoked were so intoxicating that when it was fully home she ground against him to take yet more. Jack's eyes nearly rolled to the back of his head. Her body held his cock so tightly that it hurt. Yet along the length of his cock he felt her muscles gripping him in a rhythm that stole his breath. He wasn't even moving. Very slowly he began to rock, in a slow and considerate manner he began to gently fuck her. Caitlin growled at him and he jerked his head to question her. What now for crying out loud? He held still, confused. She twisted her hands in his shirt and dragged him against her, locking her heels together behind his back to underscore her impatience. He held still for a moment. His confusion cleared at recognising her urgency. His cock bobbed with the thrill of understanding. He pulled free of her body and slammed all the way home. He ground tightly against her, mashing his body to hers. This time she reared up to meet him. Tilting her body so that his cock slid yet deeper inside her. She held tight and milked him. His eyes rolled at the sensation. Then he was lost to the insane rhythm that she set. His thighs slapping at her skin, her ankles twined behind his hips as she levered up to take him deeper still. This time when he rammed his cock deep into her belly she didn't tense or cry out. She dragged him deeper still and circled against him until it felt like she sucked the cum from his balls. This time when his body jerked and bucked in completion hers rocked and spasmed at the same time. "A toast to consideration." Sighed the fearsome pirate, The Black Wolf. "Aye, aye, captain." Agreed his whore.