The Makings of a High Seas Whore

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A young womans runs away into danger.
2.3k words
4.11
91.9k
36

Part 1 of the 6 part series

Updated 06/07/2023
Created 09/06/2007
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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.

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Wise_ManWise_Manover 16 years ago
Good

I look forward to reading more

AnonymousAnonymousover 16 years ago
Not bad

There is alot of crappy stories on this site, full of spelling errors, grammer problems, shitty story line and just all around badly writen. Luckily, this story will not be added to that section. Keep up the good work, I wouldnt mind reading more of this, to see what happens next.

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