The Maings of a High Seas Whore

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.