Chapter Two

Caroline slept well, despite the rigours of the space in which she was confined. The next day the weather was fine and the captain was minded to indulge them all, allowing them on deck for most of the day. Several of the girls engaged in banter with members of the crew; one might have almost supposed that the girls were their companions instead of their captives. That evening Caroline was invited again to the captain’s quarters. This time he asked her to dress in a fine white negligee, embroidered with lace. The material was thin, almost gauze-like. Caroline was embarrassed to see that it did not entirely hide her body. She was sure that her nipples, which had become erect almost as soon as she entered the captain’s cabin, were visible, as was the triangle of dark hair between her thighs. But what was the point of her modesty? Here she was, the captive of a licentious and mercenary man, entirely as his disposal, and knowing that before the night was out he would once more possess her. That she would be fucked was not in doubt; all that was unresolved was the manner of it.

She had just finished arranging herself in the negligee when the captain drew back the curtain. “I remembered that I have this,” he said.

He handed her a box, inlaid with a pretty design of flowers and covered with glossy lacquer. She opened it. Inside was a range of cosmetics, in tiny compartments: eye shadow, mascara, blusher, rouge for her lips. And a tiny bottle, which when opened gave off a heady perfume of jasmine.

“It’s lovely,” she said.

“Make full use of it,” he said.

He watched while Caroline applied the contents, darkening her eyes, reddening her lips, giving colour to her cheeks. There was a pretty hairbrush too, the back decorated in mother-of-pearl. She brushed her blonde locks, then let them fall to her shoulders.

“What became of the previous owner?” she asked, a little mischievously.

“Are you sure you want to know?”

“I would not have asked otherwise.”

“I took her to the slave market and got a good price for her. Though I heard she was ransomed after a year.”

The captain called out for the food to be brought: some fish which Caroline could not identify but which was very fresh, some potatoes and greens, and then some cheese. The captain kept filling her wine-glass, which amused her somewhat. He doesn’t need to get me drunk to take advantage of me, she thought. I’m completely at his mercy; he can do exactly what he likes. They finished their meal and the dishes were cleared away. Caroline was in a playful mood; perhaps it was the wine.

“Is this the point at which you fuck me?” she asked, with a demure smile.

“I would not expect a lady to use such language,” he replied. Surely she could not have shocked him?

“Perhaps you don’t know much about ladies,” she said. Was she trying to provoke him? To what?

He was silent for a moment. “Come here,” he said.

She got up from the table and went round to where he was seated. “You’d be surprised what I know about ladies,” he said. “It’s often the fine ones who are the most depraved.”

“I hope you don’t think I’m depraved,” she said, still playing the coquette.

“I think you would be if you stayed long enough with me,” he answered. “Now bend over the table.”

She did as he said. He lifted up her negligee, exposing her bare bottom. She tensed, waiting for another slap on her buttocks. Instead, the captain bent forward, pulled her cheeks apart with his hands and kissed her full on her asshole. Caroline gasped. No one had ever thought to do such a thing. She didn’t know how to respond; was it erotic, or was it just filthy? Before she could decide, the captain began to lick around the tight little orifice with his tongue., He circled slowly, every now and again pressing the tip of his tongue into the centre, as if he would penetrate there, but his tongue lacked the necessary stiffness. Caroline clenched the muscles there, quite involuntarily. It wasn’t that she wanted him not to do this, but she had no experience of it, and closing herself there was an instinctive action. Yet as the captain’s tongue worked on her more, circling, pressing, circling again, she found herself relaxing, opening up. Henry had buggered her once or twice, but he had done nothing like this, merely lubricated her rather perfunctorily before pushing in his cock. This was different, a sort of anal seduction, easing her into the pleasure of it, gaining her confidence, teasing her so that she wanted more, wanted to open up like a flower for him and for him to dip in deep.

While his tongue worked, the captain put a hand around her waist then slid it down till it was between her legs. Unerringly he found her clit, already swollen. Pushing his finger quickly into her cunt, he spread her juices over her clit and began to stroke it as he had done last time, with movements that were precisely what she would have done for herself.

Caroline sighed. Was anything ever as pleasurable as this? The captain kept sliding his tongue around the tight little orifice (not quite so tight now), while his finger coaxed her clit towards the ultimate pleasure. She was unsure what would come next. Would he make her come? Or would he bugger her, sliding his big hard cock into the space he had prepared?

As chance would have it, the oil which had been provided to dress the salad was still on the table. The captain drew it towards him and carefully poured a little onto his fingers. Then carefully, almost tenderly, he slipped first one finger then two into the puckered little orifice. Caroline forced herself to open up. She was eager to receive him now, eager to minimise her resistance to him, wanting the space filled by something even better than fingers.

The captain got to his feet. She knew what was coming. He placed his cock precisely between the cheeks of her bottom, the tip resting against the little hole. Caroline herself ready for him, pressing down to open herself. But however much she did so, the captain’s cock felt huge, far too big for that delicate little place. As the captain pushed against her, Caroline gasped and tried harder to open up. But she wondered, as she had wondered when Henry had first taken her this way, whether it was even possible for a man to enter a woman like this. The captain, however, was in no mood to be denied. He was not cruel, but he was firm and determined. It felt to her as if resistance only stimulated him to press harder, and the head of his cock suddenly slipped inside her. The captain grunted with satisfaction. Caroline felt so full, surely she could not get fuller than this, but the captain kept pressing and as she got used to his cock her ass seemed to adjust and penetration became easier, until at last the captain’s cock was lodged wholly within her.

For a moment the captain was still, though she could hear him breathing hard. “God, that’s good,” he said. “I think you have the best ass I’ve ever seen. Or fucked.”

Caroline did not know how to receive this compliment, but since her face was pressed to the table she was not obliged to react. Slowly the captain withdrew his cock, just a little way, then pressed back in. Caroline began to relax. She could take it; there was no real pain, and indeed, she reflected, the pleasure of being taken in this manner easily outweighed any discomfort. It wasn’t just that it felt so good to be filled with cock there. There was something about it that appealed to her. She viewed it as a perversion, an unnatural act, and she was beginning to realise that she was drawn to such things. Sex for her would never be a matter of straightforward intercourse. That was pleasant enough. But she was coming to see that she needed more. She needed to be pushed, stretched, impelled towards not just enjoyment but debauchery. And she needed a man who could push her in that direction. It seemed as though the captain was just such a man. But unfortunately, he did not value her enough to keep her. Having taken his fill of her, he would sell her to the highest bidder.

But then, she thought, as the captain began to thrust harder, his lust increasing as he saw his cock thrusting into the lovely, rounded, white bottom of the girl bent over beneath him, what future could she realistically have with the captain, even if he were to fall headlong in love with her? Could a woman such as herself sail the seven seas as the companion of a pirate, an outlaw pursued by all the navies of Europe? She gasped as the captain drove into her harder still, piercing her tight little asshole, stretching it till she feared he must rip it, but in fact he did not, either because he had prepared her so well or because Caroline had managed to overcome her resistance, had learned how to relax her anus so that it could accommodate a cock the size of the captain’s. Buggery, sodomy; such a wicked act, it seemed. Was that why she got so much pleasure from it?

With an oath the captain ejaculated into her. She imagined his hot semen scalding her as it spurted into her bowels. Then he withdrew and she no longer needed to imagine, she could feel the semen dripping from her, oozing out and running slowly down the inside of her thigh.

She hadn’t come, but she didn’t care about that right now. She could take care of her need later, while the girls slept in the darkness of the hold. The captain was in a companionable mood. He offered her more wine. They spoke a little of her fate. Slavery, he said, was not the worst thing that could happen to a woman, not in the circumstances in which she would experience it. Some women, he said, if they played their cards right, could rise to positions of influence, could find favour by their skills in bed and parlay them into a position of comfort and even influence. Caroline treated this with scepticism. A slave was a slave, was she not, and always at the mercy of her owner and his whims. But she was a girl of spirit. Even if she thought the captain was telling her these things only because he had some feelings for her and wanted to give her some hope, she resolved to make the best of it. Moping would get her nowhere. Fortunately, she was a girl who loved love, who enjoyed to the full the pleasures of the flesh. She was an imaginative and talented lover, who had benefited from an excellent teacher, and maybe she could eventually show her owner a trick of two.

Caroline took her leave of the captain and went back to the other girls, who appeared to be sleeping. After quickly giving herself relief with her hand, during which she relived again the recent act which the captain had performed upon her, she slept well. The next day up on deck she fell into conversation with two of the other girls, Sally and Nell. They were both curious about her time spent with the captain. Caroline answered their questions without giving away much detail.

“And how goes it with you?” she countered. “Do the men use you hard?”

“Sometimes they are a little rough,” Sally admitted. “But I feel a bit sorry for them, at sea for weeks on end with no female company.”

“Do you think they ever turn to each other for relief?” Nell said. There was a sly look in her eye. “I’ve heard it said that men will do that if their need is great.”

“I think if you asked them you might get a black eye,” Sally said. “It’s not something they would want to admit.”

It was also not something Caroline had ever thought about. Two men together, touching each other? What sort of things would they do? Suddenly she had a vision of one man doing to another the very thing the captain had done to her the night before. The thought was disturbing, yet strangely arousing.

“The captain is rather handsome, don’t you think?” said Sally, reverting to their earlier topic.

Nell laughed. “He could do me, any time he wanted.”

It had not occurred to Caroline before that the girls might envy her the sexual element of her nightly encounters, only that they would know she was getting better food and other comforts. This thought led to another. Was it fair that these girls (she thought there were only four in all who volunteered) should shoulder the whole burden of servicing the crew? Ought not she, Caroline, to do her share?

On an impulse she made an offer. “The next time a sailor comes looking for a girl, I will put myself forward. It’s time I did my bit.”

Both girls looked at her with surprise and admiration.

“Really?” said Sally. “You’d go with the crew, my lady?”

Caroline smiled. “I don’t feel much like a lady any more.”

It was early evening before one of the crew came. It was a warm day and the hatch had been left open. A burly sailor climbed down.

“Who shall it be tonight, girls?” he said with a leer.

Caroline stepped forward. “It’s me.”

The man looked her up and down. Then he grabbed her hand and pulled her up the steps. Out on deck several of the crew were lounging about, smoking their pipes. The man led her to the front of the ship, into the screened area that the girls washed behind. Caroline saw that four men were sitting there expectantly.

“Look who we’ve got tonight, lads,” the man said. “It’s the hoity-toity lady. I think she fancies a bit of rough trade.”

“Then she’s come to the right place,” said one of the men with a laugh. “Come here, darling.”

He reached out and grabbed her by the waist, pulling her onto his lap. The other men sat watching. Apparently she was to be a spectacle for all of them. The man pulled her nightgown up over her head, tossing it aside.

“Look at her tits,” he cried. “Lovely.”

He caught her hair in his hand and twisted her face up, kissing her full on the mouth. Caroline tried to pull away; his breath was bad and he tasted of tobacco juice, but he forced himself on her, pushing his tongue into her mouth. At the same time he put his hand between her legs. Instinctively she clamped her thighs together, but he was strong and forced his hand right up to her crotch, then pinched the lips of her cunt till she cried out.

Pulling his head away from her, the man cried to his companions, “She likes to resist a little! There’s plenty of fun here, boys.”

Caroline realised that any attempt to thwart their desires would only make them stronger. The line of least resistance was the way to go. She wouldn’t go limp; complete inertia might only provoke them. She would have to play it carefully, fighting just enough to get them thoroughly aroused, so that they would come quickly and so conclude matters.

In the corner was a pile of sacks. The man holding her got to his feet and dragged her across. “Hold her down, lads,” he said.

One of the men held her wrists above her head, the other pushed her legs apart. The man who had kissed her stood over her and lowered his breeches. Caroline gazed up at his cock. It was big and hard, the foreskin pulled back to reveal the dark red head. The man touched himself for a little while.

“Give it to her, Charlie,” said one of the watchers.

The man knelt between her legs and lowered himself. Caroline felt his cock pressed to her cunt, then with a single hard thrust he was in her. He appeared to have no interest in the niceties but fucked her vigorously, straight in and out, for five minutes. Caroline stared up at the sky. Once, while masturbating at home, she had imagined such a scenario, coarse, even brutal men taking turns at her, slaking their lust. Now she was finding out the reality. It wasn’t erotic in the way she had imagined. If she had allowed herself she might have been frightened, even though she knew that if she screamed the captain would come. But if they wanted to, they could hurt her. And yet, though they were focused entirely on their pleasure and not her own, she began to see that she could take the initiative if she chose. Their need was great, and though they undoubtedly took delight in debauching a high-born lady, they also had an innate sense of deference. She doubted if they would have the nerve to do her harm, not in a situation in which their crime would be immediately discovered and punished.

With an oath the man fucking her ejaculated. Caroline felt his cock kick and buck within her as the semen spurted from him. Then he pulled out.

“Who’s next?” he said to the others. “What about you, Harry?”

Harry was the man holding her wrists. He pulled her up onto her knees. He stood over her and pulled down his breeches. Seizing her hair, he pulled her face towards his cock. She could smell it, somewhat rank to be sure, although the smell of cock never failed to tug at her cunt. She opened her mouth and let him force his way in. The cock was not particularly long but it was thick and she had to open wide to accommodate it. If allowed she would have willingly offered him some of the sensuous caresses she liked to give a man, licking and sucking and teasing. But it seemed he had no interest in this. Instead, he thrust in and out rapidly, seeming intent only on reaching a climax. Despite this, Caroline put up her hand and took hold of his balls. She squeezed gently and was rewarded with a grunt of pleasure.

“Damn,” the man exclaimed. “She’s a right little whore.”

With that he came, copiously, so much semen pumping into her mouth that some of it ran between her lips, down to her chin and dripped onto her breasts. Now there were three left to service. It appeared this wouldn’t take long.

“Your turn, Tom,” said one of the men. Tom pushed her forward onto all fours and knelt behind her. He pulled her legs further apart, then manoeuvred his cock into position. Caroline felt it dig into her. This time she was not fucked in such a strenuous manner. Tom evidently intended to take his time. Caroline looked one of the men in the eye; he stared at her for a moment, then look away. She could control them all if she wanted to, she felt sure.

“Use her mouth, Billy,” said Tom to another man, young, almost a boy and good-looking. Billy knelt in front of her, took out his cock and put it to her lips. Caroline opened her mouth and took him in, sucking hard. The boy gasped with pleasure. She wondered if this was his first time for such an experience. As Tom continued to fuck her with a steady rhythm Caroline concentrated on maximising the boy’s pleasure, varying the caresses of her tongue and lips, kissing, licking, sucking and occasionally biting just a little. It wasn’t long before Billy came with a cry, pushing his cock deep into her, the semen spurting to the back of her throat.

Tom continued to fuck her. She rather enjoyed it now and wiggled her bottom a little so as to vary things. Tom responded willingly, squeezing her bottom with his hands, slapping it from time to time, then, to her surprise, suddenly pushing his thumb into her ass. Caroline moaned.

“She’s liking it,” Tom said. “She’s a whore, just like the others.”

The men all laughed. At last Tom finished. When he pulled out semen once more seeped from her cunt, running down the inside of her leg. Was she indeed not a whore, dripping semen, her face running with it. her cunt drooling?

Caroline sat on the floor, facing the men.

“So,” she said, beginning to enjoy herself, “there’s one of you left, is that it?”

The last man nodded, eagerly.

“Unless any of you is man enough to come again,” she said with a slow smile.

“My god,” said Tom. “What have we here? Not a lady but a slut.”

“Come here,” Caroline said to Ned, the man whose turn it now was.

She positioned him in front of her as she knelt upright. Quickly she undid his breeches and took out his cock.

“What a lovely one,” she exclaimed. She took it in her mouth, sucking greedily. Then she pulled back.

“You and you,” she said, pointing to Charlie and Harry. “Come here.”

She indicated they should stand on each side of her. Reaching into their breeches, she brought out both their cocks, which were thick but no longer rigid. She bent forward to take the first man in her mouth again, while holding onto the other two cocks, one in each hand. Once, in the throes of masturbation, she had a vision of herself in just such a pose, never supposing that it would ever materialise in reality. Now she was enacting her fantasy. She began to rub the two cocks she held in her hands while still sucking enthusiastically on the cock in her mouth. The rest of the men watched, fascinated by such a display. Soon the cocks she held were rigid. Taking her mouth away from the cock she was sucking, she spoke to Charlie.

“Get on your knees and fuck me from behind.”

Charlie needed no second invitation, getting down and thrusting his cock right up inside Caroline’s cunt. Before taking a cock back in her mouth again, she called to Harry.

“Come here. Let me hold your cock too.”

Harry came forward and Caroline seized his cock. She was now fully occupied with sucking the cock in her mouth while still jerking off the two in her hands, and enjoying at the same time being fucked from behind. Only one man remained on the outside, watching. It was Billy; Caroline addressed him, her mouth still full of cock.

“Stand in front of me, next to Ned. When he comes, you come too. Jerk off over my face, like a good boy.”

All five men now concentrated on the girl who manipulated them, each growing closer to ejaculation. Suddenly Ned groaned and semen shot from his cock, most of it going down Caroline’s throat but some escaping between her lips. A moment later Billy, pushing his cock forward till it touched her face, shot a stream of thick warm semen over her cheeks and forehead. Not missing a stroke, she continued rubbing the two cocks she held and was soon rewarded with further streams of creamy white semen, some splashing onto her face, some onto her breasts. It only remained for Charlie to finish. Thrusting vigorously into Caroline, while smacking her ass, he soon reached completion, withdrawing at the last moment to release a spurt of semen into the cleft of Caroline’s ass.

She knelt on the deck, dripping semen, her face flushed but happy. Who would have ever dreamed that Lady Caroline could do such a thing? She had surprised herself by the raw animal lust that had overcome her, the urge to take things as far as she could, take on all comers (literally!). The men gazed at her with a sort of awe, impressed by her single-minded pursuit of their cocks, admiring of the dexterity with which she manipulated them all.

Caroline stood up and went to the tub of water at the side of the deck. She splashed water on her face, her chest and between her legs, then dried herself with a somewhat grubby towel that hung nearby. She picked up her discarded nightgown and put it on. Then she smiled sweetly at the men.

“Thank you all for a memorable encounter,” she said. Then she turned and, a trifle unsteady on her feet, walked towards the hatch and descended into the hold. She wondered if she would once more be summoned to the captain’s cabin that evening. But a few minutes later there was a shout from above and the sound of men running across the deck. Caroline rushed up the steps to see what was happening.

“Sail ahoy,” one of the men called out.

There was something approaching panic as the crew ran in all directions, the captain shouting orders. Clearly the sight of another ship filled them all with fear.

‘What ship is it?” the captain called out to the man in the crow’s nest atop the main mast.

“Can’t see yet, cap’n, but I fear it’s a man o’ war.”

In a few moments the ship had all its sails up and Caroline could feel the speed increase. No one took any notice of Caroline, who stood at the side of the ship and watched. After half an hour of sailing it did not seem as if the ship behind them was getting any closer. And it was now dusk. Soon the darkness would offer them safety. It was getting cooler, and Caroline went below to sleep.