Surrendering to the Pirate
Evelyn decides to give Captain Howell what he wants
PART SIX of the Pirates of the Caribbean serial
If you are new to this story serial, read PART ONE, Pilgrims Below Deck, or review the summary by clicking here.
Sailing westward, the pirate ship entered the eastward flowing Gulf Stream. Here, their headway was sharply reduced. They paused their westward travel to plunder more ships. From one ship, they took aboard twenty Africans. These were imprisoned below the deck.
A few times a week, Captain Howell found a reason to spank Evelyn. These sessions ended with her providing a hand job. Her skill increased, and she discovered he liked it best when she made the process last a long time. The more he enjoyed it, the kinder he was toward her. While he spanked her, the punishments became teasing — sensuous. She looked forward to them and occasionally, intentionally blundered so as to attract his discipline.
Four months after Evelyn had been kidnapped from her Uncle’s ship, they dropped anchor in Havana.
“M’lord, how long are we going to be here?” Evelyn asked.
“A month, this is the endpoint for this cruise. We will sell our stolen cargo as would any legal merchant, and the bounty will be distributed among the men. The men are then free to leave the ship’s company. Some will take their new wealth and attempt to buy their way into a legitimate life. Then I will refill the ship’s company, and we will set off for New Providence.” He gripped her chin and pulled her face upward. When he had captured her eyes, he continued, “You, I’m afraid, will be required to remain on board.” He released her and turned away. “Remain in your galley while the cargo is off-loaded.” He walked away.
With the pirate ship anchored in Havana harbor, most of the crew took their share of the booty and went ashore. Evelyn remained aboard under guard. She considered trying to escape. While this was a Spanish held island, it was a major trading port. Surely there would be an Englishman who would help her. However, punishment for trying to escape, and failing, would not be a teasing spanking. It would be an unbearable abuse. She had escaped buggering once, and been warned.
Other than the sailing-master, the quarter-master, and a hand full of sailors loyal to Captain Howell, the crew disbanded. Whether or not the men returned was their own choice. Each pirate began their stay in Havana with a small fortune. Over time, many of them returned to the ship. While she did not have any conversations with them, she overheard several of their stories of drunken debauchery — spending their money on rum, gambling, and prostitutes.
Doris also went ashore. She returned after two weeks, with most of her money intact. “It’s an exciting city,” she said, “anything can be had for a price!” She went on to describe the prostitutes willing to lick her pussy. Evelyn enjoyed cuddling and touching her friend, or rather she enjoyed Doris touching her. But, she closed her ears while Doris described these more extreme acts. Doris did not press her into a more active involvement in their lovemaking. While Evelyn’s time aboard ship had been excruciatingly boring, she was not sorry she had missed the experience of the city. The one positive factor was the steady supply of fresh food.
When a full complement of sailors/pirates had been assembled, Captain Howell ordered the ship to be careened along the northern shore of the harbor to clean its bottom. Evelyn watched as the ship was intentionally beached at high tide. As the tide fell, the ship rolled onto her side. Evelyn and the men camped ashore. Another ship was also being cleaned fifty yards away, and Evelyn wondered if she was a merchant ship which could take her to safety.
As darkness fell, she dug a fire pit in the sand to cook dinner for her and Captain Howell.
“If you break your pledge to me,” he said, watching her stare at the other ship, “then I will no longer be held by my pledge to keep you a virgin.” Evelyn looked down and began to stir the coals in their campfire. “If you want, you can try to escape. I will, of course, capture you.” His momentary silence emphasized his next words. “I can then take your maidenhead.”
The meaning of Captain Howell’s discussion became clear to Evelyn. He wants me to offer myself to him!
Strange muscles deep within her belly began to quiver. She watched his face soften into a warm smile. The idea of laying with him had long since stopped repulsing her. She pressed her thighs together, hugging her swelling pussy. She wished they had sufficient privacy for him to spank her. She longed to have his hand on her bare bottom — smacking and caressing her.
With her face turned away, she spoke slowly. “My Lord, while no true gentleman would have kidnapped me in the first place, you have shown me nothing but kindness since that unfortunate day. However, I cannot offer you that physical expression of my gratitude.” She swallowed. “I cannot sully the memory of my parents by granting my maidenhead to a man before marriage.”
He grunted and turned away from her. In the darkness, Evelyn pressed her hand to her groin in an effort to quell the tremor within her — her pussy clenched and dampened her pants. Despite being in the company of scores of men, Evelyn had been desperately lonely during the past months. She longed for his strong arms to comfort her; his warmth close beside her. She enjoyed those evenings when he spanked her, and she released his seed with her hand. She considered attempting to stroke his manhood.
Perhaps granting his wish would not be so bad.
She remembered the words of the prostitute Hillary from the brothel where she had been a cook, “Buggering is my favorite way to take a man.”
“However,” Evelyn continued, speaking to his back, “if you want to have me in another way, I will not refuse.” She untied the rope holding up her breeches. She pushed them down to her knees. Laying on her side, she pressed her bare bottom against his back.
In the morning, she sipped tea and watched the men working, cleaning the ship’s bottom. Captain Howell had shed his shirt, and she admired his broad chest and thick muscles. She admired the way his wet breeches clung to his loins; she could see the outline of his cock.
I’ve been buggered. I’ve had that cock inside me.
Pulling her knees up, she wiggled her bottom into the sand. Through the cloth of her breeches, the sand pressed between her butt cheeks. She wiggled again to massage her tingling hole; her flesh retained the memory of his penetration. Closing her eyes, she imagined how the scene might have looked, had someone passed by — her bare bottom shining in the moonlight with his throbbing cock protruding from it.
The first part had been very pleasant. He had rolled over, toward her. In the darkness, his hand had explored what she offered. Holding her close, like two spoons in the drawer, his hand had explored up her torso until he found her tiny breasts. He opened her shirt and lightly pinched her nipples until they stood erect for him. He had nuzzled against her neck; he had kissed it. His boner pressed hard into her backside.
Then his hand had returned to her bottom. He opened her and presented his cock at her entrance. She tried to relax her opening, but he did not press in to her, as she had expected. His fingers opened her wider and explored her womanly folds. His cock followed to her other entrance.
“No,” she had said.
“Don’t worry,” he whispered, “I only want to coat my cock with your dew. This will make it easier.”
She had followed his guidance and allowed his cock to stroke back and forth along her slit. Sparks flew within her as he bumped against her clit. She could smell the scent of her moisture as it flowed from her channel. His fingers coated her butt hole with a mixture of his saliva and her juice.
The next part had been somewhat unpleasant. His member returned to her back entrance and pressed against it. She tried again to relax her opening as he thrust against its tightness. When his tip first gained entry, it was an uncomfortable stretching sensation. As he thrust deeper, there was a moment of pain.
I rather imagine that is what breaking my maidenhead will be like.
And then, he had slipped past some barrier within her, and took possession of her. Holding her hip, he gently pumped his tool in and out. The sensation was a pleasant fullness; she enjoyed being filled with his attentions as he worked himself deeper within her bottom. When he burst forth his seed, she could feel the pumping pulsations of his cock. That was the best part, the part her body remembered.
Evelyn opened her eyes. She smiled and touched the spot on her neck where he had bitten her as he climaxed.
When the work had been completed and the ship re-floated, Captain Howell gave the command, “Weigh anchor!”
The ship returned to the Florida Straits. They set out in search of Spanish treasure ships.
THE END of this part, but PART SEVEN — One in the Butt or Two in the Hand, continues the story.
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