Gwendolyns Story

Gwendolyn was the attractive wife of a wealthy seagoing merchant (Pirate to you and me.). When he failed to return from an expedition financed by some wealthy but ruthless associates, Gwendolyn, his beautiful young wife, was taken as payment for the debt.

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The beautiful Gwendolyn Alder was seated totally naked on the bed in the small room. She was weeping softly, her spirit broken; her world of luxury and plenty had suddenly crashed around her. Only a few months ago, she was a respected member of Abbotsford society. Gwendolyn was the beautiful young wife of Eric Alder, a seagoing merchant or privateer. The couple had arrived in Abbotsford about two years ago to settle down and start a new life after several many adventure filled years sailing the high seas and plundering the treasures of the New World. With their wealth Eric and Gwendolyn had purchased a large house on the outskirts of Abbotsford called Windfell Hall.

With some reluctance Eric had given up his seagoing days and moved in the Hall, Gwendolyn was pleased to have a home of her own at last and was happy to settle down and maybe even begin to raise a family.

When stories of their undisputed wealth circulated the area anybody who was anybody had clamored to get to know the attractive young couple. They were soon high on the list for being invited to all the best social gatherings and they themselves in return gave lavish parties. The problem was that Eric was good at doing what he did best: captaining a ship, exploring new worlds, pillaging the Spanish and French ships and bringing back the treasures that he found, but he was not so good as a business man and the many unscrupulous elements in the local society soon took advantage of his lack of business acumen.

As their wealth quickly diminished, Eric was getting to the position where he needed to restore his wealth. This meant taking to the high seas again, his so called friends saw the opportunity to make even more money from him and were quick to offer investment in the new venture, providing funds for him to equip and crew an even larger ship.

Gwendolyn much to Eric's disappointment decided that she was happy in her new home and decide that she had had enough sailing the high seas and so decided to stay at home in Windfell Hall and await his return. Even so she was feeling quite sad as she stood on the quayside with some of the other investors and waved her good-byes as she watched The Black Witch, her husband's ship sailed off on the evening tide. What she didn't realise at that moment was that it would be several years before she ever saw him again.

For the first year or so of Eric's trip Gwendolyn was able to keep up her life style, but when her husband did not return and her dwindling funds rapidly diminished, she first had to cut back on her household staff, and then reluctantly make cut backs in her expensive and indulgent life style.

At first, her so called friends stood by her, but as the months and then years passed by and there was no sign of Eric returning; even the more trusted ones began to turn their back on her. The unscrupulous bankers and traders who had loaned her money on the strength of her husband's return with more wealth soon began to demand their money back, and when she couldn't repay it, they began to make moves to repossess her property.

The leader and instigator of this group was one Ezra McIntyre, a mean old miser who from the moment her first set eyes on the delightful Gwendolyn had designs on the young beauty's more intimate treasures as well as the returns on his investment in her husband. Things came to a head two years after Eric had sailed away. Two of Ezra's men arrived at Windfell Hall in a carriage and told Gwendolyn to come with them.

At first she was reluctant but they persuaded her that it was in her interest and in the end they led her out to the carriage and drove her back to Ezra's large mansion.

The men handed over to Ezra's manservant, Manners, who escorted her into the large library. Ezra was standing with his back to the fire. He smiled and nodded when she walked in. "Come in, come in, my child; make yourself comfortable. Can Manners get you a drink of something?" Gwendolyn shook her head she wanted to get this interview over so Ezra waved the old manservant away.

"You've been brought here because of your escalating debt problem. We don't know what's happened to your husband. He ought to have been back months ago. Now things are getting serious and something needs to be done about it."

Gwendolyn smiled nervously. "I'm sorry, but what can I do? I've been as frugal as I can, but there is nothing more I can do until Eric returns."

Ezra shook his head. "I'm afraid that's not good enough. We need to do something now. My friends need a return on their money that they entrusted to your husband."

She shrugged. "I'm sorry for them but what more can I do?"

Ezra smiled. "Well, that's up to you, my child. An attractive woman like you can always find ways of extending her credit." Ezra looked at her meaningfully.

Gwendolyn had an idea what he was getting at she had often seen the lustful way he looked at her and she was a woman of the world, but she dismissed it. Surely In her position, such a thing was unthinkable, or was it? She shuddered at the thought.

"I must speak to you seriously about this matter," said Ezra, looking grave. "I have met with the other creditors, and they have agreed with me that if there is no news of your husband by the end of the month, then you will have to be held responsible for his debts."

"But I have nothing to pay you with," moaned Gwendolyn. "Everything I had is gone."

Ezra smiled a sickening smile and looked at her. "Not quite everything, my lovely."

With the sight of his grinning face still in her head, she was driven back home. The end of the month came all too soon for Gwendolyn, and there was still no news of Eric. On the first of the month, Ezra's coachman again arrived to collect her and she was escorted once more to Ezra's mansion. This time when she was taken into the library, Ezra was seated at his large ornate desk and to Gwendolyn's discomfort the four other major investors were also there.

"I hear there is still no news of your husband my dear?" Ezra said addressing the now frightened young woman.

Gwendolyn shook her head.

"Then I'm afraid we have no other options left," he said, looking around at the others who were nodding their heads. "You must start to pay off some of the debt yourself."

"What with," Gwendolyn moaned. "I have nothing left, nothing at all."

Gwendolyn saw the men around her smile at each other.

"You have one very precious thing," Ezra said with a lecherous grin. "Your delightful body."

Gwendolyn looked at him in horror. "You wouldn't, you couldn't. I'm a happily married woman."

"Then where is your husband and where is our money?" Ezra shouted above her moans. "We don't see him or the money around anyplace."

Gwendolyn fell to her knees, sobbing. What could she do? She felt helpless.

She suddenly looked up at them. "I won't do it! I won't let you! You have no right!"

Ezra smiled again. "Oh, yes we do, my dear. Of course, the other option for you is the debtor's prison. But I don't think a lady like you would like that, would you?"

This announcement frightened Gwendolyn even more then the first one. Now there was little choice in the matter. She had witnessed in person the indignities that the people sent to the debtor's prison were put through, particularly the women debtors. After being found guilty by the court, they were taken out into the street and publicly stripped naked. Then they were paraded through the streets always lined with jeering crowds, who pelted the poor women mercilessly them with eggs and rotten fruit. Their destination was the market square. Here they were secured, still naked, to a whipping post and left there until dusk. It was here that some of the worse degradations took place as they were left to the mercy of the local crowd. Their bodies were often whipped and abused, and some of the more perverted of the spectators actually involved themselves in depraved acts of sexual intercourse with the unfortunate wretches.

This public torment was only over when as dusk fell the prison guards released them, and they were then taken to prison for the required term. It was well known that once inside the prison, some of the worst atrocities took place, by both the sadistic guards and even their fellow prisoners. It would be especially bad for someone as attractive as Gwendolyn and she knew it.

She now knew that she had only one option that would mean her survival. She had to agree to their demands whatever they were. She knew it was not going to be pleasant, but if it meant she could at least play for time, the time she needed for Eric to return to her and take her away from all this, she knew she would have to do it.

She stood looking at the five men. She was angry and afraid but she didn't want to show them she was weak. "You will all be sorry when Eric returns and he discovers what you have done."

"If Eric returns," she heard one of the men say to his companion.

"Well, gentlemen, I think the matter is settled. We will sort the details out later." Ezra spoke and the men around him nodded in agreement. "I think the first matter on hand is for us to

check out the goods on offer."

She saw the men look at each other and smile. The problem was that Gwendolyn was not some innocent frightened little virgin. She knew what these men were after since she had spent five years on the high seas with Eric and his crew aboard the Black Witch. This life had taught her a lot about the needs of men and especially how they treated women who were under their power.

During their many daring adventures together, she had been involved in the capture of several ships and their crews. Eric was hard and ruthless, but he was not a bloodthirsty man who killed for the sake of it. He was after the wealth and the cargo on the ships, not the crew who were only there doing their jobs.

When the ship was captured, there was of course fighting. People did get killed and maimed on both sides, but then the ship was ransacked and any cargo of value transferred to the Black Witch. Then before the ship was sunk or destroyed, the crews were set adrift in longboats with enough food and water to get them to the nearest landfall.

Occasionally on searching a ship, the men came across women. Prostitutes were often smuggled onto ships by the crew, and sometimes the captain had a woman or his wife aboard with him; the privilege of rank. On rarer occasions they came across a ship carrying women passengers.

These situations could cause problems for Eric.

The crews were at sea for months on end, and when a woman was found, he could do little to stop his crew taking advantage of the situation, without causing a mutiny. He did not like it, but he did not prevent it. Luckily, most of the women discovered were already prostitutes. They were well used to handling sailors, and what's more, were usually happy to be with the winning crew on board a ship rather than in a longboat with the defeated crew.

She would always remember one particular incident when they had came across a ship flying the Spanish colors which they had taken after a brief fight. They not only discovered a horde of treasure, but also an Ambassador's daughter accompanied by two young maidservants and an older woman retainer who was her guardian.

Eric had taken the women on board and locked them all in a cabin while the crew transferred the treasure. Then amid abuse and threats of retaliation from the Spanish captain, they had cast the surviving crew and the ship's officers adrift in the ship's boats before sinking the ship. Eric watched the once proud ship sink with some regret If it had been later in their voyage, Eric may have put some of his own crew aboard the captured ship and sailed it home. It would have made a good prize.

After they sailed away from the sinking ship, the crew was all in a rowdy and excited mood as they always were after a victory and ready and eager to get at the female captives. Eric knew that the Ambassador's daughter would make a good prize, and if she were unharmed, she would fetch a good ransom, but she was an attractive lass and the crew was eager to get at her. Eric called Gwendolyn aside and told her to go to the girl and find out just who she was and where she was bound and any other details she could discover. She should do this as quickly as possible while he was up on deck speaking to the crew.

All the women were frightened when she entered the cabin and they were more surprised when they found out she was a woman, as on board ship Gwendolyn usually dressed like a man. She had always found men's clothes easier to work in.

The two maidservants were really scared. They cowered in the corner of the cabin and refused to speak to her. According to the older woman, they had heard what pirates did to the women they captured. Even though she was scared herself she did manage to find out from the older woman that the Ambassador's daughter whose name was Cassandra she was on her way to marry some Duke or other who was governor of some Spanish held islands.

Gwendolyn discovered that Cassandra herself was certainly the haughty type and seemed to have no fear of the situation she now found herself in, she came over to Gwendolyn and demanded that she be released immediately. Gwendolyn remembered how she had smiled at the silly woman telling her, "I don't think you would like that, miss, as we are in the middle of the Atlantic Ocean."

When the girl heard this, she then threatened Gwendolyn with death and imprisonment when she was caught as she thought she surely would be. In the end, Gwendolyn had just gotten fed up with hearing her rave and left her and had reported her findings to Eric.

He listened to what Gwendolyn had to say, then told her that he had made a deal with the crew. They could have the maidservants as long as the other two were left alone. Then if everything went to plan, they would get a share of the ransom. Gwendolyn had felt sorry for the maidservants as she knew what they would have to suffer in the hands of the crew, but it was not up to her to say anything. Eric was the Captain and he was in charge on his ship.

Then the two girls were brought out struggling and pleading and were handed over to the crew. It was the last she saw of them for several days as they were dragged screaming to the crew's quarters below decks. That night as she lay in the big comfortable bed with her husband Eric, she could distinctly hear their cries as they were repeatedly raped and abused by every member of the crew.

The following day Eric told Gwendolyn that it would be about two weeks before they made landfall at the island where hopefully Cassandra could be traded for a healthy ransom. Cassandra made life difficult for herself during the voyage by continually complaining about everything. Her old companion was almost at her wits end trying to deal with the troublesome young woman, and the last straw came when she attacked the cook with a pair of scissors.

Whatever Eric's plans where for her, he couldn't condone this final action.

At noon he gathered all the crew on deck and Cassandra was brought out. She was struggling and spitting out some very unladylike language as she was held tightly by Big Amos, the ship's carpenter. Eric then told a crew member to lower a line and this was tied securely around Cassandra's wrists. Then she was hauled up till her feet just left the deck.

The young woman swung there as she still continued to struggle, shouting and screaming at everyone in sight. Eric turned to Gwendolyn. "I think this is a job for you, my dear," he said. "Go down and strip her." She looked at him, and he smiled. "If I ask one of the crew to do it, they might take things too far. As it is, I do have to punish her, but I don't want her too badly harmed. Bruised goods do not fetch as good a price as fresh ones."

Gwendolyn was not keen on the idea, but she could understand his thinking. She went down on the deck, and with all the crew watching on eagerly, she started unfastening the girl's clothing. At this Cassandra began screaming and kicking even harder, especially when she realised just what was going on. In the end, Gwendolyn had to use her knife to loosen and cut the braids and ties. As Gwendolyn struggled to pull off her tattered clothes, Cassandra began to quiet down, and began pleading with Gwendolyn not to go any further. Although she felt a little sorry for the girl, she knew she had to obey Eric's instructions.

At last the poor girl was down to her camisole and pantaloons. The crew was hushed and expectant. None of them had ever seen such a high ranking lady naked before, and it was a sight they were all looking forward too.

Gwendolyn cut the waistband of the pantaloons and they fell down over the girl's shapely hips and dangled from her feet. There was a cry as the crew got their first look at the dark bush covering her pussy. Gwendolyn could see that the girl was mortified to be exposed in such an undignified way before the ship's crew. She had to cut away the last item, her camisole, because her arms were tied above her head. As it finally fell away, the crew was rewarded by the sight of a perfect pair of naked breasts, stretched taught, hard pink nipples jutting out from large brown areolas.

Gwendolyn turned and looked up at Eric. He nodded and she made her way back up to the bridge leaving the young attractive girl hanging there now weeping silently, completely overwhelmed by the enormity of what had just happened to her. Her beautiful naked body was openly displayed and eyed hungrily by every member of the crew as it swung gently with the rolling motion of the ship.

"Mr. Beardshaw," Eric called out. The ship's cook pushed his way forward through the crew, his left arm in a sling. He looked at the naked girl hanging from the line and smiled. "Ten strokes I think should be enough to teach her a lesson, but try not to break the skin." The cook touched his cap and nodded. He picked up a short piece of wood, part of a barrel, and swished it through the air, testing its strength. The girl looked at him wide eyed and then cried out as the first blow landed across the firm white globes of her tight little bottom. After another few blows, her bottom was beginning to show signs of wear and turning an interesting pink color. She was by now screaming in pain, and well before the last blow landed, she peed on herself, much to the delight of the crew. They cheered as they watched the golden liquid running down her long legs and pooling on the wooden deck under her feet.

When it was over, Eric ordered that she was to be left there as she was until four o'clock with strict orders to the crew that they could look but not touch. Any member of the crew who did otherwise would be severely dealt with, and they knew to a man what that threat meant.

Eric did allow her elderly companion to go to her aid and bathe her wounds although he informed her that she could only tend to the girl's needs. She could not attempt to cover the poor girl's body. By the time Eric gave orders for her to be cut down, she had been totally humiliated, hanging there naked for everyone to see, and by the end of her ordeal, she was in a traumatized state. At least she caused no more trouble, and two weeks later, she was released into the hands of her intended for a handsome reward. Gwendolyn often wondered if she ever told her new husband what happened to her aboard the Black Witch.

All these memories flooded through her mind as she stood looking at the men. She knew what was meant by checking the goods out. She knew they intended to strip her to humiliate her, but they would never break her.