The Fool's Errand

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Some adventure at sea.
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Otto26
Otto26
78 Followers

(I'd like to thank the people who read this story and offered their time and talent in editing, particularly snooper and Intriguess. This story is very carefully told from the point of view of only one person. If you are wondering what the other characters are thinking or feeling then I invite you to use your imagination. If you are so inclined, please feel free to tell this story from the perspective of any of the other characters. I'd love to see your work if you do.)

The streets of Williamport were narrow, poorly maintained, and crowded, even several hours after sunset. Donovan hardly stood out from the swirl of torchlit colors in his scarlet coat and white wig, but he towered over the mainly Oriental population. He very much disliked Williamport, but it was a haven for rogues and scoundrels of all stripes and, thus, a good place to obtain information.

The girl appeared out of nowhere, thrust into his path by the market crowd, and there was nothing he could do. He ran her down, then he stopped and turned, casually elbowing a couple of people aside to clear some space so that he could reach her. He scanned the crowd around him before bending over to offer her his left hand.

"No harm done, lass?" he asked.

She shook her head silently and looked at him with fearful eyes before hesitantly accepting his hand and pulling herself to her feet. She was perhaps ten years old and thin as a rail, an obvious street waif.

"Do you know where you can get a meal with ten pennies?" he asked quietly.

She nodded warily and he dropped ten pennies into her hand.

"Then get yourself some food," he told her, "and say a prayer for the soul of Donovan Simms for so long as the money lasts."

Her hand closed in a death grip on the small coins and she darted glances about her before smiling once at him and then vanishing into the crowd. Donovan watched her go and then dismissed the incident with a sigh and set out, again, for his destination.

Away from the market the crowds thinned out considerably and the streets became darker. He was aware of someone following him and, for once, unsure how to deal with the problem. His pursuer was either very inexpert, or was making no effort to conceal himself. He looked around for a place where he might work unobserved and noticed a patch of darkness where there shouldn't be one. His hand, hooked into his belt, came out holding a death blossom even as the shadows started to move. The small torsion powered weapon in his right hand threw a cluster of darts at the first attacker as he turned his body to bring a second weapon in his left hand to bear on a second attacker. He discharged the weapon into the face of the second attacker and dropped to a knee as a third attacker tried to grapple his upper body. He used the spent weapon in his right hand to hook behind the knee of the third attacker and drove the palm of his left hand hard into the attacker's left hip. The man fell to the ground and Donovan drove for his throat, smashing it with his forearm. He rolled off and away, scrambling to his feet when he felt a wall he could keep at his back. He scanned the street for the fourth attacker, the one he had spotted following him, and saw him standing where he had last seem him. The rest of the street was rapidly emptying as passersby sought to rapidly be far away.

The figure shrugged helplessly, revealing a woman's profile, and struggled for words. She settled for, "Looking for a good time?"

Donovan laughed as he realized she was just a whore looking for a trick to turn.

"Not the blade I was intending to slip you, lass. Another time, perhaps?"

The piercing sound of whistles told him that a better citizen than most had encountered a watch patrol and cut off his laughter, which had threatened to become a semi-hysterical vent for the energy coursing through him.

"Hell!" Donovan swore. He had no desire to spend the next several hours or days answering questions and trying to bribe his way out of gaol. He turned towards the far end of the street and heard another whistle coming from that direction. A quick look down the alley showed it to be a dead end, blocked by a warehouse. He looked for a window, but found none not shuttered from the inside.

"Where are you going?" the woman asked him.

Donovan looked at her in surprise.

"Hire me," she said. "I'll send them the wrong way."

Donovan took another glance around the street before deciding.

"The harbor," he said.

"Into the alley then," she replied.

He ran into the alley and dropped into a pile of garbage, pulling it over him as best he could. From the street he could hear the pounding of feet and the insistent whistles.

"That way!" the woman cried. "Towards the square! In a black coat and wig!"

The feet pounded away and Donovan felt the desire to move, to burst from concealment, and quashed it as he had learned to do. He remained as still as possible, eyes closed and face down to the ground, willing his ears to see for him. He heard the slow crunch of footsteps in the alley and tried to relax his muscles to forestall the shaking he knew was about to set in.

"They're not gone yet," the woman said quietly. "Someone is interested in this. You're important to them."

Donovan was impressed, both by the fact that she knew enough to talk in a low tone without whispering and by her composure.

"You had the look of an officer. Are you from a ship?"

"Yes."

"Can you get me aboard?"

"No."

The silence stretched for a minute, broken only by faint sounds from the street.

"I need to leave this town. Tonight," she insisted.

"I agreed to pay you for a night, nothing else," he said to the street beneath his face.

"I'm saving your life, sir. I could as easily end it," she pointed out.

"You'll not live to collect any reward, lady," he promised.

"You'd kill me quick, sir. If I don't get out of town tonight then Ngia will take me and I'll die slowly. I've no wish to fall that far. Keep the money, but only get me away from here," she pleaded quietly.

"A night with you will not pay your passage," he countered.

"You're a cool one, sir," she said, "to bargain in such straits."

She paused.

"Very well, I'll work my passage."

"With what skills?"

"What do you think?" she replied scornfully. "I'll warm your bed, and no other, for the length of the voyage. I pick my destination and I'll depart when arrive."

"Is this why you were following me?" he demanded. "You were looking for a chance to get away on a ship?"

"You were kind," she said quietly. "To the little girl you ran over. Everyone else would simply have kept on, or given her a curse or a kick for her trouble. I thought a kind man would be a nice change. Yes, and I saw you had money to spare for an urchin and hoped you might spare a little extra for a whore. Do we have a bargain?"

"You'll have other chores," he told her. "There are no idlers aboard a ship."

"I have only your word to rely upon once I'm aboard your ship," she replied. "Swear to me you'll deal with me with justice and I'll swear to obey you."

"Done," he replied. "I so swear."

"As do I," she said. "Now remain still. This watchman bids to spend the night in a doorway across the way. I'll occupy him and meet you later. What dock?"

"Number twelve. Do you know it?"

"No, but I can read."

"A ship's boat. We must be gone before dawn, bargain or no."

"I'll be there before the horizon grows light. My oath I will," she said grimly. "Now hush."

Donovan waited until he heard faint moans issuing from the street. Cautiously he raised his head and scanned the alley. Seeing nothing, he slowly rose and checked to ensure nothing was clinging to the dark red coat. He stepped to the edge of the alley and looked out. The guardsman, a collage of shadows cast by his shuttered lantern, had his back to the mouth of the alley and his cock, apparently, to the mouth of the woman.

Donovan slipped out of the alley and walked slowly down the street. When he reached the end he turned and continued on towards the harbor. As he walked he pulled a small flask from his pocket and took a swig. Then, silently cursing necessity, he poured the rest over his jacket and shirt to cover, and explain, the smell of the garbage. Adding a stagger to his step, he made his way to dock twelve.

"Sod off you miserable... Christ's Balls! Captain Simms?"

"Yes, Simpkins. Thank you for your compliment on my cunning disguise. I had some bother along the way. Are we prepared to depart?" he asked the seaman standing guard on the dock.

"At your order, sir. If ye'd care to enter the boat."

"Not just yet," he replied, "some unfinished business to attend to."

They stood on the dock for an hour. Donovan didn't care to talk and neither of his men presumed to; if the captain wished to remain silent, then they would do so as well. A figure approached out of the darkness, hurrying but not running.

"I very much hope you are waiting for me," she said. "I've just spent the past half hour whispering unpleasant truths and lies about a certain pimp to an appreciative watchman. If you leave me here I'll be dead shortly after sunrise."

"We're ready to leave now," Donovan told his flabbergasted crewmen.

They clambered into the boat and the two crewmen cast loose from the dock before taking up oars. Donovan took the tiller and motioned for the woman to sit on the canvas-covered pile of goods that took up much of the boat. He steered the boat out into the harbor and took a handkerchief from his pocket.

"Somewhat the worse for wear I fear. Nonetheless, tie it about your eyes."

She caught the handkerchief and held it in her hands, folding it for a comfortable fit.

"What ship are we going to?"

"The Fool's Errand," he replied.

"A pirate ship," she stated.

"Privateer," he corrected her. "I hold a letter of marque and a commission from Good Harbor. If you know the Errand then you know her reputation, and mine."

She slowly tied the blindfold over her eyes.

"If you've any plots to carry out, please do so now," he told her. "Far easier to swim back to shore at this point. So if you have a grenade concealed beneath your skirts go ahead and threaten us now."

"If I could afford a grenade I wouldn't be whoring myself on the streets, Captain. I'll trust your word," she replied.

The seamen pulled at the oars for a good half-hour until they had passed the breakwater. Donovan lifted a shuttered lamp and flashed a signal at a light in the distance. The light blinked back and he quietly urged the men on.

They remained in the longboat as it was hoisted aboard the ship, only exiting once it had been lashed down. A short Oriental approached them.

"A special cargo?" the man said, pointing with his head at the woman. "You didn't mention this. Extra risk. Extra money," he concluded with quiet emphasis.

"Just a whore I'm transporting, Ping. My cargo is information," Donovan retorted.

"Doesn't look like a whore, Simms. I think you've mixed us up in something big. Big is okay, but only if we get paid for big," Captain Ping stated. His crew, Donovan noted, had become watchful, like a dog pack that senses the possibility of a fight and wants to subtly position themselves. His crewmen felt it too, but were too experienced to change their positions and give that knowledge away.

"Just a whore, Ping," Donovan repeated, "And a long story, which I'll tell you en-route. But I can see you need some proof. Simpkins," he called.

"Sir."

"Shag the trollop," Donovan ordered.

"Shag the trollop aye, Captain," Simpkins replied. He walked over to the woman and pushed on her back with one hand, pulling at her hip with the other to bend her over. He grabbed her skirts and flipped them up over her back to reveal a firm ass and broad hips, flesh pale in the half-moon. He kept one hand on her hip as he fumbled at the buttons on his pantaloons.

"Our bargain, Captain," the woman said softly, but did not move.

"Belay that order, Simpkins," Donovan ordered.

"Belay shagging the trollop aye, sir," Simpkins replied in a confused tone of voice.

"Good man," Donovan said, "but my honors, I believe."

He stood in front of the woman and unbuttoned his fly. Pulling out his cock he flipped it up against her face.

"Open," he told her.

She opened her mouth and he inserted his member. She closed her mouth around him and began to softly suck and lave him with her tongue. He rapidly grew hard and began to slowly pump into her mouth. She began to suck harder at him, audibly slurping. Donovan found the sound very stirring and pulled out of her mouth as he suddenly erupted, spurting cum onto her face. He stroked his cock a few times, milking it before putting it back into her open mouth.

"Clean it," he told her. "You see, Ping," he said the man, "just a whore."

The man grunted and turned away, snarling at his crew to get to work. Reluctantly, with many a sidelong gaze, the men returned to their work. Simpkins and the other crewman turned to face outward, giving their Captain what privacy there was to be found on the open deck of a large fishing vessel.

Donovan contemplated the woman before him as she continued her labors, seeking some explanation for the inconsistencies that nagged at his hindbrain. In the faint moon and lantern light her skin was a ghostly white and she was shaking fiercely, but she carried on nonetheless. With a good deal of skill he noted, for she was using her hands to caress his balls rather than readjusting her skirt to cover her naked bottom.

He pulled out of her mouth after a few minutes and tucked his cock back into his pantaloons, buttoning them up as he regarded her. She remained bent over, balancing uncertainly in the gentle swell, and made no motion to cover herself up or to wipe his sticky residue from her face.

"Stand up," he told her. "You're no blushing virgin nor yet a jaded whore. You trembled at the doing, but you did it anyway. A fallen lady?"

"Hard times force hard choices, Captain," she replied as she smoothed her skirts down. "I was taught to face the wind."

"That you apparently were. What is your name, lady? Your real name," he clarified as she opened her mouth.

She closed her mouth and then opened it again. "I prefer not to share that with anyone, Captain."

Donovan considered this answer for a moment before replying. "Fairly said, and I'll respect your wish on this matter. You'll answer to Lady aboard my ship."

"It pleases you to make a hard joke, Captain," Lady responded.

"It does," Donovan replied. "Hard times shape us all and I find my humor has grown somewhat grim over the years. We've a short trip ahead of us and you may not remove your blindfold during that time. That piece of deck will serve well enough, so take what comfort you can from it."

He remained silent and standing for the next several hours of the trip as he mulled the information his contact had given him. Around him the crew of the fishing vessel went about the never-ending work of keeping a ship afloat and in motion and his own crewmen sprawled comfortably on the deck, albeit watchfully. Lady sat down carefully on the deck and remained silent.

At length the Fool's Errand appeared ahead of them and Captain Ping began to maneuver closer to her. When they were but a short distance away he hove his vessel to and they began to make preparations to lower the longboat. Donovan reached down and assisted Lady to her feet.

"Time to go, Lady. Into the longboat with the rest of the cargo," he told her.

Simpkins and Gupta took her by either arm and assisted her into the longboat.

"Lean back against the tarp, Lady," he heard Simpkins advise her, "and pay no mind to how she swings. These boys don't want to look the fool in front of us and they'll set the boat in nicely. But don't touch that blindfold, mind."

Ping's crew did indeed put the boat into the water nicely. He pulled a small leather pouch from a pocket on his vest and pressed it into Ping's hand.

"My thanks, Captain," he said and then clambered down the side of the vessel and into the longboat. Long poles pushed them away from the side as the crewmen dipped their oars into the water and began to pull for the Fool's Errand.

The crew on the Errand was ready for them and made short work of hauling the longboat aboard. Simpkins and Gupta assisted Lady to the deck as Donovan made his own way. Lieutenant Liu saluted him.

"Your orders, Captain?"

"Make all available sail, Mister Liu. Mister Tran! Give Mister Liu a course for Iria. Best time and outside the normal shipping lanes," Donovan ordered. He looked around the assembled crew until he found the face he expected to see.

"Surgeon Brady, your inspection kit if you please."

"I have it to hand, Captain," the Hibernian replied. "You could hear the dicks hardening when Midshipman Tran spied the woman aboard the longboat."

He stepped forward and stood in front of Lady. He extracted a fine toothed ebony comb and began to run it through Lady's hair. He examined it for signs of lice. Finding none he put the comb aside and ran his fingers behind her ears and down her throat, prodding at her glands. Finding nothing that merited further investigation, he opened her mouth and ran his fingers along her gums and peered at her tongue and teeth.

"Already had some use of her, have you Captain?" he asked as he noted the dried semen that still splotched her face and blindfold. "I suppose the health of the Captain's cock is the Captain's business, but I don't know why you bother having me do my work if you don't care what the results are."

"Needs must, Doctor, needs must. Finish your work, please," Donovan responded.

The Surgeon grunted in obvious disbelief and returned his attention to Lady.

"Shuck and show, my fine tart," he said in a bored tone of voice.

Lady stood still and the Surgeon frowned.

"Drop it," he ordered.

"Remove your clothing, Lady," Donovan ordered by way of explanation.

The woman visibly steeled herself before slowly beginning the process of undressing herself.

"Bear a hand, woman," the Surgeon snapped, "I've other work to do."

The last of her clothing removed at last the Surgeon continued his examination, running his hands under her arms to probe her glands. Then he took his comb and ran it through her pubic hair and examined it. He inserted a finger roughly into her vagina and she gasped and winced, but made no other move as he roughly inspected her. Withdrawing, he bent her over and inserted his finger into her anus causing her again to gasp in shock and, Donovan judged, pain.

"A nice tight ass," Brady commented, "t'will be Chickendick's delight."

The crowd of lingering sailors roared in laughter at the coarse jest, but it only caused Donovan to notice them.

"Lay aloft you idlers, and haul in the anchor. We'll be underway by the next bell or you'll see no duff nor rum today," he snapped.

The crowd of sailors exploded into the rigging and all about the deck as each man threw himself into the assigned tasks with a will. Donovan turned his attention back to the Surgeon who was now pouring some alcohol onto his hand and then wiping it down with a cloth.

"Clean enough, Captain," he reported. "No plague nor pox and yet no signs of fever. She's like to tear a bit when you turn the crew loose on her. Better to find experienced whores, I suggest."

"She's not for the crew," Donovan said. "Take her to my cabin, please, draw the blinds and allow her to remove the blindfold. Remain with her until I return, but no touching."

"The men will feel hard used," Brady noted.

"They'll do as they're told or I'll drag them for shark bait," Donovan replied.

The Surgeon shrugged and took her by the elbow.

"Lady is it?" he asked sarcastically. "Follow me then, Lady, and mind you don't knock yourself."

Otto26
Otto26
78 Followers