Pegboy By Robert S. Costic
Robert Costic has written a collection of fairy tales, "Flamethrower Fairy Tales," a novella, "Kepler's Revenge," a collection of aphorisms, "Lightning Words," and a translation of the 19th century German writer Theodor Storm's fairy tales and ghost stories. All are available as ebooks everywhere.
Two pirate frigates in service of Great Britain, the Plunderer's Disgrace and the Awful Knave, chanced upon each other on a gloriously sunny day in the Caribbean and, once broadsides were tethered together, their crew celebrated by breaking open their casks of beer and, as their inebriation hit its peak, gangbanging the pegboy of the Plunderer's Disgrace, a young man named Henry who was famous among pirates for his insatiable sexual appetite and skills. A total of 160 sailors climaxed in or on him over the course of day, sticking their dicks in his mouth and asshole, one sailor after the other, so that early on they found themselves plowing not only into his flesh but also the warm, slick, and bountiful cum swimming inside of him.
The next morning, after nearly everyone had passed out from the revelry, the crew of the Plunderer's Disgrace found to their horror that Henry had disappeared along with the Awful Knave. The only trace of him was a puddle of cum that had leaked out of the swollen, pussy-like lips of his sphincter overnight. Captain Jonny Skewers ordered his crew, "Put the lookout for the Awful Knave! We must find our pegboy!"
Henry indeed found himself captive on the Awful Knave, kept with Jacob, the Knave's own pegboy, who told Henry, "I'm so embarrassed and sorry that my crew kidnapped you. If I had been a better pegboy they never would have done this."
"It's not your fault," Henry said, "don't blame yourself. Not every pegboy can be as good at sex as I am."
"But I'm no good at all!" Jacob said. "These days they don't touch me unless they must, because they derive so little pleasure from me. I have sometimes even caught them fucking each other, and I have taken it as sure sign as my failure to live up to my duties."
"That is a shame," Henry said, "Maybe I can help."
"How?" Jacob asked.
Henry took Jacob by the arm so that they stood face-to-face and kissed him on the lips. Jacob barely reacted. "Kiss me," Henry said, "and open your lips a little," and when Jacob did so Henry slipped his tongue between them. Their dicks stiffened and rubbed against each other, and when Henry noticed he dropped Jacob's pants, first jerking him and then putting his mouth around his cock. Jacob had never experienced this before, having only been on the submissive end of such pleasures, and having Henry going down on him revealed how it supposed to feel.
Before Jacob came Henry stood up, spun around, dropped his pants, and whispered, "Fuck me." Jacob grabbed his dick and searched for Henry's hole, and, finding it loose and receptive, slid it in.
"My hole is nothing like yours," Jacob said.
"It takes practice," Henry said.
Jacob wrapped his arms around Henry's torso so he could press deeply in him, and he fucked for all of thirty seconds before shooting his load of semen. Jacob knew it was quick and kept his dick in Henry to savor the moment, but once it softened it slipped out and all the cum poured out along with it.
"I'm going to teach you all I know," Henry said. "The Plunderer's Disgrace will be looking for me. By the time I'm found the Awful Knave won't mind giving me up because they'll have you."
Over the next several weeks Henry and Jacob played together whenever Henry was not busy with the other sailors. They alternated roles so that Henry could show Jacob how he took dick and then have Jacob practice. Henry's greatest difficulty was Jacob's tight asshole, which did not yield easily, but Henry rimmed it and lubricated it with his saliva until it could give way. From there Henry worked him in long sessions to pry him open. At first the ecstasy of being fucked came slowly to Jacob, but with each succeeding session it came faster, until eventually the pleasure came instantly.
One night, when seven pirates wanted to gangbang, Henry told them, "Let's fuck Jacob, too."
"A waste of time!" one of the pirates said.
"No thanks," said another.
"Men, give him a try. I've been teaching him. I can take only so many of you guys at a time anyway. Some of you can use him while you wait for me."
"Fine!" said one, and he forced Jacob to his knees and stuck his dick in Jacob's mouth. To his surprise Jacob took it with aplomb, and he moaned and began to guide Jacob's head with his hands to facilitate with the rhythm of his sucking. The other pirates whipped out their dicks and Jacob grabbed two to jerk off. Two other pirates stuck their dicks in Henry's ass and mouth. Soon the pirates were taking turns fucking Jacob as well. Henry and Jacob kissed and tongued each other, and when the pirates finished coming in both of them they took turns on each other, Jacob coming inside Henry's soaked hole and Henry coming inside Jacob's soaked hole.
From then on the pirates of the Awful Knave considered Jacob redeemed. They used Jacob and Henry equally and sometimes even found their pegboys taking the initiative. Sometimes if one of them found a pirate especially attractive or with an especially enjoyable dick they would find him in a hammock in the berth deck, jerk him while he slept, and then suck him off. If the pirate awoke to he never seemed to mind.
One day Henry was licking the cum leaking out of Jacob's asshole, which had just been fucked several pirates, and after he finished he rose and tongued Jacob, sharing with him all the cum he held in his mouth. Jacob swiped some of the cum off Henry's mouth with his hand and used it to lubricate the head of his dick, which he jacked off until they came.
"You know what?" Henry asked. "I love you."
"I love you, too," Jacob said.
"I know I said that the Plunderer's Disgrace would be looking for me, but if they ever do I don't think I could stand to leave you."
"I don't want you to go."
For some time they had nothing to worry about, but all of their carnal pleasures were eventually interrupted when the HMS Jupiter approached. The British captain met the captain of the Awful Knave, Paddy Noon, and told him, "There is a Spanish galleon that I want you to attack. I am prohibited from doing so myself because Britain is not currently at war with Spain and royal ships are therefore prohibited from attacking them. But I already engaged one pirate ship and want you to join. Any booty you capture is yours, split between you and the other ship."
"Give us some weapons, food, and other supplies and we'll do so gladly," Paddy Noon said.
The British captain agreed, and they made plans. Once the Brits loaded the Awful Knave with supplies they parted ways, the Knave heading to the coast of Cuba to meet the Spanish galleon, which, once they saw it sailing through Ovando Bay, impressed and intimidated them with its gargantuan size and majestic construction. They veered in their approach so that they would not directly face the galleon's broadside, lest its many guns fire upon them. As the Knave crossed the water the sailors spotted the other pirate ship, the Plunderer's Disgrace, approach a little farther away in the opposite direction. Without having said anything to each other the crew of the two ships knew that one intended to approach the galleon's stern and the other the galleon's bow. The galleon itself saw what the pirates did and began to turn to get its enemies within view of its guns; and so all three ships spun, with the galleon like the rotating sun and the pirates like revolving planets.
This passed for hours, with the pirates approaching slowly until finally, in the late afternoon, it became apparent that they would in fact converge. Most of the pirates, including Jacob and Henry, gathered their weapons and prepared to storm the galleon's deck. They sailed within 500 feet, 400 feet, 300 feet -- they could see the eyes of the galleon's sailors -- 200 feet, and then within seconds they bumped right into each other. Pirates from both ships stormed onto the galleon as planned and totally overwhelmed the crew. Henry and Jacob, armed with machetes and guns, climbed side-by-side along with the other pirates. With very little fighting they all seized the galleon's captain and won the crew's surrender.
They looted the galleon of its treasures, vast loads of Peruvian gold and silver, and as the pirate captains oversaw the equal division of it between themselves Jonny Skewers told Paddy Noon, "While we are here you might as well return Henry to our crew. I had in my mind to avenge you for your theft, but today's success has me in too good a mood."
"You can have him," Paddy said. "He trained our pegboy Jacob and we'll be fine with him now. He's a special fellow."
"I know. Did you get a gander of the galleon's pegboy?"
"You mean that giant octopus they keep in a tank? I shudder to think of men arousing themselves with that thing. It's unnatural."
Jonny was silent.
Once they finished sorting the loot the captains looked for Henry, but he could not be found. Neither could Jacob. But then in the process of searching the three ships some of the pirates noticed that one of the galleon's rowboats had gone missing, and when they finally turned their eyes to the sea to look for it they saw it lying empty on the beach of the Cuban coast.