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In 1492 Columbus sailed the ocean blue. Ever wonder how much cocksucking and fucking went on during those long ocean voyages back in those days? I’m sure men were just as horny then as now.

Horny men confined in close quarters for long periods. There had to be a lot of cum spilled. With no women available, a warm wet mouth and/or tight arse would have to do. Don’t you think? I would.

This could have happened.

The Serendipity sailed out of Plymouth, England one fine Spring day in the year 1759 with load of tea bound for the Colonies in America.

The ship was commanded by Captain Gerry McGuire with a crew of 49. Over half were seasoned seamen, with the remainder less experienced but high on the idea of seeing the new world.

No one was more excited at the prospects than sixteen-year-old Cord Haslet, the cabin boy and servant of Captain Gerry.

Captain Gerry was an experienced skipper having made two trips around the horn of Africa to India and China. This was his third trip to the colonies. He would carry tea to Boston and then sail down the coast to Virginia and take on a load of tobacco for the return trip to England.

Ever since Sir Walter Raleigh introduce tobacco to England in 1586, The East India Company combined their tea trade from China with tobacco from Virginia as a very profitable enterprise.

The East India Company rewarded Captain Gerry with command of the new ship Serendipity making its maiden voyage to the Colonies.

With fair weather and good winds, the trip should take about two months to reach Boston.

Captain Gerry was a highly sexed married man with three daughters in Plymouth. Each time he returned from a voyage, he would fuck his wife sore and leave her pregnant when he left on his next trip.

Each trip, Captain Gerry would pick a select few from the crew to bugger from time to time, thereby, satisfying his carnal lust.

He was especially pleased with young Master Cord Haslet and had personally selected him for this voyage. Little did Cord know of what would be expected of him while personally serving the Captain.

Cord was a slim lad with dirty blonde hair and very fair complexion, which would soon tan to a golden bronze color. All of which made him very attractive to Captain Gerry.

A week out of Plymouth, Captain Gerry was feeling a growing need and summoned young Cord to his cabin. Cord knocked and waited for the Captain to tell him to enter.

“Come in, Master Haslet,” the Captain said.

Entering the cabin Cord was completely startled to find the Captain in a complete state of undress. His manhood was hard and sticking up lying against his abdomen. “Eh, sorry sir I can come back later,” Cord said.

“No, no Master Haslet, do come in and close the door,” responded the Captain.

“There are certain duties you are to perform for me that have yet to be explained. The first is you are to perform fellatio on me. Do you know what that means?” Asked the Captain,

“Er, no sir,” Cord responded.

“Put quite simply, you are to suck my cock and accept my load of cum in your mouth, which you will promptly swallow. Do you understand.”

Cord was dumbstruck and could not respond.

“It is a service you will provide for me from time to time, and when the time is right, I will take you to my bed and bugger you. Do you now understand Master Haslet?” The Captain asked.

“Bugger sir,” Cord said.

Yes, I will fuck your arse,” the Captain said.

A stunned Cord was speechless and weak in the knees not knowing what to think.

“Now Master Haslet come here, get on your knees and start sucking my cock,” said the Captain.

Slowly moving to the Captain, Cord sank to his knees. The Captain’s hard cock was now at eye level.

“Take hold of my cock and put it in your mouth,” the Captain said.

Doing as he was told, Cord took hold of the Captain’s cock with both hands and placed it on his lips. As his mouth opened, the Captain pushed his cock inside.

Time for pleasantries were over, The Captain grabbed Cord’s head and pulled it down on his long hard cock till it hit the entrance to Cord’s throat, causing him to gag.

The Captain began fucking the boy’s mouth like a pussy but careful as to not cause him to choke and gag. The warm wet mouth felt so good, but the Captain was forced to admonish Cord to watch his teeth.

It had been a week since the Captain had found release and cumming in the lad’s mouth was going to be a pleasure.

Cord had never sucked a cock so was totally inexperienced, but he was catching on quick and found he actually enjoyed it. He could feel the Captain’s cock begin to pulse just before he plunged and held letting loose a copious amount of cum coating the boy’s tonsils.

The torrent of cum caused Cord to begin choking and the Captain bellowed, “swallow boy swallow.”

Cord did as he was told and then savored the taste of the cum residue finding it a somewhat salty and bittersweet, yet not at all unpleasant. It was only then that Cord realized his own cock was hard as a rock and had been leaking cum. Later he would masturbate and find his own release.

Over the next couple of weeks Cord would become quite addicted to the taste and flavor of the Captain’s spunk. Cord was a quick learner and was developing into a very good cocksucker, much to the Captain’s delight. He would suck off the Captain daily.

But on the third week of the voyage, the Captain informed Cord it was time for him to get fucked. He was ordered to get himself undressed and to get into the Captain’s bed. Once in bed he was ordered to get on his hands and knees. The Captain joined him in bed getting behind him as he was about to mount the young lad from behind like a beast in the field. The Captain was about to use his favorite position when fucking his wife.

Cord could feel the Captain’s hard cock probing around his anus, and then with a thrust, the head of the Captain’s cock entered Cord’s arse breaking past the sphincter muscle. Cord felt a very sharp stab a pain and gave out a loud squeal. The Captain paused for a moment to let the pain subside before slowly beginning a fucking motion with each stroke going deeper until he was balls to the wall.

Soon the pain was replaced by pure pleasure as the Captain’s cock was giving Cord’s prostate a wonderful massage. Cord’s own cock was rock hard and leaking cum just like when he sucked off the Captain. But this time something wonderful happened. As the Captain was deeply plowing his arse, Cord experience a fantastic orgasm, better than any he ever had while masturbating. This sent the Captain over the edge and he blasted a huge load deep into Cord’s bowels. The well fucked Cord collapsed on the bed.

For the remainder of the voyage, Cord would alternate sucking off the Captain and offering up his arse to be fucked. Both the Captain and Cord were well sexually satisfied.

The Captain had become very fond of Cord and began thinking of him as a potential husband for his oldest daughter. Cord had grown into a very handsome and strong young man capable of producing many fine grandchildren for the Captain.

After their third voyage together, the Captain took Cord to his home and introduced him to his daughter Abby, a plump rosy cheeked lassie of sixteen.

Cord was immediately smitten by the lass and she was just as smitten with Cord. It was agreed they would be married following the next voyage. The Captain once again left a well fucked and pregnant wife.

Little did the Captain or Cord know they were also leaving a very pregnant Abby.

During the voyage Cord would often wonder how Abby had become such an accomplished cocksucker and how she knew all the tricks she taught him while they were fucking.

He never had the courage to broach the subject with the Captain.

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(This is a work of fiction, made up in my mind, any resemblance to actual events, or people, or another author are strictly coincidence. This is an original work. -JW)At some point or another everyone has a fantasy about having some amazing sex with some complete stranger in the heat of the moment. The following can be filed into that category.I have never considered myself to be one of the beautiful people. I am more along the lines of the guy who lands in that group below the top rung of...

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Preface: This is my first story. All kind of comments are welcome. This is an Indian story and has a few lines in the local language and a few regional words. Intro Riya looked at her reflection in the mirror and let out a deep breath. The makeup girl was giving the final touches. . Her face was adorned with jewels. A big nose ring which touched her red pouty lips. A maang-tika which sat perfectly between her brown silky hairs. Big dangling jhumkas decorated her ears. She looked...

Serendipity 8211 Part II

Hello folks!! Wish you all a very Happy and Prosperous New Year. Well I’ve been reading the stories uploaded here for quite some time now and I’m glad that people are willing to admit their most intimate secrets via ISS. I’ve also something to contribute, hope you readers have nice time reading and enjoying the moments and all those hot and horny ladies out there, let me tell you I’m all yours you can mail me at , I promise you won’t regret it. To begin with, I’ve always been attracted to girls...

Serendipity Part I

You know my friends used to say I was a real bad ass in high school. Probably cause of all the times I used to fight any one who crossed me or cause of the way I'd always smart off to the teachers. I tell you that so you can get a better understanding of the story I'm bout to tell you. It was my Senior Year. And I was flunkin' only one class (surprisingly). It was English. Ms. Hannah was the teacher. And man, she was a blonde bomb shell. She musta stood at least 5 foot 9. She was 36 years...

Serendipity

I’m not a voyeur. No, really, I’m not, but when fate drops something into your lap, as it were, I would be a cold fish to walk away, don’t you think?Quick backstory. It was my final year at University, and I was in a house-share with another male and three females. We all got along well with each other and lived separate existences as we studied different subjects.One weekend, both Alan and I had planned to be away visiting family and he duly disappeared on the Friday evening. I left early...

Coed Serendipity

We see an attractive girl in her dorm room, studying at her desk. She’s wearing a t-shirt and sweatpants. It’s nighttime and the shades are drawn and all of the lights in the room are on. She finishes and puts her pen down and closes her book and puts it on a shelf. She turns off the desk light, stands up and pulls the covers down on her made bed. She walks to her closet, takes off her t-shirt and bra, and puts them into the laundry basket. She takes a lacy, white nightie off of a hangar and...

Serendipity

It all started when my husband came home in a blue dress. My name is Kim. I'm a forty-something housewife living in suburban America; Sunday church, bible study. I have a daughter named Stacy... I think you've met her, everyone has. I'm easy to spot at PTA meetings as I'm the short red head with long skirts, peter pan collars and low heeled shoes. My husband Ron is a cowboy wanna be - he looks the part but he's never riden a horse and I seriously doubt has ever eaten a bowl of chili. I was on...

Serendipity

John Offen Peter Finch. What a crazy name to give to a child. He hated the name and hated it even more as he got older. The other kids discovered that “Jack” was the nickname for John. Then the teasing never stopped. How would you like it if kids called you “Jack Off Peter” and you couldn’t argue back? It was his name. His last name wasn’t any fun, either. That is why he used his initials JP whenever he introduced himself. He could honestly say it was his name and preferred his friends to...

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