Raise the Jolly Roger
Chapter 1

Copyright© 2014 by harry lime

Erotic Sex Story: Chapter 1 - A defenseless merchant ship. A stalking pirate ship loaded with merciless bandits. Six females all nubile and ready for whatever the future holds for them.

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Mult   Consensual   NonConsensual   Rape   BiSexual   Heterosexual   Fiction   MaleDom   Spanking   Rough   Humiliation   Group Sex   Orgy   First   Oral Sex   Anal Sex   Masturbation   Petting   Sex Toys   Cream Pie   Exhibitionism   Voyeurism   Size   Public Sex  

We had been making fair to middling speed catching a southwesterly wind coming up from the direction of the Dry Tortugas. The passengers were just coming up on deck even though it was almost mid-day. They were a motley bunch with a couple of Frenchie's in the mix as well. The Robinson family was out in full force including the maid Molly who had been doing her best to make the rounds of the entire crew before the trip was over. The four Robinson daughters were bouncy as usual but totally snobbish with the crew and even the officers onboard the ship. The captain was in his cabin just as he had been for several days down with some Island bug that made him a bit delirious and off balance unable to perform his duties. The first mate, Mister Jones was in charge and he was constantly going to the front of the line in poking the playful Molly taking it as a perk of his position. The girl certainly didn't mind because he had a fine cock that was envied by most of the ship's members.

Our ship's name was the Pride of Portsmouth and we took great pride in manning this sleek vessel with high riding draft and steady keel. My name is Grace. My last name is not important but for purposes of clarity I will disclose it as Goodman. I fill the position of cabin boy for the captain and it is a bit of a lark for I am actually a girl not a boy. Of course, only the captain and his sister Agatha were aware of that fact and they thought it was great fun convincing me that I would be quite safe under my Uncle's protection in his very own cabin. Unfortunately, his illness had forced me to vacate the cabin and I was currently taking shelter in the rope locker at the base of the bridge until he recovered. None of the crew had bothered me and I was thankful for the presence of the fair Molly and her greedy slit always ready for action whenever required. Sometimes the cabin boy was an alternative substitute for a plump little female and I was much afraid of being bent over by some desperate sailor in need of relief. It was extremely lucky for me that the ship's stores of spirits were safely locked away in the compartment behind the captain's quarters.

I had only recently passed my eighteenth birthday and the ways of men were still a mystery to me although I had been introduced to the art of using my hand by the elderly parson who tutored me in the learning of making music with my throat. He was forever playing with my tongue and my lips making me make this shape and that telling me to suck his finger as hard as could because it built up my lungs for the singing of religious tunes on Sunday morning. He had given me the assignment of learning the rhythm of the songs by the stroking of his staff with my two hands as he tapped my head with his hand to give me the exact beat he desired in my ministrations and in my song.

I am not so silly that I didn't know what he was doing was wrong but I really didn't make any fuss because I considered it a great opportunity to learn the ways of men's shafts. I was able to gauge the length and the girth and to discover what strokes made it react with the desired result. I judged I was doing an excellent job because the old fellow usually fell into one of his convulsive fits with my hands wrapped around his private parts and he sprayed his juices into my hanky held over his tip for purposes of genteel disposal of the sticky residue. He encouraged me to cover his thing with my lips on several occasions but I was reluctant to do so because I feared the possibility of coming down with child. He laughed at my refusal telling me,

"You silly girl, you can't get a baby that way. You have to spread your legs and take it in your slit as deep as possible."

I suspected he was telling me the truth but still I didn't want to take any chances and only allowed him to use my hands for his pleasure. In my role as cabin boy, I had carefully bound my breasts even though I only had a pair of bee stings of nipples and no lush roundness of most female persons at that age. I think it was because I had taken to the drinking of water rather than milk or cream and my figure was definitely more boyish than girlish.

I sat at the stern looking back at the ship that had been shadowing us for the past few days taking a leeside tack and keeping clear in Bristol fashion with a shy approach that was almost feminine in its nature. It seemed a bit smaller than the Pride of Portsmouth but it had more sail and looked solid in the rear suggesting it carried more than the usual number of gun-mounts for merchant trade.

The four Robinson girls were cavorting on the main deck. The eldest, Patricia was the beauty of the pack with golden tresses and blue as the sky eyes that seemed to brim with tears when the wind got brisk. She sported a magnificent cleavage that promised the pleasure of hidden nipples and full breasts that would fill any man's palms or mouth. It was difficult to determine the shape of her rear-end because of all the clothing but when she bent over to pick things up from the deck the curve of her buttock stood out like a tempting beacon of hidden promiscuity. It was a wonder some of the crew were not openly whacking off just ogling her juicy behind.

The second girl, Rebecca was only a year behind Patricia at nineteen and she was admittedly a bit overweight but her youth and pretty face compensated for her generous behind and her plump underarms. She smiled more than any of the other sisters and constantly wetted her lips with an interesting tongue that danced a pretty tune when she was thinking secret thoughts not entirely appropriate for a decently raised young lady of society. It was no secret that Rebecca was Molly's favorite and on most nights during the cruise, she would be in Molly's bed spooned up tight against her letting the rocking motion of the ship relax her into a satisfying release. The other sisters were envious of Rebecca's needy clinging but allowed her to take what she wanted because were all a bit standoffish of common folk. Rebecca was the only one of the four girls who would smile at the crew with a hint of a promise in her look that fired up the men's juices and magnified their opinion of their prospects.

The last two girls were identical twins, Letty and Lottie. Since they generally wore the same outfit, it would be difficult to tell them apart. In fact almost impossible until they spoke because poor Lottie was the unfortunate owner of a stammer that sometimes sounded like a machine gun when she got truly excited. The girls were eighteen and both virgins unlike either Rebecca or Patricia who had taken young studs as partners one spring day behind the barn after a long ride that had them both sweating and lusting for the real meat of a male shaft between their legs instead of the gliding muscles of a handsome steed. They did it side by side and even switched partners just to see if one was better than the other. Rebecca had a wonderful orgasm with both of the lads but poor Patricia wondered why this business was touted as being the best thing that could happen to you when all she felt was uncomfortable under their weight and disgusted with their fumbling efforts. She was determined to experience real "Romance" like a girl was likely to get in Paris or someplace other than behind a dirty barn with smelly animals.

Rebecca had gone on to sample several different young men and became well-acquainted with the ways of male dominance finding it quite suitable to her nature. Patricia was certain she would not find a proper partner for the game of romance anywhere in her father's manor so she fell back on the use of her favorite pillow with the rough tassels that rubbed deliciously on the insides of her legs when she rode it to happy conclusion.

The two younger sisters, Letty and Lottie remained fairly ignorant of male needs for companionship but they giggled just as hard pretending they knew all about the mysteries of sexual relations when neither of them had actually touched real male equipment. Their mother just assumed they would find out about it all at their own pace just like she did after she got married.

Grace was flat on her tummy watching the ship closing behind them. It was a lot closer this mid-day than the day before and she could make out the edges of the sails and the thin lines of the rigging that seemed far more complicated than their own. It looked like the other ship was making a go at passing them on the leeward side. That puzzled her because she knew enough of naval practices to know that was not a safe maneuver even in seas this calm. She didn't see the first mate, Mr. Jones anywhere on deck and she figured he was probably below slamming Molly up against the bulkhead trying to anchor her pussy on his oversized cock. She had wondered what it would feel like to be speared by Mr. Jones because she had seen him in the shower more than once and even in repose his prick was quite impressive to a young virgin girl who had only squeezed a cock between her hands and never between her legs.

The young cabin boy who was really a girl stole down to the captain's quarters and stealthily removed the spyglass from the case making her way back up to the stern to steady it on the rolling rail. She focused in on the deck of the other ship and saw that the crew was in some sort of dance or jig drinking from a huge wooden barrel that was obviously filled with spirits of some type. It certainly didn't look like a ship of the line or even a merchant ship with well-behaved crew. She didn't see any females at all but that was really not unusual out at sea where women were considered unlucky and even a jinx that might doom an entire crew.

One of the crew crept up behind her and sat on her haunches like a silly boy at play.

"Get off me, you great oaf, I'm trying to make out that ship that's following us."

Grace made no fuss about her backside being rubbed by the boy's hard cock because she knew it might draw attention to the fact she was a girl and not a boy. She allowed the perverted thing to ride her until he grunted in joyful release feeling the tingle he desperately needed. Grace had no problem with such foolishness because it was just a form of friendly interaction between two young lads in the prime of life. He laughed and ran back down below when the cook's voice rang out calling his name.

She got back to her spyglass and thought for a moment she saw the dreaded flag of skull and crossbones known as the "Jolly Roger" pop up in the center of her glass like a signal of danger. She steadied the glass and waited and almost immediately, the same flag crossed her focus and it was whipping in the wind like an omen from the devil's lair that they were about to meet up with real-life pirates and were all in danger of their lives and loss of all their possessions.

The young girl wanted to run straight to her Uncle and warn him but she knew that would go no good because he was so far under the weather that he would probably not understand a single word she was saying. The first mate was also out of the picture because he was most likely still pumping away on Molly's hindquarters. She went instead to the Quartermaster, Mr. Adams and blurted out her news without pausing for a single breath.

The older man looked at her and just shook his head. She was bewildered because she felt they were on an irreversible course and headed straight to Davey Jones locker.

"It is all right, young lad, nothing we can do now. I tried to tell the first mate the day before yesterday of my gut feeling we were being stalked but he is a headstrong lad. We just have to make do with what happens and hope these pirates are not part of the Blackbeard ilk or we will all be walking the plank before the sun goes down."

Not know what else to do, I just ran back to the rope locker and locked the door hoping for the best outcome possible.

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