Your Daddy was a Pirate

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Forced Group Sex and Debauchery on the Spanish Main.
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SlyDog969
SlyDog969
574 Followers

It was a fine ship originally built by the French; I was the first mate when we captured her four years ago and refitted her with extra sails and 16 cannons to make her fast and just as deadly as any ship the French or Spanish could throw at us just short of a ship of the line.

I ascended to captain after our previous captain was killed in the hand-to-hand fighting. I did like the perks of being captain but not the responsibility and constantly looking over my shoulder to see who would try and kill me to get my job. Since I come up through the ranks starting as a cabin boy all the men respected me and followed my orders as long as I kept their pockets filled with plenty of gold for buying rum and whores when we were in port.

I had my own special whores I liked to visit at Port Royale and Tortuga being the Captain with a Captain's share of the loot I could afford women with special talents that knew how to keep me coming back sometimes bringing as many as three or four women into my bed at a onetime just because I could afford it and to impress the other captains and their crews.

I have a lot of respect for whores and prostitutes, women who go out whoring at night or just trolling for a one night stand they are basically female pirates of the street looking for a male treasure ship they can pillage take what they want from and then leaving him as a burning hulk, sailing away looking for their next target. That's why men like me are always looking for women like that.

We had been sailing around the Florida straits three days out of Tortuga when the lookout at the top of the main mast spotted a sail on the edge of the horizon. A few minutes later he screamed it was a Spanish galleon with all the fancy sails and trimmings. Bloody Spanish are such arrogant little bastards strutting around like peacocks making themselves easy targets.

I hate the Spanish, even though my men would squander away all the gold and loot we captured on rum and whores it was still better than letting the Spanish take it back and give it to their Catholic Pope who would use it to finance the inquisition for the torture and murder of innocent men women and children throughout Europe. In our own way, we were doing God's work or a least doing a lot less damage to God's children they were.

It took us almost 3 hours to catch up with them and after 10 minutes of exchanging cannon fire, they lowered their flag. Two of our cannon shots had hit them below the water line and they were taking on water nothing that could not be repaired but I was not going to stick around. I order the men to transfer the gold and other loot to our ship. I went below to see what kind of cargo they had. They had four large chests full of gold and silver and another with a decent assortment of jewels.

In the corner of the cargo hold was six large 5-foot tall jars. One of my crew cried out "Look at this captain pickled Spaniards." I had seen this many times before, the Spaniards who die here in the new world that is married were sent back so that their Catholic whore wives could prove that their husbands were dead and could get remarried in the Catholic Church. "Toss those damn things overboard send them to the bottom of the ocean" I ordered.

As I returned to our ship my men had already transferred the gold and female captives so I gave the order to cast off the galleon and set sail. We were well away from the other ship and under full sail riding the currents of the Gulf Stream with a heading of north by northwest with a southeast wind to our back. We had a good wind, light chop on the ocean and a good haul of loot, not bad for three days out.

I walked down into the dimly lit belly of the ship were the captured women were lined up and ready for my inspection. The stripping and showing of the wenches before drawing lots' to see who would have them first was a time-honored tradition aboard most pirate ships, it was something I had always looked forward to in my younger days.

I remember losing my virginity when I was just a cabin boy; my first captain bought me a very experienced older woman to teach me what every good sailor needs to know about women. The captain went off and got drunk and forgot about me for about two days. The older woman didn't kick me out but rather took advantage of my youth and used me when she wasn't serving the other men that came and paid for her services.

She gave me a complete education and some carnal pleasures that no woman has ever been able to give me since. I still have a preference for older mature women because of those memories of her, vivid and fond memories even more so than that of my own mother.

As I descended down into the cargo hold of the ship, the captive women were standing there with their hands tied behind their back; their dresses had been ripped down to their waist leaving their breast on display. They were a fine looking batch of Spanish whores not an old hag in the bunch.

As Captain, it was a tradition for me to review the catch and provide any comments and any suggestions on how to best use them based on my many years of experience. Two of the serving maids were young and caught my attention and I commented on how firm and nicely shaped their breast were and that they would be perfect breeding whores if anyone was thinking about having a crying baby.

I made my way down the line stopping to grope each one and comment on their body and who would be best for which sailor. The first two noble women did not impress me, they were not all that unpleasing to the eye but my contempt for them and theirs for me was quite evident in the glares that we exchanged. The third noble lady was very different, she showed the same contempt as the other but I had a strange feeling about her. She made me uncomfortable just being in her presence for no good reason that I could determine.

I didn't know it at the time but her name was Sonja named after the pink rose very rare and very beautiful she was one of three noblewomen along with four serving maids. Her beauty was somewhat tarnished from the ordeal of the battle and being manhandled by my crew fetching her onboard. She was proud and defiant, I smiled I had seen her kind before. She had managed to fight off the attempts of my men to take her wedding ring or the silver cross around her neck.

I told the first mate to move her off to the side I was going to have her for myself something I did from time to time just to show the men that I was the captain and in control and could have my pick of anything on this ship. Since there were six other women for the crew to fight over and ravage I knew there would not have any objection. Sonja was covered up and carried over to the corner like a special cargo tied up sitting in shadows.

I had not participated in the deflowering festivities myself since I became Captain but I did always stay around to make sure the men did not damage the merchandise in their unbridled enthusiasm. I made them remove the dresses without damaging them any further since the woman would still have to use them as cloths until we returned to port. They were now standing completely naked in the dim light waiting to be devoured by their captures'.

"Have at it boys they're all yours," I exclaimed.

Each woman was carried off into different corners of the cargo hole with three to four men forcing them along the way occasionally falling down and then pulled back to their feet.

It was always interesting to see how differently each group would approach this process.

My first mate Bart was of mixed race, his father had been a pirate, an Irishman I think and his mother was a black slave woman his father had bought from a sugar plantation and he made her his wife. Bart was big and strong as an ox I knew the first time I saw him I wanted him with me and not against me so I made him my first mate so he could watch my back. He was ten years younger than me and not ready to be Captain so I knew I could trust him at least for the time being.

Bart was big in more ways than one, and when he took his turn at these group activities it was always curious to watch the reaction of the other men and the eyes of the female about to be taken. The rest of the crew would usually give him first shot at the women and just watch in awe as he performed like a prize bull brought in specifically for his breeding prowess.

The woman Bart and his group had chosen were one of the servants. She was a little thick in the hips with the largest breasts of the group. You could tell she was the one who had been doing all the physical labor of the group and with those hips; she was the one who was best suited for all the manhood that Bart had to offer.

The other captive women had fought it struggling and fighting their assailants, but not this one she was defiant in every way almost challenging Bart to take her and to prove how good he was. Her action made it clear this was not her first time with a man and she was ready for anything he had to give her.

She began calling him names in Spanish, dirty nasty names which he didn't understand but made him want to fuck her even more. This woman definitely missed her calling as a whore she was riding him and using him just as much he was using her. When he was done and he rolled off her, her gaping pussy was stretched so wide you could sail a frigate through there. She sat up on her elbows surprisingly looking none the worse for the wear. She frowned at the other three men standing around her with their significantly smaller penises in hand and she grunted something about Jesus in Spanish then lay back flat on the floor waiting to see who would be next.

Over near one of the gun ports another group was busy with their prize bent over one of the cannons.

Jimmy McNeil was a gunner mate the older and more experienced of the group. Bob and Tom were seaman third class that had only sailed with us once before. All were highly focused on their task at hand of ravaging their assigned Spanish slut. They had taken one of the noble women; she had 5 or 6 names that nobody could remember or pronounce so they just called Countess Catalina.

Tom squeezed her nipple roughly as she squealed and then began to cry.

McNeil shocked by her loud shrills reacted by pulling out a knife. "If you scream, I will cut you." He said in a stern voice. "Get on your knees." She was shocked by his threats and immediately complied.

"Who wants to go first?" McNeil asked.

Tom stepped up, "I will." as he loosened the drawstrings on his pants and she gasped at the size of his dick. "If you bite me, I'll knock out all those pretty teeth."

Tom put his dick to her closed lips. "Open up." He slowly forced it in where her tongue was so warm and wet. "Ahhhhhhhhhhh..." he began pumping into her mouth. There was too much build up so it wasn't gonna last long.

She began gagging on his cock. "Use more tongue," he yelled as he rammed deeper into her throat over and over again until he shot cum down her throat. "Swallow it," he said as he kept pumping.

"Whew," Tom pulled out satisfied. "That was so good."

Tom looked up to see Bob and McNeil both with their dicks in hand watching anxiously. As Bob approached her face, "My turn," he said. As he pressed his dick to her lips, tears were running down her face, McNeil got on his knees next to her and began caressing her ass while jerking himself off.

"Oh wow, she's so wet." He had a finger in her pussy and began twiddling her clit with his thumb. She breathed heavy as Bob took advantage of her mouth, pumping wildly and gagging her over and over.

"Let's bend her over the cannon so I can fuck her while she sucks you off."

They moved her while she kicked and offered up her best resistance. Tom held her down while Jimmy toyed with her clit and Bob kept fucking her mouth. Then he noticed that she was moaning. Her body was uncontrollably responding to the way McNeil was working her clit even as she made every effort to resist.

"Oh fuck, I think this slut is going to cum!" Jimmy exclaimed moving his fingers faster and faster. He began positioning himself behind her and as a moan became a shriek as he rammed his dick deep into her with one swoop and she came hard on his cock, tilting her head back to yell out in passion.

McNeil rammed and thrust deeper and deeper into Catalina's tight, warm cunt as Bob came hard in her mouth. She gagged as he filled her throat with his seed.

I stepped closer to see McNeil's dick entering Catalina's vagina. Bob was fucking her face with McNeil in her cunt. The whole thing was arousing me.

As Bob finished and they lay in a spent pile, Tom was clearly ready for more.

"Ok boys, my turn again." He said with a smirk. "I'm going to take that ass."

"No, no," Catalina cried. "Not my ass, please, please fuck my pussy again, but please not the ass."

"Oh puta, don't worry, we will take your pussy again but first that ass is mine."

"Please no", Catalina whimpered but Tom didn't hear her. He looked at her naked body sprawled across the cannon. It was even more sexy with her tits so big and firm hanging down swaying back and worth.

Then Bob intervened, spreading the cheeks of her ass nice and wide so all could see her puckering asshole winking at him. Tom needed it now. Bob stepped back as Tom pressed his dick against the warm opening. It was so tight and she was fighting him.

Tom couldn't get it past the tip, he needed lube. So he rubbed his cock on her wet pussy and slid it in a few times to lubricate it. It shocked him how tight it still was after that fucking McNeil gave her. He could almost lose himself in there until he remembered; he wanted a tighter hole and that round little Latina ass.

Tom pushed again against her asshole, this time getting more than halfway in. She was so tight and fighting it. He could feel her ass tightening and loosening repeatedly around his shaft.

"The more you fight it, the better it feels," He groaned.

Tom went back to the pussy for more lubrication and then rammed hard into her ass, getting all the way inside. "Oooooh...Oooooh...Oooh..." He exclaimed it was the best feeling on Earth. He was now balls deep in Catalina's ass. He pounded her and pounded her. We heard his balls slapping her repeatedly.

Apparently, he wanted Catalina to enjoy it too so he reached around and began rubbing her clit again as he fucked her ass. He rubbed his other hand all over her soft body that appeared to be yearning for it as he twisted her nipples and pinched them hard.

"No, No, Stop," she cried but started breathing heavier as his fingers moved faster along her clit and then slipping two fingers inside her. I could tell she was loving it as she started pushing into his palm and grinding back on his dick. "No, no, no..."

"You keeping saying no but I think you like it, slut. I think you're going to cum," he moaned even though he was holding back Cumming inside her trying to make it last as long as possible. Her ass just didn't loosen up, it kept being so tight and kept tightening and loosening around his cock. He commented that it was just so warm and tight.

He fucked it and fucked it until he felt her cum on his hand; he said he could feel her cunt twitching all over his fingers and soon after he came in her ass.

He looked like a melted puddle as he lay on top of her. She cried and sobbed, still twitching from her orgasm.

"Oh, someone liked that, didn't they?" he taunted her.

Her trembling voice said no as she cursed him Spanish but the look in her eyes and the uncontrolled convulsions from the aftershock of her orgasm told a different story.

"I guess it's our turn then," said Bob. "I haven't fucked her yet." Tom looked around to see Bob and McNeil standing there with erections again ready to take their turn at the pompous little Spanish wench.

I looked over at Sonja in the corner observing her shock and amazement at all debauchery that was going on around her. I wondered if she appreciated the fact that she been spared all this because I gave her a reprieve.

I had been watching long enough and decided to take Sonja back to my cabin and have my own share of the booty.

I pulled her up the stairs to my cabin all the time rambling on about how good I was at sex and what I was going to do to her. As I tossed her across the threshold of my cabin to my amazement she responded to me in English. It was clearly not her first language but she spoke it better than half my crew.

I tossed her on my bed and she began screaming a tirade of obscenities waving her hands around like she was swatting flies. My Spanish was not very good but I did know all the bad words and she used all the ones I was familiar with a few new ones that would make the whores in Tortuga blush.

She eventually switched back to English calling me an infidel and announcing that I would suffer the wrath of God on my unholy pagan soul. I called her a heathen Catholic that wouldn't know God if he came up and stuck his dick in her filthy Spanish mouth. I then informed her I didn't bring her up here to talk.

"I would rather you kill me" she screamed with a dramatic look of indignation on her face turning away looking up as if I wasn't even there.

No, you are worth more to me alive than a dead princess and I am sure whatever pencil dick little Spanish troll you are married to will pay a lot of money to get you back even after I give you a sample of what a real man can do with you. Also, let me remind you if I am not pleased with you I can always escort your highness back down to the cargo hold and let the rest of my crew show you their idea hospitality.

"No," she said. "But I will still resist you like any proper lady of the Spanish crown should do."

"I notice you didn't mention your husband there Countess, does that mean you're not going to fight me off for his sake?"

I stepped back and told her that if she cooperated I would try not to be too rough on her, but if she resisted or tried to fight me it would very painful and I would still get what I wanted.

I pulled her dress off her and then tied her hands to the post on the bed. I fasten her to the straps I positioned at the four corners of the bed. I enjoyed seeing her spread eagle naked and tied to the bed as her large firm breasts heaved up and down. Her nipples erect with anticipation as she feigned being scared and as she wiggled the best she could trying to free herself.

"Stop struggling bitch and I might not hurt you!" I barked in my deepest most manly voice as I maneuvered her so I could spank her ass. "You're going to like the feel of my big cock deep inside that sweet little Spanish pussy of yours."

After inflicting a few good hard slaps on each cheek of her pale white ass that undoubtedly had never seen the light of day I then shifted my attention to her very ample breasts.

"My, my love, what a nice set of tits you have. I bet your Catholic priest really like to gaze at those breasts when you bending forward and sticking your tongue out to get your little wafer at mass."

"You Godless bastard" she screamed. "I hope you rot in hell."

I leaned down and took her right nipple into my mouth. I start licking and sucking on it making it hard. I repeated my actions with the left nipple. As I was sucking one I would pinch and twist the other nipple.

When I bit down hard on one of her nipples, she screamed. I asked her if she wanted to be gagged. She shook her head no.

After playing with her nipples for a few minutes she screamed "No" and started thrashing around trying to free herself again.

Instead of slapping her face, my hand came down hard slapping her right breast. She still struggled so I slapped the left breast, then the right one again.

She was still struggling but not as much. I stepped back and looked at her once again. As I was admiring her body I asked if she like that. She told me No, I then asked her if she ever fantasized about other men besides her husband, men with big dicks like me.

SlyDog969
SlyDog969
574 Followers