Agatha had always wanted to be a pirate.
First off, let me explain what this story is.
I’m inviting other erotic writers to show what they can do on my Substack page. It is part of my evil plan to take over the whole of Substack with erotica! If anyone is interested in being a guest, have a read of this and then DM me:
My fifth guest in this series is Joe Blow who takes a classic trope and makes it erotic and sexy. If you like gangbangs and free use whores you’ll feel a deep stirring…I should know!
Let’s start with a short interview…
Tell us a little about yourself…
I’m a 63 year old Australian man. I work in a library and spend a lot of my spare time reading and watching movies.
What are your stories normally about?
My stories are in the spirit of funny cartoons with sex scenes in them. Often they are genre parodies - horror, scifi, superhero or adventure stories.
What inspired you to write erotica?
At first it was a way of paying tribute to specific women on-line and then I started taking part in a twice weekly erotic writing challenge. I like to make people laugh, but I have a hard time coming up with plots which aren’t based on my varied sexual fantasies.
How much of what you write is from lived experience?
Nothing is from my experience. I have less experience than most, but the things which happen in my stories are generally fairly far from anything which has happened to to anyone. Imagination, not realism, is my strong point.
When Agatha the milkmaid saw The Libertine sail surreptitiously up Blood River and disgorge it’s motley band of renegades, she knew that this was her chance. She was an inveterate reader of pirate tales who longed to walk the swaying boards of a stolen Spanish galleon bound for the West Indies, there to prey upon the Queen’s merchant ships like a wolf upon the sheepfold.
She longed to feel the ocean spray in her face as she clung to the wildly swaying crow’s nest, scouring the horizon for billowing sails. She longed to drink rum that would burn all the way down her throat and turn her belly into a jolly furnace. She longed to sing sea shanties and swap filthy jests with horny sea dog’s who’d been at sea so long they were starting to have romantic thoughts about their parrots.
While reading her swashbuckling pot-boilers she had often wished she were a man. But no longer.
“A member of the fair sex I may be,” she told herself, “but if I can’t be a pirate, that’s unfair. And I’m going to bloomin’ well do something about it!”
That evening her dad sent her down to Davy Jone’s Locker, the favourite tavern of sailors, to deliver their daily pitcher of milk. There she made a strange request of Saucy Sally the bar maid.
“They be pirates right enough,” Sally told her. “My port will be well occupied for the next few days.”
“Could you steal some of their clothes?” asked Agatha. “I’ll pay you handsomely. I have some savings.”
“Why would you want the sweaty rags from some crusty sea dog?” Sally wanted to know. “Are you kinky?”
“I’ve decided to be a pirate,” Agatha confessed, looking Sally determinedly in the eye.
“A pirate? A girl can’t be a pirate!” Sally insisted.
“Anything a guy can do, I can learn to do!” Agatha declared.
“Where the equipment allows,” Sally conceded, “you may be right. But you don’t look much like a pirate.”
“I’ll have to present myself as a trainee cabin boy,” Agatha explained. “Once I learn to sword fight, I’m sure I can work my way up.”
“Do you know what those guys do to good looking cabin boys when they’ve been out at sea for months?” Sally asked, shaking her head.
Agatha hadn’t thought about that. The thought of her bum hole being buggered by pirate cock made her pussy get really juicy. But she would have to make sure that didn’t happen. If they got her breaches down her secret would be out.
“I won’t let them discover my sex,” Agatha assured her.
“You’re a fool, but a spirited one,” conceded Sally. “I’ll help you, but God help me. I’d never forgive myself if I heard that you’d been raped and thrown overboard for fish food.”
A week later, Agatha had a kerchief tied over her red hair, her breasts tied down tightly with strips of cotton and was wearing a sailor’s coat and breaches. She’d shoved one of her father’s socks down the front of her breaches to simulate the bulge of a cock. And she’d dirtied up her face. She walked boldly up the gang plank to The Libertine and approached Captain Bullfinch.
Bullfinch looked at her grimly through his one remaining eye, stroking his crusty black beard with his right hand.
“What is it lad?” he growled with gruff impatience. “Are you one of the crew’s bastard’s come to say goodbye to daddy?”
“No,” replied Agatha, putting on a convincingly masculine voice. “Sally from Davey Jone’s Locker sent me. Old Monkey Breath is in Newgate. He got caught exposing himself to the landed gentry.”
“Fuck!” cried Bullfinch. “He was a pain in the arse, but a fine sailor. Now we are one down.”
“If you were to press-gang me, I wouldn’t complain,” Agatha told him. “I may be young - barely eighteen - but I have spirit and I feel the call of the tides.”
“I’m a pirate, lad,” glowered Bullfinch, planting his peg leg firmly on the deck and pulling Agatha toward him by the hook he slid between the buttons of her jacket. “I could kill you and throw you over the side of the ship without thinking twice.”
“Yes, cap’n,” Agatha replied nervously.
“You know that, don’t you, lad?” he growled. “And yet you come to me and ask to be one of my crew. You have balls, boy! I can use a crew member with balls like that! You’re hired.”
Agatha was scared. This was reality, not some idle fantasy. But she was also exhilarated. She was a pirate!
***
Agatha used the name Roderick. She fit in well with the rest of the crew, and, in the first few weeks out at sea she really learned the ropes. She also learned the sails and the swabbing of the decks and a little sword fighting. And she learned how to swear like a sailor.
There were two problems though. She felt dirty and she felt dirty. Having all those manly pirates around her all day long, often shirtless, with the sun glistening off of their sweaty pectorals was making her horny.
But there was no way she could relieve the frustration. There was no privacy for wanking. Hell, every time she needed to take a shit or a piss she had to scream, “Mermaid off the starboard bow!”, pull down her pants, stick her bottom over the side and hope she could finish and make herself decent before anyone turned back around.
They were beginning to think this Roderick fellow was a bit loopy. So she was getting hornier and hornier, especially when her favourite pirate, Buck - a young chiselled Adonis with a neatly trimmed black beard - took his turn to bathe on deck. All the pirates took turns bathing on the main deck, standing naked and washing down their bodies with ladles full of sea water from a big barrel and a huge bar of soap. Buck had a huge cock and a really tight ass.
Agatha had been wearing the same pair of bloomers underneath her breaches for six weeks now and they were as crusty as a loaf of bread. She hadn’t thought about this problem. She couldn’t very well wash herself on board. She was feeling very mucky and the other pirates were laughing at her apparent hydrophobia and said she stank worse than a sperm whale’s shit hole.
Eventually, the inevitable happened. The captain ordered the crew to strip “Roderick” and wash “him” down.
“No! No!” Agatha protested. “I’m just shy. I’ll have a bath tonight after dark when no-one is around.”
“You’ll be stripped and swabbed like the ship herself,” insisted Captain Bullfinch, “and you’ll like it. Blake, hold him still! Buck, strip him naked!”
The game was up. There was no sense in resisting Agatha realised, so she let that dreamboat of a pirate unbutton her coat and remove her tunic.
“Why the binding on your chest?” asked Buck, beginning to unwind it. And that was when Agatha’s shapely boobs sprang forth and Roderick the pirate-in-training disappeared.
“Well, I’ll be horn-swaggled!” exclaimed the Captain. “It’s a girl!”
“Coooorrrrrrrrrrr,” growled the rest of the crew lustfully.
“I’m going to enjoy washing you down you smelly little wench,” smiled Buck, with a twinkle in his eye.
“We’ll all get a chance to enjoy her,” declared the Captain. “And then she’s fish food. We can’t keep a woman on board a pirate ship. There would be no discipline.”
“Wait!” cried Agatha, as Buck divested her of her boots, breaches and crusty bloomers, leaving her stark naked in front of the lustful eyes of the pirate crew, one hand across her pale freckled breasts and the other trying to hide her luxuriant conflagration of fiery pubes. “I’m serious about being a pirate. You’ve seen I’m good at shipboard duties and my sword fighting skills are improving. There were only two problems with pretending to be a man. One was I couldn’t have a bath. I’m really not a dirty girl. I like to be clean. And the other is that I was getting so horny being in the middle of such a crew of manly pirates and not being able to feel your stiff hot cocks in my cunt and my arsehole and my mouth. So now you know that I’m a girl, its not a problem, its a solution. Let me be the ship slut.”
“We won’t have to fuck each other any more!” cried Blind Drunk Pugh.
“Speak for yourself!” whined Orlando, fingering his diamond-encrusted earring.
“There are twenty three horny sea dogs aboard this vessel,” pointed out Bullfinch. “By the end of the first day you would be sore in every hole.”
“Well,” said Agatha, “you’ll have to let me share myself in a sustainable manner. My mouth doesn’t easily get sore and neither do my hands. Anytime any of you get stiff, I’ll get you off, that I promise, but you might each have to be satisfied with only fucking my cunt once a fortnight and my arse once a month. Does that sound reasonable? And I’ll keep myself clean. I can wash as often as I like now. I don’t have to worry about you seeing my naked body. In fact, as long as we are in these warmer waters, I’ll just stay nude. That’ll make it much easier.”
The pirates couldn’t believe their ears. By now, all but Orlando, had pulled down their breaches and were wanking their proud cocks. Even the Captain’s discipline had lapsed to this extent.
“Hey, boys,” laughed Agatha, realising her position on the ship was secure, “there’s no need to pleasure yourselves. That’s my job!”
Quickly she splashed the sea water over her naked body and soaped it up thoroughly, and when she got to her pussy she took the opportunity to wank it shamelessly while the lusty crew looked on.”UUuuuuuuhhhhhhhhh,” she groaned, releasing all the pent up lust of six weeks at sea with the sexy pirates in one body-shaking, cunt-squirting orgasm.
And then the orgy began. Agatha started a lusty rendition of The Good Ship Venus. The guys all joined in, which was a good thing because Agatha couldn’t keep singing once she had Buck’s huge prick in her mouth. Bullfinch declared Captain’s privilege, getting down on his one knee, spreading Agatha’s pale bum cheeks, lubricating his throbbing erection with spit and ramming it home up her tight virgin arsehole.
“Ouch!” she cried at this indelicate invasion, but soon she found that the pain was replaced by pleasure.
Meanwhile she had a crewman’s cock in either hand and was wanking them energetically. Horny as they were after six weeks at sea, it only took a couple of minutes for them to groan and quiver and spurt fountains of hot cum all over the deck and Agatha’s soft and loving hands. When this happened another pair of cocks would take their place.
“Being a slut is even better than being a pirate!” Agatha thought to herself. “And I’m the luckiest girl in the world because I get to be both! I get to be a pirate slut!”
***
Life settled down to a pleasant routine. Agatha spent all of her time nude. She was starting to get quite a tan. The Captain allowed her to do her share of time in the crow’s nest and at the wheel, but she didn’t have to scrub the decks, as her energies were more useful wanking and sucking off the crew members, who seemed to be in an almost permanent state of arousal from the sight of her gorgeous nudity and the fact that she was always so happy to be fondled and spanked. Even Orlando let her suck him off one day on the proviso that she put her clothes back on and refer to herself as Roderick.
When they reached the West Indies, Agatha put her pirate outfit back on and fought alongside the men when they attacked one of the Queen’s ships and sank it, though not before transferring all of its wealth to their own hold.
Eventually, after a successful series of raids, Bullfinch turned his ship around and headed back towards England.
Two days out from Havana, the Captain fell into a state of post-pillage depression. He really started to hit the rum hard.
“Mermaids!” he cried, staggering wildly across the deck, his eyes fixed on some mirage upon the horizon. His peg leg went into a knot hole and he tumbled over the side of the ship and fell with a loud splash into the peaceful swell of the ocean.
“We probably should try to rescue him,” said Orlando, leaning over the side.
“Damn near impossible for a man to swim with a wooden leg,” put in Blake.
“More rum for the rest of us without him though,” reasoned Buck, logically.
“Those sharks don’t look very friendly,” Agatha pointed out. “I wouldn’t fancy jumping in after him.”
“I can’t look!” cried Orlando. “Gruesome deaths upset me.”
And so it was that they found themselves without a captain.
“We’ll have to hold an election,” pointed out Buck an hour later as Agatha slurped on his cock.
“I’m willing to nominate myself,” put in Blake.
“I’ll go up against you,” said Blind Drunk Pugh, “I have seniority.”
Agatha stood up and quickly swallowed down her mouthful of cum. She stood defiantly naked with her hands on her hips and trails of semen running down her legs from cunt and arse.
“I should be your captain!” she cried.
“We can’t have a girl captain,” complained Buck. “Anyway you have your job. You’re the ship slut.”
“Don’t worry,” she smiled. “There won’t be less fucking with me as captain. There’ll be more, because I’ll order you to fuck me, even when you think you are worn out. At the moment I’m just taking care of your needs. You haven’t met my needs yet.”
“I don’t know,” mumbled Pugh.
“If you don’t vote me captain, I’ll feed myself to the sharks and you’ll be back to begging Orlando to gobble your nut-sacks,” she threatened. She knew she had them over a barrel. “And with a pirate queen as a your captain, you never know, some other horny sluts may want to join the crew.”
“I think we have our new captain,” conceded Buck. Agatha went below decks and found Bullfinch’s spare clothes. She put on a pair of leather thigh boots, fastened a six inch wide leather belt with massive skull and crossbones buckle around her slender waist and put a pirate hat with a big red feather on her head at a jaunty angle, then she went back aloft to address her crew.
“From now on, as long as I’m naked, all of you are going to be naked,” she told them as she paced back and forth on the bridge.
“Somehow, I have a feeling this is the end of piracy as we know it,” said Pugh as he pulled down his breaches and shrugged off his coat. “But I feel fine.”
Soon the entire crew were naked. Agatha was at the wheel, feeling the glory of her triumph and the invigoration of the sea breeze in her face and over her bare tits.
Behind her all of the men stood on the deck with their eyes riveted to her luscious round bare ass framed by the leather of her belt and her boots. All of their cocks were standing out stiff and proud like so many bowsprits pointing the way to a gloriously unpredictable future.
The End
 | A guest post by
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Hilarious - and surprisingly hot!
No doubt those Jolly Roger flags were flying perpendicular -- if not even higher!