Calico Jack and the petticoat pirates


John Rackham (1682-1720), commonly known as Calico Jack, was an English pirate captain operating in the Bahamas during the early 18th century. He was active towards the end of the era known as the golden age of piracy. He is most remembered for two things; the design of his Jolly Roger flag, a skull with crossed swords, which contributed to the popularisation of the design, and for having two females as part of his crew.

One was Anne Bonny, whom Jack had rescued after she had been whipped for committing adultery with him. The other was Mary Read, a former soldier who usually disguised herself a man.

Mary is said to have had an affair with Anne Bonny, who initially did not realise she was a woman. One account claims that Captain Rackham was enraged when he found them naked together in his cabin. However later the three of them were reconciled and both women continued to serve in Rackham’s crew aboard the Curlew.


Billy Bones smiled at the memory of his discovery, but he was keeping his mouth firmly shut. Calico Jack was the best captain he had ever served with, and the pickings were too good to go and risk it over a little thing like the Articles.

Although the articles were clear on the point, no women were to be brought on board ship, excepting those that were being held for ransom.

“What are you smiling about you lazy swab?” John Read had come upon him unawares. “Get on with your work.”

To Billy’s mind there was something queer about Read, but for a small man he worked hard and knew his business. He certainly wasn’t one to cross, so Billy’s response was token.

“Alright, alright keep your hat on.”

Read watched Billy Bones until she was satisfied that he had returned to the ropes and then she went back to pondering what to do about the captain’s ‘boy.’ It would not do for the crew to find out that ‘he’ was really a woman. They might start looking more closely at the man next to them.

Read, who had been born Mary, was used to pretending to be a man. With the collusion of her family, she had taken her dead brother’s identity at the age of 12. This had originally been to fool her grandmother into supporting them. Serve the old witch right, she thought, it was a stupid provision of hers to support only male children. Anyway, she did not need the old woman anymore. On the old lady’s death, Mary had left England dressed as a man to serve in the Dutch army during the late war. She had been good at it too. But peace had brought no dividend for her and so she had taken a chance and as Mary Read had travelled to the New World to seek her fortune.

As Damned luck had its way and it had thus always been so; she had never prospered as woman. Three weeks out of Bristol, the ship had been taken by pirates, and fearing for both her life and her honour she had quickly assumed her old identity as John Read.

She had been fortunate, the pirate captain had been Calico Jack Rackham on the scout for fighting ‘men’ to bolster his crew after his split with Captain Vane.

Things had gone well and the life suited her. That is until Calico Jack had brought the woman aboard.

Mary had spotted her at once; you can’t fool a deceiver. The ‘boy’ had an arse like two melons under her breeks and no amount of binding was going to suppress that bosom. She had recognised her at once as Anne Bonny, the wife of the governor’s lackey, James Bonny. Her affair with Jack had been the talk of the port and on the orders of the governor, Anne had been stripped naked and bent over the block in the town square to receive 30 lashes with the rod on that tender bottom of hers. How she had squealed, Mary remembered amused. I bet she wished she had allowed Jack to purchase her divorce now, Mary grinned as her mind’s eye relived the sight of Anne’s full bottom squirming on the block. As pretty as any doxy she had had in Flanders for a shilling.

The one thing Mary hadn’t counted on was Jack bringing Anne on board disguised as a boy.


Calico Jack wondered how long he could keep Anne a secret. He was sure that Billy Bones had seen something when he collected the tray from the cabin. There was an odd grin on his face when he left. Anne had sworn that she had been discreet, but her feet had been bare and he was not at all certain that she had been dressed.

“I’ll tan your arse for you, if you are lying to me girl,” he had said.

Her eyes had gone wide at this and her hands had slipped to her behind. There had been a battle of wills between them ever since she had come aboard. He had had to take a short leather strap to her bare bottom, thrice now, the first time on her tender stripes. She had kicked up such a devil of a fuss that he had had to desist on that occasion lest she reveal herself to the crew. But he would be obeyed; this was no childish romance. This was serious business.

The crew would tolerate the notion that he had a ‘bum-boy’, but not a woman. Although Anne riled at the idea that the men believed such, perhaps because the gossip was too close to the truth as to forestall pregnancy he had used her thusly. Strangely, she had not complained at her rough treatment at the time, but insisted in bleating about it the next day. He was beginning to suspect she only wanted attention and was try to provoke him.

He only wished that she would understand that he would be testing the crew’s loyalties if she were revealed as a woman. They might even cast her overboard as a Jonah.

The more he thought about it, the more he was convinced that Billy knew. He cast his eye around the deck and studied each of the crew in turn. Sorting the loyal from the others in his mind and the others from those he might have to kill.

His eye fell upon John Read. The man was an enigma. When he had first signed on, some of the men from his previous ship had not appeared to recognise him, almost as if he had been in disguise. At first he had suspected him as a government informer, but he had a good instinct for such things and his nose told him that Read had dark secrets of his own.

One of them, he decided, was that Read had guessed that Anne was a woman. In that instant, Calico Jack Rackham made a decision.

“Who commands here?” The question sent a shiver around the Curlew.

The more timid members of the crew began to eye the rigging for a place to escape. Others began to feel themselves for their concealed shivs. Who had challenged Jack? The question formed in crew’s mind as a single thought.

“Captain?” Billy Bones drew a cutlass and fell in behind his captain and scanned for unseen enemies.

Mary Read primed a brace of pistols and did the same, although she guessed the source of the trouble and quietly cursed.

“Who commands here?”

“You do captain and I’ll skin the first man who say you don’t,” one of the men called out.

“Anne,” Jack bellowed.

Billy relaxed and smiled with relief.

“That’s the way captain,” Billy chuckled.

Most of the rest of the crew were also smiling. It seemed that few had been fooled by Anne’s disguise.

“Who is Anne?” Blind Paul asked. The old man, who was useless in a fight, was the best sail maker on the ship.

“There’s a woman aboard Paul,” Billy reassured him.

“Oh aye, I knew that. I can smell her. There has been for a year or more now,” Blind Paul shrugged and turned back to his canvas.

“No, no, just since Jamaica,” Billy assured him.

“If you say so Billy Bones, if you say so.” His west country English accent as inscrutable as ever, Paul shook his head and smiled, men were apt to believe what they wanted, he chuckled to himself.

Anne shuffled reluctantly onto the bridge and looked about with cow-like eyes.

“What are you doing?” She hissed at Jack.

“Who doesn’t know that this is a woman?” Jack bellowed.

“I can see plain that she is captain,” Blind Paul yelled out good-naturedly.

The crew fell about laughing, or though one or two stood opened-mouthed with surprise.

Anne passed her hands over her clothed body as if she were naked and blushed.

“Anyone here have a thing to say?”

“It’s that Bonny girl from Jamaica aint it captain? Good on yer,” William Piper said and turned back to scan the horizon for bigger threats to the ship.


Anne Bonny made a turn of deck, each step a trial as her bottom burned beneath her skirts. None of the crew cast so much as a glance in her direction, but she knew that every man jack of them must heard her yelling, as at last unrestrained and paying no mind that they would be discovered, Jack had spanked her with a will not an hour before. She hadn’t been so humiliated, since… she blushed as she realised that most of the crew would have stood witness at Jamaica. Nothing could be as bad as that. Although earlier that day, Jack had given it a damn good try.

Anne had berated Jack for exposing her to the crew, although none had dared to complain.

“Now I am an accomplice and the scum of the Caribbean will name me your whore,” she had raged

He had said nothing, but had stood with his hands on his hips looking her up and down as if contemplating a purchase.

“Now Mrs Anne Bonny I have had just about enough of you, get those breeks down and place yourself face down on the cot.”

“I will not.” Anne had backed away eyeing the whip in Calico Jack’s hands with a grim remembrance of Jamaica and the governor’s justice.

He saw where her eyes were resting and quickly cast the nasty length of leather into the corner.

“Nay lass, I am set upon using this,” he said grimly taking up the short length of leather he had used before.

“Look all right I’m sorry but…” she spoke nervously holding both hands up in a holding gesture.

“Your breeks down at once.” A dirty smile danced on his cruel mouth. At that moment, she wished she could hate him, but his threats made her near swoon and tremble like a maiden on her wedding night.

There was nowhere to run. He turned her roughly about and tore her gentleman’s breeks to rags around her knees. Then he threw her down and pinned her with his knee at the small of her back.

The strap had made short working searing her naked bottom until she announced its coming at the top of her voice. If she had hoped he would then take pity she was mistaken, as if sensing victory Jack took another five minutes and more making sure that she finally knew who was captain aboard his ship.

Anne blushed again at the memory and stared at each of the crew in turn to see if they could read her thoughts. Only the quartermaster’s mate, Read paid her any regard and he was smirking. Read’s eyes stole more than glances from Anne and there was something about his manner that told her that he knew and approved of Anne’s rough handling.

Anne tried a glower in Read’s direction, but there was something about his gentle handsome demeanour that disarmed her and instead she smiled.


In the days that followed the ship held much of Jack’s attention. On one occasion a sail had been sighted. And although the crew had been wary, Jack had given orders to chase it knowing that it could just as easily be Royal Navy sloop or even a frigate in these waters. They had not even got close and their prey slipped over the horizon and disappeared in the evening gloom.

Once her sore bottom had eased, Anne had found the endless days somewhat boring and had taken to teasing the crew. A glimpse of ankle here, a thigh there after an ‘accidental’ tumble. But despite her best efforts, she was irked that she was largely ignored. Few of the crew were stupid enough to mess with Calico Jack’s girl.

There was one who’s eyes followed her on her daily tour of the deck. John Read, the gentle-faced rake who had been so amused by her spanking.

“What do you do here?” Anne asked one day.

“I’m the quartermaster’s mate,” Mary replied keeping her voice even lower than usual in case Anne was more sensitive to feminine tones. Then seeing Anne was none the wiser added, “I stand second to the quartermaster, the chief helmsman at sea and watch commander in port.”

“So you are an officer?” Anne tried to sound impressed, as she knew boys liked that.

“I suppose if we were aboard a Navy ship I would hold a warrant, here…” Mary shrugged, “there are less set above me than below I guess. I stand sixth or seventh aboard maybe.”

“Will you try for a ship of your own one day?”

Mary laughed.

“I am a landsman my pretty. I would not know the sails let alone the way of things when it came to charts. No, I might stand as second mate at a push. Anyway, who would be a captain? Not a job for a girl… eh man who is for a long life.”

Taking the slip for a suggestion of her own ambitions, Anne giggled.

In that moment Mary risked all and with one look around she grabbed Anne in a clinch and kissed her. She hoped that Anne would take her for the woman she was, especially as she kissed back. But after a moment longer Anne broke away and slapped Mary hard.

“I should have you flogged you impudent dog. If I tell Jack…”

“If you tell Jack then I will be dead for sure,” Mary said defiantly. Would he kill her if she showed her hand, she wondered. “You, well yes, he may flog. After all you did lead me on.”

Anne blushed, knowing both were true and seeing her boldness rewarded, Mary smiled.

“You…” Anne could not help but smile back at the bold rogue.


After that, Anne took every chance she could to catch Mary in a quiet corner. No slight thing on a ship the size of the Curlew. Mostly as their strange courtship progressed, they just talked, but every now and then Mary stole a kiss and groped at Anne, hoping that she would guess the secret.

As it happened, not long after, Calico Jack took the Curlew to a quiet sound for provisioning and Mary was left aboard in charge of a small skeleton crew.

“Anne remain here and don’t bother the crew,” he said as he stepped aboard the last jolly boat.

Anne watched as Jack’s boat rounded the point and then if butterflies tickling her stomach sidled up to Mary Read.

“An officer now after all,” she simpered.

A crewman standing near scuttled away lest he see or hear something that he ought to report to Jack on his return.

“Now doesn’t that make you hot?” Mary leered seizing the girl.

“It’s a hot day, why not come to Jack’s cabin for something cooling?”

Once in the cabin, Anne started fanning herself with the hem of her skirts. She even put her leg up on the bed to reveal a length of thigh.

“It is so hot here, even without pantaloons,” she whispered huskily. “Are you surprised I asked you here?”

“Not as surprised as you are going to be,” Mary laughed. She let her boys voice slip and sashayed across the cabin floor as her gender demanded.

A cloud crossed Anne’s face, but before she could even think Mary took her in her arms and kissed her deeply.

“I’m… I’m so bad…” Anne groaned. “I deserve to be whipped.”

Mary tore open her shirt and kissed Anne again.

“What the…?” Anne jumped back.

Mary leered and shoved Anne back on the bed and reached under her skirts. As she did so she kissed Anne passionately and linked her tongue around Anne’s. Anne tried to push Mary off, but there was the slightest pause as they both lingered on the kiss.


Mary shrugged.

“You must have known. I spotted you straight off when you came aboard in breeks.”

“I… no…” Did she know, she asked herself then in denial growled, “I don’t go with… I mean it’s not…”

“I know it’s not natural is it? You should be whipped.” Mary folded her arms and threw back her head and laughed. “What will you tell Jack? You thought I was a boy? Not the best defence I’ll warrant.”

“Yes. I mean… oh get out.” Anne threw a cushion at the still laughing Mary who caught it easily with one hand as she rebuttoned her shirt with the other.

“I have duties to attend to,” Mary said as she made for the door. Then in a fit of mischief dropped her seaman’s strides and treated Anne to flash of her broad white bare bottom. “Dream on this.”

Anne did. In the days and nights that followed while Jack scoured the shore for fruit and water, Anne lay abed and dreamed of Mary’s hot kisses and her firm white bottom as it slipped from her sight.

The unconsummated affair had aroused her because it was forbidden. She knew then that she would never have gone through with it. But Read as a woman, that was something else. Even more forbidden and without cheating on Jack, not really. The danger, the sin, oh the punishments, she thought, wild with dreams of it as she thrashed naked in her bunk, her hands straying where her mother had forbidden them to.

Mary harboured similar thoughts. A dalliance with Anne was not treachery, not really. Although unlike Anne, she saw nothing sinful in the pursuit of women. Not that she was adverse to a man, but where the male gender was concerned, she had impossibly high standards. I have been foiled with Anne though, haven’t I? She thought ruefully.

Then to her surprise, two days later Anne came on deck.

“What is your name anyway?” She asked as she strolled past pretending to be watching a seabird.

“Mary.” Mary’s heart raced at the turn of events and she could hardly dare to breath.

“Come to the cabin at the change of watch and we will… talk.”


Mary and Anne lay naked and entwined upon Jack’s bed.

“Have you been with many girls?” Anne was curious.

“I had to go with them when I was in the army to allay suspicions.”

“Didn’t the girls mind?”

“At first they did not always know, I would feign drunkenness or I had a pego strapped to my waist and in the dark…”

Anne gasped and blushed at the idea.

“Do you still have it?”

“You really are a bad girl, I should spank you soundly.”

Anne blushed and hugged her friend tightly shuddering at the threat. Mary kissed her. Then continued, “later I found girls like you who didn’t mind the change. It was easier then.”

“Stand by to come along side.” The voice was distant and muffled by the ship’s planks, but both women knew Jack’s voice.

“Christ take the devil,” Mary cursed and got to her knees and crawled to the edge of the cot. Her bare bottom mooned up as she looked frantically for her clothes.

“Get out, quick, if he catches us…”

The door opened and both women gaped in horror at Calico Jack as he filled out the doorframe to the cabin.

“If.” He growled. “Who…?”

Jack was confused at the presence of the mysterious woman and his tired brain ticked two beats before he placed the stricken face.

“Read, you’re John Read,” he bellowed.

“Mary captain,” Mary said sheepishly, suddenly the tough soldier-sailor had fled.

“Well, well, well,” Jack laughed, “at least I am not cuckolded I suppose.”

“Cuckolded, no we were just…” Anne was frantic with fear,

“I know what you were just. Maybe I am not the cuckold but I have been deceived,” Jack raged.

Just then Billy Bones came up behind him.

“Oh lord,” he gasped. “Are we the petticoat pirates now?”

The two women tried to cover their nudity and Jack gave Billy a look that sent him swiftly back on deck.

“Now my two fine lovelies I want you belly down on that cot,” Jack said with a voice like black silk as he unbuckled his belt.

“Can’t we talk about this?” Anne fluttered her eyelashes nervously.

But Mary merely swallowed and turned about on her knees and pushed her bare bottom upwards.

“I like that even better,” Jack said thickly, beginning to warm to the woman.

“Happy to oblige captain,” Mary said dryly, adding “come on Anne, time to pay the piper.”

“But I…” A tear ran down Anne’s cheek. Then in a quiet voice she whispered. “I suppose we deserve it.”

It was strange kneeling next to Mary with her bottom in the air, but the revealing posture seemed to take some of the edge of Jack’s wrath. Although he still had enough left to do the deed.

The belt seared first Mary’s bottom and then Anne, who took it far less stoically. Once he had marked his territory with a firm ragged blush all set for further exploration, he turned all his attention to the interloper Mary.

The belt stung her hard and fast, plying its trade until every nook of her pale flesh carried a peony hue and her breathing had become decidedly ragged. Then just before she might have broken into sobs he spared the lady pirate’s backside and switched to his lover’s.

Anne squealed like a schoolgirl from the first to the last but Jack did not go easy until he adjudged her bottom was a red as Mary’s.

“Cross me will you? I ought to make you walk the plank, I ought to keel haul you, I…” He brought the strap down as hard as he could down onto Mary’s bottom, not sure if it was rage or passion that drove him. “So you like lady flesh do you? Well I have a daughter for you to kiss for the entertainment of the crew just as soon as I am done here.”

“Yes captain,” Mary sobbed at last.

“What no pleadings?”

“I betrayed you captain, guilty as charged, I’ll make it up to you anyway you want,” Mary hadn’t cried for a man for as long as she could recall. Now here she was arse up crying like a babe and craving her surrender.

Jack paused and regarded the two reddened behinds side by side and felt his cock stand.

“Any way is it?” He rubbed his chin.

“Please, we’re sorry aren’t we Mary?” Anne pleaded sensing abatement in his rage.

“Yes sir, couldn’t be more so, pay us out as you will.”

Anne looked sideways in horror, was Mary begging for more? Something throbbed more firmly between her pulsing bottom at the very idea of it. You traitorous bitch, she cursed her sex, which was weeping even as she was.

“Very well then, another turn or two each with this and then we will see,” Jack’s voice was low and deeper than Anne remembered.


It took the crew time to get used to two women on deck. Especially as Mary Read continued to serve as quartermaster’s mate even though Jack insisted that she wear women’s attire. That is until a ship was sighted. Then both women slipped below and re-emerged as ‘men’ girded with rapiers and a brace of pistols each.

Jack had also given orders that if the two women dallied together they would face the consequences. Thereafter Anne and Mary played a game where Anne was cunning and Mary indiscreet to ensure that not a week went by that they weren’t arse up in Jack’s cabin tasting the belt.

Mary took delight in teasing Anne by taking bets on which cunny or that near-by he would enjoy first after their thrashing. Usually while they both still kneeled in submission upon the cot.


No one knows for sure about the true nature of Calico Jack’s relationship with his petticoat pirates. But as with many privateers of the age, their careers were short. In 1720 all three were captured and the two women only escaped a noose by ‘pleading their bellies.’ That is to say both were pregnant.

Calico Jack Rackham was hanged and Mary died in childbirth shortly afterwards.

As for Anne Bonny, well she found another man to look after her and lived a long life as a plantation owner’s wife.

8 Responses to “Calico Jack and the petticoat pirates”

  1. What fun, DJ, and very nicely riffed. Gotta love a guy who isn’t afraid to take liberties with history in a just, spanking cause. I’ve done that myself more than once or twice. 😉

    Congratulations and do carry on.


    • 2 DJ

      Thanks Dev

      Its all true I tell you – my great grandmother had the lost diaries of Anne Bonny. 😉

      Actually Anne was supposed to nave been sentenced to a whipping for adultery – no idea if it was carried out in reality.

      DJ 🙂

  2. 3 Gingery2k


    Easy to read & navigate and amazingly pleasant to use with the cell phone–and without memory issues. But even better is the quality of the writing–many cuts above the best of what I’ve seen. God bless you for your generosity in making this a free site.

    [multi post edited by request]

    • 4 DJ

      Hi Gingery

      Thanks for the positive feedback.

      I just left in the bits that were about me! Lol

      I am pleased to know it works on your medium – that is v useful feedback – but I only handle content all the tech credit goes to WP.

      Thanks DJ

  3. 5 fatherjim

    Actually, a great deal of the facts do sound accurate! Who’s to say what really happened. There would be no history book to relate the true facts anyways! Great stuff, as always!


  4. 6 Dave Wolfe

    An exceptionally entertaining piece, both the history lesson and the story! Not to drag a tired old joke from under the table by its foot, but pirate booty always makes good fiction, and you deserve the extra attention the inclusion on Chross’ weekly list will bring!

  5. 7 DJ

    Thanks again,

    I took care to write a short story consistent with the facts – later historians went to a great deal of trouble to blur any suggestion of any lesbian liaison between them. Calico Jack’s reaction in the story is plausible but we will never know.


  1. 1 - Chross Guide To The Spanking Internet

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