1 - 20 of 42 Works in Sub "Calico" Jack Rackham
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Annie showing off her well-trained husband.
Series
- Part 7 of Kinktober 2025
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It was always a fantasy of Jack's to be filled and used, one that Israel Hands, his husband was all to happy to provide for him.
Written for Day 2 of OFMDKinktober2025 using the Prompts "Free for all" and "Cum Inflation"
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...и могли любить
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Сахарные сопли, сплошной ООС и чушь, которую я написала for fun, чтобы успокоиться и перестать грызть локти из-за того, что фанфиков по этой парочке почти нет- Language:
- Русский
- Words:
- 2,051
- Chapters:
- 1/1
- Kudos:
- 1
- Hits:
- 8
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[Podfic of] like his girl. by vexbatch pods (vexbatch) for grammarian
Fandoms: Our Flag Means Death (TV)
09 May 2025
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Audio Length: 13:01
Jack makes breakfast.
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You’re My Guilty Pleasure by killerweasel
Fandoms: Our Flag Means Death (TV), The West Wing
19 Mar 2025
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It's exactly what they've both been hoping for.
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Our Flag Means Death Kinktober 2024 Drabbles by RepoHorrorTodd
Fandoms: Our Flag Means Death (TV)
12 Feb 2025
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Here we go again! Let's see if I do better than last year. Once again, will update my tags as I post the day's drabble. Chapter names will only feature the part of the prompts I used in the drabble.
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Stede knows how to deal with bullies. He has been doing it all his life. For most of it, he has been too weak to fight back. Not that he didn't try, he did. It just never turned out well for him. More trouble always followed Stede when he tried, so he just didn’t.
He's not a kid anymore, he hasn't been for a long time, especially since taking to the sea. Out here, everyone that's not him or Ed may say it’s a childish fantasy. Stede knows the truth out on the sea. He’s the most grown-up he has ever been.
That fact does not stop him from being petty. Especially for bullies like Calico Jack. Stede didn’t even know what came over him. One second Jack is pissing on his shoes and in his face talking about having a dalliance with Ed. The next Stede has Jack pinned to a tree with a fist full of the man’s greasy hair.
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Stede teaches Jack a lesson he won't forget with Ed's help.
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Jack makes breakfast.
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Fang facilitates two scenes at once; on one side, Izzy gets fucked and doesn't know who it is. On the other, he gets a chance to spoil Jack a little. Everyone wins!
Series
- Part 10 of OFMD Kinktober 2024
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Just looking at Izzy made Jack’s breath catch in his throat. God knew he wasn’t some kind of prude, but Izzy was always so buttoned up - usually literally. To see him without even that extra layer felt… intimate. Lewd, maybe. Like Jack was peeping through a hole in a brothel door, unsure what he was about to see but his cock already twitching in anticipation.
Izzy stood before him, hip cocked to one side impatiently. “Are you just gonna stare at me?”
Jack pulled himself together by sheer force of will. “No. Nope.” He sauntered over and draped himself around Izzy, pushing their chests and bellies together. He had a job to do.
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CJizzy omegaverse, written for Izzy Hands Bingo 2024.
Series
- Part 1 of Izzy Hands Bingo 2024
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“Get those fuckin’ leathers off, princess,” Jack says. “Gotta make sure my favourite pussy in the Caribbean still tastes as sweet as ever.”
Izzy groans, but he squirms out of his trousers nonetheless. Jack is crass, yeah, but—at least there’s some bite behind all his barking.
Izzy needs a favour. Luckily, Jack is easily bribed with a mouthful of cunt. And he is so sweet and quiet on his knees...
Series
- Part 2 of florence's izzy hands bingo 2024
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Captain Hornigold's Three Princesses by Milien_the_Gremlin
Fandoms: Our Flag Means Death (TV)
20 Jun 2024
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Daddy Hornigold runs a tight ship and keeps his three Princesses - Edward, Jack, and Izzy - in chastity, demanding absolute obedience at all times.
Series
- Part 4 of Milien's Tweetfics
- Part 1 of Everyone's Favorite Toy, Izzy Hands
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Jack doesn't use his signal, but Izzy stops when he realizes Jack is panicking.
Series
- Part 5 of Give You What You Need
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An exchange of gifts (and sex).
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Siren!Jack gets his back blown out on a beach by a crab man. Blackbeard drops by.
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“So first you come out here to spy on me,” she says, and shit, it’s looking more and more likely that Jack might get her ass kicked tonight. “And then you contradict me.” She’s barely looked at Jack this whole time, and Fang only offers her an afterthought kind of glance now, like she could be talking to anyone. Jack’s cunt throbs. Fang grins like she knows it, throws the butt of her smoke into the gutter. “Someone oughta teach you some manners before you find yourself in trouble.”
Day 21 of OFMD Kinktober: Public/semi-public, “over my knee”
Series
- Part 21 of RoughWinds OFMD Kinktober 2023
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The first voice he hears is Edward’s, and while it’s not entirely unheard of for Edward to have shouting matches with himself, he can pick out another voice, and what’s more, it’s familiar. It’s just been a long time.
No way. No fucking way.But no, sure enough, it’s their old crewmate standing there, Calico Jack Rackham, right before Edward fucking cold clocks him in the jaw.
Series
- Part 4 of Sharp and Steady 'verse
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Stede wants to be whipped. Izzy calls in the big guns. Ed is an enthusiastic voyeur... at first. When Izzy and Jack are done with Stede and ready to play together, Ed and Stede can't resist asking to join in.
Series
- Part 20 of Space's OFMD Kinktober 2022
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And She Keeps Telling Me I’m Gorgeous, And I Keep Wishing I Could Sleep by Trashass
Fandoms: Our Flag Means Death (TV)
03 Sep 2023
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Jack should really learn to stop bragging so much
Idea cred: @mothmothymoth on Twitter
Prompts used: Overstim, electroplay, multiple orgasms
Series
- Part 2 of OFMD Pussy Bingo 2023
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Israel Hands is a good 30 years younger than his husband Benjamin Hornigold. Thankfully, Ben lets him do what he wants, when he wants, so long as he stays pretty and fucks him a few times a week. Or gets fucked by him. So Izzy hires a staff for their house; some are hired for competency, some are hired for...other reasons. And that's how he ends up with a varitable harem of younger men to play with: Ed, the tennis pro; Stede, the gardener; and Jack (or CJ), the pool cleaner.
Let's be honest, this is just a ton of Izzy in situations™ with a variety of younger men (and his older husband). It's just fucking and being fucked and a good way to round out Kinktober '22!
Series
- Part 17 of Anarchy in Kinktober 2022