That's #JackOffWeek

Sigh

This is the real reason why I made the Jack outfit for #JackOffWeek! Look how cute he looks ahhhhh

Ofmd fanart: young Jack and Izzy having sex. Izzy is on his back with Jack on top of him, touching Izzy's pierced nipple with his right hand. Jack's eyed are closed while Izzy's are half-open. There is a tear rolling down his face. An ivy tattoo curls around Izzy's ribs and his gender affirming scar. The colours are mostly blue with highlights of orange.

And another one for #JackOffWeek

#ofmd #cjizzy #izzyhands #nadsart

Ofmd fanart: Edward standing in front of Jack who is encompassing him with both of his arms. Ed is holding a cigarette up to Jack's lips and looking at the viewer. Ed's tshirt is slipping off his right shoulder and the whole drawing is in the shades of purple.

Okay I admittedly forgot completely about #JackOffWeek despite having it in my calendar but anyway! Reposting some of my older works:3

#edjack #ofmd #nadsart

Lots of great content on #JackOffWeek to catch up on!

OFMD's Calico Jack, sticking his tongue out at the camera, wearing a matching teal chest harness/collar set, tipping his hat at the camera.

You know what they say, ride a horse and all!
For #jackoffweek I got to cross of one of my to-draws with a cheeky Calico Jack!

I pulled down my original post bc someone kindly let me know the one of my references requests credit when his image is used. My bad... 1/2

His Name was Jack - Chapter 4 - wasabi_poptart - Our Flag Means Death (TV) [Archive of Our Own] An Archive of Our Own, a project of the Organization for Transformative Works

#JackOffWeek may be over but the penicillin takes a while

Chapter 4 is posted!

archiveofourown.org/works/617670...

#JackOffWeek was an absolute blast! Thank you so, so much to the amazing mods who put it on. One of the best events ever. No place I'd rather be than Jack Gulch! ❤️

Photo of Calico Jack fromOur Flag Means Death. He's holding a bottle, has his mouth open, and text at the bottom of the image reads: "Aaaaeaeuauughhh! I'm burning!"

Thanks for taking part in #JackOffWeek everybody!
Don’t cry because Jack is leaving.
He leaves you with memories and a case of the clap.

An iPhone Notes app screenshot that simply reads “Calico jack as a waffle”

because it’s still #JackOffWeek somewhere, i put this in my notes app in 2022 and i have absolutely no recollection of what this is supposed to mean or where i was going with this

Two calico jack cosplayers. One is femme and has a tiara and a fur shrug, the other is masc and is holding their fists out to show off knuckle tattoos that say “JACK SHIT”. Sparkly cursive text says “Fancy” and sub-text reads “Calico Jack feat. Jackie XCX”

WAITTTTTTT!!!!!

#JackOffWeek wouldn’t be complete without @miaugly.bsky.social ‘s absolute fucking masterpiece: Calico Jack covering Iggy Azalea’s 2014 hit “Fancy” (feat yours truly on the hook)

www.tiktok.com/t/ZTYcg2s9M/

Close up of a femme calico jack cosplayer with only the lower half of their face visible. They are holding a wooden bookmark with a laser etching that says “Warning: ‘Calico’ Jack Rackham”; the font and dotted underline showing that it is an AO3 tag. The Our Flag Means Death show logo is also etched on the bottom. The bookmark has a yellow tassel

Thank you #JackOffWeek, it’s been a blast!!

He is every bad decision you made in your 20s. He is Florida Man in the very best way. He is fried chicken from the bucket and fruit cocktail from the can. He is going down on you with a snorkel and a comic book. He is getting high in the car on the way to Thanksgiving dinner. He owes you so much money. He is bringing you a dozen (stolen) roses. He is an agent of glorious chaos.

#JackOffWeek

A package of vegan chicken nuggets from the brand “jack & annie’s”. They’re labeled “crispy jack nuggets” and the small text clarifies that they are vegan jackfruit nuggets

#JackOffWeek

My other fic won’t be ready to post to AO3 for a bit so I wanted to cap off #JackOffWeek with my filthy young #JackEdHands Twitter thread fic. Trans Izzy, cis Jack & Ed. Absolute filth.

Ed and Jack find out Izzy has a cunt. (Picturing this as the Always Sunny episode title.)
____

simp.
informal + often disparaging: someone (especially a man) who shows excessive concern, attention, or deference toward a romantic partner or love interest.

#JackOffWeek #JOW #CalicoJack #CJizzy #IzzyHands #NSFW

Sandwich board that reads If we can't make you look good you ugly

Lesbian Jack beautician AU #JackOffWeek

A fic called hatred therewith but Yaz113. The summary reads: Jack pisses on Stede's boots. Stede sees red. The rest, as they say, is history. OR StedeJack hatefucking. That's it. That's the whole fic. Bible quote in the notes reads: Better is a dinner of herbs where love is, than a stalled ox and hatred therewith. -Proverbs 15:17 (KJV)

Tags of the posted fic: Rating Explicit Archive Warning: No Archive Warnings Apply Category: M/M Fandom: Our Flag Means Death (TV) Relationship: Stede Bonnet/"Calico" Jack Rackham Characters: Stede Bonnet, "Calico" Jack Rackham Additional Tags: Episode: s01 e08 We Gull Way Back, Hate Sex, Mildly Dubious Consent, But also, Enthusiastic Consent, Inexperienced Stede Bonnet, Top "Calico" Jack Rackham, POV Stede Bonnet, Warning: "Calico" Jack Rackham Language: English

ok OK so to ACTUALLY wrap up #JackOffWeek, have some StedeJack hate-fucking set mid 1x8🥰
archiveofourown.org/works/61968226 #JOW

A bottle of Southern Comfort whiskey

A bottle of Royal Crown cola, aka RC

#jackoffweek

Although Jack has a more refined palate now than he did in high school, he still enjoys the classics.

Ever since my brilliant Jack-Off-Week co-mods came up with the idea for Simp Saturday as a prompt, I’ve been trying to find the best way to say all things I want. I’ve made multiple lists of people to simp over, but as usual, hours later I remember another person to add to the list and as I do not want to leave anyone out, only four people are being named here today while dozens more shall be unnamed but loved upon. Like many, I found OFMD during a rough patch of life, and then I fell into the Canyon, landed in Jack Gulch, and have happily played in the mud ever since. There are so many creative, generous, enthusiastic people here and just being around you brightens my days. Your writing, your art, your gentleness and support, your silliness, your openness all give me enormous heart eyes when I think of you and talk about you. My IRL friends know about my Pirate Pals and are fond of you all at a remove.

#JackOffWeek #JOW. Simp Saturday 1/3

Looking for some simp Jack on this final day of #JackOffWeek ? Here's a sweet Double-Wide verse fic for you!

"Rum Raisin" (rated G)

archiveofourown.org/works/55141027

And my illustrations for Coconut War, chapter 3 of "The Marks Left On Your Skin"
archiveofourown.org/works/600361...

Last #EdxJack chapter, Ed's in his late 20s
It's a miracle these two survived each other at their youngest and dumbest.

#JackOffWeek #JOW #CalicoJack #EdwardTeach #ofmdfanart

My illustrations for chapter 2 of "The Marks Left On Your Skin"
archiveofourown.org/works/600361...
Early to mid 20s #EdxJack

#JackOffWeek #JOW #CalicoJack #EdwardTeach #ofmd #ofmdfanart

For Jack Seduction Fics on this last day of #JackOffWeek, may I present my favorite CJIzzy sex fic of all time?

"I said I've never actually had sex. I've never fucked anyone and no one has fucked me."

archiveofourown.org/works/46708708

@killerweasel.bsky.social 💚

I have an enormous post for Simp Saturday in the works...I love so many people so fucking much...
#JackOffWeek #JOW

1: In the darkness, Jack was just the smouldering tip of some pungent cheroot and the orange-and-blue-lined shapes of a drooping moustache, thick fingers, and round lips. 2: after the ride is over. shenanigans ensue etc etc. also jack is there because i like making it nasty. 3: Jack slung his arm around Izzy’s shoulders and began walking them down the steps and onto the street. “Doll, I’ve got a coupon for a free Egg McMuffin with your name allllll over it.” 4: he is of course talking about piss. 5: “How old are you, Jack?” “Uh. Nineteen.” 6: but oh nooooooo she’s halfway through all wet and naked etc and then jack comes in to sexually torment her (but in a nice way). 7: jostle Ed forward and make his arse jiggle. Jesus fucking Christ, he was so sure that he was simply jealous of Jack and the fact that he got to fuck Ed, but is he jealous of Ed too? Jealous of the fact that Ed is being fucked by Jack and Stede isn’t? This is too much unwanted self-discovery for one already very weird evening. 8: just like “shut tf up. YO ALSO ED IS ALL LIKE I DON’T HAVE FRIENDS NO ONE WANTS TO HANG WITH ME BUT ACTUALLY JACK LIKES ED AND WANTS TO HANG BUT ED BRUSHES HIM OFF ALL THE TIME. whenever he texts jack for a hook up it’s one message after a string of texts from jack that he hasn’t responded to. 9: hornigold era, ed jack izzy anne bonny mary read are all on hornigold's ship, he is WEIRD AND CREEPY and makes evrryone live as a "family" with him as the father and the crew as 10: so is jack and he’s also like “yeah fuck yeah and besides it’s totally not gay right”

11: “Those fuckin’ eyes, man, you’ve got girl eyes. And that hair? Shit, if I didn’t know you better I’d fuckin’ fall for it.” Jack looked away, and started fiddling with the stack of pick’n’mix bags. “Fall right for it,” he muttered. 12: Jack is reformed after some kind of accident where he was badly injured in the stomach area (analogous to getting cannon balled in the show), he likes to go on about how much of his intestines they had to remove (still got enough for izzy to rearrange em on ther regular tho 🤪) and he’s still gross but ultimately harmless now. He has the most busted up little chihuahua dog in the entire world who he dotes on like an actual child and stede does Not say anything about how he clearly has a fondness for collecting small breeds. 13: (jack was their first bassist). 14: severe case. Doctor Teach and I will require your assistance in administering the treatment. Scrub up, Nurse Rackham, we need to save this young woman’s life.” “Fuck yeah, I’m totally a registered pussy nurse. What tools do we need?” 15: stacked pissverse modern au - ed is on a business trip so stede begrudgingly brings jack over for some fucking (while ed is on video call obv, really it’s ed and stede having phone sex while stede uses jack as a fleshlight).

in honour of the last day of #JackOffWeek and also ignoring that i missed wednesday whippies, here is a collage of snippets featuring the 15 different jacks currently languishing in my google docs. thoughts and prayers that one day they will be released from wippies jail 😔🙏

Flesh and Bone - killerweasel - Our Flag Means Death (TV) [Archive of Our Own] An Archive of Our Own, a project of the Organization for Transformative Works

Title: Flesh and Bone
Fandom: Our Flag Means Death
Characters: Jack, Ned
Pairings: Jack/Ned
Word Count: 883
Rating: R
A/N: After Episode 1x8
Summary: After the canon ball incident, Jack makes a new friend.
#JackOffWeek
archiveofourown.org/works/55516810

A Dalliance - killerweasel - Our Flag Means Death (TV) [Archive of Our Own] An Archive of Our Own, a project of the Organization for Transformative Works

Title: A Dalliance
Fandom: Our Flag Means Death
Characters: Jack, Stede
Pairings: Stede/Jack, Ed/Jack (past)
Word Count: 1342
Rating: NC-17
A/N: AU during 1x8
Summary: Jack gets everything he wants.
#JackOffWeek
archiveofourown.org/works/59715553