did everyone get cake?

not again! oops!

milk him

“You can build all the dick rockets you want to go to Mars while you try to leave the rest of us on the burning Earth. We’re gonna take control. This is our world, and it’s our government, and it’s our money.”

— Sara Nelson, Association of Flight Attendants president

Ed and Stede are sitting on a sofa, Ed leaning back into a corner and Stede next to him. They are both naked, save for the open robe Stede has on. They're jerking themselves off, Stede looking flustered and Ed watching him. Stede says "This is something pirates do?" and Ed answers "Yeah mate. All the time".

OFMDKinktober Day 2: Mutual masturbation

and an accompanying fic: archiveofourown.org/works/50494825

#ofmdnsfw #ofmd #gentlebeard #ofmdart

Ed is naked, kneeling on a bed. His hands are bound behind him by leather cuffs. His hair is up, and he has on a choke collar that is connected to his cuffs by a leather leash. The cuffs are also connected by a metal rod to a large vibrating dildo that is in his ass. His eyes are closed and his mouth is open gasping for air. Stede is seated in a chair in front of him, wearing a robe. He is smiling fondly and is holding a remote control in his right hand.

DAY 3: Predicament bondage || Remote control device

#ofmdkinktober #ofmd #ofmdart #gentlebeard #ofmdnsfw #nsfw

View is of Ed's bare ass as he lies on his front, legs spread. Stede's left hand is clutching Ed's left cheek while also thumbing open Ed's hole, allowing come to spill out of it and trickle down his taint and balls. Stede has a wedding band on and his hand is freckled. Ed has several tattoos showing, including: a treasure chest on his ass; an 'X' with a dashed line leading to it by his hole; a jellyfish on the back of his right thigh; double bands around his left thigh; part of his snake tattoo winding around his left thigh; an anchor on the inside of each thigh. His ass and legs are hairy.

day 29: creampie

It's rumored that of all the various places he had visited, the Gentleman Pirate's favorite was a secluded and private spot known as Teach's Hole. "The view is unparalleled," he was known to say.

#ofmdnsfw #gentlebeard

[orig. posted 10.29.22]

Art of Stede seeing Ed’s Tdick for the first time. The text in the drawing says “Oh Ed! It’s beautiful!” “What are your plans for it?” “I’ll probably just eat it 🩵” “Good plan, I like that💜” Stede is kneeling in front of Ed, his very pale and minimal shapely butt and very shapely balls can be seen on the left. He is looking into Ed’s eyes. Ed has his legs spread, with his right leg hooked over Stede’s shoulder. His Tdick is on display and standing at attention as illustrated by the two purple exclamation points beside it. To the right of this is a more simplified drawing of the two from a birds eye view. Ed is laying back with his hair and arms thrown around him. He has heart eyes and his mouth is hanging open. He has both legs thrown over Stede’s shoulders. Stede’s head is buried in Ed’s lap, his hair is also a bit mussed up. He has one arm propping him up, and the other soothing Ed’s left calf. They’re outlined in an pastel orangey-yellow. The background of the picture is a pastel lavender

(Originally Posted 1.19.2025)
Happy #SexualSunday! Here’s some #spicygentlebeardart of my favorite boys being disgustingly cute.
Based on a skeet from a few weeks ago #ofmd #ourflagmeansdeath #ofmdfanart #ofmdnsfw #transmascedteach #ftmedteach #gentlebeard #gentlebeardnsfw #blackbonnet #edstede

Someone’s celebrating a big day with their very own handmade party hat!

New Hard Disciplines is out today!

CW: 🍆 and 🪢 and 🥳

#OFMDfanart #OFMD #OFMDnsfw

close-up of Ed's ass as he's riding Stede. His cheeks are darkened from being spanked repeatedly. Stede's left hand is resting on top of Ed's right cheek. The middle and ring fingers of his right hand are pushed into Ed's hole alongside Stede's cock - all three are wet with lube. Ed's hole is slightly darkened. There is an X tattoo by his hole, a kraken trampstamp, a tattoo of Stede's initials in a heart on his left cheek, and a treasure chest on his right (the latter two half hidden under Stede's hands.

so @ignisentis.bsky.social was talking about Ed needing Stede's fingers in addition to his cock and it reminded me of this kinktober sketch I did. I'd posted it with a bunch of other ones here but figured it deserved to shine on its own

#ofmdnsfw #gentlebeard

a colored drawing of ed teach from our flag means death, naked in bed, jacking off his dick :)

#ofmdnsfw #nsfw

in the stripped club straight up jorking it
and by "it" i mean ha ha well
my peanits

Stede Bonnet from Our Flag Means Death smiling in his teal outfit from episode one with the words butthole buccaneer over the top and the rainbow flag in the background

And we love him for it #OFMD

you’re laughing. ed’s getting his butthole buccaneered and you’re laughing

Digital line drawing of Stede from OFMD nude and erect. He's curled up with his knees hooked over one forearm and his dick tucked through his thighs so it's lying right down next to his butt.

excuse the quality i drew this in a hurry cus i have. a question is there a name for tucking the dick behind the thighs like this bc its one of my fav positions to put stede in. unrelated to the fact it looks kind of mermaidy which i only realized as i was drawing this. fate perhaps

what about babygirlifying historical figures without written consent

doubtless

illustration of Ed and Stede from Our Flag Means Death. Both are nude. Ed is on his hands and knees, and Stede is fucking him from behind, hands on Ed's hips. Stede is flushed and smiling, and says "I may be landed gentry but I'm THRILLED to be granted entry!" Ed is staring ahead, with a bewildered/pained expression on his face.

hi all! #ofmdnsfw

Giggling at how the way I draw Ed has evolved since 2022. I will cutesify that middle aged man!!!
#ofmd

cat Roach!

a medieval style digital drawing. in the center frame, the crew of the revenge are gathered into a group on the deck of the ship. clockwise from left: Frenchie, Pete, Lucius, Roach, Auntie, Jackie, Ed, Stede, Wee John, The Swede, Fang, Izzy, Zheng, Olu, Archie, Jim, and Buttons (as a seagull). the borders are ornate, with vines, leaves, and flowers in bright colors and some gold leaf accents. there are two of Lucius’s weird little Ed drawings in the margins: Ed as a seagull and Ed as a small purple dog. there are four little frames in the border, showing: Wee John as Calypso, Stede’s hand handing Ed a teacup, Stede stabbing Ed from the run me through scene, and Stede holding a message in a bottle to his chest.

now that the gang’s all here, well, the gang’s all here #OFMD #OurFlagMeansDeath

Butthole Buccaneering has never looked so good 💋
#OFMD #OFMDfanart #OurFlagMeansDeath

⚔️

a drawing of Jim kissing Oluwande on the cheek, cropped from mid-thigh up. Jim is dressed as Tybalt from Romeo and Juliet, wearing a cropped vest with jesus iconography on the chest, a pair of high-waisted black pants, a gun holster slung across their hips, and a gun harness over their shoulders. Olu is dressed as Mercutio at the party, wearing a sequined cape, bustier, and miniskirt, a sequined choker, and long gloves. His hat is sequined to match the outfit. The drawing is shaded loosely in pencil, with a desaturated pale purple background.

Jim and Olu as Tybalt and Mercutio from the iconic 90s Romeo and Juliet movie #OFMD #OurFlagMeansDeath

Them. #OFMDfanart #ourflagmeansdeath

Ed being run through by Stede saying 'didn't mean to moan like that my bad'

I just missed this meme

Self-care day, everyone! Remember to take care of yourselves. xo
#OFMDfanart #ourflagmeansdeath

Stede is behind Ed, railing him into the mattress of their four-poster bed. His skin is flushed and he's kissing Ed's back, panting heavily with the effort. Ed is splayed out underneath Stede, hair loose and falling over his arm and onto the mattress. He's gripping the sheets tightly with his hands. A speech bubble reads "Oh fuck, Stede- Yes! I love it." Ed has a tattoo on his butt that says "Booty or Bussy."

Stede topping Ed. If you like that kind of thing.
CW: NSFW cartoon pirate smut
#OFMDfanart #OFMD