Jackson | Sapphires Holiday Heal Fest 💙
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ourflagislove.bsky.social
Jackson | Sapphires Holiday Heal Fest 💙
@ourflagislove.bsky.social
350 followers 520 following 1K posts
“Don’t Walk, Fly!” - Con O’Neil 🖤🦄

Jackson, 27, He/they, Pan, Trans, Autistic, ADHD,

GCC Forever 🫶🏼

Steddyhands 🖤

18+ only please
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ourflagislove.bsky.social
Jackson | Sapphires Holiday Heal Fest 💙 @ourflagislove.bsky.social · Dec 7
This has been the most amazing night of my life. I love this life, it’s so special and beautiful and full of good and amazing things. The world is ours to spread love throughout. ❤️

@therealcononeill.bsky.social you are such a beautiful soul, thank you for your kind words of encouragement. ❤️🦄🏴‍☠️
Con O’Neil and myself, at the one last song drag show in Columbus Ohio. I have on the “it’s about belonging something” shirt and con has on a brown leather jacket with his arm around me.
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
ourflagislove.bsky.social
Here is A very sweet photo i got of @vico-ortiz.bsky.social and @therealcononeill.bsky.social at GCC 🫶🏼
Con is holding Vico close as he shows them a jar of shimmer. Con’s back is mostly to the camera but you can see Vico smiling. The photo is in black and white.
December 12, 2024 at 8:00 PM
ourflagislove.bsky.social
Just love 😌🫶🏼
words Gavid enkinsoskysoclal every pretty worlds thank favorite think finally es ive season watch drop made days say today watching agan gcc okay ill back chapter asked cant sessed ee world N fcCOnB even enjoy excited know start wheni see give yall first life group au trans episodes seen dont ohio everyone UST S egonna few getting saying oneil david boys stede Sn. a no 0 having share tell time W photo • use rogether mind crush please actually play freind uoud right amazing D anyone hello pos really & friende read day change love beautiful cause question) maybe thought others pirate picture support bskyinsights.com
November 27, 2025 at 6:19 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
akans.bsky.social
Aaand here's the other STILL VERY NSFW illustration for the fic, from chater 5! 💜👀🧡
I'm still giggling and kicking my feet I got to draw unhinged stuff like this, this time (compared to what i usually draw lmao) >:D Absolute blast 👌
#ofmdfanart #ofmdnsfw #OFMDBB25
Explicit illustration of Stede thorougly appreciating Ed's assets. Ed is sitting on the edge of the bed in just a skirt, lace panties and ripped fishnets. Stede is kneeling between his legs, having just been done blowing Ed, stirng of spit still connecting his mouth to Ed's dih
November 27, 2025 at 1:00 AM
ourflagislove.bsky.social
You've been kidnapped. The characters from the last TV show you watched are trying to rescue you. Who's coming to save you?
November 26, 2025 at 1:54 AM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
akans.bsky.social
It's Big Bang time again! It's here!!!
Got the pleasure (heh) of working with the wonderful @lizzyleo.bsky.social on a couple of VERY NFSW illustrations for her BB fic, alongside @samwtf.bsky.social 🧡
You can zoom in on this one as much as you like in chapter 2 >:3c
#ofmdfanart #ofmdnsfw #OFMDBB25
Explicit illustration of Stede enjoying one of the toys. He's laying naked on his bed, hand gripping the sheets and head thrown back.
November 25, 2025 at 10:14 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
citrussyndicate.bsky.social
🎵 If you don’t ask then you’re bound not to get 🎵

@alexis44.bsky.social commissioned more western boys and, y’all, I LOVE more western boys!!
A digital drawing of a Stede Bonnet and Edward Teach from Our Flag Means Death dressed in western wear. They are sitting on brown wooden stairs, with Stede situated between Ed’s legs. They are holding hands. Stede is wearing a teal and white western shirt, jeans, and black boots. His eyes are closed and his head is leaned backwards with his face looking up towards the sky. Ed is wearing a purple tank top, black jeans, and black boots. He has his eyes closed as well while face is pressed into the side of Stede’s face. The sky in the background is dark blue with stars sprinkled across it.
November 24, 2025 at 2:36 AM
ourflagislove.bsky.social
theinnocencetest.com
Rebel (26) you're getting there, but you're definitely just beginning to experiment with your wild half. welcome to the dark side, love, it's a fun place to be.
November 24, 2025 at 2:50 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
citrussyndicate.bsky.social
Y’all, Ed ended up looking like a snack and a half in this drawing I did for @ladypenni.bsky.social

I basically need her to stand over my shoulder every time I draw Ed because 😮‍💨

#OFMDfanart #OFMD
A digital drawing of Edward Teach from Our Flag Means Death wearing most of his leather outfit, minus a shirt. He has a short beard and long windswept hair. He’s posing with one arm over his head and his jacket hanging off the opposite shoulder. He’s making very hot eye contact with the viewer.
November 24, 2025 at 12:41 AM
ourflagislove.bsky.social
Hello friends! Would any of my fellow trans folk be willing to talk with me about what to expect as I start my chest surgery journey and anything I should know that maybe you wish you had known ahead of time? I have my initial consultation in a few days and I have no idea what to expect. 🫶🏼
November 24, 2025 at 1:34 AM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
rysi000u.bsky.social
OHHHH👀 IS THAT,,,
November 23, 2025 at 9:57 PM
ourflagislove.bsky.social
This is your sign to get a group of friends together and watch A Very Jonas Christmas Movie for some good vibes and laughs.
November 23, 2025 at 12:39 AM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
babykittenteach.bsky.social
09/05/24
Sketchy drawing of Ed Teach from behind as he's kneeling in his leather pants and short purple shirt, bound in shibari style ropes.
November 14, 2024 at 5:58 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
unfortunatalie.bsky.social
Not saying I would be caught by sirensong but I would definitely crash my ship straight into a rock if I heard this
twigtechnology.bsky.social Michael Haslam @twigtechnology.bsky.social · 6d
Seals singing in a sea cave

#Orkney 🦭🎧
November 21, 2025 at 11:39 PM
ourflagislove.bsky.social
STOP. This is a selfie checkpoint, you must repost with a cute selfie to proceed.
A photo of myself I have on a black and grey flannel and a black shirt that says pirate life with a skeleton Blackbeard on it.
November 22, 2025 at 6:24 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
rebelsophie.bsky.social
You’ve heard of Black Friday? Well this is BLACKBEARD FRIDAY (and friends!) an Etsy sale of a few Original Acrylic OFMD paintings 🏴‍☠️💖

www.etsy.com/listing/4409...
November 22, 2025 at 3:40 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
gelatinousstand.bsky.social
Today's the daaaaaaaaay!

Please enjoy No Shenaniganry Allowed Aboard Jeff's Inn on the Sea, my Big Bang with @pogonr.bsky.social. Fake dating! Lots of pining! Extreme silliness! Smut! Ed and Stede being idiots for each other! Gorgeous art INCLUDING trademark sloppy smoochin! 💖

Enjoyyyyyyy 🥰
No Shenaniganry Allowed Aboard Jeff's Inn on the Sea - Chapter 1 - Juniper (GelatinousStand), pogo - Our Flag Means Death (TV) [Archive of Our Own]
An Archive of Our Own, a project of the Organization for Transformative Works
archiveofourown.org
November 20, 2025 at 3:54 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
aloc.bsky.social
it's very cold indeed, hate colldddd🥶
November 18, 2025 at 2:36 AM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
serpentanddahlia.bsky.social
Feeling a little guilty* about all the mental devastation lately so in case anyone needs a RWYLM palate cleanse, for #TakeTwoTuesday I present Off the Deep End -- my very silly, low angst RBB collab with @sailorsruin92.bsky.social

*not THAT guilty tho😌

archiveofourown.org/works/671108...
art by @sailorsruin92 to accompany my fic, Off the Deep End. A comic in 5 panels: 1. Edi sitting in a poolside lounge chair, his legs crossed. He has on blue swim trunks, sunglasses, and pink and slides. He's just spotted Stede (in the foreground) who is taking off a yellow swim cover to reveal a mint green speedo and freckled/sun burnt shoulders 2. Stede tucks his hair into a bright red swim cap. Ed leans into the corner of the frame, watching Stede and looking love struck 3. Stede dons a pair of mint green goggles (to match his suit) 4. Stede dives into the pool 5. Ed watches Stede diving in the other frame -- Ed's glasses are tilted down his nose and he has hearts in his eyes, a hand held to his chest. He is in love. More art by @sailorsruin92: Ed in black swim trunks and his pink slides, wearing sparkly purple swim floaties on his arms in front of a pastel purple background dotted with sparkle stars and hearts
November 18, 2025 at 8:50 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
ourfag.bsky.social
as promised
A black and white digital drawing of Ed from OFMD lying on his back, playing with his t-dick and teasing the entrance of his hole with one of his hands; the other one is supporting his head while he makes fuck-me eyes at the viewer. He’s got top surgery scars and full bush. And pit hair. In case you’re into that too.
December 12, 2024 at 1:46 AM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
edteachsbadknee.bsky.social
did somebody say hot butch oluwande? (ref from trueref !!)
a digital drawing of Oluwande with their hand on their head and one foot propped up, as if they’re resting while doing some sort of activity. They’re wearing a teal tanktop, baggy cuffed jeans, their signature beanie, and magenta crocs. They’re wearing a have an orange fish keychain with some keys on a carabiner on their belt loop, and they have garlic bulb and soup love heart tattoos. The drawing is shaded in a slightly washed-out watercolor style.
November 16, 2025 at 10:51 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
yearofbelonging.bsky.social
The artists for this calendar will captivate you with their use of light & color. Like @sensationseekng.bsky.social

A Year of Belonging, a calendar for charity.
Pre-order through November 19!
yearofbelongingcalendar.bigcartel.com

(Showcasing some of their OTHER artworks here.)
Izzy forgot he was messing with a master tactician. Big romantic kiss between Ed and Izzy with dramatic gold lightning. Ed is holding Izzy's face and Izzy's arms are kind of stuck out behind him like the kiss took him by surprise.
November 16, 2025 at 1:29 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
sweetpotato69.bsky.social
👅🍆💦
Stede in view from chest up, on his knees in front of Ed with his tongue out, looking up at Ed through his lashes. Ed is visible from stomach to thigh, pants undone and pushed down slightly, resting his cock on Stede’s tongue with one gloved hand and holding the side of Stede’s head gently with the other.
November 15, 2025 at 5:05 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
sweetpotato69.bsky.social
You send him a drink and fire him on the spot 🍹🍆💦
Stede looking cheeky slurping on a large cocktail with a little umbrella, wearing a silky teal shirt and curls perfectly in place
November 15, 2025 at 5:05 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
sweetpotato69.bsky.social
what do you do if this is your therapist?

archiveofourown.org/works/46498615

🧵
Leather daddy Ed Teach leaning back against a bar with a drink in his left hand, right thumb hooked in the waistband of his leather pants and hand resting against his hip. He has a full beard and loose hair and is wearing an open leather motorcycle jacked with a strappy harness underneath
November 15, 2025 at 4:56 PM
Reposted by Jackson | Sapphires Holiday Heal Fest 💙
rysi000u.bsky.social
😳
November 14, 2025 at 11:33 PM