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Izzy has never had an orgasm, but Frenchie has an idea.
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The Well Dressed Gentleman. by jammedWriter, Trashdog13
Fandoms: Our Flag Means Death (TV)
31 May 2026
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DressLikeAGentleman is a faceless ASMR TikTok account focusing on the quality of clothes and the care of dressing well.
It is also some of the most blatant, though unadvertised, fetish content that Izzy has ever seen. The editing alone is enough to cue anyone in to whats happening, the constant close up on the narrators hands, the way he handles every tie or scrap of fabric, his voice.
Izzy watches it every morning. It’s inspired him to branch out his style, to work up the courage to explore outside of his usual black outfits.
He never expected to hear The Gentleman's voice in real life, placing an order at his local coffee shop.
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Roach discovers that Izzy’s bad moods are caused by pent up arousal! Thank goodness the doctor is here to help…
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Sequel to “Tight Squeeze,” but you don’t need to read that to get the gist. :)Series
- Part 2 of Doctor’s Orders
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Izzy was lucky, all things considered, that Stede waited until he was definitively over 18 before starting his assault upon Izzy’s sanity. But just because Stede was legally an adult didn’t mean it would be right for Izzy to look at him like that. It wouldn’t be.
Izzy’s 18-year-old neighbour Stede calls him over with an emergency that turns out to be a farce to get in his pants. Izzy has also seen Stede through his window, dressing up in femboy outfits and opening packages with giant dildos in them. Can he really go ahead with this?
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[Podfic] got chains at your door (and need a release) by Meomyr Pods (Meomyr)
Fandoms: Our Flag Means Death (TV)
26 May 2026
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Podfic of got chains at your door (and need a release) written by shatteredhourglass.
“You fucking dickheads,” Izzy says. “I’m going to lock you out of the apartment and let you rot outside.”
“Ah, you’ll be fine. Just… keep ‘em occupied for an hour or two,” Jack says, shoving at Ed’s nonexistent ass as he tries to squeeze through the window.
God, he hates them both.
Audio length: 0:56:31
Bloopers begin at 55:41, and includes one of my all-time favorite conversations with my cat.
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Izzy should kick him out. But maybe tonight he doesn't want to.
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old scars / fresh blood by florence_after_midnight for screamingCockroach
Fandoms: Our Flag Means Death (TV)
28 Mar 2026
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To save Edward's life during the raid on Calypso's Birthday, Izzy gives himself up, reuniting with his long-lost flame.
“But we’re in luck,” Ned goes on. “Fate has led us back together, and no one can take that from us.”
Izzy isn’t sure whether to be relieved or terrified by the statement. No one’s coming to save you, Ned could’ve said just as well. -
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PLEASE PLEASE PLEEEEASE GO READ THE WORK THIS IS INSPIRED BY IT'S ACTUALLY SO PEAK
"It was an honest mistake, really. At least- it was at first.
I don't think anyone expected Izzy to walk into the captain's quarters and see.. that.
What was that?
I'm glad you've asked."
Or Edward and Stede are absolute freaks and decide to include Izzy in their games. Not the smartest move.
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"So, as any good first mate would do, when he had the chance he locked himself in his quarters and shoved down his far-too-tight leather pants."
Or, Izzy jerking off after a particulatly frustrating day under Blackbeard's rule.
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A short exploration of Izzy's feelings as he watches Ed and Stede court each other.
note: Izzy being trans doesn't come up in the story in any way but when I write him he's trans so now you know that.
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Taking place right after “Most Ardently”, Izzy and Stede get married. After doing so, Izzy is free to come into himself.
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- Part 2 of Most Lovingly
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Inspired by Con O'Neill's "send scissors" selfie and the author's own need for a haircut. Izzy thinks he needs a haircut. Jack wants him to keep the fuck handle.
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Almost two years removed from an abusive relationship, Izzy finally starts dipping his toes back into...well, Life, really.
Jackie decides to Help
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Izzy and Ed have been teetering on the edge of something more than friendship for months, though neither of them have ever addressed it head on. One night, when they’re laying side by side on their mattress on the floor of their little apartment, that finally changes.
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business dinner by florence_after_midnight, lovedhands
Fandoms: Our Flag Means Death (TV)
14 Feb 2026
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“Going to have to put you in nappies, aren’t we?” Izzy suggests, but it lacks the teasing tone that comments like this usually carry. Stede actually considers it this time.
“Maybe,” he murmurs. He likes the idea of them taking care of him like that.
“Why don’t we give it a try?”
After Stede has an accident while doing chores, Izzy introduces a solution, on which Stede becomes much too reliant.
Series
- Part 14 of blackbeard & basilica’s boytoy
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When Stede is made aware that Izzy likes rutting off while on the verge of pissing, he wants to witness it
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- Part 5 of Stizzy Piss Kink
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Izzy feels trapped being seen by society as a woman. The visiting Lord Stede Bonnet proves to complicate things further.
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- Part 1 of Most Lovingly
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Izzy got hit with a truth serum. When Fang comes to deliver him dinner, Ed is right behind him.
Seeing as Ed just found out about Izzy’s huge, pathetic crush on Fang, this can’t be good!
(Izzy is tricked into telling Fang all the nasty things he wants Fang to do to him. Thankfully, Fang is into it!)
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Written for the Three Sentence Ficathon. Prompt: three sentences without using the letter "e" besides in character names (Or, the one where identity blurs the night of Calypso's Birthday.)
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Where were you? How are you? You smell different. You look the same. I’ve thought of you every day since my life began and I’ll never grow tired of it. Did you miss me? Do you love me?
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Edward comes home.