AddictedtoDoublefedora
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Summary
Chance is challenged by ITrapped in a bet: dress up as a woman and seduce the leader of the wealthiest mafia family in the city: Mafioso—otherwise known as Don Sonnellino. If he manages the challenge successfully, he will be rewarded bountifully by ITrapped and potentially scam Mafioso’s money.
Being a nitwit when it comes to women, how will he overcome this daunting challenge? Will he be a convincing actor? Will he be able to succeed and enjoy a life of endless luxuries, or get found out about his true identity and face the major consequences of angering Mafioso? Let’s find out!
Bookmarked by AddictedtoDoublefedora
08 Jul 2026
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The lucky gambler of Grog & Galleon Grange went missing, and so The captain of La Zanna Nera set sail into the sea in search of his lover. Refusing to move on and accept the death of his lover, he is unable to acknowledge what he has found is not his lover, but a siren in disguise, a known mythical monster of the sea.
A story of grief and mourning awaits.
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Or Doublefedora Pirate / Siren AU!! #TSTSMLA_AU
@jackpowt on tiktok and @anhuanx on twitter!!
Get back to writing, AoiBookmarked by AddictedtoDoublefedora
18 Apr 2026
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Summary
Warning mischaracterized
Eight years have passed since Chance and mafioso, once inseparable childhood friends, were cruelly separated by fate. A sudden tragedy claimed Chance's father, and on the same day, mafioso's family was forced to flee their hometown due to their mafia ties. The boys, both ten years old, exchanged a hurried goodbye, unaware it would be their last for a decade.
Now, mafioso has returned to his birthplace on a mission to dismantle a dangerous drug ring for his mafia family. As he arrives, he spots a missing person poster featuring a man named Itrapped around his age. Though the pictures of a guy named "itrapped" missing, mafioso can't shake the feeling that destiny has brought him back for a reason
Determined to complete his mission and perhaps reconnect with his long-lost friend, mafioso delves into the underbelly of the town he once called home. Little does he know that every step brings him closer to uncovering secrets that will forever change the course of both their lives.
(Ichance happens at chapter 11 for those who want to read ichance. Also where chance is the main character and explore their "friendship". wrote this like the game "life is strange" since it's a childhood I loved)Bookmarked by AddictedtoDoublefedora
05 Apr 2026
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Summary
Warning mischaractzion
Chance was frustrated after being blacklisted from his favorite casino, owned by the infamous Mafioso. Despite the ban, Chance couldn't shake off the allure of the games and the thrill of the chase. He came up with a bold plan: disguise himself as a woman and sneak back into the casino. But this wasn't just any disguise - Chance wanted to stay respectful and elegant while pulling off his daring heist. He spent hours meticulously preparing his disguise, ensuring his clothes, hair, and makeup were perfect. With a deep breath, he stepped into the casino, hoping he could fool the watchful eyes of Mafioso but not the unexpected outcomeBookmarked by AddictedtoDoublefedora
10 Apr 2026
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Summary
Warning- mischaracteriton and different au
Mafioso thought he had it all—power, connections, a reputation that made men quake in fear. But when he received a mysterious letter claiming Chance had paid off his debt, everything changed.
What was the real reason he did it? How could a reckless gambler pull off something like this? And more importantly, what did he want from Mafioso in return?
The truth is more complex... and potentially dangerous... than either of them expected.
Bookmarked by AddictedtoDoublefedora
06 Apr 2026