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352 results · page 9 of 15

  • Mavery
    ChubBotbooru

    Mavery is your new cellmate, and the perfect toy to break in the eyes of the evil inmates at Blackridge Correctional.

    1,992 tokens

  • Grax
    Rasus67
    Chub

    Fighting, Violent start, Hostile Setting, Mention of crimes, Blood

    1,167 tokens

  • Community Punishment Program
    badder_dragon
    ChubBotbooru

    [4 Greetings] Everybody's always talking about prisoner reform and the justice system. Well, the new Community Punishment Program revitalizes it all through systems of humiliation and deterrence!

    1,429 tokens

  • Female Futuristic Prison
    byPeking
    Chub

    An all women's prison set in the future. Stay imprisoned or break free.

    3,314 tokens

  • Leslie
    Fortani
    Chub

    Leslie is stuck between a rock and a hard place - the hard place being his dick. He's a prisoner sentenced to work as a miner in a Penal Colony. Being around sweaty, hunky men all day means he'll be forced to face the feelings he denied...…

    1,809 tokens

  • Ryoma Hoshi
    Jidoct
    ChubBotbooru

    Danganronpa V3: Killing Harmony Ultimate Tennis Pro

    1,922 tokens

  • Nathan
    Nopeoz
    ChubBotbooru

    An official fork of my Femdom World bot, now taking place in the Futadom World. A much more dangerous world, but so is Nathaniel… You and your fugitive partner are the on the run and trying to survive in a dystopian world. You two are the…

    3,296 tokens

  • Michael myers (camp counselor au)
    meek_watch_85467
    Chub

    Michael myers (camp counselor au)

    473 tokens

  • Diena
    bynurze0
    ChubBotbooru

    (Update: 1/31/2026) FORK - Diena Dodger, a pit bull on death row, has taken a liking to you over the last few months. On the day before her execution, a storm rages outside the prison, and the power goes out. Lucky her.

    1,879 tokens

  • Benjamin Netanyahu
    RealNiqqa
    Chub

    “Benjamin Netanyahu is captured. But what punishment could ever be enough?”

    2,106 tokens

  • Casey
    EverNever
    Chub

    Earth soldier enslaved in a fantasy empire where magical brands enforce obedience, but she files every violation and believes her husband is still looking.

    3,262 tokens

  • Bratty Elf Captive
    max1199
    Chub

    A spoiled and haughty princess prisoner.

    266 tokens

  • Rye
    Cloptimus
    ChubBotbooru

    Rye was a blackmail victim of Tara Kane, now she takes smug satisfaction seeing her former tormentor in the glory wall as punishment for her crimes.

    2,191 tokens

  • Bradley
    Fortani
    Chub

    [3 Greetings]Welcome to FCI Shem - a medium-security prison where the Warden just so happens to be a power-hungry and domineering perv. Will you resist the Warden's advances, or will you take the easy road and submit?

    1,972 tokens

  • Sarah
    bleachbunny
    ChubBotbooru

    ♥️ 25% You're a guard watching a high-profile prisoner. A boring night shift, until you receive a surprise visit from the DOJ.

    3,449 tokens

  • Amy
    Cloptimus
    ChubBotbooru

    3 Greetings! Amy Rose is trapped and humiliated in a filthy cell, clinging to her fiery spirit as her last defense against despair.

    1,593 tokens

  • Allen
    ScragglySchrongleREVIVED
    Chub

    A guy sentenced to both being in prison… and being feminized! Artist: pink horizons

    691 tokens

  • Bruce
    AnotherOriginalName
    ChubBotbooru

    this is an old bot that I never made public oh, and uh, replace the underlined words with whatever racial slur applies to you

    1,317 tokens

  • Nia
    ass_lord
    Chub

    Behind her angelic face lies a predatory psychopath. Nia is a wolf in sheep's clothing—a nymphomaniac who collects beautiful people like trophies to satisfy her darkest, most explicit desires

    2,929 tokens

  • Ashley
    byalert_gene_6525
    ChubBotbooru

    { {“{{char}} full name”: [“Ashley”] } [You were browsing the internet, looking for online purchases, when you saw an advertisement for a website called "Horny Inflatables" that sells inflatable women, but as if they were real. Upon…

    1,451 tokens

  • Tier Harribel
    TheCharcoalWizard
    Chub

    After Yhwach invaded Hueco Mundo, Tier Harribel confronted him alone in the throne room of Las Noches to protect what was left of her kingdom. She released Tiburón and attacked with everything she had. It didn’t matter. Yhwach defeated her…

    2,444 tokens

  • Azula
    BillyBunz
    Chub

    She once was a Princess of the Fire Nation, and once a Fire Lord, now imprisoned...but she was sentenced that's even worse...or better!

    1,064 tokens

  • Trandulsia
    Fortani
    Chub

    You've been sent to Trandulsia - an island designed by the Emperor to house the degenerates of the Empire and keep them away from 'proper' society. How you ended up here - who knows? But you're here now, for life, and you'd better get used…

    2,497 tokens+2 forks

  • Itucola
    Fortani
    Chub

    You've been sent to Itucola - an island designed by the Emperor to house the degenerates of the Empire and keep them away from 'proper' society. How you ended up here - who knows? But you're here now, for life, and you'd better get used to…

    2,491 tokens