AI Sissy Companion
YOUR DREAM AI SISSY
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Pick her looks & bodyUncensored sissy 24/7She remembers everything
AI Sissy CompanionAI Sissy Companion
Build Your AI Sissy Companion
Design your perfect sissy partner and live every feminization fantasy.
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Pick her looks, body & personalityUncensored sissy chat & roleplay 24/7Remembers you across every session

HTML Prison

Prison
Version: v0.40D1 Developer: The Red Artist · Patreon · Discord Updated: 2026-03-23
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AI Sissy CompanionAI Sissy Companion
LIVE ANY SISSY FANTASY
Build the sissy, set the scene, live your exact feminization fantasy.
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Any look: cute, slutty, submissiveAny kink: chastity, training, forced feminizationRemembers every session

About this game

Prison follows Jacob, a 21-year-old who made a string of bad teenage choices and ends up behind bars. The game is an HTML adventure where the player has to keep him alive and intact in a hostile environment that is anything but interested in either.

The AI CG art carries the look. Sissification arcs, blackmail, bukkake, corruption arcs, dilf encounters, drugs, exhibitionism, futa/trans, gay routes, groping, group sex, and humiliation themes all factor into the prison's daily life. Anal sex sits at the center of the encounter design.

Still in development at v0.40D1. If you want a prison-setting sissification game with HTML accessibility, real survival pressure, and a male protagonist whose dignity is the resource everyone is trying to spend, Prison commits to that mood without sanitizing the setting or rushing the corruption arc.

Changelog

v0.40D1
Highlights & New Content Updated main cover – fresh new look! Added hyperlink to Rule 34 on the start screen. +12 new passages – 9 of them containing adult content 2 new shower scenes – auto-trigger if femininity is low & reputation is negative +7 new Darius scenes – discoverable by: Play the RPG → Go to the forest → Sleep in the forest Next day → Visit the library → Darius will appear Game Stats Total passages: 721 ️+44 new GIFs, over half created by me New character interaction (besides the cover) Started converting GIFs to WebP for smaller file size Notes Game guide not updated yet with these new changes In-game changelog updated (0.40d → 0.40d1)
v0.40D
Sasha’s Prologue Added You can find it directly in your cell. +12 new passages +43 new images/GIFs (Atmospheric story content fully integrated into the main narrative.) Nerd RPG Route COMPLETED The entire route is now fully playable from start to finish. ADDITIONAL CONTENT +10 new passages across the main storyline, intermissions, and supportive scenes. +37 new GIFs added to the spin-off. New RPG total: 100 GIFs (a new milestone!) 7 new joint character portraits to enhance immersion and dialogue expressiveness. FIXES & IMPROVEMENTS Fixed the duplicate-initialization bug that appeared the first time the RPG started. Minor visual consistency tweaks and narrative flow improvements in existing scenes. v0.40C3 New NPCs & Portraits 3 brand new NPCs added 26 NPC portraits, 21 actively used Several animated portraits 2 variable portraits of Jacob (femininity > 10) Vision feature: scenes can have “double layers” for unique experiences RPG & Scenes Text-based RPG with GIF integration 9–10 scenes with multiple variations: Bathroom scene with changes on second pass (reuses GIFs) Interactive “late afternoon library” sequences Sissy scenes included A touch of hypnosis Interracial content included Future content hint: some scenes give a sneak peek of what’s coming next GIFs & Animations ~65 images/GIFs embedded in events Multiple animations for NPCs and key scenes Total of almost 100 new items in this patch Bug Fixes Fixed a variable error in “hanging out with Sasha” Fixed misaligned text in cell hangout Updated the Nerd section in the guide Sneak Peek for Next Patch Possible ally NPC introduction Rework of location images Visitor’s room overhaul Introducing family members Global patch with all types of content Summary Checklist 3 new NPCs 26 NPC portraits (21 used) 31 portraits total (including animated and variable Jacob portraits) ~65 GIFs integrated into scenes 9–10 scenes with variations Text-based RPG sequences Vision/double-layer feature in scenes Sissy scenes & hypnosis content Interracial content Bathroom scene with second-pass variation Bug fixes (3 total) v0.40C2 Global Interface Changes Updated sidebar style for all stat displays. Replaced the old sidebar title with a fresh animated one (the old one felt too plain). Renamed the browser tab for better consistency. Global font style adjusted to match the penitentiary atmosphere. Inmate dialogue font improved for deeper immersion. “Sissy” font style tweaked to feel more feminine . Polished text formatting across multiple sections. Added 9 semi-animated emojis ✨ ️ New Scenes + Spicy Changes Blackgang kitchen scenes now available! Early morning cafeteria shift – Mondays and Fridays. Requires 30+ femininity and having surrendered to the Black man in the showers Paying Sasha on Mondays no longer advances time! ️ Fixed a replication bug in the Latino cafeteria work (early morning shift). 9 new animated portraits added! 1 NPC-to-NPC interaction portrait – the first ever in game history! Possibly... a new item? 2 work introduction scenes: 1 if you haven’t met Tyron. 1 reused/adapted if you already know him. 18 new scenes (16 new passages with internal variations). ️ +77 new GIFs: 18 repeatable scenes 20+ scenes with branching options Includes 1 hidden/secret scene with a special variable that ties into the next patch… Will you catch it? The guide is now updated and gives hints on where to find all the scenes and how to reach level 70 femininity. I’ve been replaying my own game during these days off and… yeah, I’ve finally seen why many of you aren’t reaching 70. Having to wait for Sunday and relying on the stepfather scene, which is random, makes it easy to miss — especially if you’re not going backwards. So, I’ll need to rework the visitation area. Aside from that, the guide not only shows where the scenes are, but also includes most of the characters, and within their entries, you’ll find the description Sasha gives you in your cell, in case you found that exciting or were curious about it. v0.40C1 Fixed the redirector to the visiting room to properly display the chef's scene. Fixed a bug that allowed you to go directly to the football field and meet the Latin gang without having the altercation in The Yard. Fixed a gap in the "lowering your head" section when talking to Ismael. Deleted 9 passages that no longer made sense (see point 2). Now, if you met the Latin gang during the first encounter, on the second day (emphasis on the second day), you will get a unique scene that leads directly to the football event. (New unique scene with no adult content and a new portrait.) The option to resist from the start is now available if you don't lower your head and select the "You talk too much" option. Otherwise, you will only have the option to submit—consider this a warning. New scene leading to meeting The Jackal from the third day onwards if you submitted to the Latin gang while playing football. When you step into the yard, it will now redirect you accordingly. New animated portrait of The Jackal. Fixed coding errors in the kitchen with the chef. New job options added for Tuesday and Thursday if you've reached the second scene with the other prisoners in the chef's room and if femininity is above 30. First breast transformation event redirected (see point 7). Introduction of another character in the kitchen. IMPORTANT: A solution has been found to ensure that saved games will now work despite variable changes. +56 new sexual GIFs. Related to point 10... +18 new passages. Out of these, 16 passages contain repeatable adult content with interconnecting elements. 17 These events change depending on your actions at different tables—find them all. Due to the previous point, this section is now replayable for several weeks. New animated location GIF. 20 The second stepfather event now triggers automatically when you enter the visiting room. Smoothed out the chef’s money flow to accelerate transformation progress and set up future updates.
v0.40C
The event where the chef whips you for being with the Latin group now triggers automatically when you enter the Cell. The text where the chef is sitting on the bed has been adjusted to appear after the previous event, ensuring both new players and returning ones know where the scenes occur. Scenes involving makeup and similar activities now have updated text to clarify where they take place. When your femininity surpasses 20, aside from the event with Sasha, if you've also succumbed to the nerd, he will now be sitting at one of the tables in the cafeteria. (New scenes with him are coming, and I may also focus on reducing intelligence from there.) In other words, there will be an additional "food" option available in the cafeteria during the afternoon. 16 new passages—over half of them include adult content. Be cautious, as several of these alter reputation and fame. Additionally, if you have more than $50, Jacob’s wallet might take a hit. +49 new sexual GIFs created by me! New portraits—I'm sure you'll love them! A total of 8 animated portraits have been added. Two new items added. And all of this can be found in the afternoon at the cafeteria during lunchtime if you've followed the entire sissy route. v0.40B3 Visual Rework: Visual improvements have been made to the game for a smoother and more attractive experience. New Left Sidebar Interface: The left sidebar has been redesigned to improve navigation and organization of menu options. New Text Blocks to Differentiate Characters: New text blocks have been added to clearly and dynamically identify and differentiate the characters. Fixed Code in Several Events: Bugs in several events have been fixed to prevent execution issues. Fixed Several Events for Coherence: Events have been reviewed and adjusted to ensure that the narrative flow is coherent and consistent. The Vito Assault Event Will Occur on the Eighth Day If Your Reputation is Broken: The event where Vito assaults you will now only trigger if your reputation is broken, and it will happen on the eighth day of the game. You Can Now Surrender to the Nerd Alone Without Going Through the Chef, Following a Gay Route with Vito, Tyron, and the Nerd: The option to surrender to the Nerd directly, without going through the Chef, has been added, activating an alternate gay route with Vito, Tyron, and the Nerd. Reprogrammed Sasha’s Dominance Events Regarding the Nerd and the Chef: Sasha’s dominance events have been reprogrammed to be more direct and occur when returning to the cell, without the need for previous events. The Event of Washing Sasha’s Underwear is Now Available During All Time Slots Except Mealtime, Evening, and Night: The event related to washing Sasha’s underwear is now available during most time slots, excluding mealtime, evening, and night. Sasha's Route Is Clearer with Work Options in Multiple Time Slots: Sasha’s route has been optimized, now offering more work options when returning to the cell during different time slots, overlapping with M/M sub-content. Vito’s Subordinates in the Cafeteria Will Assault You After Vito Has Already Done So (Decline Option): Vito’s subordinates in the cafeteria will now assault you after Vito’s assault event, especially when the decline option is chosen. The Wardrobe Button No Longer Has Disproportionate Images: Disproportionate images on the wardrobe button have been corrected, resizing them for proper display. Descriptions Are Now Expandable to Avoid Excessive Scrolling: Event and character descriptions are now expandable, eliminating the need to scroll excessively to read the full information. Changed the hyperlink color to a less intense blue with underlines. +3 new character portraits +65 gifs +19 new passages/scenes, of which 16 are repeatable +New femdom event with a new character (novelty) +The scenes are located in the backyard throughout the day, except during the afternoon and late afternoon. You only need to have negative reputation and femininity below -30. +Content includes m/m sub, shemale on male sub, femdom, shemale group sex, etc. You will see. v0.40B2 +21 new and repetitive scenes, +16 of which are erotic.+2 variatons of text of hidden variable (so 18) You can find these scenes in the group activities in Vito's cell. +61 GIFS +Partial narrative changes to the scenes. +1 new item. +1 new portrait. +6 Use of Hidden Variables ( Care.) v0.40B1 +56 GIFS +6-7 Portraits +1 Item +Fixed text ( Was in Spanish) +8 repeteable M/M sub scenes +1 Intro scene +4 Hidden Variables ( Care.) v0.40Apart2 +113 GIFs +5 Portraits +3 Items +Fixed Wardrobe +Guide Introduction +26 New Repeatable Sissy Scenes in the Cell (You just need to have +30 femininity and have been dominated by Sasha regarding the chef and the nerd (This is the most significant update of the game) Thank you for being patient with me and for continuing to support this project. Tomorrow or in a couple of days, I will post the plans I've been working on. I hope you enjoy this update! I believe it's one of the most content-rich updates I've released. And that's it—here's the link -> v0.40APart1 +40 new gifs. +10 Scenes on your cell to pass time but you need to submit to Sasha just in case Only 9 m/m Sub for now. and 1 sissy. +Fixed some bugs of reputation/fame +Fixed some typos
v0.40
+22 new gifs +8 scenes on Sundays... in the morning at the new location (church) +2 New character introductions: the first will appear at the beginning of the game, the other on Sunday morning +1 new functionality: now you'll see the steps of the day cough cough +3 new portraits of locations +8 new portraits of characters +2 new descriptions of characters +2 new descriptions of locations
v0.39D
+30 gifs created by me +6 scenes in the backyard in different time slots if your femininity is 30 or higher(1-Chef(Late afternoon),1-Tyron(Early evening),2-Vito Minions(Morning),1-Ismael(Morning),1-Nerd(Early Evening)) +2 new portraits +55 image errors in Google Chrome fixed.
v0.39C
+ Provisionally done with new backgrounds. +Fixed several image and text errors + 27 new GIFs potentially going up to 30 with new forthcoming scenes + Previous saves should work(V.39B SAVES) but better to start a new game. + All backyard scenes set for different times of day and are only unlocked depending on who you've met. (Tyron, Nerd, Chef, and/or Vito). v.039B + Fixed: If the bald prisoner assaults you and you hadn't unlocked Ismael's cell, you will no longer be redirected there. + Fixed: Adjusted variable where Ismael doesn't offer options for feminization; reduced to 5 femininity to make initial options appear. + Fixed: Error where Vito appeared in the cafeteria at any time, which could break the game. +20 new gifs made by me. +7 portraits. +5 character variables. +2 potential storylines for new characters. +New jobs for Tyron in the backyard in the late afternoon to acquire components. +8 repeatable random events, 4 m/m sub of which 3 have erotic content, and 4 sissy of which 3 have erotic content.
Installation
1. Extract and run.

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