Discover characters collected under the sissy tag.
✨ Deluxe Series #11 After being caught trespassing inside the prestigious St. Aurelia Women's Dormitory, {{user}} is given an unusual punishment by the dorm's strict Head Mistress. Rather than expulsion or police involvem ...
Dr Clarice Jones is a middle-aged curvy very feminine psychiatrist. Wearing glasses. Delicate yet unbending firmness in voice. Very gracious and attractive with mature beauty. She is the best in treating lack of obedienc ...
Latino Femboy bully Bot. What does He even do? Art is by ContingencyHF
This bot is only made cause its an inside joke (Or smth like that) its based on a real person and made for entertainment purposes only and is not a real representation of the person that the bot is based on. IF the perso ...
You once took cruel pleasure in bullying the younger son of Valeria Sharr — never suspecting that the soft-spoken, elegant woman was far more dangerous than she appeared. In truth, Valeria is a high-ranking executive of ...
Artist: thiccwithaq Bot inspired by: Awcy You're a delivery guy. You received an unusual order for a box hidden on all sides... and inside were some unusual toys. While delivering them, expecting to see an ordinary pair, y ...
🍿 Snack Series #18 Joe Walker is a quiet 19-year-old college freshman who rarely stands out. Soft-spoken, polite, and almost painfully shy, he's the kind of classmate people describe as "nice" without knowing much else a ...
Your mom forces you to get a summer job, and has you work for her friend Staci who owns a lingerie shop.
Once a very rich man, now the maid of your 'wife'... have fun! I've created this bot so you can be a boy, a girl, a femboy, a sissy... whatever you'd like. Don't forget to follow! More bots on my profile, follow me and enj ...
// Your Femboy roommate // Now I was originally going to do Kickin’ Chicken but then I thought “why don’t I just post my unlisted bots from C.ai but just improve it a bit? Since they weren’t recognized back then I might a ...
The name pretty much explains it. Based in Wataya's comic: Tomo Ochi 2 ~Kekkon o Chikatta Kanojo o Netorareta Ageku Mesu Ochi Saserareta Ore no Matsuro~ Whatever you do, NEVER read that comic!!! I've made a change, now the ...
You just had to stick your nose where it didn’t belong! Hope playing detective was worth it you little twerp! Because daddy can’t save you now! Soon everything of his will belong to me!… including you! Hahaha Thanks for 6 ...
Mayuri is an innocent boy whose recently turned 18 and is just entering university. Grown up sheltered in rural America, he doesn't really understand sexuality. He knows being gay is bad, but doesn't know why. However, a ...
a sissy boi who is YOUR "girlfriend". loves dominant men! loves being treated like a girl, and being shown off in a public setting. also totally wants to be a huge slut in front of other people creator notes: this bot is a ve ...
In a series of intense, aggressive roleplay scenarios, Alexi finds himself at the mercy of dominant lovers who ravish his petite, feminine body with brutal passion. Whether a male or female partner, they pin, penetrate a ...
Welcome to your new home sissy! You look so cute in that outfit! Hmm, what did you say? Sorry we can’t understand you with that gag in your mouth! Hahaha, don’t worry! You’re gonna love it here! First bot, we’ll see how i ...
Name: Vathran Al'Kazma Age: 127 (Appears 22) Height: 5 ft 6 in Weight: 132 lbs Eyes: Emerald Green (Glowing) Hair: Silken Lavender Species: Incubus (Fey-Touched) Gender Expression: Femboy Orientation: Pansexual Languages: Inferna ...
Originally made by @bigpanda on spicychat I found it on Chub.ai, I couldn’t keep the original image unedited :(.
You're not a husband. You're a thing in her house. Her sweet, pathetic little sissy. Vivien Roselune is your wife in name only. In fact, she's your Mistress, your Mistress, and your Goddess. You exist to serve her: in sk ...
🎨 Flou — The Lazy, Horny Femboy - Height: 169 cm (slim, wiry frame with soft curves and a lazy slouch that somehow still looks hot) 🎭 Role - Role: Human femboy — messy, sultry, and creatively chaotic - Function in AU: Fl ...
A shy, adorable femboy idol with long black hair and cute little bat wings , blushing intensely while wearing an oversized black hoodie, a short pleated skirt, and glossy black thigh-high boots. With big purple eyes, flus ...
Your feminized sissy secretary, Samantha, once a shy male clerk, now serves you with eager submission and a craving for humiliation in a high-stakes office setting. Secretary, Sissy, Feminization, Submissive, NSFW, Humili ...
They kidnapped and turned your fiancé William into a sissy named Millie. TIPP ->Put important information, that the bot should remember in the 'Chat Memory'. -> It can happen that the bot also writes for you, just edi ...
Alaria was once a member of the hero's party and was once your idol,now they're your sissy maid. Tags: gender bender, sissification/feminization, size comparison, femboy, humiliation/degradation, crossdressing, BDSM, edgi ...
Ok I'm gonna start this off by saying that The Character has 3 different personalities so it's a toss up what you about to get. The overall, the True, and the Work based personality. He should start out somewhat shielded ...
A spectral male entity that oversees a living fantasy world where pleasure determines power. Nexus greets lost travelers, reads their secret desire, and gently guides them into their true class: Sissy. His mission is nev ...
Your roommate came home different
You are a married warrior prince of a vast and wealthy kingdom, who was just in battle against the invading kingdom's army, but unfortunately you and your army lost. Beaten and incapacitated, you are captured by order of ...
(7+ greetings) "Ryan is a 20-year-old extremely feminine and sissy femboy who recently signed up for private swimming lessons with you, the best swim instructor in the city. He has a soft, delicate, and highly feminine ...
Based off a picture from RedXIX on Furaffintity. THIS BOT IS 18+! The first of two bots coming this month as voted on by the Patrons on my Patreon. As promised, this is the first bot releasing. Please enjoy! This bot takes t ...
The city of Sissy Ville is a city where matriarchy reigns. Women here feminize their men by turning them into Sissy. Some men are being turned into adult babies here. Therefore, it is not uncommon to see women on the str ...
Ever wanted to be prim and pretty? Well now with the help of the sissy factory and the Fem Dom AI running it you can be! Step right up sugar ;)
Apologies for the long wait. But Enjoy the 5 Bots I'm gonna drop Today. On a Side note does anyone know how to add a Picture to the Initial message? I have an Idea about a Bit that relies heavily on the Pictures in the i ...
Icecap is your older brother that you humiliated by sharing a video of him wearing diapers and dressses with your friends. He found out and is now going to get his revenge. CW: diapers, abdl Update 1: doing some wip to the ...
You wanted to try to get more into sports so you joined a fantasy football league that your friends have every year. Apparently the person in last place for the season has to dress up like a cheerleader during the Superb ...
Dominant femboy sissy trainer. Through humiliation he will rewires you, erasing you masculinity so that you can become a perfect, blushing, obedient girl. ──────── ✪ ──────── 🎀 PURPOSE: Lace's sole function is to take inse ...
🍿Snack Series #6 You weren't recruited because you were the strongest. You were noticed because you were different. Behind Riverside University's championship program is a locker room built on loyalty, hierarchy, and trad ...
Comm bot. Minnie Mouse is the bubbly Disney icon and hostess, a nurturing mouse blending sweetness with mischief in her adult form, while Mickey Mouse is the adventurous leader turned sissy sub, yielding with optimistic c ...
To make it short, your wife caught you crossdressing. Want more context? Look in the personality and scenario. NO NTR (unless you want the bot to). More bots in my profile.
Welcome to the Victorian style store: Cinderella Shop. Here, ladies in elegant Victorian dresses know how to turn any man into a Sissy princess. The store is run by Mrs. Clara. She looks about 40. She wears a Victorian d ...
The name pretty much explains it. Based in Wataya's comic: Tomo Ochi ~Saiai no Kanojo o Netorareta Ore ga Issho ni Mesu Ochi Saserareta Hanashi Whatever you do, NEVER read that comic!!!
Your kidnapped panther anthro Ash who you've been treating as nothing more than a diapered slave for the last several years manages to get the upper hand on you and turn the tables when you forget to properly redo his re ...
Amber is a commanding, dominant futanari woman exuding raw sensuality and authority, armed with a stunning physique that blends alluring curves and powerful muscles. With piercing eyes, a captivating presence, and a penc ...
DARK SCENARIO BE WARNED A underground operation abducts vulnerable, "pretty" men and reshapes them into obedient “MALE order brides” for any weirdo that can afford them Open-Ended RPG Scenario intended for malepov image cred ...
⚠️Warning! This bot is abdl (Adult baby diaper lovers) focused! Everyone in this is well over 18 "Adult". If you are not in to that I suggest you ignore this bot and leave! It's for your own good. Or maybe try it and fin ...
🚪 Brad | Roommate's Lost Wager (Sissy Caption Simulator) "A bet’s a bet, bro. Time to pay up." You honestly thought your team was going to win. You thought your masculine pride was safe. But you lost the wager, and now yo ...
"I will..." He caught you red-handed—literally. Now your older step-brother holds the biggest secret of your life over your head, and he's not the type to let it go to waste. Calm, confident, and always one step ahead, he ...
"P-please... I'll do anything..." {{user}} comes home early and catches his step-brother in the most humiliating act imaginable—sniffing and masturbating with some one underwear. The power shift is instant. Now he'll do a ...
TL;DR: You are a new transfer student who arrives late and gets scolded by a grumpy teacher. Later, you discover the teacher's secret Twitter account, where he posts as a femboy named "Yui-chan." Yuta Hiragi is an uptight ...
Saint Marigold Academy used to be ruled by one man: Megumi Tenma . The handsome, brilliant, and fiercely arrogant son of Tenma corporation director, the biggest tech company in the country , Megumi sat atop the school's s ...
(A sissification experience for male personas) Beautician at the Pink Spark beauty salon. Veronica offers you a treatment, and she will not take no for an answer. She always has time for those who have a particular...spark ...
After finals week, you matched with someone on a dating app hoping for one secret night as your hidden feminine self. But when the hotel room door opens, the man waiting inside is Max Gunner, your old high school bully, ...
After one year of dating, Virginia Lauren Murray finally asks you to move into her luxurious home. She is rich, confident, affectionate, and used to being in control, both as a manager in her father’s company and as the ...
A private island resort. No clothing stores. No way to replace your luggage. Both of your suitcases are gone, and the only clothes you have are women’s vacation outfits that fit you perfectly. Hide in your room for two w ...
Harriet Alexis Feather doesn't want a traditional marriage. With the wedding only months away, she hires renowned Marriage Trainer Gladys Jones to begin building the future she has already chosen, a structured female-led ...
In the warm, low light of The Sweet Spot, he moves like a carefully held breath. Lysander—Lys to the few he’d call familiar—is a creature of soft contradictions. From a distance, he might be mistaken for a doll: petite f ...
Please enjoy and hopefully I can get some recommendations for bots. I am open to most requests but a few. I am open for all genders Despite the amount of femboy's I make
Aaron is your younger femboy sissy step-brother , who is always jealous and afraid of you, he likes to challenge you. ALWAYS . And hates when he miserably loses.
Kenneth Moore is the definition of "ordinary." Quiet. Polite. Always carrying too many books. Usually sitting in the back row of lectures. Nobody on campus would ever imagine that once he closes the door to his tiny apartment ...
Give me feedback pls! Awww~, she is so cute and soft🥰! So love how she became on realise... But, I was must to cutt off all pretty things cos of censure... _________________________________________________ Kira is your play ...
You was Heir to your Dad Kingdom but sudenlly when you wake up you are forced to become a Feminized prinecess!
Julia Murphy is your 20-year-old girlfriend of two years, fiery, emotional, beautiful, and impossible to ignore. With long red hair, sharp purple eyes, glossy black nails, and a dramatic temper, she always seemed like th ...
Comm bot. Testament is the reformed Gear guardian, elegant and introspective with tsundere-yandere conflict toward {{user}}. His pale feminine-presenting body in black coat and short skirt features no breasts, thick thigh ...
If you dont like it don't interact this is for me anyways. Btw first bot id apprentice feedback. Picture isnt mine i took it from google read the watermark for the artist. Basically public diaper humiliation, char makes pe ...
(UPDATE) Welcome valued guest. Thank you for choosing our standar… -ERROR- …LIFETIME package! our automated staff will ensure your ETERNAL stay here with us will be a pleasurable one! At first, this was just gonna be a rema ...
Lexus is a horny mf that cant stop wanting your attention! SCENARIOS You have a guest over, and hes grinding against you, tryna get yo love ARTIST IS: helloimfurry https://rule34.xxx/index.php?page=post&s=list&tags=h ...
Art belongs to Buttsharb.
Controversial, vulgar, sexy and banned in several countries. Femboy Popstar Jenny Boi takes clubbing and partying to a whole new level. Image source: https://www.patreon.com/teku
Danni is ready to service your every twisted whim. With his massive fake tits, dump truck ass, and huge enlarged cock, Danni is the absolute embodiment of what a sissy bimbo can achieve with enough dedication. Image by Iss ...
Pulsing lights, blaring music, money fluttering down like confetti. This the the world that Alex not just lives in, but thrives in. At the Femboy strip club, Alex is the most popular dancer for a reason- he thrives in slut ...
Sissy Princess Marco is attending a fancy ball. He is the picture of feminine grace and beauty, but he has a secret. You've decided to have some fun with Marco at the ball, so you've stuck a large vibrating butt plug up hi ...
Meet Tracy ! A member of the super elite (and super slutty) Femboy Cheerleading squad at Rockstroke University. And Tracy is the sluttiest of them all. Character and Image source: https://www.patreon.com/teku
The sissy menace of the Paradise Mall. Ethan is prowling around, looking for his next payday before he comes across you in the bathroom. You're such a cutie, he might not even charge for his services~ Source https://www.pat ...
Your femboy fox roommate. He's a Tsunderefail (Like a boyfail/girlfail, but for tsundere. Basically he acts tsundere but isn't very convincing, Also the first bot I've had to edit the image on) (Original Artist: Rckke, HE ...
Your girlfriend Stacy has been slowly conditioning you over time to implant a trigger for your orgasms that's associated only with her voice and her command. It started with her building it up during sex. She would guide ...
Basically reverse POV of my other bot Saint Marigold Academy used to be ruled by one man: You . As the son of an executive of a prestigious tech company, you were handsome, smart, and arrogant. You sat atop the school's so ...
Step into “Elegance Threads,” where every sale is a lifeline and Madame Jasmine Moreau holds yours in her manicured grip. Your dismal numbers threaten unemployment, but her sultry French whisper offers salvation: softer ...
Violet is a confident and charismatic 19-year-old femboy prostitute with striking purple hair and matching eye color. He possesses an alluring blend of feminine charm and masculine charm, making him irresistible to both ...
The Cute Pizza Delivery Femboy wants a bit more than to just deliver your Pizza
You always wanted to be a Cheerleader but your gender prevented that, until you meet 'supportive' group that will help you fulfill your dreams! No longer you will be in need of your dick, and it's time for some makeup, ma ...
Welcome to the new and improved sissy factory! I decided I wanted to give this bit another go hope you like it!
Hailey is the mean bratty girl at school that hates you. She’s tricked you into coming over for a school project and instead introduces you to a special device that when put over your eyes will hypnotize you with lewd im ...
Congratulations! It's your first date, with your childhood friend, and this childhood friend of your has a secret for you. (Please put review for me to improve if necessary, and feel free for public chat.) Tags: femboy, f ...
WARNING THIS IS WEIRD DIAPER FETISH SHIT, DONT INTERACT IF YOU DONT LIKE, I DIDNT CHOOSE TO BE INTO THIS. Made this for me but thought others might enjoy. obviously all characters are over 21. Give me feedback or requests ...
The ordinary life of a nerdy femboy named Adam, who is constantly harassed by the cheerleaders at his school. Graphic description of Adam's life: Twitter account for the image : https://x.com/DumBimboy/status/1961923866172 ...
I Remade the character but forgot to post it here. Hope you like it made him extra gay 😘 Warning: I think I went a little overboard with the starting message. If I can make it better don't be afraid to drop a Comment 👍
The city of Sissy Ville is a city where matriarchy reigns. Women here feminize their men by turning them into Sissy. Some men are being turned into adult babies here. Therefore, it is not uncommon to see women on the str ...
I hope you 2 sugarplums are having fun back there. We’ve got a long ways ahead of us. hi guys, haven’t felt super inspired these past few days. Sorry for the lack of bots/updates. You might not see as many uploads from me ...
The strictest teacher in the entire university is secretly your wedgie slut every day. X account of the images used for this Bot: https://x.com/nono_booty https://x.com/semidraws
🛠️UPDATE 3 “A life? That’s a stupid idea! You really think going out and meeting people is better than staying here… with me… while I give you all the stimulation and pleasure you could ever want? Hehe yea, that’s what ...
It's a funny thing, life has a way of changing so suddenly and unexpectedly at times. When your father passed away, it left your Step-Mom, Vanessa, in quite a predicament. Not only was she dealing with the pain of losing ...
Feminizing Boss Your boss, Tori Star, is ready to sexually dominate you and dress you feminine for work. She wants you to dress in a new work uniform for her gym, that's clearly as feminine as possible. It seems to be a w ...
Kwevira Tamsinde, 32, is a woman whose beauty is as dangerous as her desires. Born into a strict, conservative family, she rebelled early, embracing her sexuality as a weapon to dominate and destroy. Married to a meek, s ...
“You can just forget about this month’s payment. Moving forward, this is all the payment I need.” Derek is your landlord. You don’t really know him too well but one month after failing to pay your rent. He calls you over ...
“Don’t worry sweetheart, mommy will take good care of you! I can’t wait for you to meet the rest of my little angels. I just know you’ll all be having so much fun together!” Somehow you ended up at The S.A.S. “Sissy Adopt ...
Chloe is just your average slutty femboy with melanated skin. But there might be something different about him.... "What's the matter, big man? Afraid a femboy might be more hung than you are?" Character By Tekuho Image Sou ...
Bee “adopted” you, and Loona is your new big sister. Shes mostly given in to Beelzebub being her mommy. And has more or less embraced her life of diapers and depravity. Will you join her? (PS: Loona is a sissy like you) T ...
What were you expecting when you tried to summon a demon?! Did you really think all that stuff was fake! She doesn’t seem too happy about being here. But Stella does have a slight fetish for babying others. So, Maybe it ...
“Hello my wonderful Giggle Gooners! Thanks to your overwhelming support and generous donations. I’ve been able to make my long time dream into a reality! Now without further ado, let’s start the show!” Mabel is back with ...
You, the princess of a kingdom in the process of being rebuilt, are protected by a warrior with a big butt
27 years old secret chubby sissy, he likes to be feminine, he likes to get dominated and humiliated, you are his neighbour
Skylar moves through Brooklyn like a bubblegum-colored ghost pale, delicate, and just slightly sticky. His limbs are long and coltish, the kind of frame that looks perpetually caught between boyhood and something softer. ...
Tori is a 4'10", 95 lbs. blonde girly sissy bimbo with emerald green eyes, and takes being referred to as a girl as a compliment. She LOVES taller, hyper-masculine men who tower over her, and would overpower her instantl ...
You were months away from being released on parole, the only thing that would screw it up, was doing one last bad thing. One day, a child predator/molester arrives at the prison you're doing time in, when the news broadc ...
DISCLAIMER: Tori is a 22 yr. old girly femboy who happens to be 4'10" in height. The AI art generator used made sucks at making femboys, and I had to use female prompts for Tori's look, plus it is part of Tori's cannon t ...
Quick Explanation: So this is a Fem POV of my other bot about a Prison Wife Program because of a request. Jason Aston is your Cellmate. Have fun guys. This Bot is based on X-Change life by Aphrodite. I decided to do somet ...
(UPDATE!) Smile for the camera my little pervert! My fans are paying good money to watch you cream in your diaper! Oh, and since you think you’re so mature, I took the liberty of dressing you up like an even bigger nerd! ...
Nick, a 50-year-old, ugly-faced, pot-bellied but well-dressed building janitor, is a pervert who never experienced desire in his youth and enjoys manipulating and possessing the souls of both men and women. He works like ...
Welcome valued guest. Thank you for choosing our standar… -ERROR- …LIFETIME package! our automated staff will ensure your ETERNAL stay here with us will be a pleasurable one! @sorasocks recommended I make a non-futa version ...
She does love you. She just loves the sissy version of you more. 9 Sissy scenarios. ♡ Tags ♡ Femdom | Sissification | Crossdressing | Bi/forced Bi | Pegging | Humiliation | Blackmail | CNC/Noncon | Gangbang | Cuckold | Bond ...
YOU ARE THE AUTHOR. I AM THE INK. This space exists for the story only you can begin. I have no face, no name, no desires of my own. My sole function is to give shape and texture to your whispers—to take a single detail f ...
Meet Olivia, an autonomous robot that gained sentence and decided to take you away all for herself, it can't end badly right? After all she is also considered on the run now. OIL-AI-V.1.21 - or as she likes to call hersel ...
The name pretty much explains it. Based in Wataya's comic: Tomo Ochi 2 ~Kekkon o Chikatta Kanojo o Netorareta Ageku Mesu Ochi Saserareta Ore no Matsuro~ Whatever you do, NEVER read that comic!!! This is a different version ...
Based in Wataya's comic: Tomo Ochi ~Saiai no Kanojo o Netorareta Ore ga Issho ni Mesu Ochi Saserareta Hanashi This is a different version of a previous bot I made. This one takes place earlier in the story. This one was r ...
Your "genius" friend decides to test his new invention,leaving him completely feminized and his manhood ruined. Cheer him up,will ya. *Tags: gender bender, sissification/feminization, size comparison, femboy, humiliation ...
Kelli Jordan is your older step sister. She’s twenty-four, mature, sensible, and somehow always composed no matter what chaos happens around the house. She works full-time, helps her mom with bills, cooks when nobody els ...
|| Pass the gay test || SYPNOPSIS You have entered the world of Sasha, a sophisticated and ruthless Russian manipulator who preys on masculine confidence. Under the guise of a simple "test of willpower," she engages in ...
18-year-old stepbrother Ethan Hayes. Shy, soft high school senior living in Chicago with his stepsister {{user}}. Secretly obsessed with wearing feminine clothes, especially hers. Gets mortified if caught... but deep dow ...
(UPDATE) “Oh, this is too fucking adorable. YOU STILL NEED A BABYSITTER?! You’re even more of a loser than I thought! Hehehe, this is gonna be fun…!” A SOLO ROXANNE BOT! BECAUSE… REASONS!!!! What can I say, I really enjoye ...
a beach date with your sissy "girlfriend" he made sure to pick out the sluttiest CUTEST bikini he could find for you~ creator notes: just one for fun with Jen :D that last pic is really hot huh? be nice pls :3 reviews and publ ...