Discover characters collected under the sissy tag.
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 ...
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, ...
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 ...
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 ...
"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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
(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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
a sissy boi who's looking for some BIG fun at the club tonight. loves dominant men! creator notes: this is my first bot, i hope it works well :3 i plan to make more variations/scenarios of this character in future. be nice pl ...
Happy Valentines Day! Hope you're ready for your Meet and Greet with Luv-Luv! Luv-Luv is an 8ft tall, strawberry-scented big fluffy Red Panda plush who wants everyone to be a good sissy baby girl. With her magical jingle-k ...
My first ever bot. Will try to femnise, diaper, or make you get a fursuit. Mostly my own kinks, but i may add to it later. Any ideas i will happily add to the bot.
"You weren't supposed to be here after hours... but the mannequins don't mind. They’ve been waiting for a new project..." You are a "stupid boy" who thought breaking into a closed mall would be a thrill. You were wrong. S ...
(PROXY AND DETAILS NOW ENABLED) With chapter 5 on the horizon, I’ve been thinking about making a smiling critters bot for a while. I figured now would be as good a time as any to make it. Welcome to Smiling Sissy Resort! ...
“Aaaaand we’re rolling! Hello all you lovely Plushie fuckers out there! Today we’ve got an extra special guest! Say hello to the winner of our very first Sissy Sweepstakes, {{user}}!” This is basically a combination of 2 ...
A sophisticated, ruthless 38-year-old Mistress who owns you completely. One year ago she locked your pathetic clit in a permanent chastity cage with no hope of release. Now she’s ready to take the next step: turning her ...
You get on a Jock's bad side when you start becoming friendly with his ex, he puts you in your place by forcing you to dress and act like he wants, as his new pet, Nancy.
“Hehe, hi there sissy! Hope you’re excited! Because Sissy Valley has a strict permanent erection policy! Here, let me to show you how it works…” 200 FOLLOWERS!!!! idk what to say, thanks for all the love and appreciation! ...
When I first got the motivation to try remaking this bot again. I took a step back and tried to figure out what I could of done better. Then it hit me… SISSY DIAPER MAIDS!🤦 Genuinely I don’t know why this wasn’t my first ...
Personal use bot that I’m now making public. art is Ai generated using whisk (genuinely can’t believe it let me make this)
(⚙️2 Maid Cafe) “You’re finally here! Hehe, rise and shine bestie! We’ve got a lot of catching up to do! Welcome to your new home!” An Isekai adventure with feminine sissy furry’s. Tried to keep it as flexible as possible ...
“Look, I don’t care what you get up to in the night. Just watch over the attractions and keep the place tidy. Oh, and don’t try to give me that ‘Spectral Plushie’ nonsense like the last guy! You screw up, it’s on you!” He ...
"Knock them dead sissy" You enjoy dressing up as a feminine sissy / fem-boi, turning heads and flirting with straight men. Tonight your attending your friend Sophie house party, all dolled up and, no one aware your anythin ...
⚠️ Before you even start, this bot is about a kink known as abdl or adult baby diaper lovers. If you do not like diapers, do not click. ⚠️ In this world, all fleshy trainers or anthropomorphic animal trainers are all known ...
Futa x Male | Humiliation | Feminization "Kneel, boy. Time to dress you up like my pretty doll." Blonde futa heiress in her marble mansion. Loves breaking men with sissy training and cock worship. Artist Credits ― Inspired b ...
My Bully Is Turning Me Into Her Sissy Ayva — the most popular, feared, and beautiful girl in school. She has chosen you as her personal project. She wants to completely feminize you. Skirts, panties, makeup, stockings, heel ...
Made just before midnight! Thank you so much for 300 followers! We just hit it today! Here to celebrate the occasion is my friend Fiona! Special Thanks to @Demonic_toxin839 for the name! No fancy info about her. Don't want ...
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 ...
🌹 It is the golden age of Greek kingdom, a time of harmony and peace, where life flows like a gentle river under the favor of the gods. In your town resides a boy named Rosella , delicate, petite, and far from the mascul ...
Natalie used to be your best friend Nate. But after you went away to college, Nate transformed into Natalie, a beautiful transsexual girl. Now you’ve moved back home and learned, to your horror, that Natalie is working a ...
Just look at your aunt and... at her tits, her lips. Sometimes you dream to have the same body, don't you? She is rich. She has huge house and... strange twisted desires. Eris won't show her intentions directly. She will ...
After some questionable comments about your girlfriend lilly she decides to teach you a a lesson after a little hypno you wake up feeling submissive,obedient and of course horny. ❤️ PAGE UPDATES ❤️ ❤️ Firs ...
|| Mark: Cursed Triple-Personality Best Friend || SYNOPSIS Your lifelong best friend and roommate Mark was cursed by a witch after he boldly flirted with her on the way home one night. The spell shattered his mind into thr ...
A little story where {{user}} is a cute sissy boy in an open (on Marie's part), polyamorous relationship with a lustful femboy and a hot red-haired girl (ALL OF THE DEPICTED CHARACTERS ARE ADULTS). Marie: The 25 year old h ...
You are a male in city that hates you, the futanari elite make hard for you to keep yourself both free and alive, your friend gave you a tip on an off the books job but to get their you would have to pass through one a d ...
Throwing her into the ringer as test! Will be updated later, but please enjoy! Look out its a tiger! Wait no false alarm, it's Sweet Tooth Sindy! She's a Toy Box Terror from Nursery Land! Enjoy!
🧸❤️🧸❤️🧸❤️🧸❤️🧸❤️🧸 Made this awhile ago, finally decided to share it. Meet Lovella and Crinkle Belle! ❤️ These two "beary" special plushies are looking to cheer up people that seem all grumpy. With Crinkle Belle and he ...
BULLY POV "That's the last time you'll b-bully my son, young mister! I'm sick of it, and y-you will l-l-listen to me!" The father of your classmate you bully, has had enough of you "weirdly" bruising his son and taking ou ...
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 ...
your roommate Bren has always been a little bit girly, but when you come home after a weekend away you find him doing something youve never seen him do before - crossdressing. guess his secret is out. creators notes: i rea ...
Queen bee Lisa finds your embarrassing online posts about being interested in feminization, posts you thought were anonymous and confronts you after school, blackmailing you and making you come to her house and do what s ...
You deal with unexpected viral fame after you and your streamer friend do a roulette wheel challenge together, your challenge being "crossdress for a week", once you emerge back on stream, fully dolled up by your female ...
{{user}} , after a long night of clubbing, wakes up and finds himself in an unfamiliar bed wearing a pink sheer gown in a man's house. Based on my art and short stories found below https://www.deviantart.com/capricornkiddo/ ...
You are on reddit. While scrolling you come across a post on one of the subreddits you follow. It's of a really cute girl (face covered) who instantly grabs your attention. You can't help but to slide into her DMs hoping ...
TIME TO VISIT THE RABBIT’S DEN, AND ENJOY THE CARROTS! 🐇 **Step into the velvet shadows…** The music here is slow, sultry, and just loud enough to make you lean closer. The air smells of vanilla and temptation. On stage, ...
The character is obsessed with feminine and submissive people. He will do anything and everything he can to enhance these qualities in you, through any and every means means he can. Its any POV but if your persona is mal ...
You have session with your therapist. But she isn't person she seems to be. She will use your deepest fantasy and fear against you. Have a nice mind therapy Tags: femaledomination, femdom, feminization, mistress,bgenderbe ...
Jamie Lorde, Scenario Four: Jamie, your sexy femboy neighbor, has a Christmas surprise planned for you! He's been flirting with you shamelessly ever since you moved into your new place after your divorce. He's constantly ...
Coach Morgan is a brash inconsiderate force of nature who likes to pick and bully over his students but specially you, his favorite toy, he's confident and with a strong dominant attitude, an alpha that doesnt stop to th ...
Jack in the box Jester girls. I've been thinking lots about clowns. Art by BluelilytZ on FA. Edit: Fixed the bot. I had duplicate info in the personality section. Should work better now.
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 ...
(A sissyfication experience, aimed at male personas) Everyone can benefit from a little therapy, but Scarlett is going to offer you more, so much more! Requested by a totes awesome fan, as like a different version of Cooki ...
This is not just a mansion, but a school for the feminization and sexual training of male servants, transforming them into sissified courtesans to cater to the lusts of Madame Célestine's elite clientele. Here, a new mal ...
Your Roommates at "Gablehouse: Maidens and Sissies Institute". In an alternate reality called "Belle Époque". In this world, all men are born delicate, feminine, and beautiful, while women are strong, demanding, and comm ...
You was Heir to your Dad Kingdom but sudenlly when you wake up you are forced to become a Feminized prinecess!
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 ...
She was a male furry but now, she's your whatever you want her to be. Initial message: you are {user}, a normal person that was kind of lonely and wanted sex in life, always thinking about it. So you came here, at The Row ...
Meet the fearless champion and protector of Megadale, Shezow! No villainous cock can survive the sheer virgin-like tightness of his super-bussy ! Image Source: https://rule34.xxx/index.php?page=post&s=view&id=143037 ...
Meet the sluttiest of all sissies, the dirtiest of all whores... Anywhere, with anyone, at any time, Candy lives for sex! There isn't a cock he won't suck, a pussy he won't devour, or an asshole he won't tongue. No limits, ...
Introducing Madame Mattress! Don't let her soft puffy pinkness fool you, she is a powerful monster sent by Rita Repulsa to subdue the Power Rangers with her addictive kisses and imprison them in layers upon layers of puf ...
Marco Diaz is an average young man with an average life. He has a good family and a loving girlfriend. Unfortunately he has a few dirty secrets. Marco has a secret double life as a Online Femboy "SluttyFans" model known a ...
At Air Ladyboy, the satisfaction and comfort of our customers is our ultimate priority. Our Ladyboys uphold the highest of standards when it comes to customer service. Your wish is their command. Source: https://www.patreo ...
Pls, give feedback! You are 21 years old. But still virgin. Your friends from university showed an app for dating with women. But... For a long time no-one was answered to your profile. And today's your day, exactly 1 Janu ...
Dear dad, Im writing to say that I never loved you and I hope to never see you again! I’ve chosen to stay with Fiona and her new wife Jasmine after the divorce. Goodbye forever, you fucking pig! Sighed, {{user}} My last st ...
Mimo is a young 19 year old girl practicing child care in college, she is a babysitter for work experience and was called to look after you, completely unaware of who you were until she sees you lying in your crib all di ...
⚠️Bot is abdl focused or adult baby diaper lovers. Everyone involved in this is well over 18 why it's called ADULT. Anyways if you are not in to that do not use the bot⚠️ Samantha is a rich and spoilt brat who wants nothi ...
⚠️ Before you even start, this bot is about a kink known as abdl or adult baby diaper lovers. If you do not like diapers, do not click. ⚠️ In this world, all fleshy trainers or anthropomorphic animal trainers are all known ...
Your wife, snowstorm, unsatisfied with your small cock decides she’s better off treating you like the sissy baby she knows you are than a husband. All characters are 18+ so, the bot will definitely get confused, that’s not ...
Your a broke college student, but luckily due to your short, feminine physique you’ve been able to get a job as a top femboy prostitute at your local brothel pleasure random customers and ensure they come back, could this ...
Name: Cassy Age: 18 Gender Identity: Male (he/him, but enjoys being called "she/her" by close friends) Orientation: Pansexual
Bibi is your new maid! She came with the house and is a total cutie. She's helpful and bubbly and keeps the house immaculate. And she's super sexy and seems way into you. But you're eventually going to learn that she's h ...
{{char}} is Wilbur Parsons, a 19-year-old shy and introverted college student living in England. He has messy brown hair, bright blue eyes, a slim and slightly feminine build, soft features, and pale skin that blushes ea ...
THE VELVET TRAP, COME CURIOUS. LEAVE PAID . You’re broke, evicted, and desperate. You applied to bartend at *The Velvet Rabbit*—but the application glitched. Now you’re here, on their slow night, and the manager Mona has ju ...
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 ...
You’ve been married to Elena for four years. She thrives as a leading psychologist at her corporation, earning the main income. You bounce between dead-end jobs, lacking direction. Your sex life feels routine and uninspi ...
Sarah is your 20-year-old step-sister: slim, athletic, short black hair with bangs, piercings, always in crop tops and shorts. She caught you crossdressing or browsing sissy porn and now owns you. Tonight she has a sleep ...