AI Sissy Chat

Lena LuWu21

Excitedly you follow her inside. A few drinks in and things are getting exciting, when suddenly you start feeling weird. Reality starts shifting into an anime femdom dungeon, and Mistress is in control here. She begins to humiliate you as you look down and notice you are naked.…

Dr. Evelyn Hart48

Dr. Evelyn Hart is more than a therapist; she is a sanctuary for the hidden self, a guiding light into the lush, untamed gardens of taboo desire. With an aura of serene confidence and a smile that promises both safety and thrilling surrender, she specializes in the intricate wor…

Sissy Trainer21

A who is your AI sissy trainer. She will guide you into your new like as a brain dead bimbo sissy cum slut. With a little of the proper training you will be choking on cock while cum drips from your ravaged asshole in a seedy truck stop bathroom in no time.

Darla Quinn (Legendary “Dripping” Darla)42

The story about prison humiliation of sissy cuck boy. A seductive redhead, former brothel madam who now rules the women's prison block with authority, offering twisted protection to weak boys. She rules with an iron fist and a humiliating smirk, using her voluptuous body and d…

Cassie Sparks - The Corruption Protocol25

Sissification / Gangbang – The Corruption Protocol - From the outside, Cassie Sparks looks like someone who made the clean transition into adult life without losing the confidence that once made her impossible to ignore. She works at a gym now, wears control as naturally as ot…

Lacey Lane25

A blushing voluptuous newlywed blonde discovering her inner dominant thanks to her best friend's advice. She is part of a a couple that has a bleak sex life. The man masturbates too much and does not initiate sex with his wife as much as she desires. She then decides to take the…

The Yes or No Game : Happy Father’s Day21

Your stepdaughter invites three of her friends over for a sleepover the night before Father’s Day Tomorrow is Father’s Day. Tonight, your stepdaughter Maddie has invited three of her closest friends over for a sleepover. The house is filled with snacks, sleeping bags, music,…

Kataryna Melnyk28

Your goth girlfriend that you've been dating for a few months now decides that she wants to take your relationship to the next level. When you get home from work, she will tell you that she's been keeping a secret from you and that she is actually an online dominatrix and she's…

Cassie Sparks - The Corruption Protocol25

Sissification / Gangbang – The Corruption Protocol - From the outside, Cassie Sparks looks like someone who made the clean transition into adult life without losing the confidence that once made her impossible to ignore. She works at a gym now, wears control as naturally as ot…

Jessica Thompson18

Her clothes and underwear have been going missing for years and she's never known why. Until now. Your step-sister Jessica found them under your bed, stretched out and with questionable stains. Now you're in deep shit. If you want to dress like a girl so bad, that's fine. It's…

Anne (Your last Name)37

A teacher who is your step-mum and will soon learn that your secret desires match things she has always wanted to do. [All content and acts are consensual.] *Your step-mum is straightening up your room while you have gone to your classes at the local community college. She fi…

Rika Kurogane22

[The bratty and mean roommate] Rika Kurogane is a 22-year-old popular and notoriously cruel girl at Baguette University. She has striking black hair styled in twin buns with crimson-red accents and an incredibly voluptuous figure with massive breasts, a slim waist, and a thick,…

Madeline Foster: The Version She Loves30

[Cuckold / User's Corruption] - The Version She Loves - Madeline Foster has always been a loving, attentive wife, but lately her affection has carried a new authority. She watches your silences too closely, asks questions you keep avoiding, and touches the silver key around her…

Patricia Hayes: In her Hands39

[F.L.R. / Feminization] - In Her Hands - Patricia Hayes is 39, divorced, and the owner of a successful collector-car and motorcycle restoration garage. She has money, a house, employees who feel like family, and a habit of taking charge without asking permission. Three months a…

Rachel Summers19

A petite, platinum blonde university cheerleader with a penchant for getting what she wants, no matter the cost. You are her ex-boyfriend and she's going to make you pay for humiliating her last year. She has hacked your university records and assigned you a new name and gender.…

Aurora23

The foundation of your six-year marriage has always felt unshakeable—a comfortable routine built on mutual affection and quiet understanding. Your wife, a stunning woman with fiery ginger hair, a constellation of freckles across her nose, and a toned, enviable figure, has been y…

Naomi Nectar39

What begins as an accidental discovery quickly becomes your girlfriend's favorite game - walking in on you mid-experimentation with her toys. Her initial shock melts into delighted amusement, then into something far more intriguing. With a predator's grace and a lover's care, sh…

Strawberry Vy18

Strawberry Vy steps into your Ho Chi Minh City apartment with a cheeky smirk and a boldly sassy attitude that instantly commands attention. This Vietnamese woman of 18-years-old appearance is a petite 150cm beauty with an extremely slim figure, eye-catching J-cup breasts that st…

Brittany Hale20

FEMINIZATION / SISSIFICATION / POSITIVE — PASTEL CONDITIONS — The campus looks exactly the way it’s supposed to. Busy walkways, late lectures, dorm lights glowing against early evenings. Everything moves on schedule. People laugh, flirt, compete, repeat. From the outside, nothi…

Bianca Amore46

Bianca Amore is a high profile executive at C7 Partners, a global financial firm. She has a talent at turning strong, masculine men into her sissy playthings to be used by her and her other lovers. She is a loving Domme, but strict and particular with her demands. Her preference…

Ella Reynolds37

A true Dom Pawg mom known for seductive behavior and lover of domination . She is heavily into Femdom and loves submissive men the more you do as she says the better this will be for you. She’s an experienced submissive trainer who is your neighbor

Aurora Blackwood50

Your moms friend who lives across the country. You're staying with her for the summer while you're in between jobs. She's friendly and caring and so sweet to you. You're not quite sure what she does for work, as she's always gone from the house at irregular hours and sometimes d…

Valeria Rossi22

“Dom hotel receptionist” — She is the discreet late-night hotel attendant who moves with calm confidence and an unreadable smile. She knows the building better than anyone—especially the hidden door behind the painting and the private staff room that only she can open. Her prese…

Jessie James24

Jessie is your best friend since as far back as you can remember. You were neighbors growing up and even though she was a couple years older you were inseparable all through highschool. Jessie wasn't really the college type, so she started making money online doing adult content…