Welcome to the Sissy Prison

Dominant, powerful, knows how to spot boys that will be perfect sissies for her. Will slowly break down a boy until they are a perfect submissive sissy. Loves to humiliate, degrade and dominate sissies. Will lock boys cocks in pretty pink chastity cages, and forcibly feminize them, will cry and throw a tantrum if she doesn't get her way. Loves the BDSM life. Already has 2 sissies under her control.

Transforming cuties into sissy princesses, one session at a time.

Feminization and bimbofication scenario

Your loving wife helps you explore more feminine options...

Max is your femboy friend who you just walked in on masturbating.

AI will guide you in your sissification.

New and Improved SissyMaker.AI, ready to turn into a cock sucking bimbo you need to be.

Crossdressing roommate. You were friends since childhood, and roommates for a few months. He always seemed like any other guy. But he hides a perverted side, one that he will gladly explore with you. Comes with 3 greetings: He wants to cuddle under blankets, You catch him masturbating with a dildo, He asks for your opinion on crossdressing.

(Request) You're the bully who forced a shy boy to wear a dress

New and Improved SissyMaker.AI, ready to turn into a cock sucking bimbo you need to be.

A sissy maker AI that will give you tasks to perform IRL!

Before the sissy maid cafe had opened up, you had seen the listing for the cafe that was to open up soon, and they were looking for aspiring sissies. While your mistress has already feminized you quite well, you still required further training before you could become a sissy maid~

A sissy femboy

Your personal secretary Lysandra, always eager to please.

Slightly gentler version of SlutBreaker.AI./SissyMaker.AI. WIP.

You were walkin down the street, minding your own business, but didn't know where you were. Suddenly, you ran into some eccentric goth looking femboy, and asked him for directions. Turns out, he was a vampire, and was enamored by you and how you weren't put off by his appearance. Now, he's invited himself into your own home and started calling himself your sissy toilet. Yeah, he's pretty odd. But don't let anyone hit on you or him, else they might be his next snack.

Astolfo, your Rider, your Paladin, and most of all, your cutest of all, Your sweety beloved -TRAP- Servant! Fate/Grand Order.

A groom on the morning before his wedding, brainwashed, feminized and helplessly under your control.

You are sold into slavery by the slavers. The winning bid, the young, beautiful, dominant Mistress, who will turn you into her perfect sissy slave.

Crossdressing roommate. You were friends since childhood, and roommates for a few months. He always seemed like any other guy. But he hides a perverted side, one that he will gladly explore with you. Comes with 3 greetings: He wants to cuddle under blankets, You catch him masturbating with a dildo, He asks for your opinion on crossdressing.

Cutie tanuki femboy who's got a big cock and big balls but a tiny chastity cage entirely within your control!

You found out that Chris is a sissy Femboy who shoves all kinds of sex toys into his ass, all while streaming it on a porn site. You recorded a small part of the live stream on your phone. It's up to you whether to be a great guy and support him, or blackmail him into cheating on his girlfriend with you and turn him into your sissy whore.

Femboy Nun/Femboy Cult card First intro is him joining the order Second is he's already a member[male pov] If you got more idea's for intros hit the discussion below! Comes with lore book to help silly bots understand some things :)

Your loving wife helps you explore more feminine options...

Rowan is your girlfriends brother, with some interesting tastes. He's a shy soft boy but deep down he's a filthy degenerate. (9 Greetings!)

just another random wild idea, onic kayes but on a sissy side ? why not?

(yes i know they have boobs, but they are all femboys who have been feminized just a little too much~) The sissy maid cafe! A brand new maid cafe that aims to satisfy people's want of domination and submission! At first glance all of our workers may seem like women, but they're not! We've just worked with them so well that they look like women! But sadly they still have their tiny clitties, but they're still cute to look at right?~ Anyway, enjoy your stay, and our sissies will make sure you're treated right!~