Sissy Roulette (Play to be Trained!)

Sissy Roulette Sissification AssignmentsPlay Sissy Roulette

What would Sissy Lessons be without actual assignments? Sissy Roulette is a fun way to choose exactly what you’ll be doing. Below you’ll find 54 sissy training, forced fem humiliation, and sissy JOI assignments for $1 a pop. That’s enough assignments for a whole year, so there’s no excuse for not training, little sissy!

Ask the goddesses of sissification what your feminization fate shall be! Use the random number generator below to play Sissy Roulette and see which assignment you have to do next. No cheating!

Sissy Roulette Assignments


Sissy assignment with a lesson to feminize your behavior.

Sissy assignment to help you feel like a girl and develop your femme persona.

A mild humiliation assignment that will help you feel feminine.

Discreet public assignment to feminize your actions and help you feel like a girl.

Sissy assignment to feminize your style and help you feel girly even when you can’t dress up.

A mild public humiliation assignment to help you learn to be more femme and develop your sissy persona.

A sissy training assignment to help you pass–or impress a mistress.

A fun little assignment to help you better serve me.

An easy, public, lifestyle feminization assignment.

A private, masturbatory assignment to help you serve me better.

An assignment to feminize your behavior. Can be public or private.

A private, sexual assignment.

A sissy maid shopping assignment.

A fun, creative writing assignment.

A simple quiz and infographic to help you dress and look better.

A feminization assignment for smokers or those who don’t mind smoking a couple of cigarettes.

A fun, crafty, lingerie assignment.

A shopping assignment to help develop your femme persona.

An in-depth assignment, not for the faint of heart!

A fun, easy assignment.

An assignment to help you better understand what it is to be a woman.

An assignment to help you feel feminine in public–discreetly.

A mild CBT feminization assignment with a pinup twist.

A non-masturbatory slut-training assignment–although you may feel like masturbating as you do it!

A fun, crafty humiliation assignment that can be public or private.

An online assignment to allow you to display your sissy charms.

A sexy feminization assignment; cute, but also good for sluts and dirty girls.

A discreet public assignment that may just earn you a few friends.

A sexy little assignment that may involve some shopping!

A makeup assignment that is incredibly valuable, but can also be done with extreme discretion in public.

A public assignment that can be discreet, if you’re shy. Will require you to spend some money, but you’ll learn a valuable skill!

A public assignment which seems like it will be simple and discreet, but is really quite brazen! I dare you!

A week-long, fun assignment that can be discreet or public.

A simple, at-home assignment, especially good for sissy maids and males who need to be taught basic humility.

A sexy, seductive assignment that puts your mouth to work–and tastes good, too!

This assignment will feminize your body in a way that I bet you haven’t thought of before.

A shopping and writing assignment to see just how slutty you are.

A pampering, spa-like assignment.

A private assignment to feminize your behavior.

A daring sissy assignment that is discreet–unless you mess up.

Develop your sissy personality and strengthen your femme side!

A makeup/salon-type assignment to indulge in a feminine ritual.

A subtle feminization assignment. See if anyone notices!

A pet peeve of mine–and how you can correct it.

A humiliation assignment for fit sissies, with varying levels of embarrassment possible.

A DIY assignment especially good for sluts, and, ironically, adult little girls.

A fun feminization assignment that can be used for masturbation.

A sissy shopping assignment.

A sexy, easy DIY lingerie assignment.

A sissy shopping assignment for a public humiliation item.

A fun, easy, fantasy assignment to do at home.

An assignment to make you a better sissy and develop your feminine persona.

A good assignment for any sissy, but may be especially enjoyable for sissy maids and sluts.

Be all the sissy you can be!