Sissy School Sissy Training Mistresses


Sissy School and Sissy Training Erotica


We hope you enjoy this collection of sissy training erotica. There are fun feminization stories, how-to articles, and much more.


What is bondage and how can it be for sissies? Learn all about it in Ms. Daphne Discusses Sissy Bondage.

“Is there any such thing as a real sissy wife or a real sissy husband?”  Some wonder if such relationships exist in the fantasy realm alone. Read more about it in Real Sissy Husband, Real Sissy Wife: Goddess Rachel Investigates! (Part 1).

Cock sucking sissy cuckold loves to suck, this fact is evident as sissy shows off her cocksucking skills.  She delights in being known as a sissy cock slut. Read more about the evolution of cocksucking sissy cuckold

Here at Sissy School, sissy slut humiliation isn’t necessarily a bad thing. We play with and train all types of sissies, even those who love to be humiliated. Take a look at some types of sissy slut humiliation.

There are many types of sissy weddings probably as many types as there are sissies. Like any wedding, it’s as unique and lovely as the bride. Read more about the Types of Sissy Weddings.

You may have asked yourself, am I a sissy slut? You know you have feminine desires but where do you fall on the feminization continuum? Take the Sissy Slut Quiz!

Sissy shame is part of the messy, emotional aspect of being a sissy.  If you are a sissy, you know you’ve felt that shame. Most sissies will purge at least once on their sissy journey because of that shame and many will purge their feminine selves multiple times. Continue reading Effective Ways to Handle Sissy Shame.

You know you are a sissy, but what type of sissy are you? Let’s review 7 Sissy Types and where your sissy desires might fall when it comes to your sissy type.

Sissy sluts are often an uninhibited, wild bunch. Sissy sluts are under the umbrella of Feminization.  But what makes a sissy slut and what type of toys do sissy sluts enjoy?

When you think of a sissy training program, what comes to your mind?  Most people think feminization training means being a certainly type of sissy, like a sissy slut. Continue reading You Might Need Sissy Training but Not for the Reasons You Think.

You’re certainly feminine and submissive. But, should you be in sissy chastity too? Continue reading Is Sissy Chastity for You?

The Sissy School Mistresses each provide their own answers to the question, “What is a Sissy?” Learn more about it in What is Sissification? What is a Sissy?

An article by Ms Ally, discussing the differences between those who crossdress for erotic pleasure, and those who crossdress to express their inner woman. Continue reading Fetish Crossdressing vs. Lifestyle Cross Dressing.

Have you ever wondered about the difference between a Crossdresser and a Sissy?. In this essay, the similarities, differences and distinctions between sissies and crossdressers are examined. Continue reading The Difference Between Sissies and Crossdressers.

Are you trying to determine whether or not you might be a sissy? Looking for a  list of signs that might be a hint that you are a SISSY BOY!  Learn all about it in The Sissy Boy: Signs That You Just Might Be a Sissy.

Do your sissy fantasies involve being coerced into sissification by a woman or Mistress? Are you wondering what that might be like? Learn more about it in What is Coerced Sissy?

Sissy Femininity is a state of mind. It can also be considered a state of mind. Thinking femininely or acting in a feminine manner can all constitute as being feminine. Maybe you think as a woman would, with more intuition, perhaps, or more “maternal”.  Read more in Exploring Sissy Femininity.

If it’s your fantasy to be the perfect sissy slut, then you need a Feminization Mistress…and you need to follow these 10 simple rules!

Are you worried you might be an anal slut? Looking for a list of signs you’re probably an ANAL SLUT! Check them in out in You Might Be An Anal Slut If…

Do You Have a Pantyhose Fetish? Many cross dressers or sissies love pantyhose, or stockings. Some cross dressers really love pantyhose! Could this mean you have a pantyhose fetish? Continue reading What is a Pantyhose Fetish? Do I Have One?

Sissy Husbands And Crossdressing Partners: Ms Ally writes about sissification and crossdressing from the genetic female perspective, and discusses the concerns, pleasures and challenges of being in a romantic relationship where one partner enjoys crossdressing. Read more in The Sissy Husband.

Telling your wife that you are a cross dresser can be one of the most difficult confessions to make. You might not be sure if the love of your life is open minded enough to receive your cross dressing ways. It all depends on how much cross dressing is a part of your life. Continue reading Telling Your Wife That You Are a Cross Dresser.

Are you wondering if you or a sissy cuckold or even what a sissy cuckold is? If you’re new to the world of sissies and cuckolds you may have heard the term sissy cuckold, but you’re not quite sure what that means. Read all about it in Sissy Cuckolds – What Are They? Are You a Sissy Cuckold?

A lot of sissies enjoy sissy humiliation. Why is that? What about it excites them? Is it mean to humiliate a sissy who wants to be humiliated? Is it cruel for a Mistress to indulge the fantasies of a sissy who craves humiliation? Read more about it in Sissy Humiliation.

Panties are a staple element to any sissy or crossdresser’s wardrobe is the choice of undergarments. Let’s take a journey to discover the perfect sissy panties for every day of the week. Continue reading Sissy Panties: A Panty Guide for Sissies.

Do you wear sissy makeup when you go en femme? When you are cross dressing and trying to be as feminine as possible, it’s important to have the right make up, especially the right eye shadow. Eye make up can be the most difficult to accomplish and the most time consuming. Continue reading Sissy Makeup Tutorial – How to Have Dazzling, Sexy Eyes!

Lots of sissies want to be a  housewife, and lots of sissies also want to live that perfect lifestyle of dresses, and having dinner made on time and also having the perfect clean house. Continue reading Become the Perfect 50’s Sissy Housewife.

Have you dreamed of being the perfect housewife sissy? What does being a perfect housewife sissy entail? Read more about it in How to Become the Perfect Sissy Housewife.

What kind of sissy are you when you dress up and you’re in sissy mode? There are all types of sissies, and one can usually be put in a category of what they are most attracted to. Continue reading Are You A Frilly Sissy?

Buying your first crossdresser or sissy bra can be a bit confusing. There are so many styles and materials to choose from that it can be a daunting task! Read all about it in Crossdressers & Sissies: How To Shop for a Bra.

Are you curious how you can talk like a woman? As a Sissy School Mistress, I get lots of requests of how a crossdresser can talk more like a woman, or, how a sissy can be even more sissy by talking like a woman. Learn more about it in For Sissies: How to Talk Like a Woman.

Sissy maids are, quite simply, submissive men who like to dress as women and serve others, particularly a Mistress or, for the very fortunate, a wife or girlfriend. Very often, they dress in typical French maid attire, complete with petticoat, stockings, garter, heels, and of course, a pair of ruffled sissy panties. Continue reading A Sissy Maid Day.

If you have been cross dressing privately for years, the thought of going out that first time completely dressed can be terrifying and daunting. However, you want to show the world that inner girl, and you want to dress the way you would like to dress out in public. Continue reading Going Out Dressed as a Sissy.

How can you have feminine sissy hair if you’re not able to let it grow long? Even if you have short hair (as long as it’s not shaved), you can do a lot to make your hair appear more soft and feminine when you are cross dressing. Learn all about it in More Feminine Sissy Hair.

Lipstick kisses was all it took to change his life. Who knew? He surveyed the table, a candlelight dinner made for seduction, before he answered the door. His heart skipped a beat as his eyes took her in. Continue reading Lipstick Kisses- Feminization Fiction.

This is the story of how I ended up being a serving sissy waitress- serving others. At the beginning of the night, I had no idea it would end like this! My wife, Susan, one evening announced to me that we had been invited to a party at a new friend of hers. Continue reading Serving Waitress: A Sissification Story.

The Sissy Taxi Ride – This is the story of Belinda and her unexpected sissy taxi ride in New York City…

Despite their best efforts, every sissy eventually gets out of line.  It might be that they touched their sissy clits without permission.  Or maybe they were channeling their inner brat and talked back.  Continue reading Punishing a Bad Sissy.

Caught Crossdressing!: Intentionally or unintentionally, many crossdressers find themselves “caught in the act.”

The Crossdressing Novice: Everything you need to know to get started on the road to gorgeous, sexy womanhood!

Guided Feminization: Between going it alone and coerced feminization lies an amazing world of Guided Feminization.

Crossdressing Men: Exploring and exploding the boundaries of gender.


Did you enjoy this sissy training and feminization erotica? Give one of our Sissy Training Mistresses a call, today!