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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.


Graduation, in all of its many forms, is a time of change, and three major ones were on the agenda that night. Neither of us knew the other one was planning something special to take things to the next level, but fate has a funny way of taking things to a different level itself. Read A Femdom’s Crossdressing Guided Masturbation Story

One of the most common mistakes that sissies make, be they experienced or inexperienced, is the selection of their feminine clothing. Too many times, they try to wear what’s trendy at the moment or whatever they think is “feminine” without regard to what looks good on them. Assessing Body Type For Sissies can help you make better clothing choices!

I would have never seen myself as a panty slut or a sissy. The first time I put on panties was a moment I will never forget. They were white silk panties, kind of granny panties style, but sexy with lace. What really made these panties really sexy was a hole placed in the butt of them, with matching ruffles around it. Continue reading Sissy Slave Discusses Serving Strict Mistress.

Sissies often dream of more than stolen panties in a furtive wank. If you yearn to wear makeup and pass fully as a woman, read our two-part guide! Basic Makeup Guide For Sissies introduces you to the world of makeup, and Advanced Makeup Guide For Sissies takes you deeper into feminization via makeup.

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

One of my favorite pastimes as a feminization mistress is turning a man into a complete bimbo fuck slut. There is just something about seeing the breakdown and then the complete transformation. Bimbo training can be very intense, much more intense than regular sissy training, and can take quite some time. Read What Is A Sissy Bimbo?

Here at Suck Patrol, we want to ensure that you undergo a through training regimen so that you may learn all of the proper techniques of sucking cock. There are many things that sissies need to learn so that they can be turned into the proper pleasure slaves. Sissy boys often long to eventually be in a cuckold type of relationship so that they can watch their femdom Mistress be pleased in the way that she deserves by a big, hard dick. Read Learning To Suck Cock As A Sissy for more!

If you want to explore your sissy bimbo desires, From Normal To Sissy Bimbo Part 1, and then From Normal To Sissy Bimbo Part 2, can illuminate your path and give you some hints about how to get exactly what you’re dreaming of!

“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).

I love cock, yes I do! I love cock, how bout you? Woohoo!!! Reminds me of my cheerleading days! I’m a sissy girl and I’m not ashamed to cheer about my love of all things cock. I think about three things most of the time. They are, in no particular order, sucking on a big cock, dressing up in girly clothes and doing girly girl things. And I do all three as much as I can! Continue reading Sissy Cock Sucker.

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. You may even think you want to BE a sissy cuckold, but first you need to understand exactly what that is. Find out more by reading What Is A Sissy Cuckold?

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

Take your sissy training to the next level with one of our highly personalized sissy programs and training sessions, listed below. Feel free to reach out via our Live Help Desk or directly with the Mistress you’d like to work with. We’d love to get started creating a sissy training/feminization program to take you to the next level. Read about our Sissy Programs.

You may have heard of our tease and denial game, Pass the Penis, but have you heard of the new game of Pass the Sissy?  It’s quite a fun game where you go from one Sissy School Mistress to another as each Mistress continues what the previous Mistress began. Continue with Pass The Sissy.

Have you ever wondered how to act like a sissy? I have decades of experience with folks on all sections of the trans-spectrum. Not everyone considers being a sissy as a trans experience, but some do, so if you do, great! If not, no worries at all. You do not need to label yourself to be a sissy, that’s for sure. Read How To Act Like A Sissy for more!

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. Learn about the Seven Sissy Types, and determine where you fall! 

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!

Hello to all the sissies and fem-curious guys out there. My name is Toni. My Mistress has asked me to write this piece about how I became her good little sissy slut, and, of course, I agreed. I could never deny Mistress anything, even if I wanted to. It’s completely against my nature. This is just one sissy’s story, but maybe it’ll be helpful for you! Read A Sissy’s Story.

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.

The dreaded urge to purge …if  you are into feminization or sissification on any level, we know you’ve most likely purged your pretty, frilly things at least once. Read Urge To Purge: Effective Ways You Can Avoid It.

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.

One does not simply become a sissy overnight, generally speaking. Becoming a sissy actually involves a number of stages. Read The Stages To Becoming A Sissy to learn all the steps to sissification.

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?

It’s extremely rare that a man just wakes up one morning and decides that he should start dressing and acting like a sissy. Actually, it’s more than extremely rare. It just plain doesn’t happen! There is always some precipitating factor, something (or several somethings) that sparks his interest and slowly snowballs into a full-blown crossdressing fetish. Continue reading The Making Of A Sissy to explore how one goes from zero to slut!

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?

Each and every sissy needs sissy school training. That is a fact and not something we are going to argue. I know how you sissies like to have opinions about this, but no matter how good a sissy you are, you need a Mistress to guide you in all the ways of being a true female. Keep reading Sissy School Training Is In Session.

There are many types of sissy girls out there and each type of sissy girl has a unique flare to them, but one type of sissy girl that is always fun and amusing is a sissy slut. Read Ms Constance’s take on Are You A Sissy Slut?

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?

There are gradations and variables on the spectrum of male femininity and only you get to make the final choice of what you call yourself. I will help guide you, but keep in mind, it isn’t uncommon for a sissy to later find/feel they are really transgender… or the other way around. It’s crucial for you to allow fluidity in the feminine part of yourself. Read more in Am I A Sissy Or Am I Transgender?

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!

To be honest, I don’t even know how I ever let things spiral this far. This is my expose, I guess. Call it Sissy Boy Speaks! It had all started rather innocently. I mean, aren’t all guys just a little curious about things as they get older? I won’t lie. I remember the very first time I put on a pair of panties. 

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…

Now that you have your tools for strap on training, it’s time to put them to good use! Aren’t you excited? Being fucked by a strap on is a very common fantasy for sissy boys, so it would be quite unusual if you weren’t really happy about beginning your strap on training with Sissy Anal Training.

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.

My Mistress called me today and told me to pack a bag because we were going on a little trip. I was so excited! I literally danced around my apartment as I packed my things in a small overnight bag. Keep reading Sissy’s Night At The Department Store for one lucky sissy’s dream shopping trip! 

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.

Oh, panties. Every sissy longs for them and lusts after them. But there are so many kinds out there and so many choices as far as style, cut, fabric, and color that it can sometimes be a little overwhelming, especially for a new sissy. Panties For Sissies can help narrow down your choices.

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.

Here are Sissy School, we take your sissy training very seriously. In addition to the sissy school site, which contains many articles on sissies and feminization, we also have other feminization sites you may be interested in. Check out Other Sissy Sites!

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