Sissy School Sissy Training Mistresses

Sissy School Training Mistress


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My Dearest Future Sissy,

As I write this, I am excited for the day when I get to introduce you to the world of sissy play. I can already picture us in our matching pink ensembles as we prance around town and show off our femininity. I have so much planned for us and can't wait to share all the joys of sissy play with you.

I will teach you all the basics of being my sissy. We will explore everything from maid training to forced feminization and even pegging. I will ensure that you are dressed head to toe in frilliness and that you have all the sissy gear you need. You will learn the art of makeup and how to properly apply it. (You will be the prettiest little bitch around) You will learn to be the perfect sissy and I will take great pride in your progress.

When we go out on the town, you will show off your newfound sissy skills. We will go to girly tea parties, where you will be the most perfect sissy in attendance. We will visit the mall and shop for pink and frilly clothes for you( I may even send you on adventures and listen to the shop girls teasing you about your newest cheeky panties). We may even go on dates with men, Big, glorious, well-hung men, and you will show off your feminine charms.

You will learn to do all the stereotypical sissy tasks and become my virtual Stepford wifey.

And when we are alone, you will learn to please me in every way. We will explore the world of BDSM, and you will learn to obey my every command. I will teach you the art of pegging and you will learn to take pleasure in it. You will try to act like you don't want it, but in the end, you will beg for every single inch of my strap-on, both orally and in your sweet little Mangina. You will learn to enjoy being feminized, and you will learn to take pride in your femininity.

So my dearest sissy, I can't wait for the day when you are ready for us to embark on this journey together. I promise you that it will be a journey full of fun, pleasure, and exploration.



Can’t decide on just one Mistress to speak with? Add a second Mistress to your call for just $1.60 per minute more.  Two Mistresses aren’t enough? No worries! Each additional Mistress is just $1.60 per minute more!

Here’s the breakdown:

One Mistress – $2.99 per minute

Two Mistresses – $4.59 per minute

Three Mistresses – $6.19 per minute

Four Mistresses – $7.79 per minute

Five Mistresses – $9.39 per minute


Why Sissy School’s Sissy Training Mistresses are the Best!


Welcome to Sissy School! You may be wondering whether or not the Sissy School Sissy Training Mistresses are the best sissy trainers out there, and the answer to that question is simply, yes.

Here at Sissy School, we have a wide variety of sissy training mistresses, each with their own domination style and sissy training style.


Do You Need a Strict Mistress, a Sensual Mistress or a Good Combination of the Two?


Do you learn and respond better to an authoritarian Mistress? One who won’t take any back talk and is firm in her expectations of you? Or do you do better with a sensual, encouraging Mistress?  Perhaps, you are like most sissies and need a little mix of both!

Whichever type of sissy training Mistress you need, Sissy School’s Sissy Training Mistresses have got you covered. We’ve got Mistresses who are purely sensual, Mistresses who are purely strict, and Mistresses who are a good mix of both!


Click on the Sissy Training Mistresses Pics to Learn More about Them


By clicking on the picture of each Sissy Training Mistress, you can read their sissy training bio and learn about their styles and expectations. From there, you’ll also find links to their blogs, voice samples, contact information for Skype and Twitter, and much more.

If you’ve read about many or all of the Sissy School Mistresses and are still unsure which one may be right for you, our Erotic Concierge can help narrow it down for you.  Just go to, answer a few questions, and submit the form.

Within 24 hours-oftentimes much quicker than that-our Erotic Concierge will get back to you with several Mistresses who may be a good match for you based on the answers to your questions.


Time to Take the Sissy Training Plunge!


You’ve known-or at least suspected-for a while now that you may be a sissy. Don’t you think it’s time to quit fighting it and embrace your inner sissy? Give one of our Sissy School Mistresses a call for sissy guidance, today!