Sissy School Sissy Training Mistresses

Sissy School Training Mistress


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Sissy girls are so much fun to play with- especially when they're trained to My liking! Classes with Mistress Hayden are now in session, and you're about to be introduced to a whole new curriculum. Welcome to Sissy School Orientation!

First, you'll need to change into your mandatory panties. This is the required uniform for all new students, and failure to comply will result in detention. We certainly wouldn't want that, now would we?

Now that you've got your panties on, it's time to get to know your Sissy Training instructor better! I'm a Feminization Mistress with a dynamic educational background perfect for training and transforming girls just like you. After completing My studies in fashion design and cosmetology, I continued My education in sexual psychology before delving into classes in the fetish community. Not only do I have an understanding of the nuanced training and discipline that different types of sissies require, but I'm equipped with everything you'll ever need to know to become the sissy girl you've always wanted to be! Now it's time to choose your courses. Take a look at each syllabus below, and report back to Mistress Hayden when you're ready to enroll. I'm sure you'll find the perfect class for your feminization aspirations!

Sissy Lingerie 101: Panties are lovely, but some sissies don't even have a collection to impress their Mistress with yet! This class will walk you through the different sexy panties that flatter sissies and panty boys the best, and where to shop for them. Next, we'll cover basic thigh-highs and pantyhose- My favorite accessories to make a sissy's legs look as glamorous or slutty as they like! Girls who are ready to enjoy a truly femme figure will also be welcome to learn all about bras and bralettes, and the perfect breast forms to fill them out!

Sissy Makeup 101: An art to some, and a foreign language to others- but all sissies can benefit from a pretty pink or red lipstick! You'll learn how to pick the sultriest shade and apply it just right- whether you're glamour girl coloring within the lines or an aspiring cockslut aiming for a smeared and garish walking advertisement. We'll also cover blush, mascara, and how to curl those lashes for a flirty flutter!

Bimbo Slut Training: This course is for the sexy bimbo sissy sluts who know just what they're good for, and they're ready to put it all out there! You'll learn how to style skintight minidresses with fishnets and slutty high heels, tips for walking in the platform stilettos the men love, and how to train your mouth and sissy pussy to take Mistress's strap-on cock until you're a skilled suck-and-fuck slut that the guys can't wait to line up for!

Advanced Sissy Lingerie: This is for My girls with an appreciation for detail and a penchant for vintage and couture lingerie. Here, we'll cover fully fashioned and RHT stockings, garter belts, girdles, corsets, and petticoats. Beautiful foundation garments are an essential for experienced femme submissives intent on pleasing their Mistress, and/or gentleman suitor.

Sissy Maid Training: Domestic servitude is one of the loveliest ways a sissy can serve a Mistress! Here, we'll discuss the proper attire for a sissy maid, address the household tasks you'll be required to complete, as well as proper protocols, greetings and mannerisms when attending to guests.

Exploring Sissy Humiliation: The desire to be feminized can often result in feelings of humiliation for multiple reasons. Maybe you realized you had a very small penis and suffered from emasculating thoughts. Commonly, sissies feel embarrassed about a desire to suck cock, and question their sexuality. Perhaps you have body image issues and just don't have the ideal look for a sissy girl. Here, we're going to break down all of your negative thought patterns and explore your responses. Humiliation can actually be very therapeutic for sissies when positive reinforcement is utilized to validate their identities. Before you know it, you'll feel great slipping your clitty silky panties! Sissies once reluctant to suck cock will be conditioned to accept the inevitable and worship properly. If I find your progress to be unsatisfactory, I'll have no choice but to subject you to The Board of Education as an advanced method of behavioral modification.

This could be your most interesting semester in your continuing education to date! I'm looking forward to meeting My new Sissy Students. Behave yourself, and don't be late!



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!