Sissy School Sissy Training Mistresses

Sissy School Training Mistress


You've never been a real man, you know it and I do too. Soar to new sissy heights with Me.


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You have a secret one you haven't shared, or have shared sparingly. It's a secret that will blow the minds of those nearest and dearest to you. You love to feel fem but your desires go way beyond that, doesn't it? At first, you thought it was curiosity, you were interested in feminine things, panties, slips, stockings, something like that, right? You told yourself that it was just an erotic curiosity, women look damn sexy in them, how do they feel? You found out, didn't you? They feel heavenly! Not like the scratchy cotton you've grown accustomed to.

But then something happened, you needed to try them on, and when you did it was EXPLOSIVE! The only question I have for you is where has your sissy journey taken you? Every sissy is different like sweet little snowflakes no two are the same! From sensual and blushing being teased into panties, to comportment training and moving and acting more fem! Many who have sissy desires sink deep into kinky play along with their feminine dreams. Some follow the chastity path, after all, chastity increases your fem feelings! You'll feel more fem, sexy, and yes sometimes slutty, and is way more intense when you are horny and denied. Other sissy gurls, move along and explore their bi-curious desires with Mistresses Strap-on or hopping on the cock train, live and in person!

Knowing this about you, and knowing you are curious to explore the depths of your sissyness, the question is: how curious? Hmmm? Curious enough to employ my feminization and sissy training skills and find a new level of femininity or the depths of your sissy slut desires, that you never thought existed or were possible? I bet you are. Because playing alone, and keeping that secret can only go so far! Everything is better when you have the soft firm hand of a Woman, isn't it?

Even if you are far down your sissy journey, and looking for some fun I'm ready to play! I am always so impressed, and amused, and enjoy your sissy journey tales while we create some of our memories!

I offer all types of sessions, including the traditional phone session, texting, and voice (cam) over Skype to help make your sissy dreams come true! If you are still on the fence, I appreciate that! I also offer lots of fem fodder for those too shy to reach out (yet) I am on a podcast with Mistress Olivia called The Weekly Hot Spot where our sissy gurls and conversations about you are plenty! We also have some feminization and sissy challenges in our Assignment store that have received RAVE reviews and have helped many!

Cum, explore with Me, my sweet sissy. How far will we travel down your sissy path? I want to find out! I can't wait to meet you!



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!