Sissy School Sissy Training Mistresses


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!





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$ per minute, minimum of 10 minutes billed to your credit card** – 18+

**If you have ANY questions at all regarding your charges, or if you think you have been charged incorrectly, please call (800) 375-0207 or email us at and a member of management will assist 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



What is a Sissy?


Darling sissy! Welcome to Sissy School! Come on in and meet out Sissy Training Mistresses.  What is a sissy, anyway?

Are you looking for a place where caring, alluring Mistresses will appreciate your girlieness? Sissy School is the perfect place for you! Whether you are a submissive sissy, a slutty sissy, or whether you just enjoy dressing up and feeling girly, the Mistresses of Sissy School will bring out the sissy in you, and give you a safe place to explore your feminine side.

So what is a sissy? And how is a sissy different from a “cross dresser”, or anyone else who enjoys exploring the experience of being the opposite gender from time to time? In meeting and getting to know thousands of sissies over the past decade, we have come to learn that each sissy defines herself in her own unique way.

But there are some things that lots of sissies have in common. First of all – panties! Whether you are a crossdresser, a submissive sissy, a slutty sissy, or even if you don’t consider yourself any of these, if you are reading this you almost certainly love the look and feel of sexy panties covering your private parts.


A Simple Sissy Experience


You don’t have to go all out with the toys, clothes and makeup if you don’t want to. Lots of sexy sissy phone sex sessions are all in the imagination. The Sissy School Mistresses are experienced with creating an amazing fantasy for you, using just words and imagination.

Anywhere your sissy self wants to go, your sissy Mistress can take you there. Just tell your Sissy Mistress what you have in mind, and she can create a wonderful girly fantasy just for you.


Sissy Panties


The great thing about sissy panties is, you can own 100 pair or more, and each one is unique in how it looks and feels, and makes YOU feel. Some gurls who consider themselves sissies reserve their panties for special occasions. Some like to wear panties under their clothes every day.

Some have a few special pairs, and enjoy looking at sites, or shopping in stores, where they can fantasize about how different panties would feel to try on. If you love panties too – and we’re almost certain you do! – make sure to have some very special, very sexy panties on when you call to have your sissy phone sex session with us.

Although not all sissies consider themselves submissive, we have a lot of sissies at Sissy School who do love to have a sissy Mistress take control. The sissy Mistresses at Sissy School enjoy directing a sissy, everything from dressing up in sexy frilly girly clothes, playing with toys like dildos, butt plugs and vibrators, even having a fantasy of being so seductive and feminine, that no one can keep their eyes off you men OR women!


Getting Ready for a Phone Session with Sissy Training Mistresses


Sometimes a great sissy phone session starts from the very beginning. You call, and your Mistress instructs you how she wants you to dress for her. You’ll describe all of the panties in your panty collection, and perhaps tell her what mood you’re in – obedient? Sassy? Sexy? Slutty? Whatever your mood, you’ll select an appropriate pair of panties.

And do you have a bra to match those panties? You’ll be instructed to fetch that too. And if you have some sexy thigh-highs or stockings with a garter belt – especially a super girlie color like pink, white, light blue – get those too! And if it’s stockings and a garter belt, make sure to put the panties on OVER the belt, so you can take them off quickly if necessary.

What about your face? Good little sissies have their face all dolled up for their Mistress. It’s especially important to have sexy lipstick on. You never know what you’re going to be asked to do with that pretty mouth.

Are you in the mood for sissy pink? Slutty red? Which color matches your panties best? The best thing to do is to have a few colors for your Mistress to select from when she dresses you up. And a little blush (or a lot, if you’re feeling extra slutty!), some eye liner, powder and mascara makes your sissy look complete.


Advanced Sissy Training – Bring Your Toys


And we mentioned toys earlier. If you are a kinky sissy, you may be interested in reading below! Lots of sissies and Sissy Training Mistresses like to incorporate toys into a sissy training session. What kind of toys are we talking about? Let’s explore…


Dildos & Vibrators


Playing with a dildo during your sissy phone sex session can be very arousing, both for the sissy and the Mistress. Many sissy Mistresses enjoy instructing their sissy to play with their dildo… If you’re interested in getting a bit kinky, have your nipple clamps ready when you call.

If interested in exploring sissy anal training, beads can be a great place to start. There are lots of small sized beads to start out with. Use them as your Sissy Mistress instructs for an exciting, explosive experience..