Sissy School Sissy Training Mistresses

Sissy School Training Mistress


The Softer Side of Mean


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"Mistress, am I a sissy?"

I've been asked, on several occasions, to define what it means to be a sissy. Is it just a man wearing panties or does there need to be more to get the qualification? At which point do you change over from being a "panty boy" to being a full-fledged sissy and what does that mean for your future?

There are a variety of answers to this ... each one unique to the individual coming to me with the question. I always ask, in response, "Well, do you FEEL like a sissy?" and begin exploring the answer from there. Have you always been like this or is it a new development? Is it something you feel is a part of your life or just a sexual drive? (Note: Both of these are completely valid responses, there is no right or wrong answer).

How Can I Be A Better Sissy?

Here's where it gets interesting. This is where I can help to mold you ... guide you ... and pervert you into being the perfect sissy for my use.

Are you a sissy who wears panties but wants to be better dressed?

I am a fashionable Lady who can help you to achieve any look you desire, from a stylish doll to a trampy little slut. I can help direct you to the makeup tutorials and fashion trends that will keep you looking your sissy best. I specialise in lingerie and retro-sissy looks .... there's nothing sexier than a sissy done up like pin-up bimbo!

Are you a sissy that loves cock?

To say I specialise in cock training is an understatement. This is where my strength comes out ... I own 15 strapons and I will teach you how to deep throat each and every one of them. After all, a good cocksucking sissy should know how to please both her Mistress AND the man her in life!

Do you need a confidante?

Every girl needs a friend they can go to coffee and confess their secrets to. Care to share with me about the first time you nicked a pair of knickers from the dorm laundry? Or the first time you took a man's cock in your mouth? I promise you ... your secrets aren't exactly safe with me but I do love to hear them anyway.

A Kinder, Gentler Sissy

In the end, whether you are a sissy or not depends entirely on what you feel ... and what I can make you do!



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!