Sissy School Sissy Training Mistresses

Sissy School Training Mistress


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Welcome to Sissy School! I am your instructor, mentor and Goddess. Here you will begin your journey to becoming the perfect sissy boy. I love helping guys just like you connect to that you have been hiding deep down for so long. Do you crave dressing up from head to toe? Together we will find the perfect outfits that reflect who you are. We can shop, talk, and play.

We will explore how you got here, and then turn you into a panty loving fem-boy. If you have had past experiences, I want to hear every detail. After all, the more I know, the more I can help you grow in your sissy boy journey.

Discovering your fantasy in Sissy form

Whether you want to serve your Goddess in Sissy form or you want to explore cock and the male form, every lesson will help you explore in ways you can't even begin to imagine. We will start with my fingers and work towards bigger and better things. Can you imagine learning to deep throat and take a real cock between your lips and learning how to suck to perfection. Maybe I will lock up your cock, and keep the sissy in chastity while you are learning about all things feminine. After all, what could you possibly need it for?

Anal Training

Once I have you locked up, we will begin official Anal Training. If the sissy has not explored this kink, I promise it won't disappoint. You will learn how to prep, position and get pumped...literally. Every sissy must learn how to have an anal orgasm. Once you know the ropes, I will intensify the lesson. Yes, I can edge your ass instead of your cock.

Sissy Service

Post graduation, it's time to serve. Oh the fun I will have showing you off, while you serve my friends at parties, or perhaps at the local sex club. You will soon learn that the sissy belongs to me, and I will use you as I see fit. Be it cooking me dinner, giving me a message, or bending over.



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!