Sissy School Sissy Training Mistresses

Sissy School Training Mistress


Governess Femdom of Sissy Bois


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Welcome girlie boi. I'm Mistress Cassandra, your Emasculatress, Humiliatress, and all around pussy-whipping real Girl that will guide you through a world of sissy subservience.

I've been studying you for awhile sissy, and your girlie brain is a combination of feminine pink cloud dream dressing, and fetish inspired stroking......aren't you so pretty. Just look in the mirror. It's what you do best. Aren't you so hard and sexy under those pink nylon full cut panties? But you cannot play with that yet, not until I say. Not until I have made you over in MY charm school. You will play by MY rules if you want to be the ultimate pantywaist. You are MY dolly to dress up, make up and play with, and your tongue had better be ready for sissy style servitude. If not, then it's tied up and spanked-sissy time.

Let's start with the basics. Your body shaved with pink gel and pink razor, floral douche and of course a heavenly lavender bubble bath. As you're relaxing with your rose masque, I'll be busy burning all of your "man" clothes. After your bath I will inspect you thoroughly, and watch carefully as you apply your daily "Lady Cassandra's Magic Feminizing Cream" all over your smooth body (concentrating on that sissy stick and those disappearing little marbles).

Then comes the wardrobe: depending on if I've decided you'll be a maid in crinoline, satin, lace, and fishnets; OR a slut in fuck me pumps, mini skirt, DD breast forms and a cocksucker, "I'll make you money, Mistress," attitude. Maybe I'll decide on a teen sissy afternoon at the mall. I can't wait to hear the music of teenaged bitches pointing at you, giggling and saying..."Look at that sissy in pink carrying all of those packages for that girl!!!"

Maybe Tinker Bell likes being in a Girl and sissy-only party because she's a submissive little lesbian. She likes being on the bottom as Mistress guides in the strap-on and makes her moan like a little porn star. She may like sissy sex under the direction of Mistress.

Yes, I'll have a ball reinventing you, but one thing darling: you will never be as good or as beautiful as ME. I am a superior, genetic Female and you are just a sissy. You will never be "man" enough to satisfy Me either, so get used to your place in My universe: on the floor, foot of the bed while Mistress entertains a "real" man.

Awwww don't cry little sissy. If you're good, you can have the cream pie. And make sure you are en femme when you call.



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!