Sissy School Sissy Training Mistresses


You Might Need Sissy Training but Not for the Reasons You Think!

by Mistress Olivia of


Your Sissy Training Starts Here at Sissy School (800) 730-3507


When you think of a sissy training program, what comes to your mind?  Most people think feminization training means being a certain type of sissy, like a sissy slut.

A naughty sissy is a lot fun but that stereotype is too simplistic. People are complex. You are unique. You deserve someone who knows that you are special.


Are you a sissy? Take the sissy test.


Sissy Mistress Sissy Types (800) 601=6975Wearing panties or women’s clothes doesn’t automatically mean you’re a sissy.  Are you a crossdresser or a transwoman?  You might be an alpha male in other areas of your life and submissive when en femme.  You might be attracted to a man, woman, transwoman, or a shemale. 

These are all examples of labels. You might be any or all of these designations at any point in time. Just remember you are more than a label. When you’re in sissy school, your Mistress will give you encouragement, guidance and assignments designed just for you.

One sissy puts it this way: “It’s like there’s male and female that society defines certain ways, but people tend not to really fit into them. It’s important to explore, experiment and find out what kind of girl you are; how much you are in one part, how much in the other and whereabouts you fit into it.”  

Here at Sissy School, you’ll find a variety of women. Read the bios and listen to the audio samples. Also check out each of the Mistress’s blogs.  Each woman is unique with her own experience, style, and skills. You might have only one Mistress or a variety of Dominant women who can be your sissy Mistress.


How to pick your perfect sissy training Mistress.


Feminization Mistress Feminization Phone Sex (800) 601-6975You want someone who will ask you questions about your life, experiences, hopes and dreams. There are so many questions. Your Mistress will want to really get to know you.  I ask a lot of questions. This is fun girl talk about lingerie, hair and makeup. Maybe we’ll talk about guys. We can do a roleplay or explore BDSM and kink play.  I need to know you to know how to guide you, encourage you or, even, discipline you. Here are some of the things I want to find out about you

  • Do you think like a girl?
  • Will your feminization include reprogramming to give you a feminine mind or make you into the best sissy?
  • Is your experience about the feel of silky panties? Are you a heterosexual man in lingerie?
  • When en femme are you aroused by men, women or both?


Sissy Training: Sissy types and femme girls


This is by no means a complete list. These are just some options to get you started thinking about what you’d like to explore:

  • Are you a sissy slut or a bimbo?
  • Do you want to be used hard or have a nurturing woman at your side?
  • Have you thought about being a 1950’s housewife or sissy Sissy School Sissy Training Methods (800) 601-6975maid?
  • Are you, perhaps, a cuckold sissy husband?
  • Speaking of being of service, when you’re dressed in women’s clothes, do you want to serve a woman or a man? 
  • Do you like humiliation or physical pain play?

All these questions are why it’s so important to have someone who understands the nuances of sissification and feminization.  If you are being trained to be a sissy maid but you have the mind (and body) of a sissy slut, you’re in the wrong training program!


Types of feminization training


I like doing training that includes a mixture of encouragement, guidance and instruction.  Sometimes, I’ll put sissy in chastity to … ahem … enhance her dedication to her sissy school lessons. Discipline like spanking might be punishment or funishment.

If you already have your femme style and desires identified then Mistress might push your limits a bit so you can explore some exciting options. Creativity is key to a feminization training program. You will have a safe place to experience who you really are and who you want to be. This could be fun with fashion all the way to sensational sex with remote sex toys!  Remember, feminization is just the beginning … sissy dreams do come true.


Ready to begin your sissy training? Give one of our Sissy Training Mistresses a call, today! 


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