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Harper

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Email me at Harper@enchantrixempire.com

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Once upon a time there was a little boi who loved all things girly. Corsets and lipstick; garters and pantyhose. The first time he tried just a dab of lipstick (taupe, so secret, so safe) and felt the slick smoothness of it on his lips, the sweet taste on his tongue, the subtle shine in his reflection -- he nearly fainted.

His dreams and fantasies frightened him; all that he had been taught about his own sexuality told him how very naughty he was to be thinking about makeup, dresses and fabulous shoes. He tried to ignore it, to pretend he didnt feel what he felt, want what he wanted.

One day the boi heard of a place, a secret hidden place, where little bois like him went to learn how to be perfect, pretty sissies. A School for Sissies!

He was so excited, so nervous. What would he learn, who would teach him? In my classes, my sweetness, you will learn how to wear your makeup, style your hair, and dress for ~every~ occasion. Once you have mastered the outward appearance, the demeanor, we can move on to more advanced lessons.

I know that you dont just dream of frilly dresses and fabulous lingerie. You fantasize about all the things girls get to do. Sleepovers, flirting with hot guys, dropping to your knees and opening your mouth. Other, darker desires.

Welcome to school, my sissy boi. Pay attention to your lessons, listen well, and we will have the most fabulous times together.

Ms. Ally and all of the SissySchool Mistresses would like to take this opportunity to welcome Sissies across the world to SissySchool. At last, sissy – you’ve found your home on the Web. The Queendom of sissification. And it’s very pink, very frilly, and very girlie.

CLICK TO READ MORE ABOUT SISSY

What is a Sissy?

Darling sissy! 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 Sissy Phone Session

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 Mistresses like to incorporate toys into a sissy training session. What kind of toys are we talking about? Let’s explore…

  • Dildoes & Vibrators

    Dildoes & Vibrators

    Playing with a dildo during your session can be very arousing, both for the sissy and the Mistress. Many sissy Mistresses enjoy instructing their sissy to play with their dildo...

  • Nipple Clamp

    Nipple Clamp

    If you’re interested in getting a bit kinky, have your nipple clamps ready when you call.

  • Anal Beads

    Anal Beads

    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 Mistress instructs for an exciting, explosive experience...

$2.75 per minute

Minimum of 10 minutes | Billed to your credit card | 18+

WHAT WE OFFER

We offer Sissy Training,
Panty Boy Training, Sissification Training,
Crossdressing and Feminization Phone Sex For Sissies,
and Strap On Training for Sissy Sluts as well as Sissy Stories,
Free Sissy Audio, Sissy Chat – and All Things Sissy!

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This site contains adult material, and is intended for use by Adults Only.
You Must Be 18 or older to enter this site…

All About Sissy School

Ms. Ally and all of the SissySchool Mistresses would like to take this opportunity to welcome Sissies across the world to SissySchool. At last, sissy – you’ve found your home on the Web. The Queendom of sissification. And it’s very pink, very frilly, and very girlie.

Enjoy your crossdressing sissy training! And if you aren’t searching for sissy phone sex, sissy domination, sissy cuckold training or sissy maid training at this time, feel free to browse and use the free sissy features that we offer to the sissy community. We have built the SissySchool exclusively for the sissy world, and we want you to become a part of our Girlie community of over 30,000 sissies. You can even learn about Sissy Pantyhose here at Sissy School.

We Will Teach You How to Be the Perfect Sissy Girl or Sissy Boy!
Come on in Pretty Sissy – Mistress Wants to Teach you a Lesson!

How do I Crossdress? We’ll Show You How…

  • What Is Sissification?

    What Is Sissification?

    The Mistresses offer their definitions, based on their experiences with sissies...

    what is a sissy
  • Going Out Dressed as a Sissy

    Going Out Dressed as a Sissy

    How can you ease into going out cross dressed?

    sissies going out
  • Sissy & Sissy Maid Training

    Sissy & Sissy Maid Training

    We offer 1-on-1 sissy training & our free crossdressing chat for group sissy training...

    the mistresses
  • The Sissy Husband

    The Sissy Husband

    A short essay on sissy husbands, married crossdressers and those who love them...

    sissy husband
  • Telling Your Significant Other

    Telling Your Significant Other

    How to tell your significant other that you are a crossdresser...

    sissy coming out
  • Frilly Sissy?

    Frilly Sissy?

    Do you enjoy looking at, wearing and prancing around in pretty, frilly, lacy clothes?

    frilly sissy
  • The Sissy Housewife

    The Sissy Housewife

    Dreamed of being the perfect housewife sissy? What does it entail?

    sissy housewife
  • 50

    50's Housewife Sissy

    Want that 50's lifestyle of dresses, dinner ready and the spotless house?

    50s sissy housewife
  • Talk Like a Woman

    Talk Like a Woman

    Read about how to talk like a woman...

    talk like a woman
  • Feminine Hair

    Feminine Hair

    You can do a lot to make your hair appear more soft and feminine...

    sissy hair
  • Feminine Eyes

    Feminine Eyes

    When crossdressing, it's important to have the right make up...

    sissy eyes
  • Are You an Anal Slut?

    Are You an Anal Slut?

    Love anal porn? Plugged for hours? Need it up your ass? Find out if you are an anal slut...

    anal slut

Sissy Training

SissySchool offers sissies, crossdressers and sissy maids many, many fun things to do, in addition to our sissification training, sissy maid training, coerced feminization, sissification stories, and Sissy phone sex services: we are much, much more than a sissy phone sex site (although if you are looking for sissy phone sex, you’ve found the best here!) – the Femdom Mistresses at Sissy School offer sissy phone sex training, training for pantyboys, coerced femimization, sissy domination, sissy maid training, and online sissy maid training.

What is Sissification? What is a Sissy?

By clicking on the links on this page, you agree to the following: I do not find phone sex, pictures of nude adults, or other sexual material and erotic stories to be offensive or objectionable. I am at least 18 years of age and have the legal right to participate in adult chat and view sexually explicit material and adult material in my community. I understand the standards and laws of the community, site and computer to which I am transporting sexual explicit pictures and adult material, and am solely responsible for my actions. If I use these services in violation of the above agreement, I understand I may be in violation of local and federal laws and am solely responsible for my actions. By visiting www.sissyschool.com from any and all liability which might arise. This site complies with: 18 U.S.C. ‘2257 and 28 CFR 75 compliance notice: All persons depicted herein were at least 18 years of age at the time of photography, and all performers on this site are at least 18 years of age.

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