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Sissy Fashion Show: Frilly

This text is available for purchase but you need to login or register first. Mistress Simone shows off her sissy Brenna in some of the frilliest ultra-feminine frocks the Studio Chicago has. She goes...

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Sissy Fashion Show: Slutty

This text is available for purchase but you need to login or register first. Mistress Simone continues to show haute couture for sissies in this clip with a selection of outfits to bring out the inner...

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Makeup Exploration: Lipstick

This text is available for purchase but you need to login or register first. Alice in Bondageland continues the transformation of Monica by adding lip liner and lipstick in this clip. Along the way...

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How to Shop for a Sissy, Part 1

This text is available for purchase but you need to login or register first. Making your sissy look truly fabulous can be a challenge when it comes to finding the right size clothing. Brenna and Miss...

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How to Talk to Your Sissy

This text is available for purchase but you need to login or register first. Miss Simone talks in this clip about how language changes when you’re dominating a sissy boy. Instead of cocks and asses...

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Sissies, Cross-Dressers, & Feminization…Oh My!

This text is available for purchase but you need to login or register first. Sometimes language can be confusing, so in this clip Miss Simone takes the time to talk about what she considers to be the...

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Wigs: The Natural Look

This text is available for purchase but you need to login or register first. One of the most important aspects of sissification is choosing the right wig, and that’s why Mistress Simone dedicates two...

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Sissy Fashion Show: Daywear

This text is available for purchase but you need to login or register first. Miss Simone continues her parade of looks for sissies with four outfits designed for everyday activities. She goes over the...

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Wigs: the Playful Look

This text is available for purchase but you need to login or register first. Miss Simone and Sissy Brenna show off some of the more whimsical kinds of wigs in this clip. Miss Simone talks about...

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How to Shop for a Sissy Part 2

This text is available for purchase but you need to login or register first. In Part 2 of this series on how to get the right clothes for your sissy, Brenna and Miss Simone discuss a few more...

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How to Talk to Your Sissy

Miss Simone talks in this clip about how language changes when you’re dominating a sissy boy. Instead of cocks and asses they have clits and pussies, and in general a more feminine (but no less...

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Sissies, Cross-Dressers, & Feminization…Oh My!

Sometimes language can be confusing, so in this clip Miss Simone takes the time to talk about what she considers to be the difference between cross-dressing, sissification, and feminization. Some of it...

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Wigs: The Natural Look

One of the most important aspects of sissification is choosing the right wig, and that’s why Mistress Simone dedicates two long clips just to this subject. In this one she and Brenna talk about how to...

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Sissy Fashion Show: Daywear

Miss Simone continues her parade of looks for sissies with four outfits designed for everyday activities. She goes over the different materials including choice of shoes and other considerations. Each...

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Wigs: the Playful Look

Miss Simone and Sissy Brenna show off some of the more whimsical kinds of wigs in this clip. Miss Simone talks about different events and situations where you might want to play with each type as well...

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How to Shop for a Sissy Part 2

In Part 2 of this series on how to get the right clothes for your sissy, Brenna and Miss Simone discuss a few more non-commercial ways to acquire the right clothing, such as FetLife forums where you...

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