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Sissy Snow Day Challenge

The Amazingly Talented Janet Made This Lovely “Fiona Gets Her Wings” Portrait THANKS BABE XOXOXOXO

Sissy Snow Day Challenge


So the weather outside is frightful indeed here in the mountains of MD. As one of my lovely panty pets asked, “How many big cocks worth of snow do you have?” Well, depends on . . . → Read More: Sissy Snow Day Challenge

Fiona’s Blog Update

Upcoming News and Happenings for Your Kinky Consideration


New blog series will be introduced to my site: The Goddess Guide -Moon Centric Celebrations Honoring the Divine Female Energy in us all by celebrating different aspects, lore, legend in both ancient and modern times within and outside ourselves and the cycles of life.


. . . → Read More: Fiona’s Blog Update

Sissy Beauty Question Answered



Question From Sissy Sue Ann:

Mistress how do I cover up my freckles? It seems like my foundation doesn’t do the trick.

Answer: Freckles are so adorable. I have a few on the bridge of my nose in fact. Personally I like that expression “a face without freckles is like a sky without . . . → Read More: Sissy Beauty Question Answered

Holiday Nosh Sissy Fitness Quiz Part 1


Sissy Feasting Fitness: What Kind of Holiday Nosher Are You?


The holidays are a wonderful time of year to indulge and pamper ourselves. It can be a battle to balance trying to enjoy ourselves and not overdoing it but also not overly restricting our traditional eat, drink, and make . . . → Read More: Holiday Nosh Sissy Fitness Quiz Part 1

Sissy Maid Quiz


Find Out Here Share with the class:


Which Sissy Maid did you get?

. . . → Read More: Sissy Maid Quiz

Sissy Session

Sissy Session with a side of Humiliation

In keeping with the recent theme of Panty Pets and Sissy Missies I wanted to give a little shout out to:

Cody La Senza the panty pet! Cody is another little humiliation whore of us ladies of LDW. A communal kink toy . . . → Read More: Sissy Session

Gurl Talk 4

Gurl Talk


I had a wonderful session with the fun and sexy “CockSuckingCrossDressingSissyFag” aka CSCDSF. So vibrant, vivacious and dressed up perfectly for me we had a blast! Here is our Gurl Talk interview we did afterwards via email.


*The following is shared with express permission from CSCDSF*

1. What does . . . → Read More: Gurl Talk 4

Sissy Panty and Hosiery Challenge Quiz

Sissy School & Panty Pet Class is in Full Swing!

So my little sissy darlings I have been lucky enough to have been inspired by my recent sessions with panty pets to create a sissy fashion challenge. The quiz below is a fun little testing of your knowledge. From sissification faves centering on lingerie, types of . . . → Read More: Sissy Panty and Hosiery Challenge Quiz

What It Means To Be A Girl

  Reclaim The Girl or Gurl You Truly Are!

Miss. Fiona  why are people sometimes so unaccepting of sissies? What’s wrong with wanting to be girlie? -Nancy

That is a great question with no good answer unfortunately. You should be able to get your girl on without judgment or condemnation. It’s fun to . . . → Read More: What It Means To Be A Girl

Fiona’s Follies: Let Yourself Shine

Talent Wanted   Impress Your Empress  Entertain & Amuse Your Mistress Make Your Goddess Giggle


Who: Mistress Fiona wants YOU. All you spectacular strokers, sassy starlet prissy missies, pervy performers and creative cocksuckers. What: Talent Search for new entries in Fiona’s Toy Chest: Class Pets Hall of Fame. You can put on display your fave talent or . . . → Read More: Fiona’s Follies: Let Yourself Shine