It has taken me a few days to be able to process the wonderful Sissy Pageant we held June 28, 2024. It was actually a pretty extensive lead-up of over a month of prep with pictures of the girls as well as answers to Pageant Questions we Mistresses asked.

Overview of the Sissy Pageant

I won’t explain every detail like we did pre-Pageant, but here’s what the outline looked like:

  • Putting three pictures up on our social group, Enchantrix Empire, that showed off their style and sexiness.
  • Mistresses were judging on Legs & Ass, sissy Style, and Sex Appeal
  • Answer 4 questions
    • What is your biggest Sissy or crossdressing challenge? What parts of being feminine are most tricky for you to handle?
    • If you could travel back in time and give yourself any advice about your sissification and feminization journey, what would it be?
    • Crossdressing is great, but how do you maintain that Feminine feeling when you’re not all dressed up? Think in terms of Undercover or Stealth Femme tricks, your little daily Sissy Rituals, and Sissy Attitude!
    • Sissies, crossdressers, and trans women often have an idea in mind about what their perfect Ideal Femme Self Image might look like. Describe your vision of who you would like to be!

How I Judged the Photos

What was so great was there were girls of all styles in the Sissy Pageant contest. From slutty to business casual. We knew almost all the girls from Enchantrix Empire (and if you are not there, why not?!?) and it was a delight to see the women as they saw themselves. I loved that their personalities almost always jelled with their clothing personalities. Not always and that was a fun surprise. The woman you thought was going to be quite the frisky one turned out to be the one most conservatively dressed. I loved it!

I was also thrilled me to see girls of different sizes and shapes. It is tough for us women to show our bodies to strangers when we aren’t model thin or fitting into society’s idea of the perfect woman. It was an absolute joy to see these women unabashedly demonstrating their beauty… both inner and outer. Every one of them excited me! (Not kidding.)

I focused in on how the women were standing, how they held themselves. We didn’t see faces on most, but if they did share their faces, I could look into their eyes and easily saw their hesitant delight at showing themselves off. For many, this was the first time they ever dressed for someone else; they’d spent their whole lives dressing only for the mirror.

It was an absolute honor that we were shown their most vulnerable selves. Not one of us Mistresses took that for granted. We all were flabbergasted at the incredible displays of feminism that came across the wires by way of the camera’s shutter.

In my next post, I will share my feelings about their answers to the questions posited to them. Please be sure to check that out because I think you will be just as touched and delighted as we Mistresses were.

EE Sissy Pageant Phone Sex Mistress Daphne (800) 601-6975

Be sure to read Part 2:

My Take on the Sissy Pageant (The Questions Answered)