One thing that I really love about the Sissy Pageant is that it’s not ‘just’ photos. Oh sure the photos are very fun to do and we all love helping you take spectacular images but the thing I’m most looking forward to is the QUESTIONS. I love learning more about you and hearing more about your sissy or feminization journey. Did you know that your answers will also help other people?
Sissy Pageant answers on our feminization podcast
Ms Erika and I do a BDSM kink podcast called The Weekly Hot Spot. I know that many of you are fans. Thank you!! I usually schedule a feminization or sissy training topic about every other episode. Here’s the episode on the Sissy Pageant. While you’re there, look around. There are feminization episodes. This blog on sissy training will give you links to a sample of the femme podcast episodes.
Check out this episode from last year’s event. This episode really hits a nerve for many ladies. It’s called: The Secret Sissy: Do you feel alone? You’ll hear just how important your experiences are to us and also others. Remember, whatever challenges you face you are not alone – we get it and we support you!
Enchantrix Empire
Many of you are already members of our free adult social networking site: Enchantrix Empire. If you haven’t already joined, you should! There are all kinds of girly girls participating in the Pageant. You can experience that sense of community with the LDW Mistresses and members of EE. Plus, you’ll be able to post cute photos, get ideas from other members, interact with the Mistresses and so much more!
How to participate in this year’s Sissy Pageant
To join, you’ll need to do a session of at least 30 minutes. This can be phone, Discord or texting. After the session, send an email to support@enchantrixempire.com. In that email include the date of your purchase, name of the Mistress you spoke with and the name you use on Enchantrix Empire.
It’s that easy to join!
Here are more specifics in this announcement post on The Daily Cock. Take a look and remember, if you have any questions reach out! Feel free to send me an email: olivia AT enchantrixempire.com. OH and don’t forget that there is the Live Help chat available as well, just click on any site and the live chat button will pop up.
Do you need a sissy slut resume?
This isn’t part of the pageant per se but take a look at the Sissy Slut Resume package we created for you. Ms Erika, Goddess Demi and I had a really fun time with this assignment package. And the resumes look pretty!
Remember we are all about celebrating YOU … in all your sexy, slutty, fun and frisky ways!
How are you feeling about the Sissy Pageant?
Let me know in the comments how you’re feeling. You can also send me an email or even connect on DISCORD. If we’re not already connected on Discord, just sign up and then do a search for LDWOlivia. You can search for any Mistress on Discord using LDWhername. We’ll be doing the actual show about the pageant in Discord anyway so if you haven’t signed up, you need to do it now!
Deadline and dates for feminization fun!
Remember, you need to have all of your pageant work done and sent in by July 12th. This gives us (the Mistresses) time to pour over the answers to the questions (my fav part), look at your photos and then vote.
We announce the winners in Discord on Saturday July 19th at 7pm eastern time.
Remember there are some really great prizes so get your sissy assignments done!
Your Experienced Mistress,
Ms Olivia

. Yay!!! I may not be a sissy per se but wow, last year’s pageant had some wonderful participants and everybody is always so helpful and supportive that I did not at all feel like an outsider. And the humiliation and embarassment were fun (you know how much I love that!). I’m looking forward to it and trying hard to get my submission sent on time! Thank you for this annual pageant!!! Too bad I can’t send in a dance video, hahahhahahaa! OMG.
Wait..ummm… that was a joke and NOT a suggestion. 😳.
Well you DID send in the pic with your skirt in motion and I knew exactly what the motion was from — you were swinging your lil ass from side to side … did you hear my voice in your head saying, “Wiggle that ass slut, work it!”
tee hee
I’m so glad you joined the Sissy Pageant … Ms Erika and I are going to do a podcast on answers to the questions part of the pageant … as you know the answers are my favorite part!
And your answers made me smile!
Hi Ms Olivia❤️ Last year the Sissy Pageant 2024 was announced, and boy (howdy🥰) did I hem and haw. How can I enter? I’ve only been around on EE a couple months.
A goofy post here and there, a comment a like a heart a smiley face… all led me to believe, “this is a place that understands me, and what I do.
Posting a pic on Outfit of the Day and being received so readily just convinced me to enter the pageant.
Ms Olivia, you are so right about the pix. Without a doubt mine looked a tad askew. Granted, it was what I could do in my situation, but sending them to get my okay to participate thrilled me. Hearing positive comments from EE friends and Mistresses only reassured me this was the right thing to do.
Yes, the questions! No one has asked me these questions. So to answer them honestly and freely was so liberating. Everything was from the heart, and I was filled with such a sense of satisfaction when I submitted my entry.
What happened, I never expected in a million years. Thank you to all the amazing entrants, the wonderful Mistresses, poring over pix, analyzing answers, and those behind the scenes who made this happen.
Best wishes to all the entrants this year. Thanks Ms Olivia!❤️
That Mets Jays World Series date I keep dreaming Bout is looking pretty good at the All Star break!🤭
I love that the Sissy Pageant inspires COURAGE ….
it’s a brave thing to do something that is new, challenging and/or scary.
I get it ….
you know, I get the butterflies every time I go to a new event – even when I know people I know will be there — it’s still a bit of jitters and afterwards it’s always WOW I’m so glad I did that !!