Fans of both Sissyville and the Enchantrix Empire have been longing for a return to the days when we hosted our Sissy Pageants, and at long last we’re back! The Enchantrix Empire Sissy Pageant for 2024 is finally here! This is a chance for you, dearest sissy, to strut your stuff and show off all your many talents in front of the Mistresses and your fellow sissies, and win prizes at the same time. All you have to do is join our social network, share some hot pics of your sissy self, and answer a few questions. Easy peasy!

Announcing the 2024 Sissy Pageant

This year for the Sissy Pageant we will be offering three prizes to our lucky pageant queens. Second runner up will win themself an all expense paid trip to, wait, no, that’s not quite right… Second runner up gets 20 FREE minutes with the Mistress of their choice! First runner up will enjoy 30 minutes in heaven at no cost to themself, and our Grand Prize for the Queen of the Sissy Pageant? An hour of luxurious sissy joy spent with any Mistress they choose! Sissies can redeem their free minutes with any Mistress, though I’d suggest one of our sissy experts to truly maximize your experience with us.

Inclusive Pageant Standards

We adore all of you and want to get to know YOU better! That’s why we’re doing this pageant. We want all of you to participate — if you’re a sissy, crossdresser, transwoman or however you identify. Everyone is welcome to participate!

Enchantrix Empire

The Pageant is a virtual experience, rather than an in-person event. You will need to have or create an account on our Enchantrix Empire social network. There is no cost to join us, no ads on the platform, your data will never be sold or used to market specialty dildos to you, and your images and blog posts on our network will remain utterly private. Our social platform has been created with privacy in mind: internet content scrapers can’t get to anything posted on our site, so you never have to worry about being exposed without your consent! Once you have your account (and there will be a short delay to have your account approved, as we use actual human effort to manually approve new member requests as well as password resets), you can create your profile, upload images (within our TOS please!), and interact with other sissies, slutty perverts, and the Mistresses.

There is a group already set up on the Empire that you can join, and that’s where you’ll share your pictures to be judged in the pageant!

The Sissy Pageant

Sissies, you’ll need to upload THREE pictures of yourself to our group on the Enchantrix Empire. Your pictures may show your face or not, as your own comfort dictates. Choose your three pictures carefully, we’ll be judging you on three categories: Legs/Ass, Sissy Style, and SEX APPEAL! In each image please include a piece of paper with your Enchantrix Empire username written on it in three inch high block letters. We want fresh, hot, sexy, and fun images! While running your image through a filter to make it sexier can be a lot of fun, for the Pageant please do NOT use AI or filters on images you submit to be judged. We want to see YOU, darling sissy, in all your glory. Show us the REAL YOU.

The Real Person You Are

In addition to judging you based on the images you share with us, we’ll ask you to answer four questions. A simple Google form (please feel free to create a new email to use for this, even though we absolutely will NOT be keeping your emails or signing you up for any mailing list) with five questions for you to fill out. One question will be “What is your Enchantrix Empire username?” We ask that one so we can match your answers to your pictures! The other four questions? Well, you’ll have 500 words each to tell us about your challenges, advice to your past self, and more. This is the part where your personality will shine!

Sissy MistressWhile we will never use your images without your permission, we may, in the future, use your answers to the questions to inspire blog posts, informational posts and further events.

The Pageant Is Open May 15th through June 15th

Submit your pictures, and answer the questions sometime between May 15th and June 15th to be entered to WIN free minutes with your Sissy Mistress. If you’re feeling insecure and a little shy, please do book a session with any sissy Mistress to get help, advice, and guidance on how to act like a sissy as you prepare your pics and answers! On June 28th at 8 pm Eastern we will host a live chat event to announce our winners in our Community Kink Chatroom. Even if you didn’t participate, you’ll want to be there, because all the Mistresses will make an appearance, and you just can’t miss out on the 2024 Sissy Pageant! The glamour, the energy, the sheer sissy extravagance!

Sissy, The 2024 Sissy Pageant is Finally HERE!

Sign up today, and join the community that is waiting for you on the Enchantrix Empire. Ask your Mistress for coaching and advice about proper sissy behavior, and then show off that cute ass for us!

You Sissy Pageant Mistress, Harper

xoxo, Harper

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Check out our new social network, Enchantrix Empire.