As you know, I’ve been working on the 2019 Sissy Pageant…

Last night we had our live Awards Show on Cock Radio, and announced all the winners in each category! If you missed it, you should listen and giggle along with us as we go through each category to announce the Sissy Pageant Winners. A special feature for the show was the chance to showcase the entries in the Best Sissy Voice category, between each category announcement.

In the Sissy Pageant, we picked a runner up as well as the category winner.

Everyone who participated honestly deserves a prize, but, well, we’re on a budget here so my admiration for your outfits and panties will have to do. In case you don’t want to listen to the whole show to find out who our Sissy Pageant winners were, I’ll summarize for you, but if you want to remain surprised by the drama, read no further!
Listen to “2019 Sissy Pageant Awards Show” on Spreaker.

Here are the Sissy Pageant Winners!!!

In the Best Sissy Cosplay category, we had two entrants, so everyone’s a winner! While pupslave served us up a perfect closet cosplay rendition of Klaus from Umbrella Academy, newbiegurl88 carried the category with several adorable cosplay outfits, including a Harley Quinn in full sultry slut mode. Best Sissy Evening Gown had a lot of entries, and everyone looked absolutely fantastic! But, the prize had to go to someone, and Dena carried the Runner Up, while Yvonnesofia won handily due to her EXTENSIVE collection of wedding dresses and evening gowns. She could seriously open up her own bridal shop! The sissy pageant winners for Best Cute Sissy were some names that will be familiar by now! They took the charge to enter as many categories as they could, and ran with it! Pupslave was runner up, and newbiegurl88 took home the prize for the Best Cute Sissy!

I’m very pleased to say that my attempts to keep our Best Virtual Sissy category open to as many sissies of every level of experience was successful! The runner up for Best Virtual was Jizzalenebimboslut, while SarinaBarzane, a sissy I actually met IN our Virtual World, took the crown! Way to go virtual sissies!

As for Best Sissy Voice, I want all of you to feel the fire of jealousy, because the contestants brought out their sexy voices and really gave it their all with our scripts! Congratulations go to Runner Up newbiegurl88, and our winner pupslave! I LOVED getting to hear all the entries, and I know for a fact the other Ladies loved them to; I got so many IMs all going crazy over the voice entries!

Of course, the most popular category in the Sissy Pageant was Best Sissy Lingerie. It was seriously difficult to pick the sissy pageant winners in this one, because there were so many lovely looks to choose from! In the end, the winner squeaked by by the strap of a bra; Runner Up went to BritneyAyres, while msnat took home the crown for her fantastic sissy lingerie!

And last, but not least, we have the Best Sissy Overall. Now, to choose this one, instead of voting on who was the best in the land, I let the contestants efforts help tilt the scales. Each entrant’s total number of votes in every category they entered were added together to get a final tally, with everyone all lumped in together. The more categories one entered, the more likely one was to win! Only one contestant entered each and every category, and, as I suspected, that one contestant did indeed become our overall Sissy Pageant Winner. Big congratulations go out to newbiegurl88!!! I think she’ll need to change her username from “newbiegurl” to something more like “badass sissy with sexy panties”! Or maybe just “sissyslutgurl”

Don’t worry, the Sissy Pageant will be back next year!