Sissy of the Year 2023

Jess Long Bio

Dear Mistresses at the sissy manor,

I’m sissy Jess and I would love to be sissy of the year 2022. I am 23 and my main goal is to be a full time sissy maid for a Mistress or Master. I absolutely adore all things pink as all sissy’s should and If I’m buying anything normal like shower gel or air freshener I make sure to get the pink version. I’ve always been obsessed with wearing pretty dresses since I was forced to wear a pink flower girl dress and get made up by my aunties when I was about 6.

Since then I have taken any opportunity I can to dress up and slowly my wardrobe has doubled in size with all my pretty dresses. I keep my toenails painted pink 24/7 and also I’m in permanent chastity wearing my pink nub chastity cage that can only fit on the smallest sissy clittys. I love permanent exposure too and often go out for walks while dressed up.

When I am allowed to milk my clitty, long gone are the days of shame and purging and instead I lick up my mess and love the humiliation. I am owned by a daddy and love spending time with him and completing tasks for him. As all sissy’s should I have lots of toys that I love to use to stretch out my sissy pussy especially my huge plug that a few years ago I couldn’t have dreamed of fitting it in. I am constantly finding ways to add more pink to my outfits and make them even more humiliating.

Winning the sissy of the year contest would be a dream come true for a pink sissy princess like me.