You’re a sissy but you can’t go out dressed like a woman every day. Aren’t you lucky that one day a year, people get to dress up as whatever they want. And everyone thinks it’s just a fun costume. You’ve probably never worn any of your girly clothes outside the house before, right? Well what better opportunity than Halloween. On Halloween you can be anything or anyone, including a hooker, LOL! That’s right, you’re not just going to be a sissy, you’re going to be a sissy hooker.
I want you to get dressed up soooo slutty. I’m talking slutty high heels, stockings, a Short mini skirt, a wig, makeup. You should look like a street walking hooker, lol. I want you to be as trampy as you can get away with publicly. Lots of women like to express their more sexual side on Halloween so you should be able to be just as much of a slut. I want you to make sure you have plenty of time to make yourself look perfect before you walk out that door. I know the thought is exciting you. It’s something you’ve always wanted to do. And it’s totally socially acceptable to do.
And no one will know that deep down inside you really are that slutty sissy. We both know that you are that slutty sissy all of the time but you just can’t show it except for one day of the year. Isn’t it going to be so much fun to dress up and go out in public? I’ll bet you’re so excited to show off your sluttiest outfit and your highest heels! LOL! I want you to impress me, I don’t want you to look like a man in a dress, I want men to have to do a double take when they look at you! I want men lusting after you, LOL!
This is going to be your sissy debut! Aren’t you excited? Maybe you’ll even get lucky and some drunk guy will think you’re a girl and he’ll let you suck his cock, LOL! Or maybe he’ll know and he just won’t care because you look so fucking slutty and hot! You’re going to have so much fun being the sluttiest sissy hooker on the street.