Isn’t it lovely here at Princess Andi’s blog? The pink, the entire page of sexy pictures! It’s fantastic here. I’m so glad she invited me over to do a guest post! Who am I? Well, my name is Empress Stephanie, but you can call me Ms. Stephanie. You can find out more about me here, including my top ten favorite kinks. Go check it out when you are done here.

‘Tis the Season for Being a Sissy

Today I want to talk about one of my favorite seasons for sissys. Not Fall, or Autumn, but the Halloween season. Why you ask? Well, because you can walk into any store with your head held high and buy clothing in your size. You can even ask a clerk for help. It’s all about confidence here folks! Believe in your heart that people will believe you are dressing up as a woman for a Halloween party, and you can get all the help and advice you may need. 

Translating Sizes

If you really don’t want to have to ask a clerk for help, there are plenty of places on Google that will help you translate your male sizes into the female sizes your sissy heart desires. It’s just a matter of patience. If you are having trouble, a quick Skype chat with me may help you find what you need.

Creating Your Ideal Look

So, what’s it going to be, sissy? French sissy maid? Bimbo? Classy lady? Even cheap and slutty is possible this time of year! It’s all a matter of personal taste. If you do, in fact, have a Halloween party you want to dress up for, don’t forget to grab a decent wig! You don’t have to go high dollar, but cheap wigs just look wrong. Find a medium price point and pick one out. I suggest close to your natural hair color, but if you want to be a platinum blonde bimbo sissy then go for it!

Make-up for that Sissy Face

Make-up can be fun too. If you don’t have a clue about putting on make-up, go to a store like Sephora and ask them to help you. Often they can do a simple make-over right there in the store. Let them know you aren’t in the market for *everything*, just the basics. Get them, and then go home and practice replicating what she did so you are confident in your skills before the party.

Finding the Fun

If you haven’t been invited to a dress-up Halloween party, try looking at local adult establishments that may be having a party, with prizes for “best dressed” and such. Go there! Be anonymous! You’ll have a blast being out in public dressed up as the sissy you’ve always dreamed you can be. You may even meet a handsome gentleman or two, and the two of you can flirt and tease and get up to all kinds of shenanigans!

Stepping Out in Sissy Style

One last word before I leave you with Princess Andi. Unless you are used to walking in heels, do not get 6-inch heels for your first foray out into the world of realistic sissyness. Get yourself a pair of kitten heels, or ballerina flats.  If it fits with your look a low-heeled MaryJane would work too. There’s just not enough time to be fully confident in a pair of stripper heels! 

If you need help with any of your transformation preparation give me a call! I’ll help you in whatever way I can to become the best sissy you can be Halloween or year-round!

Talk to you soon-

P.S. Don’t forget that we at LDW are celebrating Cocktober with old-fashioned prices during cocktail hour!