This post is not for you brave souls that get all dressed up and go to bars, clubs, parties, and maybe grocery shopping. This is for the secret sissies. The shy boys. The ones that say: “If only I was brave enough.”
I want you to start thinking about Halloween. Yes, its not for a while, but this is your chance!
On this day only you are given permission by the entire world to dress any way you like. And how is it you like to dress? As a beautiful woman!
So many people I’ve spoken to plan on doing it every year and for one reason or another don’t go through with it.
“But Miss Teresa, my Wife!”
I know honey, I know. But its just this one time right? This is something you want to try just this once (so the story can go). And since its a one time thing you want to do it right.
“What does that mean to me, the shy, secretive sissy Miss Teresa?”
I’m glad you asked. It means that you’re not just going to put on an old dress and a costume store wig, you are going to dress up completely from head to toe.
“OOOOOO-I like that”
PAY ATTENTION WILL YA!
This means shaving. Yes, shaving your face, but while you’re at it you might as well shave your legs. Its fall and no one will see your legs for a long time. And then you might as well shave your chest. And your back, and your arms.
“Shave my arms? Is that really necessary?”
If you want to do this you might as well go all the way. Plus it will help you feel more feminine.
OK, so now you need an outfit. Panties of course. Stockings with or without a garter belt. A bra or corset. A fabulous dress. And high heels.
Another fun part of this wonderful holiday is that you can walk right into any beauty salon and have them do your makeup without being embarrassed. What you want to do is walk in one day a week or so beforehand and tell them that you’re going to dress as a girl this year. You don’t know anything about makeup and its going to be a surprise to your wife/girlfriend/other.
They giggle and tell you how cute that is! You’re standing there in jeans and a sports shirt so they’re having a hard time even believing you, much less expecting you to show up dressed to kill! They say “Sure, we can help you. When would you like to come in?”
BINGO! You’re in! You have a complete outfit picked out, you’ve shaved, and you have an appointment at the beauty salon for a makeover! And the best part? No one will think its strange.
They might be surprised when you strut in that afternoon in your cocktail dress and heels, but its Halloween! Its OK!
“What about my hair Miss Teresa? I don’t have enough hair to style?”
If that’s the case then you simply bring your wig in a shopping bag. They’ll help make sure it fits right and looks great on you.
Now since you’ve gone this far, and are loving every second of it, you might as well get a manicure. And if you were smart enough to get open toe shoes then a pedicure is a must as well.
“But I live alone, and I don’t plan to go out on Halloween.”
You don’t have to. Enjoy the experience of being a gorgeous woman, take some pictures, and go home. You might surprise yourself and decide to stop at just one bar or club. Just because you can.
One last suggestion. Bring along an extra pair of shoes for driving. Driving in heels is an acquired skill, and you don’t want to ruin a perfect night out.