My first idea is mainly for people that work in an office. A lot of places are going to have a Halloween party on the Friday before and will encourage their employees to dress up. Depending on where you work, it may be a simple “Wear a funny hat” type of day or a “Come in Costume” thing. We’re shooting for the latter.
Here’s the plan. You begin telling your friends that it sounds great and you’ll definitely come in costume. At first you say you have no idea what to wear, but of course you do don’t you?
As time goes by try to casually mention to someone, preferably a female friend on the job, that one of these days you’d like to dress as a girl, just for the hell of it.
She’ll probably laugh and think you’re joking. If she shows more of an interest just play it slow.
You say you’d like to come in dressed as one of the secretaries. You really appreciate how great they look every single day, and it must be hard for them. (it is)
Unless she offers to lend you one of her outfits and help with your makeup, you let the whole thing go for a while.
Tell a few more people and gauge their reaction. They have no idea that when you do get dressed up its going to be a complete transformation!
You’ll shave your legs, wear the prettiest lingerie, a fantastic dress, a cute wig, heels, makeup, jewelery and perfume. You’re going to blow them all away and love every second of it!
If you plan to come in that morning and spend the entire day dressed like this, bring a purse and a bag with the essentials. Extra panties and stockings, makeup, and maybe even a second outfit if its going to go on into the night. With a little luck the girls might even take you to a local bar for a drink. Won’t that be great!
You’re gonna be just another one of the girls and I’m sure you’ll get a raise one way or another!