Sissy Training from Ms Cassandra

It’s my favorite holiday… Halloween!

I’ll bet anything it is yours too, gurls. It’s the one time of year when crossdressing, or a guy dressing like a girl won’t draw any extra attention. Take advantage of it and let’s plan this year’s outfit. I won’t make you into a fairy princess this year as I did last. I have something racier in mind, but I will let you choose between several…a cheerleader, a stripper, a 1950’s secretary like in Mad Men, Bettie Page, and lastly, Audrey Hepburn in “Breakfast at Tiffany’s”.

Dressing Like a Girl: The Cheerleader, Stripper, and Bettie Page

A cheerleading outfit can be found at a thrift store, a stripper can be found in a fetish site online, a 50’s secretary and Bettie Page can be found at the Bettie Page store on Hollywood Blvd in Hollywood. See if they have a website, or make a special trip out to shop. In fact, if you shop Hollywood Blvd from Highland to Vine, you will find everything you need for any of these costumes. There are three wig stores to shop in, a costume shop, clothes for strippers, exotic shoes in men’s sizes, absolutely anything and everything you will ever need for Halloween.

I suggest shopping for two of these outfits, or even all of them, just to have them. Try them on with the wigs. Check out our sissy makeup guide for tips on how to apply your lipstick, eye makeup, etc. and get a glamorous look. Enjoy your image in the mirror and take pictures. Send me the pictures so I may critique them, so I may see how good of a look you have achieved! This includes makeup, the glasses for your secretary outfit, the frilly sissy lingerie underneath it all, and your sissy stick taped back and not visible. Along with the pictures sent to me, I would like several paragraphs describing how you feel in each outfit. Now do it, sissy!

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