You can almost feel the anticipation. It comes but once a year. It’s the time when crossdressers can express their true selves without fear of ridicule. So it’s time to glam up!
Last year at Halloween time I wrote a post describing some of the many crossdresser halloween costumes that men can choose from during this season. I thought this year I’d share some more of my favorite costumes and inspire you to take a bold step out crossdressed this year!

Crossdress as Marilyn Monroe this Halloween
Who doesn’t want to look as glamorous as Marilyn Monroe in her heyday? When you crossdress as Marilyn you’ll get to dress to the nines and show off your flirty side. As an added bonus, you can coordinate this costume with your loved one, who has the choice of many public figures who had steamy relationships with Marilyn.

Cross dress as a naughty school girl this Halloween!
After years of trying to convince my wife to go as a sexy school girl, I figure that perhaps she wants me to lead by example
If you decide to crossdress as a schoolgirl this Halloween, be warned. This costume will require a feminine physique to pull off well. If you’re looking for a school girl costume a bit more forgiving of the male figure, try this still sexy yet less revealing schoolgirl costume.
Halloween Crossdressing Advice
A few things to keep in mind when you’re out crossdressed this Halloween. The most important thing is to have fun! Don’t worry what people will think, everyone is dressed up. Don’t worry about being too feminine – you can just say you’re getting into character. If you’ve nervous of revealing your secret, don’t dress in everyday woman’s clothes! The more backstory you can provide about your costume, the safer you’ll be. Having to explain why you just happen to have the perfect matching blouse and skirt could be…interesting.
Trick or treat!



Vanessa is a happily married 30 year old transgendered woman from Seattle. It's been a long road to acceptance for her, despite the fact that she has been crossdressing for more than 25 years. Sometimes, when she looks in the mirror she longs to see the girl that lives
within her.