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!
Halloween is around the corner and I have a closet full of short skirts…HMMM which one do I wear???.This year I wanna go as a “Hooker”Not just a hooker..maybe spice it up and go as A “Lesbian Hooker” I will wear layered shirts with a short denim skirt and wear some black crochet fishnets(very erotic) over some tan or off black pantyhose and add a pair of black 4 1/2″ hi heel boots.I will top it off with a medium length brunette wig and some white framed dark sunglasses and some blue or red lipstick.I may just be the talk of the party.I wear like 3 pairs of tan pantyhose or a few pairs of tights to give my legs a thicker more feminine appearance then add the final color pair over them.
I just love this time of year,
hehe – definitely a great time to let your inner woman out without fear!
Hi , Vanessa! Thx for this wonderful site as ab outlet , this will b ny 3rd post no replies as of yet, but to reply on Halloween dressing as a gurl, I have attempted 3 succesful outings in femme, I’m a very short gurl 5’4 with a gurlish figure, I guess u can say I’m a very passable gurl considering I have been approached by men and women. Thx for your site I will definetly continue replying. I am in femme as we speak, and feel, very feminine at the moment. Any tips on how to encounture others for support and gatherings to interact as a woman, I desperatly await a reply thank you , love , Margaret Stewart.
I’ll have to find the African-american equivalent….Marilyn doesn’t really work for a African-american girl……lol
I picture this may well be numerous upon the written content? in spite of this I still consider that it usually is appropriate for virtually any form of topic subject material, as a result of it could regularly be pleasant to decide a warm and delightful face or possibly pay attention a voice while preliminary landing.