Dress as a hooker for Halloween

Our favorite holiday is almost upon us! The day where we can dress to the nines in sexy skirts, high heels and stockings without fear that we’ll be outed. That’s right, Halloween is almost here, and crossdressers across the world will be using this as an opportunity to express their femininity to the world in a safe and fun way.

One of my favorite costumes so far has been as a Vegas-themed hooker. I got to wear a sexy outfit and high heels to a friend’s party. I thoroughly enjoyed myself, and I must have done a good job dressing up, because it took them a while to recognize me. Later on in the evening I got a few questions about who had done my makeup. This was followed by them hastily covering a look of surprise when I mentioned that the work of over-done lady of the night art was all my own. Surprisingly, I enjoyed the sense of near discovery as well.

Have you picked out your Crossdresser Halloween Costume?

If not, what are you waiting for? There are an abundance of costumes to choose from, such as this sexy pirate costume, and thanks to McDonalds it’s easier than ever to find a plus sized woman’s costume that will fit you. Most of the online stores offer easy refunds so if you;’re a bit shy still you don’t need to walk into a store and buy a woman’s costume.

Many of you are veteran’s, and have used many a halloween for transgender revelry. For those who are still new at this, I’ve got a few tips on how to make the most of your halloween holiday:

Crossdressing Halloween Tips

  • Use the opportunity to get into character and practice your feminine movement and speaking. Everyone will laugh, and you’ll get a chance to be a lady in front of other people.
  • Your makeup doesn’t need to be perfect. In fact, the better it is, the more chance there is that someone will suspect something. Not that you shouldn’t do your best, just don’t be stressed if your lip liner isn’t 100% perfect.
  • If it’s your first time and you’re nervous about being outed, wear a woman’s costume. It’s a lot easier to pretend you do this once a year if you’re not wearing your best clothes and jewelry.
  • Go with a friend and make a theme of it. It’s a lot of fun if both you and your wife or girlfriend are crossdressing.
  • Have fun! It’ll be hard to relax, with the adrenaline running through your body. Use it to enjoy the evening – be outgoing and get involved.

Let me know, I’d love to hear your stories about crossdressing at halloween. What outfit did you wear? Did anyone guess that you dressed up more often than once a year?


P.S. For the rest of the year, dress yourself in the latest fashion. Save time and money by buying wholesale clothing online!

EnFemme

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Eve
Eve
14 years ago

I’m gonna go as Megan Fox this Halloween (of 2010)

Darkhorse
Darkhorse
13 years ago

I dressed up as the Evil Queen last halloween. I had lost a bet and my female friend wanted me to cross dress. I went all out with a Gothic Theme. My Evil Queen costume was a combination of Black and Gold. I also wore a wig similar to Marie Antionette. I wore black shoulder length gloves. I used a big petticoat to make the gown stand out. I decided to wear stiletto boots to allow the costume to rise above the ground(was tough strutting around with them.) The makeup was fun too. I applied white pancake makeup, with purple… Read more »

Elly
Elly
13 years ago
Reply to  Darkhorse

Did you lose the bet on purpose? I know I might have.

darkhorse
darkhorse
13 years ago
Reply to  Elly

My friend picked out the costume and did the makeup. The bet was an open one where we both agreed to go along with whatever the other person requested . It involved tennis matches – (my friend lost her part of the bet as well.) It acually took place several months before halloween. I had forgotten all about it. She just asked me to accompany her to a party and to meet at her place. I didn't suspect anything because it was still two weeks before halloween. She asked that I come over a few hours before..I wasn't sure why,… Read more »

Cheryl Frederick
Cheryl Frederick
13 years ago

my sisters husband wears some of the clothes she buys for him. she buys them and he models them for her. however, his sons think its creepy.

Vanessa Law
Vanessa Law
13 years ago

I can imagine how not everyone is as accepting – it can take a while to get used to. Time and openness are good partners on the journey. Hugs, Vanessa

Norma Dolan
Norma Dolan
13 years ago

She is a good wife. I wish I could find the same.

Racquel_Lynn
Racquel_Lynn
13 years ago

Halloween is definitely the best time for new crossdressers to test the waters of going out in public dressed. I had dressed female a few times in my life for Halloween, although early on it was more other people throwing things together on me to make me look more comical than convincing as a female. When I was a little older I had some girlfriends that had fixed me up really nice on Halloween and made me look much better and did good make-up and clothes that looked right and did not make me look like it was all for… Read more »

mike
mike
13 years ago

i would love to dress for halloween if only i could get my wife to go along with it.anyone have any advise

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Tina
13 years ago

I always try wear something something with long sleeve It kind of hide my biceps

dave
dave
13 years ago

im going as a witch this halloween, using pink and black sexy costume as my theme. I have bought everything from thigh high boots, fishnet tights and gloves, false eyelashes and a wig. My girlfriend had the mad idea that i should do it. I want to make this the best costme ever and go all out but my girlfriend thinks im going over the top lol! i Have platform thigh high boots that look soo sexy, i look so different when i tried it on. Im so nervous but i know its going to be fun!

Stephanie
Stephanie
13 years ago
Reply to  dave

Enjoy yourself dave I am sure you will look gorgeous I am so jealous lol

Norma Dolan
Norma Dolan
13 years ago

Enjoy your day.

Monica
Monica
11 years ago

I am going as Elvira this year, I have the dress,and wig, I just need the perfect full and large, breast plate, I found them once before and can not find them anymore, and I want the good ones, not the cheapie ones, anyone know where to get them??? Hope to see you there, Monica.

Danielle(Dani)
Lady
Member
7 years ago

I know this is an old one but I saw it and felt I had to add to it although I may go into this story more at another time. 2012 my buddy and I were back in college at a big football (American football for the international crowd) school. In fact, if you watch college football in the US and you aren’t a fan of my school then you hate my coach, that ought to be a big hint. Anyway, we decided to go as “authentic" cheerleaders from our rival college. I pulled up some pictures from the internet… Read more »

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