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!

En Femme Style

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Ronda Macon
Ronda Macon
5 years ago

I love wearing sluty costume around the house on sat

Dawn Judson
Active Member
5 years ago

I dressed as a St. Pauli girl, last year. I’ll be attending the same party with the same people, this year. I really wanted to wear a female superhero costume, this year, but to avoid suspicion, I need to go with a manly costume. I just haven’t figured out what that will be yet.

Jennifer Love
5 years ago

I am doing my annual gay bar party. No worries about being outed there. This year I will be Princess Peach, I got the dress on amazon and picked up a few other things such as a darling pair of red heels. Last year I went as a French maid. That was a lot of fun. When I sat on the bar stool my petticoats wouldn’t go under me, so it on to my ruffled panties. I do it every year and try to make New Years too.

Luna Wing
4 years ago

I want to dress as a female Pokémon trainer but I don’t want my parents finding out

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