Crossdresser Halloween Costumes

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!

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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  1. Fluffy 8 years ago

    Hopefully it will be Alice in Wonderland for me this year.

  2. Profile photo of Vanessa Law
    Vanessa Law 8 years ago

    Nice choice!

  3. Michael 8 years ago

    My ultimate fantasy Halloween costume would
    be a custom-made,near perfect replica of a
    Dallas Cowboys Cheerleaders uniform,the blouse,vest&shorts/w pantyhose&white boots?

  4. Tony/Toni 8 years ago

    Wife and I went in “Different roles” this year. She did me up super hot and sexy, full make up, nails, and wig…I was her slut and she was my pimp! One guy at the party even offered her money to have me blow him in his car…she said NO…I told him I would later…and I did!!

  5. Millie 8 years ago

    Great topic. I wore a bridesmaid’s dress to a Halloween party a few years ago. I had never worn women’s clothes in public, but I was determined to do it. I got the dress for $10 at Goodwill. I wore some of my favorite satin lingerie underneath, along with makeup, wig, perfume, stockings, heels, even nail polish. I didn’t do ANYTHING to suggest I was just doing it as a joke, other than to wear a little button that said “Always the bridesmaid, never the bride.”

    It was like I had died and gone to heaven. I was there with some of my best friends, but none of them thought a thing about it. Both girls and guys told me I was beautiful. A really pretty girl said, “No, really, you look GORGEOUS” and seemed to be turned on. And one guy in particular was clearly hitting on me and appeared to have a hard-on. If I hadn’t been happily married, and accompanied by my sweet wife, my life might have gone a different direction that night!

    I definitely want to do it again some time.

  6. kandi 8 years ago

    I pulled out all of the stops this year for Halloween! I started in July buying thigh-high boots with 5.5″ heels. I bought several witch outfits online. I decided on the black witch with 3/4 sleeves and short skirt. It would go great with the boots. I found the rest I needed including a full mask with painted-on makeup. The wig went over the mask and hid the strap. Confident on the outcome I rented a car and drove over 100 miles to another town.
    I booked a hotel room to shower and dress up. My heart was pounding when I walked out the hotel room and heard the door slam shut behind me.
    I walked to the rental car, keys in hand ready to start my night out. It was slow walking in those heels! I shopped in the Mall and drove around the town.
    I ran into trouble getting lost and going thru a toll booth. I just paid it and drove off. I looked for a party and parked nearby one. I walked over but it wasn’t well attended. I drove some more and stopped for some window shopping, waving at the security guard. Wonder what he was thinking? I stopped along the way to fill the rental car with gas. I took the precautions a gal should take by locking the car door, taking my purse with me and watching around me. I paid at the pump, unlocked the door and drove off. When I returned to my hotel room, I changed into a special nightie, thinking how far I had gone.

  7. Profile photo of Vanessa Law
    Vanessa Law 8 years ago

    You go girl! Way to keep Halloween fresh and exciting!

    Zosmius, my French isn’t too good, but I got that you wore a bride’s dress? That’s on my list for sometime in the future (though having a wedding ceremony wearing a brides dress is the scenario I pictured 🙂 )

  8. Bob 7 years ago

    Brilliant site… great to read about everyones experiences! Great to see others with fellings like mine.

    Only regret is we dont have Halloween in Aust!

    Cheers & be happy

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Thanks hon. Hey, you know, you don’t need to wait for halloween to get your girl on 🙂

  9. Dylan/Dyan 7 years ago

    I am a boy who is going to dress like a girl for halloween. can someone give me tips on how to look like a girl?

  10. Donna 7 years ago

    My best CD story is when I was only 14, I dressed as a vampire girl with a great store bought costume, shorth ruffled skirt, black hose, stacked heels. My buds and I were doing it as a joke. It was no joke for me as I had been dressing forever. I went out to wait for my ride and ended up at another party all together. One of the greatest nights of my life, the whole party thought I was just a regular teenage girl. I had some time dancing with a boy and got a good night kiss. I am 42 now and look back on this as one of the best nights of my life.

  11. Eve 7 years ago

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

  12. Darkhorse 6 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 eyeshadow with thick black eyeliner. I wore false eye lashes with lots of mascara. The blush was bright red and so was my lipstick. I also wore a dark black body stocking underneath my costume.
    I was very nervous going out in public dressed up like this, but soon realized that many other also cross dressed. I had a blast that evening. Most of my friends didn't recognize me because of the makeup and the costume. I am thinking of becoming the evil queen again this halloween.

    • Elly 6 years ago

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

      • darkhorse 6 years ago

        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, but I obliged. It was only when I arrived that she revealed what she wanted me to do. I was in shock at first, but decided to be a good sport.

  13. Cheryl Frederick 6 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.

    • Norma Dolan 6 years ago

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

    • Vanessa Law 6 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

  14. Racquel_Lynn 6 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 a joke, although those friends at that time did not know I had the desire to dress like a female all the time because I was not out and open about it at that time and was actually still repressing those feelings and in denial to a certain degree to myself as well, but I knew deep down that this is what I wanted.
    On my second date with my ex-wife (but before coming out to her) we were on our way to a Halloween event and I Was scrambling to put a costume together. We stopped in a Walgreens to see what costumes and accessories they had. She had some clothes in her car and I asked her if she thought she may have a skirt and a feminine top that may fit me and if I could borrow them and she said sure, so I bought some black fishnets and the playboy bunny ears and tail, put those on with a black skirt and a white off the shoulder top that she let me borrow and just did the best I could on short notice. I won 3rd place in the costume contest that night and I didn't even have on any make-up other than eyeliner.
    I did come out to her before we got married and told her I wanted to become a woman and she was awesome about it.
    A couple of years later, I decided to go out as a female for halloween again. I was working 2 jobs that day, and they were both having costume contests. My ex was a model and she helped me so much with teaching me how to put on make-up and so many other things. She fixed me up really good. I went in to my first job and was amazed that people I worked with every day were not recognizing me….until I spoke. lol I turned some heads and one girl I worked with told me that her boyfriend and one of his friends were there talking to her and saw me walking past and she said they were drooling an her bf said "wow some long @$$ legs on that b!t@#. " lol We had a lot of great laughs over that! I won the costume contest at that job and then went in to my second job and won that one too. A bunch of us from my second job went out to eat and then to a couple of clubs that night and I had so much fun and my wife (ex-wife now) who already supported me completely, told me that if she wasn't already convinced that I needed to be a woman before, that night would have done it. She saw how happy I was and how much fun I had.
    A few months later, I entered a "Dude Looks Like A Lady" contest and won that. I got to go backstage to meet Aerosmith at a concert in Lexington, KY. I did not go to the concert dressed up, but now I wish I would have, but I did have the band sign a picture of me dressed up for the contest.
    After that, I started going out in public more as Racquel.
    Halloween is a great springboard for crossdressers, but as good and free as you feel on Halloween, it does not compare to the feeling of freedom (and fear) when you go out crossdressed on any other random day of the year.

  15. mike 6 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

  16. Tina 6 years ago

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

  17. dave 6 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 6 years ago

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

  18. Norma Dolan 6 years ago

    Enjoy your day.

  19. Monica 4 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.

  20. Profile photo of Danielle(Dani)
    Danielle(Dani) 5 months 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 and then went shopping with my mom. We bought some fabric in the right colors, bought some shirts to cut up and use as a start. My mom(even though it she was sickened by the idea of me CD’ind, I don’t think she saw this as that) made the costumes. We had halter type tops and fitted skirts. Our accessories included correct wrist bands and temporary cheek tattoos. We had white tennis shoes and short white socks like cheerleaders would have. We bought blond wigs and had a girlfriend of ours pull them back in a cute manner that left them long but looked like a cheerleader.

    Here’s what I felt was the best part was. We made bloomers with the school’s name in rhinestones on our rear ends so when we lifted our skirts we were showing the school spirit of our rival.

    This was enough for me, but for some reason my buddy suggested at the last moment that we wear mascara. I don’t know why, I don’t think he’s a CD. So the girl that did our hair gave us hers(not that I didn’t have my own at home). I acted like I wouldn’t be any good with it and let her do it. Good excuse to get pampered little anyway.

    You have to imagine that at the time we were both two big ole hairy individuals. Our goal, again, was to be authentic cheerleaders from our rival school which of course our rival school would only have ugly cheerleaders. So we also had full beards grown at the time. We weren’t sure how the general public in this college town would react because some people call it the greatest rivalry in sports(I know
    I just hurt some feelings) but a lot of people fully recognize it as one of if the not the greatest rivalry in college sports. We weren’t sure if we’d get full on assaulted with beer bottles as we walked down the street.

    The truth is that it was a blast. I bet we had over 200 people come up and take pictures of us and with us. We’d have someone posing with us and their friends taking a picture from one side and people would be standing behind us or on the other sides taking pictures too. We entered a costume contest where we didn’t do so well. We made it to the second round where we showed our bedazzled rear ends with the school name on it and go booed pretty loudly. That didn’t matter. It was still a good time.

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