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?
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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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Hopefully it will be Alice in Wonderland for me this year.
Nice choice!
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?
Michael
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!!
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… Read more »
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… Read more »
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 🙂 )
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
Thanks hon. Hey, you know, you don’t need to wait for halloween to get your girl on 🙂
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?
Follow along at https://www.crossdresserheaven.com love. We regularly have tips and advice on how to look your feminine best!
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.… Read more »