Crossdresser Halloween Costumes

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 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.

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.

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

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?

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.

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

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.

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.

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.