Was your Halloween a crossdressing success?

The crossdresser’s favorite holiday has come and gone. Halloween is the one night a year we are able to express our true femininity in public without fear of ridicule, and many crossdressers I know live in expectation of the next crossdressing halloween experience. This year was one of the best Halloween’s yet for us, as my wife and I coordinated costumes and were the crossdressing couple at parties we attended. At one I was her well endowed wench, and another I was her ‘not as chaste as she should be’ nun.

Was this year a crossdressing success?

Halloween is about having a lot of fun with friends, and for crossdressers expressing our hidden side in a safe environment. We got more than a few looks when my wife and I went out after one Halloween party to grab a late night snack – though I’ll keep believing it’s just because there were two gorgeous woman dressed more seductively than usual 🙂

I was pleased that initially our friends didn’t recognize us, and that a few people commented on how good I looked as a girl. Inside I was doing double backflips with joy, but outside I smiled sweetly and thanked them for the compliment (I can’t give away too much all at once…)

Preparing for the evening was a great delight, as my wife and I hunted down the perfect costumes and accessories. Later in the evening I got to do both my makeup and my wife’s and I must say that blue eye shadow looks a lot better on her than it does on me.

Was your halloween a crossdressing success?

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I’d love to know what you dressed up as this Halloween – comment and let me know!
If you missed out this year, not to worry, there’s only 357 days until next Halloween 🙂

Get ready for next Halloween by following the sage advise in the ultimate crossdressing guide.

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
  1. Lynn Jones 11 years ago

    I’m a bit 50/50 over dressing up at Halloween. I guess it depends on what your motives are! If it’s for a laugh, then you’re probably going to be okay… course, some people want dress up and look presentable rather than humerous. I think at that point, alarm bells may start ringing if you’re not out. 🙂

  2. Vanessa Law 11 years ago

    Too true! I once did my makeup a bit too well, and I found out that there was some, uhh, discussion among the women about it 🙂

  3. Zosimus the Heathen 11 years ago

    Well, Halloween’s not that big a thing down here in Oz (although it has become quite common to see at least the odd roving band of trick-or-treaters on the night), but I did recently get an excuse to indulge in some CDing (sort of) under the guise of fancy dress, thanks to a rather important event on our own calendar – the Melbourne Cup. This horse race (dubbed “the race that stops the nation”) happens on the first Tuesday of every November, and it’s quite common for workplaces here to have Cup functions on the day. My own (an old folks’ home) was no exception, and although I wasn’t rostered on that day, I decided to go anyway, mainly because I heard there were going to be prizes given for, among other things, “best fancy dress” (it’s quite common for people who attend the actual horse race to go in fancy dress). My first thought was to go in drag (and I certainly had no shortage of classy things to wear in this department), but unfortunately I chickened out at the last minute, and went as something much more safe and conservative instead: a fairy!

    My fairy costume was something I’d actually had for years (I used to wear it to raves a lot, where it went down a treat), and consisted of a longish silver satin skirt (with zigzag hem), a matching sleeveless frilly top, and a little hat covered with green satin leaves. To complement it, I also dolled myself up with makeup, mascara, green eyeshadow and green lipstick, and also took a silver handbag in which to keep my cosmetics and other necessities. To my delight, my costume was a hit – I did indeed get a prize for it, and all the residents of the home loved it (most of the staff thought it was a hoot too). Even better, I had numerous requests from residents for me to pose with them in photos! I also “passed”, at least in some people’s eyes, even though I hadn’t actually aimed to – the beauty of the costume I threw together, I thought, was that even if I didn’t look like a girl in it, I could always say I was aiming for some ultra-sexy, ultra-cool David Bowie-style androgynous look.

  4. Vanessa Law 11 years ago

    Good on you Zosimus! Did any of the residents get suspicious at how good you looked as a women?

  5. Zosimus the Heathen 11 years ago

    Mmm, hard to say. I wouldn’t be surprised if at least some of them wonder about me… People can be quite cluey about these sorts of things.

  6. maria 10 years ago

    Well I went out for the firist time on halloween just dressed in a skirt and blouse and hose I was scared at firist but as the day went on I got very comfortable being out dressed I started by going to CVS there was a young lady working and a young boy the lady was very nice she helped me and never said anything but the boy laugh untill I left but I went on my next stop was Target I was treated great nobody bothered me. My next stop was Kohls were a sales women asked if I needed any help of course I said yes and she helped me find a really nice skirt a alos a new dress she asked me a couple of questions like why I was dressed as a women and I explained that I enjoyed the feeling of the cloths she also asked me if I wanted to be a women for ever and I explained to her the I was married and streight and that my wife don’t know the sales women was great we even went to Dunken donuts for coffee and some more talk.After the coffee she told me to come back again and that I looked really good, from there I went home in a cloud it felt great to finnaly go out and I will do it again.

  7. Kim 10 years ago

    At the office where I work every year there is a halloween costume contest in the day and a party at night. A female co-worker who is about the same build suggested that we pretend to be each other, so we swapped clothes for the day and got wigs, and she helped me with makeup nails and jewelry, I just had to get shoes because my feet were too big! We even swapped name badges, sat at each others desks and made everyone call us by each others names all day! I wore a black suit with a short skirt and pumps with 4″ heels during the day and she wore my suit and tie. For the party we changed so she wore a tuxedo and I was in a sparkly red minidress! It felt great, we got a lot of laughs and we won a prize! Same again next year maybe!

  8. jeanie 9 years ago

    it was a big success and my wife loved it to

  9. Brandy 8 years ago

    Last year we had so much fun on Halloween. I went to a riaque party at a local club and wore a mesh body stocking with thong panty and bra under it and my heels and red wig

  10. Steven 8 years ago

    I’m looking forward to going out on Halloween….but I’m going to step into a businesswoman’s shoes….black pinstriped pantsuit, blouse, open jacket, and business pumps…see how that goes! Any advice for me?

    • Author
      Vanessa Law 8 years ago

      Get dressed a day before Halloween. Practice your look, makeup and walking in heels. Spend some time being ladylike to get into the zone before Halloween. Then you can blow them away on the 31st 🙂

      • Steven 8 years ago

        Hi Vanessa,

        Thanks for your response but I had some follow-up questions…are there any places that can alter women’s suits to fit men? Also, how do you wear the outfit? Is the jacket buttoned or opened, and the blouse tucked in?

      • Author
        Vanessa Law 8 years ago

        A tailor or seamstress should be able to alter suits to fit you, thought be aware they can be expensive, so it’s only really worth doing on nicer clothes. As far as how to wear them – it’s really what looks best on you and your figure. Play with all of them, perhaps even get a girl friend to comment on what she likes. Fashion doesn’t really have any hard and fast rules 🙂

      • Steven 8 years ago

        Hey Vanessa, just wanted to say thanks for all your help! I bought a sharp women’s pantsuit from Nordstrom’s and was able to get a seamstress to alter it, although they are tight-fitting LOL! My suit is black power pinstripe, with a white dress blouse and crisp black pumps to match, as well as a clutch bag. I’m looking forward to stepping into a woman’s shoes for one night and if anyone asks, I’m going to say my body got swapped with a woman’s. I even have the breast forms so I am going all out!

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