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…)

Stepping Out Secrets

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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Lynn Jones

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. 🙂

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Zosimus the Heathen

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… Read more »

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Zosimus the Heathen

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.

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maria

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… Read more »

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Kim

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… Read more »

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jeanie

it was a big success and my wife loved it to

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Brandy

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

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Steven

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?

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