Was Your Halloween A Crossdressing Success?

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. 🙂

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 🙂

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.

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

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.

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.
Thanks
Maria

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!

it was a big success and my wife loved it to

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

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?