By The Loudest Applause, The Winner Is......

[Princess Chantal]

Have you entered a Halloween costume contest while wearing a female themed costume?
If so, did you win a prize for your effort?

Got any sure-winner costume ideas that you are going to wear or some of us could try to put together?

I was able to manage a winner both times that I tried. The first winning costume was a sexy witch that I wore to a "straight" bar for their Halloween Karaoke night. They had one prize for each gender. My friends were telling me to go up during the woman competition, but I just shook them off and waited for the announcement of the male competition to strut my stuff. I guess I shocked the crowd enough to get the loudest applause. (unfortunately I have only a picture of the outfit from that year's Masquerade October meeting to show you)
The second winning costume was dressing up as a southern belle Miss Piggy a couple of years later at my favourite LGBT* night club's Halloween Night Party. The LGBT* community sure has creative minds when it comes to costumes, keep this in mind if you're planning to hit the LGBT* clubs. (I was and am still proud of that costume).

[Stephanie Miller]

I don't go to enter contests. Never feel I have what it takes, I guess. There are so many beautiful ladies, cd & GG alike, that could kick my butt.
Just once a couple of years ago I did win because someone threw my name in without me knowing. I have to admit it was an ego booster.
Here's a copy of the page from the next month newsletter I keep as a memory.

[Beverley Sims]

I was encouraged on more than one occasion to enter as a female.
What an ego boost it is to win not once but twice.
To prevent getting sprung we left the venues soon afterward.
The time I came third I came out and that was a terrific night.

[Chickhe]

One year I dressed up as Sara Palin at a party for the winners of a call in radio contest. It was a real mix of people, it was one costume where I was blending in well, except word got around that I was really a guy and I was called up to the stage for an honorable mention. That was a really fun night, on the way in I was carded and the bouncer could not match my ID to my face and had to ask for assisstance...all the staff came out to see me and they all thought it was a great costume. The original bouncer was blushing when he handed back my ID and said he thought I did a really good job...said I looked really 'nice'.

[I Am Paula]

When I was in my twenties, (long, long ago) I used to go to mainstream bars on halloween. I almost always won something. My personal best- won $300 in one bar, went next door and won $200, and a tray of shooters at a third. One year I even had a challenge, when a customer said I was a GG. The whole bar was flabbergasted when I took out a breast form (birdseed back in those days) and tossed it at him. I'm too old to do that anymore, I may get an honorable mention.

[Cynthia Anne]

It's been twenty plus years since I dressed for halloween! I was thinking of dressing up as a man this year! But then I'd have to spend money on ''man'' clothes! So I'm not sure I want to do that! Sounds sooo boring!

[Michaela42]

A long time ago I went to a local bar dressed as a female. No witch's hats or anything like that. Just a dress and a pair of heels (wig and etc.). For those of you who do not know, I live in a rather small area so I was expecting some huge to do about the 'guy in a dress' . . . so you can imagine my surprise when a lot of people did not even recognize me, let alone realize I was a guy in a dress! I did not enter the contest, but I wound up winning a prize just the same.

[I Am Paula]

Cynthia Anne- I had to go buy some boy stuff (suit, wallet, socks) to attend a funeral recently- sucks doesn't it. I've hidden them in a box in the back of the closet, in case I need them again.

[Barbra P]

Back in the mid-eighties I worked in the data processing department of one of the country’s largest savings & loans. On Halloween the company encouraged wearing costumes to work and the home office, including the DP department, closed at 1:00 for a catered party. I dressed enfemme, heels, wig, makeup, skirt, blouse, etc – and won first place which consisted of dinner for two at a very nice restaurant.

The next year I had people (mostly women) coming to my office asking me to dress again for Halloween. I thought I improved on the costume and I even went and got acrylic nails. The DP department was housed in a separate building from the main offices and the two buildings had separate parties, but I had to attend a meeting in the morning in the main building. Not much got accomplished at the meeting as almost all the people from the main office attending were women. I was bombarded by questions and comments; you walk better in heels than half the women in this building, where did you get your nails done, you have beautiful legs, who did your makeup, can you come to my area when the meeting is over, etc. Well I got paraded all over the main office for about an hour after the meeting.

My boss came to me the next year and said that it was pretty much a tradition now and I had better plan on dressing that year too. She told me that people were wondering how I was going to improve my costume; she didn’t think I could. Well we had learned that my boss was pregnant and I found a brown maternity jumper among some of my wife’s old clothes out in the garage and I looked about eight-months pregnant when I walked into work.

[Alice B]

I;ve posted it before. Entered contest at my professional photo group and won. I was also the guest speaker.

[JamieQ]

Our department is undecided if to costume this halloween or not. The nurses are going to be witches and I am not sure what the nurse aides are going to be. We are sort of an independent department and I would love to go as a witch if they would allow it. I would love to hear coworkers say " I do not think that is the first time for him..." I work for a nursing home and the administrator is a 74yr old woman and she is so conservative about everything. I'll probably just hang around the mall dressed up after college.