Chi Upsilon Iota Tri-Ess

Halloween at work 2004
A story of my first Halloween en femme

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Every year my company holds a Halloween costume parade and contest for the employees. There are various prizes for team costumes as well as individual costumes. This year they decided to go with the theme of "at the movies" and announced this about a month in advance.

I immediately though it would be a fun way to come to work en femme and maybe even pick up a prize in the process. I discussed it with my wife and we came up with the idea of going as "Dorothy Michaels" (Dustin Hoffman's feminine role in Tootsye). Well, we started to look for a red sequin dress like the poster for the movie and none were to be found. I then realized that that was probably a custom made dress for the movie as it was definitely made for a guy (high neck, long sleeves etc…).

We were not discouraged and decided to go to a big costume shop in town and look for ideas. After rummaging a bit we decided on either Mae West or Marilyn Monroe's famous "7 year Itch" outfit. I got a few different ones and tried them on and se decided Marilyn was the look to go with. We rented the dress and wig and I started to plan the rest of my outfit.

I had started searching the web looking for the classic poses of Marilyn with the dress billowing over the subway grate and was looking for things like makeup, jewelry and shoes she had on so we could make the costume as authentic as possible. One other thing I needed was a strapless bra or more accurately a white bustier type of bra (like for under a backless formal) in a size 42. I had gone to several stores and had no luck and then stopped at David's Bridal. They had one that fit great, but was a bit over budget. I kept them in mind and went to a local thrift store and as luck would have it, there was a 42C bustier type strapless bra for 75 cents! Needless to say it was not there for long. I had to but bra extenders for it to fit better and that was a small concession to make.

A few days later I had been looking for the white sling-back sandals with about a 3 inch heel and had no luck. Of course white sandals in October are doubtful anyway. I finally stopped in a shoe store called "Bakkers Shoes" and they had a pair that were almost a perfect match. They were 3" heel, wide sandal strap and they had ankle straps instead. The best part was they were 5.00 on sale. I now had 2 of the 4 items I needed. I still needed a pair of large round button type earrings in white and a purse to carry my stuff. She did not have a purse in the picture, but it seemed like a good idea.


I could not find the earrings anywhere. Apparently big round button type earrings are not the rage at the moment. I did go online and I found a company which had a pair that were very close, pretty big and well, very pretty. I ordered them and now simply needed a purse. That came after a few more visits to the local thrifts, where I found an off white hand clutch type purse that looked retro in styling (probably was from that era!).


At this point I had no idea how it will all look as I did not have the dress. It was a rental and I was picking it up the night before the costume contest.


I never filled anyone in at work except for 2 ladies I work with about my costume. I did drop a few hints to people that when they saw my costume they'd probably say "Holy smokes!" but that's about all I said. Finally the day to pick the costume up arrived and I went out at lunch and picked it up. I brought it to my dressing room (I have a rented office space I use for my dressing room) and tried the dress and wig on. I got worried because the wig was shorter than my own hair and because it was blonde and my hair is brown, I had problems. I decided to stop back at the costume shop and see what to do. I wound up buying a "bald cap" and the latex and glue to use if I needed to hide my hair. In reading the directions for the cap, I realized I could simply use "a thousand" bobby pins and stuff my hair under the wig, so. that's what I wound up doing.


The next morning I left early and went to the dressing room to start changing. The hair and wig took the longest time of all. I had stuffed it all up and took pictures of the front, side and back to make sure nothing looked bad. Once I was satisfied with the look, I put on the corset (a bit more snug than usual) and over that I wore the white strapless bustier. It fit wonderfully over the corset. I put on the leotard that came with the dress and then the dress, other accessories to create the look and finally the shoes.

The look was coming together pretty good I thought and I sat down and spent time doing the makeup as well as I could. I did not want make if overly dramatic as Marilyn's pictures were not like that from what I had seen. She had vivid lips and that was about it. I used subdued eye shadow and blush with deeper red lipstick than normal. I had also painted my toe nails the night before and I use long glue on nails in the same shade for my fingers. It was now time to face the music. I took one more look in the mirror and liked what I saw.

I headed off to work and arrived before most people had. I sat down and did my usual morning routine and eventually head a few co-workers. I poked my head out of my cubical and said "hi!" I got a "Holy Smokes" from more than one person who just though it was wild. Within ½ an hour I had a steady stream of people stopping by to "see Marilyn." The women all seemed to love it and the guys were just confused. Of course I work in an office of mostly men (computer software company). A few ladies had noticed the small details like my toes were painted in the same shade as my fingernails and such. I smiled and said, well if you are going to wear sandals, it makes sense to make your toes match your fingers right? Little hints that I had done this more than once were dropped all over the place and I suspect a few people picked them up. More than one person noticed (and commented) how well I walked in the shoes. I simply told them I had practiced, which was true! I also found it was very difficult to type with the length of nails I had worn. They were really long, but I had done that for the effect more than the practicality of it.


Finally the time for the contest had arrived. I wandered over to the next building (we have 4) and met up with the other contestants. Since the theme was movies, various groups of people had dressed as entire films. We had "The Wizzard of Oz", "Monty Python's Search for the Holy Grail" and "Ghost Busters" among others. I was the only person not in a group theme. The parade finally started and wrapped around the building to the judging area.


I joined the parade and eventually made it to the judge's stand. Of course, the Marilyn pose this was based off had her holding down her billowing dress because of that updraft. Many people (guys and gals) kept teasing that I needed a fan for the dress. I laughed and said "trust me you don't want to go there." Little did they realize it was because I did not want to show my Veronica 2 hips, because the illusion would have been lessened. I was asked by the judges if I had shaved my legs (I thought it was apparent!) and I said, yes as well as my underarms and held up my arms. They seemed to like that and someone took a picture (I never did see that one). I had a few other comments on the shoes by women who said they never wear them that high and such. I just enjoyed all the attention.

By now it was lunchtime and I called my wife and asked if she wanted to go to lunch. Of course she knew I was still in costume and to my delight she said sure. We went to a small restaurant near by and enjoyed lunch. Of course there were a few funny looks, but by now I was used to that. I did have to stop at the local grocery store for candy to distribute for the afternoon Children's time, where we can bring our kids to work and they get to wander the rows looking for treats. In the store the cashier loved the dress and complimented me on it.

I headed back to work and finished up the day as Marilyn. About mid afternoon I learned that I had won 2nd prize in the "other" category, which was great. It was not a lot of money, but I won something and had a blast doing it.