Working Woman Meg

You remember Meg of Call Me Meg fame. Six years ago, she went to work as a woman on Halloween and she generously gave me permission to repeat her wonderful story, so here it is. Enjoy and be inspired!

Setting the Trap

My old manager, N, was a nice woman and a good manager. She worked with the team members to ensure that we weren't travelling too much, that we had the resources to do out jobs, and that everything was going smoothly. I enjoyed working for her.

One day we were discussing an upcoming job. She had already booked her travel but another obligation came up and she couldn't make it. Since it was to be my project, I was asked to go in her place. Then she said something that was straight out of chapter one of many TV fiction stories:

"It would be great if you could use my ticket. It's too bad you're not a girl."

I said, "I could be." She asked what I meant and I said I could "dress up" and maybe get away with it. She laughed and asked for proof. We went on to other issues about the upcoming trip.

I went home and printed "proof." I found a not-bad picture of Meg and printed it out and brought it to the office a couple of days later.

It was probably a week after that that I finally found N alone in her office. I asked if she had a minute and I reminded her of our earlier discussion. She grinned and said "yeah...?" and I pulled out the picture.

She said "no way" and insisted it was my sister. I told her I have a sister, but that's not her. She kept looking between the picture and me and finally acknowledged that maybe I was telling the truth. Then she asked "was this for a costume party, or is it something you do, sometimes?"

At the time, I was pretty deeply in the closet and my first impulse was to take her "costume party" line and run with it. My brain was screaming "ABORT! BAIL OUT!" but I also thought she phrased what I do perfectly. I said "it's something I do, sometimes."

She said I had to come into the office like that. I suggested Halloween, still a few months off. She insisted I do so. We agreed I would come in on Halloween wearing women's clothing.

We had little joking passing discussions about this in the following weeks. I reminded her I was going to wear women's clothing on Halloween (actually, the day before Halloween ~ Oct 31 was a Saturday).

I, of course, wasn't joking.

Male to Female

In preparation for Halloween, I went to a few nearby salons, trying to line up someone to do my makeup.

You all know how I plan and replan and overplan. I had done my own makeup a few times by then, and I was comfortable with the results, but I wanted to have someone else do my makeup. I had three reasons:

• Mistakes were less likely
• It would take less time
• I had cover. I wasn't ready to admit to the office that I dressed at that time. If people commented on my makeup I could honestly say "I had a pro do it."

So, as I said, I went to a few nearby salons, trying to line up someone to do my makeup. There weren't many. Most opened too late to be useful. One sounded hopeful but after speaking to her once, the makeup lady stopped being available. I understand. We can be a little much for some people. I don't push myself at anyone.

By the way, there was no scheduled Halloween events at the office. Other than a silly hat or two, I'd be the only "costume."

I figured there were still two options.

Before the big day, I packed my clothes, shoes, wig, jewelry, and makeup into a small overnight bag and headed to the office.

There are two malls near my office. I planned to change at the closer, more upscale one. I didn't expect them to open as early as I wanted to get to the office so I just brought my bag in the car and went to work.

A little while later, N came in. She said "I thought you were going to dress as a woman!" I corrected her ~ I said I'd wear women's clothing and I was wearing women's jeans, socks, a polo, sneakers. I told her she'd have to take my word for it on panties. (I use that line a lot and everyone agrees to take my word. :) ) She agreed to do that as well, but she also (rightfully) accused me of chickening out. I told her I'd go change at 10 and be back at 11. She was good with this. I also wanted to make sure that she'd be in the office then ~ I wanted cover in case I came in and she decided to take the day off, or be on travel. N was not the best at letting the team know her plans.

Just before 10, I went to the mall. I took my bag with me and considered my two options.

One was to have someone at the mall do my makeover. I walked through Macy's, and there was also a Nieman and another upper-scale store. I planned to check them all out, but I wasn't crazy about the department store option. Then I walked past the M•A•C store. There were a couple of women working there and one customer. I walked up to one of the women and she asked if she could help me. I explained that I'm going to be dressed in drag and would like to know if someone in the store could do my makeup. Once I convinced her I was serious, she wanted to know when. I pointed to my bag and said I could change in about ten or fifteen minutes and come back. She said that would be OK. I said I may put on foundation and lipstick just so I don't stand out too much. She said that was fine too, or she could do it all. I asked her to please wait for me ~ I am serious and I will be returning very soon. She promised she'd be available.

Meg at M•A•C

I went down the mall to the family restroom. I had shaved as close as I could before leaving the house, and I made sure my arms, legs, and chest were clean as well. I quickly removed my "male" clothes and put on my bra, pads, hose, camisole, half-slip, and heels. I put on my wig and then realized I did not bring my favorite, but it wasn't a showstopper. It was good enough. I made a mental note to label the bags with my wigs ~ 1, 2, 3, and 4 ~ for my favorite down to the one I'd wear if 1, 2, and 3 were unavailable. This was number 3.

I put on sunglasses and looked critically in the mirror.

Woman from the neck down, with a man's face. I removed the dress and put on my liquid foundation.  I put on a coat of lipstick and my (women's, of course) sunglasses. It wasn't great, but it was better and good enough for the walk down the mall to M•A•C in a somewhat quiet mall.

I put on my jewelry, packed away my other clothes and shoes, and walked back to M•A•C, enjoying the sound of my heels on the tile floor. I avoided being looked at ~ when someone would look my way, or if I was even passing or about to pass someone, I did some "window shopping" and kept my gaze directed at the stores.

Back at M•A•C, I found the makeup lady had kept her promise.

One difference between M•A•Cand the department store counters: the department store makeovers are free. M•A•Ccost $50 but you can put that towards a purchase. I was OK with that, and I bought a couple of the products she used on me: powder and lipstick, and I picked up a foundation that matched the powder. I can't remember; I may have picked up a blush as well.

My quick change wasn't as quick as I expected, and she took her time on the makeover but I didn't leave too much after 11, feeling fine and femme.

One difference between mall makeovers and do-it-yourself: the store employees want to do a female makeover on a female face. My face needs a bit heavier hand than they use. I think I didn't look as femme as I would have liked to, but I think I was OK. I also think my number 1 or 2 wig would have made a difference.

Good enough. I thanked and (over)tipped the makeup lady and asked for her card. I also asked her to take a picture or two before I left, which she did.

Most days, I walk to the mall from the office if I want to get lunch there, or maybe shop. Today I drove, just because the ten minute walk is a two minute drive and I wanted to be out of the office as little as possible.

It was time to face the office.

Meeting Meg

Even though it was close to lunch time, I saw almost no one in the parking lot or lobby. I was going to go into the cafe on the first floor, just to say hi, but I didn't really want to have to explain myself or tip off anyone from my office who might be down there.

As part of my pre-Halloween visit, I scanned my card and replaced my male pic with one of Meg. I left my name. I put this over my card ~ we use contact readers so all I had to do was hold the card up to the reader to get into the office.

I went up (alone) in the elevator to the top floor. I walked through the glass doors straight to the receptionist.

We do not get a lot of visitors. We get groups of strangers in for training in the morning most weeks, but by lunch time they all have temporary badges and they are not going into the secure areas anyway.

She said, "May I help you?" and I grinned and showed her my badge without saying a word. She looked puzzled for a second, then burst out laughing. I gave her a broad smile and headed towards the side where I sat (there are two sides, one is training, consulting, IT. The other is finance, marketing, and things like that).

As I held the card up to the reader she was still laughing.

I walked past my desk to N's office. She wasn't there. OK, this wasn't good, but it wasn't bad. I noticed S, our office fashionista, was talking to one of the guys from marketing. I stood behind him, where S could see me while they chatted about this and that. After a minute or so, S said, "Can I do something for you? I'm S."

I said, "I know that. I'm..."

She let out a yelp that I was sure alerted everyone on the floor. I saw our head of security who was maybe ten yards away look towards us. S screeched, "{male name}" and got up and hugged me. She asked what I was doing dressed like that and I told her N suggested I do this for Halloween.

S seemed to genuinely enjoy my new persona. I wasn't sure what I was going to do next. I came in to show N and had no further plans really. I usually interacted with about a third of the people on the floor ~ mostly the ones on my side of the office. Marketing and other corporate activities... not so much.

But S took over. She took my hand and brought me to the nearest employee, a woman who had an office on our side, but the opposite wall from my desk. S introduced me with a made-up name and said I was there for an interview. She offered her hand, we exchanged greetings and she saw my badge and started laughing. Then when we left she joined my new posse.

Most of the people on my side were out or in training sessions or gone for an early lunch, so S grabbed my hand again and off we went to the other section. There she introduced me to one of the accounting guys by a different name and said I was "her new assistant." Again, we got away with it for a short time ~ this time, he said something like "what do you think of {the company}?" and I said, "I've been here for a year. I've only been S's assistant for a little while" and he looked confused so I showed him my badge.

As S dragged me around the floor our little group grew and camera phones appeared. I posed for a couple of pictures, and pictures of my meet-and-greet were taken. Each time, S gave me a different name and a different title. When we got to accounting, I was the "marketing representative for the midwest." When we got to marketing, I was in "product quality." In shipping, I was "the new trainer." Each time I was greeted, usually with a handshake and once with a look that was so close to a leer that I got a little hint of what women have to put up with from guys just being guys. He seemed VERY embarrassed when he realized who I was. And I was VERY relieved that he was embarrassed. :)

Our IT head came over to me later and told me I looked great. Then he did the same thing a few days later.

I had a great time, but I hadn't met with my manager yet. She was in a conference room giving a presentation for a potential client.

I told S that my goal was to meet with N and this was much more fun that I could have ever hoped for. I thanked her profusely. She had to meet a friend for lunch and I was on my own again. Well, almost. A couple of the women came by to talk to me, which was unusual and nice. Oh... the head of security saw me as she was walking through the cubicle farm on my side of the office and yelled out, "Hi {male name}." I later asked her how she knew and she said "it was obvious." But I knew she heard S's first squeal and my "secret" was out ~ to her.

One of the women went into the conference room and got N's attention and told her I wanted to see her. She said it would be another ten minutes and this was relayed to me.

It was way longer than ten minutes, but I spent some time getting an idea as to what it's like to work in an office as a woman. I continued with my usual routine except for my usual coffee overdose. I did NOT want to have to use the ladies' room.

N finally got out of her meeting and came to my cube. She took some pictures and seemed to genuinely enjoy my "Halloween costume." I waited around for her boss, J, to see me, but he was out of the building at a meeting and never made it back. I finally returned to the mall and did a quick "undo." I was back in the office looking male within a half-hour.

Even though I was the only one in the office "dressed for the holiday," I felt great, not embarrassed like I thought I might be. Everyone seemed to enjoy it and one of the managers sent out an e-mail to all staff commending me on bringing cheer to our normal end-of-month crunch.

Alas, I'm in what is technically a military installation right now. I doubt there will be a repeat for 2012. But maybe I can finally make it to the high heel race.

(Not long after this, I came out to S. I figured she earned it, and I wrote about that here.)

Wearing Fashion to Figure.

Laurette's 1989 Southern belle Halloween costume