WorkingGirl Part 1 of 6
by Melanie Brown
Copyright  © 2021 Melanie Brown

Garner thought it would be fun to sign up for a costume contest

 

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“Now?” I asked incredulously. “You want me to do this now? It’s only like eight thirty.”

“Sure!” exclaimed Sarah. “It’ll be more fun this way.”

I frowned, “I don’t know, guys. The contest isn’t until three thirty. I’ll have to be in costume all day!”

“That’s what makes it fun,” said Annette. “Besides, this way you can come to lunch with us.”

I laughed, “I could go to lunch with you without this, you know.”

Katrina laughed louder, “In your dreams!”

“Gee, thanks,” I furrowed my brow. “If you want me to change now, we need to check with the boss first. She may not want me to do this.”

Everyone followed me the twenty feet to Ms. Lane’s office. Her door was open, but I knocked anyway. She looked up, “You need something, Garner?” She then looked curiously at the women who had followed me to her office. “Is there a problem?”

I hesitated a moment before speaking. I’ve always been shy and it’s hard for me to talk to authority figures. “I… uh, Sarah wa… wants me…”

Sarah interrupted and said, “I thought it’d be fun if Garner put on his Halloween contest outfit now instead of waiting until after lunch.”

Ms. Lane flashed us a why are you bothering me with this expression. She said, “What are you… Oh yeah. Katrina told me yesterday you’re going to dress as a woman? I don’t care if you do it now. As long as you don’t disrupt the office more than you already have.”

Sarah grinned and said, “Well, there you have it! Go into the women’s restroom to change. We’ll stand guard so no one walks in on you.”

“I don’t know…” I said. “I’ll feel silly.”

Katrina said, “You brought it up. You showed me that picture of you dressing as a woman for that Halloween party you went to two years ago back in college before you started working here. You looked amazing!”

Laura laughed, “He’s almost a femboy now. Look at his face.”

Sarah looked at Laura sideways and asked, “What do you know about femboys?”

I stepped into the women’s restroom with my bag of clothes and shoes. Talk about being embarrassed! I should never have shown Katrina those pictures. But she’d asked what was the craziest thing I’d done for Halloween. I’m a quiet, withdrawn kinda person so I don’t have many moments of getting crazy.

While musing, I had been slipping into my bra, panties and pantyhose. I know most women don’t wear pantyhose these days but I thought it would help my legs look better. I shaved my legs and underarms the night before. I then slid the dress over my head. It was a work appropriate short black dress. I also had black pumps with three inch heels.

Along with the dress and underwear, I got the high heels a week ago. While it’s hardly my first time to wear heels, I have been practicing walking around the apartment. At first my roommate, Jack, would laugh, but now he doesn’t even notice. My roommate claims he’s bi, but I’ve only seen him with women. We met at college and he needed help with the rent and I needed a place to live. And this is my first real job since graduating. And I’m putting on a dress.

And I have to confess. I like to cross dress. I went through a purge last year and tossed out all my nice feminine clothes. Well except the panties. I still wear those. But looking at myself in the mirror wearing a dress, all those urges are returning. I wonder if Jack would toss me out of his apartment if I started dressing?

I opened the restroom door and said quietly, “Okay, I’m dressed. Katrina, did you bring the make-up? You want to help me with it?” I didn’t want to admit that I have my own make-up.

Grinning ear-to-ear, Katrina said, “Yep. Don’t worry. I’m not going to make you look ridiculous. But look at you! You look great even without make-up! Let’s do the make-up in the meeting room.”

I followed Katrina into the meeting room next to our cubicles. I sat down in one of the chairs and Katrina spread the make-up out on the table.

My eyes widened and I exclaimed, “You’re going to put all that on my face?!”

Laughing, Katrina said, “No silly. I didn’t know what I was going to need, so I brought it all.” She opened a lipstick and screwed some of it up. “What do you think, guys? I thought this would be a great color for him.”

Sarah nodded and Laura said, “That’s a good color. You should be a make-up artist.”

Katrina smirked, “Well, I did take cosmetology in college for two years.”

Laura said, “Do you have time to do her hair?”

Biting her lower lip, Katrina said, “Not a lot of time. We can’t spend all day doing this. Ms. Lane would have a cow.” Frowning at me she said, “You should have been letting your hair grow this past year.”

Furrowing my brow, I said, “How the hell did I know I’d be doing this at Halloween?”

Katrina started smearing foundation on my face. She said, “It’s called ‘planning’. You should always plan ahead.” I hadn’t worn make-up since the last time I got fully dressed. I regret tossing out all my girly stuff.

Sarah said, “Don’t listen to her, Garner. She doesn’t even have a boyfriend yet, but she’s already planned her wedding, what kind of house, how many kids and how much she’s going to get in the divorce. And yet she can’t get any of her work done on time.”

Rolling her eyes, Katrina said, “That’s because I’m always doing things like Garner’s make-up and hair.”

Ms. Lane popped her head into the conference room and said, “Can you finish this sex change before nine-thirty? I have a meeting with Mr. Cramer that I want Garner to attend as well.”

A cold shaft ran down my spine. I blurted, “I forgot! The Nelson account meeting! Oh!”

Katrina said, “Don’t move around while I’m doing your eyeliner.”

“I can’t go like this!” I exclaimed. “I can’t go to the meeting, Ms. Lane.”

“You have to go,” said Ms. Lane flatly. “Mr. Cramer wanted Ralph Barnlig for the project, but I convinced him you would be better for the job. Even if I don’t tell Mr. Cramer who you are, you still need to hear the account particulars.”

“Won’t he ask who I am?” I said worriedly. Laura started putting polish on my nails to speed things up.

Shrugging, Ms. Lane said, “I’ll tell him you’re out sick today and that you as a woman are my new assistant. You’re quite convincing and they’re not even done with you, so I don’t think we have anything to worry about.”

Leaning back to get a better look at what she’s doing to me, Katrina said, “Don’t worry, Ms. Lane. We’ll have her ready before nine-thirty.”

*          *          *

“Wow,” exclaimed Sarah. “Where did Garner go?”

“What do you guys think?” I asked as I stood up in my short black dress and high heels. “Do you think I’ll win?”

Katrina said, “I don’t know if you’ll win the contest, but nobody is going to believe you’re a man.”

Suppressing a giggle, Sarah said, “Let’s go in the restroom so you can check yourself out. The transformation is really amazing.”

I just stood there in shock staring at my reflection after all of us had hurried into the women’s restroom. Like always, I found it hard to believe that the cute girl in the mirror was actually me.

As we exited the restroom, Ms. Lane called from across the office, “Oh. There you are.” She walked up to our little group before she said, “I was looking for you. I’m going to head up for the meeting. Can you bring that box of reports we’re going to distribute at the meeting when you come up? It’s on the table outside my office. Thanks. And you look great, by the way.” Without waiting for an answer, she hurried off towards the elevators.

Katrina nodded at me. “You do look great. I think you should dress this way all the time!” She, Laura and Sarah all laughed.

I frowned. “Well, thanks.” Actually, if I was being honest with myself, I wished I could dress this way all the time.

Laura said, “We’re not laughing at you. We’re just thinking how fun it would be for you to wear a dress every day. It does suit you.”

I sighed heavily. “Well, as much as I don’t want to, I better get up to the meeting.” I started to walk towards the elevators.

Sarah pointed towards Ms. Lane’s office. “Don’t forget that box she wants you to bring.”

Katrina looked puzzled. “Why print the reports? Just put them on-line.”

I grunted a laugh. “It’s a bunch of old farts who like to hold paper.”

As I walked over to the box, I started to wonder how I was going to pick it up without messing up my nail polish, even though it should be dry by now. I decided to slide the box into my arms rather than try to pick it up from the table. It wasn’t especially heavy, but it was heavy enough that carrying it while wearing heels would be awkward.

As I stood there, trying to adjust the weight distribution of holding the box, an IT guy who’d just finished working on a PC pulled the box from my grasp. “Let me help you. That box is bigger than you!” It wasn’t of course.

“That’s fine,” I said reaching for the box. “I got it.”

He smiled at me. “It’s no bother. Where are you going with it?”

Still trying to reach for the box, I said, “Board meeting room on the tenth floor.”

Grinning and keeping the box out of my reach, the man said, “Oh yeah. That’s too far. I’ll follow you.”

Well, that’s annoying. I’m sure he feels he’s being helpful, but carrying the box wasn’t going to be difficult. But refusing to let him help me would probably bruise his ego. There was certainly no doubt why he wanted to follow. I could almost feel his eyes on my butt. I laughed to myself. If he only knew he was staring at a guy’s butt. A guy’s butt in black, lacy satin panties and wearing a short, black dress.

Maybe I’m laughing at the wrong person…

The board room was right across from the elevators. The IT guy followed me in as I walked over to where Ms. Lane was sitting. I pointed to the space next to her. “You can set it down there. Thank you so very much!”

The IT guy gently set the box down on the conference table without so much as a grunt. He smiled at me. “My pleasure, ma’am.”

He turned to leave. One of the managers already seated at the table called out, “Hey Bill. Can you come by and look at my PC later?” Bill nodded and left.

As I started taking individual reports from the box so I could distribute them, Ms. Lane grinned at me. “Already asking men to help you with hard things?”

Feeling extremely self-conscious about being in a room filled with male managers I said, “Hey. He volunteered.”

Ms. Lane smiled. She then pointed around the room. “While you’re doing that, would you mind handing those reports out around the table?”

I looked around the room. Most of the seats at the large conference table were already filled. This was going to be a major management meeting. And I’m wearing a dress.

About a third of the managers attending were women so I didn’t feel quite so alone in a sea of men. Most of the attendees ignored me as I walked around the table placing the reports. Some of the younger men watched me as I went back a couple times to get more reports. Most of the women managers would at least smile and say “Thank you” when I placed a report in front of them.

When I was done, I returned to Ms. Lane. I bent over and whispered, “Is that all you need, Ms. Lane?”

Ms. Lane looked at me for a second. “Would you mind staying and taking notes for me? And they’re going to be talking about a project that will involve you anyway.”

“Of course, Ms. Lane.” I sat down next to her. She slid a pen and a pad over to me. Well, I tried to get away.

Mr. Jones, the CEO entered the conference room after everyone was seated. “Good morning ladies and gentlemen. It’s good to see everyone here.” He glanced around the room. “I think I know all of you by now. Anyone new to this meeting?” He focused on me and Ms. Lane.

Ms. Lane looked a bit flustered at the unexpected attention. She looked quickly over at me. “Um… this is Ms. Garner Carter. She’s my new assistant.”

Mr. Jones looked directly at me and smiled. “Welcome aboard our team, Ms. Carter”

I smiled weakly and in a small voice said, “Thank you, sir.” Oh wonderful. Now I’m a secretary, the stereotypical dream job for a crossdresser. I hope Ms. Lane was just making that up. I’m supposed to be in analytics. I looked around the table and became even more uncomfortable seeing that, with the notable exception of Mr. Jones’s assistant, I was the only non-manager there.

Mr. Jones looked around the room with a slight frown. “We’re waiting for one more person to arrive.” About thirty seconds after he spoke, a young woman entered the meeting room.

“Sorry I’m late, Mr. Jones,” the woman said nervously.

Mr. Jones nodded towards her. “Please have a seat so we can get started. Everyone, this is Nancy. She temporarily filling in as executive assistant. I think most of you know that Judy, my previous assistant retired last week.”

Nancy looked around the room for a moment and then opened her laptop computer and turned it on. I leaned over to Ms. Lane and whispered, “Why does she get a laptop computer to take notes on and I get this pen and yellow pad?” I was only joking. Sort of.

Ms. Lane looked at me funny and then smiled. “Well, Miss Carter, if you work out as my assistant, we’ll see about getting you a laptop.”

I smiled dourly and nodded. I held up the pen and whispered, “I’m good.” Ms. Lane chuckled at me.

Nancy glanced over at me, flipped her hair over shoulder and then sat with her fingers poised over the keyboard. Maybe it’s my imagination, but I felt she was trying to signal to me that I was at a lesser station in the assistant pecking order. My hair wasn’t long enough to do any flipping, so I just sat up straighter and held my pen at the ready.

Ms. Lane leaned over to me again and discreetly pointed under the table and whispered, “Keep your knees together, Miss Carter.”

I nodded and consciously brought my knees together. Women don’t have body parts between their legs, so it’s easier for them to keep their knees together. That’s my assumption anyway.

Everyone sat in silence as Mr. Jones glanced over the report. “Okay, everyone, let’s look at these issues pointed out on page two of this report. Oh by the way. This is an excellent report, Ms. Lane. The guy who wrote this really knows his stuff.” A cold spike shot down my spine when I realized my name is on the report.

Ms. Lane smiled. She pointed at me. “Thank you sir. The credit should go to Miss Carter as she did most of the research and prepared the report.” All eyes turned to me and Ms. Lane grinned at me, obviously enjoying my discomfort.

Mr. Jones smiled at me. “Excellent work, Ms. Carter. Excellent work. And my sincere apologies for assuming you were male. Sometimes it’s hard to change your mindset. Again, thank you, Ms. Carter. Now, let’s continue…”

Oh my God! The boss now thinks I’m a woman. From now on, whenever he sees my name on a report, in an email, or whatever, he’s going think I’m female. Before I was a nobody grunt, working invisibly cranking out reports. Now I’m known to management only as Ms. Lane’s female assistant. How the hell are we going to get this fixed?

I glanced over to Ms. Lane. She just shook her head with an amused expression.

My note taking was interrupted multiple times during the meeting as not just Mr. Jones, but other managers asking me for clarifications on some finer points in my report. I was embarrassed as hell, and actually annoyed that they’d ask for clarification since as far as I was concerned, the report was very clear. But I didn’t say that. I just answered as best I could in a quiet voice. I was very worried my voice would give me away.

I was actually surprised that I was completely accepted as who everyone had been told I was. People seem accepting if you don’t give them a reason to suspect you’re not who you say you are. That was my experience the few times I dared to venture out dressed as a girl in years past.

The meeting lasted a bit over an hour and a half. I took lots of notes for Ms. Lane and answered a ton of questions. Several managers just stared at me the whole time smiling, making me very uncomfortable.

As we started to stand up, Ms. Lane said, “Thank you so much, Garner for stepping up to come to the meeting dressed as you are. I know it was probably a bit embarrassing, but you helped me out a lot being here to answer questions.”

I smiled at her. “You’re welcome, Ms. Lane. In a way it was sorta fun. I felt like a spy in disguise.”

Before Ms. Lane could comment further, Mr. Jones started walking towards us. “Oh Ms. Lane. May I have a word with you?”

Ms. Lane nodded in his direction as he approached. “Of course, Mr. Jones.” I stood silently beside Ms. Lane.

Mr. Jones smiled broadly as he walked up to us. “Ms. Lane, I wonder if I could ask a favor of you? Here in about twenty minutes, I have to attend a board meeting to basically go over what we just discussed. I was wondering if I could borrow your assistant, Ms. Carter? Her intimate knowledge of the report and how the conclusions were arrived at would be invaluable.”

I thought to myself, “Please say no.”

Ms. Lane smiled. “Well of course, Mr. Jones. I’m sure Miss Carter would happy to provide you with any assistance you may require.” Ms. Lane nodded at me a couple of quick nods.

I smiled at the big boss. “Yes, Mr. Jones. I’d be happy to do whatever you need me to do.”

Mr. Jones gave me an odd smile. “I’m sure you would, Ms. Carter. Thank you Ms. Lane. I’ll probably require her services the rest of the day.” He turned to me. “And not to worry. Lunch will be provided for the meeting. One of the reasons I don’t mind going to board meetings.” He chuckled.

Ms. Lane smiled at us. “Enjoy your meeting.”

Mr. Jones turned to me. “If you’ll follow me, Ms. Carter, we’ll go ahead and go up to the executive board room. Have you ever been up there?”

I shook my head. “No sir.” I looked frantically at Ms. Lane as she turned to exit the meeting room.

Ms. Lane looked exasperated and silently mouthed the world “Sorry!” She then shrugged.

Nancy had been standing by the door this whole time. As he passed her, Mr. Jones said, “That’s all for today, Nancy. Thank you for filling in. You may return to the assistants pool.”

“Yes, sir.” She shot me a dirty look.

I followed Mr. Jones out to the open area in front of the elevators. As the elevator door closed with just us two in the elevator, I was suddenly gripped in a fear Mr. Jones would rape me in the elevator. I know it’s irrational, but I suddenly felt very vulnerable wearing a dress, heels and being alone with a man. We only went up three more floors, but it was the longest elevator ride I’ve ever been on.

As we got off the elevator, I had a sudden thought. “Oh. Do I need to go back to Ms. Lane’s office and run off more copies of the report?”

Mr. Jones smiled at me. “Oh no. The board members all have pads and the report should already be loaded on them. But that’s good you thought of that. That’s what makes a good assistant.”

I smiled at him. “Thank you, sir.” I looked about the lobby at all the big shots going into the board room. I was surprised that there were two women on the board. Any other time I might have made a sexist joke about women on the board. But I just felt less alone wearing a dress.

Mr. Jones looked into the board room. “You know what else makes a great assistant? Could you bring me a cup of coffee? I have to talk briefly with the finance director before the meeting.”

He walked away before I could respond. But what could I say besides “Yes sir?” And of course, here we are. He praises my report, but I’m still expected to bring him a cup of coffee.

I looked over at the gathering of other assistants at the coffee machine, filling cups for their bosses. I sighed and walked over to the coffee machine, picked up a cup and waited for my turn to fill it.

*          *          *

End of Part 1