The Women's Job - It's Confidential - Chapter One

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The drive home seemed longer than usual, as Dylan was thinking about the rather strange offer his boss had given him. He barely noticed when it started to rain.

He knew that the Connell contract meant a lot to the company. This wasn’t just big, it was huge. If they didn’t get the contract, it could mean layoffs or worse.

In a way, he felt honored that he was being considered for the job. True, part of the reason he was being considered was his slim physical appearance. He also had a very young-looking face. His co-workers kidded him about being carded when they went to the Seahawks game, even those who were younger than he was.

Part of the reason for his youthful appearance was his almost total lack of facial hair. It was a family curse, as no men in his family had beards. Thankfully, he had a full head of hair. It was currently long by corporate standards, but it was far from feminine. So, he’d have to wear a wig, he thought.

He had told Mr. Wade that he had never dressed as a girl; this wasn’t completely true. There had been a few times for Halloween. Then there was that party back in college. He had tried to put the events of that night out of his memory. No, it was best to lie and say that he had never dressed as a girl.

He wondered about this strange woman who would make men dress in drag. Did she do it just to humiliate them? It couldn’t be just that, otherwise, Mr. Wade wouldn’t still be going for the contract.

Dylan wondered about who the others had been who had to dress up to appease Savannah Connell. It would be cool to be a VP, he thought.

Dylan heard all the company gossip, and he had never heard a thing about what Mr. Wade had talked to him about. So that meant that if he did it, it was unlikely that anyone would find out.

He then thought about the bonus. He mentally computed the standard commission for a sale against the size of the contract. He smiled at the figure he came up with. It would be huge!

Well, he didn’t have to make up his mind right now, he thought. He decided that he needed a mindless diversion that night; so after he went home, he changed and headed up to Seattle to watch the Supersonics play.

Dylan decided Saturday morning that he would take the job. The good things that could come out of it far outweighed the bad things. He waited until after nine before calling Mr. Wade.

“I really appreciate you taking on this task, Dylan. I won’t forget it,” stated Mr. Wade.

“So, when do I have to go there?” asked Dylan.

“Not for a couple of weeks,” said Mr. Wade. “In the meantime, you have some training to attend. You need to get a whole new wardrobe, and learn how to apply makeup, do your nails, and things like that.”

“I don’t even know where to start,” replied Dylan sheepishly.

“Don’t worry; we have an expert who’ll help you. We’ve used her before, and she can be trusted. Her name is Tess, and she runs a business that caters to the transgendered.”

“Um, okay,” said Dylan.

Mr. Wade laughed. “Dylan, she knows that you’re not transgendered. Like I said, she’s helped us before with this contact. I’ve already taken the liberty of setting up an expense account with her. I want you to call her today and set up an appointment. Starting Monday, you’ll be officially attending training as far as anyone at work will know.”

Dylan copied down the number for Tess’s Transformations.

“Dylan, I’ll call you later this week with the details of the trip to see Ms. Connell. I have a good feeling about this, and I have the greatest confidence in you.”

“I won’t let you down, sir,” replied Dylan.

They talked for the next thirty minutes about the details of the trip. By the time the call was over, Dylan knew that this would make or break his career.

After he hung up the phone, he called the number for Tess’s Transformations.

“Good morning, Tess’s Transformations, my name is Jackie, how may I help you?” asked the woman.

“Hi, my name is… my name is Dylan, and I need to talk to Tess Wellington,” he said.

“Oh yes, she’s been expecting your call. I’ll transfer you,” said Jackie.

A moment later, Dylan was talking to Tess Wellington.

“Your boss called me Friday and said that he expected you to take the job,” said Tess.

Dylan was slightly surprised by this, but it did make him feel good that Mr. Wade had that much confidence in him.

“So, you know why I need your services?” asked Dylan.

“Oh, yes, we’ve helped out several of your fellow employees with this issue. I’ll have you know that I take great pride in the fact that your company has always gotten the contract,” said Tess.

“Really?”

“Oh, yes. I take great pride in my work, and when I’m done with you, all you’ll have to worry about is the contract,” said Tess. “By the way, I have a stake in this too. We get a bonus when you get the contract.”

“That only seems fair,” said Dylan.

“So, can you stop by today? I’d like to get your sizes so I can start on your wardrobe,” explained Tess. “That way, when you come in on Monday, I’ll have something appropriate for you to wear.”

“Sure, why not,” he replied.

“Okay, I’ll pass you back to Jackie, and she’ll give you directions to my office. Oh, have you picked out a fem name yet?”

“No, not yet,” replied Dylan.

“Well, you can always call yourself Diane.”

“I’d rather not. I dated a Diane for a while.”

“Okay, how about Dana?”

“Um, I guess that sounds okay.”

“Trust me; it’ll help you adjust to this if you already have a feminine name. So, Dana, I look forward to seeing you shortly,” said Tess.

Dylan parked in front of what looked like an old warehouse. He looked around the neighborhood and judged it was safe. It was one of those old industrial areas of town that were undergoing a minor renaissance. He stepped out of his car and walked up to the main door and rang the bell.

An attractive redheaded woman answered the door.

“Hi, I’m Dylan, I called about seeing Tess,” he said.

The woman escorted him inside. “My name is Jackie. Tess will be out shortly, would you like some coffee?”

“Yes, please. I take it black,” he replied. He watched as the woman walked away to get the coffee. She was dressed in a stylish-looking navy suit.

A short time later, she returned with the coffee. “I hope you like it, it’s Kona.”

Dylan was feeling slightly better about all this. If they could afford high-end coffee, then it must be a legitimate business.

“Can I get you to fill out this form, please?” asked Jackie.

Dylan sat down and looked over the form. It had the standard information; name, address, phone number, and e-mail address. There were also places to fill in height, weight, shoe size, and things like that.

“Just so you know, everything is kept strictly confidential,” said Jackie, as she sat behind her desk. “If it makes you feel any better, we’ve never had a security breach; and we have some very public clients.”

This caught Dylan off guard. “Really?”

Jackie nodded. “Everyone from athletes to politicians, however, we treat everyone the same here. We understand the importance of maintaining a client’s privacy.”

“I’m just doing this for work,” said Dylan, sort of defensively.

Jackie smiled. “There’s no need to explain. What matters to us is that you get the best service possible, and part of that is maintaining your privacy. Trust me, I understand all about privacy.”

Dylan looked at the pretty woman and then went back to filling out the form. There was no way she could be a guy, he thought.

A few minutes later, a black-haired woman walked into the reception area and greeted Dylan.

“It’s a pleasure to meet you, Dylan, or is it Dana?” she asked.

“I prefer Dylan, but I suppose I should get used to answering to Dana.”

Tess smiled. “That’s the spirit, Dana. Follow me back to my office, and we’ll get started.”

Tess took a series of measurements and nodded approvingly. “Your size will make clothing shopping much easier. I’ll have more options than if you were taller or more muscular.”

Dana cocked her head.

“I’m sorry; I didn’t mean to imply anything negative. I was speaking strictly from a wardrobe side. With some of our clients, obtaining a wardrobe can be… challenging,” said Tess.

“What do you mean?” Dana asked.

“Do you know how hard it is to find high heels for a man’s size fourteen?”

Dana laughed. “I have no idea.”

“I finally found a company down in LA that not only stocks large size shoes, they’re high quality too, but extremely expensive. Anyway, I won’t have that problem stocking your wardrobe. From our past experience with your company, I know that you’ll need enough changes of wardrobe for three weeks; and that is just for work. You’ll also need casual clothes, and some evening wear. You’re lucky that you’re not buying this yourself,” said Tess.

“I imagine that they’ll write this off as a business expense,” said Dana.

“I never thought of it that way,” replied Tess with a laugh. “I’ll also have to get you shoes, accessories, and makeup.”

“Accessories?” asked Dana.

“Jewelry, handbags, outerwear,” said Tess as she counted off the items on her fingers.

“Oh, yeah,” said Dana. “What about a wig?”

“Won’t be necessary; your own hair is long enough that we can have it styled. It’ll be short, but I have a good hair stylist who can give you a feminine look. Trust me, you don’t want to deal with a wig,” said Tess.

Dana hadn’t counted on this. “Um, if you say so.”

“Now, according to your boss, you’ll be leaving in three weeks. I suggest that we have you start dressing as soon as possible.”

“Do I have to?’ asked Dana.

“You need to get used to the clothes and the persona you’re going to portray. Remember, you’re going there to get a contract, and that should be the only thing you’re worried about.”

Dana nodded. “Can I ask you a question; don’t you think that this is sort of weird? I mean, why does Savannah require this sort of ”

“Humiliation?” interjected Tess.

Dana nodded again.

“Have you read about her?” asked Tess.

“Just a few articles,” replied Dana.

“She’s a very remarkable woman. She had to fight to get where she is; she didn’t get to be CEO just by birthright. Before the accident, she was a top test pilot; in addition to holding numerous degrees from avionics to business. She didn’t just succeed in a man’s world, she excelled.”

“How do you know so much about her?” asked Dana.

“It was right after your company first hired me. She intrigued me. I mean, here is a woman running a major company, who has enough clout to make men dress as women.”

“Okay, but what about that, I mean requiring men to dress in women’s clothes?”

“I suspect she does it to make contractors hire more women; and if that failed, to at least give the men a feeling of what a woman has to go through. Now, if you were going on a normal two to three-week trip as Dylan, how many suits would you take?”

“Three, maybe four, less if the hotel had its own dry cleaning service and could do next-day service,” Dana replied.

“Exactly! A woman can’t get away with that. If she shows up wearing the same suit, it doesn’t look good. Also, she has to make sure her hair, nails, and makeup are perfect.”

“I hadn’t thought about that. This is going to be harder than I thought,” Dana said.

“From what I’ve heard, she’s not doing this for anything sexual. She will try to push your buttons a little and push your limits. If you get the contact, expect to have to dress up for at least one fancy dinner,” said Tess. “She also does something new each time.”

“What do you mean?” asked Dana.

“Well, the last time, she rewarded the salesperson with dinner and a Broadway show. Of course, the person had to accept, even though he had to go as a woman.”

“Oh my god,” exclaimed Dana.

“It wasn’t that bad. I talked to the person afterward, and he had to admit that they had a pretty good time.”

“Wait for a second; I thought Savannah never left her estate.”

“She doesn’t. The salesperson went with a friend he knew out there.”

“A friend? You mean a woman?’ asked Dana.

Tess shrugged her shoulders. “I don’t know, the person never said. He did say that they had a wonderful time.”

Dana wondered if it was too late to pull out.

“Okay, I have your sizes and will have your initial wardrobe here Monday. Now, again I suggest that you transition as soon as possible.”

Dana nodded. “I suppose you know best.”

“Great. I already made appointments for you at my friend’s salon.”

Dana laughed. “You’re good.”

Tess smiled back. “It’s my job. Trust me; you’ll pass very well, Dana. Now, getting you dressed is just part of the program. We’ll be taking you out; this way you’ll feel more at ease by the time you get to New Jersey.”

“What do you mean by we?” asked Dana.

“Well, you’ve already met Jackie; there’s also my other associate, Lisa. Don’t worry, you can trust both of them,” explained Tess.

Dana nodded. “So what sorts of places will we be going to?”

“Stores, restaurants, and also I want to take you to a local club. If you can survive Anything Goes, then you’ll definitely be prepared for Savannah Connell,” said Tess.

“Well, maybe when this is over I can write a book,” remarked Dana.

Dylan drove home thinking about what was about to happen to him. Starting Monday, he would be Dana Matson. He was nervous about what was about to happen, and it had nothing to do with Tess’s skills.

At the same time, Tess was heading out to do some shopping. She already had a good idea of how she would dress Dana. She suspected that Dana was hiding something; she had been in this sort of business long enough to read her clients like a book. It didn’t matter to her, as her own receptionist had once been a young businessman named Jack. Jackie was now engaged and living full-time as a woman.

Tess figured that if Dana had some gender issues, they would come out before or during her time in Jersey.

She did place a call to Mr. Wade.

“What do you think, Tess?’ he asked.

“Well, if you don’t get the contract, it won’t be because she doesn’t pass,” she replied.

“Dylan is a damn good salesman. I have the highest confidence in him to make the sale,” said Mr. Wade.

“Um, don’t you mean, the highest confidence in her?” asked Tess.

“True. I keep forgetting that. So, what’s Dylan’s new name?”

“Dana,” said Tess. “I plan on having Dana living as a woman Monday.”

“So soon?”

“How soon do you need her in Jersey?” asked Tess.

“Two weeks from Tuesday,” he replied.

“What do you think?”

“Well, you’ve never been wrong before,” he replied.

“Oh, just in case Dana decides to stick around when this is over, she will have a job, right?”

“Of course. So, does that mean you think that Dana will be like Leslie?”

“I don’t know yet,” replied Tess. “By the way, how’s Leslie doing?”

“She’s VP of marketing in our Minneapolis office,” said Mr. Wade.

“I’m very happy for her. I’m also happy that she works for such a progressive company.”

“Hey, it’s the least we could do. I mean, I picked her for the job. If Dana sticks around, as you put it, then we’ll definitely find a job for her.”

“I’m glad to hear that. I’ll talk to you later this week and give you an update on Dana’s progress.”