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

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Dana dried herself off as she stood in the shower stall. The lack of body hair felt strange as if her body was suddenly more sensitive.

Just fifteen minutes earlier, Tess had coated most of Dana’s body in a hair removal cream.

After Dana dried off, she slipped on the gaff, remembering Tess’s instructions. Dana was still shocked when she saw how well it hid her male genitals. Next came the panties. They were white and made of cotton.

Dana looked at the bra, and after several attempts, she was able to get the band hooked behind her back. She then picked up one of the silicone breast pads. It was surprisingly heavy, and Dana had to marvel at the way it jiggled. She slipped it into her bra, followed by the other one. As she walked around the bathroom, she was amazed at the way they felt.

“This will take some getting used to,” Dana said aloud.

“Are you dressed?” asked Tess from the next room.

“Yes, I’m coming out,” said Dana.

Tess nodded approvingly as Dana emerged from the bathroom.

“Okay, turn around,” Tess ordered. “I want to see how the bra fits.” She then walked over and made some adjustments with the straps.

“That feels better,” said Dana.

“Good, let’s get you dressed. Then I’ll do your makeup.”

She handed Dana a pair of black pantyhose. “Sit down on the bench. Now, what you do is roll up the legs and stick your feet inside.”

After two attempts, Dana was able to get the pantyhose on.

“I’ll teach you how to do stockings later, but for today, we’ll keep it simple,” said Tess.

“What’s next?” asked Dana as she ran her hands down her legs.

“Stand up and try on this skirt,” said Tess.

Dana slipped on the dark gray skirt. She needed some help from Tess in aligning it.

“Okay, now slip on this blouse.”

Dana held it and noticed how soft it felt.

“It’s silk,” stated Tess. “The buttons are on the opposite side, but otherwise it’s no different than a male shirt, at least when it comes to putting it on.”

Dana slowly buttoned it up. “Why are the buttons on the opposite side?”

“Just to confuse people, I guess,” replied Tess with a wink.

“Okay, what’s next?’

“Try on the shoes. They’re only two-inch heels. I have some others that have a higher heel, but not for your first time,” said Tess.

“They fit perfectly,” noted Dana.

“Good. You’re a size nine in shoes. Thankfully, you have small feet, so getting shoes isn’t a problem. I bought you a couple of pairs of boots too. Now, sit down at the makeup table, and I’ll do your face. We need to get to the salon; so right now, I’ll just do your face. This afternoon, I’ll give you your first lesson.”

Tess went to work on Dana’s face. “How often do you shave, Dana?”

“Only a couple times a week,” Dana replied. “I’ve never had much facial hair.”

“Well, that’s a blessing. Trust me, you don’t need razor burn,” said Tess. “Now, the trick of doing daytime makeup is to make it look like you’re not really wearing any makeup.”

“That doesn’t make sense,” said Dana.

“I know. But you can’t wear too much makeup at work; it looks unprofessional.”

“What about my hair?”

“I have a wig for you to wear until we get to the salon. It’s close to your own color.”

Dana reached up and ran her fingers through her light blonde hair.

“You have very nice hair; Maria will be pleased,” said Tess.

“Who’s Maria?” asked Dana.

“The woman who is going to give you your new look,” said Tess. She then looked at the side of Dana’s head. “I’m glad to see that you have pierced ears. That gives us a lot more flexibility. Put these hoops in.”

Dana looked at the two gold hoops that Tess had handed her and nodded. She took out the studs and then put them in the hoops.

“Good. They look very nice,” noted Tess. She then handed Dana a watch, several rings, and a gold chain. “Here put these on too.”

“You spare no details,” noted Dana.

“Hey, it’s my job! Now, I’m going to give you some notes that will tell you what will go with what, just in case you have any questions,” said Tess as she brushed out a blonde wig. “Okay, let me put this hair helmet on your head. Trust me, even after a few minutes in one of these, you’ll understand why it’s best that we get your own hair styled.”

Tess arranged the wig on Dana’s head and then styled it.

“That doesn’t look too bad; however, you’re going to look fabulous when Maria gets through with you. Now, just so you know, she’s worked with many of my clients and is really cool. She also did the hair for the last few of your company’s salespersons,” explained Tess.

“I’m just a little uneasy about having to pass as female for the next few weeks,” confessed Dana. “I mean, I’m not leaving for New Jersey for a couple of weeks.”

“You’ll do fine, and by the time Maria’s done with you, no one will suspect that you’re really a guy. Now, here’s your purse and coat; I’ll drive,” said Tess.

Dana sat nervously in the salon chair as Maria styled her hair. For Dana, it seemed like an eternity.

“Can’t I see what you’re doing?” asked Dana.

“Nope,” replied Maria, with a slight laugh. “I’m almost finished, and I want you to see yourself when I’m totally done. Trust me, I’m an artist, and you’re going to look fabulous.”

Dana sighed and noticed that Tess was smiling. “Is she always like this?”

“Yes, pretty much. She’s right though, you will look great,” replied Tess.

Dana looked down at her nails. They were now long, thanks to the extensions that Maria had attached earlier. Dana was amazed at how feminine her hands now looked. The dark red color also would take some getting used to. She then looked at her toes, which also had the same color.

“Dana, as a professional businesswoman, you’re expected to have good-looking nails. I’ll give you the address of a salon in Jersey that you can use. They can be trusted,” said Tess.

“After all this, I’d better get the contract,” replied Dana, as she held out her hands to look at her nails. “Actually, I’m surprised that they’re no longer.”

“You’ll find that they’re long enough. You still have to function, and if your nails were longer it would make typing rather difficult; in fact, you’ll find that it’ll take some getting used to,” said Tess.

Maria then reapplied Dana’s makeup. “I’ve selected a new lipstick that will go better with your new hair color.”

“Okay,” replied Dana.

“Okay, are you ready, Dana?” asked Maria.

Dana nodded nervously.

“Close your eyes,” ordered Maria.

Dana obeyed and felt the salon chair being turned around.

“Open your eyes, hon,” said Maria.

Dana opened her eyes and was stunned by her reflection. Her hair was now a reddish blonde with highlights. It was now styled short on the sides and full on top.

“I’ll show you how to use mousse so you can style it like this,” said Maria. “It’s pretty easy.”

Dana nodded without taking her eyes off her new look. She reached up and touched her now narrow, thin eyebrows. They were arched and changed the entire look of her face. “I can’t believe that’s me that I’m looking at. I really look like a woman.”

“Am I good or what?’ stated Maria.

“You did a great job as always, Maria,” said Tess.

Dana realized that she now looked like many of the professional women she saw at work. She began to realize that she might just be able to pull this off.

“Thank you,” replied Dana.

“You’re going to knock them dead, Dana,” said Maria.

“So, you feel up to doing some shopping?” asked Tess.

“Right now?” asked Dana.

“Sure, why not? Trust me; no one is going to make you; besides, the places I’m going to take you wouldn’t care anyway. You have to do it eventually,” said Tess. “It’ll also give you an opportunity to study how other women dress and move.”

Dana thought about this. In just over two weeks, she would have to be out on her own, and the company was depending on her. “I suppose you’re right,” said Dana.

“Are you hungry?” asked Tess.

Dana nodded.

“Great, let’s go get something to eat, and then we’ll go shopping,” said Tess.

They stopped at a small bistro in the downtown area.

“There are several good boutiques within walking distance,” said Tess. “Now, just relax, you’ll do fine.”

“Please tell me if I do anything stupid,” replied Dana softly.

“Oh, don’t worry, I’ll give you a full grade tonight,” replied Tess with a laugh.

They walked into a small bistro and sat down. Dana followed Tess’s lead and ordered a salad. She began to relax as soon as she noticed that no one was staring at her.

“How’re you doing?” asked Tess.

“Pretty good, I guess. I may have a problem though,” whispered Dana.

“What?” asked Tess.

“I need to go to the restroom,” replied Dana.

“Oh, okay, we’ll go together,” replied Tess.

“What, here?” asked Dana.

“No, we’ll use the alley out back. Of course, here! Just follow me in, go into the stall and do your business. Afterward, wash up and check your makeup, we need to reapply your lipstick after eating anyway,” said Tess.

Dana stared back, but couldn’t think of a reasonable counterargument. “Okay.”

“That’s the spirit,” said Tess. “Don’t forget your purse.”

Tess and Dana stood up and headed to the restroom. Dana was hoping that no one else would be inside. They walked in, and there were two women standing in front of the sinks, reapplying makeup. The women were talking about what an ass their boss was.

Dana went into a stall. She was relieved to hear the other women leave. After she was done, she came out and found Tess waiting for her.

“Do as I do,” said Tess as she began to reapply her lipstick.

Dana followed suit and was pleased that she did it without any mistakes.

“Let’s go shopping,” said Tess.

After passing the restroom test, Dana’s confidence was pretty high. They walked down the street to a boutique.

“That wasn’t so bad,” said Dana.

“You did well, I’m impressed,” said Tess.

They spent the afternoon shopping, increasing Dana’s wardrobe for the trip.

“I had no idea how much I would need for just a few weeks,” said Dana as they dropped another load of bags off at Tess’s car.

“You’ll need everything we’ve bought. We’ve taken care of your work and casual clothes; we still have to get your evening wear. We’ll do that later this week,” said Tess. “We also have to get you some more shoes; however, I think we’ve done enough damage to your company’s expense account for the day. Now, let’s drop off some of this stuff at the dry cleaners, and then we’ll drop the rest off at your place.”

“I never appreciated the fact that I don’t know anyone in my apartment building until today,” said Dana.

“You mean, you don’t know anyone in your building?” asked Tess, as they got into her car.

“No, just the live-in manager. He keeps an eye on my place when I’m out of town,” said Dana. “I live on the third floor, and he lives on the first. I suppose I’ll have to call him and let him know I’ll be out of town for a while. I wonder if I should tell him about my current situation; what do you think?”

“What do you know about him? I mean, how open-minded is he?”

“He’s pretty liberal. We have two same-sex couples in the building,” said Dana.

“I suggest you tell him, that way there’s no misunderstanding,” continued Tess.

“Maybe,” replied Dana.

The man’s name was Pete Nelson. Dana suspected he was in his fifties, judging by the gray in his hair. Pete was a large man, six-three, muscular, and had participated in several triathlons. He was actually a full-time writer and had several works of fiction published. The problem was that none of his books sold many copies. Dana had read one of his books and thought the characters were very good, although the plot was difficult to follow.

Tess helped Dana put away her clothes and then set up her makeup.

“Okay, I’ll see you tomorrow morning at ten,” said Tess. “I want you to practice doing your makeup this evening.”

“Yes, teacher,” replied Dana.

Tess laughed. “By the way, you did very well today. You surprised me; I usually don’t see first-timers as relaxed as you were today.”

“I felt comfortable around you,” replied Dana.

“Okay, see you tomorrow, Dana,” replied Tess.

They hugged at door.

“Thanks again, Tess.”

As Tess drove back to her office, she thought about Dana. It was obvious to her that Dana was hiding something. Tess wouldn’t press it, as it really wasn’t her business, but has helped thousands of transgendered clients over the years, and she could sense that Dana was dealing with something.

Dana poured herself a glass of wine and took a long sip. Her mind was swimming with the events of the day. Until the deal was done with Savannah Connell, she would be Dana Matson.

She nervously picked up the phone and called Pete.

“Hi, Pete,” she said.

“Oh hi, Dylan. What’s up, are you heading out of town again?” replied Pete.

“Yes, but not for a couple weeks. I’ll be out of town this time for several weeks,” she replied.

“No problem. I’ll keep an eye on your place again,” he replied.

“Pete, um… there’s something else. Can you come up here?” asked Dana.

“Sure, I’ll be up in a few minutes,” he replied.

Dana hung up the phone and nervously refilled her glass. She took a sip and had to steady the glass with both hands. “Relax, damnit!” she declared aloud.

A few minutes later, there was a knock at the door. Dana took a deep breath and walked over to the door. She looked through the window and saw that it was Pete.

“Okay, here goes nothing,” she stated. She opened the door. “Hi, Pete.”

Pete’s eyes opened wide. “Dylan?”

“Come on in, I can explain,” she said.

Pete walked in. Dana noticed that he ran his eyes over her.

They walked to the living room and sat down. Dana took care to make sure that her skirt was arranged carefully.

“I’m doing this for work,” said Dana.

Pete cocked his head. “Okay, why?’

Dana explained about the business trip, without giving away specific details.

“And your boss picked you for this?” asked Pete.

Dana nodded.

“Well, I have to admit that you pass really well, Dylan, I mean Dana,” said Pete.

“Thanks. I have a good teacher,” she replied. “I just wanted you to know what’s going on, as I’ll be like this until I leave. I’m not worried about the other people in the building, as I don’t know any of them all that well.”

Pete smiled. “No problem, Dana.”

“Thanks, Pete. Oh, can I get you something to drink? I just opened a bottle of red wine.”

“Sounds good,” he replied.

Dana got up and walked to the kitchen. It might have been her imagination, but she thought she could feel Pete watching her. She returned with the wine and gave him his glass.

“Well, here’s to a successful trip, Dana,” said Pete as he tapped his glass against hers.

“Thank you,” she replied.

They talked for another thirty minutes before Pete got up to leave.

“Thanks for trusting me, Dana,” he said.

Dana smiled back. She then had a funny feeling run through her body; it was one that she hadn’t felt in a very long time.

“You did a nice job on your makeup this morning, Dana. In fact, I’m very impressed with your entire appearance,” noted Tess.

Tess was wearing a dark green blouse, a dark brown skirt, and brown boots.

“You might ease up a little on the eye shadow,” said Tess.

“How about my eyeliner?” asked Dana.

“It’s a little heavy too, but not bad,” replied Tess.

Dana nodded. “So, what are we doing today?”

“We’ll go out to get you some eveningwear. From what I’ve been told, you’ll need several outfits. We’ll get the one item that is indispensable in any woman’s wardrobe, the little black dress,” said Tess.

“Is it really that important?” asked Dana.

Tess nodded vigorously. “Yes, it can be used for everything from a funeral to fine dining.”

Dana laughed. “Hopefully, I won’t be going to a funeral.”

“True. We’ll also get you a nice evening gown. That also means shoes, jewelry, and bags”

“Okay, okay, I get it,” replied Dana with a laugh.

“I’ll take you out this morning, and then we’ll meet Lisa for lunch. She’ll take you out this afternoon. In addition to doing some shopping, she can give you insight into what it’s like to be a businesswoman. She just left the corporate world six months ago,” said Tess.

“Okay, that sounds good,” replied Dana.

“How did it go with Pete?” asked Tess.

Dana laughed. “How did you know that I talked to him?”

“I can tell,” replied Tess. “So, I take it everything went okay, right?”

“Yes, he was really cool about it,” replied Dana.

“That’s good to hear. Okay, let’s head on out,” said Tess.

They made two stops before going to lunch. In addition to the little black dress, they found a nice navy blue cocktail dress.

“I think we did pretty well this morning, Dana,” noted Tess as they pulled into a parking spot near the restaurant where they were meeting Lisa. She’ll help you pick out the right shoes and accessories.”

“How did you hire Lisa?’ asked Dana.

“I met her through Jackie. They used to work at the same company,” said Tess, as they walked into the restaurant. “Jackie used to be a client.”

Dana stopped in her tracks. “No way!”

Tess nodded. “I know it’s hard to believe looking at her. She started her transition last year.”

“I never would have guessed,” said Dana.

“She’s one of my star pupils. I’m so proud of her,” continued Tess.

“You definitely have an interesting job,” said Dana.

“I love it, every day is different.”

They walked inside and saw an auburn-haired woman sitting at a table waving at them.

“Oh good, she already got a table,” noted Tess. “Follow me, Dana, and I’ll introduce you to Lisa.”

Dana was immediately struck by how energetic Lisa was. She also liked her from the start.

“I think it’s so cool that your company is giving you this opportunity,” said Lisa. “I mean, from what Tess has told me, it’s a direct path to a major promotion.”

“If I get the contract that is,” replied Dana.

“Well, by the time we’re done with you, the only thing you’ll have to worry about is your sales presentation. By the way, how are you getting to the east coast?”

“Company jet,” replied Dana. “It would be difficult for me to go on commercial airlines without the right ID. The jet also has the type of ventilation system that we’re trying to sell. We’ll let their technicians examine the actual system.”

“Does this woman have her own airstrip?” asked Lisa.

“From what I understand, there used to be a small one on the grounds of her estate, but she had it torn out after her accident. There’s an airport near their corporate headquarters. I’ll also be bringing a computer demonstration,” said Dana. “I did some more research on Savannah last night before going to bed. I’m impressed with her business skills, but I still don’t know why she requires what I’m going to have to do. I mean, there’s nothing that stands out regarding gender bias in her past.”

“Tess and I talked about this, I agree with her idea. The company that I just left only had two women in my department… well, three if you count Jackie,” said Lisa. “They weren’t against hiring women; in fact, our boss wanted to keep Jackie on, even after he knew she was transitioning.”

“I have a question for you, Dana. Assuming you get the sale and the promotion, you’ll have a much better insight into what businesswomen have to go through. Do you think that will make you a better manager?” asked Tess.

“I suppose so. I hadn’t thought of it that way,” Dana replied.

Dana had fun shopping with Lisa. Maybe it was because they had a lot in common, having worked in the corporate world.

“Now, have you ever dealt with a woman who’s in charge?” asked Lisa, as they looked at some jewelry.

“No, not really,” replied Dana.

“Okay, the first thing is don’t let your guard down. Savannah didn’t get to her position by being a pushover. She’ll do whatever it takes to get the best deal possible, remember that,” said Lisa.

Dana nodded.

“Also, don’t treat her like a date. The worst thing you could do is to treat her differently than you would a man. When that was done to me, I usually found a way to make the offender pay,” explained Lisa. “Do you read Dilbert?

Dana laughed. “Wouldn’t miss it for the world!”

“Good, just remember that Alice has the fist of death,” said Lisa.

“I won’t forget that,” replied Dana.

“Cool. By the way, these earrings will look great with your cocktail dress,” noted Lisa.

“Okay, if you say so,” said Dana. “So, what else will we be doing this week? I mean, we’ve bought a lot of stuff.”

“That’s true,” replied Lisa. “We’ll still go out every day, so you’ll feel more at ease. Also, I’ll work with you on your voice and demeanor.”

“I see,” said Dana.

“You can practice your presentation with us,” added Lisa. “The thing is for you to feel relaxed with your new persona so that your presentation is flawless.”

“Wow, you’ve thought of everything,” said Dana.

“Hey, if you knew the size of the bonuses we’ll get if you the contract, you’d be thorough too,” replied Lisa with a smile.

“Well, that just increased the pressure on me,” replied Dana. She began to laugh.

Lisa started laughing with her. “Okay, let’s pay for this, and we’ll go get a drink.”