Business, Not Quite As Usual
By
Julie O.
Edited by Amelia R.
This story features the characters from Tess's Transformations in
supporting roles.
Chapter 1
Dylan Matson sat outside of the CEO's office waiting to be called in. He
tried to remain calm, but this was very difficult as he had never been
called into the big man's office before.
Dylan had just turned twenty-four and had been working for Wade
Industries for two years. He had been surprised that Wade had hired him
and even more surprised when he was assigned to the sales department.
Dylan had a degree in mechanical engineering from Purdue. However,
Howard Wade had long decided it was easier to train engineers to sell,
than it was to teach salesmen engineering.
Even though he was in sales, Dylan wasn't complaining, his base salary
was excellent, and he also earned a commission. His supervisor, Bill
McKenzie, had told him that all new engineers spent a few years in sales
before moving on to design.
In his two years at Wade, Dylan had not only made all his sales goals,
but had exceeded them. He wondered if this was the reason why Mr. Wade
wanted to see him.
Dylan casually glanced at his watch and saw that he had been waiting for
twenty-five minutes. Well, there was nothing he could do about that,
besides Bill knew where he was.
Mrs. Taylor, Howard Wade's secretary for twenty-seven years glanced at
the young man waiting to see her boss. She smiled slightly, wondering if
he knew what he was getting into. Like most secretaries, Mrs. Taylor
knew everything that was happening in the company. She ran her eyes over
Dylan. His personnel record said that he was six feet tall, but she
estimated him to be maybe five-ten. He was also thin, which made sense,
as if was all part of the reason why he was here.
His family lived in a Chicago suburb, and he had attended Purdue on a
full scholarship. She also knew that Dylan was single and wasn't
currently dating anyone. He had been dating a woman named Amy, who
worked for an airline. They had broken up four months ago. The reason
that Mrs. Taylor knew this was that she had read the special report that
Mr. Wade had ordered on the young man.
A red light flashed on her desk. "Mr. Wade will see you now," she
announced.
Dylan nodded. He noticed the strange smile on her face, as if she knew
something he didn't, and he wondered what it was.
Chapter 2
Dylan walked into Mr. Wade's office. He was struck by the fact that it
wasn't what he had expected. It was far from being lavish; instead, it
was sparse, but functional.
Mr. Wade sat behind an old oaken desk. It was large, but not
pretentious. Dylan had heard the stories of how Mr. Wade was still a
working design engineer.
The walls were real wood paneling. They were covered by the numerous
awards won by the company. There was one wall that had several mounted
fish on it, along with several photos of Mr. Wade with his fishing
partners. Dylan had heard that fishing was Mr. Wade's primary form of
relaxation.
"Please sit down, Dylan," said Mr. Wade. He pointed to a leather chair
sitting across from him.
Dylan sat down and waited for his boss to speak.
"I've been reading your performance reports; you've done very well,"
said Mr. Wade.
"Thank you, sir," replied Dylan.
"I'll get right to the point; I'm sure you're wondering why you're
here," stated Mr. Wade.
Dylan nodded.
"Have you heard of Connell Aviation?" asked Mr. Wade.
Dylan wasn't sure if this was a test or not, but he could tell that Mr.
Wade expected a response. He had taken it upon himself to learn
something about all the major contracts that Wade worked with. He had
also found an article on Connell online. "Yes, sir. They're a major
producer of private jets, catering to luxury personally designed
aircraft. We've been a provider of ventilation systems to them since
1969. They're due to start production on a new jet next year."
"I'm impressed," replied Mr. Wade. "Do you know anything about the CEO?"
"Savannah Connell, age 45, is the only surviving child of the company's
founder Harrison Connell. Her two brothers were both killed in flying
accidents. She owns a rather large estate in central New Jersey and has
the reputation of being somewhat of a recluse; at least, that's what the
article in Aviation Weekly said," stated Dylan.
"Savannah didn't get to be CEO just because she's the daughter of
Harrison Connell. She has degrees in aviation engineering in addition to
having an MBA from Stanford. She was also a highly skilled pilot," said
Mr. Wade.
Dylan looked confused. "Sir, what do you mean by was a pilot?"
"I guess you didn't read the entire article, she was involved in a crash
fifteen years ago and is now confined to wheelchair. From what I heard,
the accident would have killed most people. She was hospitalized for
over a year following the accident, and she found that, thanks to
computers and video links, she could run the company from her hospital
room. She took this to the next level when she left the hospital. Now,
she runs Connell Aviation from her home."
Dylan wondered what this had to do with him.
"Savannah does have her quirks. While she runs her company remotely, she
still insists on meeting all contractors face-to-face," continued Mr.
Wade. "Your name made the short list for presenting our contract to
Savannah."
Dylan's eyes lit up. This would be a major coup if he was selected.
"Now, I need to tell you, this task does have some rather 'unusual'
aspects to it," said Mr. Wade.
"Like what, sir?" asked Dylan.
Mr. Wade stood up and began to slowly walk towards Dylan. "I'm going to
tell you. Now, if you turn down this job, nothing else will be said. It
won't be held against you in any way."
Dylan wondered what his boss was talking about. "Okay."
"I'm also going to ask you to sign this before I go any further," said
Mr. Wade as he handed Dylan a form. "Read it and sign, please."
Dylan looked at the form. It was a privacy form stating that Dylan
agreed not to discuss anything he was about to be told. If he did, he
would subject to immediate termination from the company.
"I know this seems harsh, but Savannah insists on it," said Mr. Wade.
Dylan signed the form and handed it back to his boss.
"Okay, thank you, Dylan. Now, part of the reason why you made the list
for this job is the fact that you're one of our best young salesmen. You
also have the necessary engineering skills for the contract."
Dylan wondered what was coming.
"You also have the right body size," said Mr. Wade.
Chapter 3
"Right body size?" asked Dylan.
Mr. Wade nodded. "I said that Savannah has some 'quirks.' This will have
a major impact on your decision to take the job. Everyone who works on
her estate is a woman. This isn't by chance; Savannah only hires women
to work on her estate. This gender bias doesn't apply to her employees
at the Connell Aviation plant, but all males who want or need to set
foot on her estate must dress as a woman."
Dylan's mouth opened up. "You're kidding, right?"
Mr. Wade shook his head. "Nope. Savannah insists on it, and if a man
refuses to abide by her rules, they don't get on the estate. If they
don't get on the estate, they don't get a chance to present their
contracts to her."
"Why?" asked Dylan.
Mr. Wade shrugged his shoulders. "No one is sure. It may have something
to do with the fact that she doesn't trust men. The jet that crashed was
found to have some faulty components. The man who sold them to Connell
knew there was a problem and didn't say anything. Many companies now
only send female salespeople to see her."
"But a woman can lie just as well as a man," said Dylan.
"True, but I wouldn't say that to Savannah."
It took a few seconds for this to sink in. Dylan then looked at his
boss. "Um, does this mean what I think it does?'
Mr. Wade nodded. "We don't have a qualified woman to present our
contract to Savannah. If we did, you wouldn't be here right now."
"You mean I'd have to dress as a woman?' asked Dylan.
"Unfortunately, that's right. I promise that your privacy will be
protected," said Mr. Wade.
"I've never dressed as a woman before," stated Dylan immediately.
Mr. Wade smiled. "Dylan, we understand that. There's a service here that
will dress you and teach you what you need to know."
"How long would I have to do this? I mean, what are we talking about,
one day, two days?"
"If we get the contract, it could be weeks," said Mr. Wade.
"Several weeks?" asked Dylan.
"Maybe longer," said Mr. Wade. "You would be expected to stay there and
work out the details of the contract."
Dylan took a deep breath and let it out. "Wow."
"Like I said, if you don't want to take this job, I understand and
nothing will be held against you."
"May I think about it?" asked Dylan.
"Absolutely. Take the rest of the day off. Today's Friday, why don't you
take the whole weekend to deicide. Here's my private number, call me
when you make up your mind," said Mr. Wade. He handed Dylan his business
card.
"This is legit, right?" asked Dylan.
Mr. Wade nodded. "Just so you know, if you choose to accept this job, I
can assure you that you will be rewarded quite generously. However, I
don't want you to do this because you think that I'm bribing you."
"I understand. I'll call you no later than Monday, sir," said Dylan.
Mr. Wade smiled and extended his hand, which Dylan shook.
"Just so you know, two of our regional VPs had to dress in fem. I have
high opinions of both of them."
Dylan nodded and left the office. He now knew why Mrs. Taylor was
smiling.
Chapter 4
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 totally
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.
Chapter 5
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 to
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 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.
Chapter 6
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 was 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 in 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."
Chapter 7
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 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 afterwards, and he had to
admit that they had a pretty good time."
"Wait 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.
Chapter 8
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 fulltime 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, 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."
Chapter 9
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 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.
Chapter 10
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 not 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.
Chapter 11
"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. Afterwards, wash up and check
your makeup, we need to reapply your lipstick after eating anyway," said
Tess.
Dana stared back, but couldn't think 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.
Chapter 12
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 off at the
drycleaners, 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 couple 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 Lewis. 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
fulltime 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.
Chapter 13
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 having helped thousands of transgendered
clients over the years, she could sense that Dana was dealing with
something.
Chapter 14
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.
Chapter 15
"You did a nice job on your makeup this morning, Dana. In fact, I'm very
impressed with you entire appearance," noted Tess.
Tess was wearing a dark green blouse, 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, 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 on what it's like to be a business woman. 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."
Chapter 16
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.
Chapter 17
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."
Chapter 18
They sat together at a bar a few blocks from Tess's office. Lisa closed
her cell phone.
"Tess will be here shortly," said Lisa.
"What about, Jackie?" asked Dana as she picked up her glass and took a
sip of her Cosmopolitan.
Lisa shook her head. "She's off to be with her boyfriend, Chris."
"Wow, that's strong, do you drink these often?" asked Dana.
"They can take the edge off a long day," said Lisa, as she took a drink
of her own drink.
"So, you worked with Jackie before being hired by Tess?" asked Dana.
"Yes. We worked together," replied Lisa. "We didn't know each other that
well as we spent much of our time in cubicles. I got to know her as she
started her transition. We sort of bonded, and then she introduced me to
Tess; the rest you can say is history."
"That's incredible," said Dana. "Any regrets over leaving the corporate
world?"
"None at all," replied Lisa. "I like this job a lot more, and the money
is much better. I also don't have to deal with the office BS. Do you
want to work in an office your whole life?"
"No, I'm due to move out of sales soon, maybe even after this job, and
then I'll be assigned to an engineering department," replied Dana.
"Oooh, engineering, that's so exciting," said Lisa sarcastically.
"It is, I plan on modeling my career after Wally," added Dana, referring
to the Dilbert character.
"Good choice," replied Lisa with a laugh.
"Seriously, I enjoy designing things. I love the problem solving aspects
of the job," said Dana.
"What about other things? I mean, do you..., is there someone else in
your life?" asked Lisa.
"No, not right now, which is probably good. It makes things less
complicated," replied Dana.
"I see," replied Lisa. "Well, just so you know, work isn't everything."
"I know, but I still have a lot of loans to pay off from college. This
job could be just what my finances needed."
"What else do you want?" asked Lisa.
"Damn, you're nosey," replied Dana with a smile.
"Yep, it's one of my many flaws," replied Lisa.
"I don't plan on spending my whole life in an office, and work isn't the
only important thing in my life," replied Dana. She took another sip of
her drink.
"Okay, that was sufficiently vague," said Lisa. She winked at Dana.
"Point taken, I guess haven't planned out my life too much so far."
"That's good, because if you plan out things too far in advance, you may
miss some interesting opportunities that life throws at you. I mean,
look at me; this wasn't what I thought I'd be doing," said Lisa.
Tess walked over and took the stool next to Lisa. She picked up one of
the near empty glasses and examined the contents. "Well, I see you two
have been busy."
"I'm teaching Dana how to drink like a businesswoman," explained Lisa.
Tess laughed. "Well, do you want another round?"
Dana and Lisa nodded.
Twenty minutes later, a group of businessmen walked into the bar. One of
them looked over at Lisa and smiled.
"I'll be damned. What are you up to, Lisa?" he asked.
"Hi, Mark, how're things at Chambers?" asked Lisa.
"Hectic as always," he replied. "So where do you work now? We were
surprised you left; I mean, we all thought you were on the fast track to
the top."
Mark was in his late twenties and had dark brown hair. He was in good
shape, and had a rather high opinion of himself when it came to women.
He had asked Lisa out several times, and after she kept turning him down
he assumed she was a lesbian, although he never would say this to her
face. Lisa always thought of him as being slightly annoying, but
harmless.
"I got a better offer; I now work for a personal consulting firm," she
replied. "I like the more flexible hours."
Tess turned to Dana and winked. Dana did her best not to giggle.
"Well, that sounds interesting," replied Mark. He looked over at Tess
and Dana. "So, how about introducing me to your friends?"
Lisa made the introductions, introducing Dana as a friend from out of
town.
Dana couldn't help but notice the way he ran his eyes over her. "Pleased
to meet you; so where are you from?"
"Detroit," Dana lied.
"So what brings you out here?" he asked as he moved closer to her.
"I have some business up in Seattle. I came down here to have dinner
with Lisa and Tess," answered Dana.
"Oh... well, maybe if you're free another night, we can do dinner; would
you like that?" he asked. He handed her his business card. "Here's my
number."
She took the card and stared at it. "Thanks, but I have a rather full
agenda this week," replied Dana. She felt that strange feeling run
through her body again. It was the same feeling she had felt when Pete
had looked at her the previous night.
"Well, you can't blame a guy for asking," he replied with a grin on his
face. "Well, good seeing you again, Lisa. Nice meeting you, Tess, and,
Dana, if you change your mind, give me a call."
He then walked over to join his friends. He glanced over at Dana again
and shrugged his shoulders; why did the good looking business women
always turn out to be lesbians? he thought. He figured that any woman
who turned him down had to be a lesbian.
Lisa and Tess leaned over towards a much relieved Dana.
"You passed another test - with flying colors, I must say," stated Tess.
"Yes, you passed on the 'blowing off the sexist jerk in a bar' test,"
added Lisa. She held up her glass in a toast.
"Was he really trying to pick up on me?" whispered Dana.
"Oh, yes," answered Lisa nodding. "He's actually not that bad, but he's
not my type."
"Nor mine!" interjected Dana. "Hey, I'm all for trying new things, but
not that!" She lifted up her glass and touched those of Tess and Lisa
and took a long sip.
"It's okay, Dana, it happens a lot to our clients," continued Lisa.
"Consider it a sign that you're doing a great job."
Chapter 19
Back at her apartment, Dana thought about the encounter at the bar. She
looked at herself in the mirror and could see that she was really a
male, but could others? Was Mark really fooled, and did he see her as a
woman?
This was becoming more complicated than she had ever thought it could
be. She knew that there had been no chance that she would have accepted
Mark's offer, but what if something like this happened on the trip?
She thought about that Halloween night back at college. When it had
happened, she had convinced herself that it was just a one time thing,
that she had been drunk, and that it would never happen again. Yet, she
had felt those... those feelings, twice since she had become Dana, and
neither time was she drunk. She knew that she would have to be on guard
at all times from now on.
Meanwhile, Lisa and Tess were discussing Dana over dinner at Lisa's
house. It was takeout Chinese, and they were sitting on the couch
passing around the boxes.
"I agree with you, Tess; this can't be the first time that Dana's
dressed," said Lisa. "If it is, she's the most relaxed client that we'll
ever have."
"Did you see the way she reacted to Mark back in the bar?" asked Tess.
"Yes," replied Lisa. "She's definitely fighting some feelings."
"I'm torn right now, Lisa. I don't like to interject my feelings about
clients without them first bringing it up, but it's obvious that Dana is
dealing with some gender issues," said Tess. "Don't get me wrong; as you
know, I have nothing against her if she is transgendered, but I hate to
see someone in denial."
"I know. Granted, I don't have as much experience in these sorts of
things, but if Dana is a straight male who's content with his gender,
then I'm June Cleaver."
Tess smiled. "No one would ever, not in a million years, confuse you
with her. By the way, when are you going to let me teach you how to use
chopsticks? I hate to see you use a fork."
Lisa laughed. She had a bit of wild side and had shared some of her
adventures with her co-workers.
"I've tried before and usually end up with more food on my lap than in
my mouth," replied Lisa.
Tess then reached into her bowl with her chopsticks and pulled out a
small piece of Kung Pao chicken, held it out in front of her and then
ate it.
"Show off! Well, maybe we should have Jackie join us some night; maybe
if Dana talked with her, she'd be more likely to open up. What do you
think?" asked Lisa.
"Maybe," replied Tess. "I just don't want her to get hurt. I mean, this
is different than one of our usual clients. Dana didn't come to us on
her own accord; she was picked by her boss because of her experience and
body shape. It's different when we get a crossdresser who turns out to
be a transsexual."
"That's true," said Lisa.
"A couple of years ago, we had another Wade salesperson named Larry
Hill; I had the same feelings about him," stated Tess.
"What happened to him?"
"She's still working for Wade as Leslie Hill. She wrote me last year
when she was recovering from her SRS. Mr. Wade told me that she's now a
VP," explained Tess.
"As long as she's happy, what does it matter?" asked Lisa.
"Hey, you don't have to convince me, but I hate to see someone struggle
with their identity. What if I'm wrong and say something to Dana?"
"Do you really think you're wrong?" asked Lisa.
Tess shook her head as she ate. "I have something I want to try."
Chapter 20
The next couple of days passed quickly. Under Tess and Lisa's watchful
gaze, Dana practiced her dressing and makeup.
"I'd like take you out to dinner Friday evening. It'll give you an
opportunity to dress up and practice your evening makeup," said Tess.
"That sounds good," replied Dana. "Will it just be us?"
"Yes, Lisa has a date that evening," replied Tess. "Now, you'll be on
your own for the weekend, but Monday, I'm going to have Jackie go out
with you."
"Sure, that sounds okay," replied Dana. "I have to study this weekend
anyway. I want my presentation to be perfect."
"Don't over study," said Tess. "Try to relax too."
"I was thinking of going to the movies one night," said Dana.
"Good. Now, do you want to meet here, or do you want me to pick you up
this evening?" asked Tess.
"Why don't you come by my place? That way, you can grade my appearance
before we go out, and also make any corrections," said Dana.
"I want you to wear the black dress tonight; let's keep it simple," said
Tess.
Dana then discussed accessories to go with the outfit. Tess was
impressed.
"You've been studying," said Tess.
"Well, you told me to look at other women, and I have. I also have those
fashion magazines that Lisa gave me," said Dana.
"I can see why you were picked for this job," said Tess.
Dana smiled back. "Thanks."
"I want you to try wearing stockings tonight," said Tess. "It'll be a
good learning experience for you."
Chapter 21
Dana sat on the edge of her bed and slowly pulled a stocking up her left
leg. She had already ruined one, and was determined not to repeat the
mistake. When it was near the top, she stood up and attached the
garters. In some ways, she was sort of surprised that women still wore
stockings. Most of the women that Dana had dated as Dylan wore
pantyhose.
She stood up and examined herself in the mirror. The stocking looked
straight, and then she noticed a mistake - she had her panties on under
the garters. That would make going to the bathroom rather difficult, she
thought.
It took her a few minutes to correct this error. Dana smiled and knew
she'd have to tell Tess of the mistake. She then finished getting
dressed.
Her dress was a simple short, black sleeveless number with a matching
jacket. Dana remembered how Tess and Lisa had told her how it could be
easily adapted to look either formal or casual.
A short time later, Dana was applying her makeup. Eyeliner was still a
problem, as Dana either applied too much or not enough. However, this
evening she seemed to apply just enough.
Pleased with this, she worked on her mascara. It also looked pretty
good. Dana shook her head at the fact that she was becoming pretty
proficient at putting on makeup.
Dana finished just a few minutes before Tess arrived.
After she let Tess in, Dana stood in front of her and smiled. "Well?"
Tess ran her eyes over her student and nodded. "Very good, Dana. You're
definitely the fastest learning pupil that I've had in a long time."
Tess was also wearing a black dress.
"Okay, one last thing, you need to put on some perfume," explained Tess.
"Now at work, you should be careful about using scents, as too much can
be really annoying to others, but for evening you can be more creative,"
said Tess. "Here's a scent that I think will suit you."
Dana sniffed the bottle and nodded. "Not too bad."
"Now, don't soak yourself in it, just a few drops will do," explained
Tess.
Dana did as she was told. "How's that?"
"Perfect, now let's go out," said Tess.
Chapter 22
They arrived at the restaurant and were shown immediately to their
table. It was an upscale place that was rated as one of the best in the
area.
"How'd you get reservations for this place? I tried once for a date and
was told it would be a three week wait, and that was just for a
weeknight," whispered Dana.
Tess glanced around and then motioned Dana to lean closer. "The head
chef is a client."
Dana cocked her head. "You're kidding, right?"
Tess shook her head. "I only use our relationship for very special
events."
"I'm honored," replied Dana.
"Well, you've done so well this week, I figured you could use a little
celebrating," replied Tess. "Besides, I love the lamb here."
Dana laughed.
"I also want you to know that I now consider you a friend," continued
Tess.
"Thank you, I really appreciate that," said Dana.
"I don't do this for all my clients. Granted, I get to pick and choose
who I help, so I can afford to drop the ones that creep me out, but I've
also made some wonderful friends through my job."
"Like Lisa and Jackie," said Dana.
"Exactly. You'll be spending a lot of time with Jackie next week, and I
just know that you'll get along famously. I'm a good judge of
character," stated Tess as she began to scan the menu.
Dana picked up her menu. "I've only talked to her a few times, but she
seems really nice."
"She's very sweet. I brought her in initially to be my receptionist and
assistant, but I want to move her up to working with clients too," said
Tess.
"From what Lisa said, Jackie was on the fast track at her old company.
I'm surprised that she'd take a position as a receptionist," said Dana.
"Jackie needed a big change. She had been hiding her feelings for so
long, and when they came out, there was no way she could have stayed at
her old job, even though her boss was supportive. She needed a position
with less stress, as she had enough to deal with her transition."
"But I thought her transition was going smoothly," said Dana.
"Oh, it is, but there's no such thing as an easy transition, even when
you know it's the right thing to do. I'm just happy to provide her with
a job that allows her to bloom," said Tess.
Dana nodded.
During dinner Dana didn't say much, as if she was lost in her thoughts.
"Is everything okay?' asked Tess.
"Oh, my halibut is wonderful," replied Dana.
"Then what's up?" asked Tess.
Dana sighed. "May I talk to you after dinner about it?"
Tess nodded.
"Thank you," replied Dana.
Chapter 23
They drove back to Dana's place after dinner.
"Would you like some coffee or tea?" asked Dana.
"What are you having?" asked Tess.
"Brandy," replied Dana.
"That sounds good," replied Tess as she sat down.
Dana poured two glasses and handed one to Tess. She then sat down next
to Tess and took a sip.
"I don't know where to start," said Dana.
"How about wherever you feel comfortable?" replied Tess.
"Okay," said Dana. "I feel really comfortable as Dana. I never really
thought about this sort of thing, but the last week I've felt so
relaxed."
"I've noticed," replied Tess as she took a drink. "Ohhh, this is really
nice."
Dana nodded. "I lied when I said that I never actually dressed before...
I did it twice before."
"Tell me about it," said Tess.
"The first time was in high school. I dressed up for a costume party;
actually, my sisters dressed me up."
"Did you even think about dressing up in women's clothes?"
"A few times, it was very confusing, and I did my best to fight off the
feelings," confessed Dana. "I was expected to excel in school, and being
different wasn't part of the program."
"I see, so you were an overachiever?" asked Tess.
"I graduated from Purdue in less than four years; what does that tell
you?" asked Dana as she took another sip of her brandy.
"Point taken, let's get back to Halloween, what did you wear?"
"My sister's cheerleader uniform," replied Dana. "I looked really good,
almost too good. My sisters kidded me that I should try out for the team
the following year. At the party, I fooled a lot of people. I ended up
winning the top prize."
"So, it was their idea?" asked Tess.
"Yes, but I didn't put up much of an argument. They had been kidding me
for years that I would make a cute girl, and when they suggested that
they turn me into a cheerleader, I readily agreed."
"Anything else happen?"
Dana shook her head. "Well, that's not true; I got a date with one of
the cheerleaders out of the deal."
Tess laughed.
A smile broke out on Dana's face. "It turned out that I lost my
virginity to her."
"Can I ask you a question about that?" asked Tess.
Dana nodded.
"How did it happen? I mean who instigated it?"
Dana cocked her head, and then it hit it. "She did. Wow, I never really
thought about that, but she took charge."
"Did she dress you up; I mean, in girl's clothes?"
Dana looked shocked. "How... how did you know?"
"It's not that uncommon," replied Tess.
"She just put a bra and panties on me. Oh, she also put lipstick on me,"
said Dana. "Wow, I totally forgot about that."
"What about the next time?"
Dana took another long sip and almost emptied her glass.
Tess reached over and put her hand on Dana's shoulder. "You don't have
to tell me."
Dana shook her head. "No, I want to - I need to." She reached over and
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