The Saleswoman
Belladonna
[Author's Note: Based on a cap by Commentator]
The sound of a phone ringing turned Portia Dawn's head. She reached for
the phone and picked it up as she saw her secretary's name appear on the
caller identification panel.
"Yes, Maria," Portia answered.
The woman on the other end hesitated before she replied, "Jeff just
stepped into his office."
"Thank you, Maria," Portia replied while she felt a sinking feeling in
her stomach as she hung up the phone.
Portia stared blankly at the top of her cluttered desk. She tried to
think about how she would phrase the news she was going to break to
Jeff. She was certain it would be the most unpleasant conversation she
had to take part in since she was elevated to a management position.
Portia leaned back in her chair while she pondered about how she would
tell her top salesman that he was no longer going to fit into the
company's plans. While she had terminated people before, that was job
related performance. There was nothing about Jeff's performance,
however, that indicated that he should be reassigned or fired.
The exemplary performance of her underling made the coming conversation
seem especially cruel to her. If all of the company's salespeople
across the world had been as successful as Jeff, the conversation would
not even be necessary.
She lifted her head up and sighed as she picked up the phone and dialed
Jeff's extension. Jeff picked up his line and answered, "What's going
on, Portia?"
"Can you come into my office for a moment?" Portia replied.
"Sure," Jeff responded before he hung up.
Portia hung up her phone and tapped her fingertips against her desktop
while she waited for Jeff to enter her office. As Jeff emerged through
her doorway, Portia looked up at Jeff. She flashed him a faint smile as
she said, "Can you please close the door?"
Jeff found the request strange. He felt nervous while he closed the
door behind him and turned towards Portia. Portia told him to take a
seat.
Jeff's heart started to race as he wondered if he was being terminated.
While he knew he was the top performer in the office, he was also aware
that the company's international corporate parent's operating account
was running in the red.
Portia took a deep breath before she said, "Jeff, as you know, there's
been some financial difficulties with the company, none that are your
fault. If we only had a few dozen clones of you selling our clothes
around the world, we'd be set."
Portia's resigned tone and nervous laugh was almost as unsettling as her
words to Jeff. After a pause, Jeff steeled himself and asked, "Are you
letting me go?"
Portia's eyes widened while she shook her head and said, "No. It's
nothing like that. It's just that there are going to be some changes
made."
"Like what?"
"We're discontinuing our clothing lines directed at men. They're just
not selling."
'Maybe if you designed clothes that men actually want to wear and not
what their wives want them to wear,' Jeff thought as he nodded and
looked down at the clothing from the line that he was wearing. Jeff had
taken grief for it from friends who had seen him in the form fitting
clothing that he was marketing.
Portia paused before she continued, "As you know, all of our salespeople
are required to wear the company's line when they're selling it. We
want to put it right out there in the open, you know."
"Oh, I know," Jeff replied as he touched his too tight fitting slacks
that compressed his manhood.
"I guess our company is just too affiliated with women to the public to
really sell guy's stuff."
'Yes, that's it,' Jeff thought before wondering if Portia could read his
sarcastic thoughts based on the expression on his face that her words
had wrought.
Portia then continued, "So, given all this, we've decided to offer you
another position in the company. It doesn't pay as well because you
won't be making commission, but..."
"Why can't I stay a salesman? I'm the best one you've got!" Jeff
forcefully interjected.
"That's totally true, but we're just selling women's wear."
"So what? I've been selling it for ten years, and I sold more of it
this year than anybody in the American division."
"Yes, but we're only selling WOMEN's wear, now," Portia replied,
emphasizing the gender the company's clothing was geared towards.
"You think I can't sell it? That's so sexist! It's the majority of my
sales."
"All true, but you don't have the clothes to model our line," Portia
replied, hoping that Jeff would finally take her hints.
Jeff dismissed her claim noting, "That policy has to go. I'm not the
only salesman you got."
"We're letting go of some of them."
"That's totally sexist. It's discriminatory."
"It's not discriminatory. You can't model the line."
"The hell I can't," Jeff retorted as he began to stroke his mustache.
Portia's eyes widened before she grinned and said, "You think you could
pull off one of our dresses?"
"I can pull it off. That's my sales shtick, right there! If a man can
look this good in it, what about you? You know, the whole Namath in
pantyhose hook."
"I'm sorry. We just can't do it," Portia replied before Jeff got to his
feet and said, "I'm not going to let you guys get away with this."
Portia gave Jeff a nervous look before he exited the room. As Jeff
stepped out of her office, Portia picked up the phone and called the
company's human resources director to advise him about what had
transpired.
The human resources director explained that Jeff could sue the company
for gender discrimination. Portia nodded as the man explained that they
could not bar Jeff from being a salesman for the company due to his
gender.
"But what about the policy?"
"That's not a problem," the director replied.
"How can that be?"
"It's a gender neutral policy. It doesn't say that only women can wear
the women's line. He's just chosen to wear the men's line so far. Now,
that it's being discontinued, he can choose to wear whatever he wants
from the women's line or take another position," the director explained.
"You think that would hold up in court?"
"Based on precedent, it's, at least, got a shot."
Portia nodded before she thanked the man and hung up her phone. She
called over to Jeff's office and asked if he could return to her office.
Portia could sense that Jeff was angry as he answered, but he agreed to
see her in her office. Portia had Jeff close the door again before she
said, "Good news! I just cleared it with HR, and they agreed that you
have every right to continue working here as a salesman."
"Thank you," Jeff replied as he threw up his hands before he smiled.
"Just as long as you keep wearing one of our active lines," Portia added
with a sheepish look.
Jeff gave Portia a blank look, almost in disbelief that she was trying
to hold him to his earlier bluster. Portia smiled while she added, "We
need to really make you over though so that you don't look like a total
fool in our clothes though."
Jeff shook his head before he replied, "That can't work. I'm always
going to look like a guy. There's just no way around that. They didn't
put Namath in makeup. Nobody would have bought it. Just pantyhose.
Just pantyhose!"
"Yes, but he was famous. We're talking about you going to meet with
people who don't know you."
"But I have an established network of merchants. They know me!"
"They might not recognize you from a distance, but when they see how
good you look in one of our skirts, they're going to be blown away. We
could pull your hair out of that ponytail and let it rest on one our
blouses and let them imagine how good they'll look."
Jeff could not tell if Portia was being serious or not. He shook his
head again as he said, "If I try to fool these people, they're going to
be pissed. It's going to turn them off on me."
"Some, maybe, but others will love it."
"I know that some are going to hate it. That's why, the more I think
about it, the policy should just be changed. Whom are you really
excepting from it? There's only two other salesmen in this department,
the rest are girls."
"But if we make exceptions for the men, then we're discriminating
against the girls and the whole policy has to go. We'd lose a big part
of our marketing if the girls weren't dressed in the line. You have to
understand our position."
"It's just crazy!"
"No. It's a great strategy. If you look believable before making the
reveal or, if you know them, coming up close to let them check out this
transformation, it'll be amazing. It'll be a real showing of how the
clothes make the man. Think about it. The metamorphosis of plain old
Jeff into this smartly dressed lady. It'll really make them think."
Portia's words seemed absurd to Jeff, but he figured that he had to
either accept the terms and preserve a potential lawsuit or take a lower
paying position in the company. Never being one to shy away from a
challenge, Jeff decided to put Portia on the defensive.
Jeff put his hands on his hips and said, "You got yourself a deal."
Portia's leaned back in her chair, surprised that Jeff was actually
willing to go through with what he had seemed to propose out of anger.
Portia tapped on her chin while she looked him over and wondered about
how to make Jeff show her he was serious.
A smile came to Portia's face before she said, "Okay. Are you going to
handle your beautification process or do you want some help?"
Jeff gave Portia a confused look before Portia added, "In another words,
do you want some help making you over?"
Jeff squirmed for a moment before he nodded his head, sure that making
the company assist in his feminization would help him in the long haul,
one way or another. Portia nodded in response before she picked up the
phone and called a saleswoman into her office.
Jeff gave Portia an inquisitive look as she hung up the phone.
"Ariana used to be a stylist," Portia responded to Jeff's expression.
Jeff's stomach sank as he realized how serious the situation was quickly
turning. He knew that he had to back out or Portia was going to make
him live up to his words. Jeff shook his head before he said, "Do we
really have to let her know about this?"
"Did you think she wouldn't figure it out when you show up here in a
blouse and thigh highs?" Portia asked with raised eyebrows.
Jeff shook his head, realizing that any attempts to hide his future
cross-dressing were absurd, since it would be impossible to hide in
short order. Seconds later, Ariana entered the room.
She greeted Jeff warmly before she asked Portia what was need from her.
Portia responded by advising her as to what had transpired with Jeff
given the company's decision to discontinue its male clothing line.
Ariana struggled not to laugh before she looked at Jeff's blushing face
and blurted, "You're serious about this?"
Jeff nodded.
Ariana gave him a disbelieving look before she said, "Wow."
"What would you do?" Jeff countered.
"If I was you, I'd take the lower paying job."
"I deserve to keep the job I have!"
"I didn't say you didn't, but you're getting to get killed over this."
'All part of a lawsuit,' Jeff thought before he shook his head and said,
"I'm sure the company would not allow a hostile work environment given
that it's the company's stupid policies that have put me in this
position."
"Yes, but soon it's only going to be gay men wanting to put you in any
sort of position, and it'll probably be at the bottom of the missionary
position," Ariana joked.
"Ariana!" Portia shrieked while Jeff blushed.
"I'm so sorry. I couldn't help myself."
Jeff rolled his eyes before Ariana said, "I would be happy to help."
Portia nodded before she told Ariana and Jeff to come to her house on
Saturday for his makeover. Ariana smiled as she exited Portia's office,
leaving Portia to take Jeff to get measured for his new wardrobe.
Jeff felt foolish while he followed Portia to see the company's in house
seamstress who worked in the building's ground floor boutique. The
seamstress smiled as she listened to Jeff's predicament before she told
Jeff to untuck his shirt.
Jeff followed her direction and lifted his shirt so that the woman could
measure his waist at its narrowest point. She wrote down the
measurement before she told Jeff to remove the shirt.
Jeff unbuttoned the shirt and placed it on the chair before he removed
his undershirt. She went to measure his chest and turned towards Portia
and said, "How am I going to do this?"
"What cup size do you think Jeff would have on that build?"
"It's a pretty thick build. It'd say a C-cup, minimum."
"Just add that to the measurement," Portia replied with a smile.
The woman nodded as she took and adjusted Jeff's chest measurement
before she measured the distance between his neck and his waist down his
spine. The seamstress wrote down Jeff's measurements before she said,
"Jeff, I need you to take off your pants."
Jeff hesitated as he glanced over at Portia. Taking the hint, Portia
promptly excused herself from the room in response. As she stepped out
of the room, Jeff lowered his pants before he stepped onto a pedestal
for the woman, dressed only in his briefs.
The seamstress proceeded to take Jeff's hip measurements before
measuring the length from his waist to the floor.
"Only two more measurements left," the seamstress said to Jeff's relief.
Jeff watched as the woman moved towards him and said, "I'm going to take
your inseam now."
Jeff nodded as the woman bent down at her knees and measured from his
crotch to the floor. She smiled at Jeff as she said, "You've got long
legs for a girl."
"Typically happens when you're a boy," Jeff countered.
"Not in all cases," she replied.
Jeff wondered how she knew that before she told Jeff to take a seat.
"What for?" Jeff answered.
"I need to measure your crotch depth."
"Crotch depth?"
"Yes, you sit down and I measure you from the seat to your waist."
Jeff nodded, feeling strange to have such a measurement taken on his
side. As the seamstress finished, she said, "There we are. All done.
Was that so hard?"
"No. I don't think this is the hard part though," Jeff replied with his
nervousness making itself known in his tone.
As Jeff redressed, Portia was called back into the room by the
seamstress. Portia smiled as she asked the woman, "So, what do we have
in his size?"
"We've got plenty to choose from," the seamstress replied, while Jeff
began to worry about what she was going to pick out for him.
The smile stayed on Portia's face as she nodded and turned towards Jeff
and said, "You don't have to wait around with us girls. I'll bring your
new work clothes over to my home for you to pickup on Saturday."
Jeff gave her a nervous nod before he exited the room, feeling as if his
stomach was tied up in knots.
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As Jeff left his home on Saturday morning, he looked around his
neighborhood and wondered if he could ever show his face among his
neighbors again if they ever caught wind of what he was going to be
doing at work. The thought of others, who did not understand the basis
for his decision, seeing his feminized state filled Jeff with fear about
their potential reactions.
Those fears stayed with Jeff while he made his way towards Portia's
home. He wondered if he should just accept her alternative offer of a
new position. He knew that it would be the easier way, but it would not
satisfy his competitive urges that were only stoked further by his
unrivaled success at his job.
Shortly after Jeff parked his car in front of Portia's home, he took a
few deep breaths and walked up to her door and rang her doorbell. Jeff
stood in silence, waiting to greet his boss while he sucked in his lips.
Portia drew the door open and greeted Jeff dressed in a two-toned white
and black dress with a flared out, above the knee, pleated skirt and a
plunging v-neckline. Jeff's eyes were instantly drawn to her ample
cleavage that was framed by the neckline before he realized how
inappropriate his leering was.
'Is she setting me up?' Jeff wondered as he thought that Portia might
be trying to find a pretext reason to fire him.
Portia stared at Jeff for a second before she shook her head and said,
"You didn't shave."
"Was I supposed to?"
"Did you really think the mustache would work?" Portia asked as she
raised her arched eyebrows.
"It's my calling card," Jeff retorted.
"Well, it'll make you look silly in a dress. You can't go with the
Freddie Mercury look in garters, Jeff."
"God knows, Freddie did it."
"If Freddie Mercury had an orgy with 80 men, would you..."
"Okay, I get the picture. I'll shave. I'll shave," Jeff replied with
haste, uncomfortable with where their conversation was heading.
Portia grinned before she led him into her home. Jeff looked around her
house as he entered it. He had been there only twice before for two
parties Portia had thrown since joining the company.
Jeff's eyes followed Portia's long legs as she strolled in front of him
with a wiggle in her walk as her 4-inch heels clicked on the floor.
Portia came to a stop in her kitchen before Jeff caught sight of Ariana.
Ariana did a double take as she saw the hair on Jeff's lip before she
said, "You're still rocking the porn star look?"
"If he wants to still look like a porn star, I think I should have
gotten him bigger breasts," Portia added as she pivoted towards Jeff.
Jeff rolled his eyes at her before he said, "So, what's the game plan,
girls?"
"Game plan? Why that's a masculine term if I ever heard one for what
we're about to do," Portia replied with a laugh.
"What would you call it?" Jeff asked.
"An itinerary."
"An itinerary for what?" Jeff countered.
"For your journey to feminization and self realization," Ariana added
with mock seriousness.
"So, is this a self help seminar?" Jeff inquired with a nervous smile.
"Well, you do seem to think your helping yourself by going through with
this instead of taking my offer, which, by the way, still stands."
Jeff stared at Portia, wondering if he should back out while he still
had time. His competitive urges told him, however, that he would be
miserable if he took the incentive out of his work life.
"No. I come to play," Jeff returned.
"Again, with the sports metaphors," Portia replied, shaking her head.
"He should get them all out because pretty soon no one's going to take
his comments regarding sports seriously," Ariana said with a grin while
she moved towards him, carrying the chair she had been sitting on.
"Take a seat," Portia said to Jeff while Ariana put the chair down.
Jeff hesitated for a second before he sat down. Once he sat, Ariana
began to run her fingers through his hair.
"You've got thick hair," Ariana said.
"So I've been told."
"It's great. I don't think you'll ever go bald with hair this thick."
"I've been told that too."
"So, what are we doing with it?" Ariana inquired.
"Surprise me," Portia answered for Jeff.
"Surprise you?" Jeff replied.
"Well, it'll be a surprise for you too."
"Wait a second," Jeff retorted.
"What?" Ariana interjected.
"Do I get a say in this?"
"Somewhat," Portia answered before explaining, "You do have to give off
a professional female appearance when you're wearing our line."
"Can't it be something on the androgynous side?"
"Androgynous, I think I can come up with something that could work so
that you can play both sides of the fence," Ariana replied.
Jeff felt relieved by her statement before Ariana added, "But these
colors will just have to go."
"What?"
"Girls don't keep their hair all one color anymore. You need some
highlights. Nothing crazy, just enough to make your look pop."
"Pop?"
"Yes, give it that wow factor when you saunter into a room in a dress
and all the boys turn to check you out," Ariana said with a giggle.
Jeff cringed at the thought, prompting Portia to remind him, "You can
still back out. No one will think you're any less of a man for not
getting a makeover."
Jeff shook his head, figuring that he could persevere through it and
either succeed under the terms of his employment or make significant
money from a lawsuit for gender discrimination. Portia gave him an
incredulous look before she said, "I guess we should get started then."
Ariana nodded before Jeff inquired, "Are highlights really necessary?"
"Well, all girls have them, these days, unless they're bleached blonde.
Would you prefer that?"
Jeff shook his head rapidly from side to side, thinking about how bimbo
like girls with that hair color struck him. Ariana smiled as she
replied, "I didn't think so."
Portia and Jeff watched as Ariana walked away from him and put on
gloves. As she began to prepare the mixture she was going to use to
highlight his hair, Jeff gave her a curious look and inquired, "Aren't
you going to wash my hair first?"
"Oh, no. That's an amateur mistake," Ariana retorted, before adding,
"Washing gets rid of the natural oil in your hair that protects it from
the damaging effects of the dye."
After she finished mixing the dye, Ariana walked over to Jeff with a
clear cap in her hands that Jeff thought looked like a shower cap.
"What's that for?" Jeff inquired.
"It's to help control where the dye goes," Ariana replied as she put it
over Jeff's head. Portia struggled not to laugh as she saw her male
employee having strands of his shoulder length hair pulled through the
holes of the cap with a hook.
'I can't believe he's doing this,' Portia thought, shaking her head.
The bemused look on Portia's face made Jeff blush as he realized how
foolish he must have looked given how stupid he felt.
As Ariana approached him carrying the solution and the applicator brush,
she said, "One last chance to back out."
Portia crossed her arms and gave him an inquiring look as she bent to
make her long, slender legs look longer, hoping that his masculine urges
would make him reject his impeding feminization. Jeff shook his head
and said, "Let's do this."
Ariana shrugged as she said, "Never thought I'd be doing this to a boy."
Jeff blushed at her comment as Ariana began to work from the front to
the back of his head, carefully giving each strand of hair an even
coating of the highlighter agent. As Ariana worked in silence, Jeff
inquired, "Is there any method to this madness?"
"Yup."
"Can you elaborate?" Jeff retorted with a slight smile.
"I'm working from front to back so that your front hairs will have more
time to lighten. You may not notice it, but your hair is naturally
lighter in the front than in the back, to one degree or another."
"Oh," Jeff replied as the strong scent of the dye lingered in his nose.
Once Ariana finished applying the highlights, she took hold of another
item that struck Jeff as looking like a shower cap. Ariana put it on
over his head and said, "We're just going to let that sit for twenty
minutes and then we'll wash it out and move onto the next thing."
Jeff nodded before he began to make small talk with Ariana and Portia
about potential leads at work and the corporate restructuring of the
company's parent corporation. Jeff could tell that Portia had slight
fear that she was going to lose her job due to the falling sales
worldwide. Ariana too was nervous.
'Maybe I should have gotten out when I could?' Jeff thought while he
felt the cap still pressing into his head.
After twenty minutes, had passed, Ariana told Jeff to follow her to the
sink. She removed the shower cap and washed out Jeff's hair that was
coming through the second cap as he bent over the kitchen sink. The
feeling of her hands running through the strands of his long hair and
massaging the solution to remove the dye felt strange to Jeff.
Satisfied that the dye was washed out, Ariana removed the second cap and
pushed his head back under the water. The sensations from her massaging
his scalp and washing his hair with a shampoo and conditioner for color
treated hair made Jeff feel good before she turned off the water.
Once she finished patting his hair with the towel, Ariana sat him back
down on the chair and placed an apron around him.
Portia shook her head as she saw the highlights on her male employee's
head. She knew that he was going through with it at that point and
thought, 'Well, he's in for a penny, he's in for a pound,' before she
said, "Girls, I'm going to get Jeff's new clothes."
"Okay," Ariana said as she began to examine his hair again.
"Girls?" Jeff said to Ariana.
"Yes, you're one of us, now. Welcome to the sisterhood, Jeffwina,"
Ariana said with a laugh before she lightly patted his shoulder.
Ariana then began to brush out and clip Jeff's hair to section it off
before she began to make the first cuts. Jeff felt somewhat defeated as
he watched the first strands of his highlighted hair falling onto the
apron he was wearing. The sight of the coloring of the highlights
alarmed him as he wondered what he had to look like.
After the first few cuts, Jeff asked, "Can I see a mirror?"
"Not until I'm done," Ariana replied before Portia walked into the room
carrying several shopping bags filled with the company's ladies' wear
line.
The sight of Jeff with purple hair clips in his highlighted hair made
Portia want to laugh, but she restrained herself, knowing that it would
do her no favors if Jeff decided to publicize what he was going through
at anytime. As Portia stifled herself, Ariana continued to work on
Jeff's hair as if she was cutting any other woman's hair she had worked
on over the years before she started to work at the company.
She moved around Jeff to view him from different angles while she
layered his thick hair before she asked Portia, "Do you think we should
give him a permanent wave."
"I don't like the sound of that," Jeff retorted.
"It's not really permanent," Ariana countered.
"Still don't like it," Jeff replied.
"Well, I think it would help soften your look. The cut is doing that
for you too."
"How?" Jeff inquired, worried about the implications of what she was
suggesting.
"They're softening your facial angles and really framing your face
better."
"You do have a pretty face," Portia added with a grin.
"I'm so sure," Jeff replied.
"Well, not drop dead gorgeous, but okay," Portia replied.
"I doubt I'm even that good."
"I think you might be a solid 5 when all is said and done," Ariana
responded with a straight face.
"You're too kind," Jeff replied, emotionless as Portia started to laugh.
Ariana continued to work on his hair before she took out a blow dryer
and plugged it in. Jeff sat still while Ariana moved around his body,
blow-drying his hair while simultaneously brushing it out as she gave
him tips while she did so.
Portia's eyes widened as she watched the look of the hairstyle taking
shape around Jeff's face. 'This might actually work,' Portia found
herself thinking in almost disbelief.
Ariana nodded as she put down the blow dryer and asked Portia, "What do
you think?"
"I think you're a miracle worker."
"I do what I can."
"Yes, you'll be doing my hair from now on," Portia said.
"Is that an order?" Ariana asked with a laugh.
"Sure is," Portia replied with a grin.
"Can I see it now?" Jeff interjected, growing anxious.
"Not yet," Portia said.
"When?"
"When I think you're good and ready," Portia answered.
Jeff pouted for a second before Ariana removed her tweezers. Jeff gave
them a nervous look before Ariana said, "Relax. I'm just going to clean
up your eyebrows, not turn them into two dainty, little arches."
Ariana's words relieved Jeff's worst worries. While he knew that his
hair was an easy enough fix by simply shaving it off or cutting it down
and dying it one color, he knew that he would have to wait for his
eyebrows to grow back in.
Jeff thought it would hurt more when Ariana began to pluck his eyebrows,
but it never made him wince as she removed various hairs to thin and
shape his eyebrows. Once she finished, Ariana turned to Portia and
said, "Should we let Jeff see it now?"
"Sans makeup?" Portia inquired.
"Well, we have to teach him how to apply it."
"Very well," Portia replied.
Ariana nodded before she took hold of a hand mirror from her bag and
brought it over to Jeff. Jeff took it with a sense of trepidation and
turned it towards his face.
Jeff cringed at the unmistakable girlish look of his hair. While his
eyebrows were passable for a guy's, his hairstyle would never be
confused with anything masculine.
"You said you'd make me look androgynous," Jeff said with a whiny,
stutter.
"You still can."
"How?"
"Just pull your hair back and tie it up in a low ponytail."
"With these highlights?"
"You're making too much of it."
"No, I'm not."
"There's no point whining over it. It needed to be done," Portia chimed
in.
Jeff felt dejected as he realized her point. He put his head down for a
second before he handed the mirror back to Ariana.
Once Ariana put it away, Portia told Jeff to come into the bathroom with
her. The request sounded odd, but Jeff followed her in as Ariana
followed behind them.
Portia took out a bag of makeup and said, "This is yours now."
"It's just what I always wanted," Jeff said with mock sincerity that was
grating to Portia.
"Look we didn't have to help you transition," Portia replied.
"I'm not transitioning," Jeff retorted.
"Call it what you will, but, soon, everyone's going to think of you as
not really a man," Ariana replied.
Ariana's words stung Jeff. He wondered again what he was thinking by
pursuing the course he had chosen.
Still, rather than backing out, Jeff let Ariana apply makeup to his
face. He talked with her as she gave him various instructions about how
to apply each cosmetic to his face while she did so. Jeff tried to take
mental notes while Portia watched them intently, almost in shock of how
feminine Jeff's face looked when the makeup was added to it.
"I can barely recognize you," Ariana said with a laugh while Jeff
thought the same thing as he looked in the mirror.
"There's just one more thing," Portia said.
"What?"
"Jeff, take out your contacts."
"I kind of need them to see," Jeff retorted.
"I've got glasses for you."
"How do you know my prescription?"
"It's in your medical records."
"Isn't that sort of thing supposed to be personal and confidential,"
Jeff replied, feeling violated.
"A lot of things aren't the way they're supposed to be these days,"
Ariana replied while she ran her fingers through his highlighted and
layered hair.
Jeff nodded as Portia handed him the brown colored, rectangular framed
glasses. Jeff removed his disposable contacts before he put them on and
almost did a double take as he looked at his reflection.
"It's amazing how different you look with glasses, isn't it," Portia
said.
Jeff nodded, surprised by the difference the glasses made in conjunction
with the makeup and his hair. While Jeff had no attraction to the girl
in the mirror before, Jeff felt slightly alarmed that he would likely
have made a move on the girl staring back at him given his undiscerning
taste in women.
"Are you ready for the next step?" Portia asked before Jeff turned his
head to face her.
"At this point, what choice do I have?" Jeff inquired.
"You can still back out," Portia replied.
"No. I'm in too deep," Jeff responded.
"My sentiments exactly," Ariana interjected.
Portia nodded her head at the two of them before she went and retrieved
a bag full of clothing and gave it to Jeff. Jeff sorted through the
garments and asked, "What should I wear?"
"You can surprise me with that one."
"I'm not sure about this."
"Well, if you want out, you...."
"No. I'm just not sure what works with what."
"Give it the old college try, dear," Ariana replied for Portia.
Jeff nodded before the girls left him alone in the bathroom. Jeff
closed the door behind them and stared at his feminized reflection in
the mirror for a second.
"My God, I'd do me," Jeff muttered before a sense of shame came over him
as he mumbled, "What am I, Buffalo Bill?"
Jeff reached into the bag and saw a black, gel padded bra. After taking
off his shirt, Jeff put his arms through it before he hooked the front
enclosures. Jeff then looked into the bag and took hold of a skirt.
Jeff thought for a second about his hairy legs and opened the door. He
poked his head out and said, "Girls, how can I wear a skirt?"
"By putting it on two legs at a time," Portia rejoined.
"No. I'm talking about with my legs."
"Shave them," Ariana answered.
"Shave them?"
"Yes. Is that a difficult concept to grasp?"
Jeff shook his head before he closed the door behind him. He looked
into the bag and saw a pair of beige pants and breathed a sigh of
relief. Jeff put the skirt away and took hold of the pants and a pair
of panties.
After removing his pants, Jeff pulled the panties up against his body.
The unsightly bulge in the black satin panties seemed to be out of place
to Jeff, but he enjoyed the sensations that accompanied the
undergarment.
Jeff then brought the wide leg, linen pants up over his hairy legs. As
Jeff pulled up the zipper, he gave his bulge a worried look. 'That just
looks so wrong,' Jeff thought while he looked at how his crotch appeared
in his pants before he removed a long sleeved, white sweater top from
the bag.
Jeff pulled the top over his head and straightened it out over his waist
before he looked at how the small bumps on his chest from the bra pushed
the top away from his body. His eyes drifted to its cowl neckline
before examining how girlish he looked in the figure-hugging top.
As Jeff moved around the bathroom while he reached for the doorknob, he
realized that he was stepping on the bottom of his pants legs and
muttered, "Why are these long?"
Upon Jeff's emergence from the bathroom, the girls began to laugh. Jeff
blushed before Portia said, "Don't you see anything wrong with that
look?"
"I see a lot of things wrong with it," Jeff retorted as his eyes focused
on a crack in Portia's ceiling.
"No. I mean is there anything not so lady like about it?" Portia
inquired.
"Uh...everything about me," Jeff answered, feeling as though that answer
was self-evident.
"How about specifically between your legs," Ariana asked.
"Yes, but what am I going to do about that?"
"You've got to do something," Ariana retorted.
"Why?"
"What are people going to think if you walk into a room with a boner in
girls' pants," Ariana replied with a laugh.
"I don't have a boner," Jeff retorted with a snarl.
"Calm down," Portia said, sure that Jeff assumed that Ariana thought
that his flaccid package was as big as it could get.
"I am calm," Jeff countered before rocking forward and pulling up the
legs of his pants.
"Oh, you noticed that," Portia said.
"What?"
"The length issue."
"Yah, what's with that?"
"You need to wear heels with those pants."
"Heels?"
"Yes."
"As in high heels?" Jeff inquired with a worried look.
"Or mid heels," Portia countered as she removed a pair of white pumps
from a bag.
"You can't be serious."
"You're the one who wanted to be a saleswoman," Portia countered.
"I didn't want that!"
"Then take the other job," Portia said, hoping that Jeff would finally
see the folly of his decision.
Jeff decided that he would not give in and surrender a position that he
had established himself as the premier performer at in the company.
Jeff took the heels from her and stepped into the pointy toed, patent
leather shoes.
Jeff felt oddly off balance as he stood in the two and a half inch
heeled shoes. He gave Portia a nervous look before he asked, "Do we
sell any flats?"
Portia nodded with a grin before she added, "And wedges."
"Is that an improvement?" Jeff said before he looked down at his feet.
"Oh, honey, you have so much to learn," Ariana countered before she got
up and said, "Do you know how to walk?"
"Put one foot in front of the other."
"That's a start, but you should keep your feet as straight as possible
in heels."
"You don't want to turn your ankle," Portia added.
Jeff nodded before he followed Ariana's lead and walked like her. As he
finished taking his lesson from her, Jeff looked over the bags of
clothing Portia had for him and said, "Is that all my choices."
"All your choices that could work for you."
"What does that mean?"
"You don't have the arms to go sleeveless."
"What?"
"Your upper arms are too big for a sleeveless dress or top. You have to
have sleeves to cover up those man arms. It's a dead give away."
"But it's what I am."
"But not what you're trying to project," Portia countered before she
added with a grin, "Other than that, though, you've got everything."
"Isn't there anything a little more manly?"
"Jeff, you've got several lovely options," Ariana said while she started
pulling out tops before she stopped to hold one up to Jeff. She grinned
at the ivory colored shirt decorated with tiered, asymmetrical ruffles
and said, "Oh, I think this is kind of manly. It's very piratey. Arr,
my little buccaneer."
Knowing where she was going, Jeff replied, "But I don't want to be a
pirate".
Ariana and Portia laughed before Ariana said, "I think you steer clear
of this one.
Jeff nodded before Portia added, "And there's one more thing, you're
going to need if you're going to wear pants."
"What?" Jeff inquired.
"This doesn't come from our line because it's an umm...specialty item,"
Portia said as she took hold of a garment that struck Jeff as a
mutilated pair of panties.
Jeff took hold of the padded item and gave Portia a strange look before
she said, "It's a padded pair of panties."
"Say that five times fast," Jeff replied.
"They'll help you out."
"How so?"
"By making your hips and butt stick out more," Ariana replied.
"How will that help with this?" Jeff inquired as he pointed to his
front.
"They're extra snug," Portia answered.
"What does that mean?"
"You can tuck yourself away in them."
"Tuck?"
"Did you ever see Silence of the Lambs?" Portia inquired.
Jeff nodded before she said, "Don't you remember when the killer was
dancing in front of the mirror?"
"I've tried to block that from my memory like that Harvey Keitel scene
from Bad Lieutenant, but yes."
"Do just that, but you let the panties hold it between your legs instead
of your thighs."
'Dear, God,' Jeff thought as he remembered what Buffalo Bill did in the
movie.
"Do you need help?" Ariana asked, observing his stupor.
"No," hastily replied before he moved back into the bathroom before
Portia said "And just one more thing."
"What?"
"Take these," Portia said as she removed two C-cup breast forms from a
bag.
"Okay," Jeff replied without emotion before he carried them into the
bathroom, trying to hide his utter embarrassment from the girls.
Jeff dropped the pants to the floor along with his panties before he
pulled the padded panties up his legs. They felt far less comfortable
than the satin panties by his feet, but as Jeff tucked himself away, he
realized that they were far better at creating a feminine illusion for
him.
Jeff then stepped back into the pants and brought them up to his waist
and fastened the zipper once again. After giving his smooth front a
nod, Jeff lifted up his top. He stuffed the padded cups of the bra with
the breast forms before stepped back out of the bathroom.
Portia and Ariana gave Jeff approving nods before Portia said, "If I
didn't know better, I would have thought you were born a girl with that
figure."
Portia's words were not comforting to Jeff, who felt even more disturbed
at the prospect of passing himself off as a woman than being seen as a
cross-dresser. 'If I can pass myself off as a woman, what kind of man
does that make me?' Jeff wondered.
Portia broke the silence in the room by offering to make them lunch.
Jeff and Ariana agreed and helped Portia prepare the meal before they
sat down together at Portia's kitchen table and ate.
Once they finished, Portia and Ariana took turns giving Jeff advice as
to how to conduct himself as a woman. Jeff took mental notes about how
to sit and walk and practiced his motions with the girls, trying to
ensure that when he had to venture out as a woman, he would not give
himself away. While Jeff continued to practice moving about like a
woman, Ariana agreed to come to his home the next day to help him
further.
As the evening hours came, Portia sent Jeff and Ariana on their way
home. Jeff was not given the option of changing and did not put up much
of a fight before he found himself carrying out his bags of clothing to
the car with Ariana and Portia.
Jeff put the bags in the trunk and said goodbye to the girls before he
drove home. Jeff sunk low in his seat as he drove down his block,
hoping not to be recognized before he pulled into his driveway and
opened his garage door. Jeff quickly closed it behind his car before he
exited the vehicle.
Jeff brought the bags into his home and put away the contents in his
guest room before he changed into his male clothing and made dinner.
Once he finished with dinner, Jeff took a long shower, hoping to cleanse
himself of every hint of his feminine makeover.
After drying off, Jeff stared into the mirror and saw the makeup traces
still on his face. He sighed before he remembered that Portia had noted
that she had given him makeup remover. Jeff exited the bathroom and
took hold of his purse and removed his makeup bag. Jeff then took to
applying the makeup remover.
Once Jeff finished, despite the lack of makeup and mustache, Jeff
thought that his reflection still looked feminine from the neck up due
to his hair and eyebrows. 'What did I get myself into?' Jeff wondered
before he took hold of a razor.
He stared at his mustache and said, "Sorry old friend."
Jeff took to shaving it and stared at the smooth skin left behind with
each stroke of the razor. He shook his head and thought, "Mom, would
love this," as he late mother's admonishment over her hatred of his
mustache entered his mind as he removed all traces of it. Once he
finished, Jeff turned in for the night.
After breakfast the next morning, Ariana came over to Jeff's home. Jeff
let her in and they made small talk as she helped him through a dry run
of putting on makeup and styling his hair before he sorted through the
clothing the company sold.
Jeff then dressed in what he felt was the least revealing dress he had
been given. He pulled the long sleeve, pleated, knee length dress over
his head. After pulling up the back zipper, he fastened the attached
belt at his waist and made sure that his keyhole neckline showed nothing
he did not want it to show. Satisfied with his appearance in it, he put
on a pair of camel colored, patent leather wedges before he came out to
greet Ariana en femme. Ariana grinned at Jeff and complimented his
rounded toe shoes before she added with a wink, "I have a pair just like
them."
"I bet you do," Jeff replied, giving his company issued four-inch high
wedges a nervous glance.
"But they look better when you shave your legs," Ariana added to
admonish him.
"I'm not there yet."
"At least you got rid of the mustache."
"Don't remind me."
Ariana nodded her head with a smile before she began to put Jeff through
his paces through a crash course in femininity. Jeff struggled to keep
straight each recommendation regarding how to sit, walk, talk, gesture
and stand.
"Who knew so much went into being a woman," Jeff remarked.
"Every woman," Ariana retorted before flashing him a grin and continuing
to give him tips on how to conduct himself as a woman.
When Ariana went to leave, she turned to Jeff and said, "Are you sure
you know how to do your makeup?"
"I got it, and, besides, I'm not going to need to wear it tomorrow
anyway. I'm not leaving the office."
Ariana nodded her head as a smile came to her face. She walked out the
front door and started to laugh a little as she thought, 'He thinks he
can pass himself off as normal guy. Good luck with that, honey.'
-----------------------------------------------------------------------
The next morning, Jeff walked towards his office, trying to project
confidence as he entered dressed in products from the company's line.
He had taken great care to sort through the various garments that Portia
had delivered him to piece together the most masculine outfit he could
for his first day at work sporting the company's women's line.
Jeff saw a man giving him a derisive look as Jeff made his way to the
door. Jeff heard the man mutter something, certain that he heard the
word, "Fairy."
Jeff blushed as he put his head down, wondering if the abuse he was
going to take was worth it. Jeff moved quickly towards his office's
door, hearing his black leather moccasins slap against the stone hallway
floors beneath them. While Jeff had never even thought to wear
moccasins when he dressed in men's clothing, he knew that they were
easily the most androgynous shoes in the company's female collection
when he put them on that morning.
The eyes of the receptionist stared at Jeff as he made his way through
the door. Her eyes examined the absence of curves on his chest since
Jeff felt that the blue button up blouse appeared masculine enough to
wear without the padded bra.
"Hi, Jeff," the girl said, struggling not to laugh.
"Hi," Jeff replied, blushing, which made the girl giggle while she took
a look at the black straight-leg pants he was wearing before he quickly
moved past her. She turned and saw the outline of his white briefs
under the pants and had to put her hands over her mouth to keep from
laughing to loudly.
Jeff turned back and looked at her and shook his head thinking, 'Some
people have no sense of professionalism.'
As Jeff made his way through the office he saw more eyes turn towards
him. He could see them snickering but decided not to pay them any
attention.
'You're going need tough skin to get through this,' Jeff reminded
himself as he struggled to maintain an emotionless expression on his
face.
Jeff entered his office and began to make calls and manage his clients
as he normally did. Since they were unable to see him, none of his
clients noticed anything different about Jeff while he did his work from
the safety of his office.
As the mid morning rolled on, Jeff called out to one of the secretary's
for a cup of coffee. A young girl carried in a cup for him a few
minutes later and said, "Here you go, Jeff?"
"What's with the upward inflection on my name?" Jeff inquired to the
nervous looking girl.
"It's kind of hard to call you Jeff when you're dressed like that."
"These clothes aren't all that girlish. They look normal on me," Jeff
counted.
'No, they don't,' the girl thought before she answered with a smile, "Of
course, Jeff."
She exited the room, rolling her eyes at Jeff's delusions before he got
back to work. Jeff continued to work until the early afternoon, when he
stepped out of the office to speak to some of the other sales staff.
As Jeff walked through the hallways, he could see his fellow employees
were craning their necks to get a look at him from behind. 'Oh, just
come up to me if you want to take a look you pansies,' Jeff thought
while he entered the first saleswoman's office.
The saleswoman struggled to keep a straight face as they discussed
client accounts and sales before Jeff moved onto another saleswoman's
office and had a similar conversation. Jeff heard snickers from the
support staff as he moved on to Ariana's office shaking his head, sure
that he was the butt of all their jokes.
Ariana greeted Jeff warmly before she asked, "How are things going?"
"They've been better," Jeff replied while he looked down at his outfit.
"I give you credit for following through with it," Ariana responded.
"Thanks."
"So, how are your sales going?"
"It's only one day, and so far there's no difference. That's the good
part. Most of my sales are over the phone. I haven't met most of the
people who buy from us, so this shouldn't be problem for most of my
customers because they'll never know."
"You're going to have to show yourself eventually," Ariana reminded
Jeff, knowing that he met with some of his clients that were located in
the region throughout the year.
"I know. I know," Jeff replied.
After discussing sales strategies for a few minutes, Jeff went to go
back to his office. As Jeff walked away from Ariana, Ariana caught
sight of his underwear lines and said, "Hold on a second, Jeff."
"What?"
"We need to talk."
"Here?"
"No. With Portia," Ariana replied as she moved past him.
Jeff gave her a curious look but decided to follow behind her towards
Portia's office. Ariana paused before the closed door and asked
Portia's secretary if she was in the room with anyone. Jeff stared at
the nameplate reading Portia M. Dawn while he listened to the
secretary's response.
Ariana then knocked on the door. Portia called out that Ariana could
enter before Jeff followed in behind her.
"What's going on?" Portia inquired while Ariana closed the door behind
her.
"Can't you see it?" Ariana asked.
"What?" Portia asked as Jeff raised his eyebrows.
"Jeff, spin around," Ariana said.
Jeff looked at her in silence before Ariana said, "Don't look at me like
I have three heads. Give me a spin."
"Okay," Jeff replied slowly before he slowly rotated.
As he did so, Portia caught sight of his briefs through his pants and
laughed a little.
"Why is everyone laughing at me?" Jeff inquired
"I don't know how to tell you this, Jeff?" Ariana said.
"What?"
"I'd say you had visible panty lines, but I don't think those are
panties..."
"Maybe visible manty lines is better," Portia added.
Jeff blushed as he reached down and felt his briefs through the soft
fabric of his pants.
"Not as concealing as what you're used to, are they?" Portia inquired
with a grin.
Jeff shook his head swiftly from side to side before Ariana said, "You
have to be more careful when you're dressing like that."
"I get it," Jeff replied.
Portia nodded her head at Jeff before she gave him a sympathetic look.
She got up and said, "Wait here for a moment."
Jeff nodded before Ariana began to ask about how he was handling his
work that morning. They discussed their various business dealings
before Portia reentered her office after more than ten minutes had
passed.
"What is that?" Jeff asked while he glanced at the long, black garment
in Portia's hands.
"It's a tunic. You know what it is."
"But why are you giving it to me?"
"It'll give you a little more modesty."
Jeff cringed at the suggestion, knowing that the tunic was unmistakably
a woman's garment. He had dressed that morning, trying to look as
masculine as possible in his woman's clothes. Jeff knew the tunic would
destroy any pretense of his outfit being unisexual.
Still, Jeff figured that it would not be worse than enduring the further
snickers from the coworkers that were leering at the lines of his
underwear when he walked by. Jeff took the tunic from Portia before he
thanked her and exited her office.
Ariana shook her head at Portia as Jeff left them alone. Portia rolled
her eyes and said, "I gave him every opportunity to not do this."
"I have no idea what he's thinking," Ariana replied.
"He's not up to being a woman," Portia responded.
"He's not even trying to be one. He just looks like a total sissy."
"He might need an intervention," Portia replied, shaking her head before
Ariana exited her office to get back to work.
Jeff hurried back to his office and closed the door. He unbuttoned his
blouse and neatly folded it before he placed the long sleeved, black
tunic on. He was relieved that it covered his rear, despite knowing
that it would make it abundantly clear to anyone who looked at him that
he was cross-dressed.
Jeff stepped back behind his desk and caught sight of his stress ball.
Jeff clenched it in his hands and pressed into it several times as he
took deep breaths trying to calm himself down. After a few minutes,
Jeff picked up the phone and began to make some calls.
As he worked, Jeff saw several of his coworkers snickering while he
talked with his clients using his male tone while dressed in the tunic.
He struggled to not pay any attention to them, but he often found
himself grinding his teeth and muttering under his breath as he finished
working that day.
While the next day came and went like the first, as Jeff spent most of
his time managing clients and taking orders over the phone, Jeff knew
that he had to go out to meet a client on Wednesday. Jeff talked with
Ariana the day before and asked her to come over that morning to give
him a hand.
Ariana agreed, but only after she told him that it would be the last
time she would oversee his feminization. Jeff was worried about that,
but he knew that he was in no position to complain.
Ariana arrived at Jeff's house the next morning, earlier than he even
typically liked to wakeup. Jeff was groggy while he opened the door and
greeted her as she stood before him, impeccably dressed in the company's
line without a single hair out of place.
Shortly after she entered, Ariana inquired what Jeff was going to wear
to his meeting. Jeff said, "I'll show you."
Ariana nodded as she followed behind Jeff as they walked towards his
bedroom. Jeff opened his closet doors and pulled out the outfit he was
planning to sport that day.
Ariana shook her head with a laugh and said, "That just doesn't work,
Jeff."
"Why not?"
"The colors are all wrong."
"They are."
"These are things you have to learn if you're going to keep parading in
skirts," Ariana chided.
"Sorry," Jeff replied before adding, "I'm going to get better with
practice."
"Yes, practice makes perfect, but nobody's perfect."
Jeff nodded before he asked, "Well, what would you go with?"
"I'm wearing clothes from the same line as you Jeff, but, that aside,
for your meeting, I would go with something a little conservative, since
this is the first time you're meeting them as a woman. You don't want
to wear anything loud that says I'm here, I'm queer, get used to it."
"I'm not gay!"
"I know you're not, but a lot of people think that trannies are all
gay."
"But I'm not."
"Jeff, you have to manage expectations, including your own. People,
whether you like it or not, are going to see you in a dress and say
'Gay.' Going forward, you're gay, regardless of the fact that you're
straight, just like everyone in the office does. Can you deal with
that? If not, you need to find another line of work."
Jeff blushed at Ariana's stern words. He knew that she was right. He
was determined to prove to himself that he could still be a top salesman
despite it. Jeff nodded his head and said, "Okay. I can deal with it."
Ariana gave him a silent glace that lasted for a few seconds as she
thought, 'What is it going to take for you to put away your stupid male
pride?'
Ariana sighed before she said, "So, what are you going to go with?"
Remembering Ariana's advice, Jeff reached into his closet and removed a
black skirtsuit and a dark gray, caprice Jersey top. Ariana looked over
the outfit and nodded before she said, "That'll work, but with that
skirt, you're going to need some hosiery."
"I was thinking about donning some pantyhose," Jeff admitted.
Ariana smiled, still struck by the novelty of hearing a straight man say
such a thing to her. She nodded before she asked, "Do you have the legs
for that?"
"I shaved them yesterday."
'This is almost too much,' Ariana thought before she said, "Go get
dressed. I'll wait right here for you."
Jeff nodded before he opened his dresser drawers and removed a bra,
breast forms, his padded panties and a pair of black pantyhose. He
carried them into his bathroom before he returned and collected the rest
of his outfit.
Jeff placed on his bra and panties first before stuffing the cups of his
bra. Jeff then rolled down the pantyhose as he had been trained and
brought them slowly up his legs, careful not to repeat his initial
failures that resulted in several ruined pairs that were now being used
to help even out his false breasts.
After finishing pulling the control top of his pantyhose to his waist,
Jeff took hold of his black skirtsuit. Jeff stepped into the black
pencil skirt and brought it over his nylon-covered legs before he took
hold of his top. He placed on the three-quarter sleeved top and
adjusted the top's surplice neckline over his false bust. Once he
finished adjusting his top, he put on the jacket of the suit, which was
adorned with notched, inverted lapels before he opened the bathroom door
to walk back out to see Ariana.
"How do you let male pride lead you into a skirt," Ariana muttered as
she looked Jeff over, still mildly surprised by how feminine he appeared
as the hem of his skirt pulled against his smooth legs with each step.
"What do you think?" Jeff asked as he nervously clasped his hands
together.
Ariana nodded as she said, "You look good from the neck down."
"Well, that's why I need you."
"I don't know why. I taught you everything you need to know."
"I just want to make a good first impression when I'm reintroducing
myself."
"I get that," Ariana replied, still not getting why he simply would not
take the job reassignment that had been offered to him. 'Why would you
reassign your gender instead?' Ariana wondered.
Ariana stood up and led him towards the bathroom before Jeff sat upon
the toilet seat. Ariana took hold of Jeff's makeup bag and put her
practiced skills to work as she applied layer after layer of cosmetic to
his face, giving Jeff reminders on how to do it as she worked.
Once she finished with his makeup, she began to brush out and style
Jeff's hair. Ariana nodded as she finished and told Jeff to take a
look.
Jeff stood up and gazed at his reflection. As with the first time he
saw himself en femme, Jeff could almost not believe that he was staring
at himself. It was only his bone structure that made him reconcile his
self-image with his reflection
Ariana checked her watch as Jeff admired his reflection and said, "We've
got to get rolling, girlfriend."
Jeff shot Ariana a peeved look over the statement, prompting her to
reply, "Hey, you dress like that, what do you expect people to call
you?"
Jeff nodded, begrudgingly acknowledging her point as he knew he would
likely be called far worse by some others he encountered. Jeff then
headed into his bedroom and grabbed a pair of black wedges to pair with
his outfit before he took hold of his purse and led Ariana out of his
home.
While Ariana drove to the office that morning, Jeff veered off his
normal path for a breakfast meeting with a long time client. Jeff was
nervous as he pulled up in front of the diner where he was meeting the
middle-aged woman.
Jeff got out of the car and headed for the door. He walked in and was
greeted politely by the hostess before he spotted his client already
sitting at a table alone.
Jeff stared at the woman for a few second before he found the courage to
approach her. Jeff walked up to her and nearly walked past her before
he said, "Hello, Dolly."
Dolly gazed at Jeff for a second trying to figure out who he was before
she recognized his face. Jeff began to squirm as Dolly started to laugh
as she asked, "What's with the get up, Jeff?"
"Get up?" Jeff replied, before trying to play it off as a joke by
saying, "Oh, you mean the clothes."
Dolly nodded with a grin.
"They're from our new line. Don't you just love them? Imagine how a
real girl would look in these."
"I'd bet better," Dolly replied before asking again, "Really, what's
with the outfit?"
"We discontinued our male line."
"I know that. It's still not an explanation."
"As a sales...person, I have to model our current line," Jeff replied.
"So, you have to be a saleswoman, now?" Dolly asked before she let out a
laugh.
"I'm not really a woman."
"But you're not a girl either. I think Brittney Spears made a song
about that circumstance. Any relation?"
"I wish."
"Careful, you'd probably have five kids by now at your age or no teeth,
if you were."
"A strong possibility."
"Still, what's with the outfit?" Dolly persisted to inquire.
"I told you, I'm modeling the line."
"Okay," Dolly replied with a smile as Jeff sat down.
A waitress quickly came over and took their orders before leaving them
with their cups of coffee. Jeff steered the conversation to the
company's new line. While Dolly was interested, invariably, the topic
of conversation was turned by Dolly back towards Jeff's appearance.
"So when did you come out?"
"I'm not."
"Well, you're certainly not in with that look."
"I think this look is very much in," Jeff countered with a grin.
"In for a girl," Dolly replied with a laugh before their meals were
placed in front of them.
"In for the girl who knows what she wants," Jeff countered.
"I guess a girl's heart wants what it wants, even if it's stuck in the
wrong body."
Jeff cringed at the suggestion before he replied, "You know I'm really
not gay."
"I know that now."
"Now?" Jeff asked confused.
"I always thought you were gay, you know with the mustache and all.
It's a dead give away like being a cowboy or having a motorcycle."
'So is every Indian, cop and sailor gay too,' Jeff thought of
responding, but replied instead, "I'm really not gay."
"I know you're a girl. So, you're straight."
Jeff stared at her dumbfounded for a second before he started talking
about what he was trying to sell her while they continued to eat. Each
time that Dolly tried to inquire about Jeff's personal life and sexual
orientation, Jeff steered the question back towards the company's line
of goods. Dolly nodded along as she looked over the company's new line
before she agreed to an even larger order of goods than he normally sold
her by the end of their breakfast.
After Jeff paid for the meal with his company credit card, he followed
Dolly to the parking lot. He escorted Dolly to her car before Dolly
said, "I hope that you find happiness, Jill."
Jeff almost forgot that he told her his feminized name while they ate
before he thanked her. Dolly nodded before she said, "And remember,
dear, finding a good man never hurts either."
"I'll keep that in mind," Jeff replied with a smile, even as the thought
disgusted him.
Dolly nodded again before she got into her car. Jeff waved goodbye to
Dolly as he watched her pull out of the parking lot as he moved towards
his car. As she drove down the road, Jeff stepped into his car and
closed the door before letting out a deep toned, loud, "YAH!"
Jeff did multiple fist pumps as he sat in the driver's seat before he
realized how strange his behavior had to seem to anyone who may have
been watching given his feminized appearance.
Glancing around, Jeff was relieved to see that no one was in sight
before he did another small fist pump and started his car. Jeff's heart
raced a little as he felt the familiar rush that overcame when he made a
big sale. The excitement that he got from it was something that he did
not get from anything else in life.
As he pulled out of the parking lot of the diner, Spirit of Radio came
onto the station he was listening. Jeff cranked up the volume and began
to sign along and banging his head slightly from front to back, causing
him to have to keep moving his glasses back up his nose while he drove.
Shortly before he pulled into the parking lot of his office, Don't Stop
Me Now came on after the Rush song. Jeff sang along to the blaring
Queen song as he drove through the parking lot before he saw the slacked
jaw faces of some of his coworkers as they held their cigarettes to the
side and stared at him.
Jeff blushed, aware of how bizarre