New! Salesman to Maid

Cherry

Thank you all for the lovely reviews on my as yet unfinished "Cucked
and Sissified" story. As life has gotten in the way of continuing that
for the time being, I'm going to try to exercise my writing muscles
with some shorter pieces over the next few weeks. Most will be single
stories; I'm anticipating this one to be a two-parter. I have already
started work on part 2 so I'm hoping to conclude it very soon!

*****

The party had been a success, and now it was winding down. For Frank, a
young sales rep, it had been his first time attending the company's
famous Halloween party. The company rented out a club each year, and
every employee, from the executive level down, attended in costume.
There was an open bar, and it was understood that anything that
happened at the Halloween party stayed at the Halloween party. Several
couples were making out, some in dark corners, many right on the dance
floor, and Frank was aware that many employees were snorting cocaine in
the men's room.

Frank turned down that particular offer, as well as some jokingly lewd
ones that he received while in the men's room, along with suggestions
that he was in the wrong bathroom. You see, Frank, a handsome man whose
youthful good looks had caught the eye of a few of the women in the
office, was dressed as a woman on this night. A few weeks before, the
sales team had been discussing costume ideas. Although he couldn't
remember the entirety of the conversation, he had ended up accepting a
dare to dress up as a sexy secretary.

Frank had done his homework. Knowing what a big deal the party was, he
was determined to try to look good. He had purchased cosmetics, watched
YouTube makeup tutorials, and on the day of the party spent over an
hour perfecting his look. There was no hint of a five o'clock shadow,
his eyebrows were immaculate, and his lips and fingernails were an
identical shade of light red.

He had bought the clothes online. Nothing fancy or expensive, but as he
put them on he could see the outfit was going to work. He was wearing
plain black panties, thinking that his usual boxers would feel strange
with the rest of the ensemble. Over them he pulled up a high-waisted
black miniskirt, which ended well above the knees. Next came a white
long-sleeved top, with black detail on the chest. The sleeves were
flowy but tight at the wrists - a feminine, attractive but sensible
look, something he could see any of the young women in the office
wearing.

Next came the sheer black stockings, which he carefully rolled up his
legs. His skirt was just short enough that there was a hint of the top
of the stockings when he stood, while they were fully visible if he sat
down. He placed a long, wavy brunette wig on his head, just a shade
lighter than his natural color, and saw an undeniably attractive young
woman looking back at him in the mirror. A bracelet and ring, left at
his apartment some months earlier by a girl he had been hooking up
with, adorned his red-tipped hands.

Finally, it was time for the shoes. Frank had to admit he had been
overambitious in selecting his footwear. He had received the black
pumps in the mail a couple of weeks before, and when he saw the four-
inch high heels up close considered returning them. Instead, he
stubbornly set to practicing, wearing them around his apartment for a
while every evening until he could reasonably walk in them. Still, he
didn't know how he'd hold up over an entire evening of dancing.

Frank had been a hit. Women had complimented him, guys had jokingly hit
on him, he had won one of the best costume prizes and with it a
generous gift card, and more importantly he had got some quality time
with Shelly. Shelly was a beautiful blonde who Frank had developed a
crush on during his few months with the company. Being on the shy side,
he had limited his interactions with her mostly to office pleasantries,
but he had had some success chatting with her at the occasional after-
work happy hour.

On this night, Shelly had opted for the classic sexy she-devil look,
complete with red horns, and she looked stunning. Loosened up by
alcohol, the two had ended up meeting on the dancefloor, and while they
didn't go as far as many of the couples around them, the sexual
chemistry between them was undeniable. Frank knew that he could build
on this in the coming weeks and hopefully he'd be dating Shelly before
long.

Sadly, closing time was approaching, and Shelly had a ride with some of
the other girls. She gave Frank a kiss on the cheek, very close to his
mouth, and a playful squeeze on the ass before leaving him happy but
horny. He was pretty sure he had a wet spot on his panties as he found
the nearest chair and sat down. He gazed absent-mindedly at his
feminine-looking hands as he stirred his drink, and began thinking
about how to get himself home.

Just then, his boss, Mr. Walker, dressed as a vampire, approached him,
snapping him out of his reverie.

"Frank, I think we're headed the same way. Need a ride home?" he asked.

"Yes, Mr. Walker, that would be great," replied Frank. "I'd really
appreciate that."

"Well, come on then, young lady," smiled Mr. Walker. He put out his
hand and Frank took it daintily, playing along as he stood up.

"Ooh, thank you, Sir," he breathed in the fake girly voice he had been
using earlier in the evening, batting his mascara-covered eyelashes.

Mr. Walker chuckled and led Frank outside, his hand gently on Frank's
lower back. Frank didn't really notice it at the time, as standing up
so suddenly had made him realize he was more drunk than he thought.

Soon they were in the back of a black car, exchanging small talk about
how fun the party had been before going silent. After a few minutes,
Mr. Walker turned to his young employee.

"You know, Frank, I'm not ready to call it a night yet. How about a
nightcap at my place?"

Frank thought for a moment, then agreed. He figured he'd just been
handed a golden opportunity to get in the boss's good graces, and he'd
be a fool not to take it.

Minutes later, the car was pulling up to Mr. Walker's imposing house.
Mr. Walker was in his fifties, by all accounts a handsome man who kept
himself in shape. Frank knew that he was divorced and his children were
grown, in college he thought, so he lived alone.

Mr. Walker opened the door and again put his hand on Frank's back as he
led him inside. The young man's feet were aching in his heels just from
walking between the car and the door, so he gladly dropped into a
leather couch as his boss prepared drinks for them both. Mr. Walker's
drink of choice was straight Scotch, and although Frank favored mixed
drinks he accepted. He took a single sip and started coughing, making
his boss laugh as he sat beside him.

Frank had rarely spoken with his boss one-on-one, as most of their
interactions had been in team meetings, and he found himself
surprisingly intimidated by the older man, who was leading the
conversation, now turned to work. Frank struggled to maintain eye
contact, often looking down at his painted fingernails, and past them
to his skirt, stockings and shoes. He decided that his outfit and the
alcohol were conspiring to make him nervous, and he tugged at his
skirt, trying to pull it down past his stocking tops.

Mr. Walker noticed and chuckled softly.

"That's quite the getup, Frank," he said smiling.

"Y-yes, Mr. Walker," stammered the young man. He wasn't trying to use
his fake girly voice, but for some reason he was having trouble
sounding manly. "It was just a joke with the guys."

"Well, you look great, Frank. Am I right in thinking you've done this
before?"

"N-no, Sir," answered Frank truthfully. Mr. Walker was looking deep
into his eyes now, and Frank was utterly failing to meet his gaze,
looking only down. His hand was shaking lightly. Suddenly, Mr. Walker's
hand was on his, steadying it, then taking the whiskey glass from him.
Frank was mesmerized by the contrast between his boss's masculine hand
and his own feminine one with its red nails and silver bracelet, and
felt for an instant like he was having an out-of-body experience.

"Don't be nervous, Frank," said Mr. Walker, firmly but gently. He but
the glass down on the coffee table and sat back. Frank regained some of
his composure and looked at his boss, who was now sitting back, looking
thoughtful.

"Frank, you know I'm divorced, right?" asked Mr. Walker.

"Yes, Sir, I have heard that," replied Frank in the small voice he
couldn't seem to shake.

"I have a proposal for you, Frank. I'll pay you $500 if you accept."
Frank opened his mouth, but no sound came out. "Don't worry, I'm not
going to touch you," added Mr. Walker as if reading his mind.

Frank still made no answer, so Mr. Walker stood up, saying, "Wait
here." He was gone a few minutes, during which Frank just sat there.
Finally Mr. Walker came back, carrying a bundle of black fabric. He
unfurled it, revealing what was undeniably a French maid costume.

"This was my ex-wife's, she looked damn sexy in it," said Mr. Walker.
"I'm offering you $500 cash just to wear it for me, Frank." He pulled
the cash out of his pocket and placed it on the table.

Frank's head was spinning. What Mr. Walker was suggesting was clearly
immoral and perverted, but he was just a harmless, lonely man, right?
And on Frank's entry-level salesman's salary, $500 was nothing to
sneeze at. Plus, if he refused he knew he'd be on the outs with the
boss - his very job might be in jeopardy.

After what seemed like interminable minutes of thinking, Frank slowly
nodded his head, and in his smallest voice said, "Ok," just above a
whisper.

Mr. Walker didn't laugh or anything this time, he just replied, "Great,
you can change in the bathroom down the hall." Frank stood up, as if in
slow motion, and took the bundle from his boss. "You can keep your same
shoes and stockings. Also, please put on the panties as well."

"I'm already wearing panties," said Frank without thinking. Mr. Walker
chuckled at that.

"Perfect," he replied, and Frank walked to the bathroom.

The costume was quite well-made, not a cheap sex-store item. Frank took
off his top and skirt and pulled on the dress. The sleeves were short
and capped, and it felt a little tight around the middle, but overall
it fit quite well. The skirt flared out and was extremely short. Now
his stocking tops would be visible all the time. Frank looked in the
mirror and saw a sexy young maid, all in black except for the white
lace around her neck, sleeves and hem of her skirt. He tied a lacy
white apron around his waist as well as he could, adjusted his wig and
fixed a white cap to the top of it. With one last look in the mirror,
he took a deep breath and, trying not to think too much about what he
was doing, stepped out of the bathroom.

Frank walked slowly. He was now quite used to walking in heels but his
feet were hurting, and he fingered the hem of his dress as he went. Mr.
Walker was sitting back on the couch as his young feminized employee
stepped into the living room. The older man smiled.

"You look wonderful, Frank, thank you. Please come closer." Frank
obeyed, slowly, coming to stand right in front of his boss. "Turn
around, please." Frank did.

He felt Mr. Walker untie his apron, adjust it and do it again. "We want
a nice big bow in the back here, don't we?" he mused.

"Y-yes, Sir," was all Frank managed to say.

"Now, I don't think we can really keep calling you Frank when you look
like that, do you?"

"I-I guess not, Sir."

"Hmmm." Mr. Walker pretended to think. "I'd like to call you Fifi. What
do you think?"

Frank felt the color rush to his cheeks. He was beyond mortified, but
something inside him was preventing him from putting a stop to this.
All he could summon was a, "Yes Sir, anything you like."

"Excellent," smiled Mr. Walker. "I'd like you to do a few things for
me, Fifi."

"Yes, Sir."

"First of all, give me a curtsy."

Frank hesitated, but Mr. Walker just smiled.

"Go on, just grab the hem of your skirt and dip into a curtsy."

Frank did so, clumsily, drawing a chuckle from his boss. "No, no, Fifi,
that won't do."

For the next several minutes, Mr. Walker gave Frank pointers until,
after about a dozen attempts, the young salesman executed what his boss
considered an adequate curtsy, daintily holding his skirt with just two
fingers, bringing his right foot behind his left and dipping in a
submissive, feminine manner.

Mr. Walker then had Fifi walk around the room, curtsying periodically,
while he admired the feminized man's figure. At one point he had him go
to the bar and serve him another glass of Scotch. Finally, after close
to an hour, Mr. Walker was satisfied. He hadn't planned any of this,
but he knew the young man was as good as broken, even if Frank himself
didn't realize it yet. Mr. Walker abruptly announced that it was time
to call it a night, and that Frank could sleep in the guest room.
Frank, as if still in character, dropped into a low curtsy and said,
"Thank you, Sir."

As Frank walked out of the room, Mr. Walker stopped him, saying, "Oh,
Fifi!"

"Yes, Sir?" said Fifi, turning around.

"Don't forget your money." Mr. Walker held out the cash but didn't
move. Fifi blushed again, walked toward his boss and took the money. He
froze for a split second, then curtsied again, much to his own
mortification.

"Thank you, Mr. Walker," he said and turned to go again.

"Good night, Fifi," said Mr. Walker.

Fifi froze again, turned to face his boss and once more, as if unable
to stop himself, dropped into a curtsy, saying, "Good night, Mr.
Walker." He then scampered off to the guest room, looking as girlish as
ever, and more embarrassed than he had ever felt in his life.

*****

The next morning, Frank awoke with a splitting headache. He found a
note on the bedside table, written by Mr. Walker, saying that he had
gone out and providing a phone number to contact his driver whenever he
wanted to be taken home. Frank was embarrassed that Mr. Walker had been
in the room, since he had slept naked, and he was even more mortified
as the memory of the last night flooded back. Eventually though, his
hangover won over and he fell asleep again in the comfortable bed.

It was close to noon when he woke up again, and he was feeling better.
He realized that he had no male clothes with him, and briefly
considered borrowing some, but decided against doing that without
permission. He saw that his secretary outfit had been placed in the
room, so he decided to put that back on. His makeup no longer looked
very good, but he just wanted to get home, so he called the number on
the note. Within minutes, Mr. Walker's driver was at the door,
providing Frank a judgment-free ride back to his apartment, where he
collapsed and spent the rest of his Saturday in bed, half sleeping.

The next day he felt better, and by Monday morning he decided he had no
choice but to go into work and pretend like nothing had happened. He
had no idea where he stood with Mr. Walker, but he figured that if he
ever tried to fire him, he could probably sue for sexual harassment.

The party was still the number one topic of conversation that day, but
Frank was thankful that few people commented on his costume. Instead,
all most of his coworkers could talk about were their Saturday morning
hangovers. Soon, Frank was able to focus on his work. At lunch, he ran
into Shelly in the break room and found her as friendly as ever and
more flirty than usual, although she mentioned she'd be away on a
girls' trip that weekend, so he decided he had more time to build up
the courage to ask her out. By that afternoon, the events at Mr.
Walker's house were almost out of Frank's mind, and he felt like he was
on his way to having a good week.

That all changed abruptly on Thursday morning, when he was called into
Mr. Walker's office. Instantly, Frank felt the butterflies come alive
in his stomach, but Mr. Walker seemed businesslike when he stepped into
his office.

"Sit down, Frank," indicated Mr. Walker. Frank did so, without a word.
He had not spoken directly with his boss all week, which suited him
fine.

"I want to show you something," said Mr. Walker, turning his computer
screen so Frank could see it.

Frank felt like his stomach was dropping out when he saw what was on
the screen. It was a video of him as Fifi, walking around his boss's
living room, curtsying repeatedly, serving him a drink. Mr. Walker
closed the video and clicked through to a large collection of still
images showing Fifi in action, most of them with a smile on his face
that made it look like he was enjoying being a maid. Mr. Walker had
obviously had a camera running somewhere in the room. The older man
leaned back in his chair.

"It's safe to say you wouldn't want these pictures getting out, right
Frank?" he said. Frank couldn't look him in the eye, so he instead
stared at the image on the computer screen. It showed Fifi handing a
glass of Scotch to a man who was out of the frame, only his hand
visible. The maid was already in a half curtsy, his free hand girlishly
holding up the hem of his skirt, and a wide smile was on his face. "I
don't think Shelly would be too impressed."

Frank slumped back in his chair. He had told Mr. Walker about Shelly
that night, and now the bastard was going to use it against him. His
mind was racing. When the young man made no reply, his boss spoke
again.

"All I want is for Fifi to come back and serve me, this Saturday. Think
about it and give me an answer by end of day tomorrow."

All that day and the next Frank could think of nothing else. He was
trying to find a hole in Mr. Walker's plan, but he was failing. The
pictures showed nothing but Frank dressed as a French maid, acting
feminine and serving an unseen man. Mr. Walker could easily spread them
throughout the office without it coming back to bite him. Frank saw no
way out but to submit.

On Friday afternoon he was summoned to Mr. Walker's office again. This
time his boss didn't tell him to sit, so Frank stayed standing.

"Well? Have you made a decision?" Mr. Walker inquired.

"Yes, Sir," Frank replied. His tone of voice made it abundantly clear
what that decision was.

"Excellent," said Mr. Walker, then added, "I'd like Fifi to tell me
herself, properly."

Frank couldn't believe it, but he knew he had no choice. He swallowed,
put on his fake girly voice and said, "Yes, Mr. Walker, I will see you
tomorrow." When his boss just stared, he put his hands behind his back
and dropped his knees into a sort of curtsy, as if to signal his
complete submission. Mr. Walker broke into a smile at that.

"Excellent, Fifi. My driver will be at your door at 8:30 a.m. sharp.
Dismissed," and he gave a wave of his hand.

Frank just curtsied again, said, "Yes, Mr. Walker," and walked out, a
feeling of dread settling inside him.

*****

TO BE CONTINUED (soon!)