New! Salesman to Maid 2

Cherry

At 8:30 the next morning, Frank walked out the front door of his
apartment building. Mr. Walker's driver was there, silent and
expressionless as ever. He opened the door for Frank and they were off.

It was a short drive. This time, the driver led Frank into the house
through the service door, which Frank couldn't help but notice. All the
same, he found himself waiting in the all-too-familiar living room.

He didn't have to wait long before Mr. Walker came in. As if there were
nothing unusual about the situation at all, Mr. Walker just said, "Ah,
Fifi, good to see you're punctual. Your clothes are in the guest room,
please go change and report back here."

Knowing what his employer expected, Frank bobbed and said, "Yes, Mr.
Walker," before heading for the guest room. He found the maid dress
there, along with a fresh pair of panties, black and lacy, sheer
stockings and high-heeled shoes similar to the ones he wore the week
before. There was also some makeup, which Mr. Walker no doubt expected
him to use, and a blonde wig. Frank assumed Mr. Walker's ex-wife must
have been a blonde.

In less than half an hour, Fifi was walking back to the living room.
Mr. Walker was sitting on the couch reading the newspaper, and he
looked up as his feminized employee entered, but didn't say a word.
Taking a hint, Fifi walked up to him and curtsied. At that, Mr. Walker
stood up. Even in heels, Fifi was slightly shorter, and Mr. Walker
looked into his eyes before walking slowly around him, softly
muttering, "Very good."

Fifi looked straight ahead. He could feel his heart beating in his
chest. Finally, Mr. Walker was standing in front of him again. "Follow
me," he said. Fifi did so, and Mr. Walker led him to a door which
proved to be that of the boss's home office.

"You're going to be helping me out today," said Mr. Walker. "Not just
as a maid but as a secretary. After all, that's the costume that got
you into this mess," he laughed.

Fifi did not smile. He just curtsied, said "Yes, Mr. Walker," and sat
in the chair his boss pointed to, to the side of the large wooden desk.
Mr. Walker sat behind the desk. For the next three hours or so Fifi did
secretarial work. Knowing the business, he was very efficient. The
conversation was quite professional, although Mr. Walker referred to
him exclusively as Fifi, whose replies were limited to "Yes, Mr.
Walker" or "No, Mr. Walker." On a couple of occasions, Mr. Walker had
Fifi go to the kitchen and bring him coffee. Fifi did not need to be
told to curtsy as he stood and as he placed the coffee mug on the
table.

Finally, it was time for Mr. Walker to take a lunch break. He returned
to the living room and put a college football game on TV, and
instructed Fifi to make him a sandwich, which he served, of course,
with a curtsy. Just like that, Fifi had gone from secretary to maid,
which would be his role for the rest of the day. Over the next few
hours, he thoroughly cleaned his boss's kitchen, bedroom and two
bathrooms, and had to dust the office. Periodically, Mr. Walker would
ring a bell to summon Fifi back to the living room, where his boss
would tell him to refill his glass or give him some other menial task
which Fifi quickly performed with his automatic curtsy.

Both men were surprised, in their own way, by how easy it had been to
turn Frank, hot-blooded straight male, into Fifi, submissive feminized
maid. Mr. Walker knew he had Fifi totally under his thumb, and Frank
was now resigned to the fact that what little fight he might have had
had been entirely taken out of him. All he could do was try to
dissociate his male identity from Fifi, focus on his work and try not
to think about how this would affect his real life.

Finally, around 6 p.m. Mr. Walker announced that Fifi was free to go,
but not before dropping some news that was not totally unexpected.

"I probably don't need to tell you that you've been on camera all day,"
he said. "I'll be expecting you back here next Saturday, and every
Saturday after that until further notice."

Fifi was exhausted, physically and emotionally, and he felt tears
welling up when he heard that, but Mr. Walker showed no sympathy.

"You may go change. The driver will take you home."

Sitting in the back of the car, Frank let a few tears roll down his
cheeks. He had taken off most of his makeup, but was more worried about
getting home and he knew there was still some around his eyes. He
wondered if the stone-faced driver knew what was going on. He probably
thought Frank was Mr. Walker's gay lover or something, he decided. He
looked for some sign of the driver's thoughts as he held the car door
open for him, but as usual he saw none.

*****

The next Saturday saw Fifi, in full maid uniform, once again reporting
to Mr. Walker. The morning started in familiar fashion, with Fifi
serving as Mr. Walker's secretary. A couple of hours in, however, Fifi
made his first mistake.

He had been sent to the kitchen for coffee as usual and was approaching
the desk with a full mug. He curtsied and put the mug down, but
carelessly knocked it over as he did so, so that the coffee spilled
over the table, the keyboard of Mr. Walker's computer and, worst of
all, onto Mr. Walker's pants. The older man jumped up. Fortunately, the
coffee was no longer piping hot, but he was furious.

Fifi ran as fast as he could in his high heels, painfully aware of how
girlish he looked doing it, to the bathroom for a towel, and just as
quickly returned to the office. He extended his hand holding the towel
for Mr. Walker to take it, but his boss just stared at him.

"What do you think you're doing?" Mr. Walker inquired.

"I-I," stammered Fifi, at a loss for words.

"Get down on your knees and clean me up," barked Mr. Walker.

Fifi hesitated for a split second before his submissive personality
took over. "Yes, Mr. Walker," he said, curtsied and dropped to his
knees. The stain had spread over Mr. Walker's crotch and down much of
his right pants leg. Fifi dabbed at it, trying not to think about what
was hidden inside his boss's pants and stammering, "I'm so sorry, Mr.
Walker, it was an accident."

Mr. Walker was quite calm, and he let the feminized man debase himself
on his knees for a few minutes before saying, "Forget it, Fifi, you're
not going to get it clean. Take my pants off." Fifi looked up from the
floor, speechless, still holding the towel against his boss's leg.

"Do it, Fifi!" shouted Mr. Walker suddenly, making the maid jump.
"You're already in enough trouble as it is."

"Y-yes, Mr. Walker, I'm sorry, Mr. Walker," came the reply as Fifi set
the towel aside and began fumbling with his boss's belt. He finally got
it unbuckled and zipped open Mr. Walker's pants, coming face to face
with the unmistakable outline of his cock in his boxers. He pulled the
pants all the way down, but Mr. Walker was wearing shoes. He sat down
and Fifi knew what he expected. He untied his boss's shoes and pulled
his pants off, then looked up from his kneeling position.

"Put those in the hamper and bring me another pair. I was going to have
you do laundry today anyway," said Mr. Walker, calmly now.

"Yes, Mr. Walker," said Fifi apologetically. He stood up, remembered to
curtsy and walked away.

He returned with a clean pair, wondering if he was going to have to put
them on, but thankfully Mr. Walker did that himself, while Fifi cleaned
the table and keyboard. Finally that task was done. Fifi thought he'd
be returning to his secretarial duties, but Mr. Walker had other ideas.

"That was atrocious, Fifi," he said firmly. Fifi looked at the floor,
abashed. "Unfortunately I'm going to have to punish you. Come lie over
my lap."

Fifi gasped. "W-what?"

"Do it now!" Mr. Walker shouted at the top of his voice.

The startled maid scampered over and, before he really knew what was
happening, found himself over his boss's lap, looking at the floor and
his fake blond hair which cascaded over his face, his heart pounding.

Mr. Walker placed his hand gently on Fifi's back, and started slowly
caressing the young man, bringing his hand down over his ass.

"You've been doing a good job, Fifi, but I have to be firm," he said.
"I can't have a distracted maid or secretary. Let this be a reminder to
you to focus on your work."

With that he flipped the skirt of Fifi's dress up and brought his right
hand hard onto the pantied ass. Fifi gasped, more shocked than hurt.
Mr. Walker continued to spank Fifi, hard, and soon the feminized male
was in real pain, tears streaming down his cheeks.

Finally, after what felt like at least two dozen slaps, Mr. Walker
stopped, and began caressing Fifi's rear end over his panties as the
young man sobbed. Fifi's mind was reeling, he couldn't believe what had
just happened. He didn't dare move, and just when he thought things
couldn't get any worse, he felt an unmistakable bulge under his belly.
Mr. Walker had gotten hard from spanking him.

"I hope you've learned your lesson, Fifi," said Mr. Walker gently.

"Yes, Mr. Walker," sniffled Fifi.

"Good. I wouldn't want to have to punish you again."

With that, Mr. Walker helped Fifi to his feet. The emasculated male
wiped his face and returned to his chair, sitting gingerly on his
reddened posterior, and for another hour he continued to serve as his
boss's secretary. After that, it was back to maid duty: making lunch,
cleaning, laundry, and whatever else Mr. Walker demanded. At the usual
time, Fifi was allowed to change back into Frank and was driven home.

*****

The following week was very difficult for Frank. At first he had
thought he could keep the goings-on at Mr. Walker's separate from his
daily life somehow, but now he knew the spanking had had a profound
effect on him, and he couldn't see a way out. He did his best to avoid
Shelly at work, and was not surprised when Mr. Walker called him into
his office and told him he'd be serving him again that Saturday.

Day three as Fifi the maid went as well as he could have hoped. He
stayed out of trouble and avoided another spanking, but he also noticed
Mr. Walker giving him what he thought were more lustful looks, and he
couldn't help remembering the boner he had felt during his punishment.
Worse, he knew he was falling deeper into submission to the older man.
Every week there was more and more blackmail material that could be
used to ruin him, and he was getting more used to his role as secretary
and maid; he was quickly getting to be an expert at doing his own
makeup, and mincing around in high heels was becoming second nature.

On his fourth Saturday as Fifi, Mr. Walker gave him more bad news: He
would now be serving him all weekend. Resigned, Fifi could do nothing
but drop his head and execute a picture perfect curtsy when he was
told, saying as usual, "Yes, Mr. Walker."

Sure enough, Fifi had to cook and serve dinner that evening, standing
at attention the entire time Mr. Walker ate, then had to clear
everything and do dishes before he was allowed to eat the leftovers. He
stayed as the maid until Mr. Walker was ready for bed, at which time
Fifi retired to the guest room, but not before receiving specific
instructions for the next morning.

As Mr. Walker was an early riser, Frank's alarm went off at 7 a.m.
Groaning, he got up and went to the bathroom. Less than an hour later,
Fifi was showered, fully dressed and made up, and putting the finishing
touches on his boss's breakfast. He put the plate of bacon, egg and
sausage, along with a mug of hot coffee, on his tray and went to Mr.
Walker's room. As instructed, he walked right in, put the tray down and
opened the curtains.

As Mr. Walker woke up, Fifi curtsied, flashed a mandatory smile and
said cheerfully, "Good morning, Mr. Walker."

"Good morning, Fifi," replied Mr. Walker sleepily.

When he sat up, Fifi handed him the tray and stood back, waiting for
instructions. Mr. Walker ate in silence, and when he was done Fifi took
the tray and set it aside. Then Mr. Walker turned to him.

"Come here, Fifi," he said.

"Yes, Mr. Walker." The maid bobbed quickly and walked closer to the
bed.

Mr. Walker had a peculiar look on his face, but Fifi thought he was
just pondering what duties he'd have for him, so he just stood at
attention, looking straight ahead at nothing in particular. Just then,
Fifi jumped. Mr. Walker had put his right hand on the inside of his
stocking-clad leg and was gently rubbing it up and down. Fifi shook,
not daring to look at his boss, who was now moaning softly to himself.

After a few minutes, during which Fifi tried to stand as still as he
could, Mr. Walker tossed the bedsheets off himself with his left hand
and gave a gentle pull on Fifi's leg with his right. The maid tried to
stay upright, but he was off-balance and fell forward. At first he
managed to hold himself up by putting his hands down on the bed on the
other side of the prone Mr. Walker, but the older man quickly took the
opportunity to pull Fifi all the way down on top of him.

Fifi was now across Mr. Walker's lap, and he wondered if he was about
to get spanked again. Mr. Walker held him down with his left, and Fifi
didn't dare struggle. With his right, Mr. Walker began fondling Fifi's
ass again. It wasn't long before the maid felt the bulge growing inside
Mr. Walker's pajamas.

When Mr. Walker was satisfied that Fifi wasn't going to fight back, he
stopped holding him down and brought both hands to the young man's ass.
Fifi was face down on the bed, his rear end and high-heeled feet in the
air. He felt his panties being pulled down in the back, and presently
Mr. Walker's hands were manhandling his bare ass cheeks. He spanked him
a couple of times, but Fifi knew this was very different from the
punishment from two weeks before.

Then the terrified sissy felt a finger circling his hole, then gently
probing it. Frank had never even experimented with his asshole, but Mr.
Walker was gentle with the tight rosebud, only inserting the tip of one
finger. Fifi whimpered lightly, which only served to turn his tormentor
on even more.

The assault on Fifi's back door was put on hold as Mr. Walker took off
his pajama top, then quickly reached down to free his member, which was
now fully erect and slapped against Fifi's side.

"Get up on your knees and face me," said Mr. Walker.

Fifi scrambled to obey, and soon found himself kneeling beside his
boss. His gaze was inevitably drawn to the hard cock, standing fully at
attention. Frank was himself quite well endowed, but Mr. Walker's
erection looked huge to him, and he knew it was much thicker than his
own. Mr. Walker took his pants all the way off and lay there naked,
looking at Fifi.

"Touch it, Fifi. Hold it," he commanded in a low voice.

Fifi shut his eyes and shook his head no.

"Do it, Fifi," said Mr. Walker, louder this time. "Don't make me punish
you."

Still trembling slightly, Fifi reached out a manicured hand and grabbed
the big cock, as lightly as he could. Mr. Walker sighed contentedly and
sank back into his cushions. He put out his own hand and caressed
Fifi's arm.

"Now stroke it, slowly."

Fifi did. He could feel the member pulsing as he stroked it, up and
down. Then, Mr. Walker's hand was on his shoulder, and he was pushing
him down. Fifi tried to resist, feebly.

"Come on, Fifi, just do it," said Mr. Walker, just above a whisper.
"Give it a lick."

A drop of precum had formed on the tip. Ever so slowly, Fifi stuck his
tongue out, bent down further and flicked it off. He was disgusted to
find himself thinking that it tasted surprisingly pleasant.

After that, Fifi just held his position, his boss's throbbing cock in
his hand, waiting for the push he knew was coming. Sure enough, Mr.
Walker moved his hand up to the back of Fifi's head and gently but
firmly guided it down. Fifi shut his eyes as he opened his mouth and
let the monster in. He took the first several inches in and wrapped his
lips around it. He had a second to take in the musky smell before Mr.
Walker pushed down on his head, leading it further down. Fortunately,
he let Fifi partway up before he gagged, and soon the maid was bobbing
his head up and down on the big shaft.

Mr. Walker didn't seem to mind that Fifi was only taking slightly more
than half his member in his lipstick-painted mouth, and he continued
moaning as he kept firmly leading his employee up and down the length
of his cock. Fifi just tried to concentrate on breathing through his
nose, and all he could see was the fake blond hair of his wig as he
gave his first blowjob.

Soon Fifi's jaw was tiring as his mouth was stretched around the thick
cock. He could sense that Mr. Walker was getting close to cumming, as
he started thrusting up into Fifi's mouth and pushing his head downward
more forcefully, making him gag once or twice. Finally, Mr. Walker held
Fifi's head fast in place with both hands as he started ejaculating
into the sissy's mouth.

"Oh yeah," he grunted. "Swallow it, bitch, swallow it all."

Fifi obeyed, almost gagging again on the awful taste of what felt like
several days' worth of cum. Finally Mr. Walker let go of his head, and
Fifi just knelt there, completely defeated and emasculated, and too
emotionally drained even to cry.

"Good girl, Fifi," said Mr. Walker. "Now clean me up."

Feeling numb, Fifi obeyed again, squeezing every drop of cum out of Mr.
Walker and licking it all up. There was no longer any need for Mr.
Walker to force Fifi down, and he sat back with his hands behind his
head, enjoying his triumph over the younger man.

When that was done, Mr. Walker turned businesslike again, instructing
Fifi to clear the breakfast dishes and giving the unwilling maid
further instructions for the day. When Fifi forgot to curtsy, Mr.
Walker gave him a warning, and just like that Fifi was back in his maid
role for the day.

*****

TWO MONTHS LATER

It was a Thursday evening, and Frank was at an after-work happy hour
with several coworkers. As the evening wound down, Frank found himself
face to face with Shelly, looking as sexy as ever. They made small talk
for a bit, until Shelly said playfully, "You know, I was a little
disappointed you never asked me out."

Frank mumbled something in return, but he was saved from having to make
an excuse by the arrival of Evan, his fellow sales rep, who walked up
to Shelly and put his arm around her.

"You ready to go, babe?" he said.

She replied in the affirmative, and they shared a quick kiss, then a
longer, deeper one, giggling like schoolchildren. They said good night
to Frank and walked out. Frank wistfully watched Shelly's perfect ass
in her tight jeans as she walked away, and figured he'd probably jerk
off thinking of her tonight.

Evan had asked her out a few weeks earlier, and they had hit it off
right away, instantly becoming the "it" couple in the office. Frank
knew that could have been him, but he was too terrified of making his
move given his obligations as Fifi, which now took up all weekend.

While Evan got to enjoy Shelly's body on the regular, Frank didn't know
when he'd ever be able to have sex with a woman again. As Fifi, on the
other hand, he was getting more sex each weekend.

That Saturday morning, as usual, he would be driven to Mr. Walker's
house, where he would change into one of three maid outfits that were
now available to him, do his makeup flawlessly and make sure his wig
looked perfect. Then, he would spend the next two days as Mr. Walker's
sissy slave, performing secretarial duties, cooking, cleaning and doing
laundry and anything else his boss could think of, including the most
recent addition, toweling him completely dry after his shower. Fifi had
mostly avoided punishment, and had received only two more spankings,
which didn't fail to leave him in tears.

Blowjobs had become a regular part of the job, up to four or five each
weekend. One on Sunday morning, after breakfast in bed, was mandatory,
and at any time now Mr. Walker could order Fifi to drop to his knees,
unbutton his pants and suck him to completion, swallowing every drop of
cum. So far, Fifi had sucked his boss's cock under his work desk, on
the couch while he watched TV and under the table as he ate dinner.
Adding to his humiliation, Mr. Walker would often compliment him at how
good he was getting at it, to which Fifi was forced to reply with a
curtsy and a, "Thank you, Mr. Walker."

The boss had also stepped up Fifi's anal training. He could now stick
two fingers in the sissy's ass quite comfortably, and Fifi knew it was
only a matter of time before Mr. Walker started fucking him regularly.
Perhaps this would be the weekend that he had his sissy cherry taken.
Fifi's dick tingled at the thought.


THE END