Wicked and Tricked Waitress (mf, cons)
By: Date: 2024.07.11. Categories: Sex Stories Tags: , , , ,

Jack Talbot inspected his face in the mirror and smiled. A
genuine, honest smile. Life was good to him now. On the brink of
bankruptcy only two weeks ago, the deal he was about to close
with Zorin Industries would save his small company. Just a few
details needed to be sorted out and he’d hold the signed contract
in his hands by the end of the week.

He adjusted his tie for the third time in two minutes and smiled
again. Saved! He had saved his company. Was about to save his
company, he corrected himself. The contract wasn’t signed yet.

Right, he thought, back to work!

He pulled the door open and stepped out of the men’s room into
the narrow hallway that led from the restaurant to the restrooms
and the kitchen. Jack had been surprised when Mr Kilton had
suggested the small Five Oaks Grill & Bar on the outskirts of
town for their meeting. But Mr Kilton was the guy who’d sign the
contract; he would have agreed to meet him in Greenland if that’s
where he wanted to meet.

Jack saw the wisdom of the choice, though. The food was
excellent, the place was quiet and comfortable, and wasn’t
usually frequented by the business crowd, so his meeting with Mr
Kilton and Miss Miles, his assistant, wouldn’t be the subject of
his peers’ gossip.

He walked along the corridor casually and allowed his thoughts to
wander. Miss Miles. Her stunning body and elegant dress, her
quick wit and sexy smile had fascinated him. He fantasized what
it would be like to take her in his arms and kiss her and undress
her and … But that would be unprofessional.

Keep your hands off your customers, his mentor had warned him
time and again. There were three billion women in the world, he
had told him, don’t mess with your customers. Jack smiled as he
remembered the one time he had pointed out that not all of these
three billion women were available, while his customers were. The
result had been a 20-minute lecture on professionalism that had
left his ears ringing.

Jack had followed his mentor’s advice. Reluctantly at first, but
over the years he had come to agree that he had been right. He
had seen many consultants whose affairs with customers had cost
them dearly in terms of lost contracts and cancelled accounts.
Jack was determined to keep his distance from Miss Miles.

“Watch out!” A high-pitched female voice interrupted his reverie.
Just as he was about to round the corner and walk back into the
restaurant, a waitress came from the opposite direction.
Fortunately she wasn’t carrying anything, or their collision
would have caused a major mess.

“I’m sorry,” he apologized, highly embarrassed. “I was
daydreaming. You’re not hurt, are you?” Jack sized her up quickly
while she took half a step back. Her outfit was standard for
waitresses in this kind of restaurant — white blouse, black
skirt, black stockings — except for her tight miniskirt, which
ended about four inches below the voluptuous curve of her ass. He
remembered seeing her in the restaurant, but had been too busy to
pay her any attention.

“I’m okay, no problem,” she said softly and smiled, her pale blue
eyes sparkling with amusement.

Jack relaxed. No damage done. “I’m sorry,” he said again and
returned her smile. He was about to step around her when all of a
sudden he felt her hand between his legs. His eyes went wide and
his smile faded instantly, but he was too shocked to move. Her
hand rubbed up and down his dick, gave it a final squeeze and
retreated. Then the waitress walked past him with a little finger
wave and disappeared around the corner in the direction of the

Jack was horrified. He took a deep breath and willed his dick to
relax, but it kept growing. He stared in disbelief at the bulge
it was making in his pants and frantically considered his
options. Walking through the restaurant like this was out of the
question. And what about Miss Miles? If she thought he was hot
for her … And what would Mr Kilton think? Sprouting an erection
during a business meeting! No doubt he’d question his

The consequences were too horrible to contemplate. The contract
he had worked so hard for … His company, whose very existence
depended on it … Bankruptcy … All because of a stupid
waitress playing stupid games!

Jack turned on his heels and walked back to the men’s room. He’d
jerk off and return to their table looking … professional. Too
bad he had to keep them waiting, but apologizing for the delay
would be a lot easier than explaining an obvious bulge in his

He pushed the door to the men’s room open and froze in mid-
stride. His jaw dropped and his emotions went from shock to anger
to naked animal lust in less than a second.

“What took you so long?” the waitress asked as the door fell shut
behind him. She was leaning against the opposite wall right next
to the paper towel dispenser, her blouse unbuttoned down to her
bellybutton, one foot against the wall and her leg turned
outward, her miniskirt stretched tightly around her slender legs.

Her exposed tits attracted his gaze like a magnet. He watched
with rapt attention as she squeezed them lightly with her hands
and pinched her nipples, making them stand up proudly. His dick
throbbed painfully in his pants, reminding him why he had come
back to restroom in the first place.

“What the fuck do you think you’re doing?” he demanded. His anger
at her for jeopardizing his contract with Mr Kilton, his very
future, was gaining the upper hand over his lust, at least

She glanced at the bulge in his pants and gave him a bright
smile, whose apparent innocence was in odd contrast to her
posture. “You were going to jack off, weren’t you?”

Jack was too flabbergasted to reply. She took his silence to mean
Yes and pulled her skirt up slowly, revealing the creamy skin of
her thighs above the top of her stockings.

Jack gasped and stared at her crotch as the hem of her skirt slid
farther up until her naked pussy was completely exposed. No more
than five feet in front of him, her shaved pussy lips were red
and swollen and slightly parted. He watched in disbelief as she
bunched her skirt around her hips and slid one hand towards her

“Come on! This is a lot better than jacking off!” The waitress
smiled her sexy smile again, a trace of mockery creeping into her
pale blue eyes now. She looked him straight in the eyes while she
toyed with the tiny triangle of dark blond pubic hair that seemed
to point the way to the promised land.

Jack was dumbstruck. All he could do was stare at her hand as her
bright pink fingernails edged closer to her labia and her middle
finger finally disappeared between them. Did she really expect
him to screw her right here? “What if somebody comes in?” He
almost choked on his question.

The waitress just shrugged her shoulders and pushed her middle
finger into her pussy past the second knuckle. “They’ll have to
stand in line. Now fuck me before your dick rips a hole in your

That would be fun to explain to Mr Kilton and his assistant, Jack
thought and laughed despite his anger at her. His daze broken, he
quickly unzipped his pants and freed his aching dick. She had
caused the problem, he rationalized, so why shouldn’t she solve
it? Besides, she clearly wanted to get fucked.

The waitress wrapped her arms around his neck as soon as he
stepped forward. She pulled herself up until her pussy was level
with his dick and looked him in the eyes. “Now we’re getting
somewhere,” she purred. “Stick it in!”

Jack would have preferred to drag her into one of the stalls, but
his need to get off was so urgent by now that he really didn’t
care where they did it. He maneuvered his dick until the head
found the entrance to her well-lubricated vagina, then drove it
all in with one hard thrust of his hips.

“Yeah!” the waitress hissed. “Fuck me!” Squeezed between Jack’s
body and the wall, she wrapped her legs around his waist and took
his dick as deep as she could.

As soon as her tight pussy enveloped the entire length of his
dick and squeezed it like a velvet glove, Jack lost his self-
control rapidly. He jerked his hips back and forth furiously,
thrusting into her with hard and fast strokes that made her moan
each time their hips collided. He wanted to come as soon as
possible and didn’t care if she would climax or not. Stupid
chick, he thought, shouldn’t have messed with me in the first

He didn’t bother to warn her before he came, but she was ready in
any case. When his dick expanded slightly in her tight pussy and
released the first spurt of cum into her, she exploded in an
orgasm of her own. She buried her face in his shoulder to stifle
her screams of pleasure and jerked her hips repeatedly while her
pussy muscles squeezed the cum out of his dick.

Jack held her against the wall and pulled his dick out of her
pussy as soon as his orgasm subsided and his breathing returned
to normal. He yanked a paper towel out of the dispenser and wiped
the juices off his dick while the waitress was still leaning
against the wall, enjoying the last waves of pleasure that
radiated out from her hot pussy and raced through her body. He
stuffed his deflating dick back into his pants and zipped up,
smiling for the first time since his fateful collision with her.
On the way out he stopped briefly in front of the mirror and
adjusted his tie.

By the time he reached his table, his optimism had returned. “My
apologies for taking so long,” he excused himself as he sat down.
“I had a little problem back there.”

Miss Miles raised an eyebrow inquisitively.

“Well, in case you’re curious,” Jack smiled sheepishly, “my
shirttail got stuck in my zipper and I had one heck of a hard
time freeing it.”

Mr Kilton smiled briefly, but didn’t seem very interested in his
explanation. “Whatever. You solved the problem, that’s all that
counts.” He shuffled his papers around and glanced at his notepad
briefly. “We’re about done anyway. I have only one minor point to
discuss and then we’re ready to sign your contract day after

Jack Talbot suppressed a violent urge to jump up and dance around
the restaurant with joy.

He had done it! He had saved his company!

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