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Gillian searched desperately for a street sign.
She was on Akard, a one-way street with many stoplights. Traffic
moved at a slow pace, stopping frequently. To top it off she was stuck
behind a semi and couldn't see the street signs ahead. She could see
the top of the skyscrapers ahead, but where was Pacific? She moved into
the right lane. A van honked behind her. She waved, glancing at
the huge driver in her rearview mirror. He was mad.
This was turning out to be the worst day of her
life. Suddenly she saw the sign above the street and turned.
Thank God, there was less traffic. Now to find the building.
Dallas was a confusion of one-way streets. It was easy to get
lost. Would she ever find her way back to highway 75 in all this
Gillian took the elevator up to the 23rd floor.
Her knees were shaking as she waited for the doors to open. Would
she get this job? She had tried dozens of times before, but
nobody wanted to hire somebody her age. She was getting
desperate. The doors opened and she stepped into an empty
hallway. She saw nothing significant in either direction except
anonymous doorways. Gillian took the sheet of paper out of her
purse and stared at the directions. Door number 27. She turned
left and found the door in seconds. She turned the knob and
stepped inside. A handsome man in his 40's stood and stepped
forward with a happy smile.
"Gillian?" he asked gaily.
"Yes, you must be Bill."
"Right the first time," he said with a heavy Texas
accent. He shuffled her forward into a chair beside his desk.
He pulled her chair over before her and sat with his hands in his
lap, his eyes traveling over Gillian's body. "Let me be brutally
honest and come right to the point, Gillian," he said in an
intimate manner. "I've had seven women come thorough the door
today," he pointed at the door behind her. "They have all failed
to meet my needs. Do you know why?"
"No, sir, I don't," Gillian said with her heart
"Because they just don't have what I want. They
are fine, up to a certain point, but they just don't go far
enough. Do you see what I mean?" he asked with his face just
inches from her's.
"N... no, I don't understand," Gillian said
"I'm looking for more than a secretary, more than
a receptionist. I'm looking for all those and a companion. Are
you willing to go that far, Gillian?" he asked, placing a hand on
her knee. Her immediate reaction was anger. She wanted to slap
his hand away and storm out of the office. Then she remembered
how hard it was for a 48 year old woman to get a job in
"I... I understand," she said, swallowing
"Good, great, Gillian. Now the first thing I want
to do is see what you've got and how cooperative you can be.
That entails taking off your clothes and putting on this suit," he
said, holding out two strips of lycra. "Consider it an
Gillian was very nervous. Her impulse was to run
out of the office as fast as she could run, then find a cop. But
hunger was a strong emotion. Besides, why the hell should she
care, she liked to fuck as much as the next gal. Screw it, she
would do this and anything else he wanted. She could always sue
him for sexual harassment later.
Gillian stood and calmly undressed. Bill moved
over to a nearby couch to watch. He had an eager, breathless
look on his face, like a young boy with a new toy. Gillian's
suddenly stopped in the act of putting on the lycra suit. He
whistled in appreciation as her full, ample breasts fell from her
"How much does this job pay, and do I have the
job?" she asked.
"I will certainly let you know after seeing what
the next few hours bring," he said eagerly. "Put it on," he
nodded at the plastic panties.
"No. I want some assurance that you are not going
to fuck me and toss me out. How much does the job pay and do I
have the job?" she insisted.
"Gillian, if you go through with this today, and
any other time I feel the need for companionship, you will
certainly have the job. I will start you at 25 dollars an hour.
To tell you the truth I had a secretary for over three years.
She would dress sexy as hell, show her panties a dozen times a
day, and bend over to give me a tit shot. But the moment I tried
to make a move on her she got all sanctimonious and belittled me.
I had enough. I fired her. Then I was thinking, what I need
is to hire exactly what I want. What I wanted was a woman close
to my own age, with some experience and no husband. I wanted a
woman who would bend over and drop her drawers when I told her
without question. Hell, I own a multi-million dollar company,
why shouldn't I enjoy my work?"
Gillian thought for a moment and nodded. She
managed to put on the lycra blouse and was about to snap the
crotch on a unique contraption to form a pair of panties, but he
"Wait, turn around and show me your butt," he
She licked her lips nervously, but did as he
asked. She knew her ass was not her best asset, but it was cute
for a woman her age.
"Climb up on the desk and bend over. My God, look
at that," he said breathlessly. She could hear him moving
closer. He knelt behind her and ran a hand over her unblemished
rounded cheeks. She felt him sniffing her pussy and resisted the urge to
giggle. "That is the most beautiful ass I've ever seen," he said
before kissing her right butt cheek. She shivered under the warm
"Would you let me fuck you in the rectum, Gillian?"
he asked in a whisper.
"Yes," she said simply. She was shuddering in
excitement. She felt like she was in high school
with the first boy who had fucked her. She had lost
her virginity in the back of a 1968 Cougar. She was now about to
lose her anal virginity on the 23rd floor of an office building
in downtown Dallas.
As Bill's tongue touched Gillian's puckered
asshole she squealed and shot forward on the desk. He pursued
her, pressing his puckered lips between the cheeks of her ass and
rimming her delectable asshole. She felt fire spreading from her
rectum outward. She mashed her tits in her hands, with her face pressed
against the cold shiny surface of the desk.
"Roll over," he whispered after giving her butt one
final kiss. Gillian decided that what had occurred so far had
made the trip from New Orleans worthwhile all by itself. This
was becoming very exciting.
She rolled over on her back and noticed that Bill
was now naked. He had a short fat cock. At the moment it was
standing at attention, just inches from her asshole. Bill
smiled, spit into his hand and rubbed the end of his cock. The
movement made a slick wet sound. She felt so excited that she
Bill held one of her legs in the air with his left
hand, and guided his thick cock toward her anus with the right.
He was moaning with each breath. She could see that he was as
nervous as she was. His cock touched her rectum and she cried out.
He smiled and looked down at his cock as the head pressed against
her ass. He applied more pressure and she could feel it
spreading the ring of her asshole with great pressure. She
whimpered slightly, but pressed her anus back toward him. He gave
a few shuddering thrusts toward her ass and the head suddenly
slid inside. Gillian screamed and grabbed at his cock. But he
had stopped and was simply waiting for her anus to stretched to
Gillian felt like a wine bottle had been shoved up
her rectum. She wondered if she was bleeding. What if she needed
stitches? How could she ever show up at the hospital and explain
what had happened? Gillian was suddenly aware that his cock was
sliding further inside her. She whimpered fearfully, but there
was less pain. Her asshole had miraculously stretched. It
seemed hours, but was only a few minutes until Bill began
plunging in and out of her butt while he breathed harshly above
Bill reached out and mashed her firm breast in his
hand, as he pumped steadily into her anus. His cock was sliding
smoothly well up into her anus now. She felt a fire building
deep down inside her. The fire was spreading to her loins.
The fire was building in her ass, but she needed
relief in her pussy. She started to reach for her pussy, but he
slapped her hand away.
"Wait," he whispered in a grunt. She felt like
crying, but she had to obey him. He fucked her for several more
minutes, then paused.
"On your knees," he commanded. She turned and
knelt on the cold desk with her head down. He climbed up on the
desk behind her and shoved his fat cock inside her gaping
asshole. She screamed and tried to jerk away, but he grabbed her
butt and held it in a firm grip. In a moment she no longer wanted
to pull away. His cock in her rectum felt heavenly. But she needed
relief and being fucked in the ass would not give it too her.
Was it a test?
"Oh fuck," Bill moaned above her. "You have such
a sweet little backside," he said as his hips hit her ass with a loud
smacking sound. She realized that her knees were beginning to
hurt. At first she could ignore the pain because of the pleasure
emanating from her asshole. But soon it became too much to
"My knees hurt," she whispered, hoping he would
not become angry. He pulled out of her rectum wordlessly and pushed
her to the edge of the desk. He laid on the desk face up and
waited. She quickly crawled over his prone body and started to
lower her pussy over his cock.
"Not yet," he cautioned her with the shake of a
finger and a smile. He repositioned her plump ass until her
asshole touched his cock. He pulled her down roughly, impaling
her anus on his cock. He moaned, feeling an orgasm begin deep
down in his balls. He knew it wouldn't be long.
"My pussy is starving for attention," she begged
as she bounced on his fat little cock.
"Not yet," he said with a twisted face. "I have
never fucked an ass before. I want to cum in your butt," he
nearly shouted, feeling his orgasm give a few false starts as the
heat built in his balls. "NOT YET!" he screamed again louder.
"NOW!" he cried. Gillian felt his hot cum spurting up into her
rectum. It was a good feeling, hot and somehow satisfying. She
felt the pressure build in her as a huge ball of cum
collected inside it. She again reached for her pussy, but he grabbed
her hand and pulled it away. She sat motionless in defeat,
watching the emotions twist his once handsome face into a
withered mask. Slowly he relaxed and slumped down on the desk.
He turned and pulled open a drawer. He pulled out a box of
kleenex and a huge oddly shaped dildo. He handed the dildo to
Gillian and pulled a handful of kleenex out for himself. He held
them around his cock and lifted her. She pulled off his cock.
He handed her the box of kleenex and sat up on the edge of the
As Gillian cleaned her tortured butt with the
kleenex, Bill wiped his cock and sat in the desk chair with a
"Now," he said quietly. "I've only seen a woman
fuck herself with a dildo once in my entire life. It was the
most erotic thing I have ever seen. Now that I've made you hot,
make yourself cum."
Gillian hurriedly turned on the vibrator and laid
on the desk. Fully aware of his lustful eyes on her, she slid
the vibrator up inside her pussy with a squeal of delight. The
dildo had two heads, one large head for her pussy, and a smaller
one for her ass, or to stimulate her clit. She chose to insert
the smaller head into her anus, increasing the fire he had already
started there. She pulled the dildo up inside herself with sure,
brutal strokes. The vibrations seemed to fill her ass and travel
up her spine. She used her left hand to reach down and stimulate
her clit. She was in heaven. She felt very hot and sexy under
his adoring, lustful eyes. She had never felt so wanted in her
She arched up off the desk with her pussy in the
air. She jerked the dildo down inside her moist hole, crying
with each stroke. The fire was unbearable. Her entire body was
on fire. Even her neck tingled. She hunched against the dildo
harder, feeling her loins glowing with the beginning of a
horrendous orgasm. She knew it would be devastating and all-consuming. She feared the impending orgasm, but craved it at the
"Oh fuck," she gasped. Her eyes flew wide with
horror. Bill moved closer to the desk so he wouldn't miss a
thing. He looked down in his lap in surprise and found his cock
again had a raging hardon. This was one hot little bitch, and
she was all his.
"Oh yes!" Gillian yelled. She grunted several
times, stiffened with a frightened glance toward Bill, then
screamed as the orgasm began throbbing in her loins. She felt
her pussy muscles clenching and unclenching around the dildo.
She threw here head back and trashed from side to side. She
swore and grunted as she withered on the desk, then suddenly sat
up and grabbed for the dildo. She jerked it out of her sensitive
pussy and fell back in exhaustion. Eventually she twisted the
base and turned it off.
"My God," Bill said reverently. "That is the
sexist fucking thing I've ever seen. You are hired, Gillian," he
said, leaning forward and kissing her breast. She shivered at
the contact. She rolled over slowly. He slapped her butt cheek
and jumped to his feet.
"Get dressed," I'm hungry. "Well take the rest of
the day off to celebrate," he said as he pulled his clothes
"I'm going to love working here," Gillian said as
she slowly began to dress.
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