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Dinner with the Boss by Crowbar, crowbarstories###
“Harold Simmons?” asked the secretary.
“Yes,” answered Harold.
“Mr. Grant would like to see you in his office. Please follow me.”
“Mr. Grant? Why me? What did I do?” babbled Harold.
“Just follow me please,” the secretary told him.
Harold got up and stumbled behind the secretary. She was definitely
69th floor. He had never really seen one before, but he had heard rumours
about them. Secretaries that could double for supermodels. They wore
short skirts, skin tight shirts and high heel pumps.
Harold followed her into the executive elevator. It was his first time
inside it after working here for six years. He was scared shitless. Mr.
Grant was VP of human resources and known as “the reaper” at the water
cooler. Harold starred at the secretary as the elevator rose. He could
now see that she wore no bra beneath her tight fitting top. Her nipples,
poking through, also appeared to be pierced.
“See anything you like?” she asked.
Harold quickly starred at the floor. “Sorry. I’m just nervous.”
The elevator hit the 69th floor and the doors opened. Out walked the
secretary and Harold followed her. She showed him into a large office and
told him to sit down in the chair opposite the desk. “Mr. Grant will be
right with you.”
Harold sat waiting for about five minutes when Mr. Grant came in. Mr.
Grant was tall, handsome, about 50 and dressed in a very smart blue suit.
“Mr. Simmons, I won’t waste your time. Could you please tell me who
this is?” Mr. Grant held up a picture of a woman.
“Why, it’s my wife sir. That picture was on my desk. I didn’t even
know it was missing.”
“This is a copy. Does she work?” asked Mr. Grant.
“Then it would be a shame if you lost your job, wouldn’t it Harold? Now
before you start grovelling, let me say you are hanging by a thread. I am
coming over to your house for dinner tonight. If I can find no reasonable
cause to excuse your mediocore performance in the workplace, I will be
forced to let you go. Is that clear?”
“Yes sir. Thank you for the second chance sir.”
“And Simmons? Please make sure your wife dresses nicely. I’ll be there
Harold scrambled out of the office and rode the elevator down to the 8th
floor where his office was. He called home to his wife and explained the
situation. Trish said she would try to make something special for dinner.
Just before he hung up he asked his wife to wear her short black dress.
She was about to question him about it, but the line went dead.
Harold was trying to think it through. Why would Mr. Grant have a
picture of his wife? Harold had married Trish two years ago. They were
home town sweet hearts. She was three years younger that him at 23.
Harold worried about it all day and all the way home, until six o’clock.
At six, the door bell rang. Harold answered it and welcomed Mr. Grant
inside. “Yes, yes, Simmons. Where is your wife?”
“She’s just finishing up in the kitchen sir. Right this way.” Harold
led Mr. Grant to the kitchen. “Mr. Grant, this is my wife Trish.”
Mr. Grant took a good long look at Trish and nodded in approval. “Very
nice. You could be 69th floor material with a little work.” He put his
hand on her back and ran it down to the bottom of her short black dress.
He quick put his hand up her dress and felt her panties. “Cotton. I knew
Trish looked startled towards Harold. Harold didn’t know what to do.
He couldn’t lose his job. He didn’t say anything and simply shrugged his
“Harold, go fix your wife and I a drink,” Mr Grant told Harold. Harold
left for the den to make some drinks. “Do you know why I’m here?” Mr Grant
“For dinner?” asked Trish meekly.
“Fuck dinner. If you want your husband to keep his job, you had better
just do what you’re told tonight. Understand bitch?” With his last word he
gave her long blond hair a sharp tug.
“Yes,” whispered Trish.
Harold came back into the room carrying drinks. “Harold, finish cooking
dinner. Your wife is going to give me a tour of the house.”
“Yes sir,” said Harold as his wife and Mr. Grant left the kitchen.
“Let’s start upstairs. You first,” said Mr. Grant. Trish led him up
the stairs. As they climbed Trish felt Mr. Grant’s hands groping her ass.
“You’ve got a great ass bitch. We’re going to have some great times.”
Trish began to sob as she reached the top of the stairs. Mr. Grant
walked past her and into one of the rooms. “The bedroom I see. Come in
here bitch.” Trish followed him into the room. “Now, I like your dress;
it’s very slutty. But you need to lose the underwear and the bra. Take
them off now.”
Trish whimpered as she pulled down her panties and then she nimbly
slipped out of her bra. “That’s better cunt. Now I can see and feel your
nipples through the dress.” He groped her tits through the dress.
“Let’s see your slit. Pull your dress up to your waist bitch,” he told
her. Trish pulled up her dress to expose herself. “Oh, fuck. Look at the
bush. We need to fix this right now. Come in here bitch.” He led her into
the ensuite. Mr. Grant found Harold’s razor and shaving cream on the
counter and said “Here. Shave that thing right now.”
Trish pleaded with her eyes, but Mr. Grant told her to quit stalling.
Trish ran some warm water and soaked her bush with it using a sponge. Then
she lathered in some shaving cream and began shaving. It got easier as she
went, but it was terribly embarrassing with Mr. Grant watching her.
Surprisingly, she found herself aroused at the site of her shaved cunt.
She tried to remind herself what a degrading experience this was.
Mr. Grant began running his hands over her cunt as she stood in front
of the mirror. “Doesn’t that feel nice, bitch? Watch me pull you open,”
he said prying the lips of her cunt apart with both hands. She watch as he
lewdly pulled her open. She found her arousal only increasing and her
moans betrayed her. “Well, well. The cunt really does want it.” He
slipped two fingers into her wet slit.
“Oh god… Don’t, this is wrong… Please stop,” moaned Trish.
“You’re pretty tight bitch. That husband of yours must have the world’s
smallest dick. Tell me what you think of this one,” said Mr. Grant as he
pulled out his cock to show her. Trish nearly fainted at the site of it.
It was huge, and it was still growing. Trish guessed it was about fourteen
inches long and as thick as the large end of a beer bottle. This made it
about three times the length and twice as thick as Harold’s.
“Oh my god! That can’t be real, that’s too big. Look at it!” was all
Trish could say. She seemed hypnotized by it and couldn’t take her eyes
“That’s right bitch. Fifteen inches of solid cock, all real. And
you’re the lucky cunt that is going to get ploughed with it tonight,” Mr.
Grant told her.
“Oh no, I couldn’t! Harold would never forgive me. I just couldn’t
fuck your big cock,” Trish breathed heavily. As she stared at it, Mr Grant
brought his enormous dick up close to her face. Trish put a hand on it and
could feel it throbbing. “It’s so big… It’s such a beautiful cock…
Harold’s is so small… Maybe I could just have a quick suck…” And she
found herself cramming the head of the cock into her mouth.
“That’s it bitch. Get a little taste of what’s going to fuck your
cunt,” grunted Mr Grant. But it was all Trish could do to get the first
three inches inside her mouth; it was just too big. “Here let me help
you,” said Mr Grant. He held the back of her head as he thrust his cock
into her face repeatedly. At first Trish bean to gag and then she had
trouble breathing. She began to feel light headed and thought she might
pass out, but she suddenly realized that relaxing her throat and jaw
muscles allowed the hue dick much freer access to penetrate her mouth.
Soon, she had received about twelve of Mr. Grant’s fifteen inches inside
her. Mr Grant continued to pound her face as she tried to let the cock
slide further down her throat. She was just getting the last inch thrust
into her when she heard Harold’s voice from downstairs.
“Dinner’s ready,” he called.
Mr. Grant pulled his dick out of her face. “Looks like that shrimp
dicked husband of yours would like to see us downstairs. What do you think
we should do bitch?”
“I want to suck your big cock,” moaned Trish.
“Yes my dear, there will be plenty of time for that. But let’s go down
to see poor Harold.” Mr Grant fastened his pants and turned to leave the
room. Trish straightened her dress and followed. Downstairs, Harold had
put dinner on the table. He had put the three place settings on three
sides of the table. “Your wife afforded me a most accommodating tour,
“I’m glad you liked it sir. It’s just a small house, nothing really
special.” Harold sat down across the table from Mr Grant. Trish sat at the
side of the table between the two men.
“Let’s eat. Your wife was just telling me how hungry she is. She is
very pretty; you must have battled many suitors to claim her,” said Mr
Grant. Trish blushed.
“Well, not really sir. We came from a small town and grew up together.
I guess it just seemed natural for us to get married,” Harold told him.
“Aren’t you afraid a hottie like Trish will be hit on by other men now
that you’re in the big city? She might be tempted away from you,”
suggested Mr. Grant.
“No sir. I know Trish better than anyone and I trust her completely,”
Harold told him.
“That’s great, Harold. Oh, Trish? I’ve dropped my napkin under the
table could you please get it for me?” Mr Grant asked.
“Yes sir,” said Trish and dropped to her knees to find the napkin. She
found it quickly and was about to get up and return it to Mr Grant when she
noticed that Mr Grant had pulled his cock out of his pants and it was
sitting on his chair between his legs. Trish slid over to it and quickly
popped it in her mouth. She quickly began working it in, deeper and
“You have to watch it Harold. Many wives turn out to be sluts that will
suck any big dick that’s put in front of them,” Mr Grant told Harold as
Trish continued to pump her head up and down on his cock. “I’ve seen it
happen to our employees. Sometimes the sluts will do it right under their
“Well, I think I’m pretty lucky to have Trish sir. She’s pretty shy
when it comes to sex, so she’d probable just run away from any of those big
dicks. Where is she? Trish, did you find that napkin yet?” Harold looked
under the table and saw his wife on her knees near Mr Grant with the napkin
in her hand. “Good girl, now give it back to Mr Grant and finish your
Mr Grant reached down to take the napkin from Trish with one hand, while
he held her head on his cock with the other as he pumped his load of cum
into her mouth. “Thank you Trish,” he grunted. Trish swallowed
everything, crawled out from under the table and got back into her seat.
“Trish, honey? You’ve got some of the cream sauce on your face, you
might want to wipe it off,” said Harold. Trish reached up and felt a
sticky wad of cum on her chin. She scooped it with her finger and licked
When everyone was finally done with their meals, Trish offered to clear
the table. “It’s really good that you trust you wife Harold,” Mr Grant
told him. When Trish went out of the room he continued, “You must really
satisfy her. Is she good in bed?”
Harold blushed and stammered “Yes, she’s good.”
“She must give great blow jobs. She really seems to have the lips for
it,” said Mr Grant.
“Well, she’s never actually done that, but she’s very good at other
things,” Harold told him.
“How about ass fucking? I’ll bet she cums like a banshee. Does she
have a tight asshole? ” asked Mr Grant.
“Oh no, sir. We would never do anything like that. Trish is very
satisfied with our sex life. I am absolutely positive I have nothing to
fear,” Harold said. “Why don’t we go into the living room for coffee and
In the living room, Mr Grant sat in a lounge chair while Harold sat on
the sofa. Trish brought in a tray of pie and coffee. “Trish, you must be
telepathic, because I was just thinking about having some pie,” said Mr
Grant. “I also just noticed how much you resemble my niece. When she was
little, we used to have so much fun together. She would sit in my lap and
get pony rides. Come here and sit in my lap Trish, I’ll give you a pony
ride, just like my niece.”
Harold watched Trish eagerly sit in the lap of Mr Grant. The old man
sure was peculiar, but at least he seemed to be having a good time. All
the questions about sex had certainly surprised him, but it was obvious Mr
Grant didn’t understand the type of wholesome trusting relationship he and
As soon as Trish was in his lap, Mr Grant leaned back, pulled out his
cock and lifted her up slightly to manoeuvre the head of it to the entrance
of her cunt. All this was masked to Harold by Trish’s body and the front
of her dress which she carefully held down. Trish began to rock herself
forward, trying to get the massive cock started up her cunt. Finally, with
a forceful shove from Mr Grant, the first four inches entered her wet
pussy. “OH!” she gasped.
“What’s the matter Trish? Are you okay?” asked Harold with some
Trish continued rocking and working more and more of the cock up her.
“Oh yes… I feel fantastic… I’m so full…” she said.
“Yes, it was a rather filling dinner,” admitted Harold.
“Would the little girl like the pony to go a little faster?” asked Mr
Grant. Trish had worked in the entire length by this time.
“Oh yes… It feels like a horse… Faster, faster…” she bounced up
and down on his lap. Harold thought it was all rather silly, but Trish was
certainly humouring the old man by showing some enthusiasm. He would have
to thank her later.
Trish felt like she was being fucked for the first time. It was
incredible. She didn’t care if Harold caught on. She probably wouldn’t
fuck him anymore anyway. She could feel her orgasm building. It would be
the first orgasm she ever had during intercourse. Harold had never
“Full gallop, coming home,” puffed Mr Grant.
“Yeah… yes… yes… I’m cumming… I’m cumming… Here I cum… OH
GOD, YES!” squealed Trish. Mr Grant blew his hot sticky load up her as she
“Well, that sure looked fun,” said Harold. “Can I interest anyone in
“Actually Harold, could you go make me some decaf?” asked Mr Grant.
“Oh yes sir. I’ll be right back,” said Harold
As soon as he was out of the room, Trish lifted herself off of Mr Grant.
“Clean me off bitch,” Mr Grant told her and she dropped to knees to oblige.
When she finished, he zipped up his pants. “Well cunt, my work here is
“Please, take me with you Mr Grant,” Trish begged. “I don’t want to
stay here with this wimp. You can fuck me with your big cock anytime you
“I will fuck you anytime I want, but you’re not coming with me. I’ll
just drop in and fuck you whenever I feel like it. Or maybe I’ll have you
brought to my office to fuck me and some of my big dicked staff,” he told
“But I want more of your big cock now,” she whispered.
“And you’ll get it. I still have to fuck that tight virgin asshole of
yours before I leave tonight,” he said.
“Oh my god! You can’t be serious! That thing will never fit. Please
don’t make me do that,” Trish begged.
“Shut up cunt,” Mr Grant told her.
“Ouch!” said Trish, pulling back from her coffee mug. “Damn, I got a
splinter from that cheap coaster. It’s a good thing there’s no blood or
Harold would probably faint.”
“Really?” asked Mr Grant. He got up and ran into the kitchen. “Harold!
Your wife got a huge splinter in her hand and its bleeding. Do you have a
needle I can use to get it out?”
“Oh my! Here you go,” said Harold, passing Mr Grant a large needle from
a drawer. “Use the bathroom sink!” he called after Mr Grant.
Mr Grant went back into the living and grabbed Trish and pulled her into
the bathroom and closed the door. “Bend over the sink bitch,” he told her.
She took a deep breath and did as he asked. Mr Grant pulled up the back of
her dress, pulled out his hardening cock and guided the head to her
asshole. He applied some light pressure. “Tell me what you want bitch.”
“Uh… I want your cock… I want that big cock up my ass… Fuck my
ass…” she told him. He began applying real pressure. “OH GOD! IT
HURTS! OH FUCK!! STOP! YOU’RE KILLING ME!” she screamed.
“Trish! Are you okay?” Harold’s voice was outside the door.
“There’s a lot of blood Harold. Come in and see, the door’s not locked”
Mr Grant told him.
“Oh my god! Blood? Maybe you better take care of it Mr Grant. I’m not
too good with blood,” said Harold. “Take good care of her.”
“I’ll do my best Harold. Stay close, I might need your help,” Mr Grant
told him as gave another hard thrust. The head of his dick popped into her
“NOOO! TAKE IT OUT! TAKE IT OUT! IT’S TOO BIG!” wailed Trish. She
buried her face in her hands and began whimpering. Mr Grant continued to
work his cock further in with repeated entry and exit to and from her ass.
He had worked about five inches in when Trish began slowly pushing back.
“It’s so big… Fuck, it hurts… That’s it…” she started moaning.
“Is it out?” Harold called.
“No Harold. I’m just getting inside. She’s bleeding quite badly, but I
think the worst of the pain is over,” Mr Grant told him. With Trish’s help
he had now buried ten inches of cock in her ass. Mr Grant suddenly pulled
out and sat down on the toilet. “Sit here,” he told her, indicating his
Facing Mr Grant, Trish pulled her ass cheeks apart as she guided her
asshole onto the massive prick. “Ohhh! Fuck! It’s really big Mr Grant!
Let me do it,” she said as she began to bounce up and down on his pole.
Three minutes later, Trish was grinding her asshole on the hilt of Mr
Grant’s cock. “Oh god! I can’t believe how far it’s in there! Look at
it, it’s covered in blood. It ripped me open,” she panted.
Mr Grant was breathing heavily too, “I’m almost there, jiggle it for
me… Oh, yeah… There it is…Uh!” Trish felt his warm cum shoot up he
“Are you done? Did you get it?” asked Harold through the door.
“Yes, we got it. We just have to clean up,” said Mr Grant guiding
Trish’s face to his cock which was coated in blood, shit and cum. She took
it into her mouth and swallowed everything. Mr Grant refastened his pants
and Trish fixed her skirt. “All done Harold.”
Harold opened the door and rushed in. “Are you alright sweetie?” he
asked Trish. She held up a band-aid on her finger.
“Well Simmons, I have to be going. Rest assured your job is safe for
the time being. You can thank your wife for that,” he told him. He went
to the door and put on his shoes and coat. “Trish, the pleasure was all
mine,” and he gave her kiss and he thrust his tongue in her mouth. When he
was done he left.
Harold closed the door. “Sorry about that honey. He’s a bit of a
weirdo. He seemed to have sex on his mind tonight. Thank you for saving
my job. You really humoured the old guy.”
“Anytime,” she told him.
“I don’t know what it is. For some reason, I’m really turned on
tonight. Maybe we could light a candle and put on some romantic music
tonight,” Harold suggested.
“Not tonight dear. I have a headache,” she told him. And she went
straight to bed.