Standard disclaimer applies. 


Dinner with the Boss
by Crowbar, crowbarstories@gmail.com


“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.

“No sir.”

“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 at six.”

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 it.”

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 shoulders. 

“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 asked Trish.

“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 away.

“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, Harold.”

“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 deeper.

“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 noses.”

“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 dinner.”

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 it off.

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 
dessert?”

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 Trish had.

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 concern.

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 satisfied her. 

“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 came.

“Well, that sure looked fun,” said Harold. “Can I interest anyone in more coffee?”

“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 almost done.”

“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 want.”

“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 her.

“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 asshole.

“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 cock.

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 ass.

“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.

END

