My new boss and the big gangrape

Michael and his co-workers had a pretty sweet operation
going before Ms. Wilson showed up. They were able to
forge timesheets, sales records, skim a little off the
top every once in while, but then the company hired Ms.
Peggy Wilson. Ms. Wilson started by “cleaning house” as
she called it. Four of Michael’s friends were fired
within her first week. Michael suffered a formal
counseling and cut in pay for lack of productivity. Ms.
Wilson required daily morning meetings and criticized the
men in the office about everything, including their

Ms. Wilson was tall, about five feet ten inches with
short, blond hair. It seemed to Michael and his buddies
that she always looked perfect. She never had a hair out
of place and just lightly made up. She always worn
women’s business suits to work with the skirts just above
the knee and Michael noticed she rarely buttoned the

Michael and his co-workers, all men, decided that was
probably because of her big tits. Sometimes during her
mandatory morning chastising, Michael would fantasize
about sucking those big tits. Michael hoped that in the
near future that would be a reality. Ms. Wilson was a
real bitch with an attitude about men, but Michael and
his buddies were about to change all that.

Ms. Peggy Wilson entered her office, smug as usual with
contempt for her subordinates in the company. When she
took the job, the first thing Ms. Wilson resented was the
“old boys” club that appeared to run rampant when she
arrived. Ms. Wilson fired four immediately and planned to
hire some women. She decided it would not be long before
she could clear out the entire nest of them and replace
them with some quality employees. Peggy Wilson went into
her private restroom adjacent to her office to check
herself before the morning meeting just as she did every
morning. She took great pleasure in humiliating the men
at this meeting.

At 43, Ms. Wilson kept herself in great shape, working
out in the gym. Externally her clothing was always very
conservative and business oriented. However, Ms. Wilson
always tried to wear undergarments that made her feel
sexy and feminine. Today, she wore a black thong and
black demi-cup bra that pushed her 40 C tits up and out.
She always checked herself in the mirror to make sure no
one could tell about her secret underclothing. Ms Wilson
could feel the men that worked for her staring at her
breasts, especially that worm Michael so she always made
sure her outward appearance was conservative.

After checking her appearance Ms. Wilson returned to her
desk to begin the days work. She always started with her
email and as she scan the sender Ms. Wilson saw an email
highlighted as a priority from Michael. Ms. Wilson was
amused, the subordinates, especially the men at Michael’s
level never communicating with her directly. Ms. Wilson
decided to read his email first. Surprised, it simply
said, “Open the attachment and acknowledge viewing
attachment. Once acknowledgement received, will send
additional message.”

Curious, Ms. Wilson clicked on the attachment and opened
it. Ms. Wilson slumped into her seat shocked at what she
had opened. There on her computer were pictures of Ms.
Wilson, five of them. One was a full frontal nudity shot
of her lying on a bed disheveled obviously fresh from a
sexual encounter. The second photo was similar but with
her on her stomach.

The remaining three photos troubled Ms. Wilson the most.
They depicted her in various sexual acts. One showed Ms.
Wilson with her lips wrapped around a faceless man’s cock
and his hands squeezing her breasts. The next picture was
of her being clearly fucked from behind. But the third
picture was the most disturbing to Ms. Wilson. In it, she
was triple impaled, a partner in her mouth, another in
her cunt, and the third in her ass. Ms. Wilson was
exceptionally upset because the pictures revealed her
thorough enjoyment of her predicament.

As Ms. Wilson sat staring at the pictures of herself in
disbelief. She tried to remember where, when, or how the
pictures came about. She looked closely at the pictures
trying to remember. Ms. Wilson recalled a party at the
end of her senior year, there were lots of jocks there
and she had gotten a little wild. A little smile ran
across her lips when she remembered the strip tease she
preformed, but that faded quickly as the reality of the
pictures confronted her.

“How could that asshole Michael have gotten pictures from
that,” she wondered.

As Ms. Wilson was still examining the pictures with the
familiar “beep” of incoming mail diverted her attention.
It was a second message from Michael and Ms. Wilson
quickly opened it. Ms. Wilson read the message over and
over again in disbelief. This second message contained
Michael’s demands that were basically blackmail. Ms.
Wilson knew that Michael was a sleaze when she read the
demands. Michael’s note contained the following demands:

“You will expose your pussy and tits to me in your office
tonight at 6 pm for at least fifteen minutes. As I am
only a voyeur, you will not be molested in any way, I
will just look then leave. If you do not meet my demands,
your pictures will be transmitted over the company’s
intranet system to all employees.”

Ms. Wilson was furious. She picked up the phone to call
security, but out of the corner of her eye caught a
glimpse of her pictures. Ms. Wilson slowly placed the
phone back in the receiver and tried to think of a way
out of this blackmail. She rationalized that no one would
care, but knew that her boss would fire her and her
career would be ruined without a reference. It made Ms.
Wilson angrier that Michael was the author of the
blackmail. After reviewing all her options and realizing
there were done, Ms. Wilson thought about what Michael
was asking.

“He just wants to look, that slimeball,” she thought, “I
can always have him fired afterwards by someone above

Ms. Wilson reluctantly composed a return message that
simply said, “Agreed.”

Michael excitedly read the response. It was now almost 10
in the morning and that was plenty of time to put his
plan into action. Michael quickly typed a new email
message and sent it out. Michael then left the office to
make the arrangements for his victim and returned just a
little before six. On his return, as he had planned, the
office building was almost empty. Ms. Wilson’s door was
closed as he stood in front of it waiting for 6 o’clock.
In his hand he carried the original photos.

At the stroke of 6 Michael, without knocking entered Ms.
Wilson’s office and partially shut the door. Ms. Wilson
looked up from her desk and heaved a deep sigh. She
admonished Michael about not knocking and Michael
intimated that she was not in a position to give orders.
Ms. Wilson asked if he had the photos and Michael showed
her the envelope. Ms. Wilson stood up, hand out, and
demanded the photos. Michael countered that when Ms.
Wilson met her side of the bargain then she would be
given the photos. Ms. Wilson huffed and walked to the
front of the desk.

“Where do you want to do this,” she demanded. Michael
cautioned her about the tone of her voice. Ms. Wilson
countered that she was only required to let him look, not
“be nice to him.” Michael conceded and directed her to
remain at the front of the desk. Ms. Wilson stood
defiantly with her hand on her hips waiting for Michael’s

“Tits first,” was all Michael said. Without emotion Ms.
Wilson opened her jacket and unbuttoned her blouse.

“There,” she retorted. Michael reminded her that the deal
was to see her tits and ordered her to remove the bra.
Ms. Wilson did not give him the satisfaction of seeing
her naked from the waist up and slip her arms out of the
coat one at a time to remove the bra. Michael whistled
when he sat her huge tits. That looked like two melons,
full with pink areolas and tiny nubs for nipples.

“Now what,” Ms. Wilson demanded. Michael pointed to her
skirt and Ms. Wilson pulled the skirt up high enough to
grab the waistband of her pantyhose and thong. She bent
over to yank them down to her knees. This was what
Michael was waiting for and he screamed “Now!”

Ms. Wilson jerked her head up just as the other four men
descended on her. Michael’s co-workers had crept back
into the building and were waiting just outside the door
for Michael’s signal. They bounced on Ms. Wilson who fell
over trying to escape with her pantyhose and thongs
around her knees. Quickly and before she thought to
scream, George wrapped adhesive tape around Ms. Wilson’s
mouth while Danny tied her hands together. Scott and John
controlled her kicking feet, rapidly wrapping their rope
around her ankles.

Once they got Ms. Wilson tied and gagged, the five stood
over her. They could see the anger in Ms. Wilson’s
reddened face as she lay on the floor, blouse opened,
tits free with her pantyhose and thongs around her knees.
She looked up at her attackers and fought the bonds to no
avail. Ms. Wilson tried to demand her release but it came
out as muffled garbage.

“We have to work fast,” Michael reminded the others. They
set about their tasks as Michael brought the side chair
to the center of the office. George and Danny knelt over
Ms. Wilson and could not resist chiding her about who was
the boss now. They grabbed her under her arms and stood
her up. Once standing, Scott and John each produced a box
cutter. Ms. Wilson was now afraid and shut her eyes
tightly as they approached her. Scott and John laughed
and sliced her clothes and removing them until she stood
before them completely naked. She felt a hand on her ass
and tried to move away.

“Nice ass,” Scott observed, “too bad it has to belong to
such a bitch.” As he finished his insult Scott ran his
hand down between Ms. Wilson’s asscheeks until his index
finger found her rectum. As Ms. Wilson shook her head
“No” Scott shoved his index finger into her asshole. Ms.
Wilson jumped and tried to move away without success as
Danny still held on to her other arm. They pulled her
over to the chair where Michael was waiting.

Michael walked directly in front of where Ms. Wilson
stood and without warning backhanded her on the right
side of her face. Ms. Wilson glared at him as her cheek
burned red. Michael reached up and yanked the tape from
her mouth.

“You bastards,” Ms. Wilson yelled, “I’ll have you all
fired and thrown in yell.”

“I don’t think so,” replied Michael, “you won’t be

Ms. Wilson interpreted that as a threat and began to yell
for help. Michael drove his fist into the middle of her
stomach and Ms. Wilson doubled over. Doug shoved the
tatters of her thong in Ms. Wilson’s mouth and replaced
the tape. As Ms. Wilson tried to catch her breath, her
hands were untied and she was bent over the back of the
chair. George and Danny each grabbed at wrist and held it
to the arms of the chair while Doug tied them.

While Doug tied her wrist, John released her legs, spread
them and tied each ankle to the leg of the chair. Ms.
Wilson was bent like an upside down “L” with her ass
jutting out and her pussy exposed. Because of the way she
rested on the arms of the chair, Ms. Wilson’s big, firm
tits hung down with her nipples scraping the cushion of
the chair.

Ms. Wilson finally regained her breath and tried to
protest her situation through the gagged. The five men
all stood behind Ms. Wilson admiring their prize. Ms.
Wilson heard their discussion about her “hairy pussy” and
“tight asshole” and could not believe she was in such a
vulnerable situation.

“Now that we got your attention,” Michael began, “we want
you to beg us to fuck you.”

Ms. Wilson just shouted into the gag.

“We won’t be able to understand you through the gag,”
Michael continued, “so when you’re ready to be fucked
just start shaking your head yes.”

The men laughed, as Ms. Wilson violently shook her head
“No.” She heard their belts being removed and began
shaking her ass trying to break free. Ms. Wilson thought
she would be raped until she heard the “swoosh” and felt
the belt across her ass and the loud snapping sound that
followed. Ms. Wilson jumped as the pain in shot through
her asscheeks.

Michael, who delivered the first blow, let the sting fade
before Doug swung his belt and it landed just at the
curve of Ms. Wilson’s ass. Ms. Wilson pulled against the
ropes binding her and yelled her protests into her gag.
The men stopped for a moment and Ms. Wilson heard them
talking about the red whelps that formed where the belts
struck her flesh.

“Are you ready to be fucked?” Michael queried Ms. Wilson.

Ms. Wilson shook her head to indicate her disagreement
with the question and Michael gave a nod that was the
signal to Danny, John, and George to get their licks in.
The three alternated in their blows across Ms. Wilson’s
ass. Ms. Wilson jumped against her ropes with each slap
from the belts. Bent over the chair in such a fashion,
Ms. Wilson knew the skin on her ass was stretched tight.
She frantically tried to block out the pain as she felt
the heat growing in her asscheeks with each blow. Michael
and Doug joined in and the intensity of the whipping
increased with the five men taking turns picking a spot
on their captive’s ass and striking it with the belt.

After about five minutes, the tears began to flow from
Ms. Wilson’s eyes and she fought her bonds more furiously
trying to find an escape. Finally, Michael struck a blow
that landed across Ms. Wilson’s protruding cunt lips. Ms.
Wilson threw her head back and jerked her arms up against
the ropes and her yell of pain was barely audible around
the thong secured in her mouth.

Each in turn brought their belts down hard on Ms.
Wilson’s cunt watching with glee as her labia turned
bright red and began to swell. Ms. Wilson thrashed
against the chair moving it about three inches with each
blow and throwing her head down into the seat. Her face
streak with tears, Ms. Wilson begged through the gag to
be fucked, but none of her abuser could understand her.

As John delivered the final blow to Ms. Wilson’s cunt
lips, Michael held up his hand for them to stop.

“I think she’s ready now, let’s ask her again,” Michael
said to the group. He came around to the front of Ms.
Wilson, grabbed her hair and pulled her head up so that
she would have to look at him. “Do you want us all to
fuck you,” he demanded.

Defeated, Ms. Wilson slowly nodded her head up and down.
Michael informed her that he was going to remove the gag,
but that if she screamed, it would be replaced and the
beatings would continue. Michael removed the tape quickly
leaving a red mark across Ms. Wilson’s cheeks where the
tape had been and then removed her thong. He was still
holding her head by the hair and she moved her mouth a

“Say it!” Michael demanded, “Say it or they will start

“All of you can fuck me,” Ms. Wilson mumbled.

“Beg us, and ask nicely,” Michael replied, “and this is
your last chance.”

“Please, don’t beat me anymore, please, all of you fuck
me,” Ms. Wilson implored.

Michael dropped her head to the seat cushion and he and
his co-workers removed their pants. Ms. Wilson’s body
jerked as she sobbed. Michael positioned his hard dick at
the entrance to her cunt, reached around and grabbed her
tits. Ms. Wilson’s tried to prepare herself without luck
as he drove deep inside her vagina without thought of her
discomfort or pain. Ms. Wilson grunted as she felt
Michael’s balls slapping against her clit as he pumped in
and out of her dry cunt.
“This bitch is rubbing me raw,” he complained, then
pulled his dick out, spit in his hand and rubbed his
member to make it wet, then slid it easily back into Ms.
Wilson’s cunt. “That’s better” as he reached around and
again grabbed Ms Wilson’s tits and began using them as
reins to rock in and out of her now wet cunt.

“Please, please, stopppp, stoppp,” Ms. Wilson grunted at
each thrust of Michael cock.

“Shut this bitch up, Doug,” Michael directed.

Doug grabbed Ms. Wilson’s hair and pulled her face out of
the cushion. Ms. Wilson yelped and shut her mouth tight
as she realized what Doug intended. Doug’s dick was
poised at her mouth, just touching her lips. Ms. Wilson
tried to move her head away, but Doug held tightly to her
hair. Michael pumped harder and watched as Doug tried to
force his rod into Ms. Wilson’s mouth without success.
Michael took each of her nipples between his forefinger
and thumb and slowly squeezed and squeezed.

“Owwwww,” Ms. Wilson screamed, and was cut off by Doug’s
dick and he shoved it past her lips and teeth and lodged
it deep into her throat.

Ms. Wilson pulled air through her nostrils and blew air
out the same way as she struggled to breathe. Doug warned
her that if her teeth left a single mark he would
personally beat her tits off. Ms. Wilson’s face was
turning red as her breathing increased. Doug moved his
cock a little backward allowing Ms. Wilson to catch her
breath. He then entwined his fingers in her hair on each
side of her head and started fucking her mouth. He and
Michael developed a rhythm, as Michael plunged into Ms.
Wilson’s pussy, Doug pulled out of her mouth a little.

“She a great cock-sucker, almost as good as she is a ass
kisser to the higher ups,” Doug mused, “Get in line!”

Ms. Wilson stopped struggling and simply tried to endure
being fucked and sodomized at the same time. Danny, John,
and George all waited their turns with Danny standing
behind Doug and the other two behind Michael. Michael
increased his pace and Ms. Wilson felt him tense then
felt the warmth of his seed spreading across her womb. As
Michael pulled his now limp dick from her cunt, Doug
ordered Ms. Wilson to get ready and she felt the first
spurts of his cum on the back of her throat.

Ms. Wilson had no choice but to swallow as Doug held her
head tight against him and his cock snaked down her
throat. She could feel Doug’s cock contract and then feel
his cum deposited down her throat. Before Doug finished
cumming, Ms. Wilson felt another dick shoved into her now
well-lubricated cunt.

“What a whore,” John commented as he fucked in and out of
Ms. Wilson’s cunt, “how long do we have her?”

“Till we’re finished,” Michael responded. Doug slowly
removed his dick from Ms. Wilson’s mouth as a string of
cum hung from her lower lip to the tip of his dick. When
Doug released her head, Ms. Wilson’s eyes were full of
tears and her makeup streaked.

“Open wide,” Danny said as he stroked his tool and
pointed it toward Ms. Wilson’s mouth. Resolved she had no
choice, Ms. Wilson opened her mouth and took his dick
without resistance.

“I want to get some of those big jugs,” and with that
John reached around and pulled on Ms. Wilson’s tits. Ms.
Wilson cried out at the pain, as her tits were sore from
Michael’s attention.

For over an hour the men took turns fucking Ms. Wilson
and forcing her to suck their dicks. Her pubic hair was
matted with their cum and her pussy juices. There were
beads of sweat on Ms. Wilson’s back and legs as George
finished with her cunt for the second time. When not
being forced to suck on of her attacker’s dicks, Ms.
Wilson’s head just hung down, supported by the cushion.
Occasionally Ms. Wilson grunted or cried a little and
this was boring Michael.

“I want her to resist, to scream, to make this worth the
time,” Michael said with anger. Michael pushed George out
of the way, took his hand and scooped up some of the
fluid coming from Ms. Wilson’s cunt. Ms. Wilson raised
her head slightly as she felt her ass cheeks pulled
apart. Her head was completely off the cushion when
Michael pressed his now hard again cock against her
puckered hole.

“Nooooo, not there, please not there,” Ms. Wilson begged.
But Michael just laughed and slowly pushed his cock
against her asshole.

Ms. Wilson was beside herself as the pain built in her
ass from the pressure. She continued to beg as Michael’s
dick finally pushed past her anal ring and worked it’s
way into her colon.

“Goddddd, you’re killing me,” Ms. Wilson wailed, “take it
out, take it out, fuck my cunt, my pussy, let me suck
you, pleassssssssssssse take it out.”

“What a dirty whore, begging to be fucked,” Michael
laughed and pushed the remaining inch of his cock into
Ms. Wilson’s asshole.

Once deep inside Ms. Wilson’s ass, Michael stopped and
waited while the woman continued to scream in pain.
Finally, her screams subsided to heaving sobs and Ms.
Wilson dropped her head to the cushion. Ms. Wilson tried
to concentrate on pushing the intrusion from her ass or
at least to relax the muscles in her ass. Michael waited
until he felt Ms. Wilson relaxed, the pull back until the
head of his dick was almost completely out, then plunged
back in until his balls slapped up against Ms. Wilson.

“I’ve waited a long time to make this bitch paid,”
Michael said matter-of-factly as he slowly fucked in and
out of Ms. Wilson’s ass, “you guys get the stuff, when I
get this bitch’s ass stretched out.”

Ms. Wilson grunted with each thrust and tried to remain
still to reduce the pain. She raised her head to try in
see what “stuff” the others were getting. She could hear
movement, but nothing else. The pain in her ass eased a
bit and she felt the cock growing.

Ms. Wilson knew that Michael would shoot his seed into
her soon. Michael increased the pace, using long strokes
to fuck her as he felt himself about to cum again.
Michael yelled and released his seed deep into Ms.
Wilson’s colon. Ms. Wilson began crying again as the
warmth of her attackers cum spread through her ass. Her
humiliation was complete when Michael removed his cock,
complained about the “stains” and wiped the shit from his
dick with her skirt.

The others now hurried to finish their work. Michael
ordered Ms. Wilson to be gagged again. Ms. Wilson tried
to avoid the gag, but she was no match for the men and
the thong was easily secured in her mouth. Ms. Wilson’s
eyes were wide with fear when she saw the propane torch
in Doug’s hand as he lit it. John held a block of wood
and wire in his hand. He heated the wire until it was red
then placed the block of wood under Ms. Wilson’s nipple
and with ease sent the hot wire through the center. Ms.
Wilson fought her bonds as the stars of pain shot through
her head.

John quickly placed a gold loop through the nipple,
flicked it with his finger and began reheating the wire
to pierce the other nipple. Ms. Wilson’s protest became
louder and louder through the gag as she watched in
horror as John effortlessly pierced the other nipple and
inserted an identical gold loop. It was now George’s turn
as Doug moved behind Ms. Wilson.

Ms. Wilson was unsure of what was happening until she
felt the block of wood at her cunt, then the pain in her
clit as George pierced it. Once the hole was done, a
third, but smaller, gold ring was placed in Ms. Wilson’s
clit. Ms. Wilson passed out as the wire burned the hole
in her clit.

Michael was not counting on this luck. With Ms. Wilson
passed out; it was easy for Danny to remove her from the
chair and chain her wrist together and shackle her
ankles. The men stood back and admire their handiwork.
Their bitch of a boss lay unconscious of the floor with
cum seeping from her cunt and ass. Her nipples and clit
had gold rings in them and she was helplessly shackled.
Michael threw water in Ms. Wilson’s face to wake her.

“Stand up,” Michael demanded and Ms. Wilson struggled to
her feet, naked. Danny and George placed a long trench
coat around her.

“What are you going to do with me,” Ms. Wilson asked.

Michael informed Ms. Wilson that they could not allow her
to go back to work so they had sold her. Ms. Wilson could
not believe her ears and tried to ask more questions, but
Michael refused to answer. Michael and Doug escorted Ms.
Wilson out the back door of the office building to
Michael’s car while the other three men cleaned her
office and returned it to normal.

Michael drove to the pier and he and Doug forced Ms.
Wilson out of the car. Ms. Wilson walked in small steps
due to the shackles on her ankles toward a man standing
at the end of the pier. Ms. Wilson could tell he was Arab
and he seemed to recognize Michael.

“What have you brought me today,” the Arab said as he
stripped the trench coat from Ms. Wilson’s shoulder and
let it fall to the ground, “a nice looking white whore.”

Ms. Wilson had no way to cover herself or defend herself
as the Arab ran his fingers over her breast, down her
abdomen, and then shoved two into her cum-soaked cunt. He
removed his fingers and wiped them on her leg, walked
behind her and separated her ass cheeks shoving two
fingers into her asshole. The Arab complained she was
still too tight.

“You were suppose to loosen up her holes,” the Arab said
to Michael.

Ms. Wilson pleaded to be released and began threatening
the Arab who simply laughed and snapped his fingers. Two
men came out of the shadows and placed a muzzle around
Ms. Wilson’s head effectively silencing her. Next, one of
the men produced a device like a chastity belt. On the
belt were to enormous rods shaped like penises but five
times larger. They stationed one at Ms. Wilson’s cunt,
the other at her ass and shoved them both inside her. Ms.
Wilson jerked and twisted against the belt and fell to
the ground. The pain in her cunt and ass was

“This will open her up enough by the time we get to my
country,” the Arab observed.

The two men each grabbed an arm and pulled her to a
small cage. Ms. Wilson fought and tried to prevent being
placed in the cage without success. Within seconds the
two men slammed the top down and Ms. Wilson found herself
muzzled, naked and lying in a cage that barely was large
enough to stretch out. Her ass and cunt contracted and
relaxed trying to adjust to being stretched further than
ever. In the distance she saw the Arab hand Michael a
large sum of cash. Michael and Doug departed, leaving Ms.
Wilson to the Arab.

About two months later Ms. Wilson was the main attraction
at a small Arab sheik’s sex show. Each night she is
brought onto the stage and forced to fuck a donkey in the
cunt and ass. As first Ms. Wilson refused and fought, but
after being hung by the rings in her tits on two
consecutive days she learned to cooperate. Ms. Wilson was
never allowed clothing and she had fucked the donkey so
much, her ass and cunt were always gaping open.
Eventually Ms. Wilson’s cunt and ass became so loose the
donkey would not cum so the Sheik sold her to a
whorehouse where her cunt and ass are sold for no more
that the equivalent of an American dollar. Ms. Wilson was
never heard of again.

Ms. Sams entered the office area and immediately started
in on Doug. Michael watched from his cubicle as Ms. Sams
threatened to fire Doug again.

“I don’t know why your predecessor put up with this
lacked attitude, but I will not,” Ms. Sams stated,
“that’s probably why she quit, but I won’t be so easy to
get rid of.”

That night Michael sat at his computer with the likeness
of Ms. Sams on his screen. It had been tough to find a
college photo of her, but well worth it as Michael began
the work of cutting and pasting her image onto the naked
body of another co-ed being fucked. He just needed to
create two more pictures, send the email, and contact his
Arab friend and Michael and his friends would be rid of
another new boss.