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Cindy Gets Pimped Out By Her Boss

May 5, 2006

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Cindy Gets Pimped Out By Her Boss
by Anymouse (mroberts142@yahoo.com)


My wife's boss has turned her into the company whore.
(MMF, wife, voy, creampie, cuck)


This is part two to how I got my wife Cindy to start to
fuck her boss. To recap: Cindy was an attractive woman;
5 foot 5 inch, slim (only 110lbs), long brunette hair,
with a nice firm C cup breasts that even her preference
for conservative clothes couldn't hide.

Over the next few weeks Steve regularly took her to an
apartment owned by the company. Cindy agreed to go to
her doctor and get fitted for a diaphragm. The change
in our own sex lives was immediate, and I was thankful
for that, even if another man was responsible.

I had assumed that after succeeding in his quest to
finally get Cindy in bed that Steve would soon move on
to some other woman, just as he had done with other
women. But he apparently recognized something in her
that he didn't want to abandon just yet.

The company apartment was often occupied, so before
long Steve was calling Cindy and arranging to meet in a
motel. Apparently this was so much in contrast to
anything she had previously done, that Cindy was
excited at the prospect of going to different motels to
meet a man. She would ask me first, and if she stayed
out longer than usual, she would call.

Cindy would return flushed, and disheveled. My only
request was being allowed to go down on her spunk
filled pussy. She would light up a cigarette and would
tell me everything they did. Rather than being shy
about the details, she had now grown to a point of
clearly being proud of the things she could say and do.
I would love to look up at Cindy as I went down on her,
cleaning out all of Steve's sperm.

Cindy bought new, more revealing clothes. Her attitude
changed. She seemed more free and open about things.
Instead of being embarrassed when men looked at her,
which they now did more than ever, she seemed secretly
pleased. Although I had paid a major price for this
change, I definitely didn't want the old Cindy back.
For me at this point it was like, "mission

But some things you set into motion take on a life of
their own.

Suddenly, Cindy was wanting to try everything. No
longer was I thinking about outside sex; in fact, I
found myself struggling to keep up with her new sexual

Cindy often mentioned things that she had heard about
that she wanted to try. Steve must have also felt her
need to make up for lost time, and since he felt he now
had some control over Cindy, he decided that this was
his chance to try some new things with a woman.

First, they tried bondage. She told me about it in
detail. He would blind-fold her and tie her spread-
eagled on a motel bed. Because of the blind-fold, she
could concentrate entirely on the sensation of what was
happening. He got to be an expert on when she was about
to come.

To tease her, he would abruptly withdraw just she
started to come. Sometimes he would use a vibrator.
Tied, spread-eagled, she could do nothing; just hang on
the edge of coming. So, in exasperation she would
finally start to plead for him let her come. He would
do this over and over again.

Bondage was a power thing with Steve, of course. He
would look at her helplessly tied beneath him and say,
"I want to hear you beg for it." It took a long time,
but she finally did. I found it hard to believe that my
wife would beg a man for sex, but that's what he had
her doing.

It not only turned Steve on, but, because of the way
Cindy had been all her life, being able to do this was
liberating for her. She now seemed to relish pushing
the boundaries of her new-found sexual freedom.

During one of the bound and blindfolded sessions, Cindy
said it seemed as if there was another man in the room,
but Steve had said it was just her imagination.

By this time I was having some definite reservations
about what was going on, and Cindy apparently hinted as
much to Steve.

One afternoon Steve asked Cindy if he could borrow her
car. He said he would drop her off at home and have her
car back by the next morning. The next morning I
discovered an envelope with car keys had been pushed
through the Mail slot in our front door. They weren't
the keys to her car, but the logo on the keys was
unmistakable. I checked the driveway. Cindy's car was
not in the driveway, a new Mercedes was. On the front
seat was the title to the car in both of our names. All
we had to do was sign.

Steve then started using a video camera and videotaping
some of the motel sessions. He made her undress in
front of the camera, and then he kept the tape rolling
as he blindfolded her and tied her to the bed. Soon she
forgot about the camera rolling and then he went into
the same routine of getting her to beg for sex, and
finally to climax.

One time he filmed her starting to undress and she
asked him if she could go and put in her diaphragm. He
asked her not to.

"Will you get pregnant this time?" Steve asked.

"No I finished my period last week, I should be safe
this time, do you like cumming in my unprotected

"You know I do." he replied.

I then got to see Cindy get undressed and saw him enter
her and fuck her without any protection.

Despite her objections, he made copies of the tape and
told her to give one to me. Cindy said I could only
watch it when she wasn't there. I did, and the woman in
the tape was nothing like the Cindy I knew. It was
clear to see that he had her totally under his control,
and she was responding without hesitation to what he
wanted from her. He was obviously proud of how he had
changed her.

Steve took a copy of the tape to his office and teased
her by saying that if she "wasn't good," he would show
it people around the office. He placed "one copy" of
the videotape on his desk in plain sight, a reminder to
her. It was even clearly labeled "Cindy." Steve saw it
as a "victory trophy." It was cruel, and for weeks she
worried about it. But this too had a purpose. That
Christmas we both got a year's membership for both of
us in a swanky gym.

Whether anyone else saw the tape is not clear, but
Cindy said comments around her office about her being a
prude abruptly stopped. In one instance Steve overhead
a conversation between a couple of women in the office
about her, and he dressed them down right in front of
everybody, ending with something everyone heard, "If
you want to continue working here, you'll damn well
watch your mouths." If there had been any doubt, it was
clear now to everyone that Cindy was no longer just
"one of the girls."

At this point I felt I had lost control of this whole

I will re-tell a story of one weekend, Cindy and Steve
met another executive, Bill,who was black, in the hotel where they
had checked in. The three of them had drinks and talked
for a couple hours in the hotel bar. The man knew that
Cindy was there for Steve. He was also attracted to
her. The two men talked when she was in the power room.

The tree of them went to the man's motel room and Steve
announced he was going out for a while. Cindy jumped up
and said, "I'll come along?"

"No, stay here."

She was startled. "But."

He interrupted, looking squarely at her. "Don't
disappoint him, or me."

"But, I did not bring my diaphragm with me this
time!!!" Cindy whispered, besides he is black?"

"Maybe he brought a condom with him, either way you
know what you are here for." Steve added angrily.

"You aren't racist are you?" He added.
He then abruptly left the two of them together.

Steve went to the bar and was clearly drunk when he
came back an hour or so later. Bill were lying on the
bed when he came in. Cindy, sitting in a chair smoking
a cigarette, still had her dress on. The man was
clearly frustrated. "Jez; you'd think she was a

Steve seemed disturbed. He came over and had her stand
up. Steve then unzipped her dress and let it fall onto
the floor. He then undid Cindy's bra, pushed her back
on the bed, and dragged her panties off. Cindy tried to
cover her breasts and pubic area with her hands.

He nodded to his friend. "Now take her."

His friend looked at the nude woman on the bed. "It's
okay with her?"

Her boss glared at her. "It is okay, isn't it Cindy?"

Cindy looked over at Bill and asked, "Do you have a

"No, I thought all that stuff was taken care of," he

"Sure it is taken care of, she is just a little nervous
that is all" Steve interjected, "It's ok for him to
fuck you with out a rubber on, Right!"

Meekly, she nodded.

Bill got undressed and Cindy moved up further on the
bed. Bill spread her legs and moved between them. Cindy
could feel his cock trying to find her opening, and
when he finally did, he shoved it all the way into her.
She felt a tear starting to run down her cheek as he
fuck her. She looked over at Steve, who had a huge grin
on his face.

She laid there, realizing that she was indeed a whore, a company whore.
Cindy just laid there, letting this strange man fuck her, a strange
black man at that. She had never seen a naked black man, let alone
fuck one.

Why did Steve want her to do this? She doubted that she
could get pregnant, but there was always that change. When
she was fucking Steve, atleast she chose the week right after
her last period so the chances were lover. She felt so ashamed.

In a few minutes, while Steve watched, Cindy felt the
man come in her. She faked a really big orgasm, partly
to try to make Steve jealous.

The following week Steve was contrite, even apologetic.
He blamed it all on the fact that he had been drunk.
There were gifts of jewelry, he saw that she got a
raise, and even gave her a company credit card to put
gas in the Mercedes.

A few weeks later Steve broached another way to push
the envelope of Cindy's liberation. By now she had
adjusted to being pushed into sex with a strange man in
the motel that she had just met. She had also accepted
the fact that people around the office knew that she
was Steve's mistress, and even the possibility that
some men had even seen the tape made in the motel.

Strangely, she wasn't totally humiliated by any of
this. I think Steve had convinced her that all this
represented a kind of breakthrough in her life; which,
in a perverted way, it was.

Steve had been turned on watching Cindy with his friend
in the hotel room. Now, he wanted to demonstrate his
power over her and watch her give herself to different
men. The plan was to go to a swanky singles bar and let
her pick out men that interested her.

After going around the room numerous times and
carefully looking them over, she would then tell Steve
whom she had selected. If he approved, he would go over
to the man and strike up a conversation. If Steve still
approved, he would say that Cindy was a prostitute, he
had paid for her for the night, and that he wanted to
watch her with another man. The man would take a look
at her (in very sexy clothes and beautiful) and often

Steve would get a hotel room and then accompany Cindy
and the man back to the room. Steve would sit in a
chair watch the two of them. They knew what was
supposed to happen, but took different routes getting
there. Steve liked to see them struggling to get to the
main event. Each time it was a different show; each
time it confirmed his power over her.

Most of the time, they wore a condom since she was after all
a hooker. Some would not bother, but she was prepaired for that
and would have her diaphram in before hand.

When Cindy came home after the first time they did
this, she tried to hide her excitement, but she talked
about it for over an hour. "God, I just picked him out,
this really handsome guy, and never even talked to him
or anything, and suddenly we are in bed together! I
didn't know I could ever do something like that."

"Did you have in your diaphram in?" I asked.

"Yes, but they wore a condom." Cindy replied.

"I would really love for you not to have them wear
a condom, if you don't mind." I asked.

"I will have to ask Steve."

I asked Steve and most of the time, Steve made sure that she did not make
them wear a condom.

I liked that also, since I got to end up tasting all of these different men.

One day, when Cindy was talking to me about her
experiences, she said, "You know in the beginning I
felt I really got trapped into this. But, I've sort of
adjusted to 'getting it on' with guys."

She was quiet for a while.

"Going up to the room in the elevator, when the guy
looks over at me, it's sort of a scary and exciting,
knowing what's about to happen. Steve's made clear that
for me backing out is not an option; and although I've
picked the guy out, I never really know how it's going
to be with him. I like to put on a show for Steve as we
do it."

She thought about it. "Did you ever think I could let a
man undress me right after I met him? I mean I just let
this strange guy who knows he can have me take off my
clothes. And when I'm necked in front of Steve and him,
I give the guy oral sex; all the stuff that Steve has
told me do to. Steve loves to watch me with a guy."

There was silence for a while. Finally she broke the
said. "Steve doesn't want me to pick out the guys any
more; he wants to pick them."

I saw it coming; Steve needed to have full power over
her. "Who will these guys be?"

"I saw Steve talking to one of our clients today in the
office. They kept looking over at me. Later, Steve said
I'm supposed to 'entertain' the guy tomorrow afternoon.
I guess I'm his 'bonus' for something with the

Liberation or no liberation, this was a step too far.
"God, now you really are a prostitute bought and paid
for!" I decided to appeal to whatever shred of modesty
she might have left. "Won't everyone around the office
guess what's going on?"

She shrugged. "They used to pay girls a couple thousand
dollars a night to do this. Steve got the best. So I
guess in terms of desirability I'm in pretty good
company. Everybody knows about me now anyway. Steve
made sure of that. What's done is done; and, come to
think of it, I never heard you complain before,
especially about the new car, the club membership, and

I struggled for a way out of this.

She continued matter-of-factly. "The guy's coming by
the office tomorrow afternoon to pick me up."

"Why the office, for God's sake?"

"Steve wants people to see me leaving with him, so
they'll know..."

"That you're a prostitute!"

"Well, at least I don't hear you complaining any more
about how sexually hung up I am!"

"Okay, you've gotten past that, for sure, and maybe I
should have seen this whole thing coming and called a
halt to it before it got this far. But, at any time you
could have jumped in and said 'no.'"

"Not any more. I can't."

"Can't or won't? Jesus, woman! You always said 'no' to
doing anything different with me."

She studied me. "You haven't figured it out?"

I didn't know what she was getting at. "I guess not."

"I wouldn't do these things, even if I secretly wanted
to, unless I was forced."

That took me back. "You wanted me to force you to try
new things?"

I was upset, and it very much showed. "And that
includes leaving your office tomorrow with a man that
everyone knows you're going to offer your very married
body to as his bonus?

"Well, you sort of encouraged it, at least at first.
But now it's sort of my job. That's what Steve wants me
to do. Everybody knows what I'm doing, so what's it
matter now?"

I was mystified. "Cindy, before this goes any further,
it's about time you start doing what you want?"

She looked squarely at me. "That's the point; I need
Steve to make me do it."

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