Cindy Gets Pimped Out By Her Boss

Written by mroberts / May 5, 2006


Cindy Gets Pimped Out By Her Boss by Anymouse (


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 accomplished."

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 appetite.

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 pussy?"

"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 thing.

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 virgin."

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 condom?"

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

"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 agree.

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 company."

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 all."

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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