Cindy Sleeps With The Boss

I had been having a fantasy to watch my wife Cindy (who was 28 at the time of this event) fuck another man. I had mentioned it in passing and even during sex, but her rigid upbringing would not even allow for such.

My wife’s boss a married well to do womanizer had the hots for her from day one. However, because of her rigid, conservative background, Cindy consistently rebuffed his advances. Steve wasn’t used to this kind of rejection, and he promptly listed Cindy as a major challenge in his life.

Steve was head of a major corporation, and because of his success, everyone, including Cindy, seemed to hold him in awe. At the same time, for Steve, “success, business, and women” were somehow all tired together. The fact that he and many of the women he bedded were married didn’t seem to enter into the equation.

Cindy had insisted that we not have sex before we were married. I understood her ultra-conservative family background, and so I accepted that. I just assumed that after we were married she would enjoy sex like most of the other women I had known.

I was very wrong.

Cindy was an attractive woman; 5 foot 5 inch, slim (only 11olbs), long brunette hair, with a nice firm C cup breasts that even her preference for conservative clothes couldn’t hide. Since her boss, Steve, had taken a strong interest in her from the moment he saw her, she was hired for a position and salary that was beyond her qualifications. Partly to prove herself to him, she had worked very hard at mastering her job’s demands.

After months of perusing her, Cindy’s boss started to wear her down to the point that she started telling me about her boss’ desire to “get into her pants.” Cindy looked at me each time she mentioned it, thinking that this would shock me. I intentionally didn’t react, but under my breath I mumbled, “He has a lot to learn about Cindy.”

Over the months, Cindy continued to hint about Steve’s subtle sexual innuendos. Frankly, I was getting a bit bored hearing about these sophomoric conversations. Finally, I blurted out something that I instantly regretted something that betrayed my complete frustration, “He might be disappointed.”

Anger flashed in her eyes, and I struggled to quickly amend my comment. “I mean.”

She, lighting up a cigarette, interrupted, “I know what you mean.” And then, for the 100th time she explained the hold of her ultra-conservative background, as if this would be all the explanation needed to explain our arid sex life. The fact that she was considered to be, in the words of some of the women she worked with, “the token prude of the company” didn’t help her attitude.

I found myself jealous of other husbands when they talked about the sex life they had. Maybe they were rubbing it in; it didn’t take too much time around Cindy before the word “prude” came to mind. In fact, I think it was the prospect of bedding “an attractive prude” that represented a major challenge for Steve; or maybe he recognized something else beneath surface. At any rate, Cindy’s boss wasn’t used to being so soundly rebuffed by any woman, and since “failure” wasn’t in his vocabulary, he doubled his efforts to add Cindy to his many bedpost notches.

Due to my own frustrations with Cindy, I was starting to enjoy this little drama. I even found myself secretly rooting for Steve maybe as a way of excusing the flood of wayward thoughts I had been having. I could imagine Steve screwing Cindy at times and I got me aroused, much to my surprise.

Finally, after 14 months on the job, Cindy came right out and asked me what I thought of Steve’s attention. I was a bit tired of her pussy-footing around the topic, so I thought I would introduce a real-world response. “He’s obviously wants to get you into bed.”

She turned away embarrassed without saying anything. I was surprised she didn’t stomp out of the room. Finally, she said, “I guess that would really upset things between us, wouldn’t it?”

Wow! For her to acknowledge such a possibility floored me. It was that point that I suddenly got the idea that this just might be what it would take to blast her free from her inhibitions. I replied, “Not if I knew that you really loved me and that it was just for an experience.” I then added, “I guess it wouldn’t hurt your job rating either.”

She looked at me incredulously. “You don’t really mean that!”

I obviously had to handle this carefully. “Well, I’m not even sure why we keep talking about this.” And then I threw in a bit of a challenge. “You don’t think I’m actually losing any sleep over this, do you?”

She didn’t like that response either. “What if I did do it?”

We were definitely back in the ball game. I shrugged, “Then I guess you and your boss would spend some exciting time together. Don’t you both want to?”

She eyed me suspiciously. “I know he does.”

“What about you?”

She didn’t answer, which in itself told me something. Maybe something inside her was changing. My job was now to keep the ball rolling. I took a bold step. “The first thing you have to do is admit it. Would you like to go to bed with him; “yes” or “no?”

She was frustrated at being forced to answer. “Well, I guess it would be interesting.”

“Yea, well, so far, all I’ve heard for months is talk. I guess that puts you in the category of women who are all talk and no action.”

She looked angry. “You don’t think I could.”

I didn’t answer; I didn’t need to. Again, things had moved too far and too fast for her, she immediately left the room.

Later that night in bed when I was reading, she said, “How would I go about it?” Her mood had changed, and although some time had passed, we both knew what she was referring to.

I had not expected her to bring it up again for a long time, if ever. “That’s simple, when he comes on to you again, don’t pull away.” She had often said she had to jump away from him when he tried to touch her.

“But what if he tries to kiss me, or put his hand on my breast, or something? I don’t know if I could let him do that. I’ve never let any man do that, I mean besides you.”

I squelched the temptation to say, And you’ve never been too comfortable even with my doing those things. Instead, I thought I would try to introduce a bit of humor. “And I guess you figure that you two could have sex without touching. I would like to be there for that.”

She looked at me. She had assumed that I would have put the breaks on the conversation long before now. “You can’t be okay with this.”

“Have you heard me say ‘no?'”

She studied me, “It’s only because you think I could never do it.”

My totally counterfeit smile communicated my response.

A couple days later she said that when her boss came onto her for the hundredth time in his office. She said she clenched her teeth and just let him. She let him kiss and fondle her. He was amazed at the change in her, and when he started to go further, Cindy, finally pulled sway and simply suggested, “Maybe you should just come over sometime,” and promptly exited his office.

I was amazed. Maybe this flight was about to leave the ground. “I hope you didn’t make any promises you can’t keep.”

“You still don’t think I can do this.” I didn’t answer. “If he comes over, you are not going to be here, are you?”

Maybe she was just testing me. “Sure, When you chicken out, I want to see it for myself.”

Cindy considered the situation. “Jez, he’s my boss. What have I gotten myself into?”

Well, I had actually thought through this remote possibility, and depending on how things developed, which was still very questionable, I had a rather good idea of what could take place and, more importantly, what I thought the consequences would be. Cindy knew that with me on the scene, she would never hear the end of it if she chickened out. She had sort of invited her boss over, and now was quickly becoming trapped in the situation.

Over the following weeks Cindy’s boss continued to mention her invitation, and Cindy continued to stew over how it could be handled. To sort of keep the ball rolling, I helped her pick out some lingerie at Victoria’s Secret and a new dress. It zipped up the front, and I suggested that she wear it. “You have to send a message,” I said.

“I think I already have. Now he’s insisting that I set a time when he can come over.”

It took a while, but finally she asked if she could invite him over the following Saturday. She fully expected me to say that things had gone far enough, but I’d obviously had plenty of time to deal with the possibility, so I said, “Sure, we’ve talked about it long enough.” With no way out now, she agreed to invite him over.

All day Saturday Cindy was visibly nervous. What about birth control? Like it never occurred to her. Since she smoked and we had sex so seldom and when we did I used a condom, I guess she had not thought it through that far.

I suggested that he use a condom, since he was such a woman killer, he would understand. That seemed to satisfy her.

She took a long bath and I helped her lay out her clothes for the evening, not slutty, but revealing enough to make sure he got the point.

When the time for his arrival drew near, she put on a conservative, dress. I called her a “chicken” and insisted that she change into the dress we had bought. Faced with the fact that I would never cease to taunt her about her decision, she finally did. She looked in the mirror and immediately turned away, embarrassed at how revealing it was. I could see she was having very strong second thoughts.

“But, really, what am I supposed to do?”

“For a woman, it’s simple, just don’t say ‘no.'”

“But what about you being here?”

“I’ll take care of that, don’t worry.” (I figured that if I left the scene, Cindy would somehow turn the whole thing into a business meeting, or Steve would do something that everybody would regret, and turn the whole thing into a disaster.)

Steve arrived with three bottles of expensive wine and a rather erotic DVD. He had clearly gotten the idea of the possibilities of the evening. My being home totally shocked him. I explained to him that I knew about the meeting tonight and I had hoped that he would not mind that I was home and in fact that with me being here, she would have to go through with it. Steve seemed shocked that I was cool with this and he apparently decided he would just have to cope with my being there – this time. He was clearly ready to get Cindy on any terms he could get.

Over a couple hours we all had several glasses of wine as we watched the video. After a while we were all a bit drunk and turned on. I sat in a different chair just to their side so as not to be a constant reminder of my presence.

Cindy watched the videos with her boss next to her touching her, in fact. Through her sheer dress, I could see her nipples peak as she watched the video, and she obviously felt the heat of his body against hers. I knew that she was in awe of Steve, but I had never seen that reaction in her before.

When the video was over, I suggested that Cindy give a tour the house. Eventually, we went into the bedroom and Steve sat down on our large king bed on the side of Cindy. There was a nervous silence for a while, and then he started rubbing her thigh, eventually letting his hands move up her side to her breasts. I watched from a chair in the corner of the room, not knowing where this was going.

Finally, Steve slowly pulled the zipper down on her dress, exposing her bra. Cindy just shut her eyes and took a deep breath, as if to object, but didn’t. Steve then unhooked her bra and let it fall into her lap.

This was an opportunity that would probably never present itself again, so Steve slowly pushed her down on the bed and rubbed her breasts as I watched. With that, all his reservations dissolved. He started to kiss her breasts. Although very nervous, I could tell by her breathing that Cindy was reacting.

Clearly, Steve didn’t want me to be there, but he was not about to jeopardize this opportunity by asking me to leave. Finally, he helped her out of her dress.

She looked at me to see my reaction – or maybe it was a cry for help. I tried my best just to look casually interested. Finally, she made a decision, put her arms over her head, and just looked up at her boss. Given the situation, he was still hesitating to go further. But, she had apparently made a decision, so in a few moments just opened her legs and looked up at him.

It was at that moment that we all realized that things had reached a point of no return. Steve reached down and removed her panties. There was my wife lying naked and exposed. Cindy, whose voice was choked by caution, mentioned that there were condoms on the night stand. As Steve picked one up, I quietly commented that he did not have to use one if he did not want to.

“I don’t want to, are you on the pill?” Steve looked at Cindy and asked.

Before she could respond, I answered, “Yes she is.”

Cindy gave me a shocked look and I could see the tears begin to well up in her eyes.

Steve quickly pulled off his clothes, climbed on her, and after a few strokes he was fully into her. It seemed that he didn’t want to risk her changing her mind by elaborate foreplay. This woman had finally surrendered to him, he had accomplished his goal.

For me, that was a moment of very mixed feelings, seeing my wife under another man. At the same time, she just sort of laid there not doing anything. Finally, Steve said, “How about a little enthusiasm here.”

Cindy looked at me and I nodded, and soon had her hands on his butt, regularly pulling his thrusts deeply into her. Obviously, although a bit drunk, she was trying to be “good in bed” for her boss. She knew he had known a lot of women, and I’m sure she felt she had to “measure up to the competition.”

The fact that he was a good, I might even say an “excellent” lover, could not be denied. I tried to dismiss all comparisons from my mind. Slowly she started responding in ways that I hadn’t thought I would ever see. Maybe the booze had something to do with it; maybe not. Steve raised his head and studied her as he continued his thrusts. Finally, after all these months of trying to get her into bed, her nude body was under him. I could see the look of victory in his eyes. Cindy’s look and actions were strange, like someone who had been completely taken over. At that moment, I got the feeling that he completely owned her. I wondered if she too had been wanting this moment for a long time and the months that he had been pursuing her amounted to a kind of very prolonged foreplay.

As he started to come, he started to get very rough with her, to a point that I was worried that he was really hurting her. As he did, she clung to him and I saw her body flush in a way that I had never seen before. He began to grunt as he filled Cindy with his seed. I began to have second thoughts about not using birth control, but now it was way too late.

Finally, Steve laid down on her and just held her. He said things in her ear that I couldn’t hear. Slowly she started to respond. His mouth found hers and I could see Cindy’s mouth open for him. They continued to kiss deeply and within a few minutes he began to move in her again. He whispered something in her ear and I heard her say “yes.” Their motion again flowed together as their pace slowly increased. He kept whispering things in her ear and she was responding with sounds of pleasure.

It took a while, but he became hard again. I guess he wanted to get it a second time, not knowing if there would be a second time. Soon he began to stroke her again, his cock responding to her pussy. Cindy cried out several times, whether because of pain or pleasure I didn’t know. Possibly it didn’t matter. Finally, she looked over at me, embarrassed, and quickly looked away. Steve lasted a little longer the second time and again came in my wife. Spilling his sperm in her for a second time. Steve just collapsed on her and got his breath. Cindy glanced over at me and smiled.

Steve got up. As he started to dress, Cindy just looked at him for a few moments, as if she was trying to figure out what happened. Then she seemed to quickly come back to reality, and jumped up and headed for the shower, largely I think to escape her own embarrassment.

I walked Steve to the door. He looked at me and then glanced away, searching for words. “This is a bit award, but I enjoyed… err… I appreciate.”

I interrupted, knowing that it would be a hard sentence to finish. “I guess think that since you’re her boss, you can now have her any time you want.”

He looked surprised at the statement. “You think I would do that?”

“If she wants to keep her job, she can’t exactly say ‘no,’ can she?”

He started to protest, but the way I said it communicated something else. He immediately assumed that I wanted her out of the way as much as possible for my own exploits. His interpretation was fine with me.

I looked squarely at him. “As long as you treat her right and see that she isn’t hurt in anyway… well she needs to experience doing new things. I guess you can handle that.”

He glanced toward the shower, where the water was still running. “She can be pretty… resistive.”

I knew Cindy, she would have would have major guilt and second thoughts about this. A second and third time would be crucial to getting through that. “You don’t think you can get her in the sack again?”

He smiled, still without looking at me. “I’m supposed to be pretty good at that kind of thing.”

I looked directly at him. “Let’s see if you really are.”

He studied my face for a long time, searching for my motivations. Finally he just turned and left.

When I returned to the bedroom Cindy came out of the shower with a towel wrapped around her.” No longer embarrassed, she seemed almost jubilant. You didn’t think I could do it, did you?” as she lit a cigarette.

“No, I didn’t.” I watched her as she dried her hair. “I guess you enjoyed it.”

She hesitated, embarrassed. “Kind of.”

I smiled. “What I saw was much more than ‘kind of.'”

She giggled like a school girl. “I guess.”

“What if he asks you again?”

She dismissed the thought. “I just had to prove something; you know that.”

“And you think you can say ‘no’ to him now and keep your job?”

That stopped her abruptly. “What are you saying; I can’t say ‘no’ now?”

“Think about it.” I was surprised she hadn’t; but, then again, she was new at this kind of thing.

“Okay, so what if he does ask me to go to bed again?”

“Say you will.'”

She studied me. “Serious? You want me to go to bed with him again?”

“Yes.”

“What if he doesn’t ask again? He got what he wanted.”

“He’ll ask.”

Not surprisingly, her boss wanted more. Two days later she said talked a long time in his office and ended up having sex. I could already see that she was changing in some major ways. She looked at me. “Is that okay with you?”

“Did you enjoy it?”

“You knew this would happen, didn’t you?”

I didn’t say anything.

She thought about it. “If he won’t take ‘no’ for an answer after this, I would have to quit my job. I mean I can’t exactly claim sexual harassment at this point.”

She could, of course, but I wasn’t about to muddy the waters with that. For the first time in her life, Cindy had apparently really gotten into sex, and I couldn’t get that out of my mind. I shifted the conversation to another thought. “And if you would quit, where would you get another job that pays like the one you have? Isn’t this is the house you wanted, despite the payments; not to mention all the things you’ve been buying.”

She was abruptly stopped with that thought. “So what am I now, a prostitute; doing it for money?”

“No, I hope you are enjoying it; that you both enjoy it.”

“I guess that I need to get a diaphragm if I am going to start screwing around with the boss,” she added.

I thought that if she had sex with him for a few weeks or months that she would have a changed view about sex. That’s something I had been desperately wanting since I had found out on our honeymoon how desperately up tight she was about sex.

I will relay future stories on how Cindy has changed.