Cindy Sleeps With The Boss
By: Date: 2021.12.31. Categories: Sex Stories Tags: , , , , , ,

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

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

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

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

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

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

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

“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

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

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

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

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

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

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

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?”


“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

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

“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.

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