Wife and her boss

[rob84]

For several months now, my wife has been working as an assistant for an executive at her company who is somewhat notorious for being a playboy, particularly for having an affair with his last, married assistant.

Now, we aren't in a cuckold relationship, but I found the idea to be extremely hot and after she took this job (she had previously worked in another position for the company) I began to work the idea of her and her boss into dirty talk and even role playing during our love making. She seems to really like this and get off on it as well. Recently during one such session, in the heat of passion she dropped the bomb on me that he actually has run his hand up her thigh and grabbed her ass. I think she was then immediately worried that I would be mad and seemed to want to brush it off as "not a big deal" when I asked her if she liked it. I didn't want to push her so I just let it go and we continued playing.

How would you respond to this? Do you think there is potential here for this to go further? Do you think that's a good idea?

 

[Trying]

1) I know what I would do,but the question here is what you want to do and either keep it a fantasy or bring it into reality...

2) yes

3) maybe,maybe not...

 

[markieboy]

I would tell her how hot that was, how you knew something like that could happen with such a virile, attractive man. Then you might focus the conversation on whether she thought he would be careful enough to trust with an affair. And ask if she found him sexy - you know the answer to that one. And then subtly imply that, well, if she thinks he has more to offer and could improve her life, it is, well, after all, her choice and she should know that you love her totally and want her to be fulfilled.

And you might then, over the next week, get her some nice thongs, stay up stockings and push-up balconette bras for wearing to work. She may at first look at you like you are crazy, but when she wears them the next day, you will know where she is headed.

If she wishes, a quiet lunch with her boss, in which she admits that she is a bit unfulfilled at home or just keeps thinking that there must be more and has always wondered if she should consider looking elsewhere will seal the deal.

Why did the previous affair with a secretary end? Did she go on maternity leave?

I have never had to encourage my wife like this - she has always taken it for granted. She has had many affairs with key clients and associates at other firms. Her discretion has fit the situation.

Good luck. Her boss is her superior - if you want to be a cuck, it is a natural and very fitting situation.

 

[dana007]

Rob84

i do somewhat agree with markieboy but if you want this her boss might be a good first one to try.

i am not going to say it is easy and if you do this you have to rember that there maybe no going back if it goes wrong.

so agood thing to do is you and her talk it out and make sure it is what you both want to do and make sure to start out slow.

well how every it goes keep us posted.

 

[Custer Laststand]

For several months now, my wife has been working as an assistant for an executive at her company who is somewhat notorious for being a playboy, particularly for having an affair with his last, married assistant.

Sounds promising...

Now, we aren't in a cuckold relationship...

Evidently you're within range of rectifying this situation...

...but, I found the idea to be extremely hot.

...especially given that you're responding appropriately, perhaps in spite of yourself.

After she took this job (she had previously worked in another position at the same company) I began to work the idea of her and her boss into dirty talk and even role playing during our love making.

Cool...

My wife seems to really like this and get off on it as well. Recently during one such session, in the heat of passion she dropped the bomb on me that he actually has run his hand up her thigh and grabbed her ass.

Ah... so your wife is giving her boss the message that she finds him sexually attractive, and he's beginning to respond...

I think she was then immediately worried that I would be mad and seemed to want to brush it off as "not a big deal" when I asked her if she liked it. I didn't want to push her, so I just let it go and we continued playing.

And, at your end, your wife has begun testing the waters with you. Almost certainly, she interpreted your response as favorable...

How would you respond to this?

Probably in a way somewhat similar to your response (as described above).

Do you think there is potential here for this to go further?

Yes, clearly.

Do you think that's a good idea?

Depends on how your wife, you and her boss handle it. I suggest some honest, fairly specific discussions with her in the cold light of day — not just while both of you are turned on in bed. Try to estimate the probable range of outcomes, undesirable as well as desirable.

In particular, your wife needs knowledge of what happened to her predecessor; i.e., her boss's previous assistant with whom he had an on-the-job-affair. Did she lose her job for seemingly-vague reasons that may have been attributable to their affair?

Also, your wife and you should take into account whether her company has a policy prohibiting affairs between bosses and those under their direct supervision. Some companies do, in whole or in part because they fear sexual-harassment lawsuits (in the U.S. — I'm not sure to what extent that tends to be the case, if at all, in other countries). If so, your wife may be setting up a situation where either she or her boss could be fired or transferred... if it's her, to a less desirable position and/or location.

So, if that's a possibility you and your wife should consider whether you can afford that outcome.

 

[irreverent]

You seem to be well on the way to new adventures, and have made significant progress since your previous thread. This must be an exciting time for you. How did you introduce the subject of her boss in your lovemaking the first time, and what was her reaction then? Has she brought up that subject herself, in bed or elsewhere?

 

[robandkate]

I have been married twice and both of my wives, with my encouragement, fucked other men. My wife Kate has been spreading her legs for other guys for over 20 years now.

My ex wife fucked both her boss and my boss. She fucked my boss first. When she was going to college, I was a bartender. My boss was a mid-40s married guy with kids. He owned the bar where I worked.

My wife and I were just 21, but she had been fucking a few of my friends for a couple of years by then. I told her that my boss thought she was hot. I told er I thought it would be hot if she let my boss fuck her. I shared with her that he had a couch in his office.

Late one Saturday night my wife came to the bar. She was dressed very sexy in a really short skirt. She kissed me and said she was going to my boss' office to talk to him. My boss and my wife came out of his office an hour and a half later so my boss could help me close the bar. My wife just winked at me and smiled.

When I got home, she told me that she and my boss had sex on the couch in his office. Of course, he made her promise to never tell me. A couple of weeks later, my wife came in late on Saturday night and fucked my boss again in his office while I was out front working.

That went on for a few months, then my boss started going to our apartment and fucking my wife while I was at work. They fucked fairly often for a couple of years. My boss never let on that anything unusual was happening.

We had so much fun with my wife fucking my boss, that when she got her first job out of college, we decided it might be fun for her to fuck her boss. He too was a mid-40s married guy and an executive for a Fortune 500 company. After flirting with him for a couple of months, my wife invited her new boss out for a drink. They ended up in our bed.

Both of our bosses were fucking my hot young wife. It was great. Never any repercussions for either of us as a result of playing where we worked.

Rob
robandkate@hotmail.com

 

[monitaur]

Great start! Encourage her for sure.

 

[Saraha]

Sounds very sexy and no victims, all winners including you.

 

[Nihilist]

Very hot! Thanks for sharing!

 

[rob84]

Thanks for the replies, everyone. First to answer some questions: the affair with the previous assistant ended because she and her husband moved to another state for his job (as far as I know he was never aware of the affair). And, my wife is aware of his reputation and history and was aware of it before taking the position - I only know about it from her and her friends talking about it.

Anyways, we talked about what she said the other day. I told her that I wasn't upset and thought it was kind of hot that other guys find her attractive and thought the idea of her flirting with other guys was sexy. Eventually, with my encouragement, she sort of loosened up on it and admitted what happened. Apparently the hand on the thigh thing is actually a fairly regular occurrence! I asked her if she finds him attractive and she yes (she admitted that he is "hot"), but quickly added that she has "no feelings for him."

 

[gatorrdw]

there is some good advise

There has been some good advise given so far. My first wife had sex with at least 4 different managers or bosses while she was working and also had a long term affair with the owner of the company I worked for. This all started back in the 70's and 80's before there were any issues about "sexual Harrassment", with two of her bosses she was their personal assistant and she enjoyed the sex as just part of the job. We knew what we were into and there wasn't any problem with any of her employers, they all knew her as my sister and would often discuss with me at parties how hot my "sister" is. You have to be sure between the two of you that you are both comfortable with where this is headed - if you both are it can be a terrific high. GTR

 

[irreverent]

Hi Rob84, hope you have found your way here.

If you are reading this, is there any news about your wife and her boss? In your last message your situation seemed to be in a good dynamic, and you were in for some exciting times. Any private meet-ups between your wife and her boss? Any make-out sessions between them?

 

[rob84]

Yes, there are some updates. We have continued the dirty-talk about it and I kept up the encouragement and she seems to enjoy it and be more comfortable in even admitting that she enjoys his attention and the fact that she knows he's attracted to her. I've even been encouraging her to flirt back, which she seems to think is a fun idea (at least, I thought, in the heat of our dirty-talk and fooling around). After I had begun this encouragement, she told me a few days later that he had his hand on her thigh under the table at a meeting and she let him keep it there. She asked if I was mad and "I said no, that's hot," she then admitted that he had worked his way up and grabbed her crotch over he clothes. We had been sitting on our bed and I had been kissing her neck, encouraging her and she seemed to be getting into it and getting hot. She didn't admit to anything else, but it seems strange to me that this is all he would have tried to do if he is willing to go that far and if she was letting him do it. I wonder if there is more that she isn't telling me - maybe she knows I'm okay with that particular act but is worried to tell me the rest.

Recently, before she left for work I saw that she got dressed in a new skirt I'd never seen her in before and told her it looked good. She replied saying, playfully "Yeah, do you think [my boss] will like it?" I told her "I don't see how any man wouldn't." When she got home I asked how he liked it and she said "He didn't say, but he sure wanted to have his hand up there."

 

[dana007]

rob84

great post can't wait to hear where it goes from her.

keep up the support for your wife in all this.

keep us all posted on there fun.

 

[midnightfapper]

it seems strange to me that this is all he would have tried to do if he is willing to go that far and if she was letting him do it. I wonder if there is more that she isn't telling me

Maybe he is just taking it slow, to avoid scaring her off. To me that seems more likely (and less risky) than jumping in head first.

Edit: Just noticed an unintentional pun. Cock head first into her vagina! Lame pun, I know, but I couldn't help myself. =p

 

[irreverent]

She may be reluctant to admit to situations where she took the initiative. Since they work together, I guess there will be one-on-one-situations where they could have kissed, or even gone further. Maybe she just needs some extra assurance on that before she opens up completely.

From her boss' perspective, if a woman I liked let me get my hand up her skirt and gave signals that she liked it, I know I would have wanted to take it further at the first opportunity.

Do you want to go all the way here? Do you want your wife and her boss to become lovers? If you do, and you feel you are both ready for it, you could try to create a situation where something might happen, like inviting him over for dinner or something. That may be a bit contrived, but I'm sure others here will have much better suggestions.

Best of luck!

 

[monitaur]

Get those two fucking bareback Rob! As soon as possible. Use the pill if you don't want a baby from the deal.

 

[becontree2001uk]

Good luck Rob -we are all rooting for ya

 

[jjboi]

back in the early 70's i got married for the first time. she was 18, i was 22. after i got fired from the job i had at the time we moved in with her grandparents. being young, inexperienced and above all horny we wanted to move out on our own as soon as possible so she also got a job. she got a job as a receptionist for an accounting firm. all of the accountants were 50 and over and of course quite well off. we only had one car so i would drop her off at work then when i got off go and pick her up. one day after she had been working there for 8 or 9 months i got off work early and went by to let her know i was going to leave her the car and go to a bar a couple blocks away. when i got there she wasn't at the front desk so i just walked down the hall to see if i could find her. i should tell you that she had already cucked me with a cousin of hers so what i saw wasn't that big of a shock. when i turned a corner in the hall there were 3 of the partners standing in the doorway to one of the offices, which i later found out was the big bosses office. i heard them making comments about how good she looks with her top off, and what a good job she was doing on the old man. i also didn't know at this time that she was the only female working for these men so i wasn't immediately tipped off that they were talking about my 19yo wife. so i walked over to the doorway and looked over a shoulder and there was my wife sucking an old guys cock. my cock immediately got hard but i didn't want to get caught or disturb the fun so i just turned and walked back out. when she came out at her regular time i told her what i had seen and asked her if that was the first time that had happened and how it got started. she told me she had sucked all of the partners more than once and usually sucked at least 2 everyday. i told her i was shocked, that i thought she was just fucking her cousin. she told me she was only fucking her cousin but she liked sucking her bosses because i made her feel powerful and that none of them had even touched her pussy much less fucked her.