Wife Cuckolding Me with her Boss

Discussion in 'Real Life Experiences' started by NewSissyCuckold, Feb 14, 2017.

  1. NewSissyCuckold

    NewSissyCuckold New Member

    My wife had not been happy with our sex life, and I had known that for awhile. About a year ago after a few long talks we agreed that she could see other people so she could have those needs met. In the beginning she would go out and meet with bulls and it all went smoothly. I was new to this and was a little jealous, but I was happy that she was having fun.

    This past summer she started seeing her boss, and the dynamic changed a bit. They wanted me to be there when they would meet, and he wanted me to dress like a maid and wait on them and do housework whenever we would be at his place. I was hesitant, but my wife said she really liked him, and that being the maid for them would make him happy, and that if this arrangement worked out it could lead to a raise or promotion for her. I didn't want to stand in the way of something like that and agreed (reluctantly). My wife was very appreciative, and he already had a uniform ready for me.

    This has been the arrangement for the past month, and wanted to know what more experience people thought about all of this.
     

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    Toson, Ilovemywife, chootdas and 2 others like this.
  2. JeffHouston

    JeffHouston Well-Known Member

    Good job loving and supporting your wife. Doing things her way and accepting her desires for your complicit service is great. Also, pay attention to your needs while you are experiencing fulfilling hers. You may find that you are happier joining her and helping her sex life to be better. Maybe you are helping with her job too.
     
    chootdas likes this.
  3. NewSissyCuckold

    NewSissyCuckold New Member

    It was tough the first time we went over to his house. I had never crossdressed before. When we got there he said to her hey honey and they kissed. He looked at me and said hi Andy, your uniform is in the guest room down the hall.

    When I got to the guest room and saw it hanging on the closet door and all the other stuff laid out on the bed I'll admit I felt a pit in my stomach. While I was putting it on I was thinking, Christ this guy is young (31), wealthy, sleeping with my wife, why do I have to wear this. I kept thinking that I was helping her out.
     
    Ilovemywife, chootdas and JeffHouston like this.
  4. JeffHouston

    JeffHouston Well-Known Member

    I also think that you are important. Your boundaries are just as important as anyone else's boundaries. I'm a big fan of trying anything with or for my wife. And, not everything fits. So, if you want to go then go. If you want to decline the invitation then don't go. You accept your wife and are not asking her to change. Good job reaching out for connection and advice. There are lots of good opinions in the group.
     
    chootdas likes this.
  5. NewSissyCuckold

    NewSissyCuckold New Member

    when we were driving over she said she really appreciated me doing this for her. She said she likes her boss a lot, and if this was something he wanted she wanted to make it happen. I told her I wasn't into the crossdressing thing, but I loved her and would do it.
     
  6. JeffHouston

    JeffHouston Well-Known Member

    I think that's beautiful.
     
  7. NewSissyCuckold

    NewSissyCuckold New Member

    when i came out to the living room they were sitting on the couch together. He seemed happy with how I looked, my wife looked a little guilty. I dont think she ever planned on it where it did with me dressed like that being their maid.
     

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    Last edited: Feb 14, 2017
    JeffHouston likes this.
  8. JeffHouston

    JeffHouston Well-Known Member

    I'm guessing that you read it right. I have difficulty feeling good or comfortable about sexy playtime things if my wife is not excited and pleased.
     
  9. NewSissyCuckold

    NewSissyCuckold New Member

    If she was feeling that, it went away pretty quickly when they started kissing on the couch.
     
    JeffHouston likes this.
  10. rob788

    rob788 Guest

    If that's what she wants and continues to receive pleasure from him and for your services as she wants, I see no reason to change the arrangement.

    I don't know whether her boss has more employees, but here's a tip: My wife and her boss decided early on to keep their office behavior completely professional to avoid suspicion from other employees. She says it's possible one or two might be suspicious of his and her fucking but only because he takes her with him occasionally on overnight business trips whenever he needs notes taken, internal files or help with presentations. So far, no one has any reason or evidence other than that anything is going on between them.
     
  11. NewSissyCuckold

    NewSissyCuckold New Member

    They keep their sexual relationship away from work. I think at some point he implied to her that if I would agree to serve as their maid then it could help with moving ahead in the company. I don't think he said it out right. I'm not into dressing like a maid, but if it can help her get ahead then Ill keep doing it.
     
    christinebitg likes this.
  12. JeffHouston

    JeffHouston Well-Known Member

    I think that he might be using both of you. Just seems too blatant and too inappropriate.
     
  13. NewSissyCuckold

    NewSissyCuckold New Member

    I think he is used to getting what he wants, and its like having me do it just because he can. He is pretty straight up, and if he said that he would promote/give a raise I believe he will. Though I know it could be a set up for nothing.
     
  14. JeffHouston

    JeffHouston Well-Known Member

    I think that the key is for you to enjoy serving and helping your wife. That's awesome and this is what she wants to try right now.
     
  15. NewSissyCuckold

    NewSissyCuckold New Member

    Thats what I remind myself every time we go to his place and Im getting dressed. I'm hoping he follows through with what he told her. She is into him, and she lets me know that she appreciates what Im doing.
     
    JeffHouston likes this.
  16. christinebitg

    christinebitg Well-Known Member

    I was thinking about this a little more.

    In her company, who writes the checks for travel expenses? Or who does the review of those expense reports? If there's someone besides him who knows that she's is not paying for a room of her own, that person knows they're sharing a room.

    xoxoxo

    Christine
     
  17. jean.soumis

    jean.soumis Guest

    I fully agree. I hope your wife appreciates how much you love her and shows that to you at times when she is with you alone.
     
  18. jean.soumis

    jean.soumis Guest

    Again I fully agree. Your wife needs you right now, way beyond what both of you anticipated, yes, but the prospect of your role in it may yield further gratification to her (promotion/raise) and that in turn will make her appreciate your determination to humiliate yourself in front of her boss in order ultimately to please her. If I were in your shoes, I'd go along with it too, there's no harm in it for you so far. Of course, you need to reflect on possible limits in case your wife's boss comes up with new ideas that might exceed what you could tolerate. And do not allow yourself to act spontaneously in a way that you allow your limits to be transgressed in the spur of the moment and out of fear that your refusal might backfire on your wife's standing with her boss. Even as a cuckold you do have the right to be respected, as a husband and as a person anyway!!
     
  19. NewSissyCuckold

    NewSissyCuckold New Member

    Hi everyone, it has been awhile since I first posted this thread. My wife is still seeing her boss and did give a promotion and sizable raise. I still have trouble sometimes accepting the role of being his maid when we go over to his place, but my wife said my willingness to do it helped. The biggest pain right now is a few months ago I made a face when given a chore to do at his house which was going to be difficult to do (the uniform is pvc with a hobble skirt that lets me take 3-4 inch steps) and the next time we went over he has a female mask to add to the uniform.
     

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  20. canadianwittol

    canadianwittol Well-Known Member Founding Member

    My wife slept with my boss last month to secure a promotion for me.

    Oddly enough I would say it's been one of the least humiliating encounters my wife has had. He seems genuinely concerned at making sure "I don't find out" (he thinks I don't know) and my wife assures me that in their conversations he both likes and respects me very much.

    He's an older divorced man who doesn't seem to have much of a love life, so in a strange way I've sort of thought "good for him" he got to have a crack at my wife. I feel a little awkward playing as though I don't know what's going on, but more to the point I am blown away by his poker face that we can sit across a table from each other and he will not let on in any way that he's repeatedly boned my wife.
     

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