Re: My Girlfriend and her boss

Welcome to the community.

I would say there could be one or more reasons why this seems stalled:

1. there is always the chance that he’s grown wary of workplace relationships since their first encounter with it
2. it’s possible it really never stopped completely and the taboo of ‘cheating’ was alluring to both and now that’s gone with your encouragement
3. perhaps it did stop and has now restarted, but she’s reluctant to tell you about it

As to why you’re encouraging this: there are a number of aspects which play into it. Which ones apply to you I couldn’t say, but the fact that you’re comfortable with it does tell me you do have a high confidence in your marriage and in her love for you or you wouldn’t be able to suppress the anxiety of such an arrangement enough to enjoy it.

I would encourage some dialogue about her daily experiences in the office. I’d say to encourage her to show off her breasts for him and to make that planning part of your pillow talk. Things like being playful in overtly teasing him when no one else can see, for example. Let her feel comfortable and empowered by sharing these details with you. One of the things you can encourage her to do is to stand closer to him – much closer. Explain how she can cock tease him by letting her breast rest against his arm when she stands next to him, for example, something a woman not wanting a man’s attention would never allow to happen.

And, of course, consider sharing this site with her and let her see that you and you two as a couple are far from being alone in this interest.

It wouldn’t be a bad idea for you and her to stop by the chatroom, either.