Wife's first date

[Nazareth]

Yeah, that guy definitely has some issue(s). I'm guessing he may not be as divorced as he says he is, or emotional issues related to their breakup... something along those lines. Could even be some issues related to boss/subordinate roles, but, typically, where there's a will, there's a way.

Whatever it is, it's a shame he isn't taking advantage of the opportunities your wife is providing him. The touching, kissing, and oral sex are hot and exciting, but actual fucking is on another level entirely!
I would just enjoy the ride you are on, and let things progress naturally. It's apparently beneficial to you and them, and nobody is getting hurt.

 

[Custer Laststand]

Can't figure this guy out, he clearly wants to fuck [my wife] but he won't let himself go through with it.

Your wife's stand-off with her boss may be for one, or both, of the following reasons.

1) Her boss may be deterred by their boss-subordinate relationship. Because of that, he may fear that if he establishes a sexual relationship with your wife that includes fucking her, he may be setting himself up for a future sexual-harassment charge, and possibly a lawsuit, that could cost him and/or his company a great deal of money.

2) Your wife may be deterred because she feels it is supposed to be the man's role (in this case, her boss's role) to initiate sex.

Thus, you might suggest to your wife she may be able to move her relationship with her boss to the next level if, during their next date, she takes the initiative and whispers in his ear, in a low sexy voice: "I want to fuck you." Or, "I want you to fuck me" (her choice).

If your wife makes it clear she is taking the initiative, that might have the effect of overcoming the reluctance her boss is feeling because of their boss-subordinate relationship — if that's the source of his reluctance.

Addendum: it might also help your wife's boss overcome any reluctance he may be feeling because she is married (to you).

 

[Bishot]

Your wife's stand-off with her boss may be for one, or both, of the following reasons.

1) Her boss may be deterred by their boss-subordinate relationship. Because of that, he may fear that if he establishes a sexual relationship with your wife that includes fucking her, he may be setting himself up for a future sexual-harassment charge, and possibly a lawsuit, that could cost him and/or his company a great deal of money.

2) Your wife may be deterred because she feels it is supposed to be the man's role (in this case, her boss's role) to initiate sex.

Thus, you might suggest to your wife she may be able to move her relationship with her boss to the next level if, during their next date, she takes the initiative and whispers in his ear, in a low sexy voice: "I want to fuck you." Or, "I want you to fuck me" (her choice).

If your wife makes it clear she is taking the initiative, that might have the effect of overcoming the reluctance her boss is feeling because of their boss-subordinate relationship — if that's the source of his reluctance.

Addendum: it might also help your wife's boss overcome any reluctance he may be feeling because she is married (to you).

I don't think either of those applies. She has given him oral sex twice and he has put fingers inside her, so whether they've had intercourse or not, they are having sexual relations and he has already violated any boss-subordinate taboos or policies that exist in this case.
And she has very explicitly asked him to fuck her. Both by text and in person, even while standing naked in his living room. All his other actions indicate that he wants to, but he's failed to follow through 3 times now.
Personally I'm starting to think he has multiple hangups and issues, possibly related to his failed marriage and divorce. Control issues or the like.
But in any event I think he blew it, her enthusiasm for that relationship has fizzled somewhat.

 

[Custer Laststand]

....... And [my wife] has very explicitly asked [her boss] to fuck her. Both by text and in person, even while standing naked in his living room.

Taking the initiative in that way was admirable. My congratulations to your sexy wife.

All his other actions indicate that he wants to, but he's failed to follow through 3 times now.

Maybe he has a problem with E.D. (although your wife sucking his cock successfully would seem to indicate he doesn't), or with premature ejaculation when he's actually fucking a woman.

Personally I'm starting to think he has multiple hangups and issues, possibly related to his failed marriage and divorce.

And maybe his inability to perform adequately while fucking underlies his failed marriage and divorce. Hence, he is "gun shy."

But in any event I think he blew it, her enthusiasm for that relationship has fizzled somewhat.

It must be tempting for your wife to conclude, "three strikes and he's out." But, I suppose an outside possibility may be that he has some sexual fetish that falls outside the bounds of conventional fucking. Maybe she should try asking him (for instance) if he would like her to fuck him up his ass with a strap-on dildo, or otherwise play the role of a dominant and treat him as a submissive. Or, more broadly, ask him what he would like her to do to him. The former might seem out-of-bounds for an employee-boss relationship, but the latter might come across as an acceptably indirect approach.

 

[Bishot]

Seems like E.D. might indeed be an issue for him, based on what she's told me about their encounters. I'm going to let her manage that situation as she sees fit, in the meantime I'm seeking other guys that will hopefully give her a better experience.

A member here on the forum is traveling through our area soon and we're planning to meet up with him, hopefully he can show her how fun hotwifing can be.

 

[Custer Laststand]

....... A member here on the forum is traveling through our area soon and we're planning to meet up with him, hopefully he can show [my wife] how fun hot-wifing can be.

Any update, Bishot, on how this worked out for your sexy wife...? (It's now mid-January 2021.)

 

[ROBOCOCK]

any news ? if he didnt fuck her he is an idiot ? if it was me i will fuck her on the first date

 

[AstaSilva]

blueballed again

 

[Bishot]

No updates about that guy, things pretty much fizzled out.

We did meet up once with forum member Shavedballz when he came through our area, I made a separate thread about it somewhere. Tried to set up a second meet with him but it fell through.

She also found another guy that she started seeing, I made a separate thread about that guy also but haven't updated it in a while. Short story there is that there's nothing much going on, he has probably friend-zoned himself. And the Covid is bad right now and is putting a damper on everything, and I've been busy with other stuff. So no real updates to provide.

 

[xspree]

My god this thread got me rock hard!

Enjoy my wife as a prize

Where do you live? I want to have her.

 

[crt]

I didn’t start this thread, I just contributed today

 

[crt]

Ok