[Request] Has there ever been a guy you secretly wished had fucked your girlfriend/wife?

[EyefunJo]

I really enjoy talking with my wife about her past experiences. One of the guys I like hearing about was a colleague from one of her previous jobs. I’ve actually met him before — he’s good-looking, well-spoken, and has a really nice presence. This was back when my wife and I hadn’t met yet.

She told me she had a huge crush on him at the time. Unfortunately, he was very professional and kept strict boundaries at work, so nothing ever happened between them. They only became friends after both had left the company.

She was really into him back then — she even admitted to fantasizing about him while masturbating. Because they were colleagues, I can’t help but imagine what it would have been like if they had hooked up. I picture them in their business attire, sneaking quickies in the office when no one was around — on the couch in the break room, on the kitchen counter in the pantry, or even right at their desks.

Sometimes when my wife and I role-play, if she puts on a business suit, I’ll pretend to be that guy. She always gets noticeably more into it. I think deep down, she still has some regret that nothing ever happened between them.

[trunkster]

Yes, Danny D or Omar Williams.

[mysweetie61]

My fuck friend tells me all her desires. The one that stands out is her desire to have sex with a friend of hers, female friend. I’ve met her several times. She’s 32, very fit, 5’6”, about 125 pounds, assume she’s a B or C cup, dirty blonde hair.
My friend is 50, very fit, Chinese, 5’5”, 135, 34B and never has sex with another female.
I told her that I must be in the closet watching or she has to video tape it. Or I could participate if they want.
I’ve been encouraging her but nothing so far.

[Charlip]

Originally Posted by EyefunJo

Sometimes when my wife and I role-play, if she puts on a business suit, I’ll pretend to be that guy. She always gets noticeably more into it. I think deep down, she still has some regret that nothing ever happened between them.

I think it sounds to like you also regret her not doing something with him. Maybe you both need to call him up and get him over for dinner. It might lead to a fun night.

[512KenStron]

She met him in person at some school event returned home gushing about how professional yet friendly he was. Our kid was like me and said, He's just the school principal so he's gotta be nice to everyone.

But my wife kept referring back to the great impression he made on her for about 3 weeks and so I finally looked up the guy on the school web site and saw his photo. He could easily pass off for a Dwayne Johnson's kid brother so I started quizzing her on what she thought the man did so well to impress her. Of course is was that he was cordial and asked how he could help with anything and then he just listed and nodded the entire time she went on and on. That's how I figure it went from her description.

Don't know but I'm certain for a few months my wife's relax alone with her buzzing toys involved that principal a lot. I don't mind a stranger giving my wife motivation to jill a bit more frequent.

The guy left to a different school district the next year or two years later. There were only a few more encounters at school events between my wife and the guy and they left her perked up in a sense. I benefitted too of course from that enlightenment of hers.