[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.