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I would say it would seem more organic if your wife was involved. Pick a time where you know you will be with your buddy and have her text you a couple racey pics. Ideally he is next to you at the time, if not, just show him and see where the conversation goes. “Man, I think my wife wants it...

I have a couple ideas. I’ll respond a little later

Where are you two when you hang out usually? Is your wife there?

I’d start there. Not her completely naked yet. Almost working your way up to it. A couple good ones of her showing her assets off. See how he reacts, don’t jump right into the “hey, I want you to fuck my wife while she blows me” conversation yet

Have you ever showed him a provocative picture of your wife?

Is this a buddy of yours? Do you two see each other often?

Is the guy interested?

Definitely a step closer and that was incredibly hot. Thanks for sharing