I've been thinking about this for some time too. Since long, I have been trying to convince her to sexually enjoy others. She is somewhat convinced but still maybe too scared, maybe too shy, maybe too inhibited to take the plunge. She is not a person to be forced or tricked into something, that would backfire. She must be persuaded. So far, I persuaded her to cam with guys (sexual - but only when with me), going out with somewhat sexy attire with no underwear, flashing a little (some pics in my thread) and the furthest we've gone was same room but same spouse sex with another couple. She has expressed to me that if it ever happened, it would never be with any local people - being afraid of they might be pestering (the couple were foreigners). Now that is quite a hindrance I have to overcome. It is definite for us both that such thing will not happen with any current friend. So, I've been thinking, maybe someone I know online could help, slowly and gently seducing her. It might place thoughts in her, now that I'm being away from home for long terms and that she knows I am more than fine with this. The problem is:
1) Like trevn here, she is not out in the world enough socially; at work or with the kids.
2) If my involvement would be revealed, it would put an end to it all.
So I'm thinking, I'd first meet with the guy face to face and if he is trustable we'd sort out a plan. I'd introduce him to her as a friend somewhere outside and make up a reason for her to give her phone no to him. Then, he'd take it from there.
The problem of how to find such a trustable person she'd be fond of and how to be sure he can be trusted still stands. Of course, the best and easiest for her first time would be another couple whose fem side would seduce her to be with her man. She'd be up for that but you don't come across such everyday in your life