Well since the OP hasn't replied to his original post in over a month, and it was his first post, my advice will probably be mute, but here it goes.....
Why not have her do him first, one-on-one, just the two of them, with him knowing you know about it (If you're cool with that), to get him more comfortable first.
We've done that before and the results were successful.
The story:
He knew we/she wanted a three-sum with him but he had never done that before and was uneasy, but at the same time he wanted to fuck HW Sharona, but didn't know if he could do it with me there.
So we made a deal.
She would stop over on her way home from work to have sex with him one-on-one. Then later all three of us would meet out for drinks with other friends, then at the end of the night we would go back to his place for an MFM.
He agreed to that and that's what we did and it worked flawlessly.
HW Sharona fucked him on her way home from work, we went out that night with him and other friends, then ended at his place for an MFM. We offered to bring some 'little blue' to help him along and he agreed to that. He said it would help him be 'Strong Like bull'
The three of us ended up having a pretty good time that night!
But I did tell him if he fucked my wife that afternoon and didn't show up that night for drinks, even if he decided to back out from the three-sum, I'd be pissed
, the deal was he had to
AT LEAST show up for drinks afterwards
