As with everyone else, I think it's unlikely that this is a genuine question, but I've known older virgins, so..
Having someone - a close friend! the wife of the man! - watching this is unlikely to be a good idea. What happens if she decides in the middle that actually, she can't cope with seeing him having sex with someone else? What happens if it turns out you're hurt by him or even better as a partner for him than she is? It'd be far better to book a weekend away with some single man you'd trust.
You're more likely to enjoy the experience, who ever it's with, if some guy's penis is not the first thing that's been inside your vagina. Do some shopping at LoveHoney or similar.