Rhysis

My wife and I have yet to have our first experience. We've talked about it some and we've come to the conclusion that, if we do decide to take that step, we would be a lot more comfortable with someone who was experienced. It would be way too wierd for us otherwise.

I would say talk to your wife and let your concern be known to her. Let her know that this has raised a red flag for you and talk about whether or not you guys should considering breaking ties with them. That may be a little bit extreme, but if you're becomming uncomfortable with him, it may be best if your only future playdates are as two couples.