Should I?

After 30 years, I really wouldn't mind if my wife needed to experience some strange just for the reboot and self-validation. I actually think the idea is kind of hot, and she WOULD kind of owe me, lol. We've had 3sums in the past, and all but one were women, and I was always there. I was actually comfortable with all of them, and just loved the watching, even with the guy.

Once or twice a month, she goes out drinking with her coworkers. She's always behaved, and yes, I know for a fact that she has. She has this one coworker that's always been a little needy, needs women to be "mom" to him, and he always buddies up to my wife. He got home a few nights ago, and his wife had packed her things and left, and he's pitiful now.

I can see it happening... he and my wife the last two at the bar, and he's lonely, and she's a bit tipsy. That's when she's always easiest. I can see them hooking up, and I can see her trying to hide it from me. I can already see it in the cards, and I really don't mind, but I'm not sure how to approach it.
Do I let it happen and let her deal with the guilt in silence?
Do I keep close tabs to keep her from going that far?
Or should I sit her down and just out right give her a hall pass before it ever get's here?

Wives, what is your opinion?