Paulie73 said:
I agree he is being a bit of a douche bag but at least he's not being cocky with me about fucking my wife, but then again, he doesn't know that I know.
Exactly. He doesn't know you know. He may think you're a sucker, which is even worse. Your wife absolutely needs to level with him and let him know that she has a husband, he knows, and she loves her husband very much.
I am also aware that some of the hardcore cuckold fetishists on this site think your position is admirable, because they get off on the thought of being victimized, made to feel like a chump, a wimp and whatnot. I get the feeling this isn't you.
Paulie73 said:
Thats one of the biggest reasons why Jess doesn't want him to know, she fears will change, start being an asshole with me and start demanding more time with her, another reason is she can handle office gossip about her "having an affair" since no one there is in a position to talk, but she doesn't want to deal with the gossip of her husband being "in on it".
In that case, your wife might want to add "...and if anyone finds out, I won't stop until I see you and everything you love destroyed. Have a nice day."
Seriously, though, she can talk, too. And I'm sure she's more than capable of painting a not-so-pretty picture of him, should he start demanding too much. I know from experience that men ought not to start a gossip contest with a woman
Ground rules, ground rules -- he needs to have his position explained to him. You seem like a nice guy. If I were you, I'd expect as much. If I were your wife's casual buddy, I'd be expected to respect those ground rules.