Joking around is fine, but any serious conversation is weird. For example, I always joke about wearing thongs with my guy friends, which is fine. But if one of them were to straight up ask me what kind of panties I was wearing, that might be a bit odd.
I personally don't. Unless the guy is random and I barely know him. But it depends on the conversation. Of course I'm not going to tell some guy who I'm not "talking" to at least why type of underwear I have on.