I have dabbled in this a bit so I will offer my two cents.
It is a very slippery slope. As the original poster mentioned, if the chemistry is right between the two--and the trust--the "humiliation" (I hate that word) banter can be quite fun. If not, it can be be hurtful and insulting--nothing more.
Here's my example, and maybe this doesn't quite fit the "humiliation" genre that the original poster is talking about. But it does for me.
One lady I played with was very good at getting into my head in this way. She would call me her sweet little slut, or remind me that she needed to fuck other men because my cock wasn't as big as she liked. She said it was a nice cock (probably average) but she knew that kind of taunting and humiliating turned me on. There were other things as well that she was good at. And there was a lot of laughing, sometimes at the ridiculousness of her comments while she tried to push the right buttons. It was all in fun. And it mostly worked on the few occasions we played that way.
On another occasion, this very same lady uttered a word to me while playing that didn't work for me, and I stopped her right there and told her that wasn't the correct path to enter. The word was "loser". She never said that to me again.
Call me a slut, tell me I have a little wee-wee, other men are better lovers. I'm good with that. LOL.
Call me a loser, dumb ass or some such other and it doesn't work.
It requires a lot of trust and understanding. I don't think it is easy to do. Especially on a first meeting. I totally get where Wicked Milf is coming from.
Everyone is different. To me, "play" is the necessary word. It's all in fun and play among respectful parties. Without that component, it might just be somebody saying mean things. I don't like mean.
I hope this makes some sense.
Gawd, I hope I don't regret posting this.