This sounds really hot. My advice is probably bad, because this is my fetish, but I'd just dive straight in if I was sure that the conditioning couldn't be reversed. If you choose to go deeper, do you mind keeping us updated? I'd love to listen alongside and see who can go deeper.

That sounds like a lot of fun. Since this is my fetish, it's probably a bad idea to listen to my advice, but if you're certain that it's not going to go away, why not go all in? If you do, tell me so I can listen along with you.