Milovana.com

Anal, allowed to cum, selfbondage, perhaps a bit of sissy stuff, and watersports, and there must be much I have forgotten to put, so yeah.
Limits: Scat, pain, blood, suicide(for all those jokers), and anything financial-related.

Hard to say. One person's humiliation is another's lovely evening out.

That being said, he should ruin an orgasm, coat his finger, then finger fuck his ass. .. then ruin another and lap it up. Alternate until he is broken.