For both it is hard to say, I think there is not just one thing...
For 1. my "favourites" are:
- licking my poo and smearing it on my breast
- going out naked of the apartment with a glas, going into the lift and going from -2 to +4 three times completely. Whilst peeing into the glas, drinking it and then edging my dick
- licking the toilet seat in a hotel
For 2. It is hard to top these, yet feasible. Though I wouldn't want to repeat any of these again... Maybe being in a rape role play with a girl and/or a guy or a group of people?
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