What is the most painful thing you have put in your anus?
Enema with quite some cayenne pepper
What is the largest thing you have put in your anus?
The largest dildo I own 
How do you like your enemas?
The ones I like: regular luke warm water in the shower 
Would you go out wearing a butt plug?
Done it
Would you sleep wearing a butt plug?
Yup
Have you ever had any bad experiences? (Things getting lost, too much pain... et cetera).
One plug's base wasn't solid enough, luckily got it out
Is anal a turn on, a punishment or both?
Mostly a turn on, but the right way can be punishing as well
Is there anything in your anus right now?
My medium plug