[DLdapper]

What is the most painful thing you have put in your anus?
An entire chess set (plastic rounded pieces), beat that. Being horny can make you do questionable things.

What is the largest thing you have put in your anus?
A massive cucumber. Way cheaper than big toys and just as huge.

How do you like your enemas?
1-2 liters, while diapered. The type depends on the situation.

Would you go out wearing a butt plug?
Possibly, haven't yet though.

Would you sleep wearing a butt plug?
Probably not, but If I did it would have to be a plug I am very accustom too.

Have you ever had any bad experiences? (Things getting lost, too much pain... et cetera).
I've had several painful experiences. Mostly in my younger teenage years when I was horny and just starting my anal exploration, I didn't have proper toys or lube. Though I have learned from those experiences and safety is my #1 priority now.

Is anal a turn on, a punishment or both?
As a male, the prostate makes anal stimulation an extreme turn on. I also am up for anal 'punishment', but it isn't really punishment for me. >:-)

Is there anything in your anus right now?
No toys in there right now, but I can feel a massive shit brewing.