So, would you go for it?
For a shot at 20 million? Yes.
If you lost, would you enjoy it?
No.
What would you enjoy most?
The money 
Describe how you'd feel, what would be the most embarrassing about it.
All the stares = extremely uncomfortable.
Are you insecure about being nude around others? Why?
Now? No; I have lost a lot of weight. Back in HS? Yes; I was chubby.
Was there any teachers in your high school you'd love to give oral too? If yes, describe them.
Nope.
Would you spit or swallow if a male teacher came in your mouth?
Spit.
Was there a specific classmate you'd want to spank you? If yes, describe them.
No! GIVE ME THE PADDLE!! xD
In regards to the faculty/students being allowed to touch you wherever and whenever, describe your ideal grabbing
INVASION OF PERSIONAL SPACE!! But if it had to be done; my ass would be my 'ideal' grabbing.
If you won, what would you do with the money?
Can't list it all, but one would be; Private Jet + Trip around the world.