So, would you go for it?
Definitely. That much money would be worth a (small? Small, right?) risk.
If you lost, would you enjoy it?
...Possibly? If I could just accept and try to enjoy it, I guess?
What would you enjoy most?
Probably... The students and faculty being able to touch me as they wish, when and how they wish. The sense of surprise would probably be the best bit.
Describe how you'd feel, what would be the most embarrassing about it.
I'm not really sure. Probably having to travel to and from the school naked. It'd be one thing to be naked in a place where people know why you are, it's another for random people passing by to see you.
Are you insecure about being nude around others? Why?
Kinda. It's not something I have any real experience with, and I've been raised in a way/place where any vaguely deviant things were shunned. Guess it had some effect, at least.
Was there any teachers in your high school you'd love to give oral too? If yes, describe them.
Not... that I remember, I think. The vast majority of them were either old enough to be friends of my grandparents, or a pain to be in the same room as. I had a fun college.
Would you spit or swallow if a male teacher came in your mouth?
Spit. Probably.
Was there a specific classmate you'd want to spank you? If yes, describe them.
No.
Wait, no. I lie. There was one, a friend I lost touch with just after college. He'd dress fully goth-like: black clothes, long black belted coat, massive black boots, and was one of the kindest people there. Him. (Maybe he'd be gentle *cough*
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In regards to the faculty/students being allowed to touch you wherever and whenever, describe your ideal grabbing
Eh... Walking straight up to me, with eye contact, doing whatever they wanted without going far enough for it to be called anything more than "touching".
If you won, what would you do with the money?
Spend a lot of it. Probably quickly. Try to be responsible with whatever's left after the first week.