As you are aware, I am a newbie to the scene, and enthusiastic about it. By the same token that same enthusiasm, will probably cause many mistakes.

The story straight is I have managed to wiggle a woman into what is pretty much a suckers bet, though she went in on it full willingly. (I will admit if I lose, which is a possibility, it's going to suck)

The bet's terms are simple, Whoever wins the bet determines the terms or forfeit.

I am looking for ideas, to deal with in a semi-public manner, possibly private, (she seems adventurous) setting. I have a few ideas of my own, and I would like to bounce them off of you people first, to get a feel for what might and would be considered 'too-far' for a first time. I will be avoiding anything harsher than a spanking. and even that would have to be culmination of her willingness, mood, and arousal.

Obviously these are the non-vanilla ideas

Semi-Private:
_____________
Having her go without underwear for a week
Remove all tanlines
Ben wa balls
A kiss on her nipples every half hour during one night (Obviously out of sight of the vanilla people)
Only allowed to wear skirts for a week/month possibly without underwear


Private:
____________
French Maids outfit one day a week for a month
Ownership for one night
A display of masturbation
An hour of running a feather over her body


Please, like I said, any ideas are welcome. There is about 2 weeks before the bet is executed.