Group dare
There's a type of dare I really like (I can't remember if I first saw it on this site or somewhere else) - though you'd need the cooperation of 2 or 3 female friends.
Basically you arrange to meet up somewhere public, like a coffee shop, then when you get there the one who's wearing the longest skirt has to do a forfeit. At the mild end, she just pays for the coffees. Getting more risky, she has to remove her knickers and keep them off until she gets home. You could do something similar at a beach, with most conservative swimsuit.
I like it because it gives you the dilemma of wear something safe and get the forfeit, or (probably) avoid the forfeit but be wearing something that's pushing your limits.
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