I think the most fun dares are in stores etc, you dont need to buy anything if you dont want to.
A little dare is to wear pantyhose or stockings under your male pants, but they need to be thin so it must be obvious that they are stockings
Example now go to a big store, like target or something like that and walk with out shoes for like X amount of minutes, 10 is good enough. if you want it to make it yourself harder you can stroke up your pants to your knees and go for a longer walk in the store.
Everyone who looks down can see your feet in thights, pretty humiliating and a turn up for me
Hope you will enjoy it!