The riskiest thing I've ever done is probably a late night bike ride I did a few years ago. My intention was to "finally!" take a series of naughty selfies I hadn't been able to take earlier. Regrettably my crappy camera failed me big time.
But... I rode on the public bike path - very visible next to a main road - wearing black stockings and a tee instead of cycling gear. I even pedalled in high heals for a bit! I minced about next to the road, dressed like a desperate sissy in heels, stockings and a net suit. I posed naked in an underpass, right under bright street lights!
All this happened "not too late in the night" and very publicly in places that saw quite a lot of traffic. And not a single one of the photos were worth saving...
(Yup - I was pretty drunk. Yup - I have thought about trying it again.)