>>2891501I like this idea.
The way I imagine it could playout is, they meetup in a park in the city, she comes wearing a casual sundress. He tells her to give her underwear and bra to him, and they go for a walk around the city. As they go around, every once in awhile he tells her to lift her dress up above her head for the next X seconds. Maybe it's somewhere secluded, maybe it's somewhere with people around, but regardless she has to do it. Maybe it starts in an alleyway, progresses to inside restaurants, then to populated tourist spots. At one point he has her do a naked photobomb of tourists getting their photos taken. They keep moving so there's never too much attention, while she gets increasingly embarrassed and humiliated.
At the end of the day, before they go their separate ways, he tells her to give her dress to him and then he departs, leaving her to try to find her way home wearing nothing but her shoes.