Newbies at the nude beach or resort.
Because it's fun to try to figure out how "far" they're gonna go, particularly when they arrive fully dressed. You can usually tell they're newbies from the hesitation they display, and the way they look around like it's the first time they see people just hanging out naked. The expression on their faces and the way they try to conceal it can be priceless sometimes.
I like to make "bets with myself" on whether they're going to undress or chicken out. Sometimes I get it right; sometimes I'm totally wrong. Some will go topless but end up never going fully naked. Others will just chicken out completely. But my favorite scenarios is when they hesitate, hesitate...and then "out of nowhere" take the plunge.
Sometimes they walk off, disappear for a while, and come back naked holding their swimsuit or towel. That usually means they went off somewhere less populated to get their "nerve" to get naked; and once they found it, decided to stay naked around everyone else. Others just sit there for a while, and gradually wiggle out of their swimsuit in the hopes that no one will notice them getting naked.
But my favorite thing is when they find themselves naked; and suddenly get "happy" about it. They suddenly feel "liberated." That can lead to some priceless moments where they come out of their shell and let their legs swing right open and drop all their inhibitions. The first time my wife went nude at the resort, it took her a long time to wiggle her way out of her sarong. But when her sarong finally slipped off completely: she was within minutes jumping in and out of the pool, talking to people, sitting/lying around legs open with her kitty in full view. She was just excited about finally being completely naked around other people. I'm sure that she made a lot of gentlemen's day by the way they were smiling at her.
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