What is the craziest thing you have ever done in the nude? (excluding sex) For me, the craziest thing I have ever done naked was break into my neighborhood swimming pool at 3:30am to go skinny dipping. I never thought I would ever do something that crazy. Even while I was climbing over the fence I was thinking "Oh my God, I can't believe I'm doing this. Oh God, I can't believe I'm doing this." But soon enough, my shorts were off and I was splashing around in the pool totally naked. Even though I was paranoid that was going to get caught I still loved every minute of it. To feel the cool water all over me was so exhilarating and refreshing. Hours later when I was at work I had a smile on my face thinking about it. I tried again the next morning, but I almost got arrested. (oops) I was lucky to get away and I haven't gone skinny dipping ever since. If I could do this again with a 100% guarantee I would not get caught I would totally do it.