Hmm, I actually had to stop and think about this for quite awhile as it was so long ago. My sister saw me naked a few times, but I assume that doesn't count because when you live with your family for some time it's inevitable.
So, let me see...I was raised as a petrified prude, so it wasn't until college that someone saw me naked as I wouldn't even let people see me with my shirt off prior to then.
There are two times that I will write out because I am actually not sure which came first:
1) My then-gf in college pulled my pj pants down in front of her roommates in college. It was to humiliate me, but I actually like it and just got fully naked. I stayed naked that entire night and was subsequently naked a lot when I was staying there for the rest of the college year. It was really fun for me, and her three female roommates stared at me any time I was naked.
2) Around the same time, I met up with my best friend and his family at a resort near the college, and I went swimming with them at the hotel. I wanted to change before driving back to college, so my friend, his sister (she was 18 at the time), and I went back to the hotel room to change. My friend hid around the corner, but his sister stared at me while I changed, then she went into the bathroom to change herself, but she left the door open enough that I saw sideboob.
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