I did it for the first time this last summer -- so I was 14. It is the only time so far but I loved it so much and would love to do it more. I was with three guys (age 16 to 18) who caddie at the club where we belong and where I sometimes work on boats. The club had closed and we stripped down and jumped into the Sound where boats dock. They was all older than me and it was really cool. I think I posted about it somewhere else on here.
A friend of mine is rich and has this really nice in ground pool and he always skinny dips in it, and when I go there, I skinny dip with him. It's cool that his mom comes out with snacks and sees us naked.
I love skinny dipping. The first time I went was when I was thirteen and my best friend and I went together. We had seen each other naked before so it was no big deal. His grandpa has a cottage on Lake Michigan with a private beach so we go skiing dipping in the big lake. It is so much fun and relaxing!