At about 8, my father, uncle and myself spent a weekend at a "fishing hole' - no cabin, but a mobile home out in the woods. On the second day of heat and zero fish catching, we went for a swim to my surprise, in the nude. It was great, it was exhilarating and it made my dad and uncle seem so 'wild and cool'. That happened a few times over a couple of years.
My father passed away when i was 12. That following summer, my mom let me spend about two months with my uncle, aunt, cousins to sort of let me regroup as she was dealing with a lot of the aftermath. My uncle/aunt weren't nudists, nor even clothing optional - just relaxed. They had a pool and skinny dipping was the norm (two cousins, boy and girl younger than me). Many times we would wander in the house still nude, which after all my experiences outside, seemed newly exhilarating.
My mother and I moved to a home in a crowded suburb two years later, but it had a privacy fence and nice little in-ground pool. I would get home from school about two hours before she came home from work. Naturally, I skinny-dipped constantly, and once fall and winter arrived, would go nude a few hours every day inside. The following summer when we opened the pool, I was always allowed to have friends over, and two of my closest friends (male) started skinny dipping. There was always an extra sense of freedom when going nude with others.
I eventually started to boldly swim in the early morning, to start the day the best possible way, knowing my mother was still in the house. It wasn't so much that I was being more bold, more that I was simply more comfortable, and wanted not to be 'sneaking' around in the nude. She saw me skinny dipping several times, as the kitchen window looked right out to the pool and backyard. At first, I was naturally nervous, but she never made a big issue of it, asking me that first time had I outgrown my swimming trunks as I would come in wrapped only in a towel. One afternoon after school was out, I came home from summer league softball and she was out by the pool. I just thought 'what the heck' and went out with my towel and jumped in. It was a non-event, because once I left the pool and sat across from her, we started talking about my dad, and her telling me how he loved going nude. It may have been the first, really genuine conversation about my dad we had since he died.
The next morning, I stopped at the kitchen and asked if she wanted to join me for a swim. She said she would be out later and she did. After what was bluntly a lot of nervous energy diving and swimming in the pool, everything was just tranquil and completely open. We spent about four hours talking about my dad, our family, friends, then movies, music and things I would never think to just 'chat' about with my mother. It was sort of an overcast day, and a drizzle put an end to the time that had flew by to our amazement. I said I hated we had to go in, and she just picked up my towel with her stuff and went inside. We spent the rest of the day inside in a new routine of liberation.
Once I got my driver's license, and her work became more demanding, we rarely spent time together, and even when we did, it was sadly inconvenient to relax in the nude it seemed, so it sort of just stopped other than rare times or early in the morning routine.
So, there are three moments in time for me, and I don't even consider them my first experience. That would be at college, my fourth weekend in school, but that's another story and I've all ready defined the concept of 'long-winded'.