It had to have been when I was about 13-14 my childhood bestie and I would play video games (this was before I discovered my trans identity) We would often play shirtless, but seeing as it was just me and him playing video games we'd always strip down and play and see who could beat one's high score on the game
I was probably around 12. We lived in a remote wilderness area in British Columbia, in Canada. On warm summer evenings (which were rare at 1200 m above sea level), I sometimes would slip away from our cabin and go wandering nude in the woods, enjoying the fresh air and feeling of breezes whispering against my bare skin. I would go nude out on our lake sometimes.
I often wish I had done that more. A girl that came up to the lake to her family's cabin told me that she and her sisters skinnydipped in a secluded cove some distance up the lake, where there was a swimming raft. In retrospect, she probably would have been open to going there together, but I was too shy to think she might be ok with it - but since brought up the topic, she probably would have joined me! It would have been my introduction to social nudity rather than being solo all the time. I suspect the rest of her family was casual about nudity.
Thereafter, it was pretty rare that I got a chance to go nude. After I came to the States and went to college, I became more curious about it, and when I got married at 26, my wife and I skinnydipped and made love on a beach in Northern BC, on our honeymoon, and have skinnydipped off and on since, with some nudity around others occasionally.
I can remember being allowed to play nude when I was about 5 or 6 ish then at about 9 or 10 being told by my parents that I had to start dressing which seemed a bit odd so I continued being nude in private when possible since then.
I didn't really understand much about nudism until later in my teen years. I didn't know of it, to detail just how much I didn't understand it.
One night, I tried to sleep in just underwear and thought that I liked it. I was around 9 or 10 then. I never tried again though because of my mother being a very strict woman who was constantly against certain things. Eventually, a year or two later, I decided to try again and she found me sleeping in my underwear. She asked why and I told her it felt more comfortable. She didn't seem to have a problem with it. The following night, I decided to try and sleep nude. She came in and thought I was "fooling around," yanked the blanket off, and grounded me for the next month. I never tried anything of the sort again.
However, I was always curious and one day when I stayed home from school and my mum was at work, I decided to just walk around naked. It was a little chilly but it felt natural for me. I never slept naked until I started camping, which was around when I was 18 or 19, though I only did it once or twice and it wasn't overnight. There are times I do wish my mother had allowed me to practice nudism because it would have taught me to be more self-confident about my body and maybe I would have a wife and children now. Everything I know about sex, I had to read from books or online... She didn't want my father teaching me anything. Suffice it to say -- she didn't want me to "grow up."
When I started camping at my uncle's a couple of years later, I had invited a few friends and one who eventually became my brother. I told them about me wanting to practice nudism and they even gave it a try themselves.
While I don't mind being a nudist on my own, the company is more enjoyable. After a while, we even invented some nudist games just to break the ice between us from time to time, though there was rarely any. Now it's just my brother and me that practices it every once so often. I'm always looking for new friends to hang out with, nudist or not, though. So maybe we would find some new nude company eventually!
I guess one could say that my first nudist experience was when I was 14 or 15. I used to go out into the woods behind my home (there were a ton of woods there). I used to undress and simple hike or walk nude - climbed a couple of trees and just enjoyed the fresh air and sunshine. Wore sneakers only. My dog (a beagle) was always with me. I never ran into anyone else but I used to hide my clothing just in case.
In my later teen years I vacationed each summer in Maine and had a small boat. I used to land on deserted islands and loved to explore naked. Again I never ran into anyone. It was so nice.
One in college I joined a group that went skinny dipping often - my first experiences with others (except for gym class showers). I found it true happiness. I've never looked back - been into nudity ever since. At first I thought I must have a loose screw or something bu have come to realize it's pretty common and for the most part normal.
I've been a photographer and love to photograph the nude form (male or female). It's not easy to produce a creative fine art nude - not just a photo of a naked person.
As a little boy, I used to run through the sprinklers on hot summer days naked as a matter of course and didn't really think anything about it. ...at the time. As a teen, I would regularly lay out in the back yard after school but was careful not to get caught.
I finally took the plunge when I was 17. I went to Red White and Blue beach north of Santa Cruz. I parked the car, got out, and ...without any hesitation at all....stripped naked. The breeze on my skin was an awesome feeling! Wearing only my shoes and carrying only my keys, I walked the trail down to the beach, passing (clothed) people along the way without any nervousness at all! When I got down to the shore I found that , excepting one other person, I was the only one naked! But I didn't care! I spent the day wandering around, jogging along the water and even playing frisbee with some people that I met. It was a neat experience that I would repeat as often as I could!