First time
The first time I actually gone skinny dipping was an accident. It had started out as a day out on the boat with a couple friends. We were inner tubing and having a blast, then came my turn on the tube. Everything was going pretty good until I saw them turn the boat turn towards a pretty big wake off another boat, then I see the boat actually come out of the water in front of me and all I can think is I'm next. From what I was told the tube came about 7 ft out of the water and I was about 5 ft above that, while still forward at a pretty good speed.
I was so disoriented I ended up hitting the water at a weird angle and lost my swim shorts at the same time. I was still looking for them when my friends got back to pick me up, and I told them what happened. We spent the next 5 minutes looking but were unsuccessful, so with nothing else that could be done I climbed back on the boat naked except for my life jacket, I took that off right away and then grabbed my towel. Fortunately it was early in the morning on a weekday so there was hardly anybody there.
Next we were trying to figure out what to do next, they asked if I had a change of clothes in my car, but I didn't, so I just told them I'd be fine with just my towel and we should continue boating for awhile longer, so we did. I even got back on the tube a couple times, eventually we ended up over in a swimming area and we all went skinny dipping.
It ended up being a great day on the lake and we ended up loading up around 5 and heading home, which incidentally happened to be the first time driving naked too
My dad was part owner in a pool business and he had a pool built when I was around 9 or 10. We had a privacy fence and on it he attached a bamboo flag pole. We had about 4 different color flags he would fly. One was neighbors allowed. One was kids allowed with an adult. One was for men only. That's when we would skinny dip. That's the first time I can remember.
My first time (age 12 or 13) was after a hot day of baling hay. By the time I got to the textile beach the weather had changed and it was sprinkling. So there were only 5 or 6 people there. I swam out to the raft and under it. Slipped my shorts off and tied them to the anchor chain. At first I stayed by the raft, eventually I swam around the whole swimming area as my confidence grew. I even got up enough courage to swim within 6 feet of a girl I knew ( in chest deep water) and BS for 15 minuets. What a rush ;-)
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