Although this really wasn't "skinny dipping', it was close and an interesting experience.
Few years ago I went with a group of friends to a major NHRA car race. It's a several day event and we stayed at a motel....this particular motel was a favorite spot of a group of guys (mostly family) whenever they went to the race. Found out later, amoung the reasons they liked it was because they had a pool and a big hot tub.
Now, all of these friends were black, except for me. Sharing a room were two black guys that were identical twins, their sons and their adult cousin. I shared a room with my friend James and his brother.
First afternoon we were there, after unpacking and relaxing a bit, one of the 'twins' came over and told us they were all going to the hot tub. He was wearing some swim trunks. James and I told them we didn't bring anything like swim trunks. Interestingly, he suggested we wear some boxers! Now, the hot tub was in a public area of the hotel, a distance away from our rooms. I was NOT going to walk all over the hotel in boxer shorts!
We did bring some regular shorts with us even though the weather was still coolish. I wore some shorts with briefs underneath. My buddy James never wears underwear, so he just wore some shorts. Anyway, on the way to the hot tub, my friend's shorts kept slipping down revealing more and more of his ass!
When we got to the tub, the twins and their sons were already in it. It was NOT that big. I got in and then my friend James 'belly-flopped' in, spashing out a lot of the water. We were in there for a while and a nice looking 'white' chick was standing around in a tank-top waiting for us to get out. Eventually she asked if we were "ever going to get out of the tub?' Of course a couple of us asked her to join in!!