First Time BustedBeen skinny dipping many times. Sometimes solo, sometimes with the wife. Sometimes on a dare (hotel pool).
But my very first time skinny dipping was when I was young, and happened to get caught the first time I tried it.
So my buddy and I were allowed to stay home at his house for the first time (ever) when he was 12. We weren't allowed near the pool without a parent, but being mischievous boys we waited for his mom to leave and then hopped over the fence to take a swim (it was 100 degrees outside).
The thought process of a youth is hilarious... We thought if we went swimming with our clothes on, there'd be wet clothes as evidence. We thought of going in with our underwear on, and then throwing the wet underwear away afterwards, but she might notice wet underwear in the trash or even realize a pair of his was missing. We thought about putting our clothes in the dryer afterwards, but we didnt' know how long she'd be gone so there might not have been time for that. So we decided we'd go naked (with rules). The rules were these: we couldn't be on the same side of the pool at the same time. If one person was getting in, or out, the other had to turn away until the person said it was safe to look. We are both straight and were very concerned the other would think differently!
We had only swam for about 10 minutes when his mom came outside. She was NOT happy about seeing us in the pool and told us to get out immediately. I was in the shallow end, but covered my stuff with my hands. I guess she saw our clothes on the lounge chairs, and our lack of "getting out immediately", (or me in the shallow end) and realized what was going on. So she then told her son to meet her inside the house in 5 minutes. She turned and went inside, giving us our privacy. I grabbed my clothes and pulled them into the water and put them on while still in the pool. I let myself out his back gate and walked home wet.
He got a lecture from his mom on obedience and an awkward talk about how 'curiosity is OK'. LOL