We were once rookies too, and DSR was our very first visit to a nude resort. We (I) chose DSR due to it's nude policy, I wanted my wife and I to be in the same boat as everyone else there. I thought it'd be uncomfortable to have our first attempt at the nude thing with people around us in varying states of dress rather than everybody nude. I'm sure we would have opted to stay somewhat clothed rather than jump in with both feet.

We now visit DSR at least twice a year and wish it was more often.

To your question, if you emerge from the pools and lay on a lounger to dry off and opt to throw a towel over yourself you'll be perfectly fine. If you emerge from the pool and put on some shorts and a tank top and plop on a lounger you may have a nice employee ask you to move off the pool deck. The DSR people are not vigilant, but they do try to apply the rules to all guests fairly.

Like Carol, I think after about an hour you'll wonder why you even cared and enjoy the beautiful grounds, sunshine, pools, freedom without a concern.