Everybody knows there's nothing worse than erotic with bad anatomy, so how does one understands that "it's time"? I want to try to start drawing NSFW eventually, but I ain't confident in my anatomy skills yet, and I don't want to make people's eyes bleed.
Besides showing people art and asking if it's any good, of course. Not only there's very few people I can nag with that kind of question and expect an expert answer, but I also really don't want anybody knowing that I'm drawing "this kind of stuff", especially my friends, (too many social risks), so if I'll draw anything, it will be posted from a fake account with no ties to my person (and with constant paranoia that I'll accidentally mess something up and people will be able to connect the dots, lol).