I have let several naked pictures of me make their way out on the internet. I'm not a public figure and I generally don't have feuds with others at work, etc., so I figure that the chance that they will be seen by someone who will use it against me is close to zero. The upside is that to me, it is a huge turn on to be seen naked, which to me means that both my face and penis are clearly visible.
I have shared pictures with people here by private exchanges, but I don't post face pictures here, because I talk freely in forums about topics that I don't necessarily want people I know to associated with me, particularly regarding casual nudity exhibitionism and openly acknowledging that I have a small penis.