I have to agree with others sending pictures with your face while being naked, it is not a good ideea.
On the other hand... my Owner after speaking to so many girls, he offered and asked for us to send cams, in order to confirm the pictures we sent, that we were what we said we were.
Of course it was a normal discussion, dressed both of us. The thing is we knew we wanted a real life thing, so getting to know eachother as real as posible was Very important.
I have has lots of naked pictures here on the site.But i have no naked picture with my face, or any picture of my profile.
So to end this long answer, it depends on what you 2 want,and how much you trust him, but i would still not send pictures like that.

shy