This rather intriguing artwork is by the artist Waldemar-Kazak. It’s called ‘Talking over a bear’ and you can see the original full size version over on his Deviant Art page. I’m not exactly sure what the story is behind it. There’s a very 50’s feel to it, an edge of melancholy created by his expression and a weird sexy vibe (at least in my strange brain). It looks like it should be an illustration for a twisted short story in something like the New Yorker.
I originally came across this in the Femdomarts tumblr.