There is a series of vids from way back taken at a circus. The technical quality sucks and none of them are what you expect. For example, the vid titled "Woman has sex with elephant" consists of a woman on her back in a circus ring masturbating with a piece of fruit. A female elephant walks up, snatches the fruit out of her snatch, and eats it. It should have been titled "Woman has sex, with Elephant."
The most that ever happened in several vids with a female Chimp is that the Chimp stuck a finger in the woman's cunt and then licked the finger.