I’m not an artist but an erotica author, and I’ve had some deliciously weird commissions over the years (some of which I’ve taken, others I haven’t):

* One guy who wrote me a very lovely and extremely polite email asking if I’d write him a story about a dude being sounded by a Hot Wheels car. (If you don’t know what sounding is, you’re probably better off not knowing.) He wanted the first half of the story to be about his dickhole expanding as it engulfed the little car, which is… fine, but not really in my creative wheelhouse, but the second half of the story was supposed to be about the tiny little wingmirrors absolutely *shredding* his urethra. That’s when I bailed.
* One guy asked if I took photo prompts, and then just sent me a photo of a chair. I had to clarify to see if he really wanted me to write a story about some dude fucking a chair, or if it was supposed to be some sort of Invisible Woman fetish, or if there was something in it I’d missed. Nope. It was just a chair. (It turned out that he’d read my other stuff and just wanted to see what I’d come up with, which was nice; I wrote a pretty little Dom/sub scene about a woman bending over a chair to get a spanking.)
* I don’t do furry work, generally, but I had someone ask me to write them a handjob scene with someone being jerked off by the talons of an anthropomorphic eagle. I pointed out that that would technically be a footjob scene, and he never replied to me, I assume because while he was fine with the concept of masturbating to a half-woman-half-eagle, the discovery that he might actually have a foot fetish was just *one step too far*.