I think there might be. I remember looking at the Converse-Fetish.com samples and sneaker-planet samples and there were some shemale things going on that involved Chucks.
Don't know of any directly - at least yet - will keep a look-out for you.
This actually is "the best place" for sneaker and sex action. Seeker does have some "she-male" sets in the converse and keds sections. Not particularly "hard-core" but good shots.
There is some good hard-core girl/girl or guy/girl.