Let's go on a long train ride ;)
Sorry, can't help, but sounds hot.
Let her see them, she may like them. If not, tell her it is just harmless fantasy.
Sounds great, too bad you're so far, Wisconsin here.
Are you a guy or girl? That sounds fun, I am male.
I don't know of any gloryholes, but there is a park west of madison that is supposed to be good for dogging.