I know what you mean. That happened to me A LOT when I first started doing phone sex (and still now with ps and cam) I had to train myself to become a "master" of picking up on the slightest of clues and reading between the lines to figure out what some of these people want when they enjoy playing the vague game.
When I have guys who say "Oh wanna see me finger my ass?" I know they want to show off, so I say yeah and fake shock then tell them something like "OMG! Wow I can't believe your fingers slide right on in there like that! How many can you fit? You ever use a dildo? What about a real dick? Show me what all your hole can fit inside of it!"
Reminds me, I had one guy on ImLive earlier say "Hi ma'am. What should I do with this?" and he held up what looked like shit on a plate (dog or human I'm not sure which). Obviously he wanted me to instruct him to eat it, but thank the lord above my mic didn't work for some reason and he disconnected the session before I vomited all over my desk!

