My 'cycle' is almost always the same ... see the same WG two or three times ... ask for (and usually get) a discount, due to being a relatively undemanding punter that they know is going to be easy money even at discounted rate ... quickly get bored and move on to a new WG. I think it's my undemanding nature that is probably the key to my success in this, rather than amazing looks or personality haha ... a WG soon knows with me that even an hour or two booking will feature only one pop and most of the time just chatting and hanging out, I'd assume if you're a non-stop sex, multiple pops kind of guy then fair play to you but your success rate at getting discounts might be less.
As far as I'm concerned, you should be asking for a discount after your 2nd or 3rd trip, unless they are so amazing that you don't dare lose the option of seeing them by 'offending' them or know they have no need to drop prices due to high demand. Most WGs are sane enough to take less money in exchange for knowing they're going to get a reliable, safe, nice punter through the door rather than a bit more for a potential loose cannon. Those that don't, move on ... there are thousands of others out there.