I doubt he actually pays for the GFE. It's more expensive and he's cheap as fuck. He just expects it because he's "nice." It's remarkable how actually MEAN he is, on top of everything else.
He's too broke at the moment, but he did, at least the one time. It cost him $4 grand -- which was apparently double the normal price; Russell was already known for being a troublesome customer. That was the time when he got the VIP treatment; the brothel sent a limo with the hooker to pick him up from the train station, he wasted all his time taking her to dinner, and then when the clock ran out (he claimed he didn't realize that she was "on the clock" while they had dinner -- what a bamboon), he blew up and expected a pity fuck, at which point, she'd had quite enough of him and wouldn't even let him
buy more time to fuck her. Then he went ree-ing back to the brothel owner (Dennis Hoff) who, in an attempt to keep a happy customer, took half the money away from the hooker and offered to credit Russ for time with 3 other girls, which Russell refused because
that hooker was his girlfriend. He sued her; Dennis Hoff didn't show up to testify against her (I know, I'm as shocked as you are), and Russell lost,
and got a restraining order filed on him by the hooker.
That ended up being long story long, but the details are too good to leave out. There's more, too, because that's the beginning of the long, sad story that ultimately resulted in him getting banned from Dennis's brothels.
Russ has this fantasy of the hooker legitimately falling in love with him.
This, exactly. I'm honestly not sure whether he thought his time would be well-invested and he'd be rewarded with free sex for life, or whether he legitimately thought the clock didn't start until they got to the bedroom -- although with as trustworthy as he is known to be, I'm inclined to doubt his side of the story. Either way her refusal to bed him came as a horrible shock and led to an epic meltdown.
I think he full well knew that
normally the clock starts immediately, but he thought that he was so damn special that once she met him in person and had too much
fun on their date to truly call it "working", she'd fall head over heels in love and give it to him for free.