A friend does this regularly, with the girls going along with it a few times. The last time was a month ago. We went out clubbing, and got talking to some girls. One of them being a young, unemployed single mum. We started quizzing her about how she feeds her 2 kids, how she could still go clubbing etc etc, and she gave us a sob story. He could have probably got it for free, but to cut a long story short, he offered her cash to help her out, if she went back to his place there and then. She said yes, said goodbye to her friends, and off they went.
Looking back on previous experiences, i'm sure a couple of women i was sleeping with wanted me to suggest this, for us to keep on seeing each other, but as i was already getting what i wanted, i didn't offer it, and they were too ashamed to ask for cash themselves. I was seeing a married EE for a bit, who i later found out was sleeping with half of the town (ugly guys, and she was stunning) for material goods. I also met a young English girl last year, who complained about financial difficulties a fair bit. I didn't clock on, and we soon drifted apart.