That's the answer, right there. A couple of rounds in the sack should easily cover the rent.Assuming it's the type of boy you like, would it not make sense to invite the guy around to earn his money ?
None of my regulars has ever asked me for money. But they tend to be boys who are in high demand so have no need to beg.
However, if one did ask, I'd pay up straight away. No questions asked.
They are my regulars because they are special to me. I've known them for years.
Other boys in the bars may try it on but I simply say I can't support everyone who asks. I'm not a charity.