Always find a way to ask.
Ask if she is prepago and possibly offend a good girl.
-OR-.
Do not ask a bad girl and possibly get your ass kicked by her BF, cousins, etc. Have unhappy scene at the hotel lobby. Go to jail. Not a a difficult decision.
Good indications are number of body piercings, location of piercings, how many tattoos, location of tattoos. The taller the high heels the higher the chance she is for sale. And the list goes on.
Ask her specific questions about her job. The more questions you ask and the more detailed the questions the easier it is to see she really does not do that job. Ask 3-5 questions being more and more specific and the game is up. Or odd questions. If she is a chef then ask her the temperature that fish is considered cooked. What is her favorite spice and why. What meals does she use that spice in. Then ask her to cook it for you and see her speech stop or her face drop. It can be very fun after some practice. See how fast you can steer the conversation to back her into a corner.
If you want to ask if she is prepago without offending her then tell her you once met a girl early one day at the mall. You took her to lunch and hung out shopping. When you went to leave the mall she ask for money. You were confused and she explained she was an escort and gets paid for her time. You did not expect that and do not want future problems with anyone.
In your scenario, of offering money in the morning and she is offended. There are many ways to save face for both of you. Just say you wanted to take her shopping but do not have time today because you are meeting a buddy.
"Here. Take the money. Do some shopping and take a few of your friends to lunch. Maybe we can meet up tomorrow or tonight".
"What? Last night I thought you said you had to go shopping today for someone's birthday. Sorry I am not shopping material so I am letting you go alone. Is it too much?
"I thought you were going to go out to bring me breakfast in bed? No? Bad girl. Hahaha. ".
"Sorry. Just a reflex. My ex-wife used to wake me up in the morning asking me for shopping money. Since you were so loving like my ex-wife it was just like deja vu. ".
So very simple.
[QUOTE=MrEnternational;2308767]And what if it so happens that the girl is not a hooker? I have picked up chicks before that have stayed with me. The next day I have tried to give them money and they have looked at me like I was crazy and asked what is this for.
I would really feel like an ass if I was to ask a girl beforehand how much and it turns out she was not a hooker. That is why I do not bring up money unless they do.[/QUOTE]