Been chatting with a SB for a month. We chat about everything except the allowance. Met a couple of times, went to the movies, felt each other up and made out. Still no mention of money. Should I bring it up?  
She been on dating sites and unhappy with the guys on there. She also met a few "terrible guys" on SA.
I am fine giving her the allowance, but I am apprehensive "she'll feel like a prostitute" if I offered. Don't want to spoil a good thing.  
Just go with the flow or ask her about monetary expectations?

My advice is to be VERY careful with your phrasing, but unless you want to run the very real risk that she starts thinking you are just cheap and she leaves you for a guy who gives her money, I think it is a conversation that you need to have.

 

Obviously you don't want to make her "feel like a prostitute" but you need to find out if she really needs money, but is too shy to actually come out and ask you. Something like, "I know we have never talked about this before, but I know we did meet on a "sugar" site, is money at least part of the reason you joined that site?" Depending on her answer you have a segue to find out if she is struggling financially without making her feel like a hooker.

Something along the lines of she has a bunch of bills to pay and no idea how she's going to do it.   You can then be Mr. Nice-guy and offer something to help.

 
For you to bring it up could lead to her being uneasy about it.

 
Trust me, she's going to find a way to broach the subject.

Before we go bcd, I always say something like: “ I would like to reimburse you for your time.”  The one time that I didn’t get an understanding before we went bcd was similar to what you describe. We met for dinner, afterwards we made out but it was late and she had to get up early the next day. When we went bcd the next time we met, she wanted $800! I got her down to less than half of that but that’s the last time we met.  

Hookers get paid ostensibly for "their time" SB's do not.  If she is a pro or a semi pro don't worry, she is most definitely going to broach the subject long before you get naked, or right before if she is trying to really get you when you are at your weakest.

 
Non pro SB's are often shy about asking for money, partly because they don't want to think about themselves as hookers, and partly because they have been led to believe that SD's are going to shower them with cash/gifts without them ever asking. What happens sometimes is that they will actually have sex with you, not because they are so enamored by your charm, but because as non hookers they simply don't know how to ask without feeling like a prostitute. What happens next is they feel taken advantage of and then they ghost on you.

 
Now "sometimes" during dinner/drinks or whatever you do on your first date they will allude to the fact they the "last guy" tried to buy her and how turned off they were by being treated like a prostitute, THAT of course is your cue to NOT bring up money, but in most cases at some point you want to reassure her that you know that "sugar" is part of the equation.  I think one of the best ways to get "her best" out of her is to kind of make your first BCD experience with her sort of like an "audition" where she gets to do her best to impress you, with the "implied" understanding that they happier you are with her, the more generous you are likely to be.

I have had two SB relationships over the years where we went months before talking about money.  The first one cut me off (my fault for taking advantage) after 1 month.  FWIW we consummated the relationship on the first date.   After discussing the reason (which we both knew) agreed on a monthly allowance that I paid once and never again and we stayed together for 6 months.  The second SB wanted an experience and I never paid nor discussed an allowance.  We were on and off for a year before she got together with an old SD who is now her fiance.  Due to distance and her kids the timing wasn't right for us or I might be married again... UGH!!!!

I never use terms that frame allowance like payment. "Pay for their time", "per session", or any "quid pro quo" type of phrase are all just reinforcing the hooker paradigm.  What I would do in your situation is ask her of she's ready to "stay the night" or "take the next step" or just say you really want to make her happy. She may reply with an ask for sugar then, so negotiate and off you go.  
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If she accepts and still doesn't mention anything, just slip an envelope with $$$ in into her purse/coat pocket before she leaves. If she sees you doing it, say something like "here's a present for you", or "thought you could use some help with your bills", etc.  
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Either way, if she seems shy about asking or might be worried about "looking like a hooker", down play the cash and focus on how much you enjoy seeing and pleasing her.

One of my very least favorite things is to get all excited about a new SB only to find out at the very last minute that her expectation$ are way out of line, from my point of view.  I know some of you experienced mongers swear you never discuss money in advance and even get girls to sleep with you for free.  Never works for me.  Just recently I figured I would try that method one more time.  Had a wonderful message exchange with a young one, met her for coffee and had a great rapport,  agreed to meet BCD the next week and on the morning of the day in question she finally texted me and asked for more than twice as much $$ as I ever pay, claiming her last men paid her that much.  I was so disappointed, but I gently said no and moved on.  So I really like it when the SB asks about $$ early on, and if she doesn't then I will make sure I bring up the subject.  I don't find they are shy about discussing money, and of course, I'm careful not to make it sound like sex work, even though we know it is.

Although it got me kicked off SA, I found that delaying money talk always resulted in disappointment. Set their expectations early.

If she doesn’t bring it up, don’t ask her about it directly. Ask what she needs money for. Then say you’ll help her with that to make it your amount. If it’s rent, or something huge, say you can help over the course of a week or a month, etc.  This sets the tone for no cash visits if the sex is good for her.  

If she bangs you without mentioning sugar, just leave her a present before you say goodbye. More if she’s worth it and you don’t want her to get snatched up, less if you could care less about repeating.

I did bring it up and I am still confused. We spoke of dating sites and I reminded her that sa was about an allowance too. She was embarrassed and joking her friends will think she’s a prostitute.  
I too laughed it away. But still no number. Then I asked if she was doing ok financially and she said she was for now. She said she’d think about it.  
Nothing about the allowance for more than 24 hours. Meanwhile we are chatting about all sorts of things, including sex and what we like.  
Now I am totally confused

You got a freebie. Run with it.

Sounds like you are communicating pretty well, just keep listening.

hope so. Don't want to lose this one

Yes I agree "paying for her time" is clearly a term escorts you for legal reasons. I would not use that.

Here is a suggestion, throw a couple of hundred bucks in an envelope with her name on it every time you see her. Let her know that if she ever needs some help that you will be there for her and simply hang on to "her money" for her until she needs it. If she never needs it, wait until you've put away a few grand "in her name" and go do something special for or with her like a nice trip or something. In the meantime don't stress over it.

Good advice as always GaG

tell her you wanted to buy her a gift but did not have the time or did not know what she would like.