I doubt it.
It's 2 completely different and separate worlds colliding in a very uncomfortable way. And that's leaving aside the risk of the girl being blackmailed or outed to her familhy.
What do you mean by 'honest and upfront'?
Is that you want to go tell her something like
"I know you have been moonlighting as an escort
and you know I have the hots for you. Let's talk how
I am going to book a session with you. Can I just
call your personal number? Would you give me
a discount or better if I can get it free? I promise
I won't tell anyone else about your second job."?
absolutely not ! I had this one friend I knew from high school try to book me several times. He told me we knew each other and that it shouldn't matter because he was paying. However it DID matter because the fact was I knew him & I never ever thought that someone from my school would contact me.
The main concern is exactly what @oil&gas said people who know you could possibly use it against you.
My suggestion to the op is if you know the girl from school and shes told you she doesn't want to see/ service you then respect her wishes and leave her be.
this is a question for the SPs in the room:
if someone from your civvy life knew what you did and wanted to book you, should they? would you let them if they were honest and upfront?