A man in his mid to late 20s is struggling to become a published author. Then one day he comes up with a new idea. It's partially inspired by his personal life.
That idea is to contact a prostitute not for sex but to talk. He wants to get in the mind set of someone who's never had sex or even talked to a prostitute. He wants to know what it's like to talk to someone like that but in his story the person would actually be considering having sex with her. He makes contact and let's them know his intentions, which they don't believe. He goes to the meeting expecting to have to pay.
At the meeting both the prostitute and him are surprised. They know each other. Or rather knew each other. They were classmates in middle school to early high school.although it takes them a while to make the connection. She had actually been the first girl he ever had a crush on.
He's surprised to find out that she was fairly new to this profession. She's given a few blowjobs, hand jobs, and even done anal a couple times. But has never experienced vaginal intercourse. Her boss or should I say Dad makes sure of that.
Through their interactions he changes his story idea and has the character nervous about interacting with his long lost crush. And their blossoming friendship.
And he may in fact sleep with her. If he does he looses contact with her for a bit and when they meet again she's in a good family friendly job and she has had his child.