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Chapter 3
by
Mr_anderson
What's next?
Hailee Steinfeld (prostitution)
"You're a bit too well-dressed to play the whore, Hailee, and a bit more flashy makeup would be more interesting..."
"Listen, James, if you want to role-play whore and john, at least, let me be a high-end escort."

James sighed, that's not what he wanted. But that's probably the best he could get for his kink, so he gave her some bills, and she put it in her handbag.
"Ok, James, what do you want to do?" She asked.
"You're not supposed... Forget it. Undress yourself in a sexy way."
Hailee started to undress while moving sensually.
The experience, was a bit of a deception for James, but to his surprise, Hailee came into the bedroom dressed in a small top and mini-skirt.
"You called for a girl, sir?" She said.
She was better in her role, and it seemed that she had some fun acting like she didn't know him. At first, James thought that Hailee noticed he didn't enjoy enough their first try. But, she did it again a few days later, looking even more like a street hooker, with makeup and all.
Then, James got a call from Hailee, asking him to come to a street close, late in the evening. He found her, dressed like a slut, with colorful cheap makeup.
"Hi, sir, wanna have a good time for a few bucks?"

It was a dream come true, the place, the look, the talk, she was a whore and he was going to be a client.
"Sure! What don't we take a room?"
"Sure, whatever ya want."
She followed him in the hotel and the receptionist gave him a look like he judged him from bringing a professional to the hotel. But maybe it was in his head. Hailee will tell him later that she began to enjoy too playing the whore and that it was making her wet to think that he was paying her to fuck her. But, while she was in the role, they were thinking of themselves as whore and john.
What's next?
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Short stories and other tales
Sometimes short is good too
A compendium of stories inspired by pictures or just ideas on the go.
Updated on Mar 31, 2026
by Mr_anderson
Created on Jun 3, 2023
by Mr_anderson
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