She meets Roman Roy in a hotel room. She already knows who he is, or who his dad is anyway. She doesn't really follow the ins and outs of his family's scandalous lives.
He gets her to sign a non-disclosure agreement on arrival. She's used to that, most of her clients are wealthy, powerful men. She's come a long way from the early days of her work. Once she's signed the NDA, he pours her a drink and sits on a chair that's facing the wrong way around.
"So, Willa. That your real name?"
"Yes," she says, although it isn't.
"You know who I am?"
"Of course." He's not like she expected him to be in person, he seems a little nervous.
"The thing is…" He stands up, pushing the chair aside. "I've never done this before. With a call girl, I mean."
"I prefer escort."
"Whatever. Should we like, kiss or something?"
"You tell me." She smiles. "You're the one who's paying."
"That's right." He seems to grow in confidence at the reminder. "Get on the bed." She does, arranging herself in a seductive pose. He comes over to join her, running his hands down her body and leaning down to kiss her. The kiss quickly intensifies, but when she snakes her hand down his stomach he pulls back.
"Something wrong?"
"No. I just… could we maybe talk for a bit first?"
They end up talking for quite a while, Willa telling him all about some of her past clients, without mentioning any names. She goes into detail about some of her more niche activities. At last he goes into the bathroom and returns looking much more relaxed.
"Well, this has been swell, but I don't think we're really right for each other. You can leave."
"You're sure there's nothing else I can do for you?"
"No, you're good. I've got your number. Maybe we can, like, talk on the phone sometime?"
They do talk on the phone a couple of times in the next few months, but mostly they send messages to each other. He sends her a couple of dick pics with captions like don't forget the NDA! and she sends him some tasteful shots of herself in return. Sometimes it seems like he genuinely just wants to talk. He strikes her as lonely, despite his party boy reputation.
She bumps into him quite by chance one night, in a bar, when she's surrounded by some of the other girls. He's with a group of men, including a taller man who looks a bit out of place, being 20 years older than the rest of them.
"Oh, hey," he greets her. She was expecting him to blank her in public, but he seems genuinely pleased to see her. "How are you?"
"I'm good." She looks at the man at his side.
"This is my brother Connor." Roman gestures at him carelessly. "This is Willa, a hooker I once jerked off to in a hotel bathroom."
Connor laughs like he thinks he's joking. "Nice to meet you, Willa."
"You too."
She gets chatting to Connor while Roman goes to hit on some of her friends. "So what do you do?" Is this the one who went to rehab?
"Well, that's an interesting question. I do a lot of things, but I don't have what you would call a day job, exactly." Willa nods politely. So rich he never had to work a day in his life.
"So you're not in line to take over your dad's company?"
"Oh, no." Connor smiles, which makes him look quite handsome. "I leave that to my brother Kenny." Right, that's the drugs one.
"And what about you? Are you really a…" He's clearly trying to think of the polite word.
"Actually, I'm a playwright," she tells him. "But I do a little escort work on the side, yes."
"Wow. Have I seen any of your plays?"
"They're still in the pre-production stage."
"Well, maybe I could take a look at your work sometime. I might be able to help, with the production side."
"Really?"
"Sure. I have all kinds of connections in theatre."
"That would be great, thank you." She takes out a business card, one of the ones she had made with Playwright below her name in calligraphed letters. "Give me a call sometime."
He takes the card, then hesitates. "You didn't actually sleep with my little brother, did you? Because that would be a little weird…"
"No, no." She shakes her head. "Nothing happened with me and Roman. We're just friends."
He looks reassured. "Great. I'll call you."
She finds herself smiling as she walks away to return to her friends. Roman has disappeared into the crowd. She can feel his brother's eyes on her retreating back.
Clearly, she's been wasting her time with the youngest son. Connor Roy could be the solution that she didn't know she was looking for. She's sure they can reach a mutually beneficial arrangement.