Just a quickie first

When Jason gets back to his desk, he finds Kaylee laying on her desk. Her leg is over a young man's shoulder, high heels pointing straight up. He's plowing into her, sweating profusely. She hasn't bothered to get all the way undressed, probably because she would have to get undressed and redressed far too often. "Hey boss, your one o'clock is here," she says. She's clearly trying to **** a neutral smile, but she can't keep control over her expression. She gives up and lets her head roll back, holding her breath. "Oh FUCK!" she shouts in release.

Jason has a hard time looking away from his assistant, but he checks out his next appointment. James Statler is a fairly young man, about college age. He's been a client for a while, being a trust fund kid. His dad started him off early, using meetings with Jason to try to learn about investment and long term planning. James took to it well and has always been a model client. "Hey James, did your dad come with you today?" he asks.

James looks up from the writhing assistant but doesn't stop. "Uh, hi Jason. Yeah he's in the, um, car. Is this okay?" He looks between Jason and Kaylee.

"I can't control her. She does what she wants." Jason shakes his head sadly. "At this point, Kaylee, I think people think of you as a treat or coming to the office. Like a lolipop at a doctor's office. I mean, except that I'm sure people make these appointments just so they can have some time with you, right?"

She nods, trying to speak but not able to. She mouthes the word "harder" to James.

"Obviously your dad has been with her a few times. But don't you and your dad share your famous supermodel step-mom too?" he throws in on a whim.

James' eyes shoot wide. "You can't know that. You can't tell anyone or her career is ruined." His thrusting doesn't stop. Kaylee squeezes her eyes shut, her legs shaking, orgasm rocking her body.

"Don't worry, I won't," he says, smiling kindly. "Your business is your business. Now, I'll give you a moment to finish up." He checks his watch. "Though your dad will probably want a turn too. I'll head into my office and you can come in whenever you're ready."

"Ha! He's gonna go jerk off. Look at him trembling," Kaylee says, her orgasm over. "He's so pathetic he likes watching you fill in where he can't."

Jason scowls at her and goes into his office. He isn't going to jerk off, but that's mostly because of what Yasmine did in the break room. He's lucky he's wearing dark pants or the spot would show. "Do I have a fresh pair of underwear?" he asks, pulling one out from a drawer. Behind his desk, seated, he changes. Outside an older fat man joins he fucking duo. He sits in Kaylee's chair, and Kaylee turns over to blow him while James keeps going from the back. The old man finishes first and gives Kaylee a kiss on the top of her head, like a doting parent.

The meeting goes fine.

On the drive home Jason thinks about Kaylee. He really does like the girl. She's an incredible employee and has been a good friend. She's in school and has a promising career. All of these are things he's actively ruining for her. Which, he decides, is okay. It's fun, it's sexy, it's hot, and she's having a damn good time too. He just needs to do something to fix the holes he's leaving in her life.He's stopped at a stop light, considering his options. He sees a man in a nice suit walking down the street, a young woman walking in the same direction, probably unrelated. "Is she the secretary that he's having a secret affair with? Do they both think he's going to leave his wife that barely has sex with him for her? When he tries to leave her, is he going to find out that his wife is just bored in the bedroom because she's really kinky and wants a throuple with the secretary?" He asks these questions absentmindedly, working through alternatives. That one wouldn't work for them, because he's already doing something fun with Willow, and he doesn't want to be a participant in any of their fun sex.

The light turns green and he starts driving. In another car he sees a young man driving alone. "Is that man the heir to a vast fortune and uses his natural charm, good looks, and money to start a harem of sexy strippers and porn stars?" He thinks about James from earlier. That might be fun, but he wants Kaylee to keep being his slutty assistant. He doesn't really want her to be property anyway.

Getting into his own game, he spots an older woman. Very severe, like a school teacher, with shorter curly hair piled on top of her head like she sleeps in rollers every night. "Is she the matriarch to a family of extremely sexually active, kinky people that she incestuously dominates? Does she have a rebellious granddaughter that she'll have to bring back into line by forcing her to go through humiliating, public sexual encounters?" The woman's clothes switch and become fairly revealing. He grimaces at her wrinkly old flesh on display and says, "has she physically aged very slowly since her early 40s, when she was hot enough to be considered a MILF?" Okay, that one got away from him. But he does consider Kaylee's family. Maybe there's something there he can do. But there's still the matter of her career. He can decide more later, but she's going to need a way for her to make money.

A/N: Okay, everybody, what does he want to do with Kaylee! Does he:

1. Have her find a very rich man to be her sugar daddy (more focus on an individual)
2. Change her family to the point that she doesn't have to work except that she enjoys it (****, likely bringing in more characters in her family)
3. Have her start down the path of porn, camming, stripping, etc. (The path of fame. She might collaborate with others)
4. Have her down the path of fame via something like acting, or maybe cosplay. If cosplay, I'll probably need to pick a new model for her. (Also a path of fame. You should know, I'm really not into celebs in stories, don't pick this because you want her to fuck Scarlet Johansen or whoever. However, this will probably lead to stuff like her fucking on live TV or fucking her fans or something.)
5. Keep her in the same financial field, but have her mooch off of Jason and his family (I guess this would include financial domination. Also kind of an adoption route, come to think of it. That could be formalized too if y'all wanted.)