Perhaps

Three years ago:

She held onto the railing as he fucked her ass, penetrating deep as he was wont to do. A tear rolled down her eye, not due to any sadness at being violated this way, but purely from the pain of the penetration. He was a big man, both in penis girth and overall weight, and she was still a lithe teenager, although he had fucked her ass more than once. He liked to finish there as a form of birth control.

He came. She did not. She never did. He collapsed briefly on top of her, crushing her to the bed, as she did her best to squirm out without disturbing him.

"Darling, you are the best," he said, in his downstate accent.

"Thank you, Daddy," said Charlotte, using the term her stepfather insisted he be referred to in the bedroom.

He sighed, and uncharacteristically pointed towards his overalls. "I got two hundred in there. Won big at the boat tonight. I think you've earned it," he smiled his rotten teeth as Charlotte's eyes widened. She never expected that sex could lead to such monetary gain before.

Now:

"Perhaps," she said. "What's the job?"

You frowned. It was a fanciful idea to think that you had some sort of magical control over all women who worked for you. Apparently not.

"Umm... you come work for me. Not just random guys, in sometimes dangerous environments."

Charlotte thought it over. A legitimate position in a legitimate company? Sure, her pay as a high-class escort was earning dividends. She wasn't just trailer trash being paraded out by her stepfather now, she was hustling with the hustlers on the Board of Trade. She knew half the men, and more than a few of the women, on the City Council. She was, in three short years, getting to the top of her game, and one of the most well-sought after call girls in the Second City. Staying with this guy over the weekend, even with his billionaire father, was a step down for her, and she only did it as a favor to said father to make sure he didn't kill himself and cause an embarrassment following his termination.

She estimated her first cool million in about fifteen months, but if she left now, to do whatever he wanted, she would surely not make that goal, maybe ever, and he could crash and burn and she would lose all her clients and the Escort Agency would drop her for being flaky.

But... escort was a rough business, even in the high-end market. There were no shortage of American Psycho-types who want to disfigure her or at least rough her up in other unmanageable ways, and saying "No" to millionaires and billionaires was always a hard prospect for one trying to get ahead in this business. The fear of blacklisting was ever present, even if it was reciprocal. The Escort Agency was too posh to have a bodyguard with her on calls, and this frightened her when meeting clients. A steady stable of routine clients, which she was forming, was healthy but not necessarily conducive to getting the big bucks. This sort of career change could be the best.

"Okay," she said, after a lengthy pause. "I guess being an escort wasn't a life-long commitment. What role did you want me to fill?"

"I want you to be my permanent escort."

Tammy Winthrop exited from the small jet on the private airfield, to be greeted by Mr. O'Shea himself on the tarmac. "Thanks for the ride, Charlie," she said, greeting him with a familiarity he was not accustomed.

"With pleasure, my dear," he said, as the two were escorted into the waiting limousine. The May chill from the lake hit as they entered, and Tammy was glad to be inside. She had spent three weeks in Paris on a fashion shoot for Purple Magazine, and was not used to wearing all these clothes, but they were a godsend in the unseasonable Midwest weather.

"Wine, my dear," said Mr. O'Shea, who's hand was resting on Tammy's leg, but she did not respond to it. She graciously accepted as the lights of the city flew by.

"I've removed your fiancé from his position. Letting him stand on his own two feet for a change. Like my father did, and his father before him. He's doing much better than expected."

"That's good to hear," said Tammy, as the cabin heated up and she removed her fur coat. Charlie began taking off his cufflinks.

"I hear he's forming a company?" Tammy slipped off her pencil skirt, as Charlie unlaced his shoes. The driver rolled up the privacy window, and hit the button that released a small mattress from the trunk, as Tammy and Charlie's legs kicked up.

"Not really. Just a few harlots to keep him occupied and a couple of my low-level clients about to go out of business." The old man was down to his undershirt and boxers, as Tammy released the last of her garments, before embracing her prospective father-in-law.

"That's nice," said Tammy, licking her lips as she slipped down the bed. "I wonder if he's doing what we're doing right now?" she said, with no sign of jealousy, as she fished out your father's cock and engulfed it in her mouth.

Less than three miles away, Stephanie engulfed your cock for the first time. She nearly gagged, before Sophie bent down and guided her to take it slow. "That's it, Steph. Nice and slow."

Stephanie could not respond at the moment, but gave a thumbs up when she picked up the cadence. You held the teenager's head as she gave her first blowjob, and was doing one hell of a job.

"I want to thank you again for hiring my sister," said Sophie as she stood up and looked down proudly. "She'll make a great errand girl and intern. Better than working at that coffee place across town."

Her green uniform was still crumpled on the floor next to the topless form of the 18-year-old. Your maid, Ana, walked in through the open door and simply blinked at witnessing the first sex act you were committing. "Mr. Matrick," she said, "Your fiancée, Miss Tammy, has pulled up."

Now was the moment of truth. "Send her in," you said, to see her reaction to you deep throating this virgin girl who was simply here to visit with her sister.