John Roberts sat in his truck outside the diner/coffee shop. He was waiting on his first real prospect. This was an idea months in the making, and he was a combination of confidence and nervousness, mostly the latter. The clock showed he was still a few minutes early, and it gave him time to reflect on how he got here.

It all started when he became the “luckiest sum-bitch in the room,” by winning the Powerball lottery. It was very unlike John to play, which made the win even more improbable. After Uncle Sam (taxes) got his part, he was still left with more than $600 million. It was just a crazy amount, and what happened next really spoke poorly of people around him.

First, his ex-wife whom he had divorced for cheating on him with his then-best friend tried (unsuccessfully) to claim part of it, even though the divorce had been final for a year. Next, it was family him never knew him had expecting a handout, then friends asking for a handout. It was just too much. His lawyer suggested John form a ‘blind’ corporation and change his name, which he promptly did. John also bought a home in a gated community thru his company, and proceeded to simply hide for a time.

During this time, John was not idle. He setup a very nice weight lifting room, and hired a personal trainer, followed by a nutritionist. John even paid them extra to come to his home to both educate him in his diet and for training, and most importantly to also not ask questions. Not only that, John underwent the knife, and changed his looks. The idea was never to be an Adonis, but rather to simply blend in. After 18 months, he doubted his ex or his own family would recognize him.

John next took half the winnings and invested them with a firm in nice, safe, investments. John took a small chunk of the remaining, and bought a gorgeous beach home right on the Gulf, after selling the other home in which he had originally hid. He also purchased an extremely nice, new truck. Though he kept the old one so as not to draw attention. Taking what amounted to about a quarter of his remaining winnings, John hired another firm to make much riskier trades. One of those was crypto-currency and the upshot was that John had nearly his lottery winnings all over again!

As you might imagine, during this theme John was nothing if not lonely. Yes, he considered prostitutes, ‘sugar daddy’ sites, and the like, but after his interactions with the general public, he was more than a bit gun-shy. So it was that one day John found himself watching porn, and the idea was born. He was watching one those channels wherein a woman supposedly answers an ad for modeling or the like, and is convinced to do porn. Of course, it’s all ***********ed and totally fake, but it did plant a seed. Were there not ***********ed whores, but rather actual women in dire need of cash, and if so, could they be convinced to spend a few days with him, enjoying their bodies?

The more John thought about it, the more he liked it. He paid a visit to the realtor that sold him the beach house, and he helped him find a nice apartment in the state capitol, about an hour plus away. John was in a good neighborhood, just a bit upscale, without being too pretentious. From there John took a look around, and began to conduct his search. He had a plan. What he needed to find the right lady or ladies, like single mothers or college students with lots of debt. Basically, women that were desperate for a way out.

John spent several weeks going any place he could think of to find a match. Finally, it paid off when John was in a small, family owned roadside restaurant on the outskirts of the city. He had been out every day this week and was about to give up hope. John was finishing his meal when he overheard two women talking in the back about how the tips here were horrible. One of the two girls said that she had to come up with at least a grand to pay for her car, plus she was already behind on her rent and the landlord was threatening to kick her out if she didn’t pay.

This was the opportunity John had hunted so hard for, and it was so close. And better yet, the girl with the money woes was his waitress! Actually it would be more correct to refer to her as a lady. Her name tag said ‘Kaitlyn’. John knew she must be at least 21, as the place served alcohol. She was a stunner, brunette hair, and a wide smile with an amazing body with D cup breasts, a nice ass, dazzling eyes and a nice smile.

John looked at her for a moment and answered, “No, I’m am good, thank you. The food was delicious, and your service was great.” The girl smiled, pulled out his bill and said, “he’ll be you cashier when you’re ready.”

John nodded and she walked away. The bill was only $20. He had already planned a way to get her alone to talk to her. John took a pen and wrote down his phone number on a hundred-dollar bill and wrote, “Call me.” John put the $120 dollars down and walked out quickly. Now, he had to wait for her to call, if she would call. If not, he hoped he could come back tomorrow and not appear creepy.

John was at the apartment, questioning the whole idea, when his phone started ringing. He took a deep breath and relaxed his nerves. Picking up his phone, he heard Kaitlyn’s voice, “Hi.” He answered, “Hello.” The girl on the other end sound nervous. “This is Kaitlyn, from the restaurant. The one you give the big tip to. He wanted to call and say thank you for that.”

John knew he had her. Otherwise, there was no was way she would call him. He asked Kaitlyn if she was free right now and if he could meet her for some coffee at the local coffee house that was open. He wanted to talk to her about something. Kaitlyn thought for a minute. She didn’t want to meet him alone but she would be safe at a public place with people around here if he was a creep. Kaitlyn agreed and John said he will be waiting there for her.

And that brought us to this moment. John snapped out of his daze when he saw Kaitlyn pull into the parking lot in a car that appeared to be on its last legs. He didn’t know how much it would take to get her to agree to what he wanted. So, he had ample cash with him in several envelopes. Being tall and muscular, he felt rather safe, despite having all this cash on hand. And unlike the video, that was a onetime thing, he wanted someone long term for the moment until he could get more girls.

John stepped out and met her beside his truck, and he and Kaitlyn went in and had a seat. Kaitlyn sat down in the seat across from him. She was of course nervous, but was reassured that they were in a large public place. Also, he at least did not seem to be a creep, so her plight had brought her here, and she could at least hear what he had to say. “So why did you leave him such a huge tip? And what did you want to talk about?”

John looked at Kaitlyn and asked, “So you want some coffee?”

“No, thank you.”

“Ok, he will come clean with you. He overheard your conversation with your friend today, at the restaurant and wanted to help you out.”

Kaitlyn stared at John. No one ever helps anyone out for free. “What do you want from me?”

“You are right, in a sense. But how really it all depends on you. Humor me for a moment and tell me, to ‘set the table straight,’ as it were, how much do you really need?”.

Kaitlyn calculated everything she was late on – paying her rent, car payment & bills, not to mention the pawnshop, and then have some left over for food. She wasn’t surprised by the question, but she marveled that she was actually considering it

John saw her thinking about everything “So how much to get you all caught up on everything and have a little left for you?”

Kaitlyn looked up, then down, thinking about the figure in her head. She took a deep breath and looked at John. “$2500 to pay off everything, she finally spat out” to earn that much.

John looked at Kaitlyn sitting there, and let her response hang in the air for a moment. He knew he almost had her, just a little push and she was going to be his. Glancing around, he reached into his pocket and pulled out an envelope containing $3000 in hundreds. He counted out $1000 dollars and put it in front of Kaitlyn. John knew that peoplee were greedy. If you pull $1000 and only give $100, they will do anything to get the rest of it. Kaitlyn was no different.

Kaitlyn sat and stared, partly mesmerized. She couldn’t believe what she had just witnessed, but also could not see any other way out. He had just handed her nearly half what she asked for, and it was apparent he had a lot more. She found herself transfixed.

“No, I’m not a drug dealer or in the mafia,” he answered with a smile.

Kaitlyn knew if she could set the tables right, as per this man, she wouldn’t have to pawn her items only to go to sleep hungry anymore. Her upbringing had been very hard, and for the first time, she was seeing a large amount of cash, there for the taking. She picked up the $1000 and held it tight in her hand and looked around quickly.

John saw the nervous look on Kaitlyn’s face after she picked up the money and quickly put it under the table. He asked her if it would be OK to go to his truck, ironically right outside their window, and talk in private. She would stay on her side, nothing odd, just talk, and for that he would pay her $100. She nodded. He paid her tab, and held the door for her on the way out. After they walked the short distance to John’s car, Kaitlyn was impressed with it. She’d never been in such a luxurious vehicle before. Again he held the door, and handed her $100 before going to his side and getting in. Now, with more privacy, he could finally talk to her without anyone overhearing them.

Kaitlyn feeling safer in the car. She started counting the money she had in her hand, $1100 total, and looked at John. “What do I have to do for this?” she asked.

“What are you willing to do for it is the question,” John said. His plan was working perfectly.

He counted out and put down another $500 next to her, which she quickly picked up.

Kaitlyn looked at the money and then to John, “stop playing games with me and tell me straight.

What do you want?”

“Look, I just got out of a messy divorce, & I hate going out to bars and clubs. So, seeing as how you need money and I need some company, let’s make a deal. How much will you need for the next three weeks, for anything I want?”

Kaitlyn looked at the money in her hand and back at John. “John, I am not a prostitute you can give money to for sex.”

John responded “I know a prostitute would only ask for $100 or $200. You have $1600 in your hand. So how much will it take?”

John put another $400 next to Kaitlyn and she quickly picked it up to. “So what do you say?”

“John don’t think John can do it for this much.”

“OK, tell you what. Earlier you said $2500, and you’re almost there. How about I offer $3000? You could be out of all debt and have money left over for just three weeks of your time. You’ll never beat that offer.”

Kaitlyn looked at the money in disbelief. She never had this much money in her hand before in her life. It was the key her getting back on her feet. “I….I…I don’t know. He’ll feel cheap and won’t be able to look at myself in the mirror if I do this.” she said.

John knew she was trying to get more money out of him.