Chapter 1 - Introductions
"She was like a gift from heaven - just what I needed."
John Sheffield was a lonely man.
I was in his early 60s, tall, with all his hair and in good shape, for his age. Strong arms and large, with a little paunch around the waist, like many men his age. His hair was starting to go a little gray, as was his mustache which he wore down the sides, a cross between 'fu-manchu' and cowboy style. He was also very well off, having started a number of tech startups in the early 90s. After being so active and busy all his life, he could not just sit back, play too much golf, drink bourbon and do whatever he wanted, so he kept himself busy managing his investments, dealing with people who wanted his money for investments (as well as his advice) and looking at new technologies just coming up. He kept busy.
Mostly, he stayed at his house, estate actually, in the northwest suburbs of Chicago. He lived among the 'old rich' small communities and his land was fenced and guarded by technology, many of which he had, himself, invented. He was safe and secured, living his life as he pleased, fairly contented and serine. His house was large, but not huge like many of his neighbors. He had 10 acres of land, surrounded by a nice stone fence and with a security gate.
There was the main house, built during the 1920s, three stories with a full, partially finished basement. 4 bedrooms, each with their own bathroom. There was also an open attic area which was finished, but decorated as an old, wooden walled office. This was John's main room, containing his office needs and a conference area.
There was a separate 3 car garage and a 4 suite coach house at the rear. There was also a nice swimming pool in the yard, partially made for lap swimming and partially designed as a grotto area, for more intimate interactions. The grotto also had a large hot tub and cabanas with showers. There was also a cottage at the front gate that was occupied by his security man / body guard / driver, Sasha, and his young wife, Katia. He was a former Bulgarian assassin who had gone straight and was taken in by John. It was a good dear, all the way around.
He had pretty much everything he wanted, but he had no family. He had never taken the time to get married or have children, he was much too busy and focused. So, he lived alone in his house, interrupted only a bi-weekly house cleaning crew and a part time maintenance guy who gut the grass, plowed the snow and did all the other around-the-house chores.
Truly, he had everything he could want.
But he was lonely.
He had spent so much time working that he had no real social life. Sure, he knew others and interacted with them, but there had been no room for any romantic relationships. It would have not have been fair to a wife. After a while he had found that he no longer interested in ever getting married.
But, a man has needs.
He had dealt with his male needs by the occasional hiring of high class prostitute. As the years passed by and he was at home more of the time, he had looked for young women who desired to have a 'sugar daddy'. These women, really girls most of them, were clean and nice girls who wanted to be supported, financially, while they attended school or were working on advancing their careers. Many times, they were also looking for a place to stay. John had invited some of them to live in the coach house suits, sometimes all four suites were occupied. He always found it interesting to use some of his "technology" (each suite, and the rest of the estate grounds was extensively covered with monitoring, audio, visual and even infrared imaging). He especially enjoyed the interaction of the girls if there were multiple ones. Some of the conversations between them were very enlightening.
These 'sugar babies" would stay for terms from a weekend to few months. Usually, they left on good terms, but there were two who had to be forcibly removed. Stealing from the old, rich guy was their primary motivation.
He found it interesting to interact with so many different type of girls. All of them were more or less intelligent and he would enjoy just talking to them as well as the sex. He would explore each girl by not being the active participant, at least not initially, in whatever sexual activity there was, just laying back and learning how each one would interact with him and how they would try to seduce him.
But, as he got older, he had less and less need for physical release, but much more so for just the interaction. Not necessarily romantic interaction, but social interaction. He switched from sugar babies to high class escorts. They worked well, in the short term, and would occasionally stay for a weekend or accompany him on his business trips. He enjoyed the attention and like the arm candy the provided.
But, he was lonely.
He, currently, had no girls engaged, but he was looking at one or two more new long term wards, but he was picky. Occasionally, he would find a young girl hitchhiking or meet a girl at the store and invite them back, for money. He was surprises at how many actually agreed. Until then, he would, once or twice a week, engage a female escort from a reputable service he knew. Some of the girls were repeaters, if he enjoyed them. They were usually very good and if he was in the mood, he could "order up" a roleplay for whatever he was in the mood for. He had had two during the previous week and they were both interesting. But he found himself enjoying it more if there was actually someone in residence, someone who had taken the time to get to know him.
One Wednesday morning, he was sitting at his desk in the attic office, and his phone rang. He looked at it, puzzled. Very few people had his phone number, the phone was almost always for outgoing calls. He looked at the caller ID and did not recognize the number. He reached out and hit the speaker talk button. "Hello," he said.
"Mr. Sheffield?"
The voice was soft and feminine, high pitched like a child's, but with a tone of certainty and command. The words were not so much a question as a statement. "Yes, this is John Sheffield. Who is calling?"
"Mr Sheffield, my name is Ann Rogan. We have not been introduced, but I believe that you have been looking for some new, eh, shall we say, female personal service candidates."
He was a little taken aback.
"Please do not take this the wrong way, Mr. Sheffield. I am not a stalker or a kook. I was given your name by a couple of mutual friends, both of whom you have met with recently. We got to talking and they thought you were a very nice man, but felt a little sad for you. They thought that it would be good if you and I were to meet."
John thought back to which woman she could be referring to, but drew a blank. "And what would your friend's names be, Ms. Rogan?"
The voice, very sure of itself, answered, "You would know one as Monica and the other as Alex, but her real name is Clarisa. They work with David, as have."
He thought back to the month before. Monica was the name of one of his hired escorts, the one who he had ordered for a little black girl, Lolita type tryst. The other, if he remembered properly, was a tall thing blond and that had not gone well. "Oh, so you know David as well, do you?" David was the name of his escort contact.
"Yes. I have worked for him, on and off, for about two years now. I only do this part-time. I limit myself and tend to specialize."
"So, why have you called me, Ms. Rogan?" He tried to gather a proper tenor of authority in his voice.
"Mr. Sheffield, I believe that you will want to talk to me. I have an interesting proposal that would be beneficial to both of us. Would you be available later today? I can come to your house, if that would be acceptable?"
He had to admit he was intrigued. Her voice and the way she used the tone of it was somewhat attractive. He wasn't that busty today. If nothing else, maybe he would have sex for the first time this week. "I would be happy to have you come over today, Ms. Rogan. Your offer interests me."
"Thank you, Mr. Sheffield. I can be there in a few hours, shall we say 3 o' clock." Here voice now betrayed excitement. "I have your address and can take an Uber."
"Would you prefer I send a car for you? You sound like a young lady and I do not trust Uber."
She giggled, easily. It sounded like forest water in a running stream. "I guess it is a generational thing. I have had no problems taking an Uber. I can get there by myself, but thank you for your kind offer."
"If you insist. When you get to the gate, just announce 'Ms. Rogan to see Mr. Sheffield' and the security system will let you in. Take the car all the way to the front door. It is a bit of a trek from the front gate to the door."
"Thank you, Sir. I will see you at 3:00. Goodbye."
"Goodbye to you, Ms. Rogan." He hung up the phone. He was surprised at himself. He felt himself getting a little stiff in the groin region. It usually took much more than a phone call for that to happen. He continued with his paperwork, scoping out a new tech startup company that wanted his investment, but also felt a nagging anticipation.
He had just finished a late lunch, he always ate lunch a little late, when the home system announced "Sir, a Ms. Rogan has just been admitted to the front gate."
"Thank you, Jerry. I will answer the door myself." He responded.
"Very good, Sir. She should arrive in 5 minutes."
He put his dishes in the kitchen sink, he always ate lunch at the kitchen counter, and took a moment to look at himself in the stainless steel door of the refrigerator. He tucked his shirt tail and started towards the front door. Halfway there, he heard the bell.
He opened the door and saw a short woman. She was dressed modestly, but stylishly, her coat more stylish than functional for Chicago's winters. "Mr. Sheffield?" she asked, extending out a gloved hand. "I am Ann Rogan."
"Pleased to meet you, Ms. Rogan. Won't you please come in?"
She stepped in and started to remove her hat and coat, stomping a small around to snow on the tile entryway floor. "Here, let me help you with that." He said, taking her coat, hat and scarf and hanging them on the hooks next to the front door. As he turned back, he noticed a change. In her street clothes, she appeared much older than she did in her coat. He had reddish-brown hair, pixie cut short, and was wearing what appeared to be a rather expensive woman's business suit. She was short, at or a little under five feet, even with the short heels on her shoes.
"Shall I remove my shoes?" She asked. "I would not want to get snow water all over your beautiful wooden floors."
"If you want to, but I don't require it. Your shoes so look a little wet and can't be that comfortable. I do have house shoes available for guests. They are in the closet here. Your choice."
"That would be wonderful, Sir." She smiled and he went over and fetched her a pair. "My feet are freezing. That Uber had no heat." She took the low topped Uggs style slippers and pulled them on her feet.
"Won't you come this way, to the living room? We can sit and talk." he motioned towards the house's interior.
