Ann Part Three
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Ann, Part 1, Introductions free porn video
Ann
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 c***dren, 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 c***d’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, l****a 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.
“Thank you.” She said. As they walked she passed by a mirror and saw herself. There was a stark contrast between here urbane and sophisticated clothes and the clumsy looking, but comfortable slippers. She stopped and giggled, her face completely changing as she did. She had appeared, at first, as a mature and cultured young woman but now her face made her look like a giddy young teen girl.
She turned and noticed his staring at her and immediately pulled on her erudite mask. “You will have to excuse me, Mr. Sheffield. I have a somewhat off kilter sense of humor.”
He let out his own chuckle. “Not at all, Ms. Rogan. I believe we share the same humor tilt. The visual oxymoron was funny.”
She nodded, “And here, I wanted you to appreciate how adult I am.”
“The c***d revealed was also enjoyable. Refresing.” He answered, turning and continuing into the living room. He led her to the chair conversation area and invited her to sit down. She did so, very properly, with knees together and hands lying on her lap. “Would you care for a refreshment?” he asked. “A glass of ice water would be nice.” She replied.
“Jerry, one ice water and one black tea, please.” He said to the air.
“Coming right up, Sir.” came the reply from above.
He turned his attention back to his guest. She had her “grown up” persona on again. She sat there very properly. Her hair was d****d with a part on the right and bangs sweeping down her forehead to the left. Her shoulders were square, displaying good posture. Here figure was medium. Her breasts were apparent but not huge. Here waist was slim, that which he could determine with here suitcoat on. Her hips were medium to small and her legs, as much as he could see with here below the knee skirt, were slender with small feet that were currently swallowed by the huge slippers. Under her blue suit was a white blouse that appeared to be silk, but did not have the complete shine one expects from silk.
Her face was oval, with a slight increase of point at the bottom. Her eyes were very large, green on color, and gave her a look of inquisitiveness. Here nose was small and slightly turned up, adding to the c***dlike side of her two part countenance. It looked like she had little makeup on, but He had long ago learned that any good makeup job looks that way. He towered over her at what he judged to be a little less than 5 feet.
All in all, she was a very attractive young lady. Cute, but nothing to write home about.
Just then, a powered cart came into the room with their drinks. It rolled over to her and as she lifted here water glass, she said, to the air, “Thank you, Jerry.” She was immediately answered with “You are welcome, Miss.”
“You will have to ignore, Jerry. His programming does not include PC word changes.”
“Oh, that is quite all right. I actually prefer Miss to Ms. The later seems so formal and cold.” She smiled, taking a sip of her water and placing the glass, very properly, on the coaster on the side table. “AI?” she asked.
“Yes, of my own creation. He looked up and spoke louder, “Mainly because no one else can stand him.”
“Sticks and stones, Sir. Sticks and stones.
Ann giggled, delightfuly.
“So, what can I do for you, Ms. Rogan?” He asked.
“I will be blunt, if I may, so as to save time?” She asked.
“Blunt away, my dear, if you will also excuse my old manners.” He answered.
At that, she chuckled and smiled. He liked her smile.
“Well, Mr. Sheffield, I understand that you are currently looking for some female personal assistants. I believe the current term is ‘sugar babies’?”
“Put crudely, as bluntness calls for, I suppose, but yes, I am looking for some new guests for my couch house.”
“David kind of filled me in on your history, and Monica and Clarisa were also helpful in explaining more about you. I believe that I can help you with your employee problem, Mr. Sheffield.”
“Is this a job interview, Ms. Rogan? And, please, given the topic I believe it would be better if you called me John.” He asked.
“I will continue to call you Mr. Sheffield for a bit longer, if I may. Later you will understand why. Yes, I was looking to interview with you, for both of our sakes. But I am not a ‘sugar baby’ candidate. I am here to make you a very serious offer.”
“Then what are you, Ms. Rogan.” He asked.”
“Please, it is entirely proper for you to call me Ann, and I even kind of liked that old ‘My Dear’. Let me explain a little bit more about myself. Despite my attempts to fool you, I am only 18 years old and turned 18 only 3 days ago. I wanted to wait until I could be completely ‘legal’, so as to not cause you any distress or liability.”
“I don’t understand,” he said, “I though you said that you have been working for David for a couple of years.”
“I was not working ‘for’ David, but ‘with’ David. As I am sure you are aware, there are men who do not care if the girl is of legal age, or even working of her own free will. They enjoy this, and David, under the table, provides them.”
“But you can’t be that young. I would have guessed 20 or 21. It’s just that you are so short. It makes you look younger.”
“Oh, I assure you, Mr. Rosen, under this suit and makeup, and adding a little bit of attitude, I can easily pass for 11 or 12 years old.”
“No way.” He said in disbelief.
“In a moment, I will prove to you, ‘yes way’”. I have worked for these clients for about 2 years. But I am only of limited use. I dance, tease, cuddle, give handjobs and oral sex, but I don’t fuck.” She turned very stern at those last couple of words. John was a little startled.
“And, yes, I am a virgin, although I will say this. About 9 months ago, a client got a little bit rough. He forced me down, over a table, tied me up and sodomized me. At the time, I was fighting for what I believed was my life and I didn’t have time to think, but after a little while (during which, David had that client given a little attitude adjustment, as we say in Chicago) I thought back to it and was kind of excited. I asked David to change my offering to include anal, just to try it out, and my bookings went up. Seems I like a lot of men like butt fucking a little girl.” She smiled, apparently teasingly.
After a moment of thought, John said, “I can see that.”
“I just bet you would.” She said, giggling. And, in doing so, John was not sure if it was her, or just his wishful thinking, that made her look years younger. “In any case, I have a great deal of experience, which I thought would be of some interest to you.”
“So, you want to be my butt fucking, little girl, virgin sugar baby?” He asked.
“No, not at all. Nothing so crass.” She said.
“I am sorry, that was rude of me.” He said.
“No. I do not want to be your sugar baby, Mr. Sheffield. I want to be your slave.” She straightened up in her chair, and assume a look of dead seriousness.
“My slave?”
“Yes, your slave, Mr. Sheffield. I want to be your collared, completely submissive, enthusiastic and playful slave. I am offering you my complete submission for whatever length of time you will have me.” Her face shifted, just for a moment, once again, and the look of a very scared but completely serious little girl flashed out.
“Well, that IS an interesting offer, especially for an old man like me. Is there a particular reason you have chosen me for this opportunity..” He said, somewhat stern at the surprise of the request.
“Please, Mr. Sheffield, do not make light of me. I am deadly serious.” She said.
“Oh, I completely believe you, my dear, and I do take this seriously. I can see from your face that you do as well. But, you are shaking, c***d. Do you fear me? Are you scared of me?” He stared into her face, gauging her emotions, which appeared to him to be changing a great deal, battling with each other.
“I am offering you chattel ownership, not only of my body, but of my mind, emotions and skills. I will not be a just a lay back and take it type slave, you wouldn’t want. From what I have determined, I will be a willing and obedient,” her eyes twinkled, “and sometimes mischievous servant to your every whim. I can be kind of a brat, at times. My sole purpose in life will be to bring you pleasure.”
“So, are there and restrictions, stuff I can’t do with or to you? I can do whatever I want?” He asked.
“Yes, you may. That is true. If you take me, I will give full and irrevocable permission. But. I must tell you, honestly, that this kinda scares me. But I think I know you and I trust you. In any case, even if I don’t want it or are scared to do something, I won’t have any choice. And you can always restrain me.” Again, her eyes twinkled at the prospect. “Sometimes, I kinda like that. Sometimes, I like rough.
“What about pain. I suspect you are aware, if you talked to Monica, that I can be very rough sometimes.”
She nodded, “Yes, she told me. And don’t feel bad, she does not hold that against you. She was just reacting as she thought you would want her to. She told me she actually liked that spanking you gave her.”
“Really! But I would want you to never ‘play act’ like that I do take you up on your offer. Always be honest with me.”
“Of course. But you have to allow for some role playing and teasing, right? I am a brat and I like to tease.”
“I suppose so. I just want any relationship we have to be honest and straightforward. No “playing the old guy”. OK?” His look was one of hopefulness. He had experienced too many girls who tried to play him.
She shrugged, looking deep into his eyes. “So, have you made up your mind, or do you want to see me naked right now to help you with your decision.” She asked, adding a little hip squirm at the end.
John sat back in his large, overstuffed chair, sitting quietly for a while before answering. It was clear that the decision was an important one for him and he intended to give it all due consideration. Ann sat down again and assumed a position of hopeful waiting, sensing that she should give him some space. Finally, he said, “I would like to have a day to think about this. Could you come back tomorrow? I can send a car to get you.” He said.
She smiled crookedly. “Or…. I could stay in your coach house.” She looked down, suddenly getting very serious herself. “I must make a confession, I brought all my stuff with me. It’s outside on the front porch. I was hoping to be able to sleep over, at least for one night.” She curled her lip and gave him what he could only understand as ‘The Eye’. She looked like a little girl who had been caught with her hand in the cookie jar.
“But of course. Let’s get your things and get you settled. Are you without any place to stay?” He asked.
“Yes, as of yesterday. Eviction.” She said, somewhat whiny.
“Well, regardless of whatever we figure out, I would not mind having you stay around here for a while. The coach house had more than enough room.”
“That would be wonderful, Mr. Sheffield.” She smiled.
“Don’t you think we can drop the Mister Sheffield stuff off now? After that offer, it seems a little stiff and formal.”
“No, Mr Sheffield. I will address you formally until you give me the honor of addressing you as my Master. This is very important to me, I hope you understand this. I know that this is a serious commitment and I want to handle it as such.” She stared at him, deadly serious. She paused for a moment, looking down and appearing to be in great thought. After a time she nodded her head like she had just decided something of great import. She looked up at him. “I have one other thing to tell you about me which may help you decide, one way or another. Mr. Sheffield, I am a masochist.”
“What do you mean, masochist? You like being hurt?”
“Let me tell you my history. I was raised in a rural family that was strict. As such, and being the mischievous person I am, I received a lot of spankings when I misbehaved. Mostly, it was my Mom that spanked me, but when I turned 12, my Father did the honors. When Daddy spanked me, it was different. When he did it, it was when Mom wasn’t home, with just the two of us in his room with the door locked and I was bare-assed naked. He spanked me a lot, but also took some time rubbing between my legs during the process.”
She shuttered, slightly, as if reliving the ordeal as she continued her story. John found himself entranced. “After a couple of months, Daddy spent more of his time rubbing me than spanking me. That is how I had my first orgasm and it happened every time, sometimes more than once for just one spanking.”
“Don’t get me wrong, he did spank me hard, sometimes with his belt and sometimes with paddle and sometimes with his hand and, once of twice, with a hickory switch. But I didn’t mind. He spanked me and it hurt but found that I loved the hurt. As I grew older, and after Daddy had finally gotten around to rubbing me long enough so I could cum, I found that I would also cum if I was first spanked long and hard enough.”
“Around about 13, while my breast didn’t grow, my nipples did, and they got hard whenever I was with Daddy. I had learned to perceive pain as pleasure. It was also about that time that Daddy started punishing me by putting himself in my mouth, and, later forcing his way into my throat. He never tried to fuck me, for some reason. All this went on for a couple of years, but by then, I had decided I had to leave. I was just 17 and I had seen the ads for some of the escort services and David took a chance with me.”
“So you see, Mr. Sheffield, if you take me as your slave, I will also, willingly and eagerly, take part in your foul moods where you want to hurt something. You can hurt me and I will take as much pleasure in it as you will. Probably more.”
John didn’t know what to say. Ann smiled and continued, “All of this, of course, assumes that you are a good businessman and knows the value of his assets and likes to invest in them. I trust you to see me as a special asset and I will do my best to be a special asset, one that is taken care of and cherished.”
John frowned, clearly uncomfortable with here use of financial terminology for such a delicate subject.
Sensing his distaste, she added, “Look, Mr. Sheffield, I know I am messed up. I have really weird “Daddy Issues”. I need a Daddy figure, not a Father figure, mind you. I am looking for someone older, wiser and most of all, kind, to help me. To protect me and take care of me and to understand why I sometimes act out. Someone who is kind and will help me. For that privilege, I would gladly sell myself into slavery. And it is only in a slave relationship that I can be protected. You can see that, can’t you?”
With that, she stood and said to the air, “Jerry, which room is available for me, and could you please indicate the way?” Jerry, the AI butler, asked, “Sir?”
“Put her in 101. Dinner is at 7:00, Ms. Rogen.”
“Please, PLEASE!’ she screamed, “Call me Ann. After I just bared my whole soul to you, just now, so I believe that you can at least do that for me.” She looked very emotional, a small tear running down her cheek.
John hesitated at the abrupt change. Calmly, he said, “Would you join me for dinner? Around 7:00, Ann. Don’t be late.”
Ann nodded, whipping her nose with the sleeve of her shirt, turned and walked in the direction that Jerry was indicating.
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 c***dren, 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 c***d’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, l****a 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.
“Thank you.” She said. As they walked she passed by a mirror and saw herself. There was a stark contrast between here urbane and sophisticated clothes and the clumsy looking, but comfortable slippers. She stopped and giggled, her face completely changing as she did. She had appeared, at first, as a mature and cultured young woman but now her face made her look like a giddy young teen girl.
She turned and noticed his staring at her and immediately pulled on her erudite mask. “You will have to excuse me, Mr. Sheffield. I have a somewhat off kilter sense of humor.”
He let out his own chuckle. “Not at all, Ms. Rogan. I believe we share the same humor tilt. The visual oxymoron was funny.”
She nodded, “And here, I wanted you to appreciate how adult I am.”
“The c***d revealed was also enjoyable. Refresing.” He answered, turning and continuing into the living room. He led her to the chair conversation area and invited her to sit down. She did so, very properly, with knees together and hands lying on her lap. “Would you care for a refreshment?” he asked. “A glass of ice water would be nice.” She replied.
“Jerry, one ice water and one black tea, please.” He said to the air.
“Coming right up, Sir.” came the reply from above.
He turned his attention back to his guest. She had her “grown up” persona on again. She sat there very properly. Her hair was d****d with a part on the right and bangs sweeping down her forehead to the left. Her shoulders were square, displaying good posture. Here figure was medium. Her breasts were apparent but not huge. Here waist was slim, that which he could determine with here suitcoat on. Her hips were medium to small and her legs, as much as he could see with here below the knee skirt, were slender with small feet that were currently swallowed by the huge slippers. Under her blue suit was a white blouse that appeared to be silk, but did not have the complete shine one expects from silk.
Her face was oval, with a slight increase of point at the bottom. Her eyes were very large, green on color, and gave her a look of inquisitiveness. Here nose was small and slightly turned up, adding to the c***dlike side of her two part countenance. It looked like she had little makeup on, but He had long ago learned that any good makeup job looks that way. He towered over her at what he judged to be a little less than 5 feet.
All in all, she was a very attractive young lady. Cute, but nothing to write home about.
Just then, a powered cart came into the room with their drinks. It rolled over to her and as she lifted here water glass, she said, to the air, “Thank you, Jerry.” She was immediately answered with “You are welcome, Miss.”
“You will have to ignore, Jerry. His programming does not include PC word changes.”
“Oh, that is quite all right. I actually prefer Miss to Ms. The later seems so formal and cold.” She smiled, taking a sip of her water and placing the glass, very properly, on the coaster on the side table. “AI?” she asked.
“Yes, of my own creation. He looked up and spoke louder, “Mainly because no one else can stand him.”
“Sticks and stones, Sir. Sticks and stones.
Ann giggled, delightfuly.
“So, what can I do for you, Ms. Rogan?” He asked.
“I will be blunt, if I may, so as to save time?” She asked.
“Blunt away, my dear, if you will also excuse my old manners.” He answered.
At that, she chuckled and smiled. He liked her smile.
“Well, Mr. Sheffield, I understand that you are currently looking for some female personal assistants. I believe the current term is ‘sugar babies’?”
“Put crudely, as bluntness calls for, I suppose, but yes, I am looking for some new guests for my couch house.”
“David kind of filled me in on your history, and Monica and Clarisa were also helpful in explaining more about you. I believe that I can help you with your employee problem, Mr. Sheffield.”
“Is this a job interview, Ms. Rogan? And, please, given the topic I believe it would be better if you called me John.” He asked.
“I will continue to call you Mr. Sheffield for a bit longer, if I may. Later you will understand why. Yes, I was looking to interview with you, for both of our sakes. But I am not a ‘sugar baby’ candidate. I am here to make you a very serious offer.”
“Then what are you, Ms. Rogan.” He asked.”
“Please, it is entirely proper for you to call me Ann, and I even kind of liked that old ‘My Dear’. Let me explain a little bit more about myself. Despite my attempts to fool you, I am only 18 years old and turned 18 only 3 days ago. I wanted to wait until I could be completely ‘legal’, so as to not cause you any distress or liability.”
“I don’t understand,” he said, “I though you said that you have been working for David for a couple of years.”
“I was not working ‘for’ David, but ‘with’ David. As I am sure you are aware, there are men who do not care if the girl is of legal age, or even working of her own free will. They enjoy this, and David, under the table, provides them.”
“But you can’t be that young. I would have guessed 20 or 21. It’s just that you are so short. It makes you look younger.”
“Oh, I assure you, Mr. Rosen, under this suit and makeup, and adding a little bit of attitude, I can easily pass for 11 or 12 years old.”
“No way.” He said in disbelief.
“In a moment, I will prove to you, ‘yes way’”. I have worked for these clients for about 2 years. But I am only of limited use. I dance, tease, cuddle, give handjobs and oral sex, but I don’t fuck.” She turned very stern at those last couple of words. John was a little startled.
“And, yes, I am a virgin, although I will say this. About 9 months ago, a client got a little bit rough. He forced me down, over a table, tied me up and sodomized me. At the time, I was fighting for what I believed was my life and I didn’t have time to think, but after a little while (during which, David had that client given a little attitude adjustment, as we say in Chicago) I thought back to it and was kind of excited. I asked David to change my offering to include anal, just to try it out, and my bookings went up. Seems I like a lot of men like butt fucking a little girl.” She smiled, apparently teasingly.
After a moment of thought, John said, “I can see that.”
“I just bet you would.” She said, giggling. And, in doing so, John was not sure if it was her, or just his wishful thinking, that made her look years younger. “In any case, I have a great deal of experience, which I thought would be of some interest to you.”
“So, you want to be my butt fucking, little girl, virgin sugar baby?” He asked.
“No, not at all. Nothing so crass.” She said.
“I am sorry, that was rude of me.” He said.
“No. I do not want to be your sugar baby, Mr. Sheffield. I want to be your slave.” She straightened up in her chair, and assume a look of dead seriousness.
“My slave?”
“Yes, your slave, Mr. Sheffield. I want to be your collared, completely submissive, enthusiastic and playful slave. I am offering you my complete submission for whatever length of time you will have me.” Her face shifted, just for a moment, once again, and the look of a very scared but completely serious little girl flashed out.
“Well, that IS an interesting offer, especially for an old man like me. Is there a particular reason you have chosen me for this opportunity..” He said, somewhat stern at the surprise of the request.
“Please, Mr. Sheffield, do not make light of me. I am deadly serious.” She said.
“Oh, I completely believe you, my dear, and I do take this seriously. I can see from your face that you do as well. But, you are shaking, c***d. Do you fear me? Are you scared of me?” He stared into her face, gauging her emotions, which appeared to him to be changing a great deal, battling with each other.
“I am offering you chattel ownership, not only of my body, but of my mind, emotions and skills. I will not be a just a lay back and take it type slave, you wouldn’t want. From what I have determined, I will be a willing and obedient,” her eyes twinkled, “and sometimes mischievous servant to your every whim. I can be kind of a brat, at times. My sole purpose in life will be to bring you pleasure.”
“So, are there and restrictions, stuff I can’t do with or to you? I can do whatever I want?” He asked.
“Yes, you may. That is true. If you take me, I will give full and irrevocable permission. But. I must tell you, honestly, that this kinda scares me. But I think I know you and I trust you. In any case, even if I don’t want it or are scared to do something, I won’t have any choice. And you can always restrain me.” Again, her eyes twinkled at the prospect. “Sometimes, I kinda like that. Sometimes, I like rough.
“What about pain. I suspect you are aware, if you talked to Monica, that I can be very rough sometimes.”
She nodded, “Yes, she told me. And don’t feel bad, she does not hold that against you. She was just reacting as she thought you would want her to. She told me she actually liked that spanking you gave her.”
“Really! But I would want you to never ‘play act’ like that I do take you up on your offer. Always be honest with me.”
“Of course. But you have to allow for some role playing and teasing, right? I am a brat and I like to tease.”
“I suppose so. I just want any relationship we have to be honest and straightforward. No “playing the old guy”. OK?” His look was one of hopefulness. He had experienced too many girls who tried to play him.
She shrugged, looking deep into his eyes. “So, have you made up your mind, or do you want to see me naked right now to help you with your decision.” She asked, adding a little hip squirm at the end.
John sat back in his large, overstuffed chair, sitting quietly for a while before answering. It was clear that the decision was an important one for him and he intended to give it all due consideration. Ann sat down again and assumed a position of hopeful waiting, sensing that she should give him some space. Finally, he said, “I would like to have a day to think about this. Could you come back tomorrow? I can send a car to get you.” He said.
She smiled crookedly. “Or…. I could stay in your coach house.” She looked down, suddenly getting very serious herself. “I must make a confession, I brought all my stuff with me. It’s outside on the front porch. I was hoping to be able to sleep over, at least for one night.” She curled her lip and gave him what he could only understand as ‘The Eye’. She looked like a little girl who had been caught with her hand in the cookie jar.
“But of course. Let’s get your things and get you settled. Are you without any place to stay?” He asked.
“Yes, as of yesterday. Eviction.” She said, somewhat whiny.
“Well, regardless of whatever we figure out, I would not mind having you stay around here for a while. The coach house had more than enough room.”
“That would be wonderful, Mr. Sheffield.” She smiled.
“Don’t you think we can drop the Mister Sheffield stuff off now? After that offer, it seems a little stiff and formal.”
“No, Mr Sheffield. I will address you formally until you give me the honor of addressing you as my Master. This is very important to me, I hope you understand this. I know that this is a serious commitment and I want to handle it as such.” She stared at him, deadly serious. She paused for a moment, looking down and appearing to be in great thought. After a time she nodded her head like she had just decided something of great import. She looked up at him. “I have one other thing to tell you about me which may help you decide, one way or another. Mr. Sheffield, I am a masochist.”
“What do you mean, masochist? You like being hurt?”
“Let me tell you my history. I was raised in a rural family that was strict. As such, and being the mischievous person I am, I received a lot of spankings when I misbehaved. Mostly, it was my Mom that spanked me, but when I turned 12, my Father did the honors. When Daddy spanked me, it was different. When he did it, it was when Mom wasn’t home, with just the two of us in his room with the door locked and I was bare-assed naked. He spanked me a lot, but also took some time rubbing between my legs during the process.”
She shuttered, slightly, as if reliving the ordeal as she continued her story. John found himself entranced. “After a couple of months, Daddy spent more of his time rubbing me than spanking me. That is how I had my first orgasm and it happened every time, sometimes more than once for just one spanking.”
“Don’t get me wrong, he did spank me hard, sometimes with his belt and sometimes with paddle and sometimes with his hand and, once of twice, with a hickory switch. But I didn’t mind. He spanked me and it hurt but found that I loved the hurt. As I grew older, and after Daddy had finally gotten around to rubbing me long enough so I could cum, I found that I would also cum if I was first spanked long and hard enough.”
“Around about 13, while my breast didn’t grow, my nipples did, and they got hard whenever I was with Daddy. I had learned to perceive pain as pleasure. It was also about that time that Daddy started punishing me by putting himself in my mouth, and, later forcing his way into my throat. He never tried to fuck me, for some reason. All this went on for a couple of years, but by then, I had decided I had to leave. I was just 17 and I had seen the ads for some of the escort services and David took a chance with me.”
“So you see, Mr. Sheffield, if you take me as your slave, I will also, willingly and eagerly, take part in your foul moods where you want to hurt something. You can hurt me and I will take as much pleasure in it as you will. Probably more.”
John didn’t know what to say. Ann smiled and continued, “All of this, of course, assumes that you are a good businessman and knows the value of his assets and likes to invest in them. I trust you to see me as a special asset and I will do my best to be a special asset, one that is taken care of and cherished.”
John frowned, clearly uncomfortable with here use of financial terminology for such a delicate subject.
Sensing his distaste, she added, “Look, Mr. Sheffield, I know I am messed up. I have really weird “Daddy Issues”. I need a Daddy figure, not a Father figure, mind you. I am looking for someone older, wiser and most of all, kind, to help me. To protect me and take care of me and to understand why I sometimes act out. Someone who is kind and will help me. For that privilege, I would gladly sell myself into slavery. And it is only in a slave relationship that I can be protected. You can see that, can’t you?”
With that, she stood and said to the air, “Jerry, which room is available for me, and could you please indicate the way?” Jerry, the AI butler, asked, “Sir?”
“Put her in 101. Dinner is at 7:00, Ms. Rogen.”
“Please, PLEASE!’ she screamed, “Call me Ann. After I just bared my whole soul to you, just now, so I believe that you can at least do that for me.” She looked very emotional, a small tear running down her cheek.
John hesitated at the abrupt change. Calmly, he said, “Would you join me for dinner? Around 7:00, Ann. Don’t be late.”
Ann nodded, whipping her nose with the sleeve of her shirt, turned and walked in the direction that Jerry was indicating.
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