Ann Ch. 01

"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?" My 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.