Chapter 6

As I pulled the car into the garage, Aimee turned in her seat and asked Lily to take Natalie and Barbara into the house and assume their positions. Lily saw the look in Aimee’s eyes as one of concern and started to ask what was going on? In a stern voice Aimee told her, “No questions just do it.”

Lily almost jumped out of the car, looked over at Natalie and Barbara as she said, “come.”

After they left and were in the house, Aimee turned to me and said “I am going to be punished aren’t I?”

For the first time since we left the restaurant, I actually smiled and told her probably, but we must talk first.

As we started out of the car, I asked Aimee, “Please go up to my room, remove all of your clothes and wait for me. I will be up in a little bit, I am going to get my head straight and tell Lily that if we are not down in thirty minutes for her, Natalie, and Barbara to clean up the downstairs. If we are still not down to assume their positions again.”

As we walked into the living room and saw that Lily, Natalie and Barbara had assumed their positions, I noticed Aimee shake her head and proceed down the hall. Lily, Natalie, and Barbara watched her go, and then their eyes turned to meet mine.

Lily couldn’t contain her tongue and asked, “What is going on?”

I went to her and knelt down, placed my hand on the side of her face and told her, “Aimee has been a very bad girl and we needed to talk.

Lily still the inquisitive one asked if she was going to be punished, with that statement I heard an intake of breath from Natalie and Barbara, but no questions. But Lily wouldn’t let it go and asked, “Master I need to understand, you did not say one word to her about being bad. How does she know?”

I just smiled, “Lily, your Mistress is very intuitive and I don’t need to talk to her, somehow she just knows. Now you have also been a little bit bad yourself. A quick moment of disbelief crossed her face and she asked how she had been bad.”

I asked, “Think about it for a minute.”

I saw the realization cross her face. “I was about to question her request and she saw it on my face and stopped me. Then she told me to take Natalie and Barbara and to go. Am I right Master?”

I told Natalie, “You are correct. Your Mistress is extremely intuitive and knows things without being told. You are not going to have your hands full pleasing her as she is easy to please.”

“But Natalie, you are going to have to learn to keep your emotions and feelings off your face and from your actions. She can see right into people’s souls and see their true meaning and intentions. I also believe that you are one very lucky submissive, she will care for you as if you are her very own child.”

“So, when we come out of the bedroom, if she feels a need to punish you for what you did, just take it like a woman, and you will be better for it. Do you understand?”

Lily nodded her head, “Yes Master.”

I smiled at her, “Lily, you will be great, just continue to learn from your Mistress and Natalie will stay with you forever. Barbara still needs to make a decision about what to do. And just between us, I am also lucky to have Aimee. She already knows it, because she sees into me just as she does everyone else.”

I stood and went to the kitchen and returned with a timer. “If this timer dings before we return, I want the downstairs cleaned up and ready for tonight, if we are not back by the time you finish, return to your positions and wait for us.”

“If I am not mistaken, we may have a visitor tonight.” With that, I stood and went upstairs to my bedroom.

It had been almost 20 minutes since we arrived home, as I entered my bedroom, Aimee was in position in the center of room.

I let her stay there while I stepped into the restroom and readied myself for something I hadn’t done in a very long time, at least two and half years or more due to my wife’s extended illness. As I got myself ready and in the right frame of mind I stepped into the bedroom.

I looked at Aimee, “You already know what you have done. I wanted her to know that I knew all about her abilities. What do you think I should do about it?”

Aimee looked up at me, “I found a leather paddle in the closet where your wife’s clothes are stored.”

I asked, “Please go and retrieve it, bring it back to me.”

She retrieved it, and then she handed it to me and returned to her position.

I knelt down in front of her, looked her in the eyes and asked what she thought I should do with the paddle.

She said that ten swats should be enough if you don’t go easy on me like you did with the swats in the kitchen.

Aimee told me, “I need to know what real discipline is like, before we talk tomorrow morning. I need to know if I can I take it and still stand by your side and trust you.”

“I already know that you are a caring man and will take care of me and protect me, no matter what. But, I need to know that you can control me without me being afraid of you. That you do not rule by fear like that asshole I work for.”

This caught me totally off guard, I knew more about her than she thought I did. I research everyone that falls within my range of influence.

What I learned about her is that she worked for one of the companies I used to own. I filed this information, to be discussed tomorrow. I looked at her and told her to lay face down on the bed, spread eagle with her arms stretched above her head and her legs spread toward the lower corners and for her not to move.

I approached the head of the bed, opened a compartment and pulled out a pair of padded hand cuffs securing her hands. I went to the foot of the bed, reached under and pulled out a leg restraint securing that leg. I repeated the process for the other leg.

I walked around and sat on the bed near her head. I reached out and rubbed my hand up and down her back and across the cheeks of her ass. She looked up at me and I could tell she was more than a little nervous, she was actually scared. I told her that it had been a long time since I have used these restraints. Though my wife took her punishments like a woman, she made me use these so she didn’t run out of the room screaming.

I told Aimee that our sex afterward was always very enthusiastic and inspired. She hated pain more than anything. She also knew that it was part of the deal and this is what we came up with so she could get through it.

“What do you think? I want your true opinion. So, speak freely.”

Aimee said, “Master, I know I overstepped my position when I gave Traci my number without discussing it with you first. I need a reminder not to do it again. I need you to really discipline me, the real way. I need to know if I can take it, I mean really take it. I have not, and I mean ever, been so happy in my life than this weekend. I have already made up my mind to a 90% level what I want to do tomorrow. The other 10% deals with this.

Aimee continued saying, “Yesterday you played with my ass. You spanked me and I kind of liked it. But, again, it was just playing around. This has to be real. I need to scream in pain. My girl’s sitting downstairs need to be afraid for me, so when we go out there, they know, without a doubt that it can happen to them. They need to hear the paddle contact my ass, they need to hear me scream, and they need to hear you make love to me after you do it. You need to make me scream in pleasure after you beat my ass.

Aimee said, “Master can you do this for me? If you can do this, I am yours forever. I am begging you to do this.”

I said, “What you did, does not warrant anything this extreme, but I will do it for you. Are you ready?

Aimee said, “Master, I may never be truly ready, but let’s get this done.”

I walked across the room, opened the door and returned to her.

I said, “Aimee, you need to count each one out loud. If you miss one we will start over, do you understand.”

She replied, “Yes Master.”

I stood up and without waiting I struck her ass as hard as I could, she yelled out and said, “One.” I followed with another, then another with the same results.

I noticed movement by the bedroom door.

As I looked over at the door I heard the crying voice of Aimee yelling at them, “Come over by the bed and assume the position, you are next for leaving your positions by the fireplace.”

They hesitantly did as Aimee told them to do.

I proceeded to finish with Aimee’s ass. She was sobbing when I finished, I noticed that her ass was already showing some bruising and was beet red.

I requested, “Lily to go into the bathroom and retrieve the ointment and lube from my medicine cabinet.”

I said, “Natalie, retrieve my pump from the top drawer in my closet. I knew she knew where it was because she cleaned and put it away this morning.”

Barbara looked at me expectantly, “Can I do something?”

I replied, “You are not collared and should watch us, as this is part of our lifestyle.”

Lily handed me the ointment, resuming her position next the bed.

I gently applied the ointment to Aimee’s ass, I noticed the plug and remembered that I needed to change it for the next larger one. I slowly removed it and handed it to Lily asking her to clean it and return to her position.

Natalie brought my pump over. I requested, “Natalie, use the pump and help me to an erection.” She proceeded to give a sloppy blowjob, starting the blood flowing, attached the pump to bring up a seven to eight-inch erection.

As I finished with the ointment on Aimee’s ass, her body started to relax as she stopped crying, partially due to the cooling effect of the ointment.

I requested, “Lily, please get me plug marked as number three and lube up Aimee’s ass. When Lily was done with Aimee’s ass, I slowly inserted the butt plug, and leaned down speaking into Aimee’s ear.

I told her, “I am going to give you an orgasm like you can’t even dream of.”

Aimee started shaking her head saying, “Please Master, not now, I am too sore.”

I told her, “It feels better and stronger this way, but it still hurts.”

Aimee asked, “Please Master, can’t we wait?”

I told her, “No, it has to be now.”

Lily informed me, “My Mistress is ready to go and very wet.”

I requested, “Lily return to your position by the bed.”

Reaching into the nightstand, I pulled out a two inch diameter ball, turned it on, and it started vibrating.

Lily saw it, looked on in wonder asking, “Where did you get that?”

I smiled at her and said, I have my sources as I slipped it into Aimee’s pussy. I couldn’t believe it, she actually started purring. She couldn’t help it, the reaction was almost instantaneous.

I turned on the new butt plug, her reaction was instantaneous, her entire body started shaking and she was moaning in pleasure. The pain of the paddling was forgotten.

Aimee squealed through the first orgasm as her body was seizing through multiple smaller orgasms.

I removed the restraints from her wrists and legs and rolled her over on her back. I then positioned myself between her legs and pleasured her with my tongue as she continued to have mild orgasms.

I pulled the ball from her pussy, lined up my member and drove it all the way to the hilt in one motion. She arched her back so only her head and feet touched the bed. This pushed her over the top, creating too much physical and mental stimulation, she collapsed on the bed unconscious.

I removed myself from inside her body and lay next to her, pulling her into my embrace. Natalie gasped, staring in disbelief, “I have never seen anyone pass out from too much pleasure. I know it happened to me last night, but seeing it is something else.”

Natalie exclaimed, “Oh my god, I want some of that.”

Aimee stirred to consciousness, she softly said, “I thought I had died, but woke up in heaven. You threatened me with something like this, but I didn’t believe it could happen. I don’t have to wait until tomorrow morning, you can have me now, and I am yours.”

I asked Lily, Natalie, and Barbara, “Please go out to the living room. Close the door as you leave. “I have some things to discuss with your Mistress before we go any further.”

As they left, Aimee looked into my eyes with pure love and trust. That is the only way I can describe it.

Aimee said, “I need to be more disobedient to receive more reminders like that. That was so intense, I can’t believe it happened. Did I really pass out from too much pleasure as she started to shake with another orgasm; it was then that I remembered to turn off the plug in her ass.

I asked Aimee what legal office she works at, as a forensic accountant.

Aimee said, “It is a subdivision of Winslow and Company. The manager’s name is Henry and I said Stein.

Aimee looked at me, “How do you know?”

I told Aimee, “You are about to learn enough about me that may make you rethink staying with me forever. You don’t know my last name yet, do you?”

She answered, “No, I haven’t looked at my choker so I could hear it from you on Monday.

I instructed her, “Please go and look in the mirror, look at the collar and see my last name.”

Aimee replied, “I don’t think I have enough energy yet to get up. Please just tell me.”

I told her, “My last name is Winslow.”

Aimee said, “Wait a minute, as in Jerry Winslow.”

I nodded my head.

She asked, “Not Jeremiah Winslow, but Jerry Winslow?”

I explained to her, “Jeremiah is my given name, but I go by Jerry in all business matters so that I can keep my lives separate. The thing you need to know is that I am the Master of Masters West of the Mississippi. Of the 250 or so registered Masters, I am number one in the pecking order and your manager Henry Stein is around number 50 and soon to be ex-manager Henry Stein.”

I explained, “I have a meeting with the partners, or board of directors, who purchased my businesses tomorrow at noon. The meeting is to address Mr. Stein’s actions. I received an email last week regarding a number of complaints that a certain Master has been getting a bit out of line with his submissives. Especially the ones who remove his collar due to the mistreatment he likes to give out. It seems he runs his harem as if they were slave’s verses people who have a choice in who their master is and what they do.”

“When I received this email, I contacted the board and asked if there were any open claims or complaints against this guy. They asked how I knew. I told them I would explain at a luncheon with the board tomorrow. I will handle both issues at once.”

I asked Aimee, “What position are you in the hierarchy at the business office?

She answered, “I am the top accountant, which places me number three in the chain of command.”

I asked, “What do you know of the number two person at the firm?”

Aimee responded, “I think she is quite subservient and now that I know he is a Master, I believe that she is his submissive. That is, now that I have been living the life for a few days. Looking back, I can see she never leads and acquiesces to all his decisions. I always thought it weird that a number 2 would never stand up for anything, now it seems clear.”

I asked, “Aimee do you think you could be the number one person and manage the firm?”

Aimee replied, “I haven’t thought about it, the top job had always been filled by an attorney.”

I informed Aimee,”When my wife bought the firm it was run by an accountant. When my wife bought the company, the accountant retired. She was the owner and only sold because she wanted to retire.”

I told her, “Think about it. If what I believe is going to happen, actually does. I will need someone I can trust to step in and take over. I believe one of the board members has been intimidated by Henry. He may even be in Henry’s organization. It is the only way for him to become the manager, because from what I see, he has no management skills. I am going to send out some inquiries and find out who actually recommended him for the position.”

“This happened while I was on travel for the company and the board approved his promotion. I need to do more homework before tomorrow morning.”

Aimee explained to me, “You need to be careful, he is a pretty big guy and loves to intimidate whoever disagrees with him.”

I smiled at her, “I am not the Master of Masters because I am easily intimidated or easily taken down.”

Aimee smiled, “Aaah, now I get it, the guy at the club never stood a chance, did he.”

I laughed, “No, he didn’t. I worked my way from a fresh new recruit to commander of Seals while I was in the Navy. I really can take care of myself as I specialized in hand to hand combat and field command. Everything I just told you is between you and me.”

Aimee looked at me, “Absolutely, I understand.” Aimee looked intently at me and said, wait a minute. If you are Master of Masters, what does that make me if we stay together after tomorrow?”

I laughed and replied, “You immediately become the Mistress of Mistress’s.”

Aimee smiled and asked, “Do I even want to know what that means?”

I explained, “It means that you are in charge of all Mistresses. You will be challenged as much or more than I have been. But, you have one advantage over everyone else.”

Aimee asked, “Exactly what advantage would that be.”

I smiled and simply replied, “Me. I will always have your back, just as I did for my wife. No challenge to you happens without me being at your side. You will see that we cannot be challenged if we stand together.”

Aimee nodded with a little concern on her face. “I could see the trust in her eyes. We are a team.”

I explained, “Aimee, I have been neglecting my duties lately. I have four under Masters who have been handling everything. There have been a couple challenges to my position, but these four are so strong and devoted to me, they have handled all the challenges.”

I said, “Aimee, let’s get back on point here. It’s time for you to discipline your girls. My suggestion is that you administer to Lily. Remember she now has two transgressions, one for questioning you, and the second for leaving her post when I was playing with your ass.

Aimee laughed, “Master, is that what you call that. I think it could be construed as abuse. But I’ll settle on discipline.”

I laughed, “I can’t wait to do it again.”

Aimee looked at me, “I can’t either.”

I suggested, “Aimee, Lily gets three for questioning your authority and 5 for leaving her post. Then you pleasure Lily with an orgasm she will never forget. I suggest you put the ball into her pussy and turn it on before you paddle her. Restrain Lily on the bed face down, lube her ass and insert a six inch dildo in her ass and turn it on. Then administer three swats for the car incident, take a short break explaining the next five are for leaving her post. Make sure she counts each one, just as you did. Because pleasure and pain can become intermixed, you will notice minor orgasms as you paddle her.”

“Aimee, then apply the ointment to Lily’s ass and pleasure her until she passes out.”

“Next you instruct Lily to restrain Natalie as you did Lily. Have Lily administer 5 swats to Natalie’s ass as hard as she can, apply ointment, then you both pleasure Natalie until she passes out. In the other night stand is an array of different size dildos to choose from. Pick one for each and use it on their asses.”

Aimee said, “That is going to put them over the top.”

I told her she would get one as Lily would administer to Natalie as she pleasures her pussy and yours would be on Natalie’s face.

Aimee said, “Fair enough, at least I get my pussy eaten, again.

I asked, “Do you need me to witness the administrations of discipline?”

Aimee answered, “No, I can handle it. But Master, we have to answer the question regarding Barbara.”

I told her, “That will have to be up to Barbara. We have an assumed agreement, but we don’t really know where she stands in regards to joining us. Why don’t we force her to make a decision?”

Aimee asked, “How do we go about that.”

I suggest, “When you and Lily finish taking care of Natalie, you should leave the room. My guess is that Barbara will stop you before you get out the door.”

Aimee thought for a moment, “I think you may be right. Barbara will want to know why she is being left out.”

I smiled, “Please continue.”

Aimee explained, “I will tell Barbara that we don’t have an agreement with her regarding anything other than staying with us and maybe experience how we live. We have no agreement regarding punishment.”

Aimee asked, “What do I do about Traci when she calls? I could see in Traci’s eyes and actions that she was jealous about how happy we all were. Only to find out we were all your property and were happy with it. She also feels that her life sucks. Traci is very insecure, she may even be envious that everyone she grew up with has moved on and she hasn’t. Her home life may not have been the best either. I think she needs us, what do I say when she calls.”