Dominatrix System

With Sherry disappearing out my door to get her thoughts into order and a minimum assessment on her family to gather, I sat back down. The sissy with rest whip marks was on his knees, licking my pussy as I was in thought. I let Sherry leave and allowed her to gain some confidence. I was going to put her in place next time she came and start to twist her mind. I had many things going on, though, at the same time. Thinking about it all gave me a minor headache.

Sherry was under strict orders to determine the minimum it would take to hide an extended missing off her family. I would prepare my side for that as well. I had three options on that, but I was heavily leaning to the more disposable side. Everyone involved not under my control would find their way into the necromancers guild coffins. If Sherry weren't under my thumb at the end, she would join the others as well. I was putting too much at stake here to be kidding around with this kid.

I moaned lightly as the sissy mouse-kin between my legs found a sweet spot. My hands entwined in his hair. I forced his face in more, suffocating him as he licked my clit. My mind kept spinning as he did. I needed to talk to Cassandra and get an update. My healing was pretty much finished. I felt the sissy licking my pussy try to retreat in my hands, and I firmly stopped that. He tried his hearest, and I reached a light orgasm. I pulled his head back and let him breathe before forcing his mouth back to licking.

I leaned back, enjoying it for a bit as his pussy licking skills had definitely improved since he was put in my care. I felt myself reach the edge and go over my legs trembled as I orgasmed. I pushed his head off after riding out the orgasm. I sighed in pleasure and watched the little sissy on the floor, gasping for air.

"What are you?" I asked him.

"I am a Sissy, A toy for my owner's pleasure, Mistress Sally!" He answers despite his struggle to intake new air. He quickly got his wits about him after coughing a bit.

"Present me your ass," I told him, and his body quickly put him on his feet. He turned his ass and split his ass cheeks. His little puckered asshole was plugged up. I reached out and started to pull the plug out of his ass. I watched as his moderately sized cock started to harden as I did so. A six-inch-long with a two-inch base butt plug appeared as I pulled it out. His little hole gaping as I did so. I inspected the clean inside and nodded. Freya had taught him proper anal cleaning as it looked like. The little mouse-kin looked forward to presenting his ass hole without changing stance. I stuck a finger inside and located his prostate quickly.

I started to stroke where his prostate was slowly and heard him moan. The moans slowly grew louder as I stroked it harder and faster. "Tell me, little sissy... How do you feel?" I asked. I started to press it harder.

"I feel good, Mistress Sally!" he told me.

"Where do you feel good, little Sissy?"

"My ass pussy, Mistress Sally."

"Why do you feel good here?" I asked as I pressed down hard on his prostate. He moaned loudly as I did so.

"Because I am a Sissy toy for my owner!" He exclaimed. I gave him a spank across the ass but not too hard. The smack sounded in the quiet room.

"Good job, Perfect answers deserves a reward." I pulled out of his ass and noticeably edging the sissy right before he orgasmed. I blue balled him and started to walk towards the training room. "Follow me, sissy, for your reward," I told him, and I heard his steps behind me. He came in behind me as I stepped into the room. I looked over the toys the amateur used before. The flogger was used along with a variety of clips. The variety of dildos laid used. Sherry has only used the stick and didn't give much pleasure to the sissy. She only used the dildo's to stretch him. It wasn't very effective either since she found out the hard way we had already been doing that. Most of the toys here left unused could only fit in Freya. This little sissy hasn't had the training to the point to take them.

I went and grabbed my strap on that I stopped her from using. I turned to the sissy. "Get it ready for your ass," I commanded him. The strap on was twelve inches long and two inches thick, making it pretty standard. I had it enchanted with a vibration feature as well. I kept the feature off, and I shoved it into the sissy's mouth. I guided a hand across his whip marks. He groaned from the pain while he gagged on my cock. I started to rock my hips deeper into his throat, making him gag louder. I started to fuck his throat listening to his gagging as eight inches made it into his mouth. I fucked his throat harder, forcing it deeper. I heard his small groans and whimpers as I did so. I then pulled it out of his mouth with my hand in his hair, turning his pathetic face to look at me. "Sissy, are you feeling rebellious now?" I asked.

He shook his head. "Show me your submission, sissy," I told him, and he was on his knees with his ass in the air. Licking my feet. Slowly his tongue lapped at my toes and between. I lifted the foot he was licking and stomped his face into the ground. I then forced the foot into his mouth. "What do you want, sissy?"

"Fuck my Ass, Mistress Sally, Please!" He exclaimed as my foot rubbed his spit all over his face.

"Turn around and show me your pussy!" I commanded, and he made haste turning around, showing me his asshole. I lined up the dildo to his ass, and I drove it all in at once. He cried out as I penetrated him. I didn't give him a break as I took hold of his hips and forced him onto my cock. I started to use mana to move it even faster and rocked my hips to thrust even harder into him. I watched cum spray onto the floor as I worked his ass and prostate. He came again quickly, and I freed a hand to start spanking his ass as I did so.

"What are you?" I asked again as I pounded his ass pussy.

"A Sissy Slut!" He replied loudly while moaning.

"Repeat yourself until I tell you to stop!" I commanded as I pounded his ass pussy.

"IM A SISSY SLUT, IM A SISSY SLUT, IM A SISSY SLUT!" He continued to yell in the room as I pounded his ass pussy hard while spanking him. His ass cheek's color started to turn red, growing a deeper shade of red as I spanked his cute little ass harder. I fucked his ass hard as I saw him cum for the fourth and fifth time. His legs shook as he repeated himself. "IM A SISSY SLUT!" as I commanded him too. I watched as his spunk spewed out for the seventh time when I stopped fucking him. I let him stop to the ground and into his puddle of cum. I withdrew from his ass and leaned down beside him. I grabbed him by the hair and moved his head. I put his face into the puddle of cum. "Clean it up, Sissy slut!" I commanded.

His tongue reached out and slowly started to slurp the cum off the floor. I watched as he slowly licked up the mess his cock made and nodded in satisfaction when it was done. I nodded to myself as well, thinking it was time for the next lessons. I stood up and looked around the messy training room.

"Sissy bitch, I want the entire apartment cleaned when I get home. I will be getting in the shower to do an errand. If I come home and you haven't cleaned the entire place, then a reckoning you will never imagine will come upon you. But you wouldn't disappoint me, right, Sissy?" I said near his face.

"No, Mistress Sally. Your wish is my command!" He exclaimed, terrified of any repercussions.

I lightly smacked the dry part of his face. "Good little sissy bitch. I will be back soon..." With that, I stood up and left the room to the shower. I would need to do some things tonight, and checking in with Cassandra was the priority. I took a shower letting the water fall onto me. I cleaned myself up and got dressed and ready for battle. I walked out of the house and told Freya and Stacy to check in on the sissy bitch upstairs. They both acknowledged my order, and I left into the streets. I looked into the sky that was starting to darken into dusk.

I traveled the unnamed alleyways making my way across the city unseen. Soon I reached the slums, walked into the house, found the passageway down, and entered the hideout. Inside was empty, and I walked past into the room where we planned. I heard yelling inside.

"Dammit, Carl! It just doesn't work that way. They have more trained people than we do! Our gang is gutted and shy from long periods of us reaping our own numbers. We haven't had time to consolidate and create a new core from the members. We needed to get rid of the informants; that is for sure, but we are weak. The Gang we have started a war with is still strong in numbers even after our initial attack. The only thing stopping them from attacking us in numbers and taking back territory is the FUCKING GUARDS! The guards are impeding us from consolidating too. Three new guard captains have moved into our territory and are exploiting us. I prefer them at this moment. What you want to do, though, will break the balance that has established itself. WE CANNOT BREAK THAT!" I opened the door to see Cassandra yelling at Carl, who clearly wanted to fight.

I stepped in and recognized this wasn't the first time they had this fight. Not this wasn't the first time Cassandra explained this to Carl. I stepped into the room, gathering both their attention.

"Mistress!" They said at the same time as I entered. I walked in, closing the door behind me, found a chair, and sat down.

"Cassandra... What is the low down on our situation? I have healed up, but I don't want to battle yet. I have something big in the works, and I need information." I sat back in the chair. I made that chair look like a throne with my aura alone.

"Sigh, I was just telling this idiot... But you do need to know. Our backing off put the enemy gangs on alert, knowing we are eyeing them. They all saw the attacks our gang did on the other side while we sneakily took parts of the Dock territory. We carved out about thirty percent of the Docks for ourselves. The problem is we got barely any of the warehouse districts and took mostly the whores and prostitutes. This means we took no power but all the pussy. The gangs there are pissed. I have set up gang members to protect our current territory. The problem is that they are weak as shit. We have no disposable people of D-rank. We have one C-rank gang member, and she is more suited to finding information. Then there are the guards. They have started to invade our territory. Our gang members are starting to get targeted and harassed. As long as they stay in the letter of the law, we can defend ourselves, but some of these guard captains don't care. It is pissing off a lot of the gang members. With the cleanout inside of the gang, people are on edge. Now the good news is we do have a small cadre of members I trust moving forward. The bad news is we need more time." Cassandra finished.

"Carl, your turn..." I turned to him.

"I have been training these bunch of weaklings. Out of the men so far. I think six have the potential to break into C-rank soon. The rest are D-rank. Cassandra wants to put them out there to get more experience and increase our numbers. I have been fighting it. These guys are still growing in my training program." he finished his small report, and I stared him down.

"So that is it? Fine, I will settle this argument. Cassandra, you take half the people he is training. Not the ones with potential for C-rank at this point. It is rare to find this many under our thumb take half the D-rankers and buff security in key areas. Carl, find more potential in our ranks or recruits, then train them. You know what you are doing. Next, Cassandra, I need you to find various addictive substances. I don't need them in large quantities, and I don't have a use for them yet. They are a backup plan. Get them as soon as possible. Tell me about their properties and what they do. Tell me how readily available they are and the price. I need the low down at this point though we are not getting into the drug game. We can set up a gambling den soon, though."

"Next is I want to lay down for a while. I have a plan for something, and I might need you guys at full strength. So, consolidate it. Grow and secure territory. If you think they want it too badly and will fight for it, then secede the territory. Make it hurt, though. Do not just surrender it. Kill as much as possible while backing off. That is only if they push it to the point where we stand to lose more than we gain. Every time we back off territory, we gain more members to defend. Make them think they are winning for all I care. The reputation of this gang means nothing at this moment. We are too fucking weak. We already have a reputation for being extremely cut-throat, so we can see where we go from there.

"Next, Cassandra, I want you to come for a report at least twice a week if you can. If things are too hot and you don't think you can make it without being spotted, don't. I want you to practice discretion. I know you both know how to do it. Carl, I need you to stay calm and do what you need to do. If everything goes to plan, we will have a whole new city to play in. Patience is a virtue, and I need you to keep yourself in check." I sighed, finishing this. "I have liked your progress so far and will reward you amply after this. The plans are underway and doing great. I want you both to think of something that you would like to be rewarded. Do you both understand?" I finished asking that question.

"Mistress... What is the plan?" Carl asked, and I turned to him.

"I will not tell you at this point. Since at this point I don't need you to do anything with it. This is called a Need to know, thing. If you don't need to know about it, I won't tell you about it. If you are involved in some compacity, then I will. Understand?" I asked again.

"Yes, Mistress," I nodded to Carl and turned to Cassandra. I raised an eyebrow.

"Mistress, I have one more thing to report..." I watched, and she took a deep breath. "The Necromancers Guild knows I am only a mouthpiece. They want to meet my Mistress or Master. They don't care whom. They just want to deal with the head and not the neck." She finished. I paused, thinking this over. My mind spun as fast as it could, weighing the pros and cons of such a meeting.

"Fine," I said with a sigh. The Necromancers guild was important moving forward, and I was looking forward to meeting a necromancer in person for the first time. "The ground will be neutral of our choosing. I will not show my face at all, and neither do they. I will find a place to set some things up to protect both our Identities. Understood? If they don't like it, then they cant meet me. This is the best and the bottom line of my willingness."

"Understood, Mistress, I will let them know." Cassandra nodded.

"Anything else before I leave?" I asked them both to see them both shake their heads. I sighed and started to walk out. Fuck I am busy, I thought to myself as I entered the streets, thinking about the meetings ahead of me with The Nobility, The necromancers. The City lords family. A lot was going on, and I was knee-deep in the swamp of this city. I planned just to pass by. The city was about to erupt in change. Only the city didn't know yet as the tides turned underneath the surface.