Coming down from my Height with my new sissy still between my legs shuddering in pleasure slowing down. I removed his head looking at his red face lost in the pleasure dripping with my juices and his spit the smile I wore was huge I let him come back to himself as his eyes focused on me. Letting my smile stay I tossed his head back throwing him to the ground. I step away from my discarded clothes and the general mess left behind from my playing with him.
"Clean that up, Sissy," I command walking over to my dresser so I can put over to the bucket that I use to wipe the grime off my body and proceed to clean myself. I watch as Derek looked at a loss of what to do. I grab and extra cloth dip it in the water and toss it at him. "I will not say it again clean up." He still on his knees starts to clean off his face then down to the cum on the floor rubbing into the floor more. I let him get away with it for now, but I will fix this later with some training. I watched as he cleaned up pathetically and look at me before leaving the room in some now dirty maid clothes.
I pushed him far today, Maybe too far but I will train his masculinity out then I will train him to be my perfect slave that does whatever I want. I know I haven't stopped smiling and I was in contemplation on how to proceed. This was the first time I have ever done this last life I was more worried about growing my gang and increasing my power over others through blackmail and powerplays killing who stood in my way. But after this experience, I learned what I was missing. It was like a hole in my life was just filled, and I knew already it was an addiction I will never get over in my life. I didn't want to either.
I set aside my thoughts on that and proceeded to look at my System since I just got points for the first time.
--
Status.
Name: Sally
Age: 10
Titles: Slave, Apprentice of Jack the Torturer, Martial Genius
Race: Beastkin - Phantom Snow Tiger
Level: 1
XP: 0
System Points: 15000
Strength: 15
Agility: 35
Vitality: 18
Intellect: 43
Wisdom: 53
Luck: 10
Points to Spend: 0
Shop - New Items Available
Inventory - unavailable
Lotto - No spins
--
Shop
Talent Shop
Skill Shop
Item Shop
Stat shop
--
--
Talent Shop
Whip Talent - 1000 points
Sadistic atmosphere - 1000 points
Intellectual - 2000 points
--
--
Skill Shop
Inventory - 2000 Points.
Mana Cultivation - 4000 Points.
Enrage - 2000 Points.
Tailoring - 2000 points.
--
--
Item Shop
Level up Candy - 1000 Points.
Chastity cage - 500 points
Corset - 500 points
A bolt of Enchanted Shadow weave Cloth - 10000 points
--
--
Stat shop
Charisma Candy - 1000 points
Agility Candy - 5000 points
Toughness Candy - 1000 points
Luck Candy - 2000 points
--
Interestingly I have fifteen thousand points available and I can still do spins but chances are against me. If I have extra points I can try my luck but like in my past life don't gamble your mortgage gamble money you don't mind losing. I can lose these points to chance.
I was tempted for the talent in whips wondering if it would increase the speed and skill I could use whips. I was getting really good at them and bladed whips were just around the corner. That cloth bolt being that expensive though had questions running through my head why the system classified as worth so much. I still haven't earned any experience though so I wasn't sure how to level up making the candy valuable the questions in my head about it were running. Was this the only way to level or did I have to kill things or dominate someone even more thoroughly?
As I was thinking I laid on my bed and slowly drifted to sleep. That night began a thoroughly exciting time for my training still sucked but I came to the conclusion to pick up Mana cultivation and Whip Talent I picked up Intellectual and tailoring. I needed questionable things made with discretion my mother has other duties so I picked it up filling my day even more. Mana cultivation was basically a step up in Meditation focusing on the mana around me making a core of mana within myself. I had no idea what it uses are but my mind feels weirdly cleaner with it. Intellectual was a basic talent increasing the wisdom and intellect a gained each level by one useless to me right now. Last but not least was Whip talent, Whips became easier for me to understand my torturer was happily surprised how much faster I was picking it up. This increased the speed at which he tortured me.
The days of torture for Derek increased as he was banned from boy underwear and exclusively wore cute panties. His teachers were happy with new changes in his behavior as I told him to pay more attention in class or I would punish him. Therefore I purchased him a chastity cage it came in a cute pink and the system gave me a key and a description that put a smile on my face.
--
Sissy Chastity Cage
That useless little sissy clit in your life need training. It's adjustable to keep it relevant to all stages of training that useless sissy. Locks in place and only can be opened with the key. The key comes with a necklace so that you can show the world you are in charge of his clit.
--
The night I purchased it I had a long day of training and was at my wit's end. After a particularly harsh spar with my torturer I finally after years landed a solid hit with my claws raking down his chest drawing blood in hand to hand combat. We stopped and his smile grew and I was chilled.
"Sally my favorite student after years of sparring you got a clean hit, not by luck but the skills I've been ingraining in you. I'm so proud and so sorry." We sparred again but I was thoroughly beaten into the ground more bruises then ever before as he picked up his skill lecturing me as he destroyed me.
I almost crawled into my room and my Sissy was there. All dressed up in a new Maid outfit that my mother made for me. My smile grew and energy filled me again.
"Welcome back, Mistress" He greeted, "How would you like me to serve you." That was the phrase I wanted to hear from him every time I entered the room. He needed to be dressed as a maid and welcome me back like a good sissy maid but not all defiance was out his tone was reluctant it had only been a week or so. I did not have the time with all my training and schooling to train it out of him. I frowned.
I am a failure at this point I have not done my duty to him and Beaten that pesky masculinity out. No more, No matter how tired I am I will spend time tonight and every night till he is a perfect sissy.
With new motivation, I grabbed his face and smiled. "The Greetings is not bad Sissy but you still have reluctance in your voice that's not okay, But that is a failure on my Part Sissy. No more though we will begin your new training regime tonight and every night after tonight" He frowned but I did not care as I let go of his face.
"You will go lay on my bed with your feet touching the floor facing away from me," I ordered and he stood still. I waited ten seconds and he did not follow with that stupid questioning face on. I was instantly pissed, I grabbed him by the face again my strength greater than his and pulled him to the bed throwing him onto it. I pulled his legs off the bed with his body still on. "Now I'm pissed Sissy not listening to your mistress deserves a punishment. I have been far to nice with you."
"I'm sorry mistress it will not happen again." He begged but half-heartedly I could tell he did not think anything bad would happen.
"No you are not sorry at least not yet you will not move unless I command it. Do you understand you stupid sissy?!" as I grabbed his neck pinning him to the bed showing my strength over him.
"Yes, Mistress" He choked out.
"Good, Move and the punishment will be worse." I walked over to my closet that I hid my previous spoils from the system. I grabbed the smallest beads the smallest plug and the flogger. I cleaned these regularly as I cleaned my room and kept them in good condition. I walked over with it in his blind spot so he did not see my stuff. I pulled off his panties he wore all day his erection popping out. I then threw his panties over his eyes.
"Now I'm extremely disappointed in you. You will be spanked at the start." His body now shivering but I saw his erection get harder. "Every time I spank you I expect a Thank you, MIstress, followed by the number If I do not hear that it will not count. I will spank you fifteen times. Do you understand me you, stupid sissy."
"Yes, Mistress," He meekly said trembling.
"Good," I grabbed my flogger and lifted him onto my lap legs on one side face almost to the ground on the other ass in perfect position as I lifted his skirt. As I lifted my flogger and brought it down on his ass a whistle sounded followed by a smack. Tears lept into his eyes as he groaned in pain.
"What are you suppose to say Sissy?"
"Thank you, Mistress, One"
"Good," It came down again.
"Thank you, Mistress, Two" he sobbed out. My smile was splitting my face as my flogger came down again.
"Thank you, Mistress, Three" he meekly sobbed barely audible.
"Louder Sissy or I will not count it," I commanded.
"Th-Thank you, Mistress, Three" He sobbed louder. I ruthlessly brought it down again and again on his redding buttcheeks. Pain coursing through him his dick twitching with each hit.
"Thank you, Mistress, Ten" He sobbed out as I brought it down again.
"Are you a sorry sissy now?" I asked.
"Yes mistress I am sorry" he sobbed out. I brought it down again.
"Did I say you could stop counting sissy." My pussy is damp as I punished this sissy.
"Thank you, Mistress, Eleven" he cried, again and again, I brought it down ruthlessly on his red rump.
"Thank you, Mistress, Fifteen" he was a mess his dick at full mast twitching tears a snot dripping on his face.
"Now you understand I am serious sissy. Do. Not. Take. My. Punishments. Lightly." I Lift him off my lap and take the tear-soaked panties off his face and lay him on his back.
"I won't mistress I won't Please forgive me Mistress, Please." he sobbed out.
"Now that the punishment is over sissy its time for the next step." He was lost in his own world sobbing. I lightly smacked his face to get his attention. "Now that you took your punishment properly you deserve a reward." I smile but he shivers and I lift his legs. "You will hold your legs Sissy and I will pleasure you tonight." The thought of me pleasuring him sent a thrill that showed on his face but curiosity about what I was going to do. I held his dick with one hand as I used my saliva to wet my finger. The pre-cum coming out of his dick from the spanking greased my hand not a fan but will do the job. I stroked him off slowly making sure not to give him too much pleasure to actually get off.
Then I start slowly messaging the rim of his anus before passing in earning me a gasp.
"Wha-"
"Shut up, Sissy" I commanded as I lightly gave him a handjob while fingering his asshole slowly pushing my middle finger deeper. I feel his dick twitch more and more often as I work my way deeper pre-cum coming out in greater volumes. He gasping and moaning from pleasure after so much pain. Right as he is about to ejaculate I let go of his dick and stop fingering him. Causing him to groan.
"Wh-Why you stop?" He asked looking at me like I just kicked a puppy. I gave him a murderous look. "Mistress, Why did you stop?"
"From now on Sissy, you must ask permission to Ejaculate if you don't receive permission you either don't cum or you will be punished do you understand, Sissy?" He looked pained and I gave a light slick to his balls getting a groan out of him and he nodded. "What's that sissy?" I flicked him again in the other testicle.
"Yes, Mistress I will ask permission." He groaned.
"Better." I simply say retreating my finger from his asshole but started lightly stroking him off again. I grabbed the anal beads as he was leaning back and stuck them in my mouth to lubricate them. Slowly as I gave him a handjob he lost in the pleasure sensitive as can be I started inserting the beads in his awaiting hole. The groan is audible as I inserted the smallest bead. Slowly inserting more until the seventh that I did not think he was ready for yet. The pre-cum was coming out in volume again he started asking.
"Mistress please let me cum." He asked expecting to be given permission.
"No," I said simply as I continued to jerk him off and now started to play with the beads popping one or two out and putting them back in.
"Mistress Please let me cum," He asked again this time emploring me.
"You will not cum yet till I have given permission Sissy," As I continued he was clearly holding it back now so again I let go dick.
"No, no, no, no Mistress Please" he was getting closer to begging as I regripped his dick playing again edging him closer to orgasm again. "Please Mistress let me cum," he begged clearly close to ejaculating. I did not even respond as I let go again just as he was about to cum. Followed by more groaning and sobs. When he came back down again I started playing with his dick faster and letting go faster until I heard genuine begging. " Please Mistress Please I Beg you Let me cum I need to. Please!" I let him come down one last time the started jacking him off hard.
"You may Cum sissy" as he was brought to the height I pointed his dick up at himself and pulled the beads out. He came hard and I let go immediately ruining his orgasm that he was in the midst of groaning lost in the pleasure and pain almost fainting spraying sperm all over his maid uniform and face. While he was lost I grabbed the bucket cleaning up his dick and around it before putting his now flaccid dick in confinement adjusting it for him to not be too small but not too much space. He didn't even notice as I snapped the lock into place. I smiled and grabbed the smallest butt plug I prepared and popped it into his ass filling what was a gaping hole.
Being filled again Derek woke up realizing his new gear. "Wh-what's that Mistress," He asked still lost as to what was happening.
"I Have seen fit to lock you up sissy," I took the key out of the lock that was left there and put it on the necklace wearing it visibly. "This is the key to unlock it your discretions have upset me you will keep your new toy in your asshole and I will be adding it to your inspection every morning and evening Sissy," I state simply
"B-But," He started to stammer and I simply held my hand to his lips with fresh precum on it. "Shut it Sissy you will not question my decisions now go clean yourself up and come back here dressed to sleep." I needed to comfort him his mind all over and it was the perfect time to grow his dependency on me. He meekly walked out of the room clearly not used to the plug with the way he was walking.
I smiled as I look at the system.
--
Name: Sally
Age: 10
Titles: Slave, Apprentice of Jack the Torturer, Martial Genius
Race: Beastkin - Phantom Snow Tiger
Level: 1
XP: 0
System Points: 6500
Mana: 1/1
Strength: 15
Agility: 35
Vitality: 18
Intellect: 43
Wisdom: 53
Luck: 10
Points to Spend: 0
Shop - Items Available
Inventory - unavailable
Lotto - No spins
--
I looked at it and a question lite my mind What? Where the extra points come from? I wonder where they came from is there any records, I thought.
--
Records of Points
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
+100 For training a Slave
-500 For Chastity Cage
-2000 For Tailoring
-2000 For Intellectual
-1000 For Whip Talent
-4000 For Mana Cultivation
--
That is convenient I guess. My Sissy came back in just his panties after cleaning himself up and stood before me. I could see ranges of emotions on his young face uncertainty being the largest. I changed into my nightwear in front of him like he didn't exist and crawled into bed as he continues to stand there.
"You may sleep with me tonight but no touching anything inappropriate." He nodded his head and crawled in with me I held him and he lightly sobbed thinking of tonight or maybe the cage I didn't care I listened to his sobs like music to my ears lulling me to sleep.