Sissified Ch. 08

This is the eighth story in the series, please read the previous chapters so as to understand the story better.

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The bell rang early in the morning, I got up. I was exhausted by the training from yesterday, but I had to go to Ms. Robin that's what the bell meant. I changed into my yoga clothes, a skimpy black G-string and a push-up bra. I went to the garden where we used to do yoga, it had been some time now since I had started, I loved my body now, it was flexible and well-toned. I did the yoga with ease as we finished Ms. Robin stopped me.

"I have to go and get some stuff, I will be back around 12." she said.

I came back to my room and took a shower and did my makeup. My nail had grown show I had to paint them again, I got into the oversized t-shirt I was supposed to wear at home, it exposed my ass and my penis, I felt slutty in it. I got into the bed and read the magazines Ms. Robin had left me, they were women's magazines, there were articles about latest fashion, how to seduce men and such, surprisingly I found it all interesting, before I knew it was 12 and Ms. Robin had returned. I went to the door to receive her, she got out of the car, she wasn't alone another man walked out of the car open the boot of the car and took out a huge cardboard box and walked into house. He started at me scanning me from top to bottom wit lust filled eyes.

"Who is he?" I thought.

Ms. Robin walked behind him with a couple of bags.

"I bought some new toys for you; Jack will install them in your room. While he does that why don't we go for a swim in the pool." she said and took out a bikini set from one of the bags. It was bright pink G-string bikini and the top was of the same color. We went to the pool, she asked me to wait, she got into a shower and changed into a green bikini, they were good looking and she looked amazing in them.

"Change into the bikini now," she said.

"Here in the open?" I asked.

"Is there a problem, it's not like I will be seeing anything new." she replied with a smile.

She was right, I removed the t-shirt and pulled the bikini up my smooth hairless legs, and put the top on.

"You look fabulous!" Ms. Robin exclaimed.

I blushed.

"Now let's get in the pool."

We stayed in the pool for some time then got out, I applied sunscreen lotion and lied on the recliner. After an hour Jack came to the pool.

"It's done." he said with a Spanish accent.

We went into my room to check, at first, I couldn't notice anything new. I moved around and noticed an electric cord near my bed I followed it to find a white thing which looked like a vibrator, I examined it, it had a timer on it I was confused.

"It's an alarm clock, as you might have guessed it goes into your pussy and it will vibrate to wake you up in the morning." Ms. Robin said.

I was shocked, I didn't need that I woke up every time she rang the bell.

"But mistress I don't need it, I wake up when you ring the bell." I said.

"Oh, about that you have to wake up before me from tomorrow, I will explain later. Let us move on to other toys." she replied.

I looked around in the corner of the room there were varieties of dildos on the floor and on the wall at knee height.

"They are for you anal training, you can use the ones on your floor to practice for cow girl style, and the ones on the wall for doggy style. They are removable they can pretty much used for any position." Ms. Robin explained.

There was a dildo installed on the chair in-front of the computer, I understood why didn't even ask her, there were bondage strains on all the 4 bedposts. She asked me to follow her to the bathroom, there she had installed a weird textured dildo.

"You will use this daily to clean your insides, I want you to be clean from inside too, and this is an enema, this will help you clean deep inside. Let's try it, remove your panties now." she said picking up a weird pipe.

Jack was standing with us how could I remove my panties in-front of him, but Ms. Robin didn't seem to care and before I could say anything she pulled my panties down. There I was standing bottomless in-front of a man I had met an hour ago, he stared at me. I could understand he was staring at me with eyes full of lust.

"Now bend over." Ms. Robin said.

I did, she pushed the head of the pipe into my ass, water started flowing from it and filled my insides, it kept on filling me after a minute or so I had a bump on my lower abdomen, I couldn't take any more water. Luckily Ms. Robin stopped the water and removed the pipe.

"Hold it inside, and don't you dare leak any of it before I say so." Ms. Robin ordered.

I stood there with a bump on my belly, bottomless my caged dick hanging out in the cold, jack staring at me with a smile on his lips, 10 mins had passed and Ms. Robin hadn't asked me to do anything, it was getting harder.

"Mistress I can't hold it anymore, please." I cried.

She looked at me.

"Go ahead let it out." she said.

I sat on the toilet and finally gave my sphincter rest, water flowed out from the deepest part of my ass, cleaning it. It somehow aroused me, I dripped a few beads of pre-cum, when it was over, we came back to my room, I wasn't allowed to wear the panties again.

"Ms. Robin what about the offer you told me about in the car?" Jack asked.

"Oh, that you can still take it if you want." Ms. Robin replied.

"Absolutely." he said walking towards me. He stopped in-front of me and pushed me to my knees and pulled down his trousers to expose his massive dick. I couldn't understand, I looked at Ms. Robin.

"It has been quite some time you have pleasured a real dick. I didn't want you losing your touch so Jack here has agreed to help you, now get on with it show him how thankful you are." Ms. Robin explained.

I grabbed his dick and kissed his tip and his inner thighs, it was a solid 9-inches in length when it was not hard, I started jerking him slowly, its size increased to 12-inches. I kissed it again and sucked on his balls, I moved my tongue around the head and slowly licked down to the base. I sucked the tip while continuing to lick it, I went deeper and deeper with every suck, I deep throated him. I went deeper till his balls slapped against my face, I looked at him his head was up and eyes closed, I started caressing his balls and continued sucking him while moving my tongue around his dick. He started twitching.

"I'm cumming, I'm cumming." he shouted and came into my mouth.

It has been days since I had someone else's cum, I loved the taste. I swallowed it.

"You did good, Chica completely worth it." Jack said and handed Ms. Robin some cash and left.

I looked at her.

"I feel like a slut mistress, I didn't want to do it for money." I said.

"Oh silly, I'm trying to make you a sissy slut and you are progressing so well, and it's not time you received money for doing such things and you also have a debt to repay me. Now go clean up and meet me in my room I have got some new stuff for you." she said.

I went back to my room and brushed to remove the taste of cock from my mouth, then took a bath and dressed up in an oversized pink T-shirt. I went to her room. She sitting on her bed with a lot of bags.

"You still have a huge debt to repay me, I want to help you do so. So, I have asked to maid to stop coming and you will be doing her chores instead, you need to dress accordingly." she explained.

She pulled out a pair of black nylon stockings from the bag and asked me to sit beside her she showed me how to wear them and then asked me to do it. I folded it and put it on my feet then slowly I rolled then up my legs, I loved how they felt on my hairless legs. I repeated it with my other leg. She pulled up a garter belt up to my waist and taught me how to Attach them to my stockings, it was the color as my stockings, then she handed me matching bra and panty, I put them on. From another bag she took out a French maid uniform, she asked me to wear it, it was short in length it ended around 2-inches below the waist and its top was a deep cut design and exposed most of my bra. Finally, she put a maid headgear on me and gave me an 8-inch black heels. I looked in the mirror, I looked like a slutty maid from the porn movies I used to watch.

"You need to wear them every morning and do the chores around the house, you have to clean the house, wash the clothes and cook the food, you need to do all these before I wake up. I will send some videos to help you learn them. Now go back to your room and watch them, we will meet in the evening." she said.

I went back to my room and sat on the chair I pulled my ass cheeks apart and slid the dildo on the chair inside me, I started vibrating automatically. I was distracting, I started the watching the videos. They covered all the lessons how to clean, wash clothes and cook. I tried learning them, this went on for the whole afternoon. Ms. Robin rang the bell again in the evening, I went to her room.

"You have learnt how to look like a woman, but to be the perfect sissy you must learn how to behave like one, I will teach you." she said.

She taught me all about being a woman. She taught me how to walk like one, how to talk like how, how to laugh, how to approach a guy, show to sit, the lessons went on the whole evening. I went back to my room when they were over. I looked at the alarm dildo it was set at 4 in the morning. I changed into a nightie and pushed the dildo inside me and went to sleep.

It vibrated exactly at 4 in the morning, I got up I was aroused due to the vibrations, I got into my maid uniform and started the chores, I had previously done these for Mom, she gave me money to do these, I easily cleaned the house and then washed the clothes, I put outer clothes in the washing machine and cleaned the lingerie with hand, Ms. Robin had such beautiful lingerie I thought while washing them, I went to the kitchen and started cooking breakfast. Just around the time I had done all these Ms. Robin woke up.

"You have done a wonderful job." she said still in her nightie.

It was a transparent one and her body looked so hot, she was beautiful in, my previous self would have wanted to fuck her, but now it was a distant thought now only cocks and anal pounding turned me on. She sat down on the dining table and ate the eggs and bacon I had made.

"You are a wonderful cook, looks like I have made the right decision, I have bought an online cooking course for you learn from it, now go do your anal training." she said.

I was tired all these chores had taken a toll on my body, but I obeyed her, I went to my room and changed into a T-shirt and went to the dildos installed on the wall pushed my ass against it and pounded on it till my hole was all loosened up, then I got on my toes and pushed the dildo on the floor up my hole, I bounced up and down on it, my calves were hurting, I continued for some time then gave up. I was so tired but there was no time to rest, I got back on the computer and slid the dildo on my chair up my ass with ease, it starts vibrating, I watched the cooking videos and made notes. Then I put on the maid dress again and cooked lunch, I tried I recipe I had learnt from the videos. I had some time to rest now it was 2 P.M and my training started at 5. I fell asleep instantly. I went to Ms. Robin's room in s short dress as she had ordered me to wear one while coming for training, my female studies from yesterday continued. After the classes I again had to change into the maid dress and cook dinner, then finally I went to sleep.

This was my routine for the following two weeks. I woke up at 4 just like I had done for the last two weeks with a vibrator up my ass, I cleaned the house and washed the clothes I had gotten better at it. I cooked breakfast and prepared the table for Ms. Robin. She woke up and came to have her breakfast. She ate it.

"You are a wonderful cook and see how good you have done the chores. I think it's time." she said.

"Time for what Mistress?" I asked.

"Time for your evaluation as a maid, I will invite some friends over and you will serve us as a maid, and they will evaluate you, do your best if they don't like your I will punish you severely." she said.

"Yes, mistress." I replied.

"Now go and do your training, I have to buy a new outfit for you." she said and left.

I was really horrified about the guests.

"Who are they, what if the know me?" I thought to myself.

I went to my room and did my anal training by now I had gotten to the biggest one and I still did yoga on alternate days so my body was flexible as before, I finished it and got back to cook lunch. I then got into the bed and dozed off, it was around 4 I heard the bell in my room ring, Ms. Robin had returned and wanted me in her room, I went to her room. She was standing with a bag in her hand, I went to her, she handed mw the bag.

"It's your new maid uniform, go on try it on." Ms. Robin said.

I opened the bag I pulled out a black maid skirt and a blouse with the same color and pattern and a headgear, there also a garter belt with stockings. I stripped and put them on, the top ended just below my chest and the skirt started at my waist and was around 6-inches in length, they both has the black color and white embroidery just like my previous uniform, I put on the garter and stockings next and the heels. I looked at myself in the mirror I looked like a slut, just dressed like a maid.

"You look absolutely perfect." Ms. Robin said.

"But mistress I'm not wearing any panties." I told her.

"You don't need them, I have another item for you to wear today." she said pulling out a butt plug from the bag. It was rubbery and black in color, she pulled it out and I noticed it had a tube attached to it, with a pump at the end, she put lube on it and asked me to turn around. She pulled out my butt-plug and shoved this in. she gave it 5 pumps; I could feel it increasing in size.

"It should fit you perfectly now, my guests may give you more pumps if they are pleased with you, but if you don't receive enough pumps, you will be punished do you understand?"

"Yes, mistress." I replied.

"Good now go and prepare some drinks and snacks for them, they will be here at 7."

I went to the kitchen and got to work, after I finished cooking, I went to the living room and cleaned it. I went back to the kitchen and waited for them to arrive. Around 7 I heard the bell ring, Ms. Robin had ordered me not to come out of the kitchen till she called me, I stayed in the kitchen. Ms. Robin opened the door, I could hear them enter, they were 3 other people and their voices sounded somewhat familiar. I couldn't recognize them. They sat there and chatted for some time.

"Where is the maid you told us about?" a voice asked.

"Oh, yes you will love her. Bring the wine sissy." she shouted.

I went out holding a tray of wine glasses in my hands, I walked putting one feet in-front of another swaying my hips with every step, just the way Ms. Robin had taught me. I stopped and looked at them, I was filled with shock, I stood there staring at them, Ms. Jen, Ms. Renee and Ms. Alex. They were all my school teachers and all were beautiful, I stood there stiff with fear.

"She is lovely, but I know her from somewhere." Ms. Alex said.

"Me too." Ms. Jen and Ms. Renee said together.

"Look at him you all know him he is a student at our school." Ms. Robin told them.

They stared at me trying to guess who I was.

"Is it the skinny kid, the one who failed at every subject. I can't remember his name." Ms. Jen spoke.

"You mean Ron?" Ms. Renee said.

Ms. Alex looked at me.

"Yeah, it is Ron." she said.

I shook with fear now my teachers knew what I had become, what if they tod this in school what will happen then.

"She looks absolutely beautiful, the way she walked no one could have guessed he was the sloth, Ron." Ms. Jen said.

"You did a lovely job with him." Ms. Renee said.

"What inside his dress and is he completely dressed like a sissy should?" Ms. Alex asked.

"Turn around Sissy." Ms. Robin ordered.

I did.

"Nice dress." Ms. Alex commented.

"Now lift your skirt." Ms. Robin said.

I put the tray on the table and lifted my skirt. They all gasped.

"You made the right choice sissy, look at the size of his clitty, you were never a man you never would have pleased any lady, its good you became a sissy now at least you can serve others." Ms. Alex said.

"Now serve them the wine." Ms. Robin said.

I lifted the tray and went to Ms. Renee first, she was Mexican woman with heavy breasts and beautiful brown skin. She picked up a glass.

"You can see she has a pump hanging from her, if you are pleased with her service, please give her a pump." Ms. Robin said.

Ms. Renee after hearing this gave me 2 pumps. I went to Ms. Jen next she was an Asian with the perfect proportions she could have been a model if she wanted. She picked up a glass and gave me 2 pumps.

Ms. Alex was the most beautiful out of them she had a tanned skin just to the right color, she wore a black short dress, she had 32DD breasts had a perfect ass to match that. She picked up a glass and gave me 3 pumps.

"You did a good job, the way you walk the way you serve, you have been trained well." she said.

They drank the wine chatting, Ms. Robin told them all about my adventures, how she had caught me watching sissy porn then had offered to help me, how she made me masturbate in the park and then sent me whoring in the park, she told them about the tattoo.

"I didn't notice it. Can you pull up your skirt." Ms. Jen said. I pulled up my skirt.

"It's beautiful, suits her." she said.

"I also noticed the belly piercing, looks good on her." Ms. Renee said.

"You should get her nipples pierced, it will suit her too." Ms. Alex said.

"I have had that in my mind for some-time, I will think about it." Ms. Robin said.

"I'm getting hungry." Ms. Jen said.

"Well, my sissy here is a really good cook, she has prepared snacks for us." Ms. Robin informed them.

I went to the kitchen and plated the pasta I had made for them. I came back to the room and served them. They all liked it and gave me a pump each, now it was getting unbearable, the plug has gotten so big, it was straining against my insides.

"What else can she do?" asked Ms. Alex.

"She can make you cum like you have never before." Ms. Robin said. I felt proud.

"Let us see, get down here." Ms. Alex said.

I kneeled in front of her. Lifted her foot and kissed it, then I sucked each of her toes, I repeated the same with other feet. I slowly lifted her dress and pulled her panties down. I licked her clitoris making round movements with my tongue, then I moved to her vagina, I switched from her vagina and perineum, I could guess she was enjoying it based on her moans, they got stronger and stronger and she came hard, I licked it all up, I licked her pussy clean.

"You weren't lying, it was a really strong orgasm." Ms. Alex said, and gave me 3 pumps.

"I want one too." Ms. Renee said. I got to her and did my magic and when I was done with her, she was panting hard she had come really hard.

"I loved it." She said breathlessly. She gave me 3 pumps.

Ms. Jen called me next, she wanted me to do her ass. I licked her toes and then she pushed her ass in my face it was so beautiful she had such a shapely ass, I licked the hole in circles with my tongue and then pushed my tongue inside her ass, I went in deep hitting her G-spot through her ass, I fingered her clitoris simultaneously, she moaned loudly.

"Oh my......God, oh My Gooood, I'm cumming." she screamed and came hard on me, I licked her pussy clean, I got up I looked at them all of them looked exhausted. Ms. Robin hugged me.