Sissified Ch. 04

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

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I wanted to become more feminine, more pretty. This was the only thought on my mind as images of beautiful sisses and big dicks flashed before my eyes. I listened to them talk about how much they loved their transformation, their girly clothes. I soaked it all up. I wanted to suck dicks just like them. When the video ended, I realized I was leaking. I instinctively started masturbating the way Ms. Robin had taught me, I rubbed the head of my penis with two fingers. This was the only way I could stimulate my penis, I tried jerking it but it didn't even get hard, but only after a few seconds of rubbing it with my fingers I started feeling waves of pleasure. I came hard in my panties. I removed them and licked my cum off it. Just then I realized I was still on a videocall with Ms. Robin. She was smiling.

"Did you like it sissy?" she asked.

"Yes, mistress I loved the video," I replied.

"Anyway, sissy you must learn to control yourself, a sissy's job is to give pleasure not receive I send you these videos so that you can learn not to pleasure you, from now on only masturbate with my permission," she said.

"But mistress."

"No buts you must follow my every order or else I won't be able to help you, ok then I will see you in the evening," she said and cut the call.

I changed into another cotton panty and put on the white crop top with sissy printed over it and the red shorts, I felt exposed in those the top ended just below my chest and the shorts ended only 4 inches below my waist but once I looked at the mirror, I forgot everything. I had such smooth and hairless skin and face looked so beautiful and pixie hairstyle was amazing I looked so feminine. I got hard instantly, I remembered Ms. Robin's orders and decided not to masturbate, I lied on my bed thinking what had been happening with me, I got caught watching sissy porn by Ms. Robin, she made me wear panties and I sent her my photos in them, when she learnt I was wearing Mom's panties she punished me and made me lick my cum, then she took me shopping and humiliated me by making me tryout different panties and then waxed my body completely from below my eyebrows, even did skin treatments to make my skin more feminine got my hairstyle changed. Then got me crop tops and shorts for home and skirts and t-shirts and dresses to wear while going out, nighties and baby dolls to wear while sleeping and shoes to go with them.

It was 6:45 at this time and I was still horny, Ms. Robin will be coming at 7 and I couldn't have a boner then, I started masturbating thinking about the humiliation while trying panties in public and it somehow turned me on and came in my panties just then the doorbell rang, I wiped my hands and ran to the door and opened it, Ms. Robin came in.

"Very good sissy you are wearing your feminine clothes, you look lovely in them."

We went to my room.

"We must not forget your studies, we will study for an hour and then I will help you in your training," she said.

We sat down to study and she was such a good teacher I understood almost everything she taught me we finished the chapter quickly and my training started, she asked me to bring my heels and makeup kit, she made me wear the red short dress she bought me, when I removed the clothes, I was wearing, she spotted the wet spots in my panties.

"What is that sissy?" she asked.

I went to her she dabbed her finger on the spot and smelled it bought the finger to my face and put it my mouth and ordered to me to lick it.

"You have been playing sissy, and you didn't follow my orders," she said emotionlessly

I stood there sucking her finger.

"I didn't want to do this but you leave me no choice, I thought you could be trusted but I wrong," she said. She opened her bag and pulled out a box.

I had seen something like that in the videos.

"Is it a chastity?" I asked.

"No, sissy it isn't a chastity but did you want one?" she asked smiling.

I was relived, but if it wasn't a chastity what was it. She opened it, it was a camera and an expensive one.

"I will be installing it in your room so that I can keep an eye on you, and check if you are following my instructions," she said.

I stood there shocked, she got up and installed it in a corner of my room so that the room is completely visible.

"Now change into the dress," she said.

I changed into the dress, she then taught me how to put makeup she put it on for me and I observed carefully, she told me to do it every morning and she will send some videos to help me with it. Then I put on the red heels, I struggled walking in them at first them I got the hang of it. She stood up to leave. I kneeled and kissed her shoes and said goodbye.

"Good sissy, remember I'm watching you and follow the instructions," she said and left.

I went to the mirror and looked at myself I looked hot, the red dress, makeup, heels and the smooth skin made me look like a total babe, if I didn't have a flat chest no one would have even thought I was a boy. I felt horny again, I was feeling at my own feminization what had happened to me, thought of masturbating but then remembered the camera and decided not to. I looked at the clock Mom would be home in some time I changed into boy clothes with long sleeves and wore a full jogger so that it would cover my hairless body, I removed the make up and took the packet Ms. Robin had asked me to give to mom downstairs and waited for her. She came home after some time.

"Love your new look Ron, the hairstyle really suits your face and did you do something to you face?" she asked.

"Yeah, I got a facial today," I tried lying.

"Yes, that explains it. It looks so much better now."

"Thank you, mom. Ms. Robin asked me to give this to you," I said giving her the packet.

She opened it and took a paper out of it and read, and looked at me smiling.

"She is such a good teacher, she told me she took you to a psychologist today to help you concentrate better. This is the prescription," she said holding out the paper. She handed me a bottle of pills they didn't have any labels.

"These will help you concentrate take them 3 times a day, and these are to be mixed with your food, they are multivitamins," she said pointing to a bottle of transparent liquid.

"I tried asking her the bill but she denied, she said she wants to help you, such a noble soul she is," Mom continued.

I couldn't understand how did I get a prescription without going to any doctor but knowing what Ms. Robin could do so I didn't say anything. We had dinner and she mixed the liquid with my food; it didn't taste any different. I went to my room, and tried to sleep.

I received a call from Ms. Robin.

"You are about to break another rule," she said.

"What mistress?" I asked.

"First you didn't take the pill, do it now."

I took the pill.

"Now you forgot to change into a nightie, try it on you will love it," she said.

I stripped and got into the transparent black one, my body was clearly visible while wearing it and Ms. Robin had asked me not to wear anything under it, so my small penis was visible beneath it, it was so humiliating I got a asking me to pose in-front of the camera I did.

"Your clitty looks so cute sissy," Ms. Robin texted.

"Thank you, mistress."

"Now go to sleep and don't masturbate."

I went to bed, I loved sleeping in a nightie suddenly I felt horny but didn't get hard I didn't understand what was happening I panicked and called Ms. Robin, and told her what was happening, she told me those were the side-effect of the pills and they weren't permanent and gave me permission to try getting my penis hard in the morning if I didn't believe her and cut the call.

I tried sleeping and fell asleep after some time again I had the dream, me on my knees only this time I was wearing a transparent nightie and nothing underneath it, I was sucking on a big cock, my body was hairless and nails were painted I had long hair and slutty makeup, after sometime he came in my mouth and I swallowed the cum. There was a knock at my door it was mom I pulled the blanket up to my chin.

"Come in," I said. Mom came in.

"Good morning darling, I'm leaving early today I had made the food eat it and don't forget your pills and Ms. Robin called she is taking you to gym with her she said a healthy body is required for a healthy mind I couldn't agree more with her she cares for you so much you are lucky to have a teacher like her. Bye," she said and left.

I removed blanket saw my nightie was wet with pre cum, I couldn't let it go to waste so I licked it clean. I thought of checking if I could hard so it started rubbing it and I received a call from Ms. Robin.

"So, you don't believe me go ahead check but remember you can't cum and don't cut the call," she said.

I started rubbing it took some time to get it hard I continued rubbing it for some time I got hard and I was about to cum.

"Stop," Ms. Robin shouted, I removed my hand from my penis precum leaked on continuously.

"See it still gets hard, next time trust me now eat your breakfast and take your pill and wear a crop top and shorts and the sneaker I got you yesterday and meet me downstairs in 30 mins," she said and cut the call.

I was horny I wanted to cum but Ms. Robin was watching, I got up took a shower put my clothes in the washing machine I had to clean and dry them before Mom came home I couldn't let her see them, I dressed up in on one of the only two crop tops that didn't have sissy or slut printed over them, it was red and it was really small, I opened my underwear drawer and I felt excited looking at the choices I had I took a blue cotton panty and wore it and then wore a black shorts over it, put on my pink sneakers, tried applying makeup by see the videos Ms. Robin had sent me and headed downstairs, ate my breakfast which I was sure was mixed with the liquid Ms. Robin had given, then I heard Ms. Robin's car horn and went outside, it was 9 and I prayed that my neighbors didn't see me. I ran to the car and got into it, she looked at me.

"You look cute and the make-up is really good considering it was your first time," she said and fixed my make up a little then we drove to the gym.

We went inside, Ms. Robin signed me up the receptionist looked at me when I gave my name as Ron but didn't say anything he signed me up and gave me card, it was weird it was my first time leaving my house dressed as a girl and coming to public place like the gym was humiliating but I had to obey Ms. Robin she was trying to help me I thought.

We went inside.

"So this is Ron," I heard someone saying.

I turned it was beautiful woman in a black sports bra and grey shorts her figure was perfect you could understand just by looking at her that she worked out frequently. She walked towards us.

"Hey Robin I see his training is going well, don't worry I will get him in shape," she said looking at me.

"Ron this is Jessie, she is the trainer here, she will be training you obey her. She will be giving me weekly reports don't miss gym without my permission, now tell her you will obey her and thank her for training you," Ms. Robin said.

"I will obey you completely and thank you for training me," I said to Jessie.

"I think I have made it clear for a sissy like you every woman is a mistress, now would you like to correct yourself," Ms. Robin said.

"Thank you, mistress," I said to Jessie.

"You're so cute, I will love to train you, now let's get to it," Jessie said.

She guided me to the treadmill, she asked to run for 45 min I was already exhausted after doing it then she made me do squats and crunches I was exhausted, I saw men training their arms.

"Will I be lifting those dumbbells?" I asked Jessie. She looked at me and smiled.

"Look in the mirror she said, do you look like a man?" She asked.

I looked at the mirror and saw how feminine I looked, I looked down and didn't reply.

"So, you realize you are sissy accept it you need to look more girly so I made you run to tone your body, squats will help you get lady like legs and shapely ass, and crunches will help you get a flat belly. Now do you understand?" Jessie asked.

I didn't reply I couldn't understand I was training to look like a girl I mean l liked looking girly but something like this where my body shape will be changing made me scared. Jessie noticed this.

"Do you think I'm beautiful?" she asked.

"Yes mistress," I replied there was nothing to think about it.

"Then trust me and you will become beautiful too."

At first, I got scared hearing this how can I change my body to something that girly but my confusion cleared away I wanted it.

"I want to become like you mistress," I replied.

"Wow that was quick looks like the videos Robin told me about really do work, anyway it's nice you decided. That's all for today see you tomorrow, and wear only feminine clothes to gym Robin's orders, bye."

I walked out and didn't see Ms. Robin I understood I had to walk home, I was so exhausted I could barely walk at all it took me 20 mins to reach home it wasn't that far, I rushed into my house hoping no one saw me, I took a bath again and washed the gym clothes, I put all the clothes to dry and went to my room. I put on a cotton panty, a crop top with slut printed on it and a blue short and lied down on my bed, I received a message from Ms. Robin saying she had sent another video and I had to watch it before class, I didn't need to facetime her as she had live feed from the camera.

"Today I want you to watch it while dressed up and as you are not allowed to cum you have to lock your hands behind you, I have left a handcuff in your drawer put in on after playing the video and I will open it from my phone when the video ends," Ms. Robin said.

I found the handcuffs I put on my headphones played the video titled "Fit and submissive sissy" and moved my hands behind my back and clicked the handcuff shut. It started playing a hot girl came and started saying how important it was to exercise and be fit for looking beautiful, I listened to her she started stripping turns out she was a guy but had such great curves she said anyone who works had can get beautiful like her she started running on a treadmill nude her small penis jumped from side to side it was still bigger than mine though, then suddenly I started hearing words they said look feminine become beautiful train in a hypnotic voice I got into a trance images of guys with big dicks saying they loved to fuck a fit sissy started flashing nude sissies with fit bodies started flashing I got sucked into I wanted to become like them, then videos started playing sissies sucking oh cocks of muscular men I wanted that too, I thought. Then it changed to sissy kneeling before his mistress licking her feet "you must obey every command, never question mistress do whatever she says, she is perfect obey her." voices started saying, the video played on for some time when it ended, I felt myself leaking precum I was horny but my hands were locked I waited for Ms. Robin to open them, the thought of getting fit lingered on my mind, my handcuffs clicked open.

"I know you are horny but don't masturbate otherwise you will be punished and go take you pill now," she texted.

I was really horny I hadn't cum in two days and was horny as hell, I thought of going out of the room and masturbating but I couldn't get myself to Ms. Robin I gave up on masturbating I had my lunch and took the pill and got into bed for a nap, my mind was not working correct I was too horny to think usually I masturbated when I was horny but now I wasn't allowed so I was not thinking properly, I got another text saying I had to watch another video, I put my headphones on and locked my hands it was video about sissies sucking huge dicks and rubbing their own penis and Cumming, I couldn't think straight I had to cum I started drooling thinking about dicks, after the video ended and my handcuffs were opened.

" I have to cum mistress please I'm going crazy," I texted Ms. Robin.

"Ok you can but you have to do a few things first a packet will be delivered to you now. I want you to receive it in panties, the G-string panty and the black fishnet crop top, go out of the door till the road to the delivery boy and get it from him and wear it and wait for further instructions," she texted.

I was scared going out of my house in only panties and the slutty transparent crop top and letting the delivery boy watch me in them. I got scared just by thinking it, but somehow, I felt excited I wanted to show my feminine side to everyone, I didn't know where this was coming from but I wanted to do it. May be me being horny led me to do this. I changed into neon G-string it was so small it tightly covered my penis almost outlining it and its string went between my ass exposing my ass completely, then I put on the fishnet crop top It was completely transparent my nipples poked out of the gaps I was almost naked I corrected my makeup, if I'm doing it lets do it perfectly, I thought to myself. I looked out and there was the delivery boy I ran down opened the door and walked towards him. I felt humiliated, some of the people walking on the street looked at me. Boys were looking at me with lustful eyes, slowly I went to the delivery boy took the parcel and turned around to go back inside, I felt him looking at my ass and I swayed it like a slut, went inside my house and closed it. I fell to my knees and started leaking I was turned on by exposing myself I thought. I looked at myself I looked like a flat chested slut with the neon panty, makeup and how did I have the guts to go out looking like this, and on top of that enjoy it. I was leaking continuously now, I looked at the packet. I need to wear it then I can cum I thought and rushed to my room, I opened it was a pink frilly transparent one-piece lingerie, I was excited to see it. I saw a tutorial on internet and followed the instructions and wore it, there was a heart shaped hole between the legs and my small penis hanged down through it.

"Now sit in front of your computer and handcuff yourself," Ms. Robin texted.

I sat and locked my hands behind my back, suddenly the last video started playing and it played for hours on a loop I looked at sissies sucking dick while rubbing themselves for hours, I was horny beyond imagination, it was 7:30 P.M when they stopped and my hands were unlocked, I had a pool of precum beneath me. Ms. Robin called.

"I will be at your house in 30min don't masturbate and lick the cum if you want and take your pill, don't masturbate understand," she said and cut the call.

I jumped to my knees and started licking the cum there was so much and it was heavenly, I wanted to masturbate but I couldn't get myself to disobey Ms. Robin, I took the pill and waited for her.

"Come to the car, in what you are wearing and wear the heels," she texted.

My mind was blank I was too horny to think anything I walked to the car as fast as I could in the heels leaking all the way.

"Someone's excited!", she exclaimed slapping my leaking penis.

I got even more excited; this was the first time a woman had touched my penis and a beautiful one at that but I still didn't get hard, must be the pills I thought. We drove to the park. She parked in front of the gate she gave me an earphone and a packet, she said she would be giving instructions through the earphone, she asked me to get out of the car. When I didn't, she pushed me out. There I was on the street in a transparent crotchless lingerie with my penis hanging out in cold leaking in front of a park, she drove away.

"Go to the bench in front of you," she said through the earphone.

I walked to the bench in the park, not making any sound as homeless people slept in the park and didn't want to wake them up.