This is the sixth story in the series, please read the previous chapters so as to understand the story better.
I got up as usual, I had to go to gym I had my breakfast and my pill, then I went to get dressed I realized I had no clean panties left, I had forgot to clean them, but I had to go to gym and all my gym shorts were semi-transparent but I couldn't make Ms. Robin angry, I decided to wear the wear the new one which was the only one which was not transparent, I put it on and put on a red sports bra and left for the gym, I got in and went to Jessie.
"Someone is being bold today, let's do the warmups," she said.
I couldn't understand what was bold about me today. I stretched and used the treadmill, it felt different with the plug in my ass, I noticed some boys were passing by me and looking at my ass. I felt good I had spent hours in the gym trying to get the shape. I completed my exercises, before I left, I went to the mirror to see my body, I realized the reason why I was getting special attention today, the diamond on my butt-plug was completely visible and my shorts were semi-transparent, they just didn't look like that as my room was dark and there was so much light here. To make it even worse my chastity was quite visible, I got red with shame and quickly left the gym, people stared at my ass all the way home. I got a call from Ms. Robin.
"Someone is being slutty today," Ms. Robin said.
"I didn't know mistress; I didn't know they were see-through."
"Oh, my cute sissy, you are such a slut. You are just perfect, don't forget I'm coming in the afternoon today," she said and cut the call.
I changed and washed my clothes a dried then I also cleaned all my lingerie, before Ms. Robin arrived, I had cleaned and put them in my wardrobe, Ms. Robin arrived.
"Let's see what you have learnt, what are sisses for?" she asked.
"To give pleasure," I replied.
"Good, today I will teach you how to give pleasure," she said taking out something from a packet. It was a large black dildo bigger than the one I already had, she stripped to her underwear, put the dildo in some kind of belt, she looked so hot in her underwear. She tied the belt around her waist.
"Now I have seen you have progressed quite a lot in your oral skills, show them to me."
I crawled towards her and started stroking it, the I kissed the tip and started sucking it slowly and slowly I went in deeper till the complete dildo was inside my mouth.
"You're good but you are forgetting the balls, fondle them with your hand", Ms. Robin said
I gently grabbed the balls and played with them while sucking the dildo, after sometime Ms. Robin asked me to stop.
"You're a natural, as if you were born to be a sissy, I'm so proud of you, you are so close to becoming a perfect sissy," she said proudly.
I felt happy hearing these the faster I became a sissy the faster I could start reversing it, it was an absurd theory but I trusted Ms. Robin.
"Thank you, mistress," I said in a broken voice. I voice had starts changing too, when I asked Ms. Robin, she said it was common she called it a second puberty.
"I'm so happy I will give you a present, get ready and wear the strapless golden short dress you have, wear it with the black heels, put on makeup quickly now," Ms. Robin said.
I got ready, I looked beautiful all the exercises and toned my hips, legs and ass, my belly was completely flat my hair had grown longer and it looked like as if my chest was a bit swollen.
"Had I grown boobs?" I thought.
"No, it must be the dress". We got in her car and drove to a salon it looked expensive.
We got in.
"I have an appointment for manicure and pedicure for two," Ms. Robin said.
We went inside, two ladies came and cleaned my hands and feet, they shaped my finger nails and toe nails, they looked so beautiful, my hands and feet were looking so beautiful and they were so soft, I loved it.
"Which color nail polish would you like?" she asked.
"Give her a pink nail polish," Ms. Robin said her.
She painted my nails in pink and they looked so pretty, my hands and legs looked so feminine.
As we left Ms. Robin bought me couple of nail polish and a remover.
"Always wear nail polish," she ordered. I nodded.
It was evening by now, and she was taking me some other place.
"Now let's see how you do with the real thing," she said.
I couldn't understand but kept quiet, she stopped near a building it looked like a bar. We got out of the car and got into the bar, it was filled with people men and women who looked like prostitutes looking for customers, we went straight to the ladies' room, she asked me to get into the cabin in the corner, it had a hole in the wall.
"Get on your knees, sissy and knock the wall," she ordered.
I didn't understand but followed her orders, once I did a dick appeared through the hole. I looked at it.
"What are you waiting for, do what you have learnt," Ms. Robin said.
"But mistress it's a real one."
"So, what you are to give pleasure, give it to him suck it."
Tears started welling up in my eyes, I couldn't do it.
"Don't cry it's your choice just look at it if you want to do it, do it otherwise we can leave," she said.
I looked at it, it was so big just like my dreams, me on my knees dressed all feminine sucking on a dick I could feel my penis getting hard, it strained against the chastity, without thinking I grabbed it with my hand and started stroking it, it got hard. It was beautiful nothing like the dildo I could feel it growing, the blood pumping into it, the warmth. I gently kissed the tip, and then the balls, precum oozed out of it, it was delicious I wanted more, I started sucking it, with my other hand I gently caressed the balls. I was so turned on that I started leaking, I kept sucking on it.
"You're such a slut getting turned on by giving blowjob, just as I expected," Ms. Robin said.
I looked at she was smiling she looked satisfied as if she knew this was going to happen. I ignored her, I wanted to enjoy it completely, I was so excited while sucking it that I kept leaking continuously, after sometime the dick started twitching, I understood he was about to cum. Before I could pull it out, he came into my mouth and then on my clothes, this was the first time I had someone else's cum in my mouth, it tasted different than mine, it was better. I savored it kept it in my mouth for a while then swallowed it, a 20$ bill came through the hole.
"Looks like he was happy and decided to tip you give it to me, it's time you started paying for all the clothes, treatments and other things I got you," Ms. Robin said and took the money.
We came out of the bathroom my clothes were covered in cum my makeup was ruined I felt humiliated walking out of the bar, we got into the car.
"You did good for your first time, now you can come here if you ever crave cock," she said and winked.
She drove me home.
"You may remove the nail polish if you don't want your mother to see but you have to apply them again before you go to the gym tomorrow and watch the videos, I send you," she said and left.
I got into my house, I was already missing the feeling of cock in my mouth, I changed into a nightie as I knew mom would return late and leave early, I had barely seen her in 3 days, I didn't bother removing the nail polish it looked so perfect, I played the video. There were sissies sucking a dick with limp penis, the words played in the background.
" A sissy must be feminine, she must be submissive, she must never get hard, she will never decline a dick, her clitty will always be soft and limp, she must wear a chastity, she must have a butt plug to keep her boipussy ready". I repeated it after the voice. When it was over my penis was completely limp but I was horny, so I grabbed my dildo and sucked on it till I fell asleep. The images of my sucking a dick came in my dreams, I enjoyed it.
It had been 40 days since I started taking the pills and 20 days since I had started wearing the chastity and butt plug, I wasn't allowed to cum even once, Ms. Robin kept me horny all the time, she had flooded me with hypnosis videos, with regular trips to the glory hole, all these made me horny, I had been constantly horny, my body had also started to change from all the exercises, I now had a complete bubble butt, I also had small boobs growing and my nipples had become somewhat bigger, if only I had boobs I would look like a complete girl, my hair had grown to shoulder length and I had changed my hairstyle to a stylish bob cut. I was naturally blonde and it looked so pretty, my voice had changed and almost sounded like a girl, so I had to change my voice when I talked to Mom, my skin was more smoother than ever. I liked everything about my body, I loved it.
I woke up, had my breakfast took the pill and went to the gym, I came home took a bath, then get got dressed up as girly I could, put on make-up and then painted my nails; this had become my daily routine, I had become an expert in all these, I had learnt to combine clothes according to color, what on wear on what occasions. My make-up and nail painting skills were impeccable, I had learnt to walk in the hells and they felt completely natural to me, regular trips to the glory hole and oral training from Ms. Robin had made my cock-sucking skills really good, overall, I had become a complete sissy. I loved it I wanted everyone to know about me the thought turned me on, but I was still scared, I kept it a secret. It was really difficult to hide it from Mom, I rarely saw her now due to her promotion, but when I did, I wore full sleeves and full pants to hide what my body had become from Mom. Ms. Robin had complete control over me she had my pictures and videos, she had camera installed in my room and my bathroom, my chastity key was with her and she made me give her a copy of the house keys, but it was alright she was my mistress and she did all this to help me.
I got back from the bathroom, opened my wardrobe it had all type of female clothes, they were thrice the amount of boy clothes I had. I slipped a panty with the word "Sissy" on the ass, and put on a blue crop top, and a black short and got ready to study. Ms. Robin made sure I studied, even after her helping me in my transformation she made sure I studied so that I could complete high-school, it was a lot of homework. I finished it and started watching the video Ms. Robin has sent me, it was simple video with instruction of what a good sissy should be like, I already had learnt them by heart.
"A sissy has only one goal to give pleasure, she is not a man neither a woman she is beneath them, she must keep her body feminine and dress beautifully, she never says no to anyone, she must plug her boipussy to keep it ready for use, she must never get hard and must have a small and limp clitty, and the most important she must obey her mistress never question her follow every orders of her."
All these made me horny and juices started flowing from my penis, I got up from my computer. It had been 20 days since I had last cum, I wanted to get them out, but how I had no idea, I tried using my balls to masturbate but to no use. I remembered the time I had an orgasm through anal stimulation, I tried using my butt plug to masturbate, I found the spot I massaged it with my plug, it wasn't enough. During all this my hand lightly brushed against my nipple and I felt something I went back and played with my nipples they had gotten sensitive and I felt a current every time I touched them, pre cum started flowing, playing with my nipples aroused me why, I didn't think about it much as I was in too much pleasure. I continued massaging my prostate with the buttplug I was in heavens, after sometime I felt my penis twitching, I knew I was about to cum, the sensation increased, I increased the intensity of my prostate massage, I was about to cum.
"Such a slut you are," I heard a voice.
I stopped and looked at the door, Ms. Robin was standing there with her phone in her hand she had recorded everything, I didn't cum but started leaking, it didn't stop it kept on flowing making a huge stain on my short.
"I had made it clear; you need to control yourself and only masturbate with my permission, didn't you understand that?" she shouted angrily.
She walked towards me and pulled me to my knees.
"You need to be punished, dress up we have to go."
She went to my wardrobe and picked out some clothing, laid it on my bed and asked me to change. The panty was a black lacy one it was crotchless, there was the sleeveless fishnet crop top and a pink leather skirt and a black pair of 8-inch heels.
I stripped, she came to me and lifted my cage studied it and put it down, I dressed up. I put my make-up and looked in the mirror, I was looked like a whore, my cage hung down the panties and it was completely visible, I couldn't go out like this. Without a word Ms. Robin grabbed me by my hand and dragged me to her car, she drove to a park, surprisingly it was still filled with people at this time.
"You have to give me 100$ if you want to go back home, and don't think about running, go inside the park and get 100$ I don't care how, I will be back in 2 hours be sure to get it by then." She said and pushed me out of the car, I stood at the gate of the park thinking how am to get the money. I went in any way, and sat down on a bench, 2 mins later another woman came and sat beside me with money in her hands, she counted it and put it in her bag, I looked at her and guessed she must be a prostitute by the way she had dressed.
"First time?" she asked me.
I didn't reply.
"We all had our first time don't be shy, you won't get customers that way you are so cute, you can easily get many customers." she said.
I looked at her I didn't understand what she was saying, before I could reply she grabbed my hand and we started walking.
"I'll help you get your first customer," she said.
We walked to a man sitting on a bench alone. "Looking for a good time," she asked him.
He got up and looked at her. "How much?" he asked.
"Well, my friend will like to give you a good time," she said pointing towards me.
"20$ is the standard rate for a blowjob but you can ask them more and of course, there is the tip," she whispered in my ears.
"How much?" the man asked looking at me.
"40$," I said.
"That's the double of the normal price", he said looking at me. He noticed the cage hanging from my skirt.
"You're a sissy, I always wanted to try one, I'll give you 40 if you give me a blowjob only in your undies."
I thought about it, and agreed. He walked towards my, cupped my breasts and played with them a little, then he moved to my nipples they were already hard with excitement, he squeezed them and gave them a pinch, it felt so good I moaned.
"You like it, huh?" he asked.
"Yes," I replied.
He removed my top and his hands went to my ass, he grabbed them and squeezed them, lifted my skirt up and smacked them hard with a "THAWCK" sound, I pained but all this had gotten me horny, I started leaking, he noticed and removed my skirt, he collected my precum in his hands and fed it to me, and rubbed the rest on my face. He removed my skirt and put a hand on my shoulder, he gently pushed me to my knees, I was already horny. He stood in-front of me with his groin at the height of my face.
"Take it out," he said.
I pulled his pants down, his dick was already hard I felt it through the underwear, it was so big I never knew dicks can be this big. I could feel the blood running in it, the warmth. I pulled his underwear down, his dick got out it was huge but still soft, I grabbed in it need both my hands to hold it, my hands were small and his dick was so big, I felt it growing. I kissed the tip and then the balls, the balls were huge too, I sucked on the balls I knew he liked them as he started leaking pre-cum, I licked it. It was so tasty I needed more, I kissed it once again and started sucking it, it got completely hard now it was huge I largest I ever had, slowly I got it in deeper, it was huge and couldn't get it in completely.
"Suck it whole sissy!", he ordered. I tried but it was too big, I massaged his balls and kept getting as deep as I could.
"You're really good, but I need you to suck it whole," he said grabbing my head. He pushed his dick inside, he got his complete dick in my throat, this was the largest I ever had I was choking I couldn't breathe, my eyes got red and tears started flowing, he pulled back, I breathed and he pushed It back in, he repeated this sometimes, then he pulled it out.
"Lick it," he ordered,
I licked his dick from the head to the base, and fondled his balls at the same time, his dick twitched and `he sprayed his cum all over my face, before he could say anything I licked his dick clean and scooped the cum from my face and swallowed it all, all while smiling sluttily.
"You're really good, I enjoyed very much," he said handing me some notes and then he left, I realized all this happened in the middle of a park and the woman who helped me was still standing there.
"You did very good, considering it's your first time, looks like he has given you a tip," she said.
I counted the money, it was 80$, he must have really liked it I thought.
"Thank you, mistress for helping me," I said and kissed her shoes almost instinctively.
"I'm not your mistress," she said surprised.
"I'm a sissy, I'm below every woman for me every woman is my mistress, I must respect them."
"Why did I say that?" I asked myself.
"You are wonderful, I must say you are really well trained. Now you know how to earn here," she said.
"Yes, mistress," I replied.
"I must leave now, Goodluck," she said and left.
What had just happened, I just gave a blowjob to a stranger in the middle of a park.
"I am a whore," I told myself.
I realized I was still in my panties I got dressed and sat on the bench. I didn't understand how did I change so much, and the worst part was I liked it. I was so turned on by it, I was still leaking, I looked at the money in my hands and then the watch on my hands, I had 45 mins left before Ms. Robin returned, I had to get another 20$. I got up in search of my next customer.
After 15 mins I was a boy sitting on a bench, he was roughly my age and nervous as hell. I walked to him and faced my back towards him, bent over pretending to pick something up and give him a complete view of my ass and my cage, why did I do this, I didn't know but I enjoyed it for sure. I stood straight, and looked at him.
"Oh, I didn't see you there," I said in a slutty voice.
I went near him and realized he was my classmate, Alan; he was the dorkiest kid in school. I was amazed to see him here.
"Looking for a good time," I asked him in a slutty voice.
He starts sweating.
"Is this your first time?" I asked.
He nodded his head.
"Guess what it is my first day too, would you like to help me make my first day memorable?" I asked.
He started at me. I pressed my boobs together and rubbed them, he could see my boobs and nipples clearly thorough my fishnet crop top. I turned around and lifted my skirt up showing him my ass. I smacked it.
He got hard I saw it growing in his pants, I walked towards him swaying my hips sluttily and put a hand on his dick. He started sweating intensely.
"Do you need some help?" I asked.
He was drooling now; he nodded his head. I kept massaging his dick through his pants.
"That will cost you something," I said.
"Will 50$ be enough, it's all I have," he said.
"Yes, it will be enough," I replied.
I pulled his pants down and started stroking his penis, it wasn't that big it was around 6 inches.
I felt bad, even Alan had a bigger penis than me. But none of it mattered I was the one with a dick in my hand.r"