Sissified Ch. 11

This is the eleventh story in the series, please read the previous chapters so as to understand the story better. The first part of this chapter will be from Esme's perspective and the second from Ron's.

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I woke up as usual, naked. I put on my gown and went downstairs, my sissy son Ron served me breakfast; eggs, bacon and fresh coffee. I sipped my coffee and looked at him, dressed up in a pretty maid uniform with high heels and stockings, cute ass with a jewelled butt-plug in it, long blonde hair and a cute caged cock dangling between his legs. He had come a long way now, before seven months he was short, scrawny kid who always got bullied. A lot had happened since his teacher Robin came into our lives; she had changed him for better. She had helped him to his true self, how much he had changed now, he looked like a beautiful girl, with a toned body and a cute feminine face, his voice had also changed. He was happy now. He had found his true purpose; to serve.

"Good morning mom." Ron said.

"Good morning Ron." I replied.

I put a piece of bacon, he was such a wonderful cook, he did all the house work; cooking, cleaning, laundry. He was home-schooled now so he had a lot of free time to learn. I had made him learn all the house hold work and he had gotten so good at them, she was the perfect maid.

It had been four months since he had been my maid, I had just returned from an awesome trip and had found him dressed up, after Robin had explained everything, I had decided to support him in his transformation. I looked at his tiny penis hanging between his legs, it was so small.

"How long has been locked up?" I thought.

"Ron?" I asked.

"Yes, mom."

"How long has it been since Robin locked you up?"

"It has been a little more than six months." he replied blushing.

"Do you feel anything down there?"

"Yes, I sometimes have an erection, usually when I'm practicing with my dildo, but the cage prevents it."

I had forbidden him to masturbate without my permission, it had been two months since he last cum. At first, he didn't follow my instructions or orders, I had to discipline him so I used the cameras in his room to keep an eye on him. Due the hormones he was taking kept he was a horny all the time. So, I forbid him from masturbating to get him to follow me and only allowed him to cum when I wanted.

"How long has it been since you last came?" I asked.

"A month mom." he replied.

"Do you want to?"

"Only if it pleases you mom." he replied in a low voice.

Robin had trained him well; he was so submissive now. He was going to be a perfect sissy.

"Good answer sissy, I might let you masturbate." I said.

"Thank you, mom."

I went to the bathroom and had my bath. I put on a bra and a panty with floral print. I never covered myself in the house, I had no problem with Ron seeing me naked, he wasn't a man anymore, he was a sissy. I rang the bell and he came to my room.

"Strip." I ordered. He complied and stripped naked.

"Bring your favourite toy." I told him.

"Yes, mom." he said and left and came back with a 12-inch dildo.

"Good choice, now masturbate but use your saliva as lube." I said.

He understood he lubed the dildo by sucking it wet and when it was well lubed he placed it on the floor, removed his butt plug and inserted it and started pounding his ass. He moaned lightly.

"Ron, I have to tell you something and I want to cum after I have finished talking or else you will be punished and don't stop masturbating, do you understand?".

"Yes, mom." he replied.

"I have been seeing someone, do you remember Joe?" I asked.

"Joe your colleague?" he asked.

"Yes, he had been asking me out for quite some time, but I wanted to spend some time with you. So, I rejected his advances. But when Robin started teaching you in the evenings, I decided to give him a try and agreed to go out with him."

Joe was a Vice-President at my company. He was a big man literally, he was around six and a half feet, well built, shaved head. He was so handsome. I was surprised the first time he asked me out.

"We went out for dinner. I enjoyed his company; he was such a gentleman. I went out with him a couple of times. He was the perfect guy; smart, funny, he understood me. we kissed the second time we went out, he was dropping me home, I said good bye and was about to leave the car when he called my name and leaned towards me and kissed me passionately." I said.

"I'm happy for you mom." Ron said still pounding his ass.

"The next time we met he picked me up from my waist like a baby and kissed me, our tongues intertwined and we only stopped for breathing. We went to his house. I started removing his pants but he stopped me. he wanted the first time to be special, so he asked me to go on a vacation with him, I agreed."

"So, the business trip?" he asked confused.

"There was no business trip, I was on a vacation with Joe. We went to Hawaii, he had planned so well, first we had a romantic dinner then a walk by the beach, we kissed passionately on the shore. Then we moved to our room. We slowly undressed each other. When we both were naked, I took a look at him, he was so well built, and his cock was amazing, it was about 8-inches long and 2-inches in width." I said.

Ron continued masturbating, I could see he was about to squirt but he controlled it. I was horny too now. I remembered Joe's cock, I pulled my panties down and told Ron to lick my vagina.

"I took it in my mouth for the first time, it was so thick and veiny I could feel it growing with every suck, I took it in slowly going deeper in my mouth every time. After sometime he gently picked me up and put me on the bed, he went on his knees and licked my pussy, he was so good at it. I couldn't think straight."

I looked down Ron licked my vagina perfectly; I was so wet now. I continued the story.

"He got up and rubbed his cock against my vagina, and slowly he entered me. he did it so gently, I was filled with pleasure it had been so long since I last had a cock in me. Slowly he increased the speed, I could feel his blood pulsing in his cock, my vagina tightened around it. He continued pounding me with his cock, I felt something I hadn't in a long time. I came hard and he came together with me." I said.

I could feel myself cumming now, Ron had become an expert in pleasing women, with his mouth. I came hard on his face and he licked me clean.

"You can squirt now." I told him.

His legs shook and he squirted ropes of cum, his face gave a satisfied look, he licked his cum clean. He already knew it was his duty. I reminded him he had to go out with Robin in the evening. He nodded and left. I drifted into sleep exhausted.

I returned to my room satisfied mom had finally let me cum after a month, I cleaned myself and got back to my chores, when I had completed them, I came back to my room. I received a new video from Ms. Robin. It was titled "Anal whore". I played it; it was a video of sissies getting fucked by huge cocks. Beautiful sissies were getting rammed in the ass by men, their pathetic little penis wiggling between their legs. A message played in the back ground.

"I am a whore for cocks, I no longer have a penis, I can only come by getting fucked by huge cocks."

I repeated after it. It played for a long time and when it was over, I was too horny to think, my penis leaked through the cage continuously and my mind was blanked out. I got a message from Ms. Robin that she was coming to get me and I had to get ready. I gathered myself and changed into a red satin pair of bra and panty. I slipped a black short dress and put on red heels. I corrected my makeup and waited for her.

I heard her car and went down. I saw her car and got in.

"Looking good sissy."

"Thank you, mistress."

Without saying another word, she drove. We pulled up infront of a club. The bouncer seemed to know Ms. Robin as he gave her a smile. He was a huge black man, and almost instinctively I thought his cock, how big he must be. We went inside and straight to the bath room. There in the corner booth was a hole on the wall, I understood why I was here. I got on my knees infront of the hole and knocked. Almost immediately a cock came out, it was huge around 9-inches and black, I was about to touch it when Ms. Robin stopped me. She pulled out a dildo from her bag which was almost identical to the cock infront of me.

"I want you to bounce on it while you suck the cock today." she instructed.

I took the dildo from her and licked it wet and positioned it. I pulled out my plug and slid it inside, I let out a moan when it slid inside me, it felt so good. I grabbed the cock infront of me and kissed the tip and started blowing it. with every blow I went deeper and simultaneously fucked my ass. Within no time I was balls deep both in my mouth and ass. I was in heaven it was suck a new experience and I loved every moment of it. I felt the cock twitching I sucked harder and he came into my mouth, I gulped it all down. I was still leaking and hadn't cum, I wanted to continue fucking myself but Ms. Robin stopped me, just when I was about to cum. The cock went inside the glory hole but no money came out. I was confused.

"He already paid in advance." Ms. Robin said.

"Who is he?" I asked.

"Oh, you already met him. He is the bouncer, I arranged it, he has a fetish for cute sissies like you."

"I understand mistress."

We went out and saw the bouncer again on the gate.

"I would give you anything to pound that sissy ass." he said.

"He isn't ready yet, but I will inform you as soon as he is." Ms. Robin replied.

"Nice."

He looked at me with lust filled eyes. We left and got back into the car. I was still horny.

"Now tell me one thing sissy, did you ever feel like needing a real cock inside you?" Ms. Robin asked.

I don't know if I really wanted it or I said it just because I was horny and couldn't think straight.

"Yes, mistress." I replied confidently.

"Interesting, tell me more."

"Ever since mom told me about her boyfriend and how well he pleasures her, I wanted to feel it myself. Even when I was giving a blowjob today, I imagined him fucking me, I was so turned on by it. I don't know why, but I think about getting fucked all the time."

"Thank you for sharing this with me. I will try my best to help you, now let us go to the toy shop, we need to get you some more toys."

She drove us to the sex shop and we went in. I was greeted by a familiar face.

"Ron is that you, you have changed so much." I counter girl said.

"Yes, he has changed a lot Ruby." Ms. Robin replied.

So, Ruby was her name, I couldn't ask her name the last time I visited.

"So, what can I show you today?" Ruby asked.

"Show me some new toys for him." Ms. Robin replied.

"I have a variety of new cages. I will show you but first remove his cage so I can measure his current size."

Ms. Robin lifted my dress and removed the cage, I was horny as I had not cum yet. I got hard instantly. I saw my penis it was so small now, less than an inch even when it was hard and the balls had shrunk too.

"How did I get so small?" I said socked.

"Don't worry it's because of the pills, once you stop, they will go back to normal. It looks better now anyway." Ms. Robin said and laughed, Ruby joined in.

I was embarrassed. But my penis was still hard.

"Looks like you still need some more discipline." she said angrily and grabbed my balls.

It hurt like hell, I shouted but she didn't let go, all this pain caused my penis to shrink back.

"Don't do that again, control yourself." she explained.

"Sorry, mistress." I said.

"I have a perfect solution for this." Ruby said.

She took out a small box and pulled out a metal chastity cage, I was so small around half an inch and a metal hollow tube attached to it.

"It is a new model this metal tube goes inside his clitty, it is a hollow tube, so he can piss and cum without any problem, but every time he tries to get hard it will give him a shock. It has good reviews from our customers, it helped their sissy to control erections even better." she explained.

"It is perfect." Ms. Robin said.

Ruby walked to me and help my soft cock, I looked at it, only the head was visible now, it had gotten so small. She lubed the tube and slid it into my penis, next she took the cock ring and squeezed my balls through it and finally put the cage and clicked it shut.

"The key?" Ms. Robin asked.

"It's on your phone, just download the app and you can unlock it from anywhere."

"Brilliant!" exclaimed Ms. Robin.

I kissed Ruby's feet and said good bye and we left. On the way I got electric shocks a lot of times as I was horny as hell. I reached home and got inside. mom greeted me.

"How was your day, Robin said you got a new toy show it to me." she said.

I pulled up my skirt and showed my new cage to her.

"I looks so cute on that small clitty, I love it. It will help you control your penis."

"Yes, mom."

"Get changed and come down for dinner."

I went to my room and changed into the oversized t-shirt and came down for dinner.

We ate dinner and I took my pills afterwards.

"Let us talk before you go to sleep." mom said.

"Ok mom."

We sat down on the sofa.

"I love how you have changed; I am happy you finally found your true self. I always wanted a daughter as I was afraid you will grow up to be like your father and leave me someday."

"Mom. I would never."

"I know but still I was scared. Now I am sure you will never become like that. I am so happy."

"Thank you, mom for supporting me."

"Tomorrow I will take you to a special place. It will change your life. You will finally become my daughter. Now go and get some sleep."

"Good night, mom."

I went to my room. I tried sleeping but the shocks prevented me from sleeping. I had to do something I grabbed my dildo and slid it inside my ass. just then I got a text from Ms. Robin.

"Are you trying to masturbate without my permission?"

"No, mistress." I replied.

"You can, I give you permission."

"Thank you, mistress."

I jumped out of my bed and got on my fours infront of the fucking machine Ms. Robin had gifted me. I started it. It slowly slid into my ass and gently pushed against my prostate, slowly I increased the speed. It grinded against my prostate, I started leaking but I started getting shocks again. Ms. Robin texted me.

"I'm removing your cage, but you dare not touch your clitty."

"Yes, mistress."

The cage clicked open and it removed it. I started the machine again, it pushed against my prostate and I started leaking but I didn't get fully erect. I continued getting fucked by the machine. After sometime my legs started shaking, I was leaking continuously now. I came hard, I lied down exhausted, but I wanted the cum. I scooped it up and licked it clean.

"You had your clitty uncaged but you still came through anal stimulation, I am proud you. Now put your cage back on." Ms. Robin texted.

I put it on and clicked it shut.

"You are finally ready." she texted.

"Ready for what Mistress?"

"You will know soon enough."

I got to my bed and tried to sleep, I thought about where mom was going to take me tomorrow and what I was ready for. I drifted into sleep and dreamt about getting cocks inside me.

To be continued...