Sissified Ch. 10

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Mom finds out about her sissy son.
2.3k words
4.64
36.2k
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Part 10 of the 20 part series

Updated 06/10/2023
Created 06/01/2021
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This is the tenth story in the series, please read the previous chapters so as to understand the story better.

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"Ron is that you?" mom asked again.

I stood there silently; I couldn't believe this was happening. Mom had caught me dressed in female clothes. All this had happened so suddenly, I just came home to get some documents, I didn't bother to change into boy clothes as I knew mom was on a business trip, but she came home without any notice and she caught me.

I was still processing it when Ms. Robin walked in.

"Esme, it's good to see you again." she said to mom.

"Robin, what happened to Ron?" mom asked.

"I just helped him get over his porn addiction." she replied.

"How does dressing up like a girl help him?" mom asked.

I gathered my courage, I had to speak up.

"Mom I didn't want you find out like this, I thought I will be over the porn addiction before you got back, I didn't expect you to return unannounced." I said.

"I called Robin yesterday and told her I was coming home today." she said.

I looked at Ms. Robin, she was smiling.

"I wanted you to see for yourself how much he has changed." Ms. Robin said.

"But, why?" mom asked.

I stood silently.

"Please explain why you had to make him dress up as a girl."

"Esme calm down let us sit and talk." Ms. Robin said pointing to the sofa.

Mom and Ms. Robin sat down, I also sat on a sofa. Ms. Robin shot me a look. I understood, I quietly kneeled at her side. It was humiliating doing it alone was different, but kneeling like a slave Infront of mom was humiliating.

"Why is he kneeling?" mom asked.

"Esme I will explain everything to you, first you must know why I did this, I did it to help Ron find himself." Ms. Robin said.

"I don't understand." mom said, still trying to understand.

"Let me ask you something, did you ever think Ron as a man. Someone whom women would want, someone who was strong enough to look after himself." Ms. Robin asked.

Mom thought for a while.

"No, I never thought of him as a man, I mean he was small and skinny and I once caught a glimpse of his penis when he was in the bathroom, it was so small. I thought it would grow with age." mom replied.

"Even I thought so but all my doubts were confirmed when I caught him watching sissy hypnosis and porn, and he was enjoying them. I understood then and there I had to help him, as a teacher I couldn't let him be confused for the rest of his life."

"Yes, I understand. Even though he is my son I never expected him to live his life as a man, he will only get hurt." mom said.

"Finally, you understand. I had to let him discover himself what he wanted to be." Ms. Robin said.

"I get it but I can't let my son be a weirdo who wears girly clothes." mom said.

"I know that would be weird, let me show you something it will help you."

She showed mom something on her phone. I tried to peek what she was showing. She was showing her the pics I sent her in panty, then me masturbating like a girl in the trail rooms. My videos of seducing people in the park, and at the photoshoot, me giving blow jobs. Mom looked at them with eyes wide open. After all this was over mom looked at me.

"Esme, I hope you understand now, I just led him in the right direction. He is the one who chose to do these." Ms. Robin said.

"Ron, darling I leave the decision to you, what is it you want?" mom asked.

I thought about all the things I had done, from dressing up to blowing cocks, the amazing feel of sissygasms. How much I enjoyed looking feminine, how I wanted to become more beautiful. For a moment I wanted to go back to normal, but then I didn't want to lose my body which I had worked so hard to get, the bubble butt, A cup boobs the cute face. I wanted it all. I thought for a while.

"Mom, I'm a sissy. I love it, I want to be more girly and beautiful. I hope you will support me and I thank Mistress for helping me find myself." I said confidently.

Ms. Robin was smiling and looking at me proudly.

"You are most welcome Ron, I knew one day you will understand, this is who you were meant to be, I wanted to help you to realize that." Ms. Robin replied.

"Yes, mistress." I replied.

Mom looked at me with a slight smile.

"If that is what you want, then I will support you, but I won't accept a boy who dresses as a girl, you must become a full-fledged sissy." mom said.

"I don't understand mom."

"You must leave your previous life behind, you will no longer be my son, but my daughter. You have to leave every last bit of that life behind if you want me to accept you." mom explained.

"Yes, mom I agree from today I will be your daughter." I replied.

Mom cupped her hands around my face and kissed me on the forehead.

"I always wanted a daughter, this is perfect you will be my sissy daughter, I will help you in every way I can." she said.

"First we must get rid of all male clothes, go and bring them all." Ms. Robin said.

I went to my room and collected them and brought them to them.

"Now put them in the incinerator, you must be the one to burn your masculine life away." Ms. Robin explained.

I went and put the clothes in the incinerator, as I watched them burn, I realised there was no way back to the life I once had, my life will change completely from today.

"I heard you have learnt quite a lot about pleasuring women." mom said.

"Go on show her what you have learnt." Ms. Robin said.

I went and kneeled Infront of mom. I picked her feet up and removed her shoes, I slowly licked her foot and started sucking her toes.

"You have trained her well." mom said.

I sucked her other foot. I slowly removed her panty and licked her clitoris first, she was wet by now, I continued licking it and moved down to her pussy lips and rubbed her clit with my finger, I looked up she was playing with her nipples and moaning, I continued licking her. I pushed my tongue inside her pussy and hit the spot, she moaned loudly and came hard. Juices flowed out her and she laid back exhausted.

"You made the correct choice, you could have never pleased a woman with your penis, but now you can at least please her with your tongue." mom said.

"You should see how well trained his boipussy is." Ms. Robin said.

"If you want to stay in the house, you must continue doing what you did at Robin's house, she showed me the videos. You were such a good maid, you will continue to be a maid in this house too." mom said.

"Yes, mom." I replied.

"Well, there are some things that need to discussed, but you look exhausted Esme we will talk tomorrow." Ms. Robin said.

"Okay Robin." mom replied.

I kissed her shoes and she left.

"I always wanted a daughter, I love you Ron, you have given me the greatest gift, I will make you the most beautiful sissy ever." mom said.

"Thank you, mom." I replied.

In the evening Ms. Robin came to drop all my clothes and toys. I changed into my maid uniform and got to my chores; mom loved the dress. Ms. Robin had asked me to keep practicing with my toys and I did.

Next morning Ms. Robin came to meet mom.

"Esme, Ron has learnt his duties and place as sissy, but a sissy must work on his looks too, even though he has a curvy figure, the base is still like a boy we need to get him a more girly shape, I know a good doctor and I have also made an appointment, that is if you want to do it." Ms. Robin said.

"I could agree more, I want my sissy to look beautiful, let's go and meet the doctor." mom replied.

We drove to a clinic. We went to the receptionist.

"I have an appointment for Ron with Dr. Sandra." Ms. Robin said.

"Yes, the doctor is waiting go in." she replied.

Mom, me and Ms. Robin went inside. The doctor was a beautiful woman with shapely breasts and ass, she was breathtakingly beautiful, I kissed her shoes and greeted her.

"Is this Ron, I would love to help a pretty thing like her." she said.

"Yes, it is Ron." Ms. Robin replied.

"And I'm his mom."

"You are such a good mother, very few would accept their son like this." doctor said.

"I want him to be happy." mom replied.

"Strip please." doctor said.

I stripped naked, she called me near her. I walked to her, she examined my body, she squeezed my ass, my boobs and nipples, she examined my balls and penis and asked me to say my name.

"Progress Is good, the hormones I gave you are working fine, her fat has already started depositing oh her hips and ass, as you can notice her nipples and boobs have started growing and her voice had changed and he sounds like a woman."

I realized the pills and the liquid she had been giving me were hormones that is the reason I had changed so much, but it was good, I liked being this beautiful.

"Most importantly his balls have shrunk and his penis too, that is a good sign, it means his testosterone levels are going down which will help him even more." doctor continued.

"Wonderful!" mom exclaimed.

"Glad you liked it Esme." Ms. Robin said.

"She has become so beautiful, doctor is there a way to make her even more pretty?" mom asked.

"Yes, we can increase her dosage now if you want." doctor replied.

"Yes, please I want a perfect daughter as soon as possible." mom replied excited.

"Very well then, this is the new dosage." doctor said handing a paper.

We thanked the doctor and left, mom bought the new pills and we came back home.

"Robin, I can't thank you enough, I never knew Ron was in so confused. We are lucky that you realized it and helped Ron." mom said to Ms. Robin.

"I am his teacher. It is the duty of a teacher to guide her students, that is what I did, you don't need to thank me." Ms. Robin said.

"He has become so more productive. Before he used to spend all his time in his bed, but now he does so much work." mom said.

"I'm glad you like his changes, there is one more thing we need to discuss." Ms. Robin said.

"What?" mom asked.

"His summer break ends in a week."

I remembered I had a life, I went to school, my summer break will be ending in a week, I had changed so much I couldn't go back to school like this, everyone will notice it. I will be a freak and will surely get bullied. I started sweating.

"What happened Ron?" mom asked.

"I can't go back to school, not like this." I said crying.

"I knew it, that's why I already thought of a solution." Ms. Robin said.

"What is it?" mom asked.

"We will home school him, I will make the arrangements. For the last year of school, he will be home schooled." Ms. Robin explained.

"That is a nice idea." mom said.

"Great I will arrange everything, now we can use the spare time to train her to get even better."

"Yes!" mom exclaimed.

Mom looked at me.

"Let us celebrate this and I know the perfect way to celebrate." she said winking.

Ms. Robin seemed to understand what mom was saying, she went into my room and came back with two strap-on dildos. Mom took one and wore it and Ms. Robin the other. They moved near me and started stripping me. I was shocked to see mom do this. They stripped me naked and pushed me to my heels.

Mom went behind and pushed the dildo deep into me, before I could make a sound Ms. Robin pushed one into my mouth. I was being in both of my holes, mom spanked my ass and kept grinding against my prostate and Ms. Robin kept pushing deep into my mouth, I was breathless and in so much pleasure, this went on for some time and mom made me cum.

"Lick it clean sissy." Ms. Robin ordered.

I licked it up.

Mom looked at me.

"Do you like the taste?" mom asked.

"Yes, mom I love it." I replied.

"You are such a good sissy." she said happily.

"I'll leave now, hope you enjoy your new sissy." Ms. Robin said and left.

Me and mom were alone she made me dinner.

"I am so happy to have such a good daughter, I will dress you up and make you so beautiful that it will make every man look at you. I can't wait to make you my perfect daughter." mom said.

"I can't wait mom to start my life as your daughter."

She smiled at me. After dinner I went to my room. I changed into a nightie and went to sleep thinking about my new life ahead.

To be continued...

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4 Comments
AnonymousAnonymousover 1 year ago

How every boy should treat their mother when found dressed sissy.

AnonymousAnonymousalmost 2 years ago

Invest tag pls, it is gross

awyldsideawyldsideover 2 years ago

“ if you want me to accept you.“

Mother of the year award goes to…

Mom wants a daughter but has her daughter eat her pussy and then fucks her! Great incestuous family.

I thought the non consent of Robin giving him hormones and blackmail was bad…

The mother wants a daughter but calls him “him”?

If only when Robin started blackmailing him with a photo all he had to do was say that he would tell his mother and the school board, he may have had more control over his situation.

But, like a good car wreck, I can’t look away.

AnonymousAnonymousover 2 years ago

Incest tag required. Gross

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READ MORE OF THIS SERIES

Sissified Ch. 09 Previous Part
Sissified Series Info

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