Sissified Ch. 02

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Transformation continues for Ron.
2k words
4.48
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Part 2 of the 20 part series

Updated 06/10/2023
Created 06/01/2021
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I was kneeling with a huge dick Infront of my mouth, I grabbed it in my hand kissed the tip and started sucking it little by little I got it deeper in my mouth, my hands were smooth hairless, finger nails were painted with pink, I looked at the mirror on my side I looked like a cute girl. I kept sucking on the dick, I felt an orgasm, a strong one I started panting, I closed my eyes enjoying every moment, when I opened my eyes, I saw the roof of my room.

I was dreaming again, I had cummed again in my sleep it had started happening almost every day, I got out removed the panty from yesterday and put it in the laundry hoping Mom wouldn't notice. I thought about yesterday how I was caught by Ms. Robin wearing panty and watching sissy porn, how she had asked me to wear panty all the time, how I had called her mistress and kissed her shoes. I realized she might ask me anytime that if I was wearing panty, I got of my room Mom had already left, I sneaked into her room opened her lower drawer from which she rarely used any item, I took a black satin panty, then I thought to myself "I have to wear panty everyday so why risk coming everyday might as well take a bunch of them now". I took 6 other panties, and went to my room. I had my bath and slipped into the black panty, I felt so smooth a part of me really loved the feel of the soft panty. I did my homework, I didn't have school as the summer break had started, so I watched TV. My phone rang it was Ms. Robin, I picked it up.

"How's my sissy doing today?" She said with a cheerful voice.

I felt a burn inside, no matter how small and skinny I was I always felt myself to be a boy, but this hurt.

"I'm good Ms. Robin," I replied in a low voice.

"I made it clear you were supposed to call me Mistress Ron."

"Sorry mistress."

"Are you wearing panty Ron?"

"Yes Mistress."

Suddenly she facetimed me. She was looking as beautiful as ever.

"Show me your panty Ron," she ordered

I pulled my pants down, and showed her my black panty.

"This color doesn't suit you, try a more girly color like pink, blue or something like that."

"Ok Mistress, I will tomorrow."

"No do it now," she replied in a strong tone.

"Now mistress?" I asked meekly

"Yes, change now and don't cut the call."

I went to my room with my phone and changed into the only pink panty I had, all others were black and white.

"This is better, you look so cute."

"Thank you, mistress."

"I will see you today, bye."

And she cut the call, I went back to my room, and started scrolling through Instagram, after sometime I heard someone ringing the bell, I ran to the door it was Ms. Robin. I opened the door she went to my room I followed her.

"No sissy video today?" she asked.

"No."

"You should watch them, you have to watch them so much that you start hating them, remember?"

"Yes Mistress," I replied thinking about her absurd theory.

"Let's watch one together it will help me learn more about it so I can help you."

"Okay Mistress."

I played "Sissification pt.3", she asked me to put my headphones on, the video was about 2 hours long, as usual I went into a trance watching it, when it ended, I found myself with my hand inside my pants and I had wet panty. Ms. Robin was sitting beside me amazed.

"Wow that was amazing, really good video it will definitely help you."

I sat there silently.

"Say what I learnt editing some time ago for editing a video for school, I will try to make more videos like this and send it to you."

"Thank you, Mistress."

"It will be great do watch them I really want to help you become yourself."

"I will, Mistress."

"It's already 9 now, I will leave your homework for tomorrow is to watch the remaining two parts of "Sissification". Now watch them while you are on facetime with me, so that I know you really watched them, otherwise I have the picture from morning of you wearing the pink panty, I will post it on all your social media," she said.

I was horrified she was blackmailing me now; I had no other option but do it.

"Goodbye sissy."

"Goodbye Mistress."

She stood there, "aren't you forgetting something?", she asked pointing at her shoes.

I knelt down and kissed her shoes, she left.

After sometime Mom came back from work.

"How was your day?", she asked

"It was good Mom."

"How's Ms. Robin teaching you?"

"She is a really good teacher, I learning a lot from her."

"I'm glad she agreed to help you," she said.

"Good night, darling," she said and went to her room.

I went to my room, Ms. Robin had texted me to facetime her anytime, I did she picked up I told her I was about to start watching the 4th part, she said to angle to phone so that the computer screen is visible to her, I did. I put on my headphone and was about to start the video, when she said.

"Remove your clothes and watch them only in your panty," Ms. Robin said

I didn't move.

"DO IT NOW," she ordered.

I had to she had my photos, I followed her orders and stripped down to my panties.

I started watching "Sissification pt.4", I went into a trance I was pulled into it, picks of big dicks, girls sucking them flashed, I realized the girls were actually male but looked like girls, some of the girls were naked and they had a small penis nothing compared to the dicks in their hands, I was staring at them without blinking. After sometime pretty sissies in lingerie started playing, they were talking about how they loved their feminine clothes how pretty they were. It kept on playing for 2 hours or so and I watched with my complete concentration. When it was over, I realized I had had an orgasm without knowing, Ms. Robin was watching me with a smile.

"Good Ron, I hope you watch the next one before my class tomorrow," She said and cut the call.

I was going to put the soiled panty in laundry, but then I thought if Mom sees so may panties in the laundry she might start doubting, so I hid it in my cupboard, I wore my boxers but couldn't sleep, I had to wear a panty so I changed into another white panty and went to sleep.

Next morning, I woke up and had my bath, but didn't put the panty in laundry as it may make suspicious seeing so many panties on the laundry, so I put the white one with the others, I had 4 dirty panties in my cupboard now. I put on another black panty, I spent my morning watching the last part of "Sissification" series it was quite short about an hour long, I facetimed Ms. Robin and let her watch me, like every time I went into a trance and had an orgasm without knowing, I cut the call and I put the panty in the cupboard, put on a fresh white one. After sometime Ms. Robin called me and asked me to send the photo of the panty I was wearing. I sent it her, she replied by asking me to change it to a more feminine color, I went to my mom's room but it was locked. I panicked and hoped Ms. Robin would understand.

Ms. Robin came in the evening; she sat on the bed and spoke.

"To help you I need to understand you completely,"

"Ok mistress."

"Now strip and leave your panty on."

I did, she had already seen me in my panties so I did it without hesitation.

"You still have those ugly panties on, I thought I made myself clear about wearing more feminine color."

"Sorry Mistress, but my mom's room was locked so I couldn't get anything else."

"You use your mom's panties, that's disgusting remove them now."

I was shocked, I couldn't move she walked towards me and said, "REMOVE THEM NOW.".

I removed them with trembling hands, as I stood there naked Infront of Ms. Robin, my penis started getting hard, it was fully erect in an instant full 3.5 inches.

Ms. Robin looked at it smiling and said, "looks like someone is excited, looks like you made the right choice, with a small penis like that you should wear panties."

I felt humiliated and started burning with same, I stood there with my face down and penis hard.

"Come on now we need to get it soft and cute again, start touching yourself," she said.

I stood there trembling she looked at me angrily and so I started stroking with.

"No not like that, sissies don't touch their clitty like that."

I looked at her when she called my penis a clitty.

"Oh, my sissy it is a clitty, you don't expect me to call it a dick now, now the proper way for a sissy to masturbate is quite difficult for you to do but let's start with something easy, rub the head of your clitty with only two fingers, like woman."

I started rubbing my dick with two fingers I didn't feel anything at start but the sensation got stronger I was feeling a strong sensation of pleasure.

"I'm cumming," I said.

She put forward one of her legs and asked me to cum on her shoes. I did, I laid back, it was the strongest orgasm I ever had.

"Now clean it sissy," she said.

I got up and picked up a tissue.

"No, clean it with your mouth sissy."

I stood there confused. No way I was cleaning it with my mouth. I didn't move.

She understood what I was thinking, and said, "Look Ron you agreed to follow every order of mine, if you don't, I will not be able to help you."

I thought about it and decided not to do it anyway.

She looked at me.

"Listen faggot, I'm your mistress now GET DOWN HERE AND CLEAN IT UP," she shouted.

I started walking towards her, knelt before her put my tongue on her shoe and started licking my cum, it tasted salty and sweet, I kept licking it and cleaned it all even after that I continued licking the shoe.

"Looks like the videos have done their job," she said smiling.

I remembered seeing something related to cum on the "Sissification" videos. I stopped licking but I craved for more cum, I couldn't control it I looked at Ms. Robin she was smiling constantly, what had I gotten myself into, I thought to myself.

"Show me your panty collection now."

I got up and bought the panties from my cupboard, only on was pink others were black and white only.

"First you have to stop wearing your mother's panties and get some of your own, but now seeing your choices I can't trust you to buy them yourself."

I couldn't understand what she was saying.

"So, we will go shopping together, it will be wonderful," she said cheerfully.

I stood there shocked unable to say anything.

"I get it you are too excited to speak, I'm excited too I will pick you up tomorrow morning and we will go to the mall, now say goodbye sissy," she said bringing her shoe forward.

I slowly knelt down and kissed her shoe it still had the smell of cum on it.

She left, and I was thinking what had happened with me I had started wearing panties, licked my own cum and was going panty shopping with my teacher, I lied on my bed thinking about tomorrow.

To be continued....

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12 Comments
IntoblackIntoblackover 1 year ago

I'm enjoying the series, but you really should find an editor. Keep writing!

sweeterika2sweeterika2over 1 year ago

sounds so nice being trained as a sissy makes Erika feel so sweet licking up cum satisfying men

AnonymousAnonymousover 1 year ago

Ron is really lucky to have such a great teacher.

AnonymousAnonymousover 2 years ago

lucky sissy

slavetobyslavetobyover 2 years ago

This is getting better and better and I have really enjoyed reading this. I will read the rest for sure

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Sissified Ch. 01 Previous Part
Sissified Series Info

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