Sissified Ch. 03

Story Info
Sissy goes shopping.
3k words
4.56
65.2k
49

Part 3 of the 20 part series

Updated 06/10/2023
Created 06/01/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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

**********************************************************************************

It was blurry but I could see a cock dangling above my head, I grabbed and felt its heat, I felt the cock throbbing. I gently kissed the tip and started sucking it slowly, going deeper every time till the balls hit my chin, it was such a great feeling. It gaged me, I was begging for air even then I loved the feel, it twitched, but he didn't remove it. He came in my mouth; I loved the taste. I looked to my right there was a mirror. I saw myself dressed in a panty looking like a pretty girl with a cock in her mouth. I heard something.

I woke up, my phone was ringing, it was Ms. Robin. I picked up the call.

"Good morning sissy.", she said in a cheerful voice.

"Good morning mistress.", I replied.

"I'm so excited, I will pick you up at 11 be ready.", she instructed.

I remembered; I was supposed to go shopping with her for my clothes.

"Is it necessary to go shopping mistress?", I asked.

"Yes, you need some new clothes and you have to agree wearing your mother's clothes is kind of weird. No excuses now, be ready at 11."

"Ok mistress."

I got up and had a shower, I went downstairs and had breakfast with Mom. She left shortly.

I was drawn to my computer, I stripped and only wore my panty. I need sissy porn, I had to. I played one, halfway through the video Ms. Robin called. I was so horny but I had to go. I quickly got dressed and left the house. She was outside in her car. I got in.

"Are you wearing a panty?", she asked.

"Yes, mistress.", I replied.

"Show me."

I lowered my pants and she noticed my boner.

"Someone's excited, but we can't let you have a boner while we are shopping.", Ms. Robin said and grabbed the base of my penis and squeezed tightly within seconds it got soft.

"It's better now. But the panty is still boring, remove it."

I removed my pants and my panty. I was in her car naked from waist. She handed me a bag. There was a cute panty inside with the words sissy printed on the ass, I slipped into them.

"They fit you perfectly, I had them custom made for you. Do you like it?", Ms. Robin asked.

"Yes, mistress they are perfect. Thank you.", I replied.

"Glad you liked them, now let us go to the mall."

We drove to the mall and got in.

We went to Victoria's secret. It was heavenly, panties and bras of different types, the variety of lingerie and other feminine things, this was the most exited I ever was in my life, but still I thought to myself why did I like this.

"Go on touch them, feel them.", she said showing me the lingerie.

They were all so soft, I loved them.

"Wow! The videos have done wonders.", she exclaimed.

It was because of the "Sissification" videos, it somehow made me like these things, they were also the reason I liked dressing up and eating cum.

"What is happening to me?", I asked Ms. Robin with tearful eyes.

"Don't cry Ron, this is perfect the faster you embrace all this the faster you will be able to quit these things.", she said.

I looked at her hoping this to be true.

"Now, let's do what we came here for, shopping. I have a friend working here who knows about our situation she will help us, there she is.", she said pointing to someone.

I looked at her she was a beauty, she was around 30 and hot as hell, she had the perfect boobs and ass and face like an angel with very minimal makeup, she walked towards us smiling.

"Janet, this is Ron. It's his first time.", Ms. Robin said.

"Hey Ron I have heard a lot about you, let's get you some pretty clothes.", Janet said.

"Thank you.", I replied.

"See Ron you are a sissy so pretty much every woman is your mistress now, so treat them as such.", Ms. Robin said.

I was silent for a second and tried to understand what Ms. Robin was trying to say.

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

"Good.", Ms. Robin said.

"You are so cute and such well-trained.", said Janet smiling.

We went to the panty section, Janet ordered me to strip. I did, I was naked in a lingerie shop, Janet came closer and measured my size, she looked at my penis.

"Good thing you decided to wear panties, they will look great on you and your small size of your penis will definitely help.", Janet said giggling.

I was burning with shame, but it turned me on too. I started getting hard. Ms. Robin noticed.

"You must learn to control these, otherwise I will have to search for a solution.", she said angrily.

Listening to her words I immediately lost my hardon.

"His size is small, I will be back with the panties.", Janet said and walked away.

She returned with a variety of panties, "So, which one should we try first?", she asked Ms. Robin.

"Let's start with cotton ones for daily use.", she replies.

Ms. Robin picked up a white panty with blue horizontal stripes handed it to me.

"Go on try it.", Ms. Robin said. I pulled them up, they fit perfectly.

"They are perfect.", Ms. Robin and Janet said in unison. Ms. Robin selected six more of the cotton panties and as they were of same size, I didn't have to try them on.

"Now, let's see satin panties.", Ms. Robin said.

She took a pink satin panty and handed it to me, I tried them and they were so light and the material was so smooth I fell in love with them.

"They are so good.", I said instinctively.

"Glad you like them.", replied Janet.

Ms. Robin selected 4 more satin panties of different colors. After that I tried some lacy ones and some frilly ones, they were good and Ms. Robin selected four from each of them. Next were G-strings, when I first saw one, I thought how can I fit in them, they were so tight there was a small cloth covering my penis and the string went between my ass cheeks, they were so exposing.

"They look lovely on you.", said Ms. Robin.

I was wearing a neon-colored G-string. We got 7 of those of different colors.

"That should be enough for now", Ms. Robin said.

Finally, it was over I thought to myself as we were turning to leave Janet called us.

"There is one design you will love Robin, want to see it?", she asked.

"Sure.", Ms. Robin replied.

Janet came back with a small panty and it had a gap in between.

"These are crotchless panties, they are trending now you should try them."

There was no way I was going to wear when Ms. Robin called me I didn't move and told her I won't wear them.

"Come here Ron, try them.", Ms. Robin said.

"No.", I replied.

"For the last time come here.", Ms. Robin said sternly.

I didn't move. She walked towards me and showed me my photo in panties, I understood I walked there silently and tried them on, they were so weird they were small to begin with and now my penis was hanging down between my legs, the cold air on them made them shrink and made them look even smaller.

"I love them, pack another four of these, and she will be wearing these out.", Ms. Robin said.

We went to the counter to pay the bill was 968$.

"Pay up Ron.", said Ms. Robin.

I looked at her I didn't have that much money I told her.

"Then how were you planning on paying them, these for you so you must pay.", she said.

Janet noticed this and said "We have a scheme where you can model in these and get 50% off, and we would love to have you as a model. There aren't many sissies as cute as you."

"We will do it.", Ms. Robin replied.

"Nice, I will call you on the next photoshoot. So, you have a 50% discount but you still have to pay the remaining amount.", Janet said.

I looked at Ms. Robin, she looked back at me with a cunning smile it felt like as if she had seen this happening.

"I will pay for them but you will owe me and work to return the money.", she said.

Before I could say anything, she had already paid and we left the store. I kissed Janet's shoes and said goodbye.

"You humiliated me by denying my order back at the store and you will be punished.", Ms. Robin said.

"Sorry mistress, I will never do it again.", I said.

"You need to be punished it will teach you what happens when you deny your mistress.", she said and dragged me to a beauty salon.

"Hello Sophie, he will be needing a full body Brazilian waxing.", she said to the girl in the salon.

"Very nice, come with me.", she said to me.

I followed her, I knew what waxing was but what was Brazilian waxing I asked myself, but didn't dare to ask anyone else. I went inside with Sophie, she asked me to strip and made me lay on a bed.

"Relax.", she said.

She started saving my face, then waxed it and moved to my chest and back, then my lower torso, my arms then she waxed my legs it was painful but endured it.

"Now lift your legs and put them in these, now let's start the Brazilian waxing.", she said pointing towards two loops hanging from the roof.

I put my legs into them she then started applying was above my penis, I finally understood what Brazilian waxing was but it was too late, she waxed around my penis, on my scrotum and my ass. When I got up and looked at the mirror, I saw I was hairless from below eyebrows my body was so smooth, I loved it. I put on my crotchless panty, it felt different now.

"I have used a special wax you won't need to wax again for another six months, now let's finish your other treatments.", she explained.

I followed her, she made me sit on a chair and gave me haircut, then she did some treatments on my face and applied light makeup, I didn't have the guts to say no to any of these, I was too afraid of Ms. Robin. When I looked at the mirror, I saw a pretty girl staring back at me, Sophie had styled my shoulder length hair to a pixie bob cut, my skin felt smooth and the makeup was minimal.

"You look beautiful, and don't worry your skin will remain smooth like this.", Sophie said,

She gave me a small makeup box. I left the store.

"You look so pretty, you will become the perfect sissy in no time, By the way I have added the salon expenditure to the money you owe me.", Ms. Robin said

"Ok mistress.", I replied, what could I say to her.

"Let's go and buy some clothes for you.", She said.

We went to a clothes shop, there she selected some crop tops and shorts to wear at home, then we bought the smallest hot pants and spaghetti tops, couple of camisoles, I didn't find trying them weird so, we found my size easily. Then she made me try miniskirts, the ones she selected were so short that my panties were easily visible and wearing crotchless panties made it even worse, she bought some t-shirts to go with them. As we were leaving, she spotted the dress section.

"We have to buy some dresses for you.", she said excitedly.

She picked up a black short dress and handed it to me. It was 3 P.M now the mall had started getting crowded, I noticed I was the only boy in the store, but none of them looked at me, maybe due to my haircut and makeup, they thought I was a girl, my doubt was cleared when I saw a couple of boys looking at me from outside the store and making flirty faces, I blushed and went to the dressing room, after I stripped, I looked at myself in the mirror I looked more like a girl than a boy and strangely I liked it, must be the videos again but anyway I loved it, just then Ms. Robin entered the room.

"I was checking if you wanted any help with the dress, go on wear it.", Ms. Robin said.

I put It on and then looked at the mirror I looked like a girl.

" I look like a girl mistress.", I said with excitement.

"No, you look like a sissy, you will never be as good as a girl they will always be better than you, you're a beta male always remember that and never call yourself girl again, understood?", Ms. Robin said sternly.

"Yes mistress.", I replied.

"Good, now lift up your dress sissy.", she ordered.

I complied, I lifted my dress my penis was still soft but when I looked at my reflection, I started getting hard, Ms. Robin saw this.

" Touch yourself sissy.", she said.

I did the way she had taught me I rubbed my penis with two fingers. I touched the tip and licked the precum off my fingers, then moved them in a circular pattern, I was filled with ecstasy I rubbed and rubbed, the pleasant sensation took over me and I came hard all over the mirror, I instinctively started licking it clean I loved the taste so much it was the best in the world, after I had licked every drop of cum, I looked at Ms. Robin she had been recording everything.

"Don't worry no one will see this as long as you follow my orders.", she said and smiled.

I changed back into my clothes and she was done selecting four more dresses; two were short dresses on read and one in blue, and other two were summer dresses a white one with floral patterns and another yellow with white polka dots. Then she got me two nighties one transparent black and another red, and three baby dolls black, pink and blue in color. Then we left the store and went to a footwear store, it was getting late we quickly grabbed a girly pink sneaker, flat shoe and a six-inch red high heel and left the store, on the way-out Ms. Robin bought me a milkshake and told me to wait by the car, she returned after 15 min with a paper bag. We got into the car and she drove me home, we went inside she pulled out a white crop top with sissy printed over it and a red short, she asked me to wear them and I did.

"From today you will wear only female clothes all the time, you are allowed to wear your old clothes only if your mother is around, even then you will have to wear panties underneath.", Ms. Robin instructed.

I nodded.

"Always wear a panty and clean all the clothes yourself, at night you must wear a nightie or a baby doll, and if I ask you to go out with me you must wear from the clothes you bought today pair them up with the appropriate footwear, do you understand?", she asked.

"Yes, mistress.", I replied.

"Speaking of footwears I will teach you to wear heels and how to apply makeup today in class, always be in makeup when you are alone or with me again you may remove them when you are with your Mom, maintain your hairstyle and be clean, you must learn to be a perfect sissy, I will be sending you some videos today do watch them while facetiming me and give this packet to your Mom don't open it yourself.", she said handing me the packed, it was quite heavy.

"Ok then I will see you at 7, bye sissy."

"Goodbye, mistress.", I said and kissed her shoes. She left.

I took out the clothes I had got, I noticed most of the crop tops had sissy or slut printed in-front of it how had I not noticed that I thought, the crop tops were quite small and ended way above my navel, and the shorts ended 4 inches below my waist I felt almost naked wearing them, then I went to the mirror and looked at myself I was beautiful I thought, I loved the way I looked I looked slutty and cute at the same time I pulled down my shorts and saw myself in the crotchless panty my penis was hanging out between my legs, without the hair it looked even smaller, it looked like a baby dick I felt horny I started rubbing my penis even though mistress was not there I rubbed my dick didn't jerk it I loved it this way I felt like a woman, I cummed in my hands after some time, I bought my hand to my face and put the cum in my mouth I savored it, moved it around my mouth then finally swallowed it, I loved its taste. I folded my clothes and put them in my wardrobe I put my new shoes in the wardrobe and put the make-up kit in my drawer and kept the brown bag on my bed, I received a notification from Ms. Robin that she had mailed the video. I removed my clothes and only kept my panties on, switched on the computer called Ms. Robin and played the video after wearing my headphones, the video was titled "Beauty and Cock". Images of pretty sissies and big cocks flashed, the sissies were dressed in slutty clothes they told how they loved dressing slutty and how they loved sucking big cocks, again I went into a trance I was watching it with full concentration, I had thoughts of looking slutty I wanted a big dick in my mouth I wanted to swallow cum, the video played on and my desires got stronger.

To be continued....

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
doninpantiesdoninpantiesover 1 year ago

Great story. Can’t wait for the next chapter. Oh yes had to change panties they got wet

slavetobyslavetobyover 2 years ago

This is a very very exciting story and I am looking forward to reading more. Thank you so much for sharing this with us

bottomboitoserveyoubottomboitoserveyouover 2 years ago

I'm loving your story so far...would have loved to have someone like Mistress Robin guiding me when I was growing up!

SamanthaSatineSamanthaSatinealmost 3 years ago

Thanks for creating and writing this story for us to enjoy as I have so far myself xxx

dressingSaradressingSaraalmost 3 years ago

Great Story!

Love your story, I really wish I would have had a teacher like that in my school time. Cant wait for you to continue.

Share this Story

READ MORE OF THIS SERIES

Sissified Ch. 02 Previous Part
Sissified Series Info

Similar Stories

Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Social Media Star Boy becomes an unwilling lingerie model for online viewers.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
More Stories