Sissified Ch. 13

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Sissy visits a hotel.
2.1k words
4.67
22.5k
18

Part 13 of the 20 part series

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

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It had been a month since I lost my virginity. I had officially changed my name and embraced my life as sissy. Joe visited mom regularly, sometimes he would have sex with me. Most of the times I would suck him and prepare his cock for mom, then he would fuck her infront of me and I had to clean his cock and mom's pussy after they were finished.

There was a small part of me that wanted to go back to being a boy, but I knew I would never happen. I liked being pretty, dressing up and pleasuring others. I loved my life.

I had my doctor's appointment today, Ms. Robin was going to pick me up. I had finished my chores for today and had to get dressed to go the doctor. I undressed and looked at my body. I had the perfect figure. Small boobs had grown on my chest, my bubble butt looked perfect, my long hair and my smooth face made me look like a pretty girl. I looked at my penis, it was so small and it was caged in a small metal chastity. It had been month since I had been in this new chastity. Every time I got excited it would give me a shock, I tried to control it. Eventually I got it in control, I still get shocked but the number has greatly decreased.

I picked up a short dress and heels. I put on a pink pair of bra and G-string panties and put on the short dress. I put my heels on and corrected my makeup and grabbed my purse. I went downstairs and waited for Ms. Robin. She arrived and I got in her car, she praised my dress and drove to the doctor. We went in to meet the doctor as expected she asked me to strip, I stripped. she examined my body.

"Do you want any changes in your current body?" she asked.

I thought for a while. I didn't want any changes so I remained silent.

"She would really love to get some bigger boobs and a more feminine figure." Ms. Robin said.

"Yes, she would look lovely. I can increase her dosage but there would be other effects." doctor explained.

"Yes, please increase her dosage." Ms. Robin said.

"Ok then, this is your new prescription." she said handing me the prescription.

I kissed her shoes and said goodbye and left. I collected the new pills. We got in her car and she started driving. I noticed she wasn't taking me home she was driving me in the other direction.

"Where are we going mistress?" I asked.

"We are going to the Palace resort." she replied.

The palace resort was a hotel which was very expensive.

"Why are we going there?" I asked.

"Your mother had her fun, getting you fucked by Joe. We had a deal now I get to have my fun."

"What are you going to do?"

"Don't worry you will love it."

She drove to the hotel. We got into our room; it was on the 14th floor. She ordered me to strip and made me wear a wine lacy red crotchless panty and a bra of the same design, she put on a garter belt and matching panty hose. She gave me a pair of black heels and cuffed my hands behind me.

"I have a friend in one of the rooms of this hotel. You will have to search for her, find her or else there will be severe punishments." she explained.

"But mistress how am I supposed to find him there are so many rooms. How do I know where he is?" I asked.

She put a ball gag in my mouth and pushed me out of the room.

"Knock every door." she said and closed the door.

I stood in the hall way with my caged penis exposed. I stood there not knowing what to do.

"I have to find Ms. Robin's friend if I want this to end." I told myself.

I was on the top most floor of the hotel so I went to the first room on the floor and knocked the door. No one answered, there were 10 rooms on each floor. I knocked every room on the floor only one of them opened, it was young guy. As my hands were behind, I had to knock while facing my ass towards the door. When I turned, he looked at me confused and when he noticed my penis, he shut the door. I went to the elevator and got in. my hands were behind me so instead of pushing the button for 13th floor I pushed the one for 1st. I reached down and started knocking the doors. Luckily most of them were empty and the ones who answered closed the door after seeing me. I moved to the next floor. When I reached the 7th floor, I knocked on the doors. One was answered by a huge man, he had just got out of shower and was wearing only a towel. He pulled me in and threw me on the bed and pulled my panties down he licked my ass hole and pushed his dick inside, as he fucked me, I started getting excited, so I got shocks from the cage. I wanted to scream but due to the gag I couldn't. I endured it silently. I had found him this will all be over soon. After he came in my ass, I came at the same time, he pushed the plug inside and stuffed a 100$ in my bra and pushed me outside. I was confused, wasn't he Ms. Robin's friend.

"Did he think I was a slut. he must have that is why he paid me." I thought.

I continued to knock the other doors and went to higher floors. Twice on the 9th floor I was mistaken for a whore and got fucked and paid. I was at my limit my ass pained so much; it was difficult for me to walk. I was leaking continuously, I continued to the next floor, on the 12th floor the same thing happened thrice. When I left the floor, my ass was filled with cum. I had been fucked six times in one day and came thrice. My hole was loose and it was difficult to keep my plug in, not the mention the shocks the cage gave. I somehow reached the 13th floor. It was really difficult to walk now. I kept knocking on the doors, one them answered.

A beautiful woman opened the door, she was in her early 30's. she stood there naked.

"She is here." she shouted and led me in.

Inside there were four huge men on her bed all naked and their huge cocks hard and ready to fuck. She pushed me on to the bed and pulled my plug out, cum started leaking out.

"She is well lubed." she declared.

One the men pushed her aside and entered me and fucked me deep. Another one removed my gag but before I could speak, he pushed his cock inside my mouth. the other two men entered the woman; one in her mouth and the other in her pussy. They continued fucking me my penis was leaking too. They soon exchanged their positions. Other two men came to me and fucked me both in the ass and my mouth. this went on for quite some time. One of them kept fucking my ass while the other kneeled in front of me. They all came together, one in my ass and the others all over my body. He pushed the plug back in, I had to lick their cocks clean. The woman asked me to clean her pussy and I did.

"Can I go back to mistress now?" I asked.

"What?" the woman replied.

"Mistress Robin, she asked me to find you."

"I don't know any Robin, there must have been a confusion."

I was shocked, I just had sex with four men and it was the wrong room, I still had the find the right room. I was too tired to even walk.

"This is for your troubles." a man said throwing me a bundle of cash. I asked them to gag me and stuff the bundle in my bra. As I walked, I could feel the cum in my ass. I felt so full. I knocked the other rooms on the floor, but none answered. I had been tricked. I had been fucked by ten cocks just to find out Ms. Robin lied to me. I made my way to the 14th floor. I was going back to Ms. Robin's room.

"Hey Roxie."

I turned Mom was standing on the door next to Ms. Robin's.

"I'm the one you are looking for." she said.

"Mom I knocked at the door, why didn't you answer?" I asked.

"I wanted you to have some fun. How many times did you get fucked today, must be a lot?"

"Ten times." I replied.

"Wow, that's a lot. I'm sure you had fun."

I did, I loved to get my ass stuffed with cocks.

"Yes, I did." I replied.

"Good, now let us get out of this whorehouse. I still have so much planned for today."

"Whore house?"

"Yes, this is whore house. Didn't you know that. Do you think it is normal to move around the hotel dressed like that?"

It all made sense now.

I got into her room, I removed the cum stained lingerie and took a bath. She gave me a denim short and a small t-shirt to wear. I changed into them. We went to her car and she drove me to a tattoo shop.

"You have accepted your position as a submissive, it is no easy feat to get fucked ten times and to mark this occasion, I want you to give you a gift from the money you earned." mom said.

We went inside and she said something to the woman at the counter. She let me in removed my clothes and asked me to lay on the bed facing down. I lied down on my stomach. She started the tattoo. It pained, but I endured it. After she was finished, she called mom in.

"It looks wonderful, you did a really great job." she said.

I got up and looked in the mirror. It was a tramp stamp. I was a bright pink butterfly on my lower back. Stems of green with red roses on them branched out from both sides of the butterfly.

"Roxie, the butterfly is a street slang which means you like it in the butt and the red roses signify your position as a submissive sissy. It represents you perfectly. Now, thank her." mom explained

I kneeled down and kissed the woman's feet, I got dressed and we left. We stopped at a shop and she bought me a lot of jewellery; necklace, huge slutty earrings, rings and bracelets.

"You have become such a butt slut, you must look like one." mom explained.

We left the shop and went back home. I went back to my room and pulled my plug out and cleaned the cum. I waited for Ms. Robin to arrive for her classes in the evening. She came around 7.

"Love the new tattoo, it suits you." she said.

"Thank you, mistress."

"How's the cage, do you get shocked often?" she asked.

"No, mistress. It has decreased now. My clitty doesn't get excited now."

"Good."

We started studying. She taught me different sex positions and how I must focus on every body if I'm in a gangbang. This what she taught me how. Her classes finished and I kissed her feet. She left.

I went down for dinner; I saw Mom and Ms. Robin discussing something. When the noticed me, they smiled and Ms. Robin left.

"What were you talking about?" I asked mom.

"About your birthday. You thought we forgot."

It was my birthday next month and they were planning about it. I wanted to know what they had planned, but I didn't dare to ask them.

I had my dinner in silence and then went back to my room. I lied on my bed. My ass was burning, it pained so much. It was stretched ten times today. I had become such a slut, taking 10 dicks up my ass in a day. So much had happened in nine months. I fell asleep.

To be continued...

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3 Comments
awyldsideawyldsideover 2 years ago

What a fabulous mother! Pimps out her own son.

Can hardly wait until she castrates him herself!

AnonymousAnonymousover 2 years ago

That was unusually whore-ifying twist to the story.

AnonymousAnonymousover 2 years ago

Loving the story so far. I hope there's going to be breast implants in Roxie's future.

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READ MORE OF THIS SERIES

Sissified Ch. 12 Previous Part
Sissified Series Info

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