Sissified Ch. 14

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

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It had been three weeks since the hotel incident, I woke up and got dressed in my maid uniform. It was my life now. I had changed my name officially on all documents. I was my mother's maid; I did all the house work. Sometimes she would ask me to pleasure her licking her pussy, sometimes Joe would visit and she would make me watch them having sex. I would lick them both clean. if I was lucky Mom would ask Joe to fuck me, this was the only time I had an orgasm. So, naturally I was horny all the time. I also had to serve Ms. Robin; she would take me to random places dressed as a whore. I would give blowjobs and sometimes even let them fuck me, just to pleasure Ms. Robin. I had accepted my place as a sissy in their lives. Due to the new cage, my penis rarely got excited even if I was horny. I would get shocked once or twice a week even less sometimes. My ass was my only source of pleasure now as I had been locked for quite a long time. I still had my gym membership and went there three times a week; I had to maintain my figure. Mom had left early today so I went to the gym. After returning I had a bath and went to my room.

Mom rushed into my room.

"Do you know what day it is?" she asked.

"No, mom."

"Oh, you dumb sissy. Its Halloween today."

"Yes, I remember now."

"We have to get you a nice costume." she said.

"I'm not a kid anymore, I don't want to go out dressed."

"Nonsense you are still my kid and I want you to celebrate it."

"OK, mom."

"Get dressed." she said and left.

I put some casual clothes. A pink crop top, mini skirt and my pink heels. I went downstairs to meet mom. We got in her car and drove to a shop, which I recognized. It was 'deep desires', the sex shop I got my toys from.

"I thought we were going to buy a costume." I said.

"Yes, we will buy it from here. As you said you are not a kid anymore, so you can't dress up in the childish costumes, you must wear something more womanly."

We went inside and were greeted by Ruby.

"Isn't that my favourite sissy. What can I get you today?" she asked.

"She Is looking for a Halloween costume." mom told her.

"Wonderful, do you have any preferences?"

"Something that would let her show inner self."

"I have a couple of costumes you might like." Ruby said and went inside.

She came out holding four costumes. The first one was a classic princess Leia slave outfit. The next one was a Harley Quinn outfit; it was a full sleeve crop top with daddy printed over it and a micro denim short. The third one was a slutty nurse and the last was a wonder woman costume.

I loved the Harley Quinn outfit, but stayed silent and let mom decide.

"The Leia and nurse are really boring, these look good." she said picking up the Harley Quinn outfit. She examined them.

"Mom I like those, can we get them please?" I said.

"Yes, they look good but they are not revealing enough, I want you to show yourself to everyone. These are perfect." she said pointing at the wonder woman costume.

I hadn't seen that costume as I already liked the other one. She picked them up and I saw it for the first time. it had a deep cut bikini top with the wonder woman colours, the skirt was so short it was just two inches in length. It had a tiara with the logo, a pair of boots and a small cape.

"I can't wear this." I said.

"Why, these will look so good on you." mom replied.

"But mom."

"I won't argue this is what you are wearing today, please pack them."

"With pleasure." Ruby replied. she handed us a bag.

"Thank you." mom said.

"I have put something extra inside, for my favourite customer." she said and winked at me.

I kissed her feet and said goodbye. On our way home we stopped at the saloon to get my hair and nails done.

"I want you to look perfect today." she said.

We went back home. I freshened up, it was already 6 and mom called me to her room. She had laid my costume oh her bed. She helped me with my makeup and then asked me to put the costume on.

I put the skimpy top on, then I pulled up my skirt. My chastity was clearly visible so was my ass, I felt exposed.

"Mom can I put on a panty?" I asked.

"It is a part of the costume?"

"No, but my clitty and ass are completely visible."

"So, what. You are sissy you must let everyone know that, now put on the rest."

I pulled up my boots and wore the cape and tiara. I looked in the mirror, I was looking like an actress from some wonder woman porn parody.

"You're forgetting something." she said pulling out a box. Ruby's gift. She opened it; it was a large buttplug with a wonder woman logo. Mom removed my butt plug and pushed the new one in, it stretched my ass, filling it completely.

"You must visit every house in this locality and don't stop them from touching you."

"Yes, Mom."

"I have a gps tag on your clothes, so I will know if you really visited every house or not."

She handed me a pumpkin basket and let me out. I felt the cold breeze on my genitals. Dressed up like this in the middle of the street, turned me on. I went to my neighbour and knocked on the door. Mrs. Smith opened the door, I hoped she didn't recognize me.

"A bold little outfit, I must say." she said.

She looked at the cage and gasped, she realized what I was.

"If not for the cage, I never would have thought you were a boy."

"Thank you."

She put some candy in my basket. I turned to leave.

"What is your name?" she asked.

"Roxie."

"Do you live nearby?"

"Yes."

"Where is your house?"

I didn't know what to say. I was thinking when she suddenly moved closer and looked at me.

"I know you, you're Ron. Esme's son or should I say daughter."

"Yes, it is me." I said trembling.

"What happened to you?"

"I am trying to find myself." I replied.

"Do you like being a sissy."

"Yes." I replied confidently.

"Good. My friends in this neighbourhood would love to know about it."

I was scared, everyone would know about me. I couldn't do anything about it, so I thanked her for the candy and turned to leave. She gave me smack on the ass. I visited the other houses. If the house was opened by a woman, she would already know me and give me candies and then would touch my boobs or ass and then let me go.

If it was opened by a man, they would scan me from head to toe, take a photo and then give me candies, I felt humiliated by all this. One man even tried to grope my boobs, I let him. I was groped by several people that evening. I moved to another street, when I was returning home, it was already dark. I made a turn; it was completely dark. I was walking when I heard someone talking, I looked around. I saw three shadows in the darkness, they noticed and walked towards me. I could see their faces clearly now. They were my classmates; Jamal, Frank and James. They were the ones who used to bully me at school. They came closer and looked at me, I could understand what they wanted.

"Hey, cutie." Jamal said.

"Hello, Jamal." I replied instinctively. I shouldn't have done that.

"How do you know my name?" he asked.

I remained silent. James came closer and looked at me closely.

"I think I know her from school. I just remember her name."

"Same, I think I know her."

"Who are you?" Frank asked. I remained silent. Jamal lifted my face.

"I know her. Its Ron."

"Ron, the skinny bitch?" Frank asked.

"Yeah, its him. Look at him all dressed up, finally he found his place." Jamal replied.

"Yes, its him." Frank and James said together.

They were all jocks, they were huge and strong, I knew I could fight them so I gave up.

"What are you, tell me?" Jamal asked.

"I'm a sissy." I replied meekly.

"Good, you know your place." he said slapping my cage. It hurt, I let out a moan.

"You like it huh?" he said and slapped it again.

He grabbed my ass and smacked it hard, Frank came closer and groped my boobs. Jamal pushed me to my knees and unzipped his pants, his huge cock came out. He grabbed my head and thrusted it inside my mouth, others removed their pants and came closer. I grabbed them, each in one hand and jerked them while Jamal fucked my mouth. Jamal pulled his cock out and went behind me and lifted my ass up and pulled out the plug and threw it away. He slowly entered me and pushed deep, by now Frank had moved his cock into my mouth. I was still jerking James's cock. Jamal continued fucking me James took out his phone and clicked a photo of me, giving blowjob to Frank and getting fucked my Jamal. Jamal kept fucking till he came in my ass, he pulled his cock out, James took over and started fucking me. He too came in my ass. Now Frank came and pushed his cock against my ass. his was the biggest. As he pushed his dick inside, I let out a moan. I was leaking uncontrollably now. There was a pool of my cum beneath me. He kept fucking me and came in my ass. I came, squirting ropes of cum.

I sat on the ground with my legs spread my cage on complete display with cum oozing out of my ass, cum leaking trough my cage. They all click pictures.

"She came from getting fucked. Such a butt slut." James said.

"Clean our cocks now, sissy bitch." Jamal ordered.

All of them put their cocks infront of my mouth and asked me to look up. Then they clicked a picture. I licked their cocks clean, they all jerked and came in my mouth and all over my face.

"Don't swallow." Frank ordered. They all clicked my photo with my face covered in cum, mouth open filled with cum. They pulled their pants up and left without another word.

I walked home, cum leaking from my ass, they had thrown my plug away. I reached home and knocked the door. Mom opened the door.

"Look like you had fun."

I didn't say anything. I went up to my room and cleaned up and lied on my bed naked. I thought about what had happened. All my neighbours knew about me. Jamal and others fucked me and clicked pictures; they would definitely tell everyone about it. Just then I received a notification.

Jamal had uploaded a photo. With shaking hands, I opened it. it was captioned Halloween was hot. I was stiff with fear, it was my photo with cum in my mouth, he had also tagged me. Soon after Frank and James uploaded pictures, me siting on the streets with legs apart and cum oozing out of my ass, the one where they were fucking me both mouth and ass. Jamal also had uploaded a video of me cumming while getting fucked by Frank. All of them had tagged me.

Soon I received messages from my class mates, some flirted with me, some were direct and asked me if I will let them fuck me. Some demanded photos of me. All the girls commented "Sissy" and messaged me telling me how cute I looked and had made the right decision. They invited me to their house parties and said they would love to have sissy like me at the party.

I was overwhelmed I didn't know what to do, every one about me now. Fortunately, I was home-schooled now so I wouldn't have to meet them. But still all my friends knew about me now. I didn't think much about it. I was tired and went to sleep. As I drifted to sleep, I thought about how my life will be from now.

To be continued...