From Brother to Bitch Ch. 02

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James becomes a sissy start.
7k words
3.68
107.2k
38

Part 2 of the 2 part series

Updated 10/08/2022
Created 02/09/2011
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James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares.

He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling he used to do during sleep because of sucking the thumb.

He goes up and went to make himself ready for the school. He slipped into his favorite black colored shorts and went into the living room and grabbed some quick lunch.

Their parents, both mom and father are employed in an MNC, so normally they can't spend much time with their children. His school was from 10:00, so he needed to get himself ready.

He locked the door of his room and started to wear the uniform. He looked at the underwear, he wanted so bad to put it on, but he didn't obeying the command of his big brother, Vito.

He put on his pant directly over his naked body and wrapped the shirt around him, buttoning them correctly. He opened the door and was about to leave. Because he prefer to go to school by simply walking, rather than driving a motorbike, like his brother.

He opened the door and find Vito standing in front of him, grinning from ear to ear, Vito spoke, "Today, I will also walk my way to the school, with YOU."

He emphasized the word YOU. He added, "I hope you followed your dress code, pull your pants down, now." Vito leaned against the wall to see what his brother is doing, a little bitch for the entire school.

James started to pull his pants down, with trembling hands. He pulled it down below his ankles and lifted his shirt to expose his bare naked cock to him.

Vito slapped his cock gently and said, "Good, now turn around and let me see your cute little asshole."

James obeyed again, after turning his ass towards him, spreading his butt cheek with his hands. Vito chuckled and patted his ass, "Stand straight and pull your pants back. I don't want to see your asshole at the moment. There will be plenty of time for that. "

James pulled his pants back quickly looking at his brother, "So, brother............

Vito frowned and slapped James so hard, James almost felt back. Vito mocked looking at him, "Old habits die hard, huh? You are not supposed to talk around us. You will address us, 'thank you sir', 'yes sir', 'welcome sir' and related. But no other talking, after that you will just obey no matter what. And if you need anything, beg like a dog, don't talk show us the actions of a dog. Got it?"

James was startled from the hard slap that landed on his face. He started to rub his cheek, trying to erase the pain away. His face assumed a pinkish shade, such hard was the slap. James looked at his brother Vito, and looked down, "Yes sir."

Vito smiled, "That's good and another thing, clitoris refers to your cock and cunt refers to your asshole. Just remember it."

Vito opened the door of the house and walked outside, he waited for James, who also followed him quickly. Vito locked the door and slipped off the key inside his pocket, James noticed it. And he realized he can't come inside the house until Vito allowed him to.

James was facing a problem. He didn't pee from morning, so there was a definite urge to pee. But he wanted to wait till they reach school, because at that time, he can pee on his own, during class. Not on the road, this meant begging like a dog. So, he walked quietly.

Vito finally broke the silence and place his hand on the crotch of James', "Soon you will learn to love this, James. Don't worry about it, it will happen pretty soon."

On entering a little lonely road, a shortcut between two major roads, Vito pulled down the zipper of the pant which James was wearing. "Take out your dick." He said.

James simply nodded, "Yes sir." He blushed and took his dick out of the hole in his pant and exposes it to the world. The only comfort was that, the road was empty.

His cock started to get an erection, at this public exhibition. This was what Vito planned to induce the fetish of humiliation addiction into James and he succeeded.

Vito chuckled looking at the erection, "So, you love it, huh little whore?" Vito intentionally called him names, to abuse him verbally, this all can induce the addiction much deeper into James, he knew that and that was exactly his planning. "When we enter the main road, you can put your clitoris back where it belongs."

James nodded simply, they walked straight, without saying a word to each other, and his cock was throbbing from the erection. Soon someone almost jumped him from behind shouting, "Hey James, I heard that you are a little Sissy..... Aww, I can't love a sissy." The voice said in a teasing tone.

Vito turned back in surprise, he didn't expect anyone to come along this road, he noticed a person who jumped James is a cute doll faced girl, with deep blue eyes and black hair, curling all along her white cheek.

Vito couldn't help but feel a little sad for James, because there was a chance for him to be a lover of this girl, so there was no chance, he is a bitch.

James's heart froze as he heard the voice. Without the mistake it is the voice of Sophie, the girl who is kind of his lover, he looked at Vito and looked at his cock, waiting for permission to put his cock inside his zipper.

He didn't want to lose the chance to be lover of Sophie. But what James didn't realize that, a bitch can't choose the way he lives. He had to follow the orders and orders only. And right now, he realized the power of Vito and his friends; he didn't want to get another set of beating unnecessarily.

Vito just shook his head and turned to Sophie, "I am sorry Sophie, but James can't reply to you now. He is right now for the time being, bitch for the TRUMP Association."

He turned to James, "Yes, me and my friends belonged to the TRUMP." He continued, "So you see, he will be slave for the entire school for the rest of his academic years."

Sophie frowned and looked at James with a disgusting look, "So, I spend my time around you, a sissy bitch, who loves to take it up in the ass? And see you don't even have the tiny respect to keep your erection inside your pant, you think world appreciates when sissy like you announced, 'hey look I have an erection'?"

James was dying from humiliation, he didn't know that everything is being recorded via the secret spy camera; Vito was hiding in one of his front shirt button.

After all TRUMP made videos of their slave each year, which they used to sale, rent to people and obviously make sure everyone in the school watched it, so that the slave's life becomes horrible.

Sophie turned to Vito and said in plain, simple voice, "I know that slave for TRUMP means, slave for boys only. I have no objection against it; in fact sissy like James should love it. Anyway can I get the videos of him? I know that TRUMP releases these slave videos every year."

Vito smiled and said, "You don't have to worry about it. It will be done anyway. After everything he will be forced to do. He won't be able to act like a normal person ever again. He will be a pure sissy slave." He was happy inside too, because this video of Sophie talking to him, about the video can be a great advertisement for their product. He added, "So, would you like to walk with us or wanna go separately?"

At this point, James tugged the shirt of his brother Vito a bit and pointed at the lamp-post once then at his cock. He was blushing all the way, as Vito smirked, "So bitch needs to take a leak right now. OK, go ahead, do it like a dog, lifting your leg up."

James once looked at Sophie; she was waiting for James to do it, with an obvious smile of her face. She even started to humiliate James further verbally, "Come on Dog, go and pee. Doggies can't hold their pee like humans, you know. They pee wherever they can, when there is an urge. Go James, before you start to pee on the road just standing like this."

James swallowed a bit, and got all on his fours, crawling to the lamp-post like a dog. When he reached there, he turned his face to see Vito and Sophie are giggling at him, while he lifted his leg up like a dog and started to release his bladder. He closed his eyes and sighed when his bladder felt light again. He crawled back to them and stood up like a human again.

Vito patted James on his head and smiled, "Good bitch." He turned to Sophie and repeated his question once again. He was really hoping that Sophie would walk with them, in that way he can humiliate James much more. But it didn't happen this time.

Sophie looked at her watch and said, "No, I can't go with you two. Actually my friends are waiting for me, so bye for now." She turned to James and smiled, "Best of Luck James, you are going to need it." She waved her hands and started to walk away, not even looking back at James for once.

James was heartbroken; he couldn't believe that she practically dumped him, without even considering his perspective. His cock was hanging above the zipper of his pants, without any life in it. He was so bummed from all this. And also the idea of being shown to everybody via a video made his mind even worse. He slowly turned to Vito and said in a sad tone, "I don't wanna go to my class and face her another time."

Vito excused him this time for talking without permission. He wanted to transform him slowly, sometimes allowing him to do something that actually deserves a punishment. He patted the cute butt cheek of James slowly and said, "Its OK, you can stay in the Boy's common room all the time. And we are approaching the main road; you might want to keep it inside."

James blushed and put his dick inside his pants and pulled the zipper back, he turned to his brother, looking down a little, "Thank you, Sir." As he continued to walk along the road, not even looking up to all the people walking, driving on the busy road, he kept on thinking about his life.

Both of them entered their school, and walked towards the Boy's common room, or in fact the TRUMP club. James was thinking about whether to enter the class for now, or to surrender to the TRUMP group right from the beginning of the day.

He was walking towards his class, when he heard, a girl named, Jenna, talking to her boyfriend, "I have no interest of losing my virginity, if you wanna fuck someone, fuck James, and he is quite a sissy I heard." She didn't notice his classmate standing at a little distance from them. When she noticed, she bit her lips and said, "Sorry James, but everyone is talking about it, I am sorry."

James just shrugged, "Whatever, It doesn't matter. I am doomed, Jenna." He turned totally 180 and started to walk towards the common room and enter the hall, gently, looking at everybody for order, "Good Morning, Sirs." He simply walked to the middle of the room and waited, surrendering to the fate.

The group cheered and told him to kneel before all of them; James did so without any questions. One of the guy stood up and looked at him, he started, "From this moment, you are no longer a human while our session is on. You are a bitch who knows only one word, sir. If you have any need you must explain it to us, like a doggy must do. No matter how humiliating it is, you are bound to obey, got it?"

James was sweating, beyond his imagination. He wanted to get it over with, though he knew that this is just a beginning of a long story. He said politely, "Yes, sir."

The boy smiled, "Good, now strip off bitch. Let us see your skin. And go sit on the red colored chair."

James obeyed again, stripping off completely; he folded his clothes to one side and sat on the chair placed near the middle of the room. And he waited for the next part. He was nervous inside, but maintained his calm on the surface.

Few of them stood and positioned a camera near James, so that his video can be captured from every angle, without any modesty, revealing everything. The first guy started, "Well, you must answer few questions honestly. This will be tagged under your biography part. So, ready?"

James nodded and waited for the questions, wandering how humiliating it can be. The guy turned the camera on, and there was a deep silence prevailing in the hall.

The guy smiled, and looked at him, "Good, this is a rapid fire type. No deep thinking before answering, unless you wanna redo everything. So, here we go."

Guy: Do you suck your thumbs, while sleeping?

James: Yes.

Guy: How, show us.

James faced the camera and started to suck the thumbs gently, like he used to do every night, before dozing off to sleep. He got a little excited to reveal this, in front of so many, his cock started to harden a bit.

The guy laughed at it, few guys were managing the camera angles and zoom. There were making sure that they are able to capture everything. The guy added a comment, "And this turns on the little sissy whore, as we can see."

Guy: Good work. How many times do you masturbate each day?

James: One to two times, depending on mood. Guy: How big does it get when you are excited completely?

James: Only 5", sir.

Guy: So, I guess you are a virgin?

James: Yes I am.

Guy: So, you have crush on anybody?

James paused a little, and answered: Sophie, my classmate.

Guy: Does she know that you are a sissy inside.

James: Yes, she found out today.

Guy: And probably dumped you right there, am I correct?

James: Yes, sir.

Guy: Do you think you deserve more respect than this?

James: I am a sissy sir, so this is what I deserve.

Guy: Have you ever tried woman's clothing?

James: I wanted to, but didn't get the chance.

Guy: You agree to do anything ordered?

James: Yes sir, I do.

Guy: Great, so tell us who are you.

James: I am James, a bitch for TRUMP

The guy stood up and walked towards James; he patted his head and ruffled with his hair a bit. "Nice start, bitch. Now we are going to take a snapshot. This will be the photo for this year TRUMP SISSY MAGAZINE, so give us a nice pose. Stand on the ground, resting once leg on the chair, and other on the floor, bend forward, just turning your head towards the cameras."

James did it exactly, as he positioned himself like that, he felt the cool air, hitting him on his asshole, with was now exposed because of the leg orientation. He leaned forward and looked at the camera. With a shy smile on his face, it was really cute to anyone who loves sissy. His cock was erect, at a parallel state with the ground, while his balls, were hanging between his legs.

The guy was pleased with his efforts and asked James, "Cup your balls with one hand, while sucking your thumb of the other hand. This will be the perfect pose for you. This will be suitable for your character."

James cupped his balls with his left hand gently while hiding his balls from the camera view this way. He put his thumb of the right hand inside his mouth and started to suck it slowly, while looking at the camera, blushing for real.

One guy brought a bucket of warm water, and poured it above James, to add the wet effect. James stood there still, as the entire hall got illuminated with the strong flash from the camera. The shot was a great one. Vito came to James, and clothed him fast, as they started to walk outside of the room, James was still wet.

They walked outside the room, all of them and closed the door of the common room. They left one poster, "This year also, TRUMP has started making the magazine. For updated news and poster, visit our club, near Central Park."

They, along with James entered into different cars; James was with Vito as they started driving to their club. In the car, James got lots of shoulder patting and people were praising him, for a good start all the way. They arrived after one hour of driving. As they arrived, James saw the club building; his heart froze with complete fear as he read the board, "THIS RENAISSANCE'S UN-NAMED MASTER PUNKS -- TRUMP!" this was the most sexually active club in the entire city. They are into gay as well as straight sex, under different departments.

Vito grabbed his brother's hands with affection, "See, you should be glad to be the main attraction of our magazine this year. You are luckier than most sissies out there, getting their ass rammed around the corner in some dark alley without anyone knowing their name."

James was trembling with pure fear, throughout their life; this one club is what almost everyone is afraid of. James looked at Vito, "do our parents know that you are into this?" He was secretly excited a little, because he used to jerk himself off by going through these magazines, but what made him feel uncomfortable was that he is going to be the cover.

Both of them entered the main building. The inside of the building was vast; it was a 5 storied building. Actually TRUMP was a multi-sex magazine publisher. James and Vito walked to the living room, sort of thing in that building's first floor. Vito ordered casually, "Inside this building you are a bitch, and no bitch is allowed to wear clothes."

James slowly sighed and looked away from his brother; he stripped of his clothing once again. His naked smooth butt came into view of everybody around. James get on all his fours like a dog, as his brother explained to him the other night and looked at him eagerly.

Vito smirked at his eagerness to become a good little bitch; he tilted his head to see the flaccid penis of James. "Good, you did it faster than earlier, slut. Now let me tell you. TRUMP is an international rising sex magazine, we have different departments. Now, sissy magazine is maintained by people like us, just 19-22 years old, and they are guided by one editor."

He continued, "For us, her name is Miss Tulip, she is 25 years old. Now, this year you have been chosen as the sissy boy. Since we release monthly DVD and magazines, so one per month, you have to do total 12 major shots and some personal stuff for us. Any question?"

James shrugged his little cock was starting to have an erection to be naked inside a group of people, all secretly enjoying the view of his butt-hole being exposed to all. James touched his cock a little with his fingers then looked at Vito,"What will be the plot for my first video?"

Vito smiled and extended his left leg, rubbing it gently against the cock shaft of his brother, exciting him slowly, Vito smirked with a little evil grin, "Such a whore you are brother, your clit loves the every second of my touching. Damn, I am touching you with my shoe, what would it do if I touched you with my hands? And for the first shot, you are gonna be present for a birthday boy."

Few boys gathered around James and restrained him to a metallic chair which was resting on four stands, which made it possible for the chair to rotate freely through all 360, vertically by means of pinned junctions. The seat cover of the chair was cut; instead there was a big hole through which his ass passed easily.

Vito slapped his cheek tightly, so that it turned a little pink, and said in a cold voice, "From this point, no more words, from your mouth. Do what you will be ordered without hesitation told to do. " Vito and the boys started to rotate the chair, till James' ass pointed upwards. At the same time, cameras were adjusted all over the place.

A guy took out a long thick red colored candle, with few wordings carved on it, "21st Happy Birthday, Michael." The candle had a waxed grasping surface, like the end of it like a dildo, and it started to spread his butthole apart, while he started to stretch the inner walls of the darkest hole of James. As the dildo got jammed there Vito started to push the chair, the chair was provided with wheels on the four stands.

They reached in front of a door, on the other side of which, clearly a party was going on. Vito lit up the candle and opened the door gently. James was in lot of pain, as hot wax started to drop on his bare ass drop by drop. His cock was throbbing from this public abuse, but mentally denied the sexual excitement.

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