Prison Sissy Cuckboy Ch. 01

This story has homoerotic and forced-sex themes. If you are offended by such, do not read.

All characters in this story are over the age of 18. The entire story is fiction as are all characters. Any likeness a character has to someone in real life is merely circumstantial.

This story may not be copied without the direct permission of the author (me!)

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Prison overcrowding in the US had gotten out of hand by 2027. Management of their operations fell into chaos as fewer and fewer guards were posted. Less order meant more prison deaths and even more criminal activity inside the walls. The government turn their back on the prison's and on March 3rd 2027 guards were withdrawn from the prison interiors completely.

Tim had heard the stories of the inside of Rothwell Penitentiary and dreaded to think what was beyond those walls. He, along with 14 other new inmates, got off the transport. They had been driven the 1 mile distance from the outer wall to the main inner wall.

Tim looked around at the other inmates. Some were like him: small, spindly pale men, who had been sent away for white collar crimes, though they were in the minority. Of the 15 men, 12 of them were larger muscled gentlemen: mostly black, with gang-affiliated tattoos.

The final gates swung open and the guard came around to un-cuff each of the prisoners in turn. Tim was the last one and wrang his wrists upon having them freed.

"Good luck", the guard muttered, turning away to board the transport.

A horn blared and everyone started to move towards the open gate. It towered over them, walls 30ft high either side, topped with barbed wire. Tim was the last through the gate and the automated shutters closed behind him. He heard the transport drive away as he wandered out into the courtyard for the first day of the next 3 years of his life.

All eyes were on him and the other 14 new inmates. A few of them walked with purpose to join groups of others standing in the courtyard, clearly having existing affiliations to the prison gangs. A couple of the men hesitated, looking around carefully before moving toward their desired group.

Tim noticed that most of the gangs were race-orientated and saw a group of white skinheads at the far-side of the courtyard, away from the entrance. He started toward them but barely got 10 paces before being cut-off by another group.

Towering over him were as many as six large black men. The one directly in front of him spoke first. "Looks like we found our next bitch."

Tim took a couple of steps backward, panic starting to settle in. He looked behind him and saw one of the other white-collared inmates being approached by a similar looking group.

"Hey, bitch," the gang leader shouted to Tim, "look at me when I talk to you." Tim's head whipped back around to look at the gang, who had stayed where they were, not advancing any further.

"OK bitch, this is how it's gonna be. You either come willingly, or you get this." He pulled out a large knife.

A high-pitched wail came from behind him. Tim whirled around to watch the other white guy fall to the ground, his white vest turning red.

"I said look at me, bitch." His shout came as a command and Tim turned to face the gang leader, who had taken a step toward him.

"Ok, ok," Tim pleaded. "Yes, I'll come willingly. I'll join your gang."

The group all laughed.

"Join?" the leader said, with a grimace. He took another step, so that he was now directly in front of Tim. "Kneel," he commanded, looking down.

Tim obliged. If this guy wanted him to play like he was king, then that worked fine for Tim, as long as it kept him safe. To his horror, however, the gang leader pulled down his shorts.

Tim stared forward at the largest cock he had ever seen in his life. It must have been 9 inches and was still semi-soft. He compared it to his own in his head, thinking it must be at least three-times the length of his own.

"Open."

Tim's mind had stopped working. Self-preservation kicked-in and he felt himself open his mouth wide.

The leader smiled and guided the head into Tim's mouth.

Tim had never sucked a cock before. He'd had no homosexual tendencies. But at this moment, he knew that this blowjob was the only thing that stood between him and death. He considered quickly all the porn he'd ever watched, the escorts he'd had in hotel rooms, his wife that was unmatched in the art of giving head... He reached up with both hands and began to massage the base. He the cock to the back of his throat hard, so to fill his mouth with saliva. He pushed his tongue out to sit above his teeth.

"Oh, shit. This bitch is eager," Tim heard the man say as he put his hand on the back of Tim's head.

Bobbing his head back and forth, wringing out his monster cock with his hands as he did so, Tim was clearly doing a good job. The man moaned audibly and Tim could taste the salty taste of pre-cum at the back of his throat.

It came quickly and without warning. So engaged with the action of pleasing the man in front of him, Tim didn't notice the men beside him until he was already lifted off the ground and was carried by these two men. The cock was pulled from his mouth, saliva running down his face.

He looked franticly around him. Few people were looking in his direction. He saw the man who had been stabbed, laying still on the ground. He saw another man, like himself, mouth open, being face-fucked by a latino gang member.

He was carried through an open arch and into a nearby building. From there, he was carried for about 10 minutes through a complex of corridors and cell blocks. Tim stared around at the overcrowding in the cell blocks. Whereas the entrance yard to the prison had been sparse, the cell blocks were not. In the short time that he was brought through the cell blocks, he must have seen over 1,000 inmates.

They came to another door, though this one was apparently locked. One of the men gave a wrap with his knuckle on the door and a voice from the other side spoke. "Who?" it asked.

"Herk," the man responded. A second later, a latch could be heard and the door swung open. They stepped through, almost hitting Tim on the doorway, twisting him just in time to squeeze through the entrance.

Finally, the men set Tim down. Adjusting to his surroundings, Tim looked around. Much like the other cell blocks, this one was too, overcrowded, though perhaps less-so. He saw mostly large black men around the communal area, but with a few white... WOMEN? Several girls were sat on the laps of the black inmates and Tim even saw one of them bent over in doggy in the far corner, taking a guy in her mouth and up her pussy.

It took a few seconds before it dawned on him. Looking closely, he could see that the 'women' were not women at all. They had tiny little devices on their cocks - they were other inmates. They were LIKE HIM. His reality began to settle over him like a cloud. He almost felt weightless as he grew lightheaded at the thought.

Clearly with disregard for giving him time to process, Herk pushed him forward. They moved through the common area and up to a large room on the far side. The door to the room was painted pink. Tim was pushed inside what seemed to be an old locker room / shower, the door closing loudly behind him.

Inside, he had ample company. There were several of the 'girls' here. He must have had a 'deer-in-headlights' look, as they approached him slowly.

"Hey sweetie," a particularly chubby one said to him and touched his arm. "Why don't you come over here so that we can get you settled in?" She beckoned him to a bench beside them. Tim sat down and was immediately swarmed by all dozen girls in the room.

"I'm Candy," the chubby girl said to him. "This is Mia, Rosie, Luce, Daisy,..."

"What is this?" Tim spoke for the first time since stepping off the transport.

Candy gave him a tender look. "This is how it is in here sweetie. You must have given some good head, because Kong doesn't allow just anyone into Apex."

"Kong?" Tim said, shakily. "Apex?"

"Apex is the gang, babe," Daisy chimed-in.

"Yeah, and Kong is one of the leaders," Rosie continued. "Though there are 4 in Apex. It's so big, aye."

"Be happy you got into Apex," Candy consoled Tim. "This is about as good a life a sissy can have in here."

"A... " Tim started

"A sissy is what we are, babe," Daisy interrupted him. "You know, a girly-boi."

Tim felt sick. He must of looked it too, because Candy suddenly ushered for the girls to disperse and give him space. 'A sissy,' he thought. Is that what he was now?

"Now," Candy started, speaking softly. "We have about 2 hours to get you ready. That's usually how long they give us for newbies, anyway. There's a lot to do in that time..." she trailed off, looking him up and down. It was at this moment that Tim noticed Candy's puffy breasts.

"Do I need to g-get breast-ts?" he stuttered at her.

A compassionate look crossed Candy's face. "No babe. I take hormones for these," she cupped her tits in either hand, "but we will need to pump them a little to make them plump. The men prefer that."

Tim just looked at the floor, breathing slowly.

Candy left him for several minutes. One of the other girls came over, with a large duffle bag. "OK, that's enough time for processing," Candy started, "we really can't waste any longer. Unless you want to have your first day be a beating, we better get you fuckable." Tim's eyes grew wide at the mention of being 'fucked', but Candy brushed passed it. "Now Becky needs to fit you for a cage." She gestured over at a redhead girl, who was rummaging through a box of assorted metal pieces. "Will you cum faster from a blowjob or from sex?" Tim just looked at her bewildered. She rolled her eyes and gestured at one of the other girls. A little asian walked in front of Tim.

"What position?" the girl asked Candy.

"I suppose it depends if he snaps out of it and makes use of his last chance for sex or not," Candy said looking at Tim. "Well?!" she yelled at him, making him jump. "This is it... What was your name?"

"Tim."

"Well Tim. This is your last day with that name. This is your last time to actually do something with that dick of yours, so make a decision, or I'll do it for you." She looked expectantly at him. "What position do you want Amy in?"

Tim looked to the 'girl' in front of him. The girl that was really a boy, with a locked-up penis. He wasn't gay, but Amy was very attractive and from behind, there was no way to know that she was really a boy.

"Doggystyle" he said, simply.

"Finally! Some words!" Candy smiled. Amy turned and grabbed her ankles. She didn't even wait for him to edge forwards. He stayed still as she backed up onto his semi-erect cock.

Her ass was lubed-up well and he barely felt anything sliding in, how gaped her ass was. All of a sudden, he felt her squeeze his cock with her sphincter muscles and his cock instantly got harder. He made an audible gasp at as she began to grind in front of him.

Distracted, he hadn't notice all the girls moving around him. "Going in," Mia said in his ear, as she slid something slimy and cold up his ass. His cock throbbed at the additional pressure and he felt his anal cavity start to bulge as water filled him up. During all of this, Amy was still grinding away. She looked almost bored at servicing him, but it was some of the best sex he had ever felt.

The hose popped out of his ass and he felt the water (mixed with other less-clean materials) pour from his ass onto the floor and seemingly down a drain. The additional stimulation was too much and after less than a minute of sex, Tim let out a grunt as he ejaculated into Amy's ass. After cumming, the girl with the box of metal rushed over to him, holding his slimy cock in her hand.

"He's still got a semi," she said to Candy, who looked back at Tim, disapprovingly.

"For fuck sakes." She grabbed him by the arm and dragged him over to a nearby table. It looked like a massage table, but as he was pushed onto it, he was directed to lie with his cock over the open head-hole (upsidedown).

Becky, Candy and a few other girls now all held him down. "This needs to happen Tim. We need you as soft as possible when we fit you, or we all get punished." Candy said to him in a warning tone.

Tim heard the sound of a drill and immediately began to panic and wriggle, but was no match for the group of girls pinning him down. Very quickly he learnt that it wasn't a drill at all, as he saw a dildo-machine of some kind being brought up next to him. Next someone was applying a plentiful helping of lube to his ass. He could see where this was going...

His entire body tensed-up. His ass parted slowly to the dildo, but just as he started to feel the pain, someone began to suck on his cock. He lifted his head off the table to look up. Directly in-front of him was Amy, bent over with her freshly-creampied ass right in his face. "Eat it," Candy said as he stared at his messy cumload spilling from her ass.

"No." At his word, the dildo machine was turned-on and began to fuck him much faster and deeper than a virgin should need to go.

"You'll need to learn eventually and we're starting to run low on time."

"No." Tears of defiance in his eyes, Tim felt the depth of the fucking increase. He let out a shout of pain and 'was that pleasure?'

"Eat it, or I swear I'll rip your hole open. I can warm you up, or just split you open."

Tim closed his eyes. Opening his mouth, he began to lap up the cum from Amy's asshole.

He hadn't noticed, but with all the postate stimulation and the top-notch blowjob he was getting, he was close again to cumming. He was right on the edge, when Amy squirted the last of his cum from the depths of her ass into his open mouth. She covered his mouth and nose with her hands and without thinking he swallowed the load. He was sent over the edge.

He had only just cum moments before and all it seemed his body could muster were a few measly ropes of cum. The cock in his ass was quickly pulled and he was spun onto his back.

"Ok, let's get it on." He could feel the girl Becky fiddling with his limp cock.

One of the girls appeared beside him and went to give him a french kiss. Instinctively, he opened his mouth, only to receive a full mouthful of his last cumload. He looked up at Candy who stood nearby, eyes tearful once more. She gave him the look and he swallowed the load without further protest.

It wasn't long before his chastity cage; that's what they called it, had been fitted. Fortunately for him, they didn't need to do much shaving, as he was naturally quite hairless; though he was subjected to a full inspection with razors as several girls traced over every surface of his body. When they got to his ass, they not only shaved, but also dabbed some bleach on his sphincter, which they left to sit there for the remainder of his transformation.

It felt like a pit-stop crew. There was a girl on his hair, another 2 on his make-up, 1 was sizing his feet for shoes, 2 were picking him an outfit... Candy talked continuously, orchestrating the whole design. Amy, the asian he had just fucked, came over to kiss him. This time, there was no taste of cum; which was a relief. Tim was, however, taken aback by the action. She stopped for a second and looked down to him. "I just really liked that fuck. You've made me a little horny," she giggled and continued kissing him.

Candy sighed, but made little effort to stop her. Amy kept out of the way of the other girls who were working and as they started working on Tim's makeup, she moved behind him and began to lick his ass.

Tim's newly-bound cock strained against his cage as he felt her tongue flicking against his asshole. The whole experience was starting to feel very surreal, made more so with the heavy layers of makeup that caked his face.

By the time they were finishing up, he was unrecognisable. He looked as feminine as the rest of them, if not even more sexy with all the extra attention. His skin felt soft, waxed and now coated in lotion. His hands and feet were fitted with new stick-on nails. He looked himself in the mirror and admired how cute they'd made his face. He looked like a bombshell, topped with a long blonde wig.

"I went with blonde, as that's Kong's favourite," Candy said as she held the mirror in front of Tim. "He also likes his sissies to be in pink."

Tim could tell. He was dressed in almost nothing but pink. His cage was pink. His high heels were pink. His satin panties, bralet and stockings were all pink. One of the girls, as yet unnamed, was walking toward him carrying a pink latex cocktail dress. He lifted his arms and the dress fell over him, fitting his form perfectly.

"Morale is important in an ecosystem like this," Candy went on. The men need something to look forward to; something worth behaving for. The threat of violence isn't enough to keep everyone in line, but a good hooker..." she trailed off.

Is that what he was now? - A hooker?

"Now, we have 30 minutes to get you prepared."

Tim looked up at her, confused. He thought he was prepared... What was all the clothing for? Clearly seeing his confusion, Candy clarified: "Looking the part is important, but if you aren't able to handle the cock."

Tim's heart stopped. He'd almost forgot that he'd have to actually perform.

"We'll take you through how to give a good blowjob, but really what we need is to get you stretched open so that you can take it up your ass."

Tim felt himself clench and wince at the thought. Candy simply ignored him and continued.

"Come over here," she gestured over to the table where he had already been fucked once. Slowly, he shambled over in his oversized heels. Candy positioned him in front of the table, before bending him over it.

"OK, good. Look ahead and we'll get a toy for you to choke on. Whilst you're doing that, April will work on your ass."

He felt his satin thong being pulled down to his ankles and something wet and cold begin to invade his hole. Amy was back in front of him. She brought with her several dildos. Not wasting any time, she pushed the first of them into his mouth and straight to the back of his throat. He began to gag.

The training stretched on and it felt a lot longer than the 30 minutes before they were done. His asshole had been slowly gaped wider and wider, until April; a particularly fat girl with big tits on display, had stuffed his ass with a huge red butt plug. Whilst that was going on Tim had barely had any time to protest, as his throat was getting the workout of its life. He had gagged and vomited multiple times, but each time, unrelenting, Amy had just continued her attack. Afterward, his makeup was redone somewhat.

The time had come. Candy turned Tim to face her. Like the scared little girl he was, she gave him pitying eyes.

"You'll be fine," she said, unconvincingly. "He likes to put on a show, so just remember to actually play along. Call him 'daddy' and moan like a bitch in heat if you want to do well." She gave him a little kiss on his cheek. "When you're done, we'll clean you up nice and you'll get a little break. I know it's been a lot."

She went to walk away, but then turned with an afterthought. "You'll need a name," she said.

"I'm-m Tim," Tim said shakily.

She smiled gently at him. "You'll need your sissy name. We can't call you that in here."

Tim just looked blankly back at her, unsure what to say. What name should he pick for the next 3 years of his life?

After a few moments, Candy interjected "what about Tamara?"

He gave her a look to indicate that it was as good as any. Again, Candy looked at him-now-her with pity.

The door from where Tim had come now opened-up again. Lead by Candy, Tamara left to go meet the gang leader: Kong.