Prison Sissy Novels & Stories

Kaia’s POV The air inside the prison was always dry. A recycled kind of dead—too clean, too sterile. It clung to your throat, clashed with memory, and stripped even the fiercest anger down to silence over time. But today, silence wasn’t an option. Not after he walked out. Brian. With that smug, righteous look on his face. As if telling the truth earned him a redemption arc. As if he hadn’t once been just as greedy, just as complicit.

"You silly girl. "You already saved me."

"Your wife?" "The woman whom you asked if she had a boyfriend, moron. That's my boss' wife." Sebastian butted in at the right moment. "Additionally, leave her little sister, too, if you still value your life." The inmate gulped while his whole body was still pressed against the cold wall. "And, what if I don't?" The inmate really had to ask like a halfwit. Dionysus laughed once again, like the pawn of Satan that he really was. In an instant, Dionysus freed the inmate's neck and even fixed his uniform. The inmate looked so confused as he faced Dionysus again. He was mildly trembling as he made eye contact with the most relentless, secret mafia lord. "Can I go now?"

No matter what it takes or what it costs, I will ensure your safety and help you reclaim everything that belongs to you. … The next evening, Cyrus, Alyssa, and Jonah were in the cellar of Heightsnew Villa. "What did you say? They had a fake prisoner take his place?" Cyrus raised his brows in shock. He was so surprised that he almost crushed the wine glass in his hand. "Did they fucking think the surveillance system in Solana City's prison is just for show? Are they trying to bring The Shawshank Redemption to life?" Alyssa swirled her wine glass while propping her chin up with her other hand. "It sounds more like The Shawshank Exchange to me."

Our names often overlap, and we tend to add physical features to distinguish one another. I step into the basement and switch on the single light. The bulb dangling from the ceiling casts a dim glow over the man tied to the chair. He’s bloody, covered in bruises and cuts, his clothes dirty and torn. Hair filthy, skin covered in filth. He’s been sitting in his own piss and shit for five days. Keeping a prisoner this long is risky. With each passing day, they get another chance to escape, to be discovered. We were lucky. “I hear they call you Vinnie the Nose,” I say as I lazily unbutton my jacket. “Walked around the city bragging about killing some kids. Is that right?”

"Maybe we can create a new sensation here." Tiffany glanced at the two inmates who looked rough, even appearing to be same-sex lovers, making her shudder at the thought of having to stay with them. "You're disgusting," she whispered with a sneer. "What?" One of the inmates stood up and then approached Tiffany with her hands on her hips. "What did you say? We're disgusting?" Tiffany chose to stay silent and turned her face away. "Listen to me!" the other prisoner shouted, pointing at Tiffany. "You say we're disgusting, but you're no different from us because you're here. If you weren't disgusting, you wouldn't be here!" she continued, glaring.

At first I couldn't see anything. It was too dark. But after squinting... I realized those weren't shadows. They were people. People locked inside prison cells. It was a dungeon. The prisoners sat curled into themselves. Weak. Bruised. Half naked. Covered in wounds. Sofia moved closer to me. [Do you think they're the bad people who took Mom?] [Of course they're bad!] She answered before I could. [They're in prison!] [We should leave!] [Wait.]

I was put into a juvenile prison along with my two other stupid friends. When I first arrived, I was terrified. But I soon realized that being the only boy who liked men in a place full of frustrated prisoners was a power move. I stopped hiding. I started exploring what it felt like to be wanted. I became the prison twink, and I loved every second of it.

He is much worse than he shows others to be. I fear he is going to do what he wants with us, so I stay still as a rock, hoping my life will not be put through slow torture that leads up to my death. When Aisha moves closer to me and I see men walking around this room, I realize they are men I have never met, but they are giving me the looks of those inmates that are catcalling anyone who walks into the prison cells. “Who is going first, guys?” A heavyset, bold man who is missing his lower teeth, and in dirty construction clothes, walk around our sofa.

“I told you not to mess this up.” The realization hits me hard. She set me up. The document, the job, the room service act—it was all a trap. My stomach twists with rage as she steps closer, crouching down so only I can hear her next words. “Consider this your final lesson,” she whispers “Never trust anyone. I hope you enjoy prison”