From Bad Boy To Good Girl

by Ms. Dee Praved

13 Aug 2021 8074 readers Score 8.4 (52 votes) PDF Mobi ePub Txt


I was relieved when the guards pulled me out of processing. They told me I had a special housing assignment away from General Population. At nineteen, and one hundred and forty pounds I knew I was no match for the monsters on the yard. 

The two guards that pulled me from intake didn't talk as the walked me to another building. It was much smaller and away from the main part of the prison. I assumed it was a house for young offenders to be kept safe from older predatory ones.

I quickly found out I was completely wrong. 

I'm now standing in the middle of a concrete room, naked, with my wrists cuffed to a hook above my head. A large burly guard appears and walks around me, appraising me. He squeezed my butt, and strokes my cheek. "My, my, my, what do we have here?" He chuckles. "Oh we are going to have some fun with you!" I start trembling as I begin to have an idea about what is going to happen. 

"Welcome to the Cathouse! I'm Mr. Johnson. You will call me sir. You will call every man sir." The burly guard says with a smile. "Wonder why we call it that? Well I'll explain. We take bad boys and turn you into good obedient girls!" 

I start to voice my objection and I'm quickly slapped across the face. "Shut up bitch." The burly guard scolds. "You should be thanking us. You were going to be a bitch anyway. Here, you will be our bitch. We don't let the animals get the young, sweet ones. We keep them for ourselves." I heard a few chuckles behind me. "You will quickly learn your place." He nodded to someone behind me. 

I felt a sharp sting across my butt followed by several more. I was being whipped. Johnson watched approvingly, then nodded and the whipping stopped. "That was a sample. Resist or misbehave and it gets much worse. If you get to resistant we will just dress you up nice and walk you to the mainline. Where you will be real popular. You understand me?" 

I nodded and received another slap. "You say yes sir!" Johnson screamed in my face. 

"Yes sir." I blurted out. 

Johnson fixed a collar around my neck with a chain attached. "You will keep this on at all times. And your new name is 24." I was uncuffed and led off. 

They led me to a cell. Inside was what looked like a beautiful woman dressed in lingerie, except a small penis was visible in a pair of pink panties. "Make it presentable." One of the guards instructed.

"I'm Number 6" the gurl introduced herself. She helped me shave off what little body hair I had, gave me a few makeup pointers and then helped me dress. I began crying as I slid black stockings up my legs. 

"Awww it's not so bad." She consoled. "We are actually treated pretty good as long as we behave. It's better than we would get in General Population for sure." 

It didn't really help me feel any better. Especially after I looked in the mirror. Earlier in the day I had been a male, and now here I was. Black stockings, black thong panties and a lacy corset. My lips were red and I was wearing blue eye shadow. Holy shit. Was this really happening? It most definitely was. 

I heard a low whistle behind me. "Damn! Oh yeah. 6 you always do nice work!" He led me to a break room where several guards made catcalls as he paraded me around. "Lucky fuck" I heard one say as we walked by. He then took me to a vacant cell. 

"My lucky day. I won you. I get you first!" He said as he undressed. "Won me?" I asked? 

"Sure!" He explained. "We draw names for who gets to pop a new bitches cherry. I won you. But don't worry I'll be gentle!" 

It hit me that I was about to get fucked. He was now naked and his long dick was erect. He liked his lips and eyed me like a piece of meat. He took my leash and sat on the bed. He jerked me towards him. 

"Get down there and suck my cock bitch." He ordered. 

For the first time in my life I touched another guys dick. It was big. I stared at it. Unsure of what to do. He quickly slapped me. "I said suck it." He demanded. I knew I had to, there was no escape, no point in resisting.  With that I put it in my mouth. I had only received a few blowjobs myself, and here I was giving one. "Oooohhh yeah." He moaned. He held my head down making me choke. I didn't so much suck as he fucked my mouth. He laughed everytime I gagged on it, and just thrust it deeper. It was brutal. But then I began thinking about how bad getting fucked with it would hurt. 

"Suck my balls bitch!" He ordered. He really liked that.

I sucked a bit more before he was ready to fuck me. He pushed me belly down on the bed, and got on top of me. I felt lube on my ass and the wet head of his dick against my whole. "Mmmmm virgin pussy." I heard him say. I couldn't believe this was happening to me. I felt him shove his cock against me trying to force it in. 

"You may as well relax baby. You're getting fucked. If you relax it will be better. You may even like it." He taunted. I grit my teeth as he penetrated me. Fuck it hurt. "Oh yeah. Take that cock." He whispered. And with that he was fucking me. He slammed violently into me over and over again. His hairy body pinning me down, he savagely fucked me. I felt myself crying as he took away my masculinity. Here I was, wearing stockings and panties getting fucked. His pelvis made a slapping sound against my but as he furiously humped me. I struggled underneath him knowing I couldn't get away. He slapped my face a few times and spat on it to further degrade me. 

"You like that dick don't you. Tell me you like that dick." He was ordering. He slapped me and demanded I tell him I liked his dick. "I like your dick I blurted out, and he laughed. He was now really banging me hard and fast and soon I heard him moan loudly. He was coming in me.

He pulled out and stuck his wet dick in my face. He ordered me to suck it. I tasted the cock that had been up my ass and the last of his sperm. He looked down at me smiling at his conquest, feeling cocky knowing he had just taken my dignity and manhood away. 

"Did you enjoy that as much as I did?" He asked as he put his uniform back on. He smiled. "Probably not. But you will. You're gonna be one of my favorite bitches." He kissed me before leaving and locking the cell door.

I just laid there, feeling his sticky cum on my destroyed asshole. I felt the stockings on my legs, the tight corset and the panties. I was now a sissy bitch, who had just been fucked by a man. Just like a girl.