The Naked Prison Ch. 02

Steph spent the rest of the afternoon explaining how things worked in the prison. Over time, it became clear that she was much better suited to be warder than I was. I even pointed this out and she simply explained that they wanted a male warden. Besides, Steph would be happy as long as I let her have free reign over the prisoners, something I was happy to allow. At four, we went to the auditorium where the prisoners were already being seated in front of a stage by the other guards. I finally saw all of them at once. There was a great diversity with the youngest being Yvonne, but most in their 20s and the oldest being the former warden, now sitting in solitary. I'd have to make a decision on her soon, but not yet. I buttoned my suit jacket to hide my latest erection and walked up to the podium.

"Hello everyone, I am John Williams, the new warden. I'll keep it short, things are going to run just like they did before and that means it's time to spin thee sex wheel. Steph, who's up?"

"It's Anna's turn!" called Steph.

"Anna, please come up to the stage."

Anna stood up showing off her slim body, covered in tattoos. It was hard to believe someone so petite could be a mob assassin, but she was. Her sentence was the maximum three years, but this was after spending five years in a real prison. This wasn't ideal for her, but better than life with no parole, especially at the age of 27 when she was convicted. At 33, she looked just as beautiful. The Japanese assassin walked up and stood in front of me, stoically awaiting her fate.

"Anna, please spin the wheel," I said, gesturing to a large wheel filled with nearly any sexual act you could dream of. Well... at least ones not too deviant. Anna spun the wheel without any signs of nervousness and I noticed her backside made up for what she lacked in bust. The wheel came to a halt on anal sex. A couple women cheered but were quickly silenced by Steph. A couple other guards brought a table and then went back to hanging out on the sides or groping some of the prisoners.

"Bend over the table Anna," I told her. Without any emotion, she did as I asked and braced herself. Steph walked up to me with a bottle of lube she produced from a pocket.

"May I?" she asked. I nodded and Steph unzipped my trousers and pulled out my cock to lube it up. She was more mechanical than anything as she made sure every inch of my dick was covered in lube.

"That bitch killed at least seven people," Steph whispered in my ear. "Make it hurt."

I slowly walked up and placed my hands on Anna's hips. She made no indication of knowing that I was even there. I smacked her ass hard. Still nothing.

"Spread your own ass, whore," I told her. Anna methodically reached back and spread her ass cheeks with her hands.

"Keep those cheeks spread or else you'll be up for the wheel of pain next," I told her as I inserted my lubed cock into her asshole. As I started to fuck her she helped, holding her ass open, but I wanted her to fail. I spanked her ass again. Nothing. I then lifted a leg onto the table and began truly hate-fucking her. At last, she had some reaction and let out slight whimpers of pain as I tore into her, not caring how much it hurt. The bitch deserved it. SMACK! That one hit at the right angle and the cheek slipped.

"Wheel of pain it is," I said as I continued pounding into her. Anna bit her lip to stop from crying out despite the lube. "You used to be somebody, but now you're... just... my... fucking.... SLUT!"

I slapped her ass one last time as I came inside her asshole. I dismounted her and pulled her upright.

"You're not finished yet bitch," I told her as I led her back to the wheel, but this time it had been replaced with only torture options. "Spin it."

Anna regained some of her stoicism as she spun the wheel without so much as a peep. After what seemed like an eternity, it landed on flogging.

"Prepare her for a whipping," ordered Steph. A guard grabbed Anna's wrists and cuffed them to a beam above her head. Stphanie brought me a black duffel bag. I looked inside and saw it was full of various crops, whips, paddles, and other bondage equipment. I selected a flogger that didn't look too painful.

"Nah," whispered Steph. "Pick the bullwhip."

I rummaged further and found a black bullwhip. It looked painful but I suppose that was the point. I was a bit nervous as I had never whipped a woman before. My ex barely wanted to be spanked. I walked up to Anna and showed her the whip.

"I'm curious," I asked the tattooed Japanese woman in front of me. "Do you feel any remorse for your crimes?"

Anna looked me in the eye. "What's done is done," she said. I took a step back and brought the whip down on the floor with a loud CRACK. Anna's eyes widened and for the briefest of moments, I could see genuine fear.

"Front or back?" I asked Steph.

"Back," blurted out Anna. I glared at her and brought the whip down on her stomach causing an involuntary yelp. I then whipped her across her small but still present A cup tits.

"Did I fucking ask you, bitch?" I growled, whipping her pussy next. Anna went back to biting her lip but two more lashes on the pussy broke her resolve and with each lash of the whip on her tits, stomach, and pussy she screamed out in pain. The audience was amused. I had guessed Anna wasn't very popular.

"How many was that?" I asked Steph.

"Twelve," she replied. I stood directly in front of Anna who was taking deep and shaky breaths.

"I thought it would take longer," I told her. "I'm honestly disappointed."

"Go fuck yourself," Anna hissed. I moved behind her and slapped her ass.

"Why would I do that when I have you?" I asked as I surveyed the large tiger tattoo on her back.

"May I have a turn?" asked Steph in a sweet high pitched voice. Somehow, I knew shit was about to get serious. I handed her the whip.

"She's all yours," I told her. I got off stage and looked around at the prisoners. I didn't want Yvonne again so soon. I couldn't have her think she was a favourite. My eyes fell on a busty Italian girl with long sleek black hair. She was way too gorgeous for prison. I remembered from her file that she tried to poison her husband for sleeping with another woman.

"Danielle, is it?" I asked, reaching out to squeeze her tits. She looked up and nodded.

"That's me, sir," she affirmed. I kneaded her tits for a few moments before snapping my fingers.

"On your knees," I ordered her. She complied almost immediately. I sat down in her chair. "Get my dick out and start sucking."

Danielle unbuckled my trousers and pulled out my cock and balls. She wasted no time getting to work despite undoubtedly still tasting Anna's ass on my dick. Sitting to the left of me was Yvonne and to the right was a white girl with an average enough body but a cute face. I reached out and grabbed Yvonne's right tit and this other girl's left tit as Danielle blew me and I watched Steph whip Anna, who was taking the back whipping much better. However, Steph was cruel and sometimes snuck in a lash on Anna's pussy which always got a reaction.

"Hanna, right?" I asked the girl sitting to my right.

"Yes, sir!" she replied, not taking her eyes off the action.

"You're bi, right?"

"Yes, I am sir."

"You must be loving this."

Hanna blushed. "It has its moments," she admitted. I gave her a knowing smile and focused on Anna, who was now being whipped from the front again. Steph was a master at hitting all the right spots.

"I'm gonna give you a choice," said Steph after Anna caught her breath. "That was thirty lashes or so between me and Warden Williams. Give or take anyway. I'll let you choose. Thirty more lashes or I leave you cuffed here like this for the night."

Anna thought for a moment. "The lashes," she replied. There was some surprise among the crowd but I knew that's what she'd pick. She screamed, yes, but she wasn't broken. Meanwhile, if she was left cuffed to that beam all night she'd be at the mercy of anyone, guards or prisoners.

Meanwhile, Danielle was doing an expert job on my dick, using her tongue, deepthroating on occasion, and not forgetting to say attention to my balls. I was close to cumming, but I didn't want to before the whipping was done.

"Stop for a sec," I told Danielle. She removed her mouth from my crotch and I started slowly jacking off.

"Lick my balls," I told her. Danielle immediately buried her face deeper in my crotch adding to the degradation of this quite stunningly beautiful woman. Steph began whipping Anna's back a few times before picking up the tempo. Finally, Anna couldn't hold in a single scream.

"AH! OWW! AUGH! AH! NOOOO!!!" she cried as she squirmed from each lash. Steph stopped for a moment.

"You didn't count the lashes," Steph said. Danielle took a ball in her mouth and sucked on it.

"Y-You didn't tell me to!" protested Anna. Steph chuckled.

"Yeah, but you should know to do that by now," said Steph, whipping her ass again. "Haven't you ever seen a porn video?"

"One," called Anna. Steph grinned.

"That's more like it," she said, cracking the whip down on Anna's tits next.

"AH! T-Two!"

"Good girl! Of course, my offer still stands."

Anna groaned. Her body was obviously sore. "Can we make a deal?" she asked.

"I don't know," replied Steph. "Warden?!"

"One moment!" I called back before turning my attention to Danielle. "Start sucking again, I need to cum."

Danielle took my cock in her mouth again and I stopped fondling the other girls and instead made her facefuck me. It didn't take long at this point. I forced my cock into Danielle's throat and nutted inside her warm orifice. After removing my dick, I could see that she was choking a little on the cum. Some dribbled onto the floor.

"Breathe, Danielle!" I said, patting her on the back. She caught her breath and flashed me a grateful look.

"Lick up that cum," I told her. Danielle looked slightly disgusted but she lowered herself to the floor and did it anyway. I put my foot on her head to keep it there until the cum was all gone.

"Good slut," I told her as I pulled up my trousers and joined Steph on stage. "Sorry, I was occupied."

"Hey, I get it," she said. "Danielle's a good fuck! So, what do we think about this bitch's request?"

I looked at Anna. She couldn't take 30 more lashes no matter how brave she tried to be.

"Anna," I began, "do you have a proposal?"

"I-I could fuck you," she said.

"But I can just have Steph whip you and then fuck you anyways. Give me a real alternative or I'll give you an extra thirty lashes for cutting my time with Danielle short."

Anna looked defeated at that. Even she knew sixty lashes were too many.

"I'll take the original offer," she said.

"To be cuffed here until tomorrow morning?" I asked.

"Yeah."

"Alright," I told her as I admired the red stripes that were visible underneath her tattoos. "But I have an interesting offer for you. What if I told you that there was a way to not only spend the night in your cell but to earn yourself a possible early release?"

Anna sprung to attention upon hearing about early release.

"Of course, you'll still serve the remaining two years in a normal prison. However, you will only be here for another three months."

"What would I have to do?" asked Anna. I smiled.

"Consent to a new tattoo that says "prison bitch," just above your ass," I said as I traced out where the tattoo would be. Anna thought about it while Steph laughed her ass off.

"Now you're getting the hang of it," Steph said. Anna looked horrified by my prospect, but she was seriously considering it.

"Of course, the next two years in prison would be tough for you," I reasoned.

"Can I make a counteroffer?" asked Anna.

"I'm listening."

"The tattoo will say 'warden's bitch' instead."

As much as that turned me on, I held my ground.

"Sorry," I told her, "but no. It has to be 'prison bitch.'"

Anna glared. "They probably barely approved my transfer and reduced sentence here to begin with. No, you might get to do whatever you want with my body, but I will at least keep the dignity of choosing my own tattoos. And I know you can't force it on me because you can't permanently mark prisoners and this includes tattoos. So checkmate."

"I can still make your life miserable, you stupid bitch!" I said as I slapped her across the face before spitting on her. "Steph is going to whip you thirty more times, then you'll be left here for the night and come tomorrow, you're spending the rest of the week in the bondage chamber. Oh, and it's only Monday now so you have a lot to look forward to."

"Wait-" began Anna. I slapped her in the face again.

"Sorry, I can't go back to the original deal now because that would fall under coercion. Sucks to be you I guess. Oh and Steph? When you finish up here, make sure the air conditioner is turned up at full blast. I might stop by later tonight and I'd like her nipples to be hard for me."

"Will do," said Steph as she prepared to whip Anna, who closed her eyes to brace herself. I walked out of the auditorium and back to my office as I heard the whip and Anna's subsequent screams behind me.