The Naked Prison Ch. 04

I began to settle into my routine over the next few days and at times it was almost as though I were a normal warden. It wasn't all fun and games. There was paperwork to fill out, legal stuff to deal with, and the day-to-day activities to supervise. That last one was a bit more fun as I at least got to look at naked women all day. If I popped a boner, I'd simply choose one of the girls and have my way with her, which I was becoming more comfortable doing. It helped that the women expected it and didn't protest much. Some such as Hanna were actually eager to participate.

And then there was Steph. She was absolutely incredible and a master of her craft. I still have no idea what she did to Anna in the bondage chamber, but when I went in the other day she immediately begged me to go easy and that she would be a good girl. I was lenient and allowed her to leave a day early. Grace was still a tough nut to crack, but we were getting there. Steph agreed with my tactic of humiliation as a tool to break her and while Grace tried to remain proud, I could tell it was working.

The morning was a bit of a drag. Steph had the genius idea to bring a girl into my chambers to bathe me each morning so that I could take full advantage. The shower would usually end in a handjob or a blowjob depending on my mood. Rarely sex as shower sex tended to be complicated. Then I'd spend part of the morning supervising the women during their work in the morning. This week it was the rock pile, which served no purpose other than to give them something to do. I had the ability to choose the work each week, some of which would actually generate revenue. For next week, I was going to have them build computers. They would be happy to not be doing something physically taxing.

Afterward there was lunch and some women would have another quick shower. Steph liked to use that opportunity to fuck them. After that was supposed to be free reign, but most of the guards (being women) didn't take advantage. I did, mostly because in the afternoon the prisoners were supposed to have time off and I'd have to do boring paperwork. One time Steph felt bad and blew me in my office. She and I sometimes hooked up, but for her, it was strictly casual and to satisfy the other half of her bisexual urges. I was starting to develop feelings for her, but I knew she wasn't that type of girl.

My favourite part of the day was the sex wheel. That hour when all the guards and prisoners went to the auditorium and watched some act on stage. Monday had been Anna's turn, which got her sent to the bondage chamber. Tuesday was Yvonne's turn. That one was boring, all she had to do was play with her tits so the session was over quickly. Wednesday was a girl named Nicole, a blonde in her late twenties with super long hair, big lips, and perfectly tanned skin. She had been a model before being caught drug trafficking. She had to eat out a girl, and Steph volunteered herself. I again got a blowjob from Danielle during this, would have a turn herself on Thursday. She had to lick my balls, which I was very pleased about. I lasted quite a while too before finally cumming all over Danielle's face, much to her relief as she was starting to get tired.

Finally, it was Friday. I woke up and Anna was the one to bathe me, fresh from the bondage chamber. She had red marks on both sides of her body, presumably at the hands of Steph the past few days. All she had told me was that Anna had been miserable and that she didn't break any rules. Anna dutifully washed my hair, chest, cock, balls, legs, and ass. I made her manually clean my feet too for good measure. I knew I probably shouldn't be pissing off a professional assassin too much, but I was too used to it by now. After the shower, I spit on her face and told her to suck my dick.

"You're my fucking bitch," I told her as she took me deep. "I'm your master now."

I let her work and turned off the water after cumming in her mouth. I selected a suit which Anna dressed me in, and then went off to join the prisoners for breakfast. I had my own breakfast in my office when Steph barged in.

"Good first week?" she asked. I smiled.

"Amazing first week," I corrected. She grinned and sat down to eat.

"I wanna break Grace today," Steph said. I raised an eyebrow.

"You sure you don't want to play the long game?" I asked. "Eventually she's got to get bored."

Steph leaned forward, giving me a great view down her shirt. Fuck! Now I was going to have to fuck someone after breakfast.

"Your humiliation strategy hasn't been bad," Steph remarked, "but it's all been away from prying eyes. That's the problem. Sure it's humiliating as fuck to try and eat from the floor with her hands cuffed behind her back, but nobody except for you sees it, and I'm sorry, but why the fancy dinners exactly?"

"Huh? I just gave her what everyone else got."

Steph took a bite of her food. "Yeah, but everyone else has been good, hence they get to have sushi. You should just give her broccoli or something."

I pondered that for a minute. "I could eat broccoli for a week."

"Yeah right."

"No, I'm serious. I love broccoli."

Steph looked at me in disbelief. "You must be an alien then."

We chuckled and finished up our meal. "I'll think about it," I assured her before going to supervise the rock pile. The entire concept was stupid to me. They mostly chit-chatted and barely did any work, and none of the guards bothered to make them because it was just a waste of time. I grabbed Yvonne and had her give me a lap dance in my office. She was my Steph substitute.

"Yvonne," I said as she bounced her naked ass on my lap, "can I ask your honest opinion on something?"

"Of course," she answered smoothly. I grabbed her hips as she swayed them.

"What are your thoughts on Warden Connelly?" I asked as I moved my hands up to Yvonne's DD tits. Damn, most of these women have amazing tits. Whoever sentenced them here deserved a medal.

"She was alright," answered Yvonne as she turned around. I grabbed her tits again.

"Would you say the other prisoners share that opinion?" I asked as Yvonne bent down. I unbuckled my pants and slid them off. It was almost time.

"Pretty much," she confirmed as she moved forward, brushing my cock with her tits.

"Thanks, I told her as I stood up. "Bend over my desk, would you?"

Yvonne positioned herself over the desk and stuck out her ass a bit, knowing what to expect. I rubbed my cock around her pussy lips, teasing her.

"Beg me to fuck you," I ordered.

"Please sir, fuck me!"

I slapped Yvonne's ass. "Try again, slut!"

"Please, sir! Fuck me hard! I need your cock in my pussy, master!"

Satisfied, I entered her, slowly at first and then picking up the pace. As I was starting to get really into it, there was a knock on the door.

"Come in!" I shouted without stopping. The door opened and a guard brought in Anna.

"She wanted to talk to you," said the guard. I nodded and pulled out of Yvonne.

"Thanks," I told the guard. "Could you take Yvonne back outside?"

"Certainly," the guard answered, cuffing Yvonne's hands and leading her out the door. I patted my leg.

"If you wanna talk, then you're going to have to finish me off," I said. Anna said nothing but walked up to me and mounted my dick. She began to ride me slowly.

"Warden," she began. "I think you're aware of my background?"

"I am," I affirmed as I sat back and let her work. Anna continued bouncing on my dick and I wrapped a hand around her throat. I was choking an assassin as she fucked me! This made me hornier and I soon came inside her.

"Ahhh," I moaned. Anna was emotionless as usual. She climbed off and sat down in the chair across from me.

"Once I get out of here I can make some calls," she said. "I could make you a rich man."

I cocked my head. "In exchange for what?" I asked.

"Special privileges."

"For instance?"

"Maybe some clothes for starters."

I laughed. "That defeats the whole purpose of this place," I said. Anna looked frustrated.

"How much are you getting paid for this?" asked Anna.

"That's none of your business," I snapped, "and quite frankly the benefits outweigh any salary issues I might have."

"Warden, be reasonable. If I get out and tell my friends about you... they will not be happy."

My heart skipped a beat. This was a concern of mine and now it was becoming a real issue. I had been warned by Steph that some of the bureaucrats in charge thought it was a mistake to ever release Anna, but they agreed to it. Three years.

"Are you threatening me?" I asked, standing up and pulling up my trousers.

"No, I wasn't trying to-"

"Because it sounded like a threat, and threats are taken very seriously here."

"I'm just stating an observation."

I reached under my desk and hit the panic button. Anna glared at me and dropped to her knees before placing her hands behind her head. Within seconds, guards flooded the room and tackled Anna before shackling her hands and feet. It was actually impressive how quickly they did it.

"What's happening?" asked Steph as she burst into the room. I gestured to the chained assassin on the floor. Steph walked ominously toward Anna and stepped on her face.

"Bitch," Steph growled. "I thought you learned after our time together the last three days."

"I did nothing wrong!" protested Anna. "I just asked for some extra things!"

"Take her back to the bondage chamber," I ordered. The guards dragged Anna away screaming leaving me alone with Steph.

"What happened?" she asked, lightly touching my arm. This weirdly helped calm me.

"She told me if I didn't give her clothes and stuff she'd tell her mob friends to kill me," I paraphrased.

"She said that?!"

"She implied it."

Steph paced around the office. "Shit," she said. "We can't let her leave."

"She's going to in three years."

"Not if we get her sent back to normal prison."

"Can that happen?"

"If she poses a danger to society, but you have to prove it."

I shook my head. "What if I just give her what she wants?"

"Don't you dare," warned Steph. "Two things are going to happen by the end of today. We are going to break Connelly, and we're going to make one hundred percent sure Anna doesn't talk."

"How can you be so sure?"

Steph smirked. "Wanna bet?"

"You're on," I said, shaking her hand. "What are the terms?"

"If you win, you get to do whatever you want to me all weekend."

"What makes you think I'd go for that with all these women around?" I asked.

"Come on," retorted Steph. "I see the way you look at me."

"Touche," I remarked. "And if you win?"

Steph smirked. "I get to do whatever I want to you all weekend."

I thought for a minute. "Alright, but I hope you like fucking me cause there's no way you're going to win."

Steph hopped off the table where she was sitting. "Follow me," she said simply. Curious, I followed her to Grace's cell where Steph loudly banged her baton on the bars causing Grace to wake up.

"Rise and shine bitch," she said. "It's almost ten already!"

"Ugh," groaned Grace as she stretched. My eyes dropped to her tits and my cock began to twitch again. What was with me today? Maybe it's because I only came once yesterday. Grace walked to the bars.

"What do you two want?" she asked with an attitude. Steph opened the door and cuffed her hands in front of her.

"We're going for a walk," she said. I grabbed Grace's other arm and helped Steph lead her out to the rock pile where the other prisoners were.

"Good news!" announced Steph. "You bitches don't have to do any more work today, but you do have to stay here!"

The news didn't change much as the prisoners were slacking off anyway. Steph threw Grace into the rock pile

"Get up," she said sternly, producing a whip. She brought the lash down on Grace's ass.

"Ow!" the former warden cried as she now struggled harder to get up despite the cuffs. She was successful after a few seconds while the prisoners watched with awe. Hanna began openly rubbing her pussy.

"Pick up a hammer and get to work," Steph ordered. Grace looked around but not seeing a better option, she did as she was told. The prisoners watched amusedly as Grace worked up a sweat struggling to break rocks. Steph occasionally whipped her as she worked for nearly an hour before Steph allowed her a break.

"Fuck her," Steph told me. "In front of them."

Not wanting to interfere with our bet, I led the sweaty Grace over to the resting tables where I bent her over and fucked her hard. Steph gathered the other prisoners around to watch.

"Fuck..." moaned Grace as I dominated her in front of her former prisoners. Hanna moved closer and Steph motioned for her to move in front.

"Eat her out," said Steph. Grace looked at Hanna's pussy with revulsion, but Hanna was more than happy to thrust her crotch in Grace's face. A lash on her back caused Grace's tongue to fly from her mouth and bury itself in Hanna's pussy. I made eye contact with Hanna who grinned sheepishly as the straight middle aged woman was forced to eat her out.

"You sure you ain't a lesbo?" asked one of the prisoners. Others chuckled at that. I felt a hand on my shoulder as I was almost ready to cum.

"Not yet," whispered Steph. I pulled out and Steph began to slowly jerk me off. Then, Hanna gave one final moan as she had an orgasm on Grace's face.

"Turn around and get on your knees," ordered Steph. Barely thinking, Grace complied and the ever masterful Steph timed my orgasm perfectly as she removed her finger and allowed me to cum on Grace's face. The prisoners clapped in approval.

"Back to work," said Steph, roughing dragging Grace to the rock pile.

"D-Don't I g-get to clean up?" asked Grace. Steph shoved the hammer back into Grace's hands.

"Nope," answered Steph. Grace groaned and complained to which Steph used the whip again to shut her up. Soon it was lunchtime and Steph had actually chained Grace in the middle of the room and encouraged the prisoners to have at it. It was a nightmare for Grace, who spent the half-hour being pelted with food and drinks.

"Come," said Steph. "Let's leave her for a while."

I followed Steph out of the cafeteria and into the bowels of the prison where the bondage chamber was. Steph opened the heavy iron door and there was Anna, chained to a St. Andrew's cross. The air conditioner was on full blast as evidenced by Anna's shivering.

"I gotta hand it to you," remarked Steph. "That AC thing the other day? It works on her. She hates being cold."

"I-I didn't mean what I said," stammered Anna. Steph slapped her hard across the face.

"Yes you did," Steph said, "but it doesn't matter. You made the warden an offer so now I'd like to make you a counter offer."

Anna shivered again and Steph rolled her eyes. She grabbed a hose and sprayed Anna causing her to shriek.

"Oops," said Steph casually, "my bad. That was supposed to be warm water."

Anna's teeth chattered. I would have felt bad for her if she hadn't threatened me earlier.

"Here's the new deal," said Steph. "You're spending the rest of the day here and for the next week, you're going to be the one spinning both the sex wheel and the wheel of pain. You will take your punishment without so much as a peep because you deserve it. Then, you will be on your best behaviour and when you leave this place you will not say anything about this or about the warden here. If you do, then I will have no choice but to tell your mobster friends about how you got the leader put in prison."

Anna's jaw dropped. "M-Mark's been arrested?! B-But how? I never said anything! He knows I'd never talk!"

"I don't know about that," said Steph. "What's he supposed to think when you get out of the slammer with only eight years in total of what should have been a life sentence? You only do that if you're a snitch... or if you end up here, but you really think anybody is going to believe you? In fact, if I were you, I'd probably leave the country after this cause, you know, snitches get stitches."

Anna looked back and forth between us in disbelief. After what seemed like forever, she hung her head in defeat. Steph looked at me triumphantly.

"Let's go check on Grace," she said. We left the bondage chamber, leaving Anna alone in the dark but not before turning off the AC. No reason to risk her getting sick and a subsequent inquiry. We went back to the cafeteria where multiple prisoners were groping, poking, and slapping a very distressed Grace.

"We didn't want to break it up in case it was part of the plan," said a guard. Steph nodded in approval before blowing her whistle.

"Say it," demanded Steph. "Come on Connelly, you know what you have to say."

"I won't," she said quietly. Steph sighed.

"Let me handle this," she told me. "We'll be on stage at four."

I left the cafeteria, a bit worried now that she would win the bet. I was relieved that the Anna threat had been taken care of so easily. Hell, it might be worth letting Steph have her way for the weekend to get rid of that issue, although I had seen firsthand what happens to people Steph is in charge of. I went to my office and tried to focus on paperwork, but the bet was too distracting. Four o'clock finally came and I went to the auditorium where Steph already had Grace cuffed and all cleaned up.

"Hey," I greeted. The prisoners filed in and sat down. They were more attentive than usual.

"Time to spin the wheel," said Steph, removing the cuffs. Grace grimaced, but all Steph had to do was crack the whip for her to spin. The wheel landed on masturbation.

"You know what to do," said Steph. Grace closed her eyes in embarrassment but the other prisoners began to chant so she touched her pussy to try and quiet them.

"Oh no," said Steph. "You have to make yourself cum."

Grace laid down on the floor of the stage and began to get herself off. Her methodical motions soon changed into moans of pleasure as she closed her eyes and pictured herself somewhere far away. Steph's boot on her face a few seconds later brought her back to reality.

"Say you're my bitch," ordered Steph. Grace didn't answer and continued to get herself off with Steph's foot still on her. I added my foot on her tits.

"Oh! Oh! Ohhhh!" moaned Grace.

"SAY YOU'RE MY BITCH!" Steph shouted as Grace began to climax.

"I'm your bitch!" she suddenly shouted. "I'm your bitch! I'm your slutty prison bitch! I'm your bitttttttch!"

Grace's body thrasted with pleasure as an orgasm rippled though her. Steph looked at me with a satisfied grin.

"You win," I sighed. As much as it annoyed me to admit, Steph just solved all my problems.