The Naed Prison

The next morning, I walked back into the bondage chamber in my best suit to find Steph's curvaceous body glistening with sweat from what I assumed was a night of orgasmic pleasure. As I walked in, she briefly looked up but then her head slumped back down in exhaustion. I pretended to take no notice of the slight hint of defiance in her eye as I reached for the water hose.

"Rise and shine, bitch," I announced as I mercilessly sprayed her with the hose.

Despite her best efforts to keep her mouth shut, Steph howled as the icy water met her body and washed away all the fluids from the previous night. Once I had decided that she was clean enough, I stopped and smirked.

"So," Steph groaned, "what's the plan for today?"

"The plan..." I pondered this question as I groped Steph's tits. "The plan is to fuck you, and then to fuck you again, and again, and again, until I get tired of fucking you."

"And then?" asked Steph, sounding bored. I pinched her nipples between my thumb and index finger.

"Then some torture and then back to more fucking."

Steph's restraints clinked as she tried to move.

"What are you waiting for?" she asked.

"For the other girls to finish showering," I told her. This finally elicited a worried glance from Steph. My playful smirk turned into a wide grin. "What? You didn't think I'd continue to do this privately did you? You're one of the prisoners now."

"Not for long."

"Why? Because you send that recording to the committee? Yeah, I know about that. Judge Stevens shut that down."

Steph shrugged. "You still have no proof I did anything."

I cocked my head. "Who knows what the future has in store for either of us, but for now, you're my bitch, so you're going to do what I say or else."

I retrieved a collar from one of the endless supplies of bondage equipment in the room and clasped it around Steph's neck. I attached a metal leash to the collar and then undid Steph's restraints.

"Crawl, bitch!" I barked as I tugged on the leash. Steph wordlessly obeyed and followed behind me like a... well... like a bitch. We walked to the breakfast hall where the other prisoners had just begun eating. They all stared at Steph despite being informed about her situation that morning in the shower. I got an even bigger hard-on thinking about how Hanna openly masturbated at the thought of Steph being dominated in prison.

"On the table," I commanded with a slap on Steph's ass, loud enough for it to echo throughout the room. I could have sworn I saw her blush as she confidently did what I ordered. I roughly grabbed Steph and manhandled her into a face-down and ass up position. She made no efforts to resist.

"Listen up, sluts!" I shouted. "If every one of you finishes breakfast in the next ten minutes, then you can spend the rest of the time watching Steph take this cucumber up her ass!"

The prisoners cheered as Steph did her best to hide her concern, but I saw her eyes widen when I held up the cucumber for her to see. Yes, the length was impressive, but the width was what she had to worry about. Meanwhile, the other girls wanted nothing more than their former tormenter to suffer, so they began wolfing down their food as quickly as possible.

"Please don't," Steph whispered.

"Don't what?" I asked loudly. A couple of the women chuckled.

"Thought the big bad bitch wasn't scared of anything!" I remarked mockingly with another smack on Steph's ass.

"I'm not!"

"We'll see about that. Meanwhile, you can start by lubing this up.

"With what?"

"You can start with your mouth."

"If looks could kill..." Steph muttered as she spit on the cucumber and began to run her tongue along its edges. I sat back and watched the erotic display with the occasional glance at Steph's ass that would soon be accommodating this huge vegetable.

"Make your tits bounce," I instructed. Steph paused to glare before resuming her task whilst taking care to move her chest in a way that would allow her breasts to bounce. I reached out to grab one of the bouncing boobs before leaning back to observe some more. Meanwhile, all but a couple of the prisoners had finished their meals. I looked over to see Georgina nibbling at her food.

"What's wrong?" I asked her. Georgina looked up at me.

"I don't feel well," she lied.

"Nonsense. You were feeling fine a few minutes ago. You only stopped eating when I gave the challenge, so I'll ask you one final time. What gives?"

"I-I don't want to see any more women here get hurt."

I chuckled darkly. "That's cute, but this is prison, sweetie. Now, you can finish your scrambled eggs in the next two minutes, or you can spend the day in the bondage chamber."

As I expected, Georgina's resolve was not strong enough to withstand such a threat. She gulped down her food until her plate was clean.

"Good girl," I said with a condescending pat on her head. Victoria nearly snarled as I touched her prison girlfriend. "No need to get jealous. I'll be spending time with you in the future."

I walked back to Steph and grudgingly handed her a small bottle of lube. I wanted the cucumber to fuck her asshole, not get stuck inside it. Steph stopped bouncing and snatched the bottle from me. She quickly covered the cucumber in lube before running her hands along it, making certain that every square inch was doused.

"Time's up," I told her. "I'm going to need the lube and the cucumber."

Steph growled and placed both objects into my outstretched hands. I pocketed the remainder of the lube and moved behind Steph to begin the show.

"What's that about?" I asked a guard, gesturing to Brianna and Yvonne's whispering.

"Oh, that?" the guard asked. "They're just placing bets."

"On what?"

"On if Steph can take it without her asshole tearing."

At this, Steph audibly gasped. I thought it best to not waste time with a lengthy speech and quickly clapped my hands.

"Can I have four volunteers to hold her in place?" I asked. Nearly every hand went up.

"Anyone who volunteers will spend a month in the bondage chamber when I'm reinstated," Steph warned. The formerly eager volunteers now shrank back. I scoffed angrily and demanded a whip from one of the guards before bringing it down crashing on Steph's ass.

"That's enough from you," I growled. Steph snickered. I whipped her ass two more times which did nothing to shut her up.

"Fine," I muttered as I approached her from the back. As much as I wanted to shove that cucumber in and hear her squeal, I needed to work my way up. After securing her wrists and ankles in restraints attached to the table, I unzipped my trousers and pulled them off. After applying some of the lube to my cock, I slowly pushed it into the curvy Latina's asshole. Steph gasped as I entered, but not to any uncomfortable degree. She had been fucked in the ass many times before. I grabbed Steph's hips and began to thrust at a faster and faster pace until my dick was sliding in and out without much difficulty. Good. The first step and only step toward preparing her had been completed. I pulled out my cock and handed the cucumber to Anna.

"Care to do the honours?" I asked. Anna smiled.

"With pleasure," she said as she took the cucumber from me and approached the trembling Steph from the back. I stood in front of Steph quite pleased with myself. I had succeeded in breaking her.

"You can stop this," I told her. "All you have to do is say that your my bitch."

"Never," croaked Steph, looking me in the eye despite my still erect cock being closer to her eye level. I shrugged.

"Your choice then," I said, gesturing for Anna to begin. "Spread your ass please?"

Steph glared but reached around and did what I asked before bracing herself. Anna gleefully forced the head of the cucumber into Steph's somewhat looser asshole. Her initial gasp turned into an involuntary yell of pain as the cucumber tore into her bowels. The prisoners watching cheered as Anna slowly but surely began to fuck Steph's ass with this huge vegetable as I merely watched her from the front.

"Open your mouth," I ordered Steph, who barely heard me but did what I asked. I was about to shove my cock in her mouth but then Anna shoved the cucumber once more and Steph had to grit her teeth due to the pain. I settled for just watching the show as I had Danielle come over and suck my dick while I admired Steph's composure to not break quite yet. This was short lived, however. There was a limit to even how much Steph herself could take.

"I'm your bitch," Steph muttered, just loud enough to hear. I had Danielle pause the blowjob and stood up.

"What was that? I didn't hear you?"

"Oh god! I SAID I'M YOUR BITCH NOW FOR THE LOVE OF GOD PLEASE MAKE IT STOP!"

I smirked. I had Steph under my control. I motioned for Anna to stop. She looked disappointed, but removed the cucumber, which came out with a "pop."

"Alright prisoners! Time to go to work! Guards, escort them outside please! I need a bit of alone time with Steph."

I waited for the guards to finish escorting the prisoners out of the dining hall before grinning in front of Steph.

"Told you I could break you," I said smugly. Steph rolled her eyes.

"Can I get into a more comfortable position?" she asked. I thought for a moment.

"You can reposition yourself on your knees in front of my cock if you'd like.

Otherwise, you can stay like that."

Steph hastily got on her knees. She glanced at my cock, still glistening from Danielle's spit, before looking up at me.

"Now, what are we going to do about your whole situation?" I pondered outloud. "I'd love to allow you to be a guard again, but you let a prisoner escape, Steph. That's inexcusable."

"Please! I'll get her back, I swear it. I was a bounty hunter for a while. A snooty model bitch like her won't know where to hide. I'll track her down in twenty-four hours tops!"

"Are you admitting to releasing her?"

"Not necessarily."

"What if I shoved the cucumber back up your ass?"

"Then it won't be admissible."

"Perhaps not, but it would be fun."

"Please! Look, we're grown adults. We can come to some sort of understanding."

"Here's my offer," I said, "and it's final so you can take it or take your chances with whatever the tribunal decides. You live here as a prisoner for a month, after which you can be reinstated to deputy warden. How does that sound?"

Steph mulled the idea over for a minute before responding.

"I'll be a prisoner for a week and then reinstated to full warden," she countered. I laughed and literally spat in her face.

"You're in no position to make demands," I told her. Steph stood up, against my standing orders, which made me slightly nervous. Whatever, I could still take her.

"If you held all the cards, then I would be choosing between serving three years here or twenty-five to life in a regular prison," explained Steph. "Don't try to play me, John. I've been here a long time now; I know how this place works. You know you won't be able to keep me a prisoner long so you're trying to weasel something out of it before you have to release me."

"You don't know that."

"For certain? No. Which is what you're counting on and I'm not falling for it, so that's my final offer. One week as a prisoner, then co-warden, and I don't confess to shit."

I thought about haggling some more but then I remembered that there was no guarantee that they wouldn't make Steph full warden again and leave me as a guard. No, it was better that I had something in writing from her. I extended my hand.

"Deal," I said. Steph hook my hand, after which I pushed her onto her knees. "Now, finish sucking my cock, prisoner."

I watched Steph rub her pussy as I said the word prisoner and smirked before forcing my cock down her throat. As I became entranced by the traditional "glug, glug, glug" of a good blowjob, I grew harder at the thought of essentially owning Steph until I finally came in her mouth. She let me see the cum before I allowed her to swallow it. As Steph got up and walked off toward the rock pile, I put my cock away and pondered the future. Who knew how she was going to react once she was back in a position of authority, but at the very least, this was going to be a fun week.