The Naked Prison Ch. 10

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The warden continues attempting to break Steph.
3.9k words
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Part 10 of the 10 part series

Updated 06/29/2023
Created 07/18/2021
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"You missed a bit on the tip."

Steph silently crawled back and delicately licked the final drop of cum off the tip of my semi-erect cock. It was almost evening and I was coming to the end of the best day of my life. After Steph's surrender earlier that day, I watched her for hours on the rock pile before taking her back to my room. I did it all. I facefucked her and then used the spit from her blowjob and the lube from the cucumber to spend the next hour fucking her in the ass. I yanked her hair and with each thrust, I smacked her ass checks again and again until they were bright red. Every so often I'd spank a cheek for good measure while reminding Steph whose bitch she was. Literally. I made her say it too which she was very willing to do after a few smacks on her already sore ass.

I believe it was this hour that broke Steph. She spent the first third of it gritting her teeth and moaning, the second third crying and begging, and the final third silent. When I was done I was nearly afraid she passed out but I saw signs of life. Nonetheless, Steph continued to give me the silent treatement no matter what I did to her. She obeyed me. That wasn't an issue. Steph performed the most humiliating and degrading tasks without question. She kissed my ass and even gave me a full tongue bath without complaint, but also without a word, even after the throatfucking and facial.

"You're to leave that cum on your face until I give you permission to clean it off," I ordered. Steph looked up at me from her knees but said nothing.

"Tell me how good my cum tastes," I demanded. Steph still said nothing. I walked up and slapped her across the face. She still said nothing.

"SPEAK!" I shouted. I was beginning to get annoyed. Steph continued to be silent.

"Alright," I told her. "If that's how you want to play this, then we can do that. Come with me."

I handcuffed Steph's hands behind her back before grabbing her arm and leading her to the main room where the prisoners were gathered for tv night. Several whooped and cheered as they saw the cum slowly drying on Steph's face. Steph had obviously fucked other men before, but she was always in some measure of control. This was the first time in her life where her erotic humiliation was real and it was getting to her. She actually blushed!

"I know you were supposed to watch a movie," I said, once the prisoners settled down, "but there's a slight change of plans. Instead, we're going to watch a porno starring your former warden!"

I shot Steph a smirk as I played the video on the giant screen. It was Steph taking the cucumber up her ass that morning. Every moment of Steph's discomfort was displayed on her face as she watched the video in silence. I played with her tits as the video went on and eventually changed to me fucking Steph in the ass. I had recorded a little bit of her earlier subjugation and the prisoners were loving it. Hanna played with her pussy as Danielle tried to look away but couldn't.

"Damn, bitch!" shouted Brianna. "You can take it well, you sure you ain't a sub?!"

The prisoners roared with laughter as Steph turned bright red. I continued to grope the busty latina while pressing my crotch against her bare ass.

"Grind," I whispered to Steph before removing her cuffs and sitting down. Steph began to give me a lap dance in front of the prisoners and the guards, who tried to ignore it but also could not. I shamelessly grabbed her tits and ran my hands along her body. Steph still said nothing, even after I continued the humiliation for a half hour.

"You can stop," I told her. Steph got off my lap and I hastily ordered another guard to take her to the shower to clean up.

"You can watch your movie now!" I announced. A guard changed the film as I first stopped by the bondage chamber for some equipment before going to the showers.

"She has nice tits," I remarked to the guard.

"I-I guess," the guard murmured back. She definitely seemed uncomfortable. It wasn't because of Steph's nudity, but rather her place as the former warden.

"You can go," I said. The guard was only too eager to leave. I watched Steph rinse off her body with mild amusement. "I'm hard now."

Steph said nothing. I roughly grabbed her and bent her over a nearby sink before unzipping my trousers and lining my cock up to her pussy. Steph instinctively spread her legs. I removed my cock and put it away.

"Wha-" Steph began before silencing herself. I showed Steph what I got from the bondage chamber and she looked puzzled.

"It's a chastity belt," I informed her. Steph's eyes widened slightly but she quickly became master of her emotions once more. "Spread your legs, prisoner."

Steph looked me straight in the eye as she spread her legs ever so slightly, but it was enough for me to get the steel belt on and the bit between her legs. I clicked it shut and then turned the key.

"If you won't fully submit to me, then I won't let you cum," I told Steph. She shrugged.

"Ok then," I remarked as I led her back to her cell, "but I know you. You'll be begging for an orgasm by Friday maximum."

Steph remained silent as I escorted her to an empty cell and slammed the door shut before locking it. I had to admit that I felt quite pleased with myself. Steph was obviously used to all sorts of degradation and even got some pleasure out of it, but this was the one thing she couldn't resist. I considered grabbing one of the other girls to suck me off or something, but I was too drained from fucking Steph all day. I returned to my quarters and slept like a baby.

The next morning I woke up to my alarm and groaned as I turned it off. I looked around for the prisoner that was supposed to be taking care of me that morning until I realised that Steph was the one who arranged that. I didn't bother getting dressed as I made my way to the showers where the prisoners, including Steph, were bathing. Unlike the other women, Steph was still wearing her chastity belt and as much as she attempted to hide it she was clearly uncomfortable. I caught her hand dropping down to her pussy more than once before she remembered.

"Hey, Hanna," I greeted as she was washing her B cup tits. She smiled back at me.

"Blowjob?" she asked. I shook my head.

"Not right now. No, I have an assignment for you. It could take a few months off your sentence."

At this, Hanna perked up. Although she was certainly enjoying herself at times, the offer must have been tempting. She only had a few months remaining on her sentence.

"What do I have to do?" she asked. I gestured over to Steph.

"Make sure she's constantly horny," I ordered her. Hanna simply nodded and moved to occupy the empty shower next to Steph.

"Bathe me," I told Victoria, who had been silently bathing next to Hanna. Victoria gave the slightest of sighs before rinsing herself off and attending to me.

"Why me?" she asked as she began to soap up my chest. "There are plenty of straight or bi girls in here."

"Because it's hot," I told her. Victoria rolled her eyes and did her best to hide her revulsion as she washed me. I particularly relished in her careful attention to my cock and balls. Of course, she waited until the end but I didn't care.

"You missed a spot," I informed Victoria, turning around. She groaned and began washing my ass.

"Why don't you get on your knees and kiss it," I told her. She grumbled and placed a delicate kiss on my ass cheek.

"Nah, fuck that. Steph, show her how its done!"

Steph obediently got on her knees and stuck her tongue in my asshole. She swirled it around twice before stopping.

"Good bitch," I said. "Now you try, Vikki."

Victoria nearly gagged as she imitated Steph and cleaned my asshole with her tongue. I snapped my finger and indicated for Steph to suck my dick, which she did without question, but again without a word. I made a show of my orgasm as I came in Steph's mouth.

"Ohhhhh yeah!" I moaned. "God, that felt so fucking good!"

For a moment, I thought I saw a flash of annoyance pass over Steph's face. I knew she wanted to cum, but I wasn't going to go as easy on her as she did on me. I smiled and had Victoria stop lapping at my ass.

"Shower time's over girls!" I announced. "Hope y'all enjoy the rock pile today!"

"All except Stephanie," said a familiar voice. I looked behind me to see Judge Stevens standing there in a three-piece suit. I instinctively covered myself to which he just chuckled.

"As much as I'd love to stay here and watch you girls shower, I need to meet with John and Stephanie alone."

The guards quickly escorted all the prisoners out except Steph, who still had cum dripping from her chin. I scooped it up with a finger and stuck it in her mouth.

"The board wants you to test a new form of work for the inmates," Stevens informed us. "and who better to test it than our lovely Stephanie here!"

Steph had no reaction, even as Stevens groped her wet tits. She did, however, release the slightest of frustrated sighs as his hand made its way down to her crotch. Stevens whistled.

"Chastity," he remarked, "not a bad idea."

"What's the job?" Steph asked, breaking her silence. Stevens responded by smacking her in the face. Steph was dumbfounded at his nerve for a moment, but brushed it off quickly.

"The men were talking, whore!" retorted Stevens. Steph scowled but remained quiet.

"I can gag her," I offered.

"No need," replied Stevens, unzipping his trousers. He gently (but firmly) pushed Steph onto her knees and she instinctively took his cock in her mouth.

"As I was about to say, the board is concerned that breaking rocks isn't.... productive enough."

"But they also-"

"I'm afraid this isn't up for debate. The board already voted. They want you to trial a new system. Shall I demonstrate? We've already set it up on the beach."

Sure," I said. "Do you want to finish or...?"

"There's time for that later," Stevens replied as he reluctantly made Steph stand up and put his cock away. Once she stood up, I cuffed Steph's hands behind her back. I knew she wasn't going to run, but it made the spectacle even more erotic. Steph would have never admitted it, but she was becoming the perfect prisoner. All it took was a smack on the ass for her to start walking. I marched her outside until we arrived at what looked like a large wheel. As we got closer, I could see that this was, indeed, a wheel.

"Allow me to demonstrate?" asked Stevens. I nodded and he took Steph's arm and uncuffed her. I could now see that there were chains attached to the wheel. Stevens locked Steph's wrists and ankles to the metal cuffs but not in a way that restricted her movement. I shot a quizzical glance at Stevens.

"This prison costs a lot to maintain," explained Stevens. This wheel is perhaps not the latest in technology. It requires labour to make it work. That's where the prisoners come in."

"I'm not sure I understand."

"Stephanie, why don't you start running please?"

Steph began to run and her large tits began flopping around. I was mesmerised. Stevens laughed and redirected my attention to the gears on the wheel.

"Is that... electricity?" I asked.

"Precisely! Why waste energy powering this place when the prisoners can do it for us?"

"That's brilliant!"

"The board thought so."

"But won't they get tired after a while?"

"That's what this is for," remarked Stevens, pulling out a whip and bringing the lash down on Steph's back. She began to run faster.

"Good girl," he cooed, giving Steph a slap on the ass. "There will be twenty of these arriving by the weekend. Make sure the prisoners are in decent enough shape by then. They'll also need to work in shifts now as even with the whip they won't be able to keep it up forever."

"Alright."

"Also, there's one more thing."

"What is it?"

"My wife is leaving town for a couple of weeks and I'd like Danielle to be remanded into my custody for that time. You know, like we agreed."

"Of course! She's a hottie."

"That she is, that she is. If it's alright with you, I'll have my men take her to my chopper now."

"Of course! She can finish what Steph started. By the way, any luck tracking down Nicole?"

"Unfortunately not. She seems to have gone off the grid."

"Too bad. Well, have fun with Danielle!"

"Believe me, I will, and you have fun with Stephanie!"

With that, Stevens left me alone with the busty Latina, who was beginning to sweat under the morning sun. I quickly got an idea and radioed for a guard to bring me nipple clamps. I had Steph pause for a moment and attached the clamps before ordering her to resume running. This added yet another layer of discomfort for Steph.

"Do I have to shove that cucumber up your ass again to get you to talk?" I asked Steph as I watched her sweaty tits sway with each step.

"Fuck... you," muttered Steph. I laughed as I cracked the whip. Steph flinched even though it didn't touch her. I could tell that I was slowly breaking her. My goal was to have her eating out of my hand by the end of the day, both metaphorically and literally.

"Say your my bitch," I demanded. "You had no trouble saying it yesterday."

"I'm your bitch," Steph muttered again. I raised the whip and brought it down on her tits. Steph was the master of calm and composed during these bdsm sessions, but with the nipple clamps this proved to be too much. Steph let out a high-pitched and girlish scream.

"Oh my god, you made your point already now let me down!" she cried.

"Nah, not yet."

"For fuck's sake, what do you want from me?! I'm already doing everything you're asking. I'm a fucking model prisoner."

"I want you to admit what you are."

"And what's that."

"My bitch."

Steph sighed. "If I say it will you let me stop?"

"If it's convincing."

"Fine. I'm your bitch. I'm your slutty prison bitch. Happy?"

"Almost. You said it real convincingly when you had that cucumber in your ass. I can get it again?"

"NO!"

"Then say it like you mean it!"

"Can I stop running? It's hard to concentrate when I'm running like this."

I figured that was a fair request so I put the whip down. Steph slowed down to a stop and took a few moments to catch her breath.

"I'm your bitch," repeated Steph in a softer, sexier tone. "I'm your slutty prison bitch who would really love to cum now."

I chuckled as I slid my hand down to Steph's chastity belt.

"Maybe if you're a good girl," I told her. I smirked. I figured her out. I was willing to bet she was more comfortable being whipped than being forced into chastity.

"What do you want?" Steph asked.

"A good start," I told her affectionately. "I want you to come back to my office for now."

I cuffed Steph again and led her inside, just as the other prisoners were getting ready to work on the rock pile. I counted all except for Danielle who was being led to Stevens's helicopter in shackles with her head down and the good judge groping her everywhere as they walked. He took off his pants upon getting into the helicopter and the Italian beauty was seated on her knees in front of him. The last I saw of them was the chopper taking off and Danielle's ruby lips wrapped around the base of Stevens's cock.

"Danielle's going to hate that," Steph remarked as we got to my office. I reached around and twisted her nipple.

"Who gave you permission to speak?" I asked as Steph moaned. more from pleasure than pain. "For the next six days you're still my bitch."

"You spent all day pissed that I didn't talk and now that I am you're mad?"

"No. I'm annoyed that you haven't internalised your new role yet."

"My role for the next week."

"For a bit longer than that," I said, gesturing to the computer where a new email from the board surfaced. As Steph read the email, her eyes widened.

Mr. Williams,

First, we would like to offer you our sincerest apologies for your demotion. We met with Judge Stevens and he informed us of what happened. Stephanie Gomez's role in all of this is unclear, but we do not believe she was acting maliciously, as Stevens contends. However, she is responsible for the release of not only one, but two prisoners. Prisoner #4343876, previously known as Warden Connelly, never made it to the facility where we intended for her to serve out her sentence. We are therefore forced to conclude that it is a result of Ms. Gomez's negligence during her brief tenure as warden. Until we can conduct a proper investigation into all this, she will remain a prisoner under the charge of criminal negligence. You may house her with the other inmates or separately, depending on what you see fit.

In short, we have full confidence in your ability to do the job going forward and should Ms. Gomez be acquitted of all criminal charges, she will be reassigned to a lower security prison while we assess her ability to do her job. Thank you for your patience and good luck implementing the new work program for the prisoners.

Best wishes,

James Garland

Jonathan Evans

Carlos Campos

Steph gasped.

"No fucking way!" she cried. I couldn't even bring myself to make some witty remark. As much as Steph was annoyed by her current predicament, I knew that she loved her job. It would kill her to be reassigned to a normal prison.

"I-I can't be fired. After everything I've done for this place!"

"Relax," I interjected. Steph shot me a harsh look.

"And you! Everything was fine until you entered the picture! And to think that I actually had feelings for you at once point!"

I snapped my head up at that. "What?"

"Oh, don't act so surprised," Steph hissed. "As much as I love dominating women, I need a man in my life and in case you haven't noticed, you're kinda the only man around here."

"What I'm hearing is that you need a man to dick you down every so often."

Yes. What, does it make you hard hearing that? I can see that it does!"

"Of course it does, Steph!" I said, standing up. "In case YOU haven't noticed, you're fucking hot, and I'm going to do everything in my power to keep you here."

"As a prisoner though."

"Would you rather be a prisoner here or be reassigned somewhere else?"

Steph bit her lip and thought hard. I began to unconsciously stroke my cock in front of her as I would another prisoner.

"I guess it doesn't matter now if I tell you that I like you dominating me," Steph confessed after a long pause. "At first, you seemed inexperienced, but now that you're getting into your groove I can see you've got great potential. We could have made a great team, but-"

"We can still make a great team," I said. "Here's my proposition. I'm going to keep you a prisoner and I'm going to suggest that to the board, but you won't be on the same level as the other prisoners. I think I can make that call since you haven't been convicted of anything. However, you'll still obey my every command and while you will be in charge of the other prisoners-"

"I'll still be one myself," said Steph quietly, finishing my sentence. "I'll agree if you agree to rehire me once my sentence is up."

"Is that my decision?"

"Um, duh! You're the warden."

"Ok, then we have a deal, but I wanna hear your submission."

"Sure, but I also want out of this belt."

"I think I want to keep it on you for a few days."

Steph grumbled. "Ey, ey, ey," I said, slapping Steph's face with my very erect cock. "I'm basically your master now. What I say goes."

A look flashed across Steph's face and I could tell she was incredibly turned on. She clearly had a submissive streak.

"Yes... master," Steph uttered at last.

"Try again."

"Yes, master!"

"Good girl. Now, who's your daddy?"

"You're my daddy, master."

"Who's bitch are you?"

"I'm your bitch, daddy! I'm your horny, slutty, prison bitch who is ready to obey your every command!"

I smirked. I had broken the brat. I poked her lips with my cock.

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