The Chastity Prison

This story features trans characters, chastity, pegging, submission and straight up, unrealistic concepts. Enjoy.

I knew the risks and I took them, sometimes desperation will push you to do things you'd never do otherwise. Which is why I knew the consequences when my luck finally ran out. I'd been caught stealing, breaking and entering and I'd been caught doing it in the worst possible place.

Susan Redifer.

She was a prominent and influential figure in the new justice system, that she herself had penned. She was a sexual psychologist and everyone thought, because of her appearance, that she was some kind of dominatrix. She had some very disdainful views on men and was often writing papers on the male sexual appetite, and it was her unique view on quelling it, that caused upset among the male population, but unfortunately... her techniques got results. She was often appearing on TV interviews wearing skin tight body suits that accentuated her curvy figure and her large breasts, long straight black hair and sumptuous lips invited lewd comments. Which she took in her stride, attributing her attention to the obscene nature of the men and how their uncontrolled sex drive caused these "outbursts". It was easy to side with her, after all, was she wrong?

"So Miss Redifer, your new male correctional facility has been a smash hit in the justice system, nearly every inmate has been completely reformed after only 3 months. The results are dazzling!" the interviewer gushed.

Susan would just sit there and smile deviously whilst they showered her in praise.

"But the question on all of our lips is, are you going to be working on a facility for females?" he asked.

I'd noticed this was exactly the kind of question that pissed her off, anyone mentions anything about women getting the same treatment and she loses it.

"Well, just look at the figures. Statistically, most crimes are committed by men! I'm dealing with the most troublesome demographic here, female criminals just aren't the same kind of problem male ones are." she stated, factually.

I always hated how she would harp on about how she wanted a world where equality was at the centre of society, and then said sexist bullshit like this, she was a fucking hypocrite. Not that I was perfect, but knowing I was a male criminal just aggravated me even more when her face popped up on TV screens and newspapers heralding her as the end of male criminals. I felt like I was a dying breed, the last of the cowboys in the old west... except I was breaking into peoples houses and taking their stuff.

You have to understand though, I know what I'm doing is wrong, but I don't have any other choice right now. I was fired from my job because a female co-worker accused me of sexual harassment, which was completely untrue and she knew it, I was about to get her fired for stealing company money and she got in first. They suddenly they wouldn't hear my case and that was it, blacklisted.

So my life had taken a turn for the worse and I made an error in judgement. One crisp spring evening, I bypassed security on the biggest house in the area and entered into the place. I'd gotten good at this and I'd only take enough to keep myself going... to begin with, but like all things it spiralled out of control. I was getting ambitious and I'd not been caught. This lead to an over-inflated ego which came crashing down when the large house I'd broken into was owned by the very same person I'd see on TV every night. I was literally in the middle of opening a safe when she caught me. I still remember her wearing that nightie that left nothing to the imagination, she was more mad at me ogling her than she was that I broke into her house.

The court was quick to rule in her favour, I was literally caught red handed and she came down with the full force of the justice system she'd made on me. It was rigged, and I upset the rigger. I was to be transferred to her new correctional facility, I'd heard it was more of a 'prison', but all I knew for sure, was that it was anything but conventional. I was rushed through some waivers and paperwork since this was a "correctional facility" and not a prison, but it wasn't worth reading, they already had me, not a lot I could do at this point.

From the minute I arrived, the strong female presence was very noticeable, every guard was female, they all carried batons, had tight black shorts, big black boots and wore blue shirts that hugged their breasts snugly. For someone who respected women so much, it was hard to see how she wasn't objectifying them with these ridiculous outfits. They looked like strippers. I could see my escort's nipples poking out as I was lead down through reception! My mind wandered, as hypocritical as it was, maybe this place wouldn't be so bad if I got to see these girls everyday. As I scanned the place, the few males I saw were either doing maintenance or cleaning work, everyone else was behind bars or in cuffs, there wasn't a single figure of male authority in sight.

I was marched down several winding corridors and saw a lot of rooms with ominous signs outside them, there was a lot of moaning coming from rooms and hard slapping echoed through the corridors. It sounded like some kind of BDSM club, I passed a "milking" room from which I heard the sound of strained wailing, it sent shivers down my spine. Surely they couldn't do anything illegal in here? I hadn't been warned about this place, I hadn't been informed as to what my punishment would entail and all I knew was that I'd have to spend 3 months here and I was dreading it already.

My sentence felt very light, I mean, 3 months? For real? I should have done 2 or so years for that. That's what everyone told me, that I deserved worse. But the results of this place spoke for themselves, most prisoners were 'reformed' after just a month or two. I really couldn't believe it.

I was shuffled into an introductory room, lots of posters of the male genitalia were plastered over the walls, some technical diagrams and others looked like propaganda for some vaguely phallic plastic devices. Titles like "control your man" and "put him in his place" were in abundance. The two female guards shut the door behind me and stood next to me, I was already cuffed and it felt like I was about to be beaten-up as well. Sitting at a desk in front of me was the chief of the guards, a tall, buxom woman with jet black hair and the look of someone who had no sense of humour. The name on her desk read "Alice Chun". She sighed heavily and put down a magazine as she got up from her chair, assuring me that she was much bigger than me in her large black boots.

"Welcome to the Redifer correctional facility inmate, it would appear that Miss Redifer has taken a personal interest in your case, you are to be chastised your entire time here with us." she said firmly.

"Chastised?" I asked, unsure of what that meant in a place like this.

She nodded to the two female guards by my side and they grasped my arms firmly. She dropped to her knees and for a second I thought I was getting lucky as she dropped my work trousers and underwear.

"You're going to wear this chastity device, it will prevent you from achieving erections during your time here at the Redifer facility. Get used to it." Chun said, grabbing my balls and putting a ring of some kind around them.

I looked down and her low cut top was giving my a perfect view of her cleavage, with her also handling my dick, I couldn't hold back, in no time at all my dick sprung into life. Chun sighed again, even louder this time and I knew something bad was coming. She got back up and gave me a disdainful look before going over to a small freezer next to her desk and pulling out an ice pack, again, I could see what was going to happen a mile off, but it didn't prepare me for the shock of it being pushed into my groin. I yelped and tried to back away but the two guards held me in place as my dick shrank back down in no time, giving Chun enough time to finish attaching the device. A click of the lock on it brought smiles to the two guards faces.

I looked down at the shiny black device that now covered my cock, I could feel how tight it was, there was no room for growth.

"What the fuck?! Why do I have to wear this?!" I yelled.

Chun stood up in front of me, looking down with disgust as she attached a black key to her multicoloured key-chain necklace. They jangled as she moved.

"It's part of your recovery process, we can't have you exerting your male sex whilst you're here with us." she explained, the hint of a smile forming on the corner of her lip.

"Exerting myself?" I was confused.

"Now listen up, if you find your way out of this device, the punishment will be extreme, tampering with it will not be tolerated and you will report to the milking room every two weeks. Understand?" she barked.

I nodded, though remembering the sounds I heard coming from the milking room sent shivers down my spine.

The two guards pulled my trousers back up and I was guided through the cell block to my cell. Unlike what I was expecting, each cell was a solid concrete room with a bed and restraints on the wall. It looked like someone had modernised a medieval dungeon for convenience. They undid my handcuffs and pushed me into the cell, closing the door. I immediately pulled my trousers down to examine the device. It was solid and felt tailor made to make it impossible to slip out of, it wasn't coming off without me losing something essential, if I pulled on it, my balls got pulled too. I couldn't touch my dick whatsoever thanks to the hard plastic sheath. I didn't want to play with it, I don't want to get punished on my first day, I just wanted to tolerate this place until I could leave.

I tucked it back into my boxers and sat in my cell, what kind of bullshit was this? Fuck me, I wish I'd known about this insanity before I got assigned here, not that I could have done anything, she was determined to get me in here.

I sat down on the bunk and stared around the place, the whole cell was featureless, everything was a dull white or grey, the door was a dark green and had a little window with bars on it so I could see out into the corridor. I got up and walked over to the door and stared outside, to be greeted by the face of someone in the opposite cell doing the same.

"New here buddy?" said the gruff looking man in the opposite cell.

"Yeah, what the fuck is up with this place?" I said quietly, not wanted to get attention on my first day from the guards.

"It's not that bad, once you fall in, you won't want to leave." he said with a grin.

"What do you mean? This place seems like some kind of nut house!" I said, straining the volume of a whisper.

"Watch. Guard!" he yelled.

I backed away from the door and watched as a strong-looking girl with dark brown hair and powerful thighs came over to his cell and looked through the bars at him, tapping her finger against her thigh expectantly.

"What is it inmate?" she sighed, impatiently.

"I need to be punished, miss." he said, in a faux-innocent way.

"Oh, do you now? Get to the back of the cell, hands above your head." the guard said, lifting her baton and unlocking the door.

As the door closed behind her I couldn't see what was happening in the cell, all I could hear was muffled moaning echoing through the corridor. The male grunting got louder and louder until it suddenly stopped, there was a brief pause and then the door opened, I ducked out of sight as I heard the sound of the boots walking down the corridor. Whatever happened sounded sexual, but I couldn't tell what she did to him.

"Yo, man? What the fuck was that." I whispered across the corridor.

There was the sound of panting before he rose up to the bars again, he smiled a dopey smile.

"Oh.. yeah... that was great, they train them good here, she's a goddess that one. A goddess. You treat the guards right and they'll treat you right." he uttered, breathlessly.

"What the hell?" I asked again.

"Ask one, you'll see." he said, his face sliding out of view.

I wasn't getting anything else out of him. I sat on my bunk and instinctually rubbed my hands over the device I was trapped in. It constantly reminded me I was wearing it and hearing those moans caused things to stir below, but the confining nature of the device stopped anything from growing. It was kind of painful and awkward, I writhed about and lay down on the bunk. Trying to take my mind off things. This was so fucked up, how is this a correctional facility, what the fuck is going on here?

I stared off into space for a while daydreaming, I thought about Susan Redifers house, I wondered what was in her safe, I knew it didn't really matter to me, but I wanted to know what a woman like her would have in there? My mind drifted to her almost transparent nightie, her perky breasts and hard nipples sticking out of it in the cold, the fluffy seams of the nightie covering her front... Ouch. The cage struck back again, maybe it was because the damn thing being wrapped around my cock, but somehow I couldn't stop thinking about sex, and the more I thought about it the worse the pain got. I was supposed to wear this for 3 whole months? I'd barely gone 30 minutes and I wanted it off! I tugged down my pants until it was in view, black and glossy, locked tight to me like it was made to fit especially. I was so hard, it felt like I was about to burst out of it, but it was made of tougher stuff than I was. I put it away again and stared at the wall, the only way I was getting out of this pain was to stop thinking about stuff that turned me on.

My train of thought was interrupted as the sound of a baton hit the bars on my door.

"Lunch." came a female voice from behind the door.

The sound of the doors opening echoed through the corridor and we were herded out down to a series of small rooms, we were all separated into groups and pushed into one of them, the other prisoners seemed really eager for food, but I couldn't see what was going on, since I was stuck at the back of the group. We were split again into two groups and I could finally see ahead to what we were looking at. There was two guards, both wearing white outfits; white t shirts and white shorts, they smiled seductively. Then I saw it, between their legs was a dildo with a hole in the end. I didn't like where this was going.

"Come and get it boys!" yelled one of the guards rambunctiously, as she stroked the phallic shaped appendage between her legs up and down.

The crowd got more excited as they moved forwards, single file. I leaned out to see what was going down at the front of the queue. On the left was a small, meek looking guy with black hair and glasses and on the right was a large short haired man with the musculature of a bodybuilder.

A bell rang and the two men dropped to their knees and took the dildo's into their mouths and began sucking them. I was stunned, what the fuck was this? Was this some kind of BDSM prison or something?

"Aw, such a good boy! Eat up!" said the guard on the left as she patted the inmates head patronisingly.

The larger inmate wasn't getting the same positivity.

"Come on bitch, suck it down. Aren't you hungry for it?!" the guard said, putting her hand on the back of his head to push her dildo further down his throat. He coughed and spluttered as she let go, white liquid dripping from his mouth.

It's white, surely it can't be... My train of thought was interrupted by someone leaving the line. Oh thank god, I followed suit and walked out. I got some disapproving looks from the other inmates, like I was leaving the queue to get on a rollercoaster or something, screw that though, I'm not THAT hungry... but I knew I would be later and I would have to join them on my knees.

As I walked outside I saw the smaller guy who had finished and left the room.

"It's weird isn't it? This is the only way you get fed. Breakfast, lunch and dinner. No matter how many times I sit here, no matter how much resistance I put up, my mind says I shouldn't do this, I shouldn't want to do this... but my stomach always wins over my pride." he confessed to another inmate, in a voice that sounded defeated. I was uncomfortable thinking about the whole thing, it felt surreal.

It dawned on me that I'd have to get used to this, like everyone else in the room did. I would have to do this every day for 3 months, get on my knees in front of those girls with everyone watching. I shuddered at the thought.

After a while a buzzer sounded again, we were filed out into a large, square, outdoor area. I emerged out into the bright blue day, the hot sun beating down on me, the surrounding area was mostly the concrete walls of the prison, but on the far side, behind a gigantic wire fence, was open desert for as far as the eye could see. The pounding sun made a heat haze that caused the sand to ripple like waves on a lake. Around the corners of the quad were a few benches and that's where everyone seemed to be. Stationed at midway points on each side were more female guards, these ones sporting beige shorts and sunglasses, they were observing the area silently.

I went and sat down in the shade, looking across the quad, there were basketball hoops and other various sporting stuff, but no one was playing. Most of the prisoners were all gathered around where the guards were and chatting with them, or chatting at them, the guards didn't move or talk back. In the corner of the quad there were two guys were making out and getting handsy rubbing each others groins. I looked away and stared off into space for a while, not knowing what to do.

A voice came from above.

"Hey man, new here?" I tilted my head to see the same guy with the glasses who went first at lunch time.

"Oh, hi, yeah, first day." I replied.

"It's a lot to take in, but you'll get used to it, some of the other guys here love it." he explained.

I grimaced, I wasn't surprised, but still found the thought of liking it here somehow unpleasant.

"I have to ask you this, what's punishment in this place? Why is everyone so eager to get punished?" I asked.

The guys face turned sour, like I'd confronted him with something personal.

"Look, it's not something anyone is going to admit they like to their friends once they're out of this place, but whilst you're here, you can't get enough of it, it keeps you sane. I heard some of the guys even beg their wives and girlfriends to do it when they leave. We all wear these things, we all have to deal with that stuff you know?" he explained, vaguely.

"I don't get it." I said.

Before I knew it, a buzzer sounded again and the crowd pushed the two of us away from each other as we were filed into the cells.

I lay on my bunk staring at the ceiling. "It keeps you sane." he said, but what kind of punishment keeps you sane? I was going to have to find out, sooner or later. At least I learnt that I wasn't the only one wearing the device, I guess everyone was wearing one. The more I thought about it the more it made sense, but also the more it felt fucked up. Sexual frustration in this place must be off the charts. Then it clicked, the female guards have to provide relief of some sorts? There was no way Susan Redifer would open a prison where the female guards offered blow jobs or hand jobs to the inmates, that goes against everything the woman stands for. I realised I was getting hard again at the thought, this thing fucking sucked. The now familiar sting of pain was a sharp incentive to stop this train of thought. I picked up one of the books I was allowed to bring into my cell to take my mind off it, losing myself in the pages for a while, but no matter what was happening in the book, my mind kept thinking of the female guards in their tight shorts, of Susan Redifer in that skimpy nightie... It was intolerable. I hadn't had sex for a long time before I was locked up and coming here to this frustration filled hell was a nightmare.