The Chastity Prison

"If you want Miss Brooklyn to take care of you, you've got to take care of Miss Brooklyn. That is what you want isn't it?" she questioned.

It had only been a day or so but my mind was just boiling over with thoughts of sex, of how badly I wanted to bend her over the bunk and fuck her after seeing her ass. A pipe dream in my current situation. If there is something better her, I might as well go for it.

"Yes, Brooklyn." I replied.

"That's MISS Brooklyn," she stated, gripping me by my face and looking into my eyes, "now you're going to be a good boy and show me what you can do with your tongue."

She walked forwards and spread her legs a little, pulling my head between them and into her sweet smelling pussy. I was overcome with arousal, my cock was straining uncontrollably and my hands were desperate to break free, but I slid my tongue into her and she threw her head back and let out a stunted moan as she grabbed the back of my head by my hair and forced me in deeper. I persisted, licking away at her, a wide smile stretched across her face.

"Oh yes my little bitch, you're good at this." she whispered through pleasured moans.

I kept going, despite the pain and after a few seconds my head was pulled out by my hair.

"That's enough, this is your new duty, my little pussy licker. You belong to me now." she said grabbing the back of my head by my hair and forcing me to look into her eyes again.

She reached down to pick up the baton and as shameful as it felt, I couldn't help but get excited seeing her pick up the only source of pleasure I had. She slid it into herself right in front of me, I watched in tantalising anticipation as she inserted it slowly, right in front of my face. Her standing proud with the baton-cock sticking out a good 9 inches.

"Bend over your bunk cutie, or do you not want Miss Brooklyn to take care of you?"

I quickly bent over the bunk, shame had left me, I just wanted to get fucked.

"Good boy." she cooed, rubbing lubricant onto the baton.

*

The sex was mind-shattering, she knew what she was doing and she had been holding back before. Brooklyn fucked me like a pro, drawing out every ounce of frustration in me and leaving me a leaking, quivering wreck when she removed the baton from me. But still never pushing me over the edge, the sex always left me contented and relaxed, pacified... but I'd still need it again later. She was rough, crude and made me feel helpless, but also cared for. Though I felt like this was my fault and she was doing me a favour by fucking me this way. I guess in a twisted way, this was my fault.

The biggest shock came a few hours later, my first time in the showers. It was communal just as you'd expect, except everyone had the same device locked to their cocks. Even though I knew everyone was wearing them, it was different seeing people wear them. There was laughter and debating as they all spoke to each other about how bad they needed the guards to take care of them. Even though everyone had one, I was still ashamed to be seen caged and stayed in the corner, listening to the adventures some inmates had been through whilst here. It seemed the longer they'd been here, the more positively they spoke of the guards and Chun. I heard a few guys talk about Brooklyn and I felt a little jealous, some of these guys had been having her for months, admittedly not in the same way I'd experienced her today though.

Before long, I needed Brooklyn again, and again it came. Every morning I'd bury my face into her pussy and lick her until she slid that baton up herself and fucked me with it. As time went on I was less and less ashamed by it, she'd tease me about needing it and I'd thank her for giving me it. Two weeks passed by, sucking my meals out of a plastic cock, chatting with the guys in the quad and then getting treated to a good night fuck from Miss Brooklyn.

In a weird way I grew to really like her. Her demeanour was changing, less overpowering domme and more powerful girlfriend, her treatment of me softened, less hair pulling and more head pats for a job well done.

Two weeks after my first day I was called to the milking room. I'd been dreading this, even after chatting to the guys in the quad for two weeks, no one had revealed what went down in there but the older inmates spoke positively of it, so I knew it either had to be something really bad, or something really good. The whole thing was still a daunting mystery somehow. The name implied things I didn't like the sound of. Kara escorted me down to some chairs outside the milking room, and with me in cuffs, we sat and waited for the current session to end. It was a sound of male moaning, some of it sound pained and some pleasured.

"What the fuck is going on in there?" I asked.

Kara didn't reply, but just smiled menacingly. We waited a little longer until an inmate was escorted out feebly, him barely being able to walk properly. What the hell?

My escort stood up and pulled me into the room. Inside was a strange looking chair with a hole in the middle and some sort of drainage device below. Dear god, what the fuck was this?

Kara was about to shut the door when a familiar red-head pushed it open.

"He's mine, I want to do this to him." said Brooklyn.

"You know you can't claim inmates as your own Brook, Chun will kick your ass." Kara replied, all business.

"I... like this one." Brooklyn replied, bashfully.

"... Alright." Kara sighed before leaving the room.

Brooklyn perked up and closed the door behind her.

"Aren't you lucky! Your first milking with your favourite Mistress!" she said, reaching behind me as she unlocked my cuffs.

Oddly, I did feel a bit more relaxed knowing Brooklyn would be doing this with me.

"Now get in the chair." she commanded with a devious smile.

It was a strange looking contraption, I'd have to get in face-down and my arms would go in stirrups at the top and my legs in another set at the bottom. My face rested in a ring at the top. Everything had straps on it to hold me in place, directly above the groin was a hole where the drainage unit waited below. It was almost like a masseuse chair crossed with some kind of gynaecology recliner, it was intimidating and weird as all hell.

I slowly climbed into it awkwardly, resting my wrists in the upper stirrups and my legs in the lower ones, I felt Brooklyn strap me in.

"You shouldn't really need to get strapped in, you wouldn't disobey me would you?" She giggled.

"No Miss Brooklyn." I replied obediently, secretly smiling.

Despite how well she had treated me recently, her words were not reassuring, I felt her tug my trousers down leaving my ass exposed and the cage hanging precariously above the drain. At this point it felt like my balls were twice the size they were when I first came here from frustration. I really shouldn't have guessed that yet again my ass would be the entry point for this weird experiment. I suddenly felt Brooklyn's gloved and lubed hand probing my ass, I wriggled a little and a firm slap hit me across my left cheek.

"If you don't stay still you'll go back to your cell without."

At this point I didn't know what I was getting to figure what it would be like to be without it. Nevertheless, I tried to stay still as her fingers reached down further, then suddenly her other hand came up and grasped the cage from below me. I jolted back in reaction of being touched and Brooklyn's fingers hit my prostrate.

"Ah, there we are." she said, as she began to massage that spot.

I felt like I was being used, coerced into orgasm as she expertly squeezed my cage and probed my ass. I had no control over what was happening and gripped the contraption I was in even though I already couldn't move.

"You see, we can't have you getting unhealthy as a side effect of your little chastity cage, so we've got to help you release some built up...frustration." she said with a wink.

I tried to say something but couldn't find the words, then it hit me. A wave of pleasure like nothing I'd ever experienced before I felt like every point in my body was engulfed in an overwhelming feeling of ecstasy, cum gushed out of my cock through the open slit in the cage and into the drainage unit. I let out a long wail as the liquid drained from me. I could hear Brooklyn giggling behind me.

"There we go, I knew you'd love it, such a little butt slut you are." she teased.

"H-holy shit! What the fuck?!" I exclaimed, this felt better than any sex I'd ever had in my life.

"I could make this happen every day if you're a good boy for me." she said.

"R-really?" I asked, enthusiastically.

"Ha! You're turning into an enthusiastic little boy for my girl stick aren't you?" she replied.

I could barely catch my breath, that was incredible. I felt the straps being undone but I barely had the energy to move, all my muscles felt weak and useless. After a few minutes I pushed myself out of the chair and staggered to my feet. She walked up to me and put her arms around me.

"You were such a good boy, I'm proud of you." in that motherly tone she would do now and then.

She handcuffed me and the embrace ended. When she praised me, it felt good. She pushed me towards the door and helped me back to my cell, laying me down on my bunk. She uncuffed me and blew a kiss as she locked the door.

"I'll be back to see you later, get that tongue ready." she whispered before she left.

I lay there for an hour, mind blank in a state of euphoria. Holy shit.

*

Days came and went and my relationship with Brooklyn deepened, I couldn't help it, I developed feelings for her. Maybe it was love, submission or even Stockholm syndrome, but that short red-headed girl was always on my mind, I dreamed each day of eating her out and hearing her moan, and in return, she rewarded me with the girl-stick baton. She grew softer towards me, playing with my hair instead of holding me in place and chatting to me during quad time.

Through our conversations I learnt that she was single, shockingly good at maths, collected comic books and figurines and played cello in an orchestra, I literally couldn't believe she was as nerdy as she was based on how she acted at work.

We were sitting on the floor in the quad, separated by the chain fence. I explained to her how I came about being here and whilst she disapproved, which coming from her felt far worse than anything I'd been subjected to during the my time passing through the justice system, she could tell it was something I felt forced to do to survive.

"You were kicked out of your old job and took up theft and you were good at it. Why couldn't you just apply that drive to something else?" she asked.

"I guess I only did it because it felt like everything had been taken from me and I wanted to take something back. I thought my life was ruined! I'd spent years getting good at my trade and then suddenly it was out of the question, where else do you turn when the only thing you were good at you can't do? I'd never be accepted. It felt like the walls were closing in and I'd not be able to go back a normal life." I confessed.

I'd never seen Brooklyn look sad until now.

"There's always more options, other things you can do, you jumped pretty far into crime when there's always another option." her words made me hang my head, I knew that all along.

"I... know that now. I don't know why I thought I could keep it up, I guess I was just angry."

"Do you still feel angry?" she asked.

"No, just horny. ha." I laughed weakly, looking up at her.

Brooklyn rolled her eyes.

"Oh I see, you need some girl-stick do you?" she teased.

"Yes, Brook, so badly."

"Beg."

"Please Miss Brooklyn, please give me your girl-stick!" I feebly begged.

"Awww, well, I'll see what I can do." she said, getting up.

Her pert ass now eye level made me want to bury my face in there. I'd never wanted something so badly in my life, her body was all I could think of. It all began with her making me eat her out, but now I wanted it, craved it.

But it was all about to change.

I kissed up her thighs and she parted her legs in response, allowing me access. I buried my head into her willingly, she smiled in delight as my tongue went to work on her.

"Mmm good boy, you love it don't you?" she whispered erotically.

She knew I did, A manicured hand came down and ran through my hair as she let out little moans of pleasure, spreading her legs wider. A wave of pleasure hit her and she threw her head back reactively to my touch, her breathing got faster.

Then suddenly, Brooklyn pulled my head out and leaned down, kissing me on the lips. I looked up at her closed eyes and couldn't help but close mine too, embracing the moment. As she pulled away from the kiss she gave out a hazy smile.

"You know, when you get out of here, you should come see me. I'd miss you. Promise me you'll..." she trailed off as something caught her attention.

Her face turned pale and she started to pick her shorts off the floor. I didn't know what was happening.

"...what's wrong Brook?" I asked inquisitively, following her line of sight to the cell door where Chun stood. Looking in.

"Oh fuck."

"Get out here Brooklyn, now!" Chun barked.

Chun opened the cell door and behind her was Kara, brandishing a smug facial expression. Brooklyn didn't say anything, but looked back into the cell at me in despair as Chun pulled her out and slammed the door behind her. I got to my feet and ran to the cell door.

"What're you doing?!" I yelled.

Chun turned around and looked at me with disgust.

"Get back to your bunk, inmate. Your little girlfriend here has broken the rules too many times." she replied coldly as Brooklyn was escorted away.

I stood in the empty cell as the sound of footsteps disappeared down the corridor. I felt like I'd just been robbed, and a feeling of uncertainty came over me, I could still taste her. The rest of the day felt empty. I was drifting through the motions imagining Brook getting fired, what if I don't see her again? I never asked her number or anything, it's not like I needed to call it when she was here with me.

I should have been happy, I was being released the day after tomorrow, my time in this place was up. The guys said that I'd never want to leave because of how it's like in here, but with Brooklyn, I'd stay as long as I'd get to keep seeing her. I felt like a real sad bastard for thinking this stuff but it's hard to explain.

The only guard I saw for a while was Kara who kept smiling at me, it didn't take a genius to figure out that she was the one who told Chun what I was getting up to with Brooklyn, there was no way in hell I'd be begging her for punishment. I looked at her with disgust as she'd slow down by my cell door and do suggestive things with her baton to tease me. No matter what she did though, I refused.

The night came and went and before I realised it, the final day was upon me. I was cuffed and escorted into an office in the administration part of the facility by Chun who was in a surprisingly good mood, maybe she actually enjoyed releasing prisoners or something? As we enter the office, it was apparent immediately that the room was special, it was decorated with lush red furnishings, technical diagrams of chastity devices and a deep brown oak desk, it was a stark contrast to the rest of the prison which was mostly greens and greys. Behind the desk was Susan Redifer who barely looked up as I entered the room with Chun. Chun leaned down and removed my cuffs.

"Ah... you." she said, peeking up from her paperwork.

I didn't reply, cos I didn't know what to say.

"We're impressed with your progress and despite your mishaps with Miss Adams."

"..Adams..." I said out loud, I didn't know Brook's last name.

"You stayed caged the whole time, despite the temptation..." Redifer said, reading from a report in front of her, "very impressive, but there's one final task for you." she continued.

This caught me off guard, would I not be released if I failed?

Chun walked up to me and held out the same key she used to lock me up several months ago, but that wasn't the most eye catching thing on her. I had never seen it before... but there was a giant bulge in the front of her shorts. Chun smiled an evil smile as she moved her hand down to rub the front of her shorts and I watched, mesmerised as the bulge grew longer and thicker, until the outline of her large cock was unmissable.

"Either you take the key Miss Chun has in her left hand or take what she's offering in her right hand..." Susan Redifer said slowly and deliberately.

I'd spent 3 months sucking food out of rubber dildo's and bending over to get pleasure from batons, no matter what I did, I looked down at her cock as it pulsated in her shorts, it's thick length going nearly all the way to her thigh. It was huge! I'd never consider sucking a dick, but the guys promised what Chun could give was far beyond anything I'd received from a baton, I couldn't take my eyes off it. But I suddenly snapped away and looked at the key, I'd be able to take this fucking thing off! I reached my hand out towards the key but froze just before picking it up. Susan Redifer glared at me from behind her desk, eagerly watching my actions.

Is... is this a trap?

I didn't know what to do, do I choose freedom or pleasure? I looked down at her twitching cock once again and closed my eyes.

"Fuck it." I said.

When I opened my eyes my hand was firmly placed on Chun's hard dick and she smiled widely at me.

"They always choose it, don't they Miss Chun?" Said Redifer leaning back in her chair.

"That they do Miss Redifer." Chun confirmed.

I pulled my hand away from her cock as Chun closed the palm of her hand containing the key. I felt like I'd just fucked up in a way that would effect me forever.

"Well, you've passed, just like I suspected and you're free to go. But I'm afraid the cage stays on, this was all mentioned in the legal waivers you signed when you were assigned here." explained Susan Redifer in a way that made my blood turn cold.

"I'm stuck wearing this?" I asked, absent mindedly rubbing the cage.

"Yes. Now if you'll excuse me, I have business to attend to." she stated coldly.

I was lost, I had a lot more fucking questions but Chun dragged me out the room and despite trying to ask several different admin types about it on the way out, they all told me to refer to the waiver I was asked to read and sign when I arrived. I felt my soul leaving my body, there was no way this stuff was in the waiver!

I was handed my things and guided to the exit, as the door to the facility slammed closed behind me I realised I was free, but... not really. I'd be stuck wearing this thing forever, I sat down on a bench with my pointless belongings, what was I going to do? I still had no job, no future. I leaned back on the bench, looking up at the sky when a tuft of red hair brushed past my face.

"Hello cutie," said a familiar voice, "I decided to drop by since I knew you were being released today, well... at least most of you was being released. I guess I can help you with the rest of it!" Brooklyn giggled.

Maybe this wouldn't be so bad after all.