The Chastity Prison by chlomo,chlomo

She grabbed my shoulders and flipped me onto my back, I didn’t want to fight her but I didn’t want what was coming either, pulling my legs up into the air by my ankles she pushed the tip of the baton towards my asshole. I was mortified, what the fuck had I gotten myself into? I was about to protest but she smacked my ass hard.

“Don’t you want your punishment?” she asked.

I stayed still and through all of it, maybe due to the sight of her big breasts jiggling with each movement or how cute she was, but I was still straining in my cock cage. I winced as she eased the baton in.

“There’s a good boy.” Kara said in a motherly voice, squeezing my ankles as she slid the baton deeper into me.

It hurt and I writhed about trying to somehow escape the pain, but as it eased, I relaxed and accepted the invasion. I felt ashamed that I’d let this happen, no, that I asked for this to happen! I’d just have to tolerate this and then I can pretend it never happened and I’d never ask for this again, why the fuck did I ask for this to begin with, what kind of fucking idiot asks for punishment?! Kara started to thrust in faster, her smile turning into a wide grin as she was obviously enjoying this too. Suddenly she touched something inside me and I felt a brief rush of pleasure and let out an involuntary moan, Kara noticed.

“There we go, oh yes you’re going to be asking for this every day I bet.” she said, teasing me as she repeatedly hit the same spot, I felt helpless but the pleasure inside me was undeniable.

She licked her lips slowly and seductively, you could tell she was enjoying this more than she should. I put my hands over my face and mouth as she picked up speed yet again, the feeling of pleasure inside me at an almost constant stream. Then abruptly, with a long moan, she withdrew the baton. She must have cum. I felt the pleasure die down inside me slowly, I felt unfulfilled, short-changed, and ashamed that I didn’t want her to stop. Kara removed the baton from it’s place between her legs and zipped up her black shorts.

“Well, better luck next time.” she said, mockingly. She ran a hand over my caged dick and inner thigh with a smile, I twitched as a response and she giggled before pointing to the wall.

I got up, pulled up my work pants and stared at the wall as she backed out of the cell, locking the door behind me.

What the fuck did I just do? I just got fucked by a girl… and I almost came. I realised that I wasn’t horny any more and the buzz and thoughts had just faded away.

“Got Kara on your first time? What a lucky guy.” said the voice from across the corridor.

That guy had heard what had happened. I felt embarrassed, but I remember he’d asked for it too, so at least he was no better off than me, but I still felt ashamed.

“…yeah.”

“She’s a real cutie that one, very good at hitting the right spots am I right?” he said conversationally.

“Look man, I don’t really want to talk about it.” I bluntly replied.

“Haha, well, in a weeks time, it’ll be all you want to talk about and we can compare them, they are all goddesses, all of them.” he said again.

“Yeah. I’m sure.” I said sitting down on my bunk.

I felt violated, but part of me couldn’t deny that it was kind of hot, maybe I was just attracted to Kara. I felt that weird come-down of sanity after you orgasm but I’d not orgasmed. This was a lot to process and I was feeling dirty all over. But it did ease the frustration, that much was true.

I laid down, spacing out for a while thinking about what just happened. Whilst I tried to process it, the buzzer sounded and “dinner” was shouted down the hall. I was hungry this time, I’d have to use those weird things in the lunch hall if I wanted food, and after what I’d just been through I wasn’t sure I wanted to.

I followed the line down the hall and various guards kept a watchful eye on us, I saw Kara standing by the door to the lunch hall, she saw me looking at her and winked. I looked away, I’d always wanted to have sex with a girl like her, but… not like this. We were herded to the same rooms as before, this time I got forced into second place unwillingly, seemed most of the people on my side of the queue were also newbies reluctant to go first. The guy in front of me was eager to get going and the second the buzzer sounded, he dove to his knees and began licking and sucking the dildo between the girls legs. Kara was on the right this time, I was on the left, I didn’t want to have to do any more humiliating things in front of her, but there wasn’t much choice, I was too hungry to go without. The guy in front got up and and with a big smile licked the white liquid off his lips and headed to the exit. I was pushed forwards.

The girl in front of me was a brunette with a grim looking face and thighs that looked like they could crush a watermelon. She clearly worked out, her biceps were nearly as thick as her thighs. Her badge read “Ingrid”. She reached forwards and pushed me down to my knees, the dildo pointing into my face. I really didn’t want to do this, but with the medusa stare of the guard I opened my mouth and moved it towards the dildo.

“I don’t have all day inmate!” she said with a impatient but seductive eastern European accent. Before I could do what she asked, I found my head being pulled onto the toy and it suddenly thrusting into my mouth.

I coughed as some of the liquid from the tube was shot into my throat… it tasted of chicken? Chicken in white wine sauce?? I was confused, but pleasantly surprised. Still spluttering, I looked around to see if others were laughing at me.. but… nothing. Everyone was either looking eager or looking worried. I didn’t feel any shame suddenly, no one cared if I was doing this because everyone was either doing it or going to be. I sucked on the dildo and without much work, the food kept coming. I looked up and the guard was almost smiling.

“See, just needed a firm hand to encourage you to be good.” she said in a way that made me a little uncomfortable.

Another minute of tentative sucking proceeded, I felt the action of mildly arousing to my shame, not the action itself, but seeing her thighs and the feeling of her hand on my head, I was starting to strain in my cage when she suddenly pulled it out my mouth and cleaned it off.

“You’re done, unless you want some more later?” she teased, waving the dildo around suggestively.

I smiled weakly and left, walking past people on the way out; nobody reacted to what I’d done at all, it was oddly relieving. I sat outside and once again saw the smaller guy. He saw I’d been in this time and tried to start a conversation.

“See, it’s not too bad once you get used to it.” he said, forcing a smile.

“Why can’t we just have a regular cafeteria, like, every other fucking prison?” I asked, sincerely.

“It’s part of the rehabilitation. Everything around here is designed to break down your toxic masculinity.” he explained, as one of the larger inmates licked and sucked his fingers on the way out of the dildo room.

“I guess this is pretty humiliating, but if everyone is doing it then it’s not so bad.” I stated.

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