Progressive Prison

Author's note: The premise of this story is somewhat inspired by Vagrantx's

grim story "Encased," but it goes in very different directions from there. It's sort of consensual, but not very.

This is my first attempt at a 750 word story.

I walked down a long hallway, trying to control my eager anticipation. I knew the money I'd paid to visit here helped to run the prison. Very progressive, I thought. I found the door I wanted, Number Twenty-Seven, and opened it with the mag key I'd been given.

There she was, the one I'd picked from the catalogue. Twenty-three years old. Mid-length auburn hair, slender frame, medium-sized breasts now dangling seductively, fine, chiseled features, not all of them visible above the leather panel gag. On all fours on a Y-shaped bench with padded steel clamps holding her at her wrists, elbows, knees and ankles. Spread by the two arms of the Y. Plugged with a large and institutional-looking buttplug.

In for smuggling fentanyl, the catalogue said. She had probably brought in and distributed enough to kill dozens of unsuspecting users.

I removed my clothes and hung them on a hook. I admired her milky skin and perfect, rounded ass. Sometimes I leave the gag on, but I felt like a chat today. No hurry. I'd paid for an hour.

I unbuckled the strap and helped her get the attached stuffer ball out from behind her teeth. "Thanks. I sure get tired of wearing that fucking thing for six hours a day. Sometimes I like being face-fucked, just so I can have something different in my mouth."

"How much longer in your shift?"

She looked at the clock. "Another two hours. Then I'll get to eat, shower off the dried cum, and hang out in my cell until tomorrow. Frankly, I'm glad you're here. I don't like being fucked by strangers, but it breaks the monotony of being clamped down like this all day."

"Are you glad you chose this way to work off your sentence?"

"Glad? Sometimes not, when a customer is especially brutal. But they're not allowed to really hurt me, and six months of this sure beats ten to fifteen years in the regular can. And at least here there are rules. Not like being raped by other inmates."

I reached under her for a double handful of dangling breasts and squeezed, firmly but not harshly. I was surprised to feel her nipples harden.

"You like that?"

"Told you. It breaks the monotony, so I try to enjoy it. Besides, you're not pinching and twisting like some do. The women are the worst."

I ran my hand over her ass. She said, "See anything you like?"

"Indeed I do." I ran my hand over her asshole. "I fancy this. Most women won't do it. That's why I'm here."

I eased out the buttplug. What a monster—at least eight inches long and thick as hell. Not a sex toy-- a punishment tool.

I took pump of lube, a requirement for penetrating either bottom hole. I rubbed it in her asscrack and into her rosette, and put some more on my cock. I put my cockhead against her asshole and started to press. Her sphincter resisted a bit, but not much since it was still gaped from the plug. My cock slid in until my balls rested on her taint. Then I began to thrust.

I love assholes. They're so tight, and slightly forbidden. As I picked up speed, her body slammed forward, making her tits roll up and down on her chest. But I could feel her pushing back as well, obviously trying to give me, and herself, a good ride and maybe get herself off.

After a while, she began yelping rhythmically. Good, I thought. She's obviously learned to suck some enjoyment out of this. It made me feel slightly better about fucking the living daylights out of a helpless woman.

My dick pulsed and my abdomen clenched as my orgasm began to erupt. She was building to a climax as well. I pushed all the way in, held, and spurted cream far up into her body as she came with a guttural scream.

I held in my softening cock for a minute while we both panted and recovered. Then I slid it out and pushed the buttplug back in. I knew that staff would come in and do a proper cleanup for the next customer, but I always like to leave things the way I found them.

I walked around to her head end. "Great ride, girl. We'll do it again as soon as next payday comes around." She opened her mouth and I slipped the ball behind her teeth and buckled the strap.

"See you."