Written by a boi after a roleplay session
They called it on remand, but it felt more like a sentencing being served on me.
I was left alone in the holding area, the echo of voices leaking through the door. I could hear them talking about me—mocking me. One of the voices was hers, Warden Helen Ryder. The same woman who had processed me before, who’d stripped away my dignity and my name. I wasn’t who I used to be. I was Davina now—her creation. I hadn’t chosen that name. She’d bestowed it upon me like a branding iron.
The door opened, and there she was. Warden Ryder, dressed in a short black dress, black tights, and knee-high boots that clicked with authority on the floor. She looked stunning, in a way that made your blood run cold. Power in heels. She looked me over and said, “So you’re back. Clearly, you didn’t learn your lesson last time.”
“I’m innocent,” I mumbled. “I was fitted up.”
She ignored my protest. “Empty your pockets.”
I hesitated. Her glare intensified.
Her eyes narrowed, and I felt her dominance tighten like a noose. Reluctantly, I turned out my pockets—two pairs of grey lace knickers dropped into her hands.
“I don’t know how they got there,” I stammered. “They must’ve been planted.”
She didn’t buy it for a second. She reached forward, her hands rough and searching, patting me down for any other secrets. Finding none, she issued the order: strip.
I peeled off my vest, my socks, my shorts… down to the lace knickers I forgot I was wearing. She raised an eyebrow and sneered, “And how did these get here? Were they planted as well?” Her voice dripped with sarcasm, like she already knew the answer and just wanted to watch me squirm as I denied it.
They came off. I stood there, naked. Exposed. Already starting to feel like I belonged exactly where she’d said I did—beneath her.
She didn’t give me time to wallow. “On the chair,” she snapped, pointing to a heavy-duty bondage chair in the corner. I walked over, aware of every inch of skin on display under her cold stare.
I was strapped in tightly—two straps for each arm, one for each ankle, and another across my torso. Then came the gag—a thick ball that silenced me before I could protest. She spat on my face. Not metaphorically. Literally. And said she’d only remove the gag when I was ready to confess.
Her vampire gloves came next. Sharp metal tips bit into my skin as she ran them down my torso. My thighs. My nipples. My exposed cock and balls. Pain pulsed through me in waves I couldn’t control. I twisted in my bonds, groaning behind the gag. Her eyes glittered. She was enjoying every second of my torment.
Nipple clamps followed—tight, merciless, with a chain she tugged whenever she fancied watching me flinch. She left me there, the agony building, while she casually picked out her next tools: a crop, a paddle, and a small whip. I watched in fear. She knew it. She wanted it that way.
Then the beatings began. Thighs. Nipples. The occasional wicked strike to my cock and balls. She paused, tilted her head. “Ready to confess?” I shook mine.
She didn’t hesitate—she brought out the zapper—a red handheld device with a visible spark at the end. Just seeing it made me panic. She didn’t hesitate. Zaps to my chest, my thighs… and then, the tip of my cock.
I screamed. As best as anyone can through a ball gag.
She leaned in and asked again if I was ready to confess. This time I nodded.
She removed the gag.
“I—I stole the panties,” I choked. “From a washing line.”
She raised an eyebrow. “Why?”
“So I could sniff them…”
She sneered. “Panty sniffer. Maybe we should tattoo a washing line on you—add a new pair of tattooed panties each time you come back.”
Her eyes never left mine. She kept saying how disappointed she was. How she’d hoped I’d reformed. But clearly I hadn’t. And now, she said, Winston had heard I was back. So had his brother, Marcus. They were already talking about taking turns with me. I begged her not to put me in a cell with them.
She just smiled and said, “You’re not going straight in with the other inmates yet, Davina. First, I need to get you ready.” That didn’t sound like a reprieve.
I was marched to the spanking bench. My legs were strapped down, wrists cuffed, and the nipple clamps — still biting into me — stayed put. She said she liked the look of me squirming. I could feel pre-cum dripping; she noticed too. “You’ll be drinking that later,” she said, slipping a condom over me. My stomach twisted.
She stood in front of me now, legs apart, her stance commanding. “Training begins,” she said flatly. “Start by licking my mistress cock.” I lowered my head and began with the tip, slow at first, my tongue exploring the ridge. Then deeper, taking it in as far as I could, knowing she was watching closely, judging every movement. I could hear her breath catch once — whether with amusement or approval, I couldn’t tell.
Then came rimming practice. She formed a circle with her thumb and forefinger and barked the order. “Get that tongue working, Davina.” I obeyed. Circling, pressing, trying to please. I was dripping with shame and arousal — a cocktail I was beginning to accept as normal in her presence.
I barely had time to catch my breath before she moved behind me. Lube. A finger. Then two. I gasped — her voice was calm, controlled. “You’ve got more to come.” And she was right. I barely processed the transition from fingers to strap-on before I was being pegged — hard, deliberate thrusts that left no room for doubt about my place. She moved to the front again, forcing a dildo into my mouth while continuing to thrust behind me. I was being spit-roasted — my first time — and she knew it. She made sure I knew what was expected. “Many men will want you. You’ll take them one after the other. You’ll swallow what they give you, and they’ll fill you from behind. That’s your future, Davina.”
Then came the question: “What does PB stand for?”
I answered with trembling clarity: “Prison Bitch.”
“Exactly,” she said. “And that’s you.”
As she pulled out, she let the dildo slip from my mouth. I was panting, drooling slightly. The flogger came next, and with it, no mercy. The lashes rained down on my back, then my arse. Each strike built on the last, overlapping bruises and welts. My cries grew louder. “Too noisy,” she snapped, and the gag was pushed back between my lips.
Then it got worse.
She switched to the riding crop — shorter, sharper, more punishing. My body bucked as much as the restraints allowed. Dribble leaked from the corners of my mouth, and I could feel it hanging from my chin. My nipples were still clamped — the pain there a steady fire beneath everything else.
Eventually, she stopped.
She released me from the bench, but not with any gentleness. I was ordered straight down onto the floor — “where you belong,” she sneered. My body ached, my skin was on fire, my pride in tatters. But I obeyed without hesitation.
She presented her boots. Tall, black leather, worn from a day of rounds. She told me they’d walked across cell floors that were sticky with inmate filth. One particularly memorable detail — she informed me that an inmate had recently cum on his floor, and she hadn’t bothered to sidestep it. That residue now mingled with the dirt I was expected to clean… with my mouth.
I started on her left boot. She placed her other one square on my back, applying pressure as I kissed and licked, beginning at the toe and working up the outer edge, around the heel, even reaching inside. I made sure to show proper reverence, my humiliation complete as my tongue traced every crevice.
When I moved to the right boot, she shifted her weight, this time pressing her sole down on my hand — pinning it in place, a silent threat not to slow down. I continued cleaning, licking along the leather, the edge of the sole, the inside rim.
Then came the worst part. She turned her back on me, lifted each boot just enough to present the heel — and ordered me to clean the underside. I obeyed. The taste was bitter, foul, and degrading, but I did it. I licked the soles of her boots clean, like the degraded prisoner I’d become.
Still reeling from the humiliation of licking the soles of her boots, I was ordered onto the bondage bed. My nipples throbbed relentlessly from the clamps — they’d been on for over an hour by now — and the pain was searing through my chest. I dared to ask if they could be removed.
“Permission denied,” she said, enjoying my suffering.
She cuffed my wrists to the sides of the bed, tied my ankles tightly together, and then strapped my torso down onto the Fetters board. I wasn’t going anywhere. I was completely at her mercy — again.
Eventually, she removed the clamps — one at a time — and each removal sent a white-hot surge of agony through my chest as the blood rushed back in. I screamed through clenched teeth, my body writhing against the restraints, utterly powerless to escape the searing pain. My back arched involuntarily, hands straining at the cuffs, eyes clenched shut as the intensity overwhelmed me. “Do they need some TLC?” she asked, her voice thick with mock concern. I could only nod, breathless, desperate for even a sliver of mercy. Instead, she leaned in with a smirk and gave each raw, tortured nipple a brutal squeeze and twist, drawing another gasp from deep in my gut. The sadism in her eyes made it clear: she was only just getting started.
The condom she’d earlier placed over me — to catch the dripping pre-cum — was now removed. Its contents were smeared around my lips. I felt even more degraded, but I didn’t dare resist.
Then came the paddle again. She struck my thighs, then gave the occasional punishing blow to my cock. She commented on the red marks the paddle left — she liked them. Of course she did.
She told me she needed to extract a sample. “We don’t want you getting too eager when the other inmates get their turn,” she said, almost casually. She brought out the milking machine, calling it “the last vagina you’ll feel for a while.” It started slowly — teasing — then picked up speed. But just as I was about to cum, she’d stop. Again and again.
Finally, she said, “Actually, I’ve decided you don’t get to cum today. I’m going to leave you here… to stew.”
I lay there, bound and aching, my cock throbbing, my mind a storm of frustration and regret. I’d brought this on myself — or at least, that’s what she wanted me to believe.
But she wasn’t quite done.
She returned with a flannel. It stank — acrid and unmistakably foul. “Piss-stained,” she informed me, she covered my face with it. “If you want to cum, you’d better breathe it all in.” It was repulsive, but the need to release had overridden my pride hours ago. I inhaled deeply, the humiliation flooding my senses, layered on top of the physical torment.
Then she began stroking me. I didn’t stand a chance. My body was exhausted, teased to the brink and dragged back too many times. The orgasm tore through me, sudden and violent. I cried out, more in shame than pleasure, as I spurted uncontrollably onto my stomach.
She paused only briefly before scooping it up, holding the sticky mess before my lips. “Open,” she said.
I hesitated — just for a second — and she narrowed her eyes. That was enough. I obeyed. I opened my mouth.
It was warm, bitter, and thick on my tongue. My own cum. She made me hold it there, look into her eyes, and swallow it slowly. There was no pretense of arousal left — this was pure degradation. But somewhere beneath the shame… was submission. Acceptance. Perhaps even relief.
I had no name. I had no power. I was hers. Davina.
With the final act of my humiliation complete, she unfastened the restraints one by one. My wrists were sore, my nipples throbbed, and my thighs burned from the relentless punishment. I could barely move, but she didn’t care. “Up,” she ordered, and I stumbled to my feet — naked, used, and dripping.
My legs trembled as she marched me to my cell. Lube was still leaking from my arse; my face was streaked with dried urine and cum. I couldn’t even look at her. Not from shame — that had long since passed — but because I knew she was proud of what she’d done. Proud of how thoroughly I’d been broken.
The cell door clanged shut behind me.
I slumped onto the cold bench, dazed and wrecked. My body marked with bruises and welts, my lips tingling from where the condom’s contents had smeared. My nipples ached with every breath, still raw from the clamps. My mind was spinning — part shock, part surrender.
I was no longer Dave. Not even Davina. I was just another inmate. Just another Prison Bitch.
And now… now I was waiting. Waiting for Winston. And his brother, Marcus.
They knew I’d arrived.
They were coming.