Prisoner of the Warden
The door closed behind me, sealing my fate. Mistress Helen stood before me in a tight red latex dress, a customised punk jacket over her shoulders, her presence commanding. I barely had time to register the sharp glint in her eye before her voice cut through the air.
“Strip.”
I hesitated, a flicker of resistance surfacing. This was new—I wanted to see how far I could push myself. Slowly, I pulled off my clothes until I was left in nothing but the feminine knickers I had chosen for this occasion. I feigned innocence.
“Even these?” I asked, as if I didn’t know exactly what she’d say.
She raised an eyebrow, stepping closer. “What are these? Did you steal them?” The accusation hung in the air, and I felt my cock twitch at the interrogation.
I muttered a weak protest, but it was useless. The knickers were pulled down, my humiliation complete.
“You will address me as Warden,” she continued. “This is a remand centre. You will be held here until trial. Confession will make your stay much easier… but I doubt you’ll take the easy way.”
A sharp, playful kick to my hard cock made me gasp. Then, before I had time to recover, she kicked me again and then grabbed her rope, expertly binding my cock and balls in tight restriction.
“On the bed, prisoner,” she commanded.
I obeyed, lying face up as she cuffed my wrists to the bedpost above me. My ankles were tied together, secured to the frame. Trapped. Vulnerable.
A sharp slap across my face snapped me to attention. I gave her a defiant look. “That didn’t hurt.”
She smirked and reached for the cane. A swift, merciless strike against my thighs. A second. A third. I hissed, the pain immediate, the marks blooming across my skin.
“Like a ripe peach,” she mused, admiring the welts already forming.
She took a mouthful of water, then spat it over my face. The shock made me gasp. The next time, she made me open my mouth and swallow. Again, and again.
She clamped my nipples and forced me to hold the cane in my teeth while she left the room, with a warning to not drop it or there would be consequences, claiming to “process another prisoner.” The silence made my heartbeat louder.
When she returned, she ripped off the clamps in one brutal motion. The sting made me cry out.
“Confess,” she demanded.
“I didn’t do anything,” I insisted, breathless. “Mistaken identity.”
The cane struck again. And again. A sudden zap to the end of my cock made me jolt. I bit my lip.
I broke. “Alright! I stole… women’s knickers.”
She tilted her head. “Just panties? Or were there bras and stockings too?”
I swallowed. “All of them.”
She smirked, then slipped off her own knickers—ones she had been wearing all day—and forced them into my mouth. The scent, the taste—it overwhelmed me. “You like panties so much, wash them, chomp on them like a washing machine”
The confession was not enough. She removed the rope from my cock and balls and replaced it with a dozen clothes pegs, snapping them onto the sensitive flesh. My nipples, already sore, received two each.
Then the cane returned. It struck my cock. Again, and again. I screamed into the pantie gag.
“Tell me what you did with them,” she ordered.
Muffled words through the panties: “I… I wore them. I… masturbated into them. Then… licked them clean,” I gasped between breaths.
I begged for mercy. Slowly, she removed the pegs. Agony flooded through me as the blood rushed back, each pulse an explosion of pain. I writhed, overwhelmed by the sensation.
She left the room again. When she returned, she pressed a new pair of knickers into my mouth—warm and damp. “I needed a piss,” she said casually.
Before I could react, she hoisted my ankles up and tied them to the roof of the bed.
The first strike of the cane to my exposed backside made me cry out. I squirmed in my restraints, but there was nowhere to go, no way to escape. The cane fell again. And again. My body jerked with every impact. I howled, my cries muffled by the soiled knickers stuffed in my mouth. My exposed flesh burned, each stroke layering pain upon pain.
The Warden showed no mercy. She relished my torment, delivering relentless strikes until my struggles weakened, my body trembling with exhaustion.
Finally, she released my legs, letting them drop heavily onto the bed. My cuffs were unclipped, and I was flipped onto my stomach. Before I could catch my breath, my wrists were locked back into place.
And then came the flogger.
The first strike landed across my shoulders, a burst of fiery pain spreading through my back. Again. And again. The strokes rained down in a merciless rhythm, covering my back, my arse, my thighs. I screamed into the pillow, but she didn’t stop.
“Too loud, prisoner,” she remarked.
A moment later, a rubber gag was forced into my mouth, securing my silence. The flogging continued, even harder now. My whole body felt like it was on fire, every nerve-ending raw.
Then she switched tactics. A sharp prickling sensation swept over my skin, making me shudder. The pinwheel. She rolled it over my back, my sore arse, my thighs—tracing over the welts she had just created. The contrast of sharp and dull, sting and ache, made me groan into the gag.
Her voice was soft now, but no less cruel. “Such delicate skin… A slender boy like you will get a lot of attention from the butch boys in prison.”
A pause. A hand running possessively over my arse.
“Winston will take one look at you and decide you’re his wife.”
Something cold pressed against my hole. A moment later, the plug slid inside me. I gasped at the intrusion, feeling the stretch, the fullness.
“This is part of your training,” she explained, pushing it in deeper. “You’ll need to be ready for the men who’ll claim you on the inside.”
Then the whip cracked against my arse.
My whole body jolted, but the plug stayed firmly in place. The whipping was relentless—long, searing lashes across my already punished backside. My muffled cries filled the room, but she was relentless. Every strike made the plug inside me feel even more intrusive, more humiliating.
Finally, she released me from the bed and stood over me, her strap-on in hand.
“On your knees.”
I obeyed, my body trembling. She pressed the tip of the massive strap-on against my lips. “Suck.”
I took it in, starting with the tip, but she had no patience for that. She grabbed the back of my head and forced me down onto it. I gagged, my eyes watering as she pushed me to take it all the way.
“Look up at me,” she ordered.
I did, my mouth full of her cock, my humiliation complete.
“Good slut, you’ll be sucking plenty of cock to keep the boys sweet” she smirked.
Then came the real test.
I was ordered onto the spanking bench, wrists tethered to the front, my arse completely exposed. The plug was removed. A slick finger pressed into me, then another. She worked me open with ease, teasing me, preparing me.
The smaller strap-on entered me first. It slid in smoothly, stretching me in a way that was foreign but… not unwelcome. She moved inside me, thrusting steadily, filling me.
But she knew it wasn’t enough.
She switched to the larger strap-on—the one she had made me suck.
She positioned it against my hole. “Relax, Davina. It will be easier that way.”
Then she pushed in.
It was thick, stretching me wider than before. I gasped, my fingers clenching into fists as she eased in. She took her time, but once the head was inside, the rest followed. I felt full—completely and utterly filled.
She started to thrust. Slow at first, teasing me with each movement. Then faster. Deeper. I could feel her hips pressing against my sore arse cheeks with every stroke.
“You’ll be of great service to Winston,” she murmured. “He’ll claim you as his.”
I whimpered, overwhelmed by the sensation, by the humiliation of being used like this.
When she finally pulled out, I was left shaking. But she wasn’t finished.
“Six of the best,” she announced, grabbing her cane.
The first stroke was brutal, cutting across my already tender skin. The second was worse. By the third, I was crying out. By the fourth, my body was convulsing. By the sixth, I thought I couldn’t take any more.
But she wasn’t finished.
“Six more.”
I used my safeword after the first, gasping for mercy.
She allowed me a moment to breathe before delivering the final strikes—firm, but not as brutal. My whole body trembled.
I thought it was over.
“On the floor,” she commanded. “Masturbate into my panties.”
I obeyed, my hands shaking as I gripped myself. But she wasn’t going to make it easy.
She pressed her bare feet against my face. They smelled of sweat and leather from a long day as the Warden.
“Worship them,” she ordered.
I licked, sucked, kissed—humiliating myself under her watchful eye.
Then the whip struck again.
I gasped, my arousal mixed with the sharp sting of pain. She whipped me as I stroked myself, forcing me deeper into submission.
But no matter how hard I tried, I couldn’t finish. The pegging had left me too overwhelmed, too drained.
She noticed.
“Pathetic,” she sneered. “Fine. If you can’t cum in them, you can clean them instead.”
She shoved the piss-soaked panties into my mouth.
“Suck them clean.”
I obeyed. I had no choice.
Finally, when she was satisfied, she stood over me, smirking.
“Welcome to the system, prisoner.”
