The Tale of the Jail - Cover

The Tale of the Jail

Copyright© 2019 by Jo Singleton

Chapter 1

Erotica Sex Story: Chapter 1 - Jails exist that torture their prisoners for information. This one used a whole new approach. It tortured its inmates with sex. The jailor, Shannon, took her job very seriously. Well, she loved it, to tell the truth. The men incarcerated there gave her all manners of satisfaction. She had no complaints. Nick and Jack were there to spill highly confidential secrets. Only when they did, could they spill other...elements.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   FemaleDom   Double Penetration   Fisting   Masturbation   Oral Sex   Sex Toys   Squirting   2nd POV  

The prisoner’s hands were chained to the wall above his head, rags on his back. They had brought Nick there not two days ago. Sweat ran from his matted black hair down his taut body. The guards allowed him out of the iron cuffs at night for sleep and other needs. In the morning, the jailor forced him up to this horribly uncomfortable position.

From where he stood, Nick could see the massive bars separating him from the passageway outside, and beyond to the cell across from his. That cell held another prisoner, his only other inmate in this place as far as he knew. There were no lights here inside, only in the passageway which meant a dimly lit cubicle on both accounts.

Those brought to this wing had information to spill willingly or not. If not, they must endure torture. Of the cruellest kind. Not the type that hurt or drew blood, but that produced frustrated, unfulfilled screams. The method here was rather ... unusual. Sexual torture.

There was no secret in the fact that the male of the species produced loads of sperm. They would seek to ejaculate it at any cost as they strived to scatter their genes everywhere. In this prison, their genes ended up mostly on the stone floor as the countless and timeless whitish stains shot all over the place attested. The approach must be successful if each of them witnessed an information spill to go with them.

Nick’s imagination leafed through the probable procedures to achieve this literal bucket-full of yield. Sex toys maybe? He remembered an ad on the internet of a male masturbator. Working on battery, it had a silicon-smooth tube inside a box. When you put it on, it heated and wrung in circles; a gel tube came in the pack for you to smear in the inner layer. The seller had uploaded promotional videos on a porn site.

Curiosity took him to one of the links. In that video, the camera zoomed on a tied guy’s hips with the sex toy latched to his penis. Someone else operated the camera and the male masturbator. The machine started moving around his erection as the microphone caught disembodied groans. Its whirling went on for about five minutes with a whining sound. The man’s hips sprung upwards as if a woman was wriggling on his dick. Suddenly, a yell came out of the video as the hips jerked in frantic movements with the guy’s apparently intense orgasm. He moved so mindlessly that the machine popped out of his big, wet dick.

But the footage was not finished. The camera operator lifted the vibrator and Nick saw it dripping in cum. The operator’s finger lifted the spent member to latch it back on the toy. And increased the speed. Boy, the guy screamed in pleasurable agony for his dick must have been sensitized with the first ejaculation. The whirling moan of the device made you imagine the extreme pleasure punishing the man. Nick’s six-inch erection had manifested its own opinion on the marketing strategy. The machine worked the poor man up, and his increasing groans together with the fast-up-and-down hips signalled his state. He yelled even louder and moved even faster as he shot jets and more jets inside the silicon lining.

The toy had a third speed, which the operator made it a point to show at once. By now, Nick’s prick stood rock-hard and at bursting point. But in no way was he capable of ungluing his eyes from the computer screen. The poor man virtually suffered when the operator clicked the highest rotation. His moans denounced agony. But in less than fifty seconds he was bellowing on the top of his voice and his spine arched out of the bed only for him to deliver no cum at all, merely the ragged spasms. It had sucked the man literally dry.

The footage had pushed Nick to the edge. He had to scrape his chair back and run to the bathroom, holding his bulbous crotch. Inside, he tore down his jeans and briefs, fell on his knees before the toilet, his hand tunnelling his dripping mast. He had time for only two strokes before his cum scooted out in long, fat jets into the water.

He should have ordered the damned thing and had as much fun as possible. Even if he got addicted to it and uninterested in real sex. Now they dumped him in this hole to be mishandled in unimaginable ways.

When his mind hopped back to the present, he saw he was raging hard. Hell. He inhaled deep a few times to make his hard-on subside since he could not touch it to jerk off. But a noise in the corridor interrupted his concentration.

The opposite cell’s bars clanged as the jailor opened it, entered and turned the lock. The jailor was a woman. A very ... womanly woman, if he could say such a thing. Big boobs, large hips, dark hair, mid-thirties. In military uniform and black boots, she evoked fantasies of the most explicit kind. If she was in charge of the ... spilling of information together with other elements, Nick was screwed, she did inspire a cock-stand.

In the other dimly lit space, a chained man eyed the jailor wearily. Nick discerned mostly shadows, but clear enough for him to understand what happened. From his viewpoint, Nick could tell the prisoner was bald and short, much shorter than his own six feet something. The play of light and shadows gave the impression that his neighbour owned a charmless beer belly.

The female’s satiny voice carried in the cramped room low, but audible.

“You’ve been fooling us around, ol’chap,” she started, her back to Nick’s cell. “Still silent on the headquarters,” she demanded, her hands going to her uniform’s top.

Nimble fingers unbuttoned it, and the other man’s eyes fell on what she might be baring, his eyes bulging as a noise came from his throat. It did sound like torture after all.

The jailor cupped her round breasts and offered it to the prisoner. He seemed too far gone to resist and merely lowered his hairless head and gobbled them with a moan. A thirsty mouth ate at them as she yanked his jeans down to make a fully erect member pop out. Not so big as Nick’s, it still commanded respect. Her smart hand drove under the rounded belly to close around it, and the staff hardened even more.

“The location, Jack.” She insisted.

“I don’t know.” He rumbled in between suckles.

At that, the woman knelt before Jack as he watched her with pain on his overgrown bearded face. She gave a swift lick on his red shiny glans, which made him throw his head back. With only a lick? Thought Nick. The guy must be desperate.

“Yes, you do.” Her head lifted to him. “After a week of this, we are sure you do.”

A week? He had endured these sessions for a week? His dick must be raw by now, which explained his overtly intense reaction to her touch.

Her hand fished something in her pocket and pulled out a cock ring. “Oh, no! Don’t do this, Shannon, please.” Jack begged. “I got the blue-balls last time, I—”

“You have the means to fix it, Jack.” She drawled, wrapping the rubber band around his prick and balls. This tight, not even a pro blow-job would milk him.

Jack’s skin on his neck went flag-red, features contorted, he must be trying to contain the scream bubbling in his throat. Bellow the hairy fat midriff, the protruding organ reacted as expected.

And then the torture started in earnest.

Her crimson lips closed around the erect glans as poor Jack buckled his oversized hips forward. His scowl crumpled further when his head fell back. Shannon cupped his balls, her red nails forming a crown over them. She squeezed, and Jack’s hips jerked forward to fuck her mouth further.

She yanked her head back, making Jack’s furiously erect phallus fall from her lips. “C’mon, Jack, let’s be a team here.” The jailor coaxed.

The tortured man panted in quick puffs, sweat slid down his temple in rivulets, his eyes fixed on his helpless member. With a smug smile, she wrapped a hand around the heavily veined stem, the thumb teasing the slit on the glans. In the dimness, it shone with the pre-cum her finger smeared over the harshly red tip.

“I never knew where they met.” Jack mumbled, his neck’s muscles tensing with the effort to endure the horrible pleasure.

Swift, her head moved and her mouth engulfed his painfully stretched mast again. Jack’s scream was something from another world. Pain and agony and need all wrapped in one ragged noise.

“Fuck, Shannon!” he rasped. “The cum is all pooled to release. Let it out!” he begged She freed her mouth from his member to slide her tongue under the staff, with special attention to the part where the glans met the prepuce skin. “As soon as you spill the beans.” The taunt came seconds before her lips closed on one ball. Jack’s jaw ticked. The round belly trembled like jelly with his pants.

Nick hissed inward, sympathising with the other inmate. The new wave of sensation must be burning the man up to ashes. The display on the other cell acted like a porn film for him, his dick up and ready as he watched the tableau with unblinking attention.

“I told you.” The other prisoner heaved. “I don’t—”

But the woman was opening the pocket on her thigh to come up with a back-orifice vibrator. These people were not playing in the park here, Nick thought. The bombarding of stimulation would drive anyone crazy.

Her tongue moistened the newly arrived toy, put it on, and her hand rounded to the back of Jack’s overweight butt, forcing it in his ass. Then she stood up to enjoy the view.

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