How to Escape From Jail
Bdsm Story

How to Escape From Jail

by Citizenhotel 17 min read 4.2 (8,000 views)
bondage humiliation public humiliation damsel in distress bound and gagged gagged and bound abduction prison
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The following story is a loosely edited version of a roleplay session between this author and the ever-wonderful ContinentalCo. It contains a great deal of bondage and humiliation; reader discretion is advised.

1.

Lucas Kane sat quietly in his cell, waiting. The dark-haired, scruffily handsome convict had books, and porn mags, and even a dodgy old TV inside a wire cage, but none of it interested him. He was waiting for her to walk by.

Right now the pretty young guard was the one thing he cared about. Well, that and getting out of this place. But there was no point thinking about that. Unless...

He rubbed the stubble on his cheeks - no razors in here, of course; just an old electric shaver that barely worked - and thought about all the things he'd like to do with that little minx. If only they had met under better circumstances. Like a kidnapping.

On the outside, kidnapping pretty young women had been Lucas's thing. He loved everything about it: loved the planning, and the hunt, and the sudden thrilling grab, and then the tight bondage afterwards. He loved having them in his power and seeing their fear and humiliation. He loved tightening their bonds and watching them squirm helplessly. And he loved tight silencing gags best of all.

He sighed. Better get used to it, he thought. No more kidnapping for you. Kidnapping is what got you thrown in this place.

But wait! Lucas's face lit up, and his gloomy thoughts vanished. The sound of clacking heels approached and finally a girl entered Lucas's field of vision - and a vision was precisely what she was. He loved her uniform. Her fine toned legs shone in sleek pantyhose; a short skirt barely reached to the middle of her shapely thighs. A tiny blue shirt hugged the curves of her torso, while long brown hair cascaded down her back. Lucas was pretty sure she was Spanish, on account of the accent and her tanned good looks.

Andrea, for that was the guard's name, paused for a moment next to Lucas's cell, a mark of distinction which frustrated the rest of the prisoners. "Come over, sweetie! Let's lay down on my bed for a little while!" yelled one black inmate, while others offered cheers and kisses to the pretty young guard.

Andrea ignored all this, and looked at Lucas with disgust and antipathy. She had often caught him leering at her, and knew what he was in prison for. He was handsome, for sure, and she had a thing for older guys. But Andrea hated men who took advantage of women, kidnapping them and holding them prisoner against their will. She hated that kind of man. And she hated Lucas too...

Lucas grinned, imagining scenarios with the pretty guard at his mercy. In his daydreams, she was eager and compliant, happy to enjoy his charms and submit to his whims. The truth, of course, was quite the opposite: she could barely stand to look at him.

Which just made her more of a challenge.

"Andrea," he said, smiling roguishly, "I'm so sorry about these scoundrels. They are so damnably rude. Dennis, apologise now!"

"Sorry ma'am," said the black inmate sheepishly. He was a surprisingly good actor, well worth the bribe Lucas slipped him earlier today. Certainly a better actor than bank robber.

"I feel like B Wing has let you down," Lucas added. "Will you let me make it up to you? I give a great massage..."

Andrea crossed her arms defensively and frowned at Lucas with her nose wrinkled in disgust. "No thanks. I know why you're here and I'd never let you touch me. You're nothing more than a disgusting pervert. So go back to sleep, weirdo," she answered mockingly.

The rest of the inmates cheered, enjoying Andrea's brave words. She rolled her eyes uncomfortably. The men were always joking and trying to flirt with her, and she was tired of it.

Lucas watched her long shapely legs as she walked elegantly away down the corridor, swinging her slim but curvy waist. Andrea looked back at him over her shoulder as she left. It seemed like she wanted to check if she still had Lucas's attention...

2.

Lucas was delighted to see how easily he could provoke the Spanish beauty. He knew she thought about him too, knew she found him fascinating. Under other circumstances, she would willingly slip out of that tiny little skirt, undo that adorable little tie, show him more of that stunning tanned body. But he was going to have to work for his pleasures today.

"Andrea!" he called as she walked away. "Andrea, it's Dennis! He's choking!"

On cue, Dennis went into an amazingly accurate impression of a person with a piece of bread stuck in their throat. Bravo, Dennis! The guy deserved an Oscar.

Now just come closer, little fish, thought Lucas. To get to Dennis's cell she would have to pass close by his own... and Andrea had no idea how nimble his hands could be...

Dennis really looked like he was choking. Alarmed, Andrea trotted briskly towards his cell, or as briskly as her high heels would allow. But a strong arm appeared suddenly between the bars of Lucas's cell and caught her, wrapping tightly around her waist. "Not so fast, sweetie," Lucas whispered from the other side of the bars. "Aren't you going to give me a kiss?"

"Get off, you pervert!" Andrea tried to break free of his grip but he was too strong. As one of Lucas's arms held her effortlessly, arms pinned to her sides, the other took away her pistol and truncheon. "Give me back my gun! I hate you!"

Dennis was no longer choking. Instead, he was watching the show with delight. "That's it, gorgeous!" he cheered Andrea between giggles. "Show this prick who's in charge!"

With her gun and truncheon safely in his possession and her slim body trapped against the bars of the cell, Lucas knew that Andrea was almost in his power. Squirming desperately against his muscular arms, she could not free herself from his grip. But she could still alert the other guards, and it was essential to silence her cries for help.

"Be a good girl and keep quiet, won't you darling?" he chuckled as he clamped a hand over her mouth, enjoying the feel of her quivering lips as she tried to cry out. But her plaintive calls for rescue were muffled and she was pleasingly silenced, reduced to nothing more than sexy, writhing eye candy. The more she wriggled, the more turned on he became, as he groped her young body through the tight shirt.

"That's it, sweetheart," he added cruelly. "Silent and obedient, just the way I like my girls. But where are my manners? I should invite you inside for a little chat, shouldn't I?"

3.

Andrea let out a muffled shriek into Lucas's hand when she heard his words. "Nnnnlmmph!! Ght ahff!!" Eyes wide with fear, she looked desperately to the rest of the inmates, maybe seeking a saviour. But all she could see was a crowd of rude caged men, leering at her and chuckling viciously.

"You're a lucky bastard, Lucas! She's a lioness, though. What are you gonna do now?" asked an old inmate with a bushy beard and a scar on his cheek.

Andrea wriggled and twisted her body as she felt the inmate groping her body and breathing heavily with desire.

"There's only one thing to do with a lioness," Lucas replied. "Muzzle her and put her in a cage."

Like a spider reeling in its prey, Lucas now began to drag the writhing beauty towards the door of his cell. This wasn't easy, because the bars got in the way and he had to keep changing hands. But he was an experienced wrangler of spirited young women, and managed to get Andrea to the door without allowing her to make a sound or slip out of his grasp.

"Oh, that's very skilfully done," said Ray, the older inmate, and several of the others broke into respectful applause. Lucas smiled and nodded in acknowledgment, pleased with his work.

"Please do come inside, young lady," he said mockingly to poor wide-eyed Andrea, who realised she was in big trouble now. "I seem to have misplaced my key, but you don't mind if I borrow yours, do you?"

His lewd and nimble fingers moved across Andrea's body, quickly finding her keys... but also finding time to tweak her nipples through the thin material of her shirt.

"This way, my dear," he whispered in her ear, as he unlocked the cell door and dragged her inwards.

"Grrrlmmmph!"

Andrea planted her feet on the floor of the corridor, pulling against her captor's grip and refusing to come into his cell. The inmates burst into laughter.

"She's putting up a good fight, Lucas!" said Dennis. "It seems you will have to tame her!"

"Lhft ghfm!" she moaned into his hand, glaring and twisting her body to escape from the strong fingers pinching her nipple.

"Check out her legs!" said Ray. "You can see her muscles tightening! She's hot!"

"Hffff!!" she huffed, rolling her eyes in frustration and embarrassment. Fucking perverts!

"She's a feisty one, isn't she?" Lucas laughed. His refusal to take the situation seriously made Andrea even more frustrated and annoyed. "And yes, a hot little thing. Once I've tamed her, she'll warm my bed nicely."

Effortlessly keeping an iron grip on his squirming prisoner, he suddenly tickled her lightly under one arm. Andrea giggled involuntarily into his hand, and forgot to resist for just a moment... which was long enough for Lucas to whisk her inside the cell and slam the door.

4.

Lucas forced her down to the floor and knelt on top of her, his powerful legs either side of her wriggling body keeping her arms helplessly pinned to her sides. He could now keep her silent with one hand over her mouth, and use the other hand to torment and humiliate her in whatever way he liked. He idly started undoing her cute little necktie.

"You know what's going to happen now, don't you?" he smiled. "I'm going to truss you up. Really tightly and securely. Ready to be nicely bound and gagged, my lovely little damsel in distress?"

Andrea's eyes opened wide when she heard his words. Now she was half scared and half furious. She thrashed and kicked, trying to push him away, but it was useless: he was older and far stronger. Once her tie had been removed, he undid the buttons of her shirt and opened it, exposing her breasts.

"Look at that!" Lucas exclaimed while pinching a nipple. "Nice tits!"

"Don't touch me! Bastard!" Andrea's face turned red with embarrassment and outrage.

"Aw, did that hurt?" he laughed, tweaking her other nipple for good measure. "Poor baby."

Her firm young body felt wonderful, squirming and wriggling helplessly beneath him, and he took a moment to enjoy her struggles... until she noticed, squeaked in outrage, and froze.

"Is the show over? What a shame, sweet tits, I was enjoying that! Oh well, I suppose we'd better get on with securing you."

Lucas tied a fat knot in the middle of Andrea's necktie with one hand, while keeping the other firmly clamped over her lips - "You had no idea I was so clever with my hands, did you?!" he boasted - then he shoved the knot deep into her mouth.

"Let's get you dressed up all smart, sweetheart! You've got to remember to put your tie on."

He lifted her head so he could reach behind it and tie the necktie tightly at the nape of her neck. She was thoroughly gagged, and realised she could no longer call for help. She had been dreading the humiliating moment when one of her male colleagues found her in this demeaning position, but now she wished someone would come and rescue her.

"Ullmmmmph!"

Andrea chewed on her gag and moaned into it, writhing and twisting, desperately trying to escape from Lucas's clutches. She felt so humiliated and vulnerable that she couldn't stop her face from going bright red. She was so embarrassed, in fact, that she couldn't even look him in the eye; instead she gazed up at the ceiling in frustration.

Mumbling and squirming ineffectively was all she could do, and the worst part was that she knew he was enjoying the show. She could hear his friends yelling and clapping from their cells, too. Lucas laughed and smiled back, enjoying the attention.

"We've got her well muzzled now, lads! She won't be nagging us any more. But she needs her hands bound too. Over you go, darling."

Lucas rolled Andrea on to her belly, giving her cute arse a good slap and grope, then wrenched her hands behind her back. He had prepared some torn bedsheets to use as binding materials, and he used a strip to tie her wrists extremely tightly together, straining with all his might to cinch the material as securely as possible.

"How's that, princess?" he laughed again, giving her bum another squeeze. "Nice and comfortable?"

5.

"Fhhk yhfff bhfthrdh!" Andrea tried to let Lucas know how she felt about the situation, but the gag was too effective to get out more than a muffled mewl. She felt the restraints tightening around her wrists, his rough manly hands grasping and slapping her butt. How embarrassing! What an awful, evil man!

As she kicked and struggled fiercely trying to escape from his firm grip, she again heard the rest of the inmates cheering and whistling from their cells. They were peering through the bars, enjoying the show.

"Give that fine ass another smack, man!" she heard a cracked voice shouting. "She's begging for it!"

Even face down, she could almost feel Lucas's eyes running over her body, from head to toe. Fucking pervert! He probably would-

SMACK! SMACK! SMACK! Sure enough, the blows landed loudly on her bum. She could feel the impact of his hand through her skirt.

"Aww, are you trying to say something, sweetheart? I can't understand you! It must be something to do with that nice tight gag in your mouth. What's that, angel, you want to be bound more securely?"

Lucas chuckled and stroked Andrea's blushing cheek as she indignantly tried to make herself understood, but the cloth filling her mouth muffled her complaints very effectively. "It must be incredibly humiliating," he teased her, "being silenced, groped and displayed in front of the prisoners you're supposed to be in charge of.

"Don't worry, baby," he added, smiling, "I've got plenty of torn bedsheets so you're going to be trussed up nice and tight, just the way you like it. You naughty little ropeslut!"

He pulled off her tiny skirt and panties, enjoying the cheers when the other inmates saw the pretty guard's naked bum, then started winding cloth around her waist. He knotted it tightly, then threaded one end down between her legs so it slipped inside her pussy, yanked it up at the front, and tied it off firmly.

"That'll give you something to enjoy while I finish roping you up, darling," he laughed.

"Ullmph!!"

Andrea yelped in shock when she felt the cloth pressing against her intimate parts. Her eyes opened wide as she glared at her tormentor. He was holding another piece of bedsheet; realising what he planned to do with it, she kicked and squirmed to escape from his strong, skilled hands.

"Ghf auft hf hirrr!!" she mewled. Having her butt and legs on display for all those men made her feel incredibly embarrassed. She aimed a kick at Lucas's jaw, trying to hit it with her bare feet. She was desperate!

"Whoa! Look at these fighting skills!" he laughed. "See that, everyone? She's got all the moves."

Still chuckling, Lucas caught Andrea's shapely leg by the ankle and held it in a firm grip, grabbing her other leg and bringing them together.

"You could hurt yourself, darling! Much better to get these safely bound."

He used the torn bedsheet to tie her ankles tightly together... then, just to be sure, he quickly bound her calves, knees and thighs as well. Andrea's legs were now helplessly pinned together and she was running out of options.

6.

"Ullmmmph!" Andrea moaned into her gag, desperately twisting and kicking her shapely legs. It was useless: the bonds were simply too tight to escape. The inmate had done a great job, proving himself expert at tying knots. She was totally helpless... and just for a moment she wished her boyfriend was this good with ropes. Before remembering where she was and telling herself off for having such unhelpful thoughts. Focus, Andrea!

The inmates whistled and cheered wildly as Andrea writhed against the restraints. Her captor too was enjoying the scene, watching her squirm around and occasionally groping her exposed, trussed-up body. Caressing her legs from thigh to ankle, or smacking her butt when she shook it while struggling.

Andrea rolled her eyes and kept fighting. Her face was bright red with humiliation. Another unhelpful thought popped into her head: Lucas really was kind of handsome. Older, stronger... he was exactly the kind of man she would love to submit to. But not here, of course. Not now. In fact, she was furious with him, and determined not to make things easy for him. He was a criminal, after all!

Lucas, meanwhile, was enjoying himself. As he had known he would: capturing a pretty young woman and tying her up as tightly as possible was his favourite way to spend an idle afternoon. What he did not expect was for her to enjoy it too. But based on the moans coming through her gag, the deep blush on her lovely face, and the way her hips were grinding against the crotch rope, she was definitely starting to get into the spirit of things.

"Hey lads!" he laughed. "She's getting turned on! I think she's into bondage!"

As the inmates laughed and cheered Andrea's eyes widened in outrage and her face got even redder than before. Unfortunately she was in no position to deny the allegation.

"Well, it's your lucky day, sweetheart. Because I intend to give you a thorough demonstration of the arts of strict bondage, and I won't charge you a penny! Those arms of yours, now... they're not anywhere near helpless enough, are they? Allow me to help."

Lucas grabbed another piece of torn bedsheet and wrestled Andrea's elbows together until they touched, then bound them tightly together. It was incredibly uncomfortable and pushed her tits into a position of humiliating prominence.

"Nice rack!" he added, smiling with satisfaction.

Andrea gave Lucas a furious look, her face burning with embarrassment. I can't give up, she thought to herself, these men are criminals. I'm better than them! She kept writhing and struggling against her restraints, which felt tighter and more inescapable than ever. Besides the cloth bindings, Lucas's rough manly hands were keeping her firmly in place.

"Ght yhr hanff hff meph!!" she complained, but he just laughed, and ran his hand across her prominent chest. She suddenly felt his fingers rubbing her left nipple.

"Oh girlie, these nipples feel hard! Did you hear that, boys? She's getting excited!" The inmates cheered again, trying to get a glimpse of the show.

"Get her out of her clothes, brother!" yelled Dennis. "Make the lady fresh and comfortable!"

"Grrlmmph! Fht uhp!" Andrea growled at him from her helpless position.

"Yes, good idea, Dennis," said Lucas, ignoring Andrea's muffled objections. "Our little captive is getting hot. Let's help her slip out of these uncomfortable clothes."

But first he took a moment to enjoy the sight in front of him. Her pretty, squirming body was tightly and thoroughly bound with torn bedsheets: wrists and elbows tied behind her back, ankles, knees and thighs tied together, and a cruel crotch rope snaked down between her legs to cause intolerable humiliating pleasure.

And what about her outfit? She had lost her skirt, panties and pantyhose, didn't seem to have remembered to wear a bra today, and for some reason was wearing her necktie between her teeth as an effectively silencing cleave gag. But she still had that unbuttoned blue shirt around her arms and the high heels on her feet.

"You can keep the heels," Lucas smiled, "but lose the shirt, sweetheart."

Andrea was in no position to comply, so he produced a knife he had been hiding in his cell - "Don't worry, bimbo! I'm not going to hurt you!" he laughed - and carefully cut the shirt off her body, taking the opportunity to cop another feel of her prominent nipples.

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