David and Becky - Casavana Prison Ch. 11

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Madam Izabela leaves me desperately frustrated.
2.8k words
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Part 11 of the 16 part series

Updated 06/11/2023
Created 01/26/2022
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OllyT
OllyT
319 Followers

This story is entirely fictional and is intended as a fantasy in the world of female domination and male submission. It involves tease and denial with the use of a male chastity device, cuckoldry and corporal punishment. No part of this story is written to suggest such lifestyles were realistic or believable. The characters, named and unnamed, are not based on any living or deceased persons. All locations, whether named or otherwise, in this story, including the nation of Siskovia Province, are also fictitious and any similarities to any that exist anywhere, are coincidental. If you are not interested in fiction in which males, whether willingly or forced, submit to dominant females, or find such subjects objectionable and in opposition to your own preferences, I would strongly suggest you exercise your right not to read any further.

Chapter 11

Day 67 -- Tuesday October 6th 2015 -- Part 2

When I reached my cell, my buttocks were on fire, like burning embers after the flames had died away, but my penis was still throbbing and I was desperate to relieve the pent up agony of sexual frustration. Gabriela said something to Tilly I didn't understand and both she and Tilly left the cell leaving Izabela and I alone.

"Your legs still tremble, was the caning that painful?" she asked. I knew she was mocking me.

"Yes, Madam Izabela."

She walked around behind me and her soft hand gave my buttocks a gentle slap and I flinched with the pain.

"Oh, you poor thing, it hurts to the lightest touch. Imagine being strapped right now on top of that," she enthused. "Or even caned again."

I uttered a whimper of fear.

"Don't worry, prisoner, I am teasing you, I won't beat you, it is against the rules anyway."

Her tickling fingers were making me flinch though, I couldn't stand their touch.

"I could report you for another caning in a few weeks, you don't have to do anything wrong. I could lie, and Madam Popescu would believe me." She gave a cruel chuckle. "But that wouldn't help with teaching good behaviour, would it? If canings were given for good behaviour, there would be no incentive to behave well."

She stood closely in front of me again and reached down to cup my balls, her dark eyes were fixed on mine. My hard penis bobbed. "You must be so desperate to come, especially with a beautiful sexy girl in the cell with you."

The sadistic bitch was trying to tempt me into making a mistake.

But then, her soft sexy voice turned harsh. "Lay down on the bed on your stomach with hands behind your back. It doesn't matter Madam Popescu says no strap for twenty days; if you struggle or disobey, I will beat you six times."

I did exactly as instructed, laying down on the lumpy mattress with my hands behind my back wondering what she was going to do to me.

"Don't be afraid, prisoner, I am not going to punish you, so relax, but if you move your hands from your back, I will cuff them ... then beat you." She knelt down on a cushion beside my bed.

"I was a nurse before working here, so I treat wounds after hard canings. I have an icepack for your poor swollen buttocks. You need it because they are deep red. Oh, it looks so nice."

I felt the ice pack being gently placed onto my buttocks and at first it felt painful and I moaned, which she ignored, but then the soothing effect kicked in.

"It feels good?" she asked.

"Oh, yes, Madam Izabela," I replied, genuinely grateful as the throbbing eased.

"I give permission for you to speak."

That was unexpected. I didn't know where to start. "My bottom feels like it's on fire, Madam Izabela," I said. "Is it bleeding?"

"Not running blood, but some blood is oozing from the wounds, but only like a graze. I will take a photo to show you."

I heard her fumbling in her bag followed by the click of a camera, then she showed me.

"Madam Popescu is an expert with the cane. I have seen her give over thirty canings, and every one perfect. As you see on your bottom, perfect horizontal lines one after another starting from the top of your buttocks down to the bottom, no misses. It is a work of art, but it must be so painful for you. I cannot imagine how painful it must be to feel the strokes as they land. I enjoy so much watching the caning and thinking how much it is hurting you. All the women here feel the same."

They were all unbelievable sadists.

"This ice will help the swelling go down faster, but you will be marked for many days." She laughed. "That's why Madam Popescu gives twenty days free of more caning. She always gives one free day for each stroke of the cane."

"What's the most strokes she can give?" I asked, fearing what her answer might be.

"Sixty strokes is the maximum by law. Ooh, imagine getting sixty strokes from her, it would be unbearable on your poor bottom, but it turns me on watching when she gives that many. Next time you get a caning, it goes up to forty, then sixty every time after."

"Is she the only one who gives canings?"

"Anyone can give a caning, even admin staff if Madam Popescu gives permission. But she is the best, so she gives punishments mostly to make prisoners suffer."

"What about you? Have you given canings?"

"Yes, I love it; you feel how hard I hit with my strap, I hit harder with the cane. I would like to practice on you." She laughed. "Would you like me to practice on you?"

"I don't enjoy being caned, Madam Izabela."

She took the ice pack off my buttocks and the numbness subsided, allowing the pain to return. "The swelling will go down soon."

She placed a smooth towel on my bottom and gently dried it. Then I heard her fumble in her bag, then the shaking of liquid in a bottle.

"Now, some antiseptic to put on the grazes."

I felt damp cotton wool being dabbed on my swollen buttocks and the stinging pain was like my bottom igniting with fire. I clenched my buttocks and winced, moaning slightly as the pain really kicked in.

She got up onto her feet and stood to my side. "You are done. Turn over onto your back, you may look at me."

My penis was rigid with sexual arousal and there was nowhere to hide my shame. Madam Izabela, with her almost black hair tied efficiently behind her head, her sharp, achingly pretty face and dark, seductive eyes, looked down at me. She wasn't that tall, but she was slim and her short black leather skirt showed off her bare, tanned legs. At some point she'd removed her short jacket to now reveal a tight white t-shirt showing her lovely breasts clearly outlined in the material. On her feet were the customary short leather boots. She looked so sexy, and she knew it.

She knelt down beside me again, her face was flushed and I could tell she was aroused. She reached down and wrapped her hand around my rock hard penis. I moaned with ecstasy.

"You are so aroused. Maybe you enjoy being caned after all?"

"No, Madam Izabela."

"It is so amusing. You do not like being caned. I love you being caned. And yet we both react the same. We are both sexually aroused." She let go of my penis.

"Madam Izabela, I'm like this because I haven't come for so long."

"Oh, poor boy," she mocked. "That turns me on more."

She looked back at my rigid penis, standing tall like a flagpole. Slowly, she lifted her T-shirt over her head to reveal her beautiful breasts that were just large enough to give a little bounce as the material pulled over them. Her nipples were erect, showing her arousal. My penis was almost pumping there and then. She dropped the shirt to the floor.

Then she tucked her fingers inside her skirt and lowered it to the floor before stepping out of it. Finally, she pulled down her panties to reveal her shaven pussy. I was almost drooling as I looked lustfully at her. She was stunningly gorgeous with the most perfect body anyone could dream of. I couldn't believe I was looking upon this sexual goddess standing before me wearing only ankle boots.

My mouth went to say something, but nothing came out.

"How long is it since you last enjoyed an orgasm, prisoner?" Her voice was so sweet and sensual as her words drifted seductively into my ears.

"I've not had an orgasm since I've been here," I lied. Was this the moment it was to be revealed to me they had me on film masturbating on my first day. I felt she suspected me of lying and I had a sudden urge to at least admit to the accident I had in the shower. "But I had an uncontrolled ejaculation about four weeks ago. I promise I didn't touch myself because I knew the rules. I had no choice but to let it trickle out."

"Don't worry, Madam Popescu said that might happen, as long as you didn't help it with your hand to make it feel better."

"No, I promise."

"Don't worry, eagle eyed admin staff check the video and would have seen you, so I am not here to punish you today," she said, sitting on the bed next to me. "But coming like that is not pleasurable, is it?"

"No, Madam Izabela. It was so frustrating and it left me just as aroused." I couldn't believe the strictest of my guards was speaking to me like this, actually sitting next to me naked on my bed. My penis throbbed.

"You poor thing," she spoke so affectionately.

I prayed she was going to, at least, give me hand relief. How I needed it.

She stood up and climbed onto my mattress placing each of her feet on either side of me facing towards my feet. Slowly, she lowered herself onto my chest. She edged herself back so her round pert buttocks were on my face. I couldn't believe it was happening. Her skin was so soft and delicate, so arousing, and I couldn't help but give her arsehole a kiss while her buttock cheeks brushed over my face. She edged further back until her wet pussy rested on my lips and nose, and she closed her thighs around my head. I took a deep breath, then she was on me. She pressed down firmly and ground herself into my face giving a moan of pleasure. I was smothered in a wonderful world of female sensation and scents.

"Use your tongue, prisoner," I heard her say from my intoxicating arousal.

I obeyed willingly. She leaned forward, her breasts resting on my stomach, I was aware that her mouth was so close to my penis. Rather than her mouth, it was Madam Izabela's hand that wrapped around my stiff member. I wanted her to stroke it, but she just held it while the fingers of her other hand cupped my swollen balls and gently massaged them. She groaned with pleasure as she rubbed her pussy on my tongue as I eagerly licked. I was desperate to give her as much pleasure as possible, even though I knew how much she'd enjoyed watching me being caned, and wanted to see me caned again.

She moved faster and faster, bearing down harder, tightening the grip of her thighs on my head, grinding her pussy over my nose and tongue. I couldn't breathe, but when I did, the scents and flavours of her delicious pussy filled my nostrils and my senses. I sucked and licked as hard as I could, suffocating in the heights of ecstasy as she used me for her satisfaction. Her gentle fingers touched my rock hard penis, but without enough pressure for my own enjoyment to mount. She was purposely doing just enough to keep my arousal at a maximum without getting too close to an orgasm.

Then she came, explosively. I heard her voice cry out with pleasure. I was smothered by the sweet flow of pleasure that thundered through her lower regions. I could almost feel her pleasure for myself as her pussy vibrated at the peak of her climax. She gave my aching penis one satisfying stroke with her hand as I felt shudders of ecstasy flow through her body, but that was all I got. As I felt her thighs relax around my head, she took her soft hand from my penis. Her scent had grown stronger, but all I could do was lay there helpless as she rubbed her soaking pussy over my face and mouth, smoothing herself all over me, over and over. I gasped for air, when I could, and kissed her again and again.

She knew how frustrated she had made me; she could so easily have given me the relief I was so desperate for. I actually believed at one point she was going to give it to me. But her sadism wasn't just focussed on inflicting pain, extreme tease and denial was also in her repertoire. It was the second time one of the guards had done this to me, but this time she had really led me to believe I would be given relief. Would I ever feel the exquisite delights of an orgasm again?

Finally, she climbed off me and stepped away from the bed. She picked up her panties and stepped into them, pulling them up. Then her skirt and T-shirt went on, before finally putting her jacket on. Fully dressed, she looked down at me with a wicked smile on her pretty face.

I moaned. I so wanted her.

"Did you enjoy that, prisoner?" she asked, at last.

"Yes, Madam Izabela." My voice was shaking. "It was pure heaven." It was actually pure heaven mixed with pure torture, but I wasn't going to say anything negative to her.

"I was so horny, but now I am satisfied thanks to you. I could easily have given you a wonderful orgasm with my hand, but I decided to make you suffer even more. But you have something to think about while you serve your last six and a half months of your sentence."

I was so aroused, I could feel a murmuring in my penis and balls, I was so close to coming, to spilling my load onto my stomach. I tried to hold it in but I was so frustrated, there was nothing I could, I had been driven to the very brink of orgasm by this evil, beautiful, cruel woman. I started to pump into the air with my hips to gain some friction, and when Madam Izabela realised what was about to happen, her face lit up with glee and she started laughing.

"Don't touch it," she ordered me, "or I will report you for a caning."

Semen dribbled from my cock, slowly at first, then with a spurt, then another spurt, then another, reaching my chest. I had to control myself like never before to prevent myself from wrapping my hand around my penis. The torture of that desperate need for the continued stroking friction of either a willing hand, mouth or vagina to bring ecstatic pleasure and release was unbearable. But the pent up frustration had no outlet, and as I spurted, my penis felt no such release, just that aching unfulfilled arousal, unsatisfied and empty.

It didn't help when Madam Izabela described what her hand would have felt like, how it would have given me the orgasm of my life. She taunted me and ridiculed me and laughed loudly at me as I writhed about, covering myself in weeks of semen. After I'd finished humiliating myself, she stood with her hands on her hips smiling down at me.

"Today could not have been better, I have had so much fun. But for you, it must be the worst day you have had here. And there are many more days like this to suffer. Maybe next time I will get all the ladies to watch you hump fresh air and spill your come with no pleasure."

She left me to clean myself up promising to return with my lunch, which she did about an hour later. On her return, she was back to her usual, distant, uncaring self, reminding me as she left that the first of two days of hard labour would begin tomorrow. There seemed no end to my torture.

Coming next in chapter 12: A couple of days in the company of Elena

OllyT
OllyT
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Robin_WildeRobin_Wildeabout 2 years ago

Wonderful! Just the sort of sadistic mindfuck I've been waiting for. I loved the sex-and-pain of the caning, but also the party atmosphere among the watchers. David's increasing arousal as the caning progresses reminds us that he is, after all, a masochist, and his humiliating hands-free orgasm after Izabella's tease is the perfect ending to a perfect day. Ah, and now two wonderful days with sweet, loving Elena. I can hardly wait. Speaking of, I'm glad of the three-day interval in the last couple of installments and hope you keep it up. Three days works very well for me: I devour the story as soon as you post your newest chapter, and the following day I reread it and usually look back over a few previous chapters. That gives me a day to muse and fantasize about what comes (or in David's case, doesn't come) next just in time to be nice and primed for the next installment. Cheers.

Al_AnonAl_Anonabout 2 years ago

Anonymous (uh, the one before 'Asssh')

Yes, they are sadistic cunts. That is kinda the whole point of this 35+ part series. The women are cruel, manipulative sadists & David is, at most, an innocent reluctant masochist. Some people get off on that. Others, apparently, prefer to blueball themselves in anticipation of some last minute revenge that'll probably never happen. To each their own.

AnonymousAnonymousabout 2 years ago

In reality, at this point he’d just be going through the motions. He wouldn’t be constantly erect and dripping. He’d now know the rules and just sleepwalk through them. Mentally, much like the reader, he’d expect nothing but the worst, be it news, comments, food, treatment, whatever. He’d be past the point of them being able to shock or disappoint him. And they’d get bored of it all too. But, keep on keeping on author. No horse too dead to beat.

AssshAssshabout 2 years ago

He must get more ass and pussy to eat!

AnonymousAnonymousabout 2 years ago

they are all a bunch of sadistic cunts when he gets out and sees Becky when he gets close enough time to punch her in the face and get rid of the whore as she is the cause of all his troubles

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