David and Becky - Foolish Choices Ch. 05

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The new prison guard and a double strapping.
4.5k words
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Part 5 of the 22 part series

Updated 06/11/2023
Created 04/30/2022
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OllyT
OllyT
320 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 5

Day 228 -- Tuesday 15th March 2016

It was forty days since I'd received a punishment caning from Madam Popescu, and when she turned up in the afternoon dressed immaculately, I knew the reason for her visit. She had such an air of superiority about her; even though she was about three inches shorter than me, I always felt she was taller than me. It seemed to defy physics as I always felt like my head was positioned so I was looking up to her and she was looking down at me. She must have got into my head in such a way that I actually believed I was smaller than her in every way. My penis stood solid and erect like an immovable metal rod.

"When was the last time you had an involuntary ejaculation, Mr Emerson?" she asked, so seductively.

"Forty days ago, Madam Popescu, right after you caned me."

"And nothing since? How dreadful for you," she replied, showing mock concern. "Would you like one of the spa girls to come and help you relieve the awful tension you must be feeling?"

Despite seeing no humour in what she'd said, I couldn't help but smile at her little joke. "I would absolutely love you to do that, Madam Popescu, but somehow I think it unlikely. You are an excellent disciplinarian, and providing someone to give sexual relief to one of your prisoners who is here for punishment would go against all that you stand for."

She smiled at me. "Eloquently put, Mr Emerson. You have learned much while you have been here. I hope the discipline to which you have been subjected to will stand you in good stead when you leave us."

Although I nodded my head to agree with her, I had no idea how such discipline had any relevance to normal everyday life.

"It will be with much sadness when the time comes for you to leave us. Today is March 15th which means your nine month sentence has less than fifty days remaining. Doesn't time fly when you are having fun?"

"Yes, Madam Popescu, it does, but when you're not having fun, time drags, and it feels like I've been here for years."

"Good, it shows prison has the desired effect. Hopefully the final days of your sentence will be equally unenjoyable for you."

She crossed the floor and stood close to me, her hand reaching out to touch my engorged penis. I moaned with pleasure at the feel of her delicate hand. It was the first time she had touched me in this way and I felt honoured as well as excited.

"Forty days is a long time to avoid pleasuring yourself when you are so desperate, do you ever wonder if a nice satisfying, self massage to relieve your agonising frustration would be worth a caning?"

"It has crossed my mind, Madam Popescu, but, for a moment of stress relieving pleasure, I'm not sure a caning in front of an audience of sadistic ladies would be worth the pain and humiliation, not to mention the days of hard labour that would follow."

"You're probably right. But the thought of not getting to cane you again does fill me with disappointment."

She walked around behind me and I was aware of her crouching down.

"Perfect. The marks on your bottom from my caning have completely gone. After feeling the intensity of a forty stroke caning from me, the strappings given by my guards will have lost their edge."

"On the contrary, Madam Popescu, I think the strap being delivered by your guards will still be very painful; the pain is so much different to the cane, not as severe, but very painful in a different way."

"Are you getting to enjoy the pain?"

"Er, I don't know what you mean, Madam Popescu."

"You clearly relished the caning I gave you, certainly towards the final few strokes," she said.

"I was in another world towards the end, Madam Popescu."

"A world you would perhaps like to visit again?"

"I wouldn't choose to go there again, but if I did, maybe that strange feeling might come back."

"You may notice, Madam Gabriela has a different sort of strap with her today. I wouldn't actually call it a paddle, it is more like a short, but very effective whip which I am testing for its effectiveness in disciplining my prisoners. If I receive good feedback, it may become my preferred instrument of punishment for my guards to use. For simplicity, I think I will call it a paddle whip."

She indicated Gabriela to step forward.

"Show our prisoner," she said to her.

It looked more like a ruler than a whip and was about eighteen inches long and an inch wide along its full length. It was a little more than a quarter of an inch thick and made of what looked to be hard plastic. It looked quite heavy with only slight bendiness in its length when Gabriela flexed it between her hands. It looked painful.

"As I have declared your bottom fit for corporal punishment, Madam Gabriela will give you six strokes before I leave so you can feel the pain it can give. I want you to take this, prisoner, without a single sound coming from your mouth."

What had I done to deserve this? I'd spoken in a thoroughly respectful manner to her, and my reward was a beating with this horror paddle ... six strokes. Gabriela ordered me onto the bed with the pillow beneath me to raise my buttocks. I quickly complied and lay awaiting the beating to begin.

Gabriela quickly went to work slashing the first stroke as hard as she could across my bare bottom. I was adept at holding in my cries of pain, but this was a step up from the straps I was used to. The pain was heavier and a feeling of burning heat ripped across my bottom causing me to wince, but only minimal sound came from my mouth. As each stroke smacked hard across my exposed buttocks, I gripped the end of my mattress harder and harder. The blows came thick and fast, each following quickly from the last, excellently delivered with precision and in such fluid movement. The pain was a whole lot different than the straps or even the cane; much worse than the former, but not as intense as the latter, but the main difference was, the pain didn't recede anywhere near as quickly as those others. Instead, the pain increased as the strokes landed. By the time the punishment had finished, I was straining to keep from shouting out from the intense pain Gabriela had inflicted on me. She calmly went and stood beside the cell door.

"Thank you, Madam Gabriela, well done," Madam Popescu said, looking down at me with a gleam in her eyes. "I see the marks it leaves are nice and red spread evenly over your bottom rather than weals which take longer to disappear. Get off the bed and stand up, I want to check something else."

I did as she ordered and stood beside my bed facing her. The hot, stinging throb of my buttocks was sending waves of ecstasy through my body which caused my penis to stand upright, rock hard and frustrated, pulsating with unquenched lust.

"I think you might have enjoyed Madam Gabriela's new toy, Mr Emerson. If you wish, I could arrange for all your guards to be issued with them."

The pleasurable feeling was increasing as she spoke and there was nothing I could do to hold back the inevitable as a blob of sperm spurted from my penis just avoiding Madam Popescu. I could do nothing to stop it, and in panic I put my hands behind my head as another blob pumped out in front of me. Madam Popescu watched with amusement and delight as the third pulse of my penis issued a narrow stream of white fluid that poured out falling directly to the floor. It seemed never ending as the three of us in the cell said nothing; the involuntary action continued as if my penis had a mind of its own. A small pool of sperm was forming between my feet, the contents of what had built up in my testicles for the last forty days. I had no pleasure whatsoever, not even a hint of an orgasm, it was a waste of what could have been several seconds of unbelievable pleasure. It was an orgasm lost to the hell that was this prison.

When the ejaculation was complete, Madam Popescu gave me a little smile. "That must have been diabolically frustrating for you, Mr Emerson. You did well to refrain from touching it. Clean it up after we leave."

They left me alone in the cell with my bottom still throbbing from the new whip or stick or paddle whip, whatever it was called, and an unsatisfied feeling of emptiness in my penis and testicles. But, I wondered if what Madam Popescu had implied was correct; to have had an involuntary ejaculation for the second time after being beaten, was I coming to enjoy being punished?

Day 233 -- Sunday 20th March 2016

Mid afternoon, just five days after Madam Popescu gave my bottom the all clear for further beatings, I heard the familiar sound of footsteps arriving outside my cell. I immediately jumped off my bed and knelt on the floor before the three bangs came on the metal door. As my visitor entered, I was ordered to stand, and I saw it was Madam Elena, my penis quickly grew in anticipation of what may happen next.

"It's been a while," she said. "Oh, you are free to talk, by the way."

"It must be almost two months, Madam Elena," I said.

"Have you missed me?"

As she was my only contact with Cassie from the casino back home, I had missed Elena mainly for that reason. As she was in a particularly friendly mood today, I was hoping she had a positive message to give me from the girl I was exchanging emails with. "Of course, Madam Elena."

"You haven't got very long left," she said, almost sadly.

Rather than sharing her sadness, I felt a little wave of joy ripple through me. "I've just got to get through to the end of next month, so, about six weeks."

"I have some news," she said, a little sheepishly.

"Is it good or bad?" Such was my paranoia, rather than thinking it was an email from Cassie, I suddenly decided it was going to be bad news instead.

"It's actually quite good, although a tinge of not so good as well."

"Madam Elena, please tell me." Now I was feeling very hopeful, but what was the bit that wasn't so good?

"This is my last day at Casavana."

I was shocked to hear her news. "Why are you leaving?" This was someone who had reported me for a judicial caning for doing nothing wrong, and had forced me to pleasure her orally with no relief for myself on a couple of occasions. And yet, I was saddened I wouldn't get to see her again.

"Madam Popescu is moving me to one her spas; she has promoted me to manager. Having successfully completed my training to become a dominatrix in addition to my academic qualifications, she now sees me as capable of a managerial position in the leisure side of her businesses. I think she was really pleased with what I did to you." She smiled apologetically, but so sexily. "Sorry."

What she'd done to me still annoyed me intensely, but I tried to ignore it by keeping the conversation about her move going. I had more important worries about my contact with Cassie. "Will your role be just administrative or ..."

"This is the good news, David. I will no longer have to put up with the bastard men slobbering over me and sticking their fat cocks in my mouth and pussy."

"That's great news, Madam Elena."

"But, the slightly bad part is I will not get to see you again before you go home." She pouted.

"I'm truly pleased for you, Madam Elena. I know I didn't get to see you that often, but I enjoyed your company when you were with me. And you have been so helpful sending and receiving messages from Cassie, back home. I will miss you not being here."

"You've been so good, and done so much for me that I haven't deserved. You patiently listened to my rants about the pigs who visited me in the spa, and comforted me when I kept going on about them. I'll never forget those fantastic times you gave me oral pleasure; you really do have a gift. And I haven't forgotten that time I was a real bitch to you when I reported you for masturbating when you were totally innocent. You got forty strokes of the cane and three days hard labour because of me. That was so unjust, but I needed to do that as the final part of my qualification. I know it hasn't helped you at all, but at least some good came of it for me, if you can see that as a tiny bit of consolation for you. I've tried to partially pay you back for keeping you in touch with Cassie, but I would really love to do something nice to fully pay you back for all those things ... so ..."

She unbuttoned her fur coat and let it drop to ground. She was completely naked! Slowly and seductively, she stepped towards me, my penis was throbbing with excitement at what I hoped I was about to get. I expected her to stand still with space between us but she didn't. She moved her body right up to mine and wrapped her arms around me, hugging our naked bodies together. My penis was squashed between us, upright and pressing against her naked belly. The feeling was out of this world, to feel the bare flesh of a female body pressed up against me in such an intimate way.

She kissed my neck, and then my chin before reaching my mouth with her soft, delicate lips. I put my hands around her waist, unable to resist her advances, and accepted her mouth on mine. She gave me such sexy kisses all over my mouth, selecting my bottom lip to suck on, then my top lip, licking between both my lips, pecking me with deliberate arousing softness that was driving me wild with lust. Then, she pulled away slightly and looked into my eyes.

"I just wish I could have rewarded you with more than this, David, but you know the rules, as evil as they are. This is the best I can do for you; I hope it's something you can remember me by."

She then stepped back and picked up her coat as two others entered my cell. It was Madam Popescu and a guard I'd never seen before.

I was shocked, but Elena wasn't.

"I just wanted to say goodbye to you properly, David," she said with a genuine smile. She nodded to Madam Popescu before leaving the cell.

"It is rare that I allow such shows of affection in my prison, Mr Emerson, but Madam Elena did share with me how you helped her over the few months you have been with us. I thought it only fair she should be allowed to show you some appreciation for that kindness."

My mind was a whirl; what had just happened? Had Elena just left Casavana, thinking she was rewarding me by rubbing her naked body right up against me, knowing I would get no relief? That was the cruellest, so called reward, anyone could have given to someone who had tried to do the best for that person. I couldn't believe she'd done that to me. She'd even mentioned Cassie, but there was no mention of a reply from the email I'd got her to send. Was my distant relationship with Cassie turning out to be a massive, but unintentional tease, promising so much and delivering only frustration and heartache?

"I have great hopes for Madam Elena," Madam Popescu said, proudly. "I see her as being an ideal advisor to me, someone who can be more than an assistant, someone I would call my number two. As you already know, she studied psychology at Keara University and is brilliant at getting inside the minds of people. Her sadistic nature does not demonstrate itself in giving physical pain, she has the knack, gained from her education, of inducing mental anguish in her victims, as you have experienced. I am sending her out to work at my other establishments for a few months to learn all about how to deal with staff, as well as men, either to give pleasure or pain, in all its forms. When she has gained more experience in various aspects of my leisure activities, she will return as my second in charge, and Casavana will be a place to be feared even within the fetish scene. Of course, in her absence, I have brought in someone who will work in the video surveillance room, checking the tapes daily for any infractions of the rules. Therefore, I would like to introduce, Madam Justyna, the newest recruit to my excellent team. As well as working in surveillance, she has also expressed a wish to make up the rest of her time as a prison guard."

I looked at the girl who stood beside Madam Popescu. She was observing me while glancing occasionally at my gradually wilting penis with slight amusement on her face.

"I am very pleased to have found such a beautiful young lady as Justyna with a sadistic nature that you will become acquainted with. At twenty one years of age, she is the youngest any guard can be under Siskovian law, but she is as much a sadist as any other guard here. Private prisons all over the country seem to attract many applicants from young females, and with many providing similar services to mine, competition to recruit the very best is strong. To make sure I never miss out on ideal candidates, I advertise frequently, and those who apply are subjected to a long, arduous process of assessments before even reaching a very tough and searching interview. I am particularly keen on those ladies who have leaned towards violence in their past, even those who have convictions for such offences. I very rarely take on new staff as I only accept the very, very best."

She turned to look at her new recruit and smiled warmly at her. Madam Popescu looked so beautiful no matter whether she had an evil glint in her eyes, or she wanted to show affection. Justyna smiled back at her, and I could see a confidence rise up inside her, no doubt gained from the show of support from the prison boss.

"Those rare applicants who are successful are free to exercise their violent natures within my prison, fully protected by the law. Many have felt the harshness of the strap on their flesh through their own experience within the prison system. They know the pain it causes, which is why they are so keen to administer it themselves to satisfy their sadistic tendencies. By also insisting only those who are stunningly attractive, like Justyna and the other guards you see around this establishment, it adds to the sexual frustration for prisoners, all of which are starved of any sexual release. And how humiliating to be treated so badly by such young attractive ladies. I think you will agree, all my selections are perfect for the roles they fill."

I had already been told some of the staff had a history of violence, which made my position here all the more harsher. Those guards deserved to be in my position more than I did, and yet, here I was, subjected to painful strappings from them whenever they wanted.

Justyna was a very pretty girl of average height, with an athletic move about her. Her light brown hair was long and straight, halfway down her back. Her eyes were dark brown and made to look even darker with eye shadow and sharp eyebrows. As pretty as she looked, I could see a glint of cruelty in her face, even when she smiled, she showed little warmth. She wore the standard uniform of tight T-shirt which emphasised her shapely breasts, and short leather skirt. Her bare legs were long and slim, and on her feet, she wore brown leather ankle boots. She was utterly stunning, and I was both fearful and excited that she was to be one of the guards for the last six weeks of my sentence.

"I warn you, Mr Emerson, not to underestimate Madam Justyna. She may be young, and have such innocent looks, but I advise you to treat her with the same respect you treat any guard. Despite her slim figure, I can assure you, her excellent technique at administering a strapping inflicts the most severe pain on her victims. And, I might add, she gets great joy out of doing so."

OllyT
OllyT
320 Followers
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