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Hailey S Punishment Day 01

Hailey S Punishment Day 01

by dfintner
19 min read
4.66 (36500 views)
adultfiction

PROLOGUE

It had been a rough year for 65-year old Bert Charrington. January had started with the loss of his beloved wife of 43 years to cancer, and the year hadn't improved since his retirement from his law firm in the summer. He thought he would love the free time his new lack of responsibility afforded him, but he instead found himself bored and lonely, finding company in books and the few friends from the local pub who hadn't moved to Florida yet. He spoke with his son occasionally, but he was busy with his own life and lived many hours away.

One Friday evening in early December, Bert found himself, as usual, having a few drinks at Smitty's Pub. His friend Don approached him, accompanied by a neatly dressed middle-aged man.

"Bert!" he cried, slapping him on the back, "How ya doin?"

"Same old, same old," said Bert, standing up and embracing his old friend, "How you been Don?"

"Still alive, so pretty good I guess! Say, Bert, I wanted to introduce you to my nephew Jack. You know these new laws that got passed a few months back? Well, Jack is the Chief Disciplinary Officer for the county, and I thought you two should meet. Might be an early Christmas present for you in it."

Don gave him a wink. Intrigued, Bert shook hands with Don's nephew.

"Good to meet you, Mr. Charrington," Jack said, "Uncle Don has told me a bit about you. I mentioned that we were looking for some men for a new type of experimental punishment regime we're phasing in, and, if you're interested, you might fit the bill."

Bert raised an eyebrow.

"Please, call me Bert. You've certainly got my attention! I've read a bit about these new laws, but as a retired lawyer I'm embarrassed to admit that I haven't gotten into the details. How might I be able to help?"

Jack nodded.

"Well, let me give you a little background. As you probably heard, the Women's Corrective Enhancements Act went into effect at the beginning of October. Generally, it provides for the use of corporal punishment on certain female offenders. The first phase was the opening of the Punishment Centers, which have been running well, as you may have read about. However, there are also alternative punishment regimes permitted under the law, and we're in the process of getting those running, including the experimental one that I had in mind for you.

Currently, we're starting up what we call "Private Domestic Punishments". As part of this effort, we are recruiting men who can carry out punishments on the young ladies sentenced under the new laws. Specifically, we need men who own their own home, preferably secluded, so the neighbors aren't bothered by the punishments. The men need to be respectable, with no criminal record. And they need to be fit enough to carry out what can sometimes be physically demanding work. And, for reasons I shouldn't get into here, widowers with no children living at home are preferred.

From what my uncle tells me, you fit our candidate profile perfectly. Would you be interested?"

Bert stared.

"Well, I'm, um... flattered that Don would think of me! But I don't know much about this. Would these women be coming over my house? What kind of punishments are we talking about?"

"Yes, you'd be hosting these young ladies for anywhere from a few hours to a couple days, but usually including at least one overnight stay. One at a time, probably between two and four times per month. As far as the punishments, we're mostly talking about corporal punishments. Spanking, belting, caning and the like. There's also... other punishments, but we can talk about those at a later date.

You'll receive training on how to deliver these punishments, so don't worry if you aren't experienced in these matters. What do you think?"

"Can I have the night to think about it?" asked Bert, "It's a lot to take in. But yes, I'm interested."

"Of course," said Jack, handing Bert a business card. "My mobile number is on there, call me when you've thought about it some more."

----------

"Bert, Jack Richardson here. Are you ready for your first assignment?"

It was mid-February, and the past two and a half months had been a whirlwind for Bert. He had accepted Jack's offer the morning after their meeting, and the same day had been thrust into months of physical and psychological tests, daily training, and, eventually, a series of certification tests, ensuring that he had properly learned the details of the new laws and mastered the skills he would be needing in his new position.

For the first time since his wife's death, Bert found himself excited about the future. He had aced his certifications, and Jack had told him privately that he had the highest scores of all their new Domestic Punishment Agents.

"Jack, great to hear from you! I'm ready. Excited to get started," said Bert.

"That's great to hear, Bert. This first assignment is a bit of a challenge, throwing you in the deep end, but the judge saw fit to pass this sentence. Since no Domestic Punishment Agent has any experience yet, as the highest scorer with the most punishment certifications, I've decided to ask you to handle this. I'm sending over the details now, take a look and see what you think. I can wait."

Bert's phone buzzed, and he opened the message he'd just received. His eyes widened.

"Wow, not what I expected for my first assignment! But you can count on me," said Bert.

"That's what I was hoping you'd say. Ms. Prixton will be dropped off at your house this Friday at 6pm. She will remain in your custody until 6pm on Sunday. That gives you a few days to prepare, which I assume will be sufficient."

Bert confirmed it would and wrapped up the call. He smiled to himself in anticipation of the upcoming weekend.

-----------------

DAY 1

Bert was waiting outside his door when the police sedan transporting 19-year old Hailey Prixton arrived. He looked very much a kindly grandpa in khakis and a sweater vest.

A police officer opened the back door and let Hailey out. She didn't look the type to be a felon, Bert thought. But, then again, as a lawyer he'd seen all sorts, and he admonished himself not to judge a book by its cover.

Hailey was petite, 5'2" and 105 pounds, according to the bio sheet that Bert had reviewed. She had long, straight brown hair that extended a few inches past her shoulders, and was pretty and well put together, looking every bit like a freshman sorority girl. But she wasn't. Instead Hailey had barely finished high school, and from what Bert had read was currently unemployed and living with her boyfriend, with whom she had recently stolen a car.

Bert smiled and offered his hand to the young woman as she was escorted over to him. Hailey, who looked nervous, shook it tentatively.

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"Thank you officer, I'll take custody of Miss Prixton from here," he said, and the officer returned to her car and drove away.

"Hailey, welcome to my home. I'm Domestic Punishment Agent Charrington, but you can just call me Mr. Charrington. Please, come in. Have you eaten dinner?"

"Um... yes, sir," Hailey said shakily.

"Good, good. Please, come into the living room so we can discuss how this weekend is going to work."

Bert felt his heart pounding. He had gone over this in his head a hundred times, but he couldn't believe it was actually happening. Domestic Punishment Agents had significant discretion in how they treated the women they were punishing, and he had decided to go with a kindly grandpa personality... until the punishments, of course.

Hailey sat down on his couch, and Bert sat down in a chair facing her.

"Now, Hailey, as you know, you've been convicted of some serious crimes, and it is my job to punish you. To that end, I have been provided with a list of punishments that I am required to carry out. However, I want you to know that other than the mandatory punishments, I intend to make your stay here as comfortable as possible."

Bert smiled at her, and Hailey tried to weakly return his smile. But she couldn't... instead she started to cry as the reality of her situation sank in.

Bert had planned for this. He got up and embraced her, patting her on the back and soothing her.

"It will be okay, Hailey," he said, "we're going to get through this."

Bert smiled to himself. One half of that "we" would have no difficulty getting through this, at least.

In a minute Hailey had regained her composure and Bert had returned to his seat. He smiled at her and continued.

"Now, I'm sure you were informed that I am fully in charge this weekend, and you are required to follow my instructions. As long as you do that, we can minimize the unpleasantness of this weekend for you. Can we work together to get through this weekend?"

Hailey nodded sullenly. "Yes, sir," she muttered.

"Good, I'm glad to hear that, Hailey. This may be tough, but complying with my instructions will be the way you get through this most easily. Now, let me show you to your room."

Bert showed her to a spare bedroom in his basement, which had been fitted with a door that locked from the outside. The room itself was quite pleasant, with a queen size bed and some basic furniture and a well-stocked bookcase, as well as an attached full bathroom. There were also, very prominently, two video cameras pointed directly at the bed and a third in a corner, taking in the full room.

"Some of your punishments will be carried out in this room, Hailey. The cameras record and transmit video and audio of the punishments so that my superiors can verify that I have carried out the sentence properly. Now, I have to request that you fully undress so that I can begin your punishment."

Hailey looked at him pleadingly. "Can you leave while I undress?"

Bert smiled his sympathetic smile at her again.

"I'm afraid not, Hailey. Also, I'll be taking your clothes, which will be returned at the end of this weekend. I'm sorry, but that's part of your sentence."

Hailey was breathing heavily but held back her tears as she slowly removed her shoes and socks, followed by slipping off her jeans and t-shirt. At that point she stopped, again looking at Bert.

"Everything, please, Hailey," he said with a sad frown, "I'm afraid the sentence is quite clear."

He pulled a paper out of his pocket and read off it.

"Prior to the commencement of the first punishment, the offender shall remove all of her clothing and jewelry such that she is presented to the Domestic Punishment Agent in a state of complete nudity. If she refuses, the Domestic Punishment Agent shall forcibly remove all of her clothing and jewelry. The offender shall remain in this state until immediately prior to her release from custody at the conclusion of her sentence."

Hailey's tears started again as she forced herself to unclasp her A-cup bra, revealing two small mounds that she had always been embarrassed about. Still softly crying, she slipped off her underwear, revealing a freshly waxed pubic area.

Bert could barely contain his excitement as she handed him the last of her clothing.

"Very good, thank you Hailey. Now, please lie face down on the bed. The first punishment is that I am to administer 50 hand spanks to your bare buttocks while you lie face down."

Hailey was visibly trembling as she climbed onto the bed and laid herself down. Bert positioned himself over her and placed his hand on her butt.

He couldn't believe this was happening. Him, a 65-year old man, with this adorable 19-year old girl lying in front of him, his hand on her tight young bottom, about to deliver punishment. And this was only the beginning...

Bert lifted his hand and brought it cracking down. Hailey gave a high-pitched yelp. "One," said Bert.

Bert's hand fell again, switching to Hailey's left buttock. "Two," he called out as Hailey squealed again and began to cry. Bert saw that her pale skin was reddening with his handprints almost immediately. He smacked her left butt cheek again, his strike partially overlapping with the existing handprint. "Three," he said, as she cried out in pain.

Hailey's butt was soon a mess of red as Bert's spanks fell over and over. After about 15 spanks, Bert noticed that he could no longer make out the individual handprints; instead, they had all blurred into a red field. At 20, he paused to consider how to proceed.

Hailey had been reduced to a squirming, blubbering mess. Bert was surprised, he hadn't expected such an extreme effect after only 20 hand spanks. And there were still 30 to go! He considered his next targets...

He used his left hand to spread her cheeks apart. "No, please!" she cried, as her most private parts were put on display.

Bert ignored her, instead landing spank number 21 sharply, millimeters away from Hailey's anus. He ignored her wails of pain as he switched hands and spanked the inside of the right butt cheek.

Bert's next eight smacks landed painfully up and down both sides of Hailey's crack, and by 30 the young woman's spread cheeks were glowing red all the way across. Hailey was a wreck, crying uncontrollably, nose running, breaths coming in gasps.

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Bert paused, considering his next move. Should he give her a chance to compose herself, or forge on and finish the spanking? His hand was tingling, but the months of training had prepared him for this.

He continued, slapping Hailey's already red butt full force. "Thirty one!" SMACK! "AAGH!" "Thirty two!"

By forty the redness had deepened, and by the time Bert's hand spanked the young penitent's bottom for the 50th time, it was clear that she wouldn't be sitting comfortably any time soon.

Bert gently patted her red butt. "That's all for now Hailey, you can sit up."

She slowly sat up on the bed, her pretty face red and sobbing. Bert pulled a few tissues out of a box by the bedside and handed them to her. Hailey blew her nose and dried her tears, which were still flowing but a bit more controlled now. Bert put his arm around her. Hailey flinched, but knew better than to move away.

"I'm sorry you have to go through this, Hailey, I'm sure that was painful."

Hailey sniffled and nodded. Bert put on his more sympathetic voice.

"It's for your own good, as hard as that might be to believe. If you keep going down this path, future punishments might be even worse, or you could end up in prison in addition to corporal punishment. We don't want that, and I need to make sure that you remember this punishment. Let's get through this and you can turn your life around, okay?"

Hailey nodded silently. But in truth? She didn't know how she could possibly get through this. If this was the first hour of her punishment, what would the rest of the weekend bring?

-----------

Bert sat on his couch thinking. He'd left Hailey in her room to shower and relax a little, telling her to join him upstairs at 8:30pm.

"Can I put something on?" she had asked, and he'd reminded her that she would be nude the whole weekend. She'd seemed distressed about this.

Bert took stock of how things were going. He'd expected Hailey to be a tough, hardened girl, considering her background and her crime. But instead a simple hand spanking had quickly broken her, and she seemed distraught at him seeing her naked. He wondered how she would handle her remaining punishments.

Bert heard footsteps on the stairs, and looked over to see a naked Hailey slowly walking up. She was trying to cover herself, and it was obvious from her eyes that she had been crying some more. She'd stopped now though, and looked at him surprisingly calmly.

Bert smiled at her. "Hailey, why don't you have a seat here on the couch with me."

The young woman tentatively approached the couch, and curled herself up into the corner, seemingly trying to make herself as small and covered as possible.

Bert gave her a sympathetic look. "How are you feeling?" he asked.

Hailey shrugged. "Pretty bad, I guess. I mean, I'm naked in your house getting spanked like a little girl. And I don't know what else is coming, but I know I'm going to be naked all weekend. And my life isn't exactly going great right now even aside from that."

Bert sighed. "Fair enough. I want to talk about how your life is going. Now, I've read your file, and I'd like to understand how you got mixed up in all this nonsense. Stealing a car?"

Hailey grimaced. "Yeah," she said, "I was dating a guy who was kinda bad news. We stole the car together, and got ourselves caught. But we broke up, and he's in prison now."

"I saw some of that in your file," said Bert, "You were living with him, weren't you? Where will you go now?"

Hailey shrugged. "I've been crashing with a girlfriend for the last week, but I don't know where I'll go after this weekend. I don't think my parents will take me back."

She started tearing up. Bert patted her legs and gave her a small smile.

"Look, Hailey, it's my job this weekend to punish you, and I have to do my job. But there's nothing that says I can't give you advice or help you out too, so we'll be discussing your future more this weekend. I really do want things to get better for you."

Bert meant it. He was a caring and thoughtful man, and he really did like to see troubled young people turn their lives around and succeed. But as much as he would have liked to say that was why he'd taken this role, he knew that wasn't true...

Hailey smiled weakly at him. "Okay," she said. "Are there more punishments tonight, or are we done?"

"There's one more tonight," said Bert, "but I was planning to give you a little bit of a break first. If you'd prefer, though, we can take care of it now and get it over with. It's embarrassing, but not painful.

Hailey gritted her teeth and nodded. "Okay, let's do it now."

"Brave girl," said Bert. "Okay, in that case, let's get started. The next punishment is called an exposure punishment. I'll give you instructions, and you have to put yourself in whatever position I ask you to. I'll be inspecting and touching various parts of your body as you expose yourself to me."

Hailey had closed her eyes and seemed to be slowly shaking her head "no". Bert used his phone to activate the camera system in his upstairs bedroom, which would record and transmit the footage of the punishment back to his superiors. He patted Hailey on her knees.

"Okay, Hailey," said Bert, standing up. Hop up, we're going up to my room upstairs."

She looked terrified as she stood up, keeping one hand over her breasts and the other down at her crotch. Bert found it somewhat amusing that she was still trying to cover up, knowing that in a few minutes she would be showing him every nook and cranny of her body.

He directed her up the nearby stairs and to a door at the end of the hall. As she walked ahead of him, he observed with some satisfaction that her butt was still very red from the recent spanking.

Bert stepped beside her and opened the door, ushering the young woman into his bedroom. A large king bed in an imposing wooden bed frame sat in the middle of the wall opposite the door. Next to it were two nightstands on either side. A dresser stood against a side wall. There was also another door in the room, which led to a full en suite bathroom. A camera was mounted to the wall facing the bed, and another faced the corner of the room, where there was a chair.

Hailey's eyes were glued to the corner with the chair. To Hailey's horror, she immediately saw that it was no ordinary chair, but instead appeared to be a modified gynecologist's chair, with stirrups and a rolling stool in front of it.

Bert closed the door and he heard Hailey's breathing quicken as she realized that her punishment was imminent. She had stopped crying for the moment, but was staring at the chair with increasing fear. She had just noticed the various sets of straps on the chair, and the mirror that had been installed on the ceiling above it.

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