The past catches up with one girl

By Duncan Wade

Helen Carter was an estate agent in a small market town in the home counties. The small office was located in the high street and was a converted stable dating back to the 16th Century. She had become the sole proprietor of the business after her divorce from her much older husband after only two years together. They still remained friends, and had the occasional dinner together but their marriage was much more about business than love. She had started dating again but hadn’t met anyone for even a casual date for a while. As she drove to her meeting that spring Monday afternoon, she had much more on her mind than her rather dull love life.

Helen may have been unlucky in love, but she was good at business, and today she was very keen to land a contract to sell the recently completed old school development. An old school built in the 1800s had been converted into eight luxury apartments by a local developer, and she had a meeting today on site to have a look round and hopefully land the marketing contract.

Helen parked her smart Mercedes in what was the old school’s playground which had been marked out into designated parking bays for each apartment. She checked her make-up in the illuminated vanity mirror. She had made a special effort today with her appearance. Her shoulder-length light brown hair was lightly curled and worn loose. She was wearing more make-up than usual, and in particular she had on bright red lipstick that always gave her a confidence boost.

To complete her professional look, she was wearing an expensive two-piece dark grey suit with a pleated skirt, some shiny flesh-coloured stockings, and a pair of black court shoes with red soles.

The conversion from old school to luxury flats had taken a while and there were still workmen in hard hats milling around. Of course, all eyes were on Helen as she strode confidently into what was to become the show flat.

“Hello, you must be Helen,” said a young man as he held out his hand, adding, “I’m Peter. We spoke on the phone.”

“Yes. Hello Peter, nice to meet you in person,” Helen beamed back at him.

Peter explained to Helen over a cup of coffee made by him in the new apartment’s luxury kitchen that he was the owner’s development agent. If it were up to him, she could start marketing the development straight away but, as he put it, the owner, a Mr James, was rather pedantic and wanted to be sure Helen was fully acquainted with the old school building before he could consider her acting for him. Mr James would be there in about an hour, when Peter felt sure she would be able to sort out any contractual stuff with him.

Helen thought this a little odd, but the name ‘James’ rang a bell. As soon as they had finished their coffee, Peter gave her what he called the ‘grand tour’ of each of the apartments in turn. It took a while to go into each flat and listen to Peter as he explained in some detail about how each flat had been designed. With a few sets of stairs to climb, Helen smiled to herself on several occasions as she caught Peter having a peek up her short skirt. If this mysterious owner was anything like Peter, the contract would be hers. Of that, she was sure.

“So that, as they say, is that,” Peter smiled as they returned to the marketing flat.

“Okay, but we only saw seven flats. I thought the plans said eight?” replied Helen.

“Yes. Sorry, I forgot to mention Mr James has decided to keep the largest flat for himself for the time being. It was originally the headmaster’s study, and we have merged it with the old school library. It’s now a two-bedroom apartment, but unlike the other flats we have kept most of the school fixture and fittings, the oak floors and wall panelling.”

“How interesting,” Helen replied, tilting her head to one side as she spoke.

Before either one of them could say anything, a red Ferrari arrived in the car park and out stepped a very distinguished middle-aged man wearing a smart suit with a blue and white striped tie and matching silk pocket square. He entered the building and came to the marketing flat.

Peter started to introduce Mr James to Helen, but as he did so he could somehow sense that no introduction was needed.

Ignoring Peter, the smiling Mr James beamed, “Helen! What a wonderful surprise. I had no idea that Mrs Helen Carter was the one and same Miss Helen May.”

“The very same,” replied Helen, still not sure how she was feeling about meeting Charles James after almost 10 years. Nonetheless, she beamed her best ‘estate agent’ smile.

After a few minutes chat between all three, Peter said his goodbyes and shook Charles’ and Helen’s hands before leaving.

As the building workers started to pack their tools away for the afternoon, Charles and Helen sat in the marketing flat looking at each other in a slightly uneasy silence.

Checking no one could overhear their conversation, Helen broke icy tension with a cheery, “Well Charles, you have done well for yourself in the last ten years.”

“So have you,” replied Charles James, adding, “We’ve both come a long way from the Kat-Kraker Club.”

Helen blushed as she replied, “I was just working for you while I was studying, Charles, as well you know.”

“From lap dancer to county set estate agent?”

“And you from seedy club owner to county developer of historic buildings?”

They both laughed. Then Charles invited Helen upstairs for a glass of wine in the last remaining apartment.

Helen thought for a second.

“Okay, but no funny business,” she grinned.

“Of course not, and in any case we’ve got a contract to discuss, Mrs Carter,” replied Charles as he pushed the call button for the lift.

They ascended in the lift, and then the lift doors opened in the centre of the spacious top-floor apartment. Helen was immediately impressed.

“I can see why you have kept this for yourself, Charles.”

“Yes, thanks, I’ve got it just the way I like it. Have a look round. White or red wine?” Charles replied from the marble-surfaced kitchen.

Helen put her coat and large handbag down, quickly re-checked her make-up in her compact mirror, added a splash of perfume. She was sitting in a high-backed leather armchair and showing a lot of leg when Charles returned with their wine.

Over the next twenty minutes or so, they brought each other up to date with their lives during the previous ten years. It turned out that Charles was on his second wife, and had two teenage boys at boarding school nearby, which was why he wanted to hang on to the apartment.

Helen sat bolt upright, now firmly back in work mode.

“That’s all very well, Mr James, but as time is getting on, can we discuss the terms of the contract and maybe we could conclude our business today.”

Charles took a while to reply. It had hadn’t taken long to track down the gorgeous Helen, but now she was sat in front of him he wasn’t sure she was going to play along with his plans.

Speaking softly, Charles outlined his requirements for selling the apartments. Helen made a few notes as he spoke. He would pay double the going rate, and pay for the advertising costs. While Helen wanted to cheer out loud, she could sense there was something else Charles wasn’t mentioning. It didn’t sound like a seduction-type conversation, and while Charles went on about the contract Helen’s mind drifted back ten years to the Kat-Kraker Club.

It was just a small lap dancing club that had once been a pub in the east end of London. Helen had first started as a barmaid, but soon picked up the courage to learn to pole dance, and she made good money from the city-type clientele looking for a few cheap thrills on their way home.

Then Helen heard Charles say, “So, if we can deal with the issues I’ve mentioned, then I’m happy to sign now.”

Helen instantly snapped her attention back to the present. Charles James leaned back in his chair and waited for Helen to respond.

Helen crossed and uncrossed her legs, took a long sip of wine and said, “’Sorry Charles, what issues are you talking about? If you are wanting references, I can assure you that…’

Charles cut Helen off in mid-flow.

“I’d like to show you something, Helen,” said Charles as he stood up. His confidence was returning.

Helen didn’t answer, but just obediently followed him along a short corridor to a set of double doors somewhat out of keeping with the rest of the modern flat. Then she remembered what Peter had said about keeping the school library in the penthouse apartment.

Once inside the double doors, Charles then spoke.

“I’ve always had a thing about schooldays, Helen, so when the chance of this development came along I jumped at it. Now I have my own piece of a school to myself.”

Helen looked around. It was amazing. The room had the same flooring as the rest of the flats, but in this room the walls were oak lined and mostly filled with books. There was a large desk with an authentic-looking desk lamp, a smaller desk with a lift-up lid and an ink well, and a smaller leather sofa similar in style to the chair in the main lounge.

“It’s really authentic, Charles, and it sort of keeps the old school alive,” smiled a relieved Helen, who had been thinking they might be heading to the bedroom.

As Helen span around, she caught site of an umbrella stand containing several umbrellas, and also several canes, some with a crook handle, some just straight. It reminded her of the old Kat-Kraker club and some of the rumours she’d heard from the other girls.

Charles sat down at the large desk, and Helen intuitively sat down opposite him and waited for what she almost knew he was going to ask.

“Just now, when you mentioned keeping the old school alive, that’s exactly it. That is sort of what I want to do. In fact, it almost seems a shame to waste this wonderful school environment.”

“So, Charles, how could it be wasted?”

Charles hesitated. The pause aroused Helen’s suspicions.

“You didn’t really find me just by chance, did you Charles? Getting me in to market this place was all part of your plan, wasn’t it?”

Charles James smiled. Helen was perfectly correct. It had taken some time to track her down and when he learned she had her own estate agency business, an idea suddenly came to him. He leaned back in his chair, feeling like a headmaster with an errant pupil in front of him.

“You know, the cash was always short at the Kat-Kraker bar, Helen. I knew it was you, and from what I remember it was a fairly large amount that you stole over the course of the six months you worked for me. I always liked you, Helen, but why should I trust you now? Why should I offer you this rather valuable contract?

“Am I wasting my time here, Charles? Do you want me to leave?”

“No, but if we’re to have a business future together, perhaps we need some sort of closure of the past.”

Charles leaned forward and put his hands together, holding his breath for Helen’s reply. She was a beautiful woman, but would she sense what he was hoping for? Would she be horrified, or would the lucrative contract entice her?

Helen stared at Charles, then very slowly stood up, smoothed down her short skirt and re-arranged her shoulder-length hair. She was clearly thinking over her next words very carefully.

“Yes Charles, it was me that stole from you. I am very sorry. I was really short of money at the time, and I always intended to pay you back. Then I met my husband and things moved fast. I ended up here living another life. Please forgive me.”

Helen lowered her head, hoping her ‘poor me’ speech had worked and that Charles could somehow forgive and forget and they could move on into a whole new business relationship.

“You put on a good show, Helen, but then you always did. I think our meeting has run its course, Mrs Carter. I’ll be signing up with another agency.”

Charles extended his hand towards Helen, inwardly hoping she wouldn’t take it, or walk out the door.

Helen smiled and took another sip of wine.

“Okay Charles, what do you really want? You know I want that contract and you know I’m the best estate agent in town. You tracked me down and brought me here. You didn’t go to all that trouble just to watch me walk out the door. I’ll say again, what do you really want?”

Charles walked round his desk and sat on the front edge. He smiled, sensing they both knew where this was leading.

“You know, when I was at school, Helen, naughty girls were smacked soundly on their bottoms. Being that we’re having this conversation in an old school building, perhaps we should respect the old ways, don’t you think?”

‘So the rumours were true,’ thought Helen, her mind racing back to overheard conversations back in the changing room of the Kat-Kraker club.

Helen’s options were clear. Take some kind of a spanking and she would get the contract, the contract she was desperate to win. Decline, and she would have to walk out the door empty-handed. It took just a few moments to decide.

“Okay Charles, you can punish me, but I want the contract signed first, and I want an assurance that you won’t tell anyone about this, and that you won’t be putting me in this situation again. It will be a one-off and henceforward our relationship will be just business. Is that understood?”

Charles grinned as he listened to Helen’s conditions. He had already played out a thousand times in his mind having the delectable Miss May across his lap, or perhaps bent over a desk. Now, after ten long years, it looked like it was going to happen at last.

“You have a deal,” replied Charles as he took a pen from his inside jacket pocket and signed the contract. Helen also signed. He placed the contract face down on his blotter and placed a paper weight on top of it. They both stood in silence for a moment, then

they shook hands.

“So, where do you want me, headmaster?”

Charles smiled as he heard himself being addressed as ‘headmaster’. Helen had always been a bit of a tease. Looking into her large brown eyes, he sensed her nervousness. Was she was having second thoughts? Was his fantasy about to slip away? Charles hastened to reassure Helen.

“Look, the contract has a cooling-off period. If you are having second thoughts, now’s the time to speak up, Helen.”

Helen smiled weakly. “I’m willing to fulfil my side of the bargain, Charles.”

Charles smiled broadly. He went across to the umbrella stand and took a few moments to select the implement of his choice, a two-foot-six-inch straight cane with blue tape wrapped around one end to form a handle. He then went behind the small two-seater sofa and tapped the backrest with the tip of the cane.

As Charles waited, Helen put her handbag on the desk and kicked off her shoes. She leaned on the desk to carefully removed her tights, and then stepped towards Charles. She nodded to him as though confirming acceptance of what he was about to do to her.

“I think, across the back of the sofa would be ideal,” Charles informed her as he stood back to allow Helen to assume the position.

How many strokes am I getting?” Helen asked as she stood at the back of the small sofa.

“I think, twelve strokes, a round dozen.”

Helen considered the punishment for a few moments, then nodded.

“Okay, headmaster.”

Without being asked, Helen eased her short skirt up above her waist and slipped the dark blue knickers she was wearing down to her ankles.

“Nothing you haven’t seen before, right Charles? Back in the changing rooms at the old Kat-Kraker club?”

Charles smiled ruefully. Yes, he had often entered the girls’ dressing room without knocking, and he had sometimes been rewarded by catching a girl or two in some state of undress. He thought the girls simply accepted it as part of the hustle and bustle of a busy club, but Helen was suggesting he had acquired some sort of reputation as a lecher. Whatever, the Kat-Kraker club was long gone.

“Have you had this done before, Helen?”

“A couple of times. One or two of the old customers back at the club. And a little incident that was dealt with off-the-record at boarding school.”

“Really? I didn’t know that.” Charles was tempted to ask for more detail, but hesitated.

Helen smiled. “Shall we begin?”

“Very well, bend over, girl!”

“Yes, sir.” Helen slowly bent herself over the back of the small sofa, the material covering the top rail feeling rough against her stomach. “How is that, Charles? Am I presenting a good target?”

Charles coughed. “That’s excellent, Helen. Hold still.”

Charles lifted the hem of Helen’s short skirt a little higher, revealing more of her lower back. He took his time, and ran his hand over Helen’s naked bottom, savouring the moment.

Helen was content to let him have his moment of fun. The lucrative contract he’d signed would be ample reward for her. Only one thing troubled her; this caning was going to hurt!

“You are going to smack my bottom today, are you Charles?” she goaded him.

Charles sensed she was provoking him, and he immediately tapped Helen’s bottom a couple of times before applying a sharp, swishing stroke across the woman’s creamy white bottom.

Helen flinched as the pain spread across her bottom.

Second and third strokes followed slowly but surely, each intensifying the pain. Helen then felt Charles’s hand softly rubbing over her bottom as he explored the damage he’d just caused.

“Achieving the desired effect, Charles?”

“Yes, thank you.” Charles wasn’t sure how to take Helen’s comment.

He readied himself with a firm grip on the cane and applied three more strokes quite rapidly and with little time in between.

“Ouch!” Helen exclaimed loudly. “God, that really smarts!”

Charles smiled to himself. The day had gone well. He was achieving what he set out to do.

“This is well overdue, young lady. Justice finally being served for your misdemeanours of years ago.”

“Yes, sir.”

Charles applied the seventh and eighth strokes more slowly, aiming specifically at the lower portions of Helen’s bottom. Driving herself home was going to hurt!

“My god! You’re really laying it on, Charles!”

“Too much for you, Helen?”

“No,” she responded defiantly. “I was a naughty girl, back at the club. I can take my punishment.”

Charles smiled. He whipped the cane down twice in very quick succession. Helen jerked and gasped as the strokes impacted with her naked bottom.

“Just two more strokes, Helen,” Charles informed her.

‘And I bet you’re going to make them count!’ thought Helen to herself as she braced herself.

She was correct. The final two strokes, delivered just a second or two apart, stung more than any of the previous ones.


Charles took a few moments just surveying the results of his efforts, noting the twelve distinctly separate red lines across Helen’s milky white bottom. He felt both exhilaration that he’d achieved something he’d dreamed about for years, but also disappointment it was now all over.

“May I get up now, sir?” Helen emphasised the word ‘sir’.

“Eh? Oh, yes, sorry Helen.”

Charles watched as Helen stood up and unashamedly rubbed her bare bottom.

“So, are we all settled now, Charles?”

“We are, Helen.”

He held out his hand and they shook hands.

“That was a pretty good hiding you gave me, Charles,” Helen said, still rubbing her bare bottom in plain sight of Charles.

“You deserved it, Helen.”

“True. It will be good working with you again. Who knows, if I don’t do a good enough job, you might have to chastise me again!”

The End

© Duncan Wade 2022