Challenging Chelsey

(7 customer reviews)

 “What happens if I don’t do what I’m told? Do I get punished?”

Six years ago, Chelsey Roberts’ life fell apart when her parents and older brother were killed in a terrorist attack in London.

When Harry Ratcliffe, her brother’s best friend finds her homeless and begging for change, he offers her a place to stay and the chance to turn her life around. It’s what anyone would do in the circumstances, right? For old times’ sake.

But Chelsey isn’t a teenager anymore. Their feelings for one another grow and Harry discovers that he would do anything for this woman. Including giving her the discipline that she needs.

Harry challenges this erratic young woman to obey him and accept his punishments and through his care, Chelsey finds a new freedom and happiness which helps her overcome the demons of her past.

Publisher’s Note: This contemporary romance contains adult themes, sensual scenes and power exchange. If any of these offend you, please do not purchase.

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Sample Chapter

Even though it was the middle of summer, the rain was torrential. It cascaded down from the sky in sheets, soaking the city streets. Just your typical London summer, thought Harry Ratcliffe, as he left his office. He pulled up the hood of his coat and hurried to the pedestrian walkway at Aldgate.

He descended the stairs into the underpass. The covered walkway gave some respite from the pouring rain but it was in no way a pleasant environment. The stench of rubbish, rancid food and urine filled his nostrils. Harry kept his head down and walked quickly.

There was a homeless person sitting on the floor halfway along the underpass on a dismantled cardboard box. A grubby rucksack sat next to the beggar who was a filthy mess of crumpled clothing and tangled hair. The sound of their hacking cough echoed round the enclosed space.

Someone ahead of Harry – a middle-aged woman in a business suit – stopped and put some money in the empty Starbucks cup that served as a collection tin.

“You take care now,” said the woman.

The homeless girl – and she clearly was female now that Harry bothered to look at her – pushed her hair away from her face and smiled at the woman.

“Thanks,” she said. “You too. It’s pissing it down out there.”

“Tell me about it!” replied the woman affably and went on her way.

Harry stopped in his tracks. He knew that woman. Not the businesswoman, the scruffy homeless girl begging for change. He recognised her.

Well, of course he recognised her, he told himself. She was often down here; he’d walked past her several times already this week. He’d never given her any money, he realised. There were so many beggars in London that he tended to tune them out.

He had never heard her speak before though. Her voice, her smile and the way she looked when she pushed the hair back from her face – all those things stirred a memory from a long time ago. Harry racked his brain to recall what it was.

And then he remembered her. And the painful memories of six years ago came crashing back.

He quickened his step as he walked up to her. “Hi Chelsey,” he said. He got down on his haunches so that his head was level with hers. “You probably don’t remember me…”

“I remember you, Harry,” she replied. “How are you doing? You’re looking well.”

It was on the tip of Harry’s tongue to say, “You too,” just out of politeness but it would have been a lie. She didn’t look well at all.

Chelsey’s hacking cough started again which put paid to any further conversation for a few minutes. Harry stayed in his crouched position waiting for her to finish. Despite all the layers of clothing that Chelsey had bundled herself up in, Harry could see that she was seriously underweight. The hand and forearm that she held up in front of her face were stick thin and her face looked hollowed out and gaunt.

When the coughing fit had finally subsided, Chelsey smiled apologetically. “Sorry about that, bit of a tickle. Don’t suppose you’ve got a spare tenner have you, Harry? So that I can get a bed for the night?”

He had ten pounds that he could give her, of course he did. He could give her a hundred pounds if he thought it would help. But what good would it do? She’d still be here, in this piss-stinking underpass begging for change from strangers. How bad must things have gotten that she was reduced to this?

“Do you want to come home with me?” he asked her.

Chelsey narrowed her eyes and then laughed. “Is this a pick-up line? I’m not that kind of girl, you know. Although, oddly enough, I do get asked that a lot. It seems that plenty of guys assume that being homeless and female naturally equals being a cut-price sex worker.”

Well, that settled it. He wasn’t leaving her here a minute longer than he had to. “You know that’s not what I meant. I have a spare bedroom, a washing machine and a fridge full of food. Come and stay with me for a while, sort yourself out.”

“Why are you being nice to me?” asked Chelsey suspiciously.

“Because you’re my best friend’s sister. I want to help.”

Ex best friend,” Chelsey corrected him.

“Well, yes I suppose. If you want to put it like that.”

He stood up straight and extended his arm to Chelsey. “Right,” he said. “Are you coming with me or not?”

Chelsey took Harry’s proffered hand and allowed him to pull her up. “Okay, then. Thanks,” she said.

Harry helped Chelsey gather up her meagre possessions and the two of them set off back to his flat.

He wondered what on earth he had gotten himself into.


Chapter One


One month later, Chelsey Roberts lay in the single bed in Harry’s spare room, her head underneath the pillow in a vain attempt to ignore what Harry and his new ‘friend’ were up to in the room next door.

Her pillow was pressed against the back of her head covering both her ears entirely. But it didn’t manage to block out the sounds from the next room. In particular, the sounds of Harry’s palm smacking against the flesh of his late-night guest. Chelsey heard the yelps and squeaks as each swat made contact.

She flung the pillow across her bedroom. It was no bloody good. There was no possible way she could pretend that she couldn’t hear it. She was grudgingly impressed that Harry seemed to find no end of willing young ladies to bring home and suffer this kind of treatment.

She was absolutely in no position to complain about it. Harry Ratcliffe was doing her a huge favour in allowing her to stay at his flat rent-free. As her brother’s best friend and knowing everything that Chelsey had been through in the last few years, he had wanted to help. She knew she wasn’t the perfect houseguest. She’d tried his patience enough in the month that she’d been staying at his place. She couldn’t very well ask him to keep the noise down when he brought a girl home for a bit of sex ‘n’ spanks.

Chelsey huffed to herself as she adjusted her position on the bed. The sounds of the spanking reverberated through the wall. Maybe she should just go out. Grab her coat and go for a quick jog around East London at – she glanced at the clock – twenty to one in the morning. She shivered. Maybe not. It was dark and drizzling out there. Plus it was hardly her fault that she had, once again, been turned into whatever the aural equivalent of a voyeur was. Maybe she should just enjoy it.

She smiled at the thought and moved her fingers between her legs, rubbing herself gently and finding herself wet to the touch. Clearly, the sounds of Harry’s evening entertainment were already having an effect on her. She began to slide her fingers across her opening and against the nub of her clitoris as she tried to picture what Harry was doing right now.

She could picture Harry easily, tall and broad-shouldered with a mop of messy dark blond hair. She had seen him come out of the bathroom in nothing more than a towel on many occasions now and knew how well sculptured and defined his chest was. She didn’t know who the girl he had with him was but that didn’t matter. Chelsey didn’t care about the girl. She could mentally sketch her using one of the other girls that Harry had brought home since Chelsey had started living there. They were always attractive and well-groomed, the sort of girls Chelsey usually felt a bit intimidated by. When Chelsey had met any of them, they’d look at her with anything from curiosity to open hostility clearly not expecting to find another woman in Harry’s kitchen first thing in the morning.

Not that they’d have anything to worry about, Chelsey thought to herself. Harry clearly doesn’t feel that way about me at all. More’s the pity. She had to admit to herself that she had fancied Harry since she was in her early teens. He had been the best friend of her older brother, James. Harry and James were both four years older than she and had seemed impossibly grown-up and glamorous back then.

Not that anything much had changed in that regard. Chelsey was twenty-two now but given that she was broke, jobless and homeless while Harry was a financially successful solicitor who owned his own London property, she felt a long, long way from catching up with him in the grown-up stakes just yet. He still seemed like the grown-up. She still felt like a kid.

Chelsey imagined Harry sitting on the straight-backed chair in his bedroom, the girl bent over his knee as he administered swat after swat with the flat of his hand. Harry would be fully dressed, probably wearing one of his well-cut business suits, jacket off, sleeves rolled up to the elbows, his tie loosened but not removed. The girl would be completely naked, showing that the balance of power was entirely in his favour. She pictured the girl’s exposed buttocks turning redder and redder as Harry kept up the steady tattoo of spanks across them.

Chelsey worked her fingers quickly across her pussy as she pictured the scene. The sounds of spanking next door had stopped and she couldn’t hear anything but a few muffled thumps and some inaudible conversation. But it didn’t matter. Chelsey’s imagination was in full flow now. She imagined that when Harry had finished the spanking he would push apart the legs across his lap a little, the better to access the damp wet space between them and slip his fingers deep into her folds pumping in and out as she bucked and moaned on his lap.

Then he would tell her to get up and manoeuvre her onto the bed. Positioning her on all fours so he could admire the redness of her backside, as he swiftly entered her from behind filling her pussy with his hard, enormous – she always assumed he was enormous – cock and rode her fast until they were both sore and sweaty and utterly satiated.

Chelsey gripped the bed covers with one hand as her other hand frantically rubbed against her clit bringing herself to a breathless orgasm. The almost unbearable pleasure crashed through her, as she struggled to keep herself silent. She made barely a sound, and she did not move enough to cause a solitary bedspring to squeak. Chelsey had been kipping on people’s sofas and crashing on the floors of friend’s bedsits for years now. She was very good at masturbating discreetly.

As she lay there, ever so slightly out of breath, she realised that throughout her fantasy whenever she had pictured the girl that Harry was with, she had been picturing herself.

Despite the rhythmic noise of the headboard pounding against the partition wall, Chelsey drifted off to sleep.


Harry unlocked the door to his flat and entered. “Hi honey, I’m home!” he bellowed.

“Hey,” called Chelsey from her bedroom in response.

Harry wondered what Chelsey had been up to while he had been at work. She was supposed to be looking for work but Harry suspected her job-hunting attempts were somewhat half-hearted. In fact, half-hearted was probably too generous a description. If she could give it even half her attention she’d be doing better than she was now. He didn’t want to nag though. It was a difficult situation and Chelsey had proven she had a habit of disappearing in the past. She’d been living on the streets prior to staying at his place. He hated to think what might have happened to her out there. Right now he knew where she was and he knew that she was safe. The last thing he wanted to do was push her away.

He groaned when he entered the kitchen. There were dirty mugs and plates stacked on the filthy countertop. The bin was covered in tea streaks from inaccurately lobbed tea bags. More worrying still, there were a couple of empty lager cans on top of the mess. Daytime drinking really wasn’t going to help Chelsey’s job-hunting process.

Okay, he might not want to drive her away, but he had to admit to himself that Chelsey not being here had a certain amount of appeal. Having the place to himself where the kitchen was always spotless because he always left it that way. He missed those days. Had it only been a month since he’d been able to enjoy a bath without having to rinse the tub free of leg stubble and fish all her hair out of the plughole first? It felt a good deal longer.

Chelsey appeared in the kitchen doorway. She looked like she’d been napping. Her hair was mussed and the t-shirt and sweatpants she wore looked crumpled.

“Hi there,” he said. “Busy day?”

She shrugged. “Oh you know,” she said. “Same old, same old.”

I don’t know, thought Harry. I have absolutely no idea what you get up to for the ten hours I am out of the house each day.

She opened the fridge door and tutted. “We’re out of milk,” she said.

Harry couldn’t keep the irritation out of his voice. “Well, don’t you think you could go and get some? You finished the last pint after all.” He could see the empty plastic bottle lying over the dirty dishes and with a surge of annoyance picked it up and shoved it forcefully into the bin.

“That’s supposed to go in the recycling…” began Chelsey.

“Shut up,” snapped Harry.

Chelsey blinked in surprise. She wasn’t used to Harry being short with her.

Harry reached into his pocket and pulled out a ten-pound note. “Right,” he said, handing it to her. “Go to the corner shop and buy a bottle of semi-skimmed. You think you can manage that?”

Chelsey shrugged. “Sure. Whatever,” she said. She stuffed the note into her bra and wandered into her bedroom. She reappeared a few minutes later now wearing boots, a coat and an extraordinarily tea cosy-looking woolly hat. “Want anything else?” she called from the door.

“No, just the milk,” said Harry tersely. Don’t want to over-stretch your ability to follow orders at this stage, he thought.

He then set to work washing the dishes and cleaning the kitchen, berating himself as he did it. He really should get Chelsey to do this, he knew. But it just seemed easier to do these things himself. That’s how things had been for the last month, he realised. He picked up after her, he took care of everything. Not only did she live here rent-free but he was paying for all the groceries and even cooking for her most nights. Maybe things needed to change. He wanted Chelsey to start accepting some responsibility for her life. That wasn’t going to happen while he was still doing everything for her. She was twenty-two years old. She needed to start acting like it.

When Chelsey got back from the shop, Harry could tell at a glance that her shopping trip had consisted of more than the pint of milk he had asked her to get.

“I got us some wine as well,” said Chelsey, pulling a bottle of Pinot Grigio from the carrier bag. “I thought we could have it with our dinner tonight. What are we having?”

“I haven’t started anything yet,” said Harry. “Why don’t you cook tonight?”

“Seriously? I just went and got the milk.”

“And you think that means you’ve contributed enough for the day, do you? While I’ve been at work since eight o’clock this morning? You don’t think I might be a bit more knackered than you are?”

“Given the time you were up to last night doing Fifty Shades of Grey shit with your new playmate, I imagine you’re pretty knackered, yeah,” said Chelsey.

Harry, who had just been about to respond, shut his mouth with a snap. He had no idea that Chelsey had heard what he had been up to with the girl he’d brought home from the bar last night. Harry felt quite embarrassed about the idea of James’ kid sister hearing the sounds of him fucking a complete stranger – Grace? Gwen? He had forgotten her name already – in the next room. He knew, logically that Chelsey was a full-grown woman but in plenty of ways he still thought of her as the twelve-year-old brat he had met the first time he had seen her at James’ house. All those years before tragedy hit.

“I’m sorry. I didn’t mean to disturb you,” he said quietly.

“Nah, it’s fine. Don’t worry about it,” shrugged Chelsey. “So, what shall I make for dinner? I’ve never really done any cooking. I don’t know how to make anything. Do you fancy beans on toast?”

Harry smiled despite himself. “I think we can do better than beans on toast,” he said. “How about spaghetti Bolognese? I can teach you how to make it.”


“This is really good,” said Chelsey as they sat down later and began to eat.

“It is,” agreed Harry. “You should be proud of yourself.”

“I don’t think I can take much of the credit,” scoffed Chelsey. You gave me step-by-step instructions all the way. It must have been more work for you than actually just cooking the meal yourself.”

“I was happy to do it,” said Harry. “And it was hardly a waste of my time. You know how to cook something now. You’ll be more confident about cooking something again in the future. It’s ridiculous that you’ve reached your twenties with no idea about how to cook.”

Chelsey shrugged. “I’ve never had a kitchen,” she said.

“Well you have a kitchen now.”

“It’s not my kitchen.”

“Oh what bloody difference does it make? Most people learn to cook before they get mortgages you know. You have access to a kitchen. You are free to cook in it whenever you want. In fact I would welcome it if you did.”

“Is that the deal now? That I have to have dinner on the table for you when you get home from work? Like a good little housewife? Or a well-trained housekeeper?”

Harry put down his fork and looked across the table at Chelsey. “Not in so many words but yes, I think you should take more responsibility for doing things round the house. I am happy to have you here but there’s no reason why you can’t pull your weight. You’re more than capable.”

“So what do you want me to do?” she said. It sounded sulkier than she had intended it.

“We’ll discuss it after dinner,” said Harry brusquely, putting another forkful of pasta into his mouth.

When they had finished eating, Chelsey took the plates into the kitchen before Harry could do so. If she was honest with herself – and she suspected she very rarely was – Harry had a point. She knew she didn’t do anything like her fair share of work around the house. And that was even without taking into account the fact that Harry worked full-time while she didn’t work at all. Not to mention the fact that he was letting her stay rent-free. If he’d rented his room out instead of letting her stay in there then he could easily get about seven hundred quid a month for a room in Whitechapel. It probably wasn’t too much to ask that she cook occasionally.

When she went back into the living room, Harry was seated at the dining table but had grabbed a notebook and pen. Looks like he actually means business, Chelsey thought.

“Okay Chelsey, here’s the deal,” he said. “Like I said, I’m happy to have you carry on living here. James was my best friend and I’ve always been fond of you, you know that. But you need to have a plan. You can’t just keep aimlessly drifting. You’ve been doing far too much of that for the last six years.”

Chelsey bit her lip and shook her head slightly, trying not to think of the horrible, awful day six years ago that had cast her so adrift. “I’m sorry, I know you’re trying to help but I don’t know if I can do what you want me to.”

“I’m not going to ask a lot. I am not going to ask you to do anything you can’t handle. But you’re a capable girl. You’ve just never given yourself the chance to prove it.”

“I need to get a job, don’t I?” Chelsey had had a few jobs over the years, both legal and occasionally not so legal. None of them had ended well. The not-so-legal one especially although, thankfully, after she was caught dealing small quantities of cannabis, the police let her off with a caution rather than prosecuting her. She’d decided pretty quickly that drug-dealing wasn’t for her.

“Not necessarily. You need to have a plan though. Like deciding what sort of job you want to do and making a certain number of job applications each day. Of course getting a job might not be the best option for you right now. You might want to study instead. Or do an apprenticeship. I am happy for you to carry on living here at the moment so that would help with the costs.”

“You’d pay for me to go to college?” asked Chelsey.

“Well not the course itself, obviously. You can take out a student loan for that like everyone else. I’d support you while you did it, though.”

Chelsey felt a little overwhelmed by his offer. She hadn’t given any thought to studying full time since she had left school at sixteen with a fairly unimpressive clutch of GCSEs but now that Harry had suggested it, the idea appealed to her a lot.

“I really like the idea of studying,” she said. “Maybe I could study something that would let me get some kind of teaching qualification. Does that sound stupid?” she asked, suddenly worried.

Harry looked genuinely baffled. “Why would that sound stupid?” he asked,

“Because I’ve only got five GCSEs, none of which are higher than a C grade. I never went to sixth form college. I’m an idiot. I’d make a really shit teacher.”

“You’re not an idiot,” Harry said firmly. “You know you’re not. And you know, there were kind of extenuating circumstances when you took your GCSEs.”

They both went quiet. Funny, thought Chelsey, when this was clearly the main thing that held her and Harry together and the reason he was so keen to help out, how little they had mentioned Chelsey’s parents or her brother James. How they had all been killed on that terrible awful day in 2013 and how Chelsey had lived. Not only finding herself suddenly brotherless and an orphan but also having to deal with the crippling survivor’s guilt. She had been there too. Yet she had survived while they had all been killed. Although she knew at a logical level that she was in no way responsible for the terrorist attack on the tube station, she still felt like she would never ever forgive herself. She didn’t deserve to be alive when those whom she had loved most of all were not.

Harry leaned across the table and gently took Chelsey’s hand in his own. She guessed it was obvious to him where her thoughts were at that moment.

“You can do this, Chelsey.” he said quietly. He opened the notepad on the table and started to write. “There’s your first thing to do then. Look into what courses you could study and find out what you would be interested in pursuing and what pre-qualifications you might need to get. Let me know what you’ve researched tomorrow evening.”

“You’re giving me orders?” said Chelsey incredulously. I mean, sure it was nice of him to offer to support her, but she hadn’t been accountable to anyone since she was sixteen years old.

“That’s the plan. I’d like you to trust me enough to take orders from me.”

“What happens if I don’t do what I’m told? Do I get spanked?”

“What?” Harry dropped his pen in surprise.

“Well you’re clearly into all that Dom stuff. Seems like there’s no point in you issuing orders if you’re not going to have penalties for me not following them.”

“Chelsey, I…” Harry shook his head, momentarily lost for words. “That stuff… the spanking. It’s a sex thing. That wouldn’t be appropriate between us.”

The brief fantasy of being taken over Harry’s knee and spanked flickered and died. She had hoped for a different reaction. Chelsey covered her disappointment with her bright smile. “I was only teasing you,” she said, giving him a playful nudge. “Don’t worry. It’s really nice of you to offer to support my studies. Can I borrow your laptop? I want to start doing some research as soon as I’ve finished the washing up.”

Harry breathed an audible sigh of relief. “I’ll do the washing up,” he said. “If you’re that keen to get started, you should get right to it.”


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7 reviews for Challenging Chelsey

  1. Stats23

    I really enjoyed reading this contemporary spanking romance. It’s the kind of love story that you can really sink your teeth into and actually believe how it plays out, every step of the way. Harry had passed by the young beggar girl without so much as a thought until one day when he heard her speak. He then immediately recognized her as the younger sister of his former best friend. Chelsey had lost her entire family due to an unfortunate terrorist attack. Once he knew who she was, he could not pass her by and instead engaged her in a conversation that resulted in him inviting her to come and stay with him while she got her life back together. One thing led to another, in a most believable and endearing way. They both recognized that she needed firm guidance in her life choices with appropriate consequences (!) How their relationship plays out is a joy to read, even with the requisite ups and downs that all relationships encounter. Loving spanking scenes, sensuous sex scenes and lots of romantic support. Etta Stark at her best. 5 Stars.
    I received a free copy of this book via Booksprout and am voluntarily leaving a review.

  2. Ronald

    Chelsey is homeless and wallowing in the unhappiness caused by the loss of her entire family to a terrorist, several years ago. Harry, a friend of her dead brother, sees her and invites her to live with him and get off the street. Over time he gets her cleaned up, and she gradually gets her life in order. In the course of doing so, they develop a relationship and she discovers she is as submissive as he is dominant. It leads to some very entertaining scenes between them. Both characters are likable and develop together as the story proceeds. It was the first book I read by this author and I look forward to reading others. I received a free copy of this book via Booksprout and am voluntarily leaving a review.

  3. Shawn

    Chelsey is shattered, homeless and ill after the tragic deaths of her parents and brother when she was sixteen. Six years later she is all alone in the world living on the street by her deceased brother’s best friend. After a few months of comfort and care she begins to become too comfortable existing with no apparent goals or progress, so Harry implements a plan which leads to domestic discipline. Unexpected romance with plenty of steam take the reader through the process of making her whole again.

  4. Rhea

    ‘Challenging Chelsey’ is about the journey of a young woman finding freedom and strength to grow through submission.
    Even though this is a short and quick read the story has a good foundation, a well executed plot, well developed characters that grow throughout the book and is very well written.
    It reminds us to look past the surface because everybody has a story.
    It is definitely worth reading.
    I received a free copy of this book via Booksprout and am voluntarily leaving a review.

  5. BlueDiamond

    This friends to lovers’ story is a great read with lots of sexy scenes as Harry helps Chelsey through a very difficult time in her life. Harry is strong for her in all the right ways. His dominance brings out a submissive side in Chelsey, a trait she didn’t thing she possessed, in this enjoyable novel.

  6. Marybeth

    Chelsey lost her family at 16 in a terrorist attack. She was unable to cope and she had no one to help her. She became homeless. Harry was best friends with Chelsey’s older brother. Six years later, he recognizes her living on the streets. He brings her home and helps her get better and to start living a life. They fall in love. The journey to their HEA is compelling. I enjoyed this story and hope to read more by this author. I received a free copy of this book via Booksprout and am voluntarily leaving a review.

  7. Jami

    Really enjoyed the characters in this book. A sensitive strong man and sweet submissive who evolves beautifully in the story. I found it refreshing that they both communicate well with each other about their needs. I also enjoyed how perfectly their dynamic fit together. One of the best books I have read!

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