Catching Up With Chloe (DG, Role Reversal, Prost.)

[ArdentOneX]

Incredible story. Keep up the great work. Eagerly awaiting the next chapter.

[r1co7]

an exciting new chapter, now for the events to unfold from your colorful creative mind thank you Grace

[Tara]

Fab new addition as always Grace. Luv it!

[Origami]

Hi Grace,

Well, here we are again, at the end of your latest chapter and tapping my screen to see if theres more story ive somehow missed! Always a pleasure, always happy to see a new chapter, always that sense of disappointment when we reach the end and realise there’s probably a week to wait for the next instalment….loving Jess’s transition. Great work as always.

[GraceFairway6]

Thanks everyone for the kind words - I do really appreciate it, and it's lovely to read that you're all still enjoying Jess' journey!

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18.
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Yesterday morning, the two women had been standing in Jessica’s bedroom, in her nice house in the posh part of the city, and Jessica had been sorting out some of her clothes for Chloe to wear at her interview.

Today’s situation was a complete reverse - Jessica was in her friend’s bedroom for the first time, and Chloe was going to prepare an outfit for her, so she could go out and see what life was like in the forgotten streets and neighbourhoods. The place where Chloe lived, and the place that Jessica was picturing in an almost romantic light.

Chloe called it a shithole, but to Jessica, it felt like anything but. For a long time, she’d been feeling unsatisfied with her lot, alone and bored with her life, but the prospect of going out now filled her with an excitement she hadn’t felt for ages.

Jessica sat on Chloe’s bed, and looked about the room once again. There wasn’t much to it, not really - a double bed with old sheets, a TV in the corner, a dresser and mirror that could really do with a clean, some faded posters of bands they both loved when they were about ten years younger - and the lingering smell of smoke and sex, just like the House of Virtue. Clearly, Chloe had had some fun in this bed, she thought with a smile.

It was strange, but she could really feel herself fancying a smoke. She didn’t need it, of course, but she thought it would complement this growing excitement nicely.

She looked at Chloe, who was hard at work flicking through the clothes in her wardrobe - her muttered swear words suggested that she wasn’t happy with any of the choices, and the way she just tossed her clothes onto the floor casually reinforced that impression.

It tickled Jessica, just a little, the contrast between the two of them. Yesterday, she’d been so careful - even this morning, packing her bag, she was gentle as she folded the clothes for Chloe. Her friend was explosive, tossing outfits about everywhere - and Jessica knew that, whatever piece of clothing she took crumpled from the floor, she’d still look hot as anything wearing it.

“Sorry,” she said over her shoulder, “this is fucking taking forever. Get your clothes off now, Jess, and grab some knickers from the drawer,” she indicated with her head, “and I’ll finally have some clothes when you’re done, I promise.”

Jessica couldn’t help but laugh at her friend’s sarcastic attitude - Chloe had always been able to make even the most mundane activities into pieces of drama or comedy, depending on her mood.

The HR manager pulled open the drawer that Chloe had indicated, and saw a selection of underwear casually thrown about. It was cheap-looking, used - the very thought about how used they were sent waves of excitement through her body. When they first met each other, Jessica treated the idea of wearing Chloe’s underwear as disgusting.

Now, she could hardly wait.

Jessica stepped out of her flats. She lifted her dress over her head - she wanted just to discard it, throwing it away on the floor like Chloe was doing with her clothes - but instinct took over a little bit, and she folded it casually. She placed it on her shoes, and then perched a little on the drawer as she rolled her tights down her legs.

She was down to her underwear, unclipping her bra, and she felt a little sense of surprise. She remembered Sid walking in on them both, and the embarrassment she felt being naked and in a state of undress - none of that. Sure, it was more private, but she still couldn’t believe how cavalier she was feeling.

She didn’t get fully naked, not just yet. She selected one of the bras, an old and simple white number, and put it on first. Then she let the pants fall to the floor, and she replaced them with a white pair with a few mock gemstones on - maybe it was once a pattern, something for someone to look at. Wow, the idea of needing something on your underwear for someone else to look at - before they took them off, at least…

Would this be the stumbling point, she suddenly worried? Jessica was building up her expectations of what Chloe’s life here was like - could the ultimate blow come if it turned out that, in reality, it was just as boring as Chloe seemed to suggest?

No, surely not, she thought.

“How about these?” Chloe asked, holding up some clothes. “It ain’t anything fucking fancy, but it’ll do for a walk around the area, Jess.”

Jessica smiled.

“Those look perfect, Chloe.” She was beaming, an honest smile on her face. “Absolutely perfect.” And then a thought struck her. “Fucking perfect.”

The word still felt a little strange coming from her lips when she was sober, but she was sure she’d get used to it. She didn’t remember Chloe swearing like this when they were younger, after all.

Chloe raised an eyebrow and let a smile creep into the corners of her mouth.

“You’re starting to fucking get it, Jess.”

She passed her friend the clothes - a simple black top and a light grey tracksuit. Jessica could never imagine wearing something like this in her everyday life, but she was very excited for it - this was far from her normal life, wasn’t it? She pulled the top over her head, and slipped on the cheap plastic trousers and jacket. It was a weird fit, loose at the extremes but form-fitting in all the right places, somehow looking trashy and sexy at the same time. That look she had started to associate with Chloe, and the look she hoped to master while she was here.

Chloe handed her head some scuffed trainers and socks, and she put them on. The shoes were dirty, the treads faded through use, and Jessica wondered where they had taken her friend in the past.

“I think your make-up’s fine for now, and I fucking love the ponytail, Jess. I’ll show you a few tricks for the future, though, and that’s a promise.”

Chloe laughed, and Jessica felt her heart flutter a little. She was still looking at her reflection, and she loved what she was seeing - the idea of Chloe helping her look even better was a very exciting one.

“Right, you wanna make a move?” she asked.

She did, she really really did.

“Yeah,” Jessica replied, “let’s do it.”

Chloe left the wardrobe open and the clothes on the floor, and she led the way from the bedroom. It was a little too warm to wear a coat, but Chloe told her friend that she could lend her one if she needed one. She did offer Jessica a smoke, and the brunette took one from Chloe’s packet. They lit up, had a drag each, and got ready to leave, Chloe slipping on some flats by the door as she held her cigarette in her lips.

She turned, opened the door, and she stopped in the doorframe. Her form seemed to sag slightly, and she turned back to a worried Jessica.

Chloe looked a little guilty: “Jess, I need to tell you something.”

“Oh?” She was increasingly worried now - she wasn’t used to Chloe sounding serious.

“It’s about the job - the phone call I took earlier. They offered me the job, like you said they would, but there’s a catch - I’m starting tomorrow. I knew it was a fast turnaround when I went for the interview, but I never thought it’d be that fucking fast, you get me? And we had this deal - I was gonna look after you here, and I can’t do that if I’m out all day at work, can I? Fuck me, Jessica - fuck me.”

Jessica smiled, and placed her hand gently on Chloe’s shoulder, calming the annoyed woman.

“Chloe, you have to go for it. Don’t worry about me - I’ll get by, I promise you. I can look after myself - I know my way around, and you can tell me what to do to get by. This will work, and it’s great, Chloe, because you get to follow your dream too.”

Chloe smiled a little, but her eyes still offered more than a hint of annoyance - she wanted to be part of this journey with Jessica.

“If you’re sure?” she asked. “Because I can just blow the thing off if you want? I’ve no problem with fucking off out of there.”

Chloe laughed, but Jessica was quick to shake her head.

“No, goodness no, I can’t let you do that, Chloe. Really, I’ll be fine, I promise. I’m not giving up on this, but that means you can’t give up either. Got it?”

The blonde girl smiled.

“Yep, I’ve got it. You’re the best, Jess.”

She hugged her friend.

“We still have today though, don’t we? So let’s make it a fucking good one!”

[Daddy]

I Love the fact that Jess is pushing Chloe to her old life while Chloe is actively trying to stop Jess but doesnt mind helping her either their friendship is actually genuine as it appears to me for now hope to see Chloe more becoming the model high class women and Jess living a life a life of low life in a trash place and enjoying every bit of it.

[GraceFairway6]

They're been a big delay, and I'm sorry about it, but I'm back with a new instalment - I hope you enjoy it!

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19.
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In another life, Chloe’s estate in the rough part of the city was not a place Jessica would ever have found herself in. And if she ever ventured here, she would be keeping her head down, hoping not to make any waves and to return to somewhere more familiar as soon as she possibly could.

She remembered feeling like that when she was here that first day, wearing Chloe’s clothes in the desperate hope that she would find her friend. That was the day she first visited the House of Virtue, and when she first got a real glimpse into what Chloe’s life was like.

The day, she realised, that she started to really take stock of how discontented she was with her own life.

It couldn’t have been more different today, however.

She and Chloe wandered down the street, dressed in similar tracksuits - Chloe an excited guide, Jessica a more-than-keen listener, taking in all the sights and the sounds and making sure she knew everything about this place. She listened as Chloe pointed out where the shops were, and the shortcuts, and the routes that you definitely had to avoid unless you were asking for trouble.

“What kind of trouble?”

Chloe seemed a little tickled by her friend’s naivety: “Drugs, crime - I knew a girl who got assaulted by some asshole there, off his head on bad shit. Don’t get me wrong, Jess, it doesn’t happen a lot - down here, we know how to look after ourselves, and if you know that, then no-one fucks with you. But take some advice, okay - don’t fucking push it.”

Jessica nodded at this warning.

“You want a fag?” Chloe had the pack in her hand. “All this walking is fucking knackering me, Jess - I could do with a smoke.”

Both women had lit up, and after a couple of drags, they continued the walking tour of the area. Chloe was meandering, making comments and saying hello to random people that they’d passed in the street, but Jessica could tell that she was wandering with something in mind. That was the thing with Chloe that she’d come to realise - no matter how scattered or random Chloe appeared to be, she normally had some objective in mind, and she wouldn’t stop until she got what she wanted.

That was one of the secrets of their friendship, Jessica thought as she took another drag - Chloe was determined, and she was normally happy to go along with what her friend wanted. Some of the things she’d done these past few weeks, she’d done them because Chloe had wanted her to.

She thought that, and then she wondered - was she just using that as an excuse?

They kept walking, Jessica listening and thinking.

And soon, they were at a familiar building, and one that Jessica was starting to know all too well - the House of Virtue.

“I hope you don’t mind,” Chloe said, apology in her voice, “but I need to nip in quick, tell Sid I’m fucking off for a while.”

“You go ahead, Chloe.”

“You wanna wait out here, or come in?”

Jessica went to respond, but she was struck silent with uncertainty - she honestly didn’t know. It was an awful place, run by that dreadful man, and she was thrilled that Chloe was getting out of there and so soon. And she remembered what the place did to her - every time she was there, she had thoughts that she’d never believed she could. She’d thought about doing things she’d never have believed she wanted to do, and yet, in that building, things were different.

She’d listened in on sex, and imagined herself being the one getting fucked. She’d dressed in skimpy outfits, and realised that she looked amazing when she did. And she’d been presented with Sid’s cock, and she almost got on her knees and started sucking it.

Because she was told to.

And because, deep down, she’d wanted to.

“Earth to Jess,” Chloe interrupted, “what are you doing? You coming?”

Now or never time, Jessica thought - it was nothing to Chloe, but it felt like a giant step to her.

“Yeah,” she said, “I’m coming in.”

It was her choice, she knew, and somehow that little action in itself felt empowering to her. For the first time, she wasn’t entering this building in search of Chloe, no - she was doing it because she wanted to.

Chloe finished her cigarette, and she tossed it to the ground, not even bothering to stub it out with her foot. Jessica did the same, copying her friend’s example - she hoped to be doing a lot of that while she was here.

As always, Sid was sitting behind that desk, as if he was waiting for them. He was clad in a grey tracksuit, and wearing that giant smarmy grin - one that widened when it saw Chloe, and somehow widened even more when he noticed that Jessica was with her.

“Crystal,” he said, “and Jess, my favourite.”

“Fucking charming, Sid,” Chloe laughed.

“What brings you both to my little house of entertainment today, my darlings? Was the allure of Sid too much for you to handle in the end, Jess - you made Crystal here bring you right on back?”

His eyes met hers, and she wanted to blush a little.

“Piss off, Sid,” Chloe butted in, and Jessica felt the urge to contribute too: “Yeah, piss off, Sid.”

He seemed amused, as always, and although Jessica didn’t see it, Chloe raised an eyebrow in surprise.

“Wow, darling,” he smirked at Jessica, “I didn’t know you had fucking claws.”

He laughed at his own joke, before reclining in his chair.

“Well, if you haven’t brought your lovely friend to come see me, Crystal, what do you want? You ain’t meant to be working today, are you?”

“You know I’m not, Sid,” Chloe folded her arms. “He plays it coy, Jess, but he knows everything, Sid does - he acts like a fucking idiot, but he’s sharp as a tack.”

Sid smiled at the compliment, and he teasingly blew Crystal a kiss.

“It’s true, darling,” he looked to Jess, “spend some time with me, and I’ll blow you away with my intellect.”

Jessica knew she was blushing now - and with the glint in Sid’s eyes, she knew that he could see it. In response, she just stuck her hands in her tracksuit bottoms and looked to Crystal.

“I’m sorry, Sid, but I’m not likely to see you for a while - I’m off. I’ve got a new job.”

Jessica wondered if this would be the thing to finally knock a smile off Sid’s perma-smiling face - but if it bothered him, she didn’t see it.

“Really? You’re fucking off and leaving me, Crystal?”

Chloe nodded her head: “You knew I wasn’t hanging around here forever, didn’t you? No, I’m off tomorrow - I’m moving up in the world, Sid.”

Sid shrugged his shoulders.

“Yeah, I guess I knew this day was coming - none of my best ladies ever stick at it all their lives. But do you have to fuck off right now? I mean, I’ve got you down to work half the week.”

“Out of my hands, Sid.”

But then, a thought seemed to strike her. She looked at Jessica, an idea seeming to form in her mind.

“Or maybe I don’t have to, Jess. I mean, I’m only doing nine to five, right? So I can do that in the day, come here in the night - I don’t need much sleep, and it’s double the fucking money.” She looked to Sid. “You know what - we might make it work.”

Jessica stepped in, grabbing Chloe’s shoulder.

“Can we talk a moment, Chloe?”

“Yeah, shoot.”

Jessica noticed Sid to her side, sitting comfortably and looking at the two women.

“No, I mean, in private.”

He raised his hands in mock surrender.

“You want a side office, darling, you go and take one - you know the place, don’t you?” He flashed a toothy grin at her. “You’re here so often, Jess, you’re practically a regular.”

He started laughing at his own comment - Jessica started walking, and was surprised that she could remember the way like it was second nature.

Chloe followed her to the office room that Jessica had sat in that first time she ever came to this building. It was as Jessica remembered it - still dark and miserable, the sound of music still muffled but pressing on the room’s ceiling.

Jessica sat on the desk, and looked at her friend.

“Chloe, you can’t seriously be thinking about this, can you?”

“Why not, Jess?” she smiled. “Think of the money I’d make with two jobs.”

“Fuck the money, Chloe,” Jessica snapped before she realised. “Think of your reputation, Chloe. You’re about to start a professional career, the first steps to a new life, and you want to come here and dance and fuck in the evenings? It’s a really bad idea, Chloe, trust me - all it takes is one person you meet in the office to recognise you, and then what?”

“Jess -” Chloe started, but the brunette cut her off.

“Chloe, I need you to listen to me. You’re my friend, and I care about you. I… I want you to have the chance that I did, to make something more of yourself. I know you love this job, I really do, but it’s like Sid said - you can’t do this forever.

Chloe nodded, understanding Jessica’s point, but the HR manager detected a hint of hesitation in her friend’s eyes. She’d seen it before in her line of work, and she’d grown to recognise it - people torn between what they wanted to do, and what they knew they should do.

Jessica had a moment’s doubt herself - fuck, how amazing was this job if Chloe was so torn about giving it up? She knew she loved her own work, but if a better position came along, she’d leap at the chance to move up the ladder.

So why wasn’t Chloe?

Jessica remembered her friend’s passion that first night, when she talked about how she fell into that line of work, and how amazing it had been. Sure, Chloe said that she wanted to be like Jessica, and Jessica truly believed that - but it was always so hard to leave a job you loved, and it was clear that it was weighing on the blonde woman.

“I shouldn’t do it, should I?” Chloe asked, her voice still uncertain.

“You’ll thank me later, Chloe, I promise you.”

Jessica, just for a moment, wondered if she believed her own words.

Two uncertain women returned to the front desk, where the ever-cocky Sid remained seated.

“Aw, I missed you,” he teased. “So, you’ve had your little tete-a-tete, as the French say - and what have we decided?”

Chloe looked to Jessica, and then back at Sid: “I’m not gonna do it, Sid. I’ve got this new job, and Jess says I need to focus on it.” She paused, and then spoke with a little crack in her voice: “I’m sorry.”

Sid nodded once, and shrugged his shoulders.

“You’re breaking my heart, Crystal. I mean, I can’t be done with you soon, but you’ve got bookings, clients, shifts - I can’t just let you walk off now, you understand?”

“How long do you need, Sid?” Chloe asked.

He made a show of looking at his phone.

“You’ve got three weeks down, Crystal. I mean, I could cancel all the bookings and shifts, couldn’t I,” he smiled at her, “but you know the policy here. You fuck off, you cover the money I lose when you fuck off.”

Jessica saw Chloe’s eyes open a little in shock. Clearly, that would be a lot of money - certainly enough to give Chloe something to think about.

The blonde woman looked at Jessica.

“I could do three weeks, right?”

He was winning her round, with charm and threats in combination - Jessica couldn’t let him steal this fresh start from her friend.

“No, you can’t. If you do this, Chloe, there’s always going to be one more shift, one more client, and you’ll be doing this forever. You need to get out now, okay?”

“Fine by me,” Sid chipped in, “just let me start totting up the bill, alright?”

“Fuck off a moment,” Chloe said, and then she cut off Jessica too, “you fuck off too. I need to think. I need to figure this out myself.”

Jessica recognised the expression on Chloe’s face - she was going to give in.

“Chloe, don’t,” she started.

“Let her do what she wants, darling,” Sid offered.

“No,” Jessica butted in, “you shut up.”

Sid laughed.

“It’s an easy choice,” he said.

“Jess, I don’t know…”

“You do, Chloe,” Jessica urged her. “Trust yourself.”

“Finish your shifts, or pay a load in compensation - the choice is easy, Crystal. So easy.”

“I’ll do them.”

Silence fell over the three of them, as they were all stunned by the words that had escaped from Jessica’s mouth.

“Leave her alone, Sid,” Jessica said, “and I’ll cover her shifts, okay. Does that work for you?”

His smile more than answered that question.

[Daddy]

This was a great addition it's quite fascinating to see How Jess while losing her own values and decency is imbibing those same values in Chloe trying to even cover her career from being screwed up.

[dude791]

Great story! Can’t wait to see her going down further and the physical transformations take place. I hope Jess is unrecognizable in the end. Even to Chloe.

[Bs1974]

Loving this! The small seeds planted here and there, Jess “volunteering” this, cannot wait to read the rest of her upgrades / downfall! Thanks for this amazing work again Grace!