Work Hard Play Harder Ch 19

Copyright © May 2025 by CiaoSteve

CiaoSteve reserves the right to be identified as the author of this work. This story cannot be published, as a whole or in part, without the express agreement of the author other than the use of brief extracts as part of a story review.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.

Author's Notes

This is a nineteenth and final part to the series. Although it is self-contained from a story perspective, I would recommend you read the earlier chapters as there will be references which make more sense if you have read the earlier parts. Please note, this is a mixed genre chapter with a mix of anal, lesbian and BDSM. Hopefully there is something for everyone, but I thought it was worth pointing out just in case.

* * * * * * * * * * * * * * * *

Alone again, in the privacy of her mistress' en suite bathroom, Kirsten found herself gravitating towards the toilet once more. It wasn't so much that she needed to go--Kirsten had spent plenty of time doing just that, as she relieved herself of her enema--yet still she felt she had better try just in case, especially if her next step was to be getting filled once more.

It was as she sat there, that Kirsten started to ponder about what she had been told, and what it might just mean. It wasn't so much what her mistress had said about fucking the young blonde's ass. That, much as it thrilled and scared Kirsten in equal measure, was old news. What now occupied Kirsten's mind was the idea that she might get lucky, and the suggestion that there might just be a chance of having two for the price of one.

What exactly did Claudia have in mind?

Would they both be fucking her ass?

Would it be one after the other?

Would it be both together, stretching her even wider?

All the time, as she mulled over the various connotations of that throwaway suggestion, Kirsten tossed the plug over and over in her hand. It was metal, stainless steel to be more precise, but it was so different to the one she had worn on that first meeting with Sophie.

For one, it was big, ever so big, with a shape more like a cylindrical torpedo than the traditional teardrop bulb. Kirsten tried her best to estimate its size using the length of her finger as a guide. It was no exact science, but she came up with an insertable length of about four inches and a girth of... Kirsten gasped. No... no... she must have been wrong. She measured again and came back to the same estimate. The girth wasn't so far off five inches, maybe a little less, but really not that much. Then there was the weight. Kirsten was never a good judge of weight, but it must have been a couple of hundred grams to say the least.

If that wasn't enough, something else grabbed Kirsten's attention, something which literally confused the young blonde, and that was the base of the plug. As expected, it flared out, with a narrow stem linking base to bulb. The difference though came in appearance. Where the one she had used before was jewelled, even to the point of being pretty, this one was rather plain in comparison. Yes, there was a touch of decoration in the form of a couple of rubber rings going around the edge of the base, but otherwise it was just solid metal.

It seemed this plug was all about function rather than form, more to be used than to be seen. When it came to being used, that was the other thing which confused Kirsten. In the flat end of the base, there were two holes, one dead centre and another over towards the edge. Kirsten was still pondering their meaning, when a call from downstairs broke her out of her contemplative state.

"Lunch is ready, Kirsten," Claudia called out.

Kirsten jumped up off the toilet. She hadn't needed to go, which was a relief, but that sense of relief was now overtaken by a more pressing need; a pressing need to get a move on and get back downstairs. Suddenly there was haste in her actions. Rummaging in the bathroom cabinet, Kirsten found just what she needed. The only question now, was where and how to get on with the job in hand.

The answer to that question came back in the bedroom. Kirsten carefully placed first the plug, then a large pump bottle of lube and finally a handful of tissues out atop the duvet of her mistress' bed, then settled herself down close by. She took to lying on her side, leaning forward ever so slightly with her uppermost leg raised as far as she could towards her stomach. She reached back. It was a stretch, but it would have to do.

What followed was a bit of a display of contortionism as the young blonde lubed herself up. It was a little to start with followed by a single finger up against her rosebud. She rimmed her opening. She pressed a bit firmer, willing her finger to sink inside. All the time, Kirsten was met with resistance, yet never did she give up. Kirsten went back to the bottle, applied just a little more lube to the tip of her finger, then reached back for her ass once more. She repeated the same two or three times. Finally, with a stifled gasp from the young blonde, her tightness started to wane, and she dipped that finger up inside.

It was a strange sensation. It always had been, a bit like she was pooing but all in reverse. It was strange, but somehow it was pleasureful, and Kirsten couldn't help herself but withdraw her finger, add another dash of lube, and try again... and again... and again... and the more she tried, the more she relaxed, and the more she relaxed, the more she enjoyed. It was a far cry from anything she had done before, but once again, just like earlier in the day, there was something satisfying about that feeling of a finger up her ass.

A finger was one thing, but that plug was something else, and didn't Kirsten know it. Before long, one finger, along with even more lube, had become two, squeezed up inside her tight little ass. She probed deeper. She eased the two digits apart within her opening. All the time the young blonde tried to stretch herself out, making herself feel ready for what she knew was to follow. She thought about a third finger, but the awkwardness of her position was just too much to get the angle, and Kirsten resigned herself to the obvious.

It was now or never.

Kirsten reached first for the lube, applying a large dollop of slickness to her fingers, then easing the same into her opening. The plug was next, getting a similar treatment with a copious amount of gel applied across its surface. Reaching back, she positioned the tip against her rosebud, shivering slightly at the coldness of the steel.

Kirsten held her breath.

Kirsten bit her lip as she started to work the plug.

She could feel the stretch down below as the torpedo-like bulb widened out. At first it felt fine, that feeling of fullness against her opening, but before long the stretch took on another dimension, a more uncomfortable dimension. Whatever she tried, it was to no avail. Stretch she might have done, but take this monster wasn't quite on the cards, at least not yet. Kirsten though wasn't about to give up.

A little more lube...

A little more with those two fingers, finally straining to add the third if only to mimic the girth of that mighty toy...

And then... then...

Kirsten picked up the plug once more. She positioned it against her opening and pushed.

Again, she could feel the stretch.

Again, she could feel the resistance.

This time though, the young blonde didn't stop. For a moment, she took to just rocking the plug against her opening, feeling the stretch build then release. It was as she held it there, rocking the tip in her opening, that Kirsten did something more. She added a little more pressure with each forward movement and, as she did, she rotated the plug ever so slightly.

Ever so slowly, the stretch continued...

Ever so slowly, she felt the plug widen out in her opening...

Ever so suddenly, the stretch gave way to another feeling, a feeling of satisfaction as she welcomed the plug deep into her back passage...

It was just in time. No sooner had she felt her sphincter contract around the neck of the plug, than there was a second call from downstairs, a more direct call for Kirsten to get her ass down there pretty pronto. With a quick wipe to remove any excess lube, Kirsten jumped up off the bed and instantly regretted it.

Kirsten hadn't thought too much about it when inserting the plug, but now she was standing, her mind was consumed with a different feeling, one of fullness and one of heaviness. It was only as she stood, and tried to take those first few steps, that she realised just how big the plug was, and just how awkward it was going to be to make her way downstairs, at least to make it down and keep any semblance of dignity.

Still though, still that's what she did. Her movements were slow and rather predetermined, but she made her way over to the stairs and started her descent. As she took those steps, one at a time down towards the other two women, her mind flashed back to that very first time with Claudia. Back then it had been a pair of jiggle balls in her pussy which had left the young blonde in a bit of a state, and now it was one humungous plug. All Kirsten could think was... is that what you called progress?

"Ah... Kirsten," Claudia announced, seeing her young sub heading over towards them. "Come... take a seat, and let's eat."

"Yes, Mistress... thank you, Mistress," Kirsten replied, her gaze transfixed on her mistress as she followed Claudia all the way over towards the dining table, in a repetition of what had played out the day before.

Kirsten paused for a moment next to her designated seat. She pulled the chair out, all the time wondering if she would find something affixed to its surface again this time. Much to her relief, she didn't. It was just a plain old chair, no surprises, no hidden torments, most definitely no waiting toy.

Slowly, carefully, Kirsten lowered herself down onto the wooden seat. As she did, she gasped, the sound something akin to a tiny, stifled squeal. There was no dildo affixed to the chair, so that couldn't be blamed for the young blonde's outcry. What was to blame was the sudden pressure against the base of the plug and the way it sank just a little deeper inside.

"Is everything okay, my darling?" Claudia asked.

Kirsten didn't reply. She just looked at her mistress, a look of disdain on her face.

'Really, Mistress! As if you need to ask!' Kirsten thought to herself.

* * * * * * * * * * * * * * * *

Lunch was a light affair. It wasn't so much a time for eating--for some reason nobody had much of an appetite--but more a chance for reflection.

The need for reflection was no surprise, and it was much needed, for Sophie at least. The events that morning had taken her somewhere well out of her comfort zone, and it took a little getting used to. What Sophie needed, and what she got, was the reassurance that nothing was held against her. Her time at the cabin had been a bit of an eye opener, in more ways than she had ever imagined, and top of that list was probably a certain young blonde, or more so the behaviour of that young blonde.

All Sophie could do was stare back at Kirsten, watching, listening, taking everything in. To say she was in awe of the young woman sitting opposite her was an understatement. For all Kirsten had been through, it was like the young blonde had taken everything in her stride, never flinching, never protesting, simply accepting, and gratefully receiving.

Was this for show, to make Sophie feel better? Somehow, Sophie didn't think so. There was nothing artificial in the relationship between Claudia and Kirsten. What Sophie saw between the two of them was nothing more than love, an unconventional sort of love, but love, nonetheless. It was exactly what Sophie imagined of a mistress and sub relationship. What's more, it was exactly what Sophie wanted to understand better.

Kirsten was everything Sophie wasn't.

Kirsten was much of what Sophie felt she wanted to be.

Sophie could have had so much to envy about Kirsten and the life Kirsten had, but she didn't. As she sat there, all Sophie could think about was how much she could learn from the young blonde if given the opportunity. Did she regret coming to the cabin? Not at all. Sophie's only disappointment was that the weekend seemed to be flying by, all too quickly. Before she knew it, it would be time to climb in her boss' car and head back home, immersing herself back into her normal life.

What followed was almost like Claudia could read Sophie's mind. From nowhere, Claudia tossed out the very question she had asked earlier that day, out on the balcony, as they finished off breakfast.

"So, my darling Sophie... what are we going to do with you?" Claudia asked.

For a moment, Sophie thought about what had been asked, and whether she should be answering or not. The tone suggested question rather than command, and the way Claudia looked at Sophie seemed to be looking for a response.

Sophie smiled.

"You're going to have me fuck Kirsten's pretty little ass," Sophie replied, moving her gaze from Claudia and towards Kirsten. "That is... if you still want me to fuck her ass."

This time it was Kirsten who smiled. The smile wasn't so much for the suggestion of getting her ass fucked; she was well and truly up to give that a go. The smile was more for what had been said afterwards. Yes, Kirsten had noticed the way her young charge hadn't just rushed in and tried to grab her opportunity but, instead, had asked if it was still required. The only question now was whether Kirsten should be the one replying, or whether her mistress should do the honours.

That question didn't take long to be answered.

"You bet I do," Claudia replied. "And from the smile on her face, I reckon Kirsten can't wait to get that pretty little ass of hers fucked either. Am I right, Kirsten?"

Kirsten simply nodded. She still didn't know what it would be liked to get her ass fucked, but if it was anything close to the feeling when Sophie used her finger on Kirsten's virgin rosebud, then she couldn't wait to find out.

The only one having doubts now, was Sophie.

"But... how?" Sophie asked, realising she didn't have anything much to fuck that pretty little ass with, other than her own fingers, and if the intention was to use her digits, wouldn't the ask have been to finger that pretty little ass rather than fuck it. "I don't exactly have one of those... what did you call them..."

"Strap-ons?" Claudia interrupted. "Don't you worry about that... just you come with me, my darling Sophie, and we'll soon have you looking the part."

As Claudia spoke, she stood up and walked around to where Sophie was sitting. She held out a hand and waited for her guest to take it. Then, all the time holding hands, Claudia led Sophie over towards the stairs, before heading upwards. It was with the two women halfway up that Claudia called down to Kirsten.

"Give us a few minutes, Kirsten... then come and join us... we'll be in your favourite bedroom," Claudia said.

And then they were gone.

Kirsten sat there, mulling over what had just happened and what she had just heard. Once again, the way the two women had headed off upstairs brought back memories, of the time she led Sophie upstairs the day before, and of that very first time when Kirsten herself had been led. Kirsten could see the sense of excitement in the way their guest followed her mistress and could almost imagine the way that excitement would be tinged with just a touch of trepidation.

The more she sat there and thought about it, the more Kirsten started to question herself. Was she really imagining the feeling of their guest or was Kirsten actually reflecting on her own emotions. It was one of the main reasons she kept coming back. That sense of nervous excitement never left her. Kirsten just loved the thrill of the unknown, trusting in others, hoping they'd take her back to that special place. She had felt it so many times before and, for sure, she was feeling it once more as she thought about what had just been said.

Leave it a few minutes. Well, that was an easy one, and for some reason the number seven kept coming back into Kirsten's mind, although she wasn't sure she could wait a whole seven minutes. As for her favourite bedroom, now that was a question and a half. To date, she had shared three bedrooms with her older lover, and each was special in its own way. Okay, so they weren't at the apartment in the city, which narrowed down the options, yet still the two remaining bedrooms held such pleasant memories.

Kirsten would have been hard pushed to say that one was more special than the other nor that one could really be deemed her favourite, yet, deep in her subconscious, there was only one which seemed appropriate, the one with the largest bed. It was the bed which really filled her mind; the bed she had been bound to on multiple occasions, the bed she had cum so hard atop, the bed she had allowed their guest to spend the previous night in, all alone, with nothing to do but think about being at the cabin.

Taking a punt, it was towards the guest bedroom, that Kirsten finally made her way.

* * * * * * * * * * * * * * * *

Where Claudia and Sophie had bounded up the stairs enthusiastically, Kirsten was a little more controlled in her movements. It wasn't that Kirsten wasn't enthusiastic--if truth be known she had that feeling back inside, the one which told of excitement and trepidation in equal measure, the one which had her stomach doing cartwheels such were the nerves--but more a consequence of the little extra she carried inside.

Every step was an awkward affair, providing an instant reminder of the size of the plug, and the way it filled her ass.

Every step, every movement inside, had Kirsten feeling just a little more aroused.

Every step had Kirsten imagining just what it might feel like to get her pretty little ass fucked.

By the time Kirsten reached the top of the stairs, she could hear the other two women from within the guest bedroom, despite the door being part closed. Slowly, careful not to make a sound, she crept across the landing, drawing to a halt just outside the bedroom. She held her breath, for fear of being heard and, like a peeping tom, peered in through the gap between door and frame.

'My god... what the fuck!' Kirsten thought to herself as she stood there watching attentively.

What caught Kirsten's eye first?

It had to be Sophie, standing there with her back to the door, still totally naked. As Kirsten watched, Sophie leaned forward and reached down for something on the floor. What a sight; long deliciously tanned legs, the cutest pert ass, and the smile of those lips as they came into view. Kirsten could have stood there all day admiring the view, or at least she could have if it wasn't for something else catching her eye, something rather familiar.

Whether Sophie knew she had an audience or not didn't seem to stop the young woman. If anything, she was more preoccupied with what lay on the floor in front of her than she was with the part open door. Carefully, she picked up the black leather garment and held it out in front of her.

"This way round," Sophie commented, holding the harness up with its triangular codpiece away from her.

If there was a response, it was a silent one. Kirsten, as she stood there watching, wondered if Sophie was all alone or not. Then another thought crossed her mind. If Sophie was all alone, then who was Sophie talking to? Surely, Sophie wasn't talking to herself. Or maybe--Kirsten could admit to having done the same herself--maybe Sophie's words were rhetorical, spoken by Sophie with no other purpose than for Sophie's own moral support.