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A much needed change (Floss88 x lasciel)

What she had meant was simply for him to leave himself easier to access by one of her wandering hands. But the distinctive sound of a man masturbating caught her attention and held it enough that she would've drifted lanes had the autopilot not been engaged. Catherine hadn't told him to touch himself, but at the same time, she had given him permission to do such earlier and never rescinded that. Or perhaps he simply misinterpreted her words.

Not that she minded. As likely as not she would've pushed him to that point anyway.

She unwrapped one manicured hand from around the wheel again and leaned over, tracing her nails over the tip of him when he was at the bottom of his stroke, then planting her thumb more firmly and rubbing.

"Don't even think about making a mess in my car, Sam."

The angle at which she reached precluded bringing her thumb to his mouth so she brought it to her own, licking the pad of the digit clean with one exaggerated swipe of her tongue before wiping it against her shirt. She tapped a few things on the dash to bring the music back, signaling that she was done talking with Sam as a beat track started up that made the whole cabin buzz and thump. A female voice monologuing about her life and wealth overlaid the beat as Catherine reclined into her seat and adjusted her grip on the wheel, looking smug and utterly satisfied as she drove through Friday evening traffic towards the suburb of Sofia with her rival frustrating himself at her command in the seat besides her.

---

Fifteen minutes later she'd exited from the highway onto a freeway, and a few minutes after that they waited at a light off the exit to make the turn onto the busy main boulevard that would lead onto the promenade as they approached the water.

"You can stop that now and put it away. I'd rather not get a ticket for public indecency."

Heedless of whether he'd succeeded in making himself decent again she turned when the light went green, and a few minutes after that they had turned off onto a side street paralleling the main one and pulled up to a garage entrance that she had to coax the car into activating. Down they went then, three layers deep before pulling into a parking spot clearly designed for a far larger vehicle. Catherine's Tesla was the smallest vehicle on display, dwarfed by the SUVs that were the majority occupants in the underground space.

"Don't dawdle," she muttered to Sam as she shut the car down and stepped out from her seat, pausing to open one of the rear doors and grab her bag before heading towards the elevator. Only if she didn't hear her companion follow did she turn back and glare expectantly, hand on one hip.

Thankfully their trip upstairs bypassed the lobby entirely, straight up to the tenth floor of the fifteen-floor building. Nobody was around to see them as Catherine strode confidently down the hall, heading to the western face of the building to unlock a door as unremarkable as any other in the building that was nonetheless set into the end of the hall rather than the side.

"Will you walk into my parlor?" She asked when she'd unlocked the door and opened it, stepping just barely inside the foyer to give Sam room to pass by her.

Catherine's apartment was large and light-filled, emphasizing elements of green velvet and bronze accents. A spacious living room continued out onto a balcony that overlooked a few rooftops and the water beyond, with a dining table to one side delineating the space from the open-plan kitchen with ample prep space and a six-burner stove and stainless-steel fridge. Doors led off from the main space into two bedrooms, a guest bathroom, and various closets. The space was clean and tidy but felt more lived-in than the sterile corporate apartment they'd last interacted in; a few postcards were stuck to the fridge with magnets, a mug of coffee used that morning sat in the sink and a dirty pan with remnants of egg on the stove, a copy of The Financier lay open on the coffee table, turned to an article on recent movements in the Chinese steel market. The pillows on the couch weren't perfectly fluffed but had likely been lounged on since the housekeeper last visited, there were a few black marble coasters spread over the table, and if he crouched down he'd find a few strands of long red hair beneath the couches or in the corners.

"Want something to drink? Restroom is through that door," she remarked as she continued inside, gesturing to a door before dropping her bag on one of the livingroom's matching velvet chairs. Moving to the kitchen she washed her hands then pulled out a glass (or two, if Sam had requested something) and moved to the a glass-faced cabinet in the living room sporting an impressive collection of whisk(e)ys.

Pouring something for herself (and Sam if he'd asked) she continued back to the coffee table to set down her glass(es) down on (a) coaster(s). "You spend much time in Sofia?" The city's name was technically Santa Sofia, but nobody who lived there called it that. "I do recall you asking me to show you around a few months ago. I suppose you're getting your wish, in a fashion."
 
Sam hurried to, pack himself away as it were, the ever-present threat of being spotted more than enough to make it an anxious hurry no matter how turned on he might be. He had a carefully cultivated self-image, which Catherine had taken a purple sledgehammer to, but more than enough of it was still intact for him to be a little horrified at the prospect of even been seen messing with his pants in public.

He was still fiddling with his belt as Catherine got out of the Tesla, attempting to tuck his hard cock out of sight. It was ultimately futile and he ended up holding his laptop bag in front of him awkwardly, bringing up vague unpleasant memories of early puberty. At every stage Sam felt behind, on the back foot, hurrying to catch up with Catherine as she headed home.

"Happily Miss Jones." Sam didn't know what he had expected, a lair of some description perhaps? Chains hanging from the ceiling? All absurd of course, the tastfully decorated apartment, with the outstanding view was far more reasonable. And it was lovely, the used pan on the stove seemed incongruous somehow like he couldn't imagine Catherine having a single thing out of place. It was ultimately the apartment of a real human being, not that that did anything to diminish the control of her rules and her presence.

Sam placed his laptop bag by the door and stood in the middle of the room awkwardly.

"Yes, thank you Miss Jones." A drink was exactly what he needed. He found this easiest when there was no stopping when he was having to run just to keep up. When he didn't have time to think, now he caught himself idly drumming his fingers on his thigh as she poured drinks.

Hesitantly he joined her, sitting in the chair opposite Catherine. She hadn't told him to sit but it felt implied, he wasn't sure if he was supposed to ask before he did anything or if that would make him tiresome and irritating. This was the problem, time to think.

"I can't say I have Miss Jones, before the case I hadn't visited at all and frankly I've spent most of those reviewing documents in the hotel or in the hotel bar. I haven't seen much of Sophia but it does seem to be a beautiful city and certainly more pleasant to be in in winter. I was looking to be shown round Miss Jones, though as you say not just that. As you say I suppose I am getting my wish... after a fashion" he took a long sip of the whiskey, absolutely what he needed.
 
After a fashion was such an understatement of the situation that Catherine couldn't help but laugh quietly into her drink. Yamazaki 18, neat, for both of them; she wouldn't ever let it be said that she served inferior whisky to her guests/friends/enemies (even if she'd actually managed to snag the bottle at near-to-MSRP during one of her trips to Nagoya).

Catherine let him sit and stew for a few more moments as she savored her alcohol, her gaze drifting towards the balcony where the sun was dipping low over the western sky. She could hear his fingers tapping, and imagined his heart thudding against his ribs in similar time.

"You seem tense, Sam." She said as she looked back at him. A sly smile split her face.

Without giving him a chance to remark she stood, setting her drink on the coffee table and striding 'round the furnishing with intent. Leaning over she took Sam's glass as well and set it aside, before placing each hand on either armrest of the chair to bar him in as she loomed over him, bringing her face to hover above his.

"Would you like some help relaxing?"

When he affirmed, with a nod or with his words, her tone grew sharp.

"Take your fucking pants off, Sam."

Catherine pushed off then without another look, and made her way to and through her bedroom door, closing it behind her lest he get ideas about following.

She returned a few minutes later with a towel, a disposable glove, a bottle of lubricant, and a small square black box still in the manufacturer's shrink-wrapped covering. Sitting on the couch she spread the towel over the spaces to her right, then looked at Sam and patted the covered cushions.

"Come here, hands and knees. Now."
 
The whiskey was probably excellent, it was wasted on Sam in this moment at least. While he tried to sit as calmly as if he was merely enjoying a quiet drink with a colleague, he struggled to focus, still hard and tapping a staccato beat on the side of the glass with his index finger. He was drinking the whiskey but he but he couldn't focus on something like taste. He felt like he was waiting for the other shoe to drop for all this veneer of normalcy to be whipped away like the table cloth in a magic trick.

The feeling only grew as Catherine stalked around the room like a panther, plucking the glass from his hand and leaning in close. As she loomed over him, he sank slightly in his seat to better look up at her. Catherine really was beautiful and though he spent much time looking down and away from they her eyes were the most spectacular shade of green.

"Yes?" Sam tried unable to keep the tentative question from his voice. Relax? Yeah he was finding it a tad difficult to relax, as he had absolute no idea what was coming next. When har voice hardened into a command he almost did relax, at least mentally, as his hands hurriedly fumbled for his belt. It was easier when he didn't have to plan or worry about what this might mean, he just had to obey.

Her commanding done was like a hard wire strait to his cock, something about it just set him off. So horney he found the simple act of opening his pants suddenly a complex act of advanced technical dexterity. He was still fumbling when she walked away, for the third time shutting a bedroom door on him. Sam hurried to remove his shoes, socks, trousers and boxers, placing the shoes together by the wall behind him and folding the trousers on top. Dropping back into his seat he considered how oddly obscene he must look, rock hard and nude from the waist down. He considered removing the jacket but didn't, he didn't think he was quite at 'improvising and anticipating what she wants' yet.

The next few minutes were agony, his mind picturing how Catherine might come out, what might happen. Ultimately it was not anticipation of what might happen it was the empty space of having no idea that drove him wild. When Catherine returned, bearing once more the gloves, the lube and the towels that feeling of burning curiosity refined itself down to the black box in her hands. Still in shrink wrap so... new? For him? Had she planned for him to come back or was this just a new toy and he was as good a first recipient as any?

"Yes Miss Jones." He said without a moments hesitation and slid our of the chair forwards on to his knees. He crawled forwards, low and abased, looking up at Catherine Jones someone he had once hoped to conquer. Yet he was the one on his knees. Not just on his knees, swaying his ass as he crawled, trying to seem alluring wanting her to revel in his, well submission.

Catherine patted the covered couch beside herself. The fact it was the exact gesture one might use to tell a dog they were indeed allowed up on the couch was not lost on him. Awkwardly he got up on to the covered cushions and placed his hands on to the back of the couch. The position filled his head with memories, and he didn't even have to try to convince himself this is what he wanted.
 
God he's easy. Catherine knew well enough to keep her comment in her head, suspecting her companion would take it the "wrong" way. Not that there was a right way to take it, but... It was such a mindfuck how at-odds his professional self was with the person he was right now. If she hadn't had the continuity of perspective to be sure she would've wondered if he'd swapped out for a double. But it was the same switch she'd flipped in him back in that conference room, and watching him lose the use of half of his braincells at her command was a very delicious kind of magic.

She admired his body with open hunger as he crawled towards her, putting his muscles and mobility on easy display. God, she wanted to push his legs back over his shoulders and fuck him until he sobbed. But there would be time for that later. A low rumble of her stomach confirmed that they really did have other tasks to see to. And a potentially uncomfortable conversation to have.

Later, a little later. Right now she needed this.

"Good boy," she purred as he mounted the couch, even if he had arrived perpendicular to where she'd intended. Clearly he liked being reminded of how she'd fucked him four weeks ago. Well, it was as good a position as any, so she stood and reached over and gave one of his muscular cheeks a firm squeeze. "Whoever your personal trainer is, they deserve every penny."

Then she withdrew, pulling the glove onto her right hand and uncapping the lubricant bottle with her left. He could hear the familiar, wet sound of lube being squeezed into her palm, rubbed between her fingers and warmed before she held his cheeks apart with her off hand and pressed a slick finger to his hole. "Relax for me..." They went through the same routine as before, Catherine muttering calming encouragement to Sam as she worked her finger into him, pausing and pulling out to add more lube as required.

When she was seated she crooked her finger, finding and stroking the spot that made him moan against his will. "Don't get too excited," she chided as she worked him up, reaching around with her other hand to stroke his stiffening shaft. She wanted him turned-on enough to be receptive to her next suggestion. And warmed up enough to take it. "I don't know why you're getting so worked-up right now, you know I'm not going to let you cum this early in the evening."

Chuckling at some joke inside her head she then let his cock drop and grabbed the lubricant bottle again, adding enough slickness to her digits to begin to work in a second finger. With two she could scissor slightly, helping to prepare him for the third as she stroked his shaft in time with the motions of her fingers inside him. But she didn't actually add the third, instead slowing to the point where she was only moving her wrist back and forth the slightest bit, and her hand on his cock had stilled entirely.

"I have a gift for you, Sam. I'll admit I wasn't sure if I'd even bring you home to give it to you, but..." The tips of her fingers twitched against his prostate. "Do you want to see what it is? I'll show you if you'll promise to wear it for me over dinner. You did want to have dinner with me, didn't you?"
 
Sam felt a surge of, well, pride when Catherine squeezed his tight muscled ass and complimented his trainer. He worked hard, to look like this after all, he saw a personal trainer once a week on top of several classes, squash and weekend runs. He did it for himself, he didn't need affirmation from anyone, he still grinned like an idiot though. Something about the power dynamic, she didn't have to be nice to him after all, made the compliment land.

"Yes Miss Jones." This was it, the first time more or less sober she would penetrate him. For a split second he considered calling it off, leaping off the couch making his apologies and leaving. The thought wasn't rational just a moment of panic. Then her fingertip entered him and oddly he calmed or perhaps committed, his breathing deepened considerably and he did his best to relax.

As Catherine hooked her finger he let out a low groan. She was being gentler now, or at least it felt that way compared to his probably exadurated memory. Still the same feelings of instability and intensity rolled through him, being ready for it didn't prevent him moaning and arching his ass up.

She sounded so calm, genuinly perplexed as to why he might be having difficulty with his composure as one gloved hand worked his hard shaft. Why was he making such a fuss, she was after all trying to help him relax. Shouldn't he be getting calmer? The incongruity only made him harder, especially when she told him she wouldn't let him cum. Catherine had plans, the evening had only just begun.

"Of course Miss Jones, I will-" he interrupted himself with another guttural moan as her finger slid along a ridge of his prostate. "Ah, try to control myself." Oh course he couldn't, if she wanted him to cum right now he would. And it seemed that maybe she would, working in a second finger and playing with him, truely fingering him as she had that night.

Only to slow again, gently moving his ass hole and holding his cock like it was the most natural thing in the world. So he was, sort of, right, with one guess at least. Catherine had considered a second meeting, whatever was in that box proved it. He didn't feel smug or triumphal as he might have expected just... glad, useful. Like he had done a good job.

But what was it? Something he could wear at dinner? Underwear maybe? He had no idea. How much of this evening had been planned in advance? Had the tape, no, he cut that line of thought off. He had to know. So what if he had to wear whatever it was? Maybe it was a new tie? Unlikely but not impossible.

"Please Miss Jones, I am desperate to know what's in that box. I promise I will wear whatever it is. I would love to have dinner with you and love to wear whatever it is while we do if that's what you want." Sam responded, after all, how bad could it be?
 
Catherine's "consideration" had been little more than an alcohol-fueled impulse-buy after a particularly unsuccessful night of hunting when she'd gotten back to Alta. In that moment she'd given real thought to what it would be like to domesticate Sam. He certainly met her standards for attractiveness, self-care, and life stability. He had the resources to meet up with her as they pleased in exotic locales, and he certainly would understand that her schedule was not always the most accommodating. And... something about the contrast between what he was like in the boardroom and in the bedroom was undeniably hot.

But that moment had passed quickly, and when one of the porters had brought up her package and left it in her foyer she'd thought little more of it besides chucking it in her closet. Unlike Sam's tie it wasn't his, and she told herself she could always give it to any new pet she decided to take into her care. Her tendency was to rotate boy-toys every six months or so anyway, so it wasn't as if she wouldn't have a new piece of ass to work with in the eventual future.

Now Sam was back. Fuck, she'd taken him home with her, against her better judgement and with no alcohol besides the few sips she'd had while they rested to cloud her judgement. He was sober, too, but... dammit, what was his excuse. He'd looked ready to foul his pants in fear when she'd shown him the video she had of him. This was bad for him, too.

They were both idiots. But damn if being an idiot didn't feel fucking amazing.

"Patience, Sam." A simple yes, Miss Jones would've sufficed, but hearing him beg was nice. It made her pussy throb and as she pulled her fingers slowly free of his ass she wondered if perhaps there was time for him to relieve some of her "stress" before they left for dinner. Her main hesitation was over whether that was too much of an unearned reward, so early in the evening.

Sam could hear her peel the glove off of her hand, and if he turned he could watch her unwrap the cellophane from the box and put it aside before pulling the outer cardboard sleeve free, too. Inside was a black cardboard box that came away into two halves, lined with molded plastic that kept a simple device of heavy stainless steel from rattling around. The bulk of it was oblong, tapered at one end, while the other end first narrowed then bulged outward to an oblong flared base. It was neither particularly large or long, but it was heavy, and as cold as the ambient air until Catherine walked it over to the sink in the kitchen and ran it under warm water until pressing it to her wrist produced a satisfactory response. Warm but not too warm.

Walking back to the coffee table she held it up by the back of the couch for Sam to inspect.

"This will go in your ass, and you will wear it until I say you can take it out. Do you understand?"

When she had his affirmation she disappeared behind him once more, squeezing lubricant onto the working end and making sure the bulb was slicked and still warm before wiping her off hand on the towel and then spreading his cheeks and pressing the plug against his hole. She pressed, slowly easing it into his lubricated and relaxed ass, using only the least required force until the widest point of the bulb passed his outer sphincter and his own muscles did the rest. The flared base kept it from being swallowed and she aligned it along his cheeks so it wouldn't press painfully while he was seated or walking.

She wiped her other hand on the towel as well, then stepped back. "How does that feel? Try standing up now, Sam." Then she had him do a few laps around the living room, checking to see if the plug was going to try to escape. "Do you think you can walk a few blocks with that in?"
 
Sam stared at the lump of steel like it was a snake, there was something brutally industrial about it. One thing was apparent he and Catherine had wildly different definitions of the word wear. Still he'd said he would and it wasn't so big, not so big as the dildo anyway and it wouldn't be for long surely. It was another layer of commitment and control though, not just put this up your ass, take this up your ass and accept you don't get to decide to take it out.

"Yes Miss Jones, I understand." Even as he said it Catherine disappeared from few and he heard a tap running. These were the moments he didn't think about, hovering, his ass exposed waiting for her to do something to him. It gave him dangerous moments for introspection, to think what the fuck am I doing? But before he could decide on an answer he heard the sharp report of her heels crossing the floor again.

Taking the plug was very different from Catherine's finger or the dildo, it was rapidly much thicker than ther former for a start. Compared to the latter though unlike the comparatively pliant dildo the plug was steel, hard and unyielding. At its thickest point it felt colossal and Sam bit his lip and groaned just a little at the almost painful feeling of stretching his asshole. That lasted only a moment though as he felt the perverse sensation of his ass pulling the plug inside of him. He let out a breath he didn't realise he had been holding as he felt the flared lip touch the outside of his hole.

Sam stood as instructed and felt the hard metal inside of him. What he felt was absolutely aware of it, every movement was informed by how it impacted on the hard steel inside of him. There was no way he could forget it, it was so hard him his internal muscles pushed against it uselessly, and so heavy he realised he was as he walked occasionally clenching against the irrational fear that it would just... fall out.

"It feels," Sam paused thinking for a moment apparently unaware of the fact he was stood pantsless in front of his rival. "It feels like I am full Miss Jones, its hard and heavy." He was thinking about it as she finished. His mouth went dry, of course, dinner so that wouldn't be entirely a break then. The thought of going out in public with his asshole violated was horrifying the closest thing to public sex done was sex on a boat at his families lake house. But then, no one would know? Would they? No it would be secret. He swallowed trying to bring some moisture back into his parched mouth before he replied.

"I can do that Miss Jones, if that's what you want." He couldn't run that was for sure and by the end his ass would be sore from the paranoid clenching and unclenching but he could do it.
 
It didn't vibrate, or make any sort of noise, and Catherine was sure from it's shape that unless he did something very odd it wouldn't actually fall out. Which made it perfect for the kind of public-but-not play she enjoyed. Sam would feel it with every breath, but besides whatever his own discomfort telegraphed no one else would have the slightest inkling. And anyone who saw them would likely write off his hesitation as the very natural reaction to sharing dinner with an attractive and aggressive woman. Nobody in Sofia knew Sam, or would spot how out-of-character his trepidation around Catherine was.

"Yes, that's what I want," she replied with an expression that suggested he was an dull for doubting that. "You should get dressed now, I'm hungry and I'm sure you are, too." Those dainty fingers of hers once more gestured at the guest bathroom. "There's a pack of baby wipes in the medicine cabinet, if you want to clean yourself up a bit. Just don't dawdle."

Reclaiming her own glass of whisky she moved the towel on the couch aside and relaxed back into her original seat. Her green eyes followed Sam as he went about his business, getting himself back into presentable shape.

Her glass wasn't quite empty by the time she was ready but she set it aside regardless. They'd be back later. As delicious as Sam looked when he was half-nude with his ass on display for her, that sight couldn't satisfy her stomach, and they had some important matters to discuss over a good burger and a tumbler of something brown and bracing.

"Let's go, then. Hope you like burgers."

Catherine stood and led the way, taking her purse but leaving her laptop bag behind. After locking up behind them she took them back to the elevator, down and through a minimalist lobby done up in dark blue with a heavy touch of greenery that fit with the Sofia vibe. They exited onto a side street that took them onto the main promenade and through a moderately dense crowd of tourists and locals alike out to enjoy the beautiful southern-californian evening. People walked far slower than they did in New Troy and with a far more relaxed air about them, walking as much for the joy of movement than to get somewhere in any hurry. Catherine had slowed her steps as well, both to not have to push through other parties but also in deference to Sam's cautious gait.

True to her word they didn't go far, two blocks down and then onto another side-street before heading into a restaurant with a dark and moody ambiance and large booth seats over a black-and-white tile floor and natural wood finishes. The hostess appeared to recognize Catherine, greeting her with professional familiarity and giving Sam a customer-service-smile before before guiding them over to a two-top booth near the front where they could enjoy the vivid colors of the setting sun and the vaguely salty air flowing in through the large open windows.

"For a whisky bar they have a good burger selection," Catherine remarked once they were alone with their menus and glasses of ice water. Only two pages in the folios were dedicated to food, a mix of usual gastropub staples, and the rest dedicated to enumerating an impressive selection of whisk(e)ys from around the world, plus a few other liquors at the end. Catherine bothered to read none of it, familiar with what was there and what she wanted, and pulled out her phone to read something while Sam considered his choices.

When he looked ready Catherine put her phone away, and their server returned moments later. Orders were placed, a bourbon whiskey plus a "bloody rare" burger for her, and then they were alone again.

"Thusfar I have dictated rules to you, Mister Cauldwell." She started, giving Sam a moment to turn his attention to her if it had drifted. There was something different in the way she spoke to him now than she had at her apartment, and it was closer to how she spoke to him when they were at work. "What we need to discuss now is terms, of the agreement we are entering into. I don't think either of us is convinced this will be the last time we will make this particular brand of... mistake." She waved her hand to generally indicate their presence together outside of work. "So I want to ensure we are on the same page with regards to this--" she paused as she considered her phrasing, "--rivals with benefits arrangement."

Catherine fell silent once more, waiting for any input Sam had.
 
"Absolutly, burgers sound great." Sam almost chuckled as he hurried to get dressed, it was just so normal. Though for Catherine maybe that's what this was with their work connection being the only element that made it strange. She was talking like this was a regular hook up because to her it was? That thought felt strange, he didn't know why it didn't occur to him before. Well because he'd been focused on himself, was the slightly shameful answer. He should better than that, not from an empathetic perspective, but as a negotiator, he should be able to put himself in the other person's shoes and he was disappointed in himself that he hadn't.

The walk was, uncomfortable, for once he didn't have any complaint at walking at a slow amble. Every footstep, after all, moved the plug inside him not a lot, it didn't hurt but he was incredibly aware, it seemed to take up his entire front brain. That night a month ago was the only time he had anything up his ass and it had been relatively brief, drunk, and frenzied. This was different it was just so constant every step a reminder. He had the irrational fear that people could somehow tell, that there was some invisible neon sign over his head reading 'THIS GUY HAS SOMETHING IN HIS ASS'. It was ridiculous but it made him nervous every time someone glanced at him, knowing he was being absurd didn't help, in fact, it made it worse.

The journey went by fast, focused as he was, finally sitting in what he had to admit is a bar he would normally adore. At the moment though he didn't really have the focus to appreciate it. He periodically fidgeted and shifted in his seat as if he could find some magic position where he couldn't feel so full, feel the weight. When the waiter finally came he realised he had only been pretending to read the menu while he tried to get his thoughts together.

"I, er, will have what she's having." he went with before handing over the menu. As they were left alone he turned his attention fully on Catherine. Sam grinned when she said mistake, she wasn't wrong there. This was all a horrible decision, series of decisions by now actually. He kept waiting for himself to 'come round' to wake up, for his good judgement to take over and stop all this but that just didn't seem to be happening...

"I think that is a very good idea." He began, shifting awkwardly in his seat again. "I think some things almost go without saying but we should say them anyway. First, no one can know, at least until the case is over, I don't think what we are doing is wrong per se, but even the appearance of impropriety...." He left that hang, it didn't bear thinking about, reputation was everything for both of them. "The second is that I am, I hope obviously, enjoying this. But I have no frame of reference for this kind of arrangement. To put it another way if two months ago you'd told me what was going to happen in that apartment I'd probably have assumed it was a bad joke or a metaphor. Even in the moment, there were things I... wasn't entirely happy about but subsequently couldn't get out of my head." Sam paused for a moment trying to bring thoughts into words.

"I think I enjoyed not enjoying them? I don't know. What I'm trying to say is setting terms is a challenge for me because if you'd asked me straight up before I'd probably have drawn the line somewhere before everything we've already done." He felt himself peter out staring at Catherine looking for any sign that what he was saying made sense.
 
Whatever she's having, really? Catherine wasn't sure if he was trying to endear himself to her, or if he'd simply suffered a moment of decision paralysis. Neither was a good look for the normally aggressively-alpha male.

At least he hadn't picked at her words. A small part of her had been afraid when she explained, if obtusely, how she saw things that he'd object and try to express some sort of attachment. That would've horrified her to the point of not knowing what to do. What came instead was, if far more emotionally honest than she would've expected from Sam in particular, still otherwise well within the bounds of things she knew what to do with.

"You are hardly the first man who enjoys things in the dark that he would not admit to in the light of day." Catherine responded, though her dry tone lacked it's usual bite. "I am not expecting your tastes to be well-developed yet. If this continues, I expect you will want to clarify and set new boundaries, or erase old ones, as you discover just how many lines you would've drawn that have since lost their relevance." She knew he was painfully new to the experiences she'd introduced him to, and as frustrating as it could be dealing with his ignorance she knew him not a man to be have to be taught something twice.

"Part of the service I will provide is pushing on those lines to see if they hold or break. I assume that is part of what you want out of this." The other part being mind-blowing orgasms, but Catherine didn't feel the need to say that out loud. "And that is what this is, Mister Cauldwell, an exchange of services for the mutual benefit of one another. Not a relationship, not any entanglement that incurs any debt to one-another on an emotional level. No commitment, and no exclusivity."

Leaning her forearms on the tabletop Catherine leaned across, looking slightly up at him with cool green eyes. "I like to keep my kennel well-stocked, Mister Cauldwell, and you should have no illusions about being top dog."

Pushing back to where her back hit the booth wall once more she sipped at her ice-water, then added, "of course, you retain the same rights unless we negotiate otherwise. I don't give a shit who you fuck on your own time. Does that sound like a fair trade?"
 
Sam was at first shocked, then surprised he was shocked, by Catherine's open statement of her... kennel policy. It registered on his face as a widening of his eyes. So, no commitment, no exclusivity, he hadn't thought about it so he wasn't disappointed as such. It felt strange to discuss it so openly, so frankly, though the unusual was normal for this arrangement.

Of course this analysis was complicated by the fact Sam was rock hard again from the moment Catherine got to describing her paramour as in a kennel. He didn't want to think of himself as one of her dogs, but something about the way she said it had set him off.

She didn't care who he fucked, he could work with that. Especially as he was increasingly convinced that the prospect of conventional penetrative sex was at most incredibly unlikely. Sam hadn't thought about that till now, he'd need to think about the implications back home.

"That, that sounds like a fair trade Miss Jones." He shifted uncomfortably in his seat, the erection causing his sphincter to squeeze on the hard steel of the plug. He let out a small puff as that sensation set his nerves tingling. "I can work with being" Sam glanced around to be sure the server wasn't about to appear behind him like some sitcom. "One of the dogs in your kennel. How you rank them is of course up to you."

Sam tried to sound in control but his arousal combined with his attempts to hide it put a certain shortness of breath in his speech that felt painfully obvious as he squirmed in his seat.
 
A third party would assume Sam was simply flustered by his assertive and gorgeous companion. But he wasn't the first man Catherine had put through their current exercise, and she knew better. What she was less sure of was, which was more embarrassing: that he was clearly turned on by something she'd said, or that she felt uncomfortably warm between her thighs when she'd realized he was?

Their booth was unfortunately too exposed for her to check more thoroughly just how excited he was. Next time, Catherine thought, she'd pick a place with longer tablecloths.

"I'm glad you agree." She replied with genuine relief. "Some men can be such hypocrites on that point." God knew she'd dealt with her fair share of such. Men who were incensed by the fact that a pretty, powerful woman would have other options they'd wish to pursue, and a willingness to pursue them. Dan, for his various faults, at last hadn't ever tried to assert exclusivity upon her. Sam, it sounded, could be reasoned with as well.

"The rest I have is bureaucratic errata. I get tested regularly, and I assume you do or will do the same." Though without traditional intercourse on the table the chances of transmitting a STD between them was lower, it wasn't quite zero with oral sex involved.

Without letting him comment, she changed the subject. "I will do my best to tell you a date and a time a week in advance of our visits. As much fun, as today's spontaneity was, that was the kind of risk that could jeopardize both our careers." Which wasn't exactly saying it wouldn't happen again. "Do you have your personal device on you?" She assumed that, like her, he carried one phone for work and one for himself. If he yielded it over she quickly sent a text to a phone number with an Illinois area code, a single period that nonetheless made something her purse buzz once a moment later.

They were interrupted not long after by the arrival of their drinks. Since he'd duplicated her order they were both brought tumblers of neat bourbon. Their server told them their food would be up soon, then yielded back their privacy.

Catherine took a slow sip of her drink, ignoring Sam for several long moments before replacing the glass on the table in a deliberate fashion and fixing him with a knowing look. "So, Sam, how much of that conversation did you actually take in... and how much of your attention has remained stubbornly focused on the plug in your ass?" She hissed, low enough to not risk being overheard. "You've been thinking about it this whole time, haven't you?"
 
Sam nodded proffered his personal phone as Catherine exchanged their numbers. He decided to leave the fact he already getting regular tests due to his lifestyle in one of the most visited cities on earth, that might give her rather the wrong impression about his promiscuity. Well what had been his promiscuity, this last month had been somewhat dry due to his distraction with Catherine.

She was right of course, and Sam nodded along, meeting outside work at a prearranged point made more sense. He didn't entirely trust himself that he wouldn't show signs of their, arrangements if they were to keep starting their liaisons in the office.

"Yes that all sounds completely reasonable. I will of course give as much notice as possible on my availability. As you say the last thing either of us would want is... this impacting our careers." As their order finally survived Sam moved to the bourbon quickly taking a fast, nervous slug.

"It is... certainly always in my thoughts Miss Jones." Just the act of moving to pick up the bourbon had moved the plug inside him. It was like an ever present reminder of his situation, that this wasn't just a nice meal in an excellent bar with a beautiful woman, it was something else.

"I am paying attention, but yes, every single time I move at all it's right there. It's just so hard." He didn't know if he meant the plug or his cock at that point, either way his ass was twitching on the hard steel. "I suppose you could say it keeps me in the right frame of mind."
 
He didn't need to say it, as Catherine had already assumed it. Of all his colleagues, she was certainly not in a position to judge for how many partners he had or how frequently he saw them. Their main difference was in the discretion required to save professional face. Sam would get a playful nudge or a knowing look from a colleague if he excused a sleepy yawn or a poorly-tied tie to having been up late with a "new friend". Catherine would get disgust and scorn, at least from her male peers. And her female ones were few and far between enough at her level to offer little safe harbor.

Not that she wanted to talk about her sex life at work. Which brought her back around to the thought that she was "casually" having dinner with the lead of the opposing representation for the biggest case of her life... while he fought the urge to squirm due to the steel plug she'd put in his ass.

The thought made her cunt clench and throb between her legs, a feeling she tried to ignore as she kept the pressure instead on Sam.

"It does, doesn't it..." She agreed lightly. "Such a useful training tool. They make ones that vibrate as well, but... I think I'm getting plenty of mileage out of your current predicament." Though stainless steel could be an excellent carrier for such vibrations later, when they returned to her apartment. Catherine was still on the fence about how many times, if any, she'd let him finish. But if she was feeling generous, holding a wand against the plug in his ass as he humped her leg to completion was certainly an appealing mental image.

"And you'll find it so much easier to take what I'll be giving you later tonight." Catherine added casually, as if she wasn't talking about bending him over the most convenient piece of furniture to fuck his ass. Her language was a little obscure, but she knew he knew what she was talking about. "I mean, you've been thinking about it since last month. It would be cruel to not give it to you tonight, now, wouldn't it?" She grinned. "Though, now I'm curious. If I gave you the option of something more... conventional, would you even take it?" Though she felt sure what his answer would be, she wanted to hear him say it.
 
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