His Submissive Personal Assistant

His Submissive Personal Assistant

Author's note: All characters in this story are over eighteen and act consensually. No AI was used in writing the story. I welcome email feedback or DM's and will do my best to reply. HG xx.

Thomas stretched and leaned back in his high-backed leather executive chair, placed his hands on his beautiful oak desk, and sighed with satisfaction. There were times when, as one of Haines Thornton's senior partners, life could feel good. He had just been finalising invoice details of a new tax advisory job with one of the admin girls, a young lady called Maddie, who wore a tight sleeveless dress that showcased her gorgeous young breasts. Of course, she was thirty-five years his junior, and wouldn't ever be interested in a man of fifty-seven, but my word, having her tits jiggling in front of him for several minutes had made his day.

Stop it, Thomas, you randy old goat, he admonished himself. If he was honest, the other, more realistic reason he was feeling so pleased was the prospect of billing a new client tens of thousands over the coming months. Partners' earnings, especially their bonuses, were heavily linked to new business, and the last six weeks had seen a number of lucrative new clients. I might treat myself to a new Porsche 911 Turbo S, he thought.

Thomas reflected that, as The Beatles once sang, money can't buy me love, and there was no way he'd ever get his hands on the likes of young Maddie. Well, he could, but paying a professional for such a service was not cheap, even for someone with his wealth. And of course, it wouldn't be love exactly, would it? Sex, yes, but, nice as that was, it didn't count as a relationship. Suddenly, he felt a little sorry for himself, and decided to go for a walk around the park next to the office, in order to lift his spirits.

It was a beautiful spring day in Southampton, on England's south coast, the sort of day where you weren't sure whether you needed a jacket or not. He opted to leave his jacket in the office, and strolled around the park, enjoying the sweet smell of new life as the plants and trees around him awoke from their winter slumbers. He was reminded of the time, thirty years previously, when he'd met his wife Fiona in such a place. She sat down on the park bench where he was eating his lunch. He offered her one of his sandwiches, and they began to chat. By the end of their lunch breaks they'd exchanged numbers.

Thomas and Fiona married within the year in a lavish ceremony paid for by Fiona's very rich parents. His own parents were not quite in Fiona's parents' financial league, but were comfortably off, and his father told him that he was making a smart move. "Always marry upwards, son," he'd said. "You'll thank me if it all goes wrong and you get half of her money."

Initially, Thomas dismissed his father's advice, since he was sure he was marrying for love, not money. Fiona was everything he could want in a woman: she was pretty, charming, well-educated, having gone to a fee paying grammar school, and of course very, very sexy. Within three years, however, he discovered that she had embarked on multiple affairs, and seemed unable to resist temptation. Fiona was never short of admirers, and seemed to revel in being chased. She always ensured that she got caught. She was, however, a poor liar, and Thomas usually found out about her indiscretions.

She begged for his forgiveness on many occasions, and he always gave it, telling himself that this would be the last time, but it never was. To be fair to her, she turned out to be a wonderful mother to their two children, and he was sure that in those child-raising years she was faithful to him. Once the kids had left home, she returned to her old ways, and he ran out of forgiveness. Thomas and Fiona divorced in 2023. She went to live with her latest man, and agreed that Thomas could have the main house near Southampton while she got the country cottage in Devon.

He stood up from the park bench with mixed feelings. Feeling the warm spring sunshine on his face was refreshing, but he realised that, even three years on, he wasn't fully recovered from the upheaval of divorce, and the difficulty of having to start again in his late fifties. He decided that he'd visit the local Official Porsche Centre at the weekend and see what they might offer for his current car as a part exchange for a new one. Retail therapy, of a sort, would make him feel better, he decided.

As he approached his office he was, as ever, greeted by his personal assistant, Olivia, who sat at a desk in the open office portion of the building's top floor. "Isn't it a lovely day, Mr. Watson?" she commented. "Spring has sprung, it seems. I'll be with you in a moment with your afternoon schedule. Would you like a coffee?"

Olivia had worked for Thomas for two years, from just after his divorce was finalised until the present day. She was in her forties, single and very good at her job. She always made sure that Thomas knew what meetings or appointments he had, formed the first line of defence from clients, handled all of his correspondence and even did his shopping when asked. Recently, she'd bought him a new putter to add to his golf bag, which had proved a success, helping him to lower his handicap to twelve. Thomas' buddies were astonished to learn that his p. a. had made the purchase. "You should marry her, mate," one laughed. "If you don't, I will. Three shots rom my handicap is a no-brainer."

Thomas realised that Olivia was standing in the doorway, waiting for his answer. "Oh, yes please, Olivia, a coffee would be perfect, thank you," he replied. By the time he'd checked his emails, Olivia was walking into his office with a tray containing two coffees and a bag of his favourite Haribo sweets. "Olivia, you are so naughty," he said. "You know these are full of sugar, and that I can't resist them. Tut tut, young lady."

Olivia smiled, as she always did, knowing that he appreciated her attention to detail. She knew exactly how he liked his tea or coffee and what treats he enjoyed. "Oh well," she sighed, "you can always complain to HR I suppose. But then I'd get fired and your world would collapse, wouldn't it? Well, the office part of your world, anyway. I'll have a giant strawberry, please."

Thomas chuckled inwardly. Only this morning, a young girl in a tight dress with her tits on display had held his attention. Now, a stern-looking woman with her dark hair tied back, wearing a smart jacket and sensible top was doing the same, but for very different reasons: coffee and sweets.

It wasn't that Olivia was unattractive, not at all. It was just that she was very businesslike and professional. Her makeup was very discreet, there was no flesh on display and she always wore tops with a high neckline, usually with loose-fitting trousers. When she needed to read something, she donned reading glasses that made her look like a librarian. Some of the office girls dressed as if they were about to go clubbing. Olivia dressed as if an elderly aunt was coming to tea.

Only last week, one of the other partners, a jolly older woman called Mary, had asked Thomas about his personal assistant. "Your Olivia," she said, "she seems very straight-laced. I mean, I've never seen her wearing anything low cut or revealing, and although she's extremely polite, she seems to keep herself to herself. Don't you agree, Thomas?"

Thomas had to admit that he did agree. Given that Olivia had worked for him for two years, he knew little about her, since she hadn't volunteered much personal information. He knew from her curriculum vitae when he interviewed her that she'd made a career as a personal assistant, and it showed: she was extremely capable. He also knew that she was now forty-four years old, lived in the centre of Southampton and was single. She'd volunteered the information that she had never married nor had children, and lived alone with her cat, a ginger boy called Buster. And that was it, really: Thomas knew little else about her, at least of a personal nature. Even at the two office Christmas parties she'd attended, she had arrived and left alone and had stuck to soft drinks. She was both someone that everyone liked, and someone that no one knew anything about.

"A word to the wise, Thomas, if I may," his fellow partner Mary added. "You probably haven't noticed, because you're a man, but I'm telling you that your Olivia is besotted with you. Us women notice these things, and the way she gazes at you is unmistakeable. I mean, she may not plan to do anything, but I'd keep my wits about you if I were you. I have a feeling that there's more to Olivia than meets the eye."

Two weeks later, Thomas pulled his Porsche 911 into the car park of a large business hotel just off of the motorway that linked Portsmouth and Southampton. He often met clients there, although he was looking forward to this meeting because the client had insisted on buying them both dinner in the hotel's rather pleasant restaurant. Despite his wealth, Thomas still enjoyed a free meal when it was offered, although he would have to stick to drinking water since he'd have to drive home.

The meal was very nice, and the client, a self-employed businessman called Tony, was good company. Tony wanted some advice about inheritance tax planning, and preferred to discuss matters over dinner rather than in Thomas' city centre office. It was just gone eight o'clock when Tony settled the bill and shook hands with Thomas, thanking him for his advice. "Do you fancy a quick drink in the bar, Tony?" Thomas asked. "I feel I should pay for something tonight, after all."

"Very kind of you, Thomas," his client replied, "but I must get off home I'm afraid. I'm on bedtime story reading duties. Another time, perhaps."

After Tony had left, Thomas lingered at the table checking his phone for any messages, and catching up on the latest football scores. He loved sport of all sorts, although golf was the only one he played these days. At fifty-seven, his knees were not in great shape from years of playing football, squash and tennis. Suddenly, the prospect of going home to his empty house was unappealing, so he decided to go to the hotel bar and treat himself to a small beer. He would be fine to drive if that was all he had.

The bar was nearly deserted, since it was a midweek night in early April. Thomas approached the bar, noting the scantily-clad woman sat at a bar stool with her back to him, peering at her phone. She wore cute ankle boots with a high heel, black tights or stockings and a tight black leather skirt. Her top was a figure-hugging maroon sweater, but he couldn't see her chest. He said nothing as he motioned the barman over, but his gaze lingered on the sexily dressed lady close by, wondering if she was on her own.

"Good evening, my friend," he said to the barman. "May I have a bottle of Heineken, please?"

The woman next to him spun sharply towards him on her stool. "Oh my god!" she gasped. "Mr. Watson! What are you doing here?" For a split second, he didn't recognise her, but then it hit him. It was Olivia, looking like he'd never seen her before. There was a moment of silence as he took in her bold lipstick, dark eye makeup, impressive cleavage and her shoulder length hair.

"W-wow, Olivia, gosh!" he stammered, eyes wide open. "You look, umm, different!" Realising that standing at the bar, gawping at his p. a. like a teenager was rather rude, he sought to regain his manners. "Can I buy you a drink?" was all that he could manage, followed by, "What brings you here? It's a fair way from home."

Olivia seemed as flustered as he was. Clearly she had not expected him to be in this bar at this moment in this hotel. Her house in Southampton was a good ten miles from where she was now, and his was further still. "I'm, umm, well, I'm on a date," she said. "Except it's looking like I've been stood up. He was supposed to be here at eight, but he's either fifteen minutes late or he's not coming at all." The barman arrived with his beer and her orange juice.

"Shall we grab a table?" Thomas suggested. "If or when your date turns up you can just tell him that your boss was here meeting a client and bumped into you afterwards. Then I'll disappear and, umm, leave you to it, as it were." Thomas was trying not to say something stupid, but was a little bit rattled. "Well," he said, raising his beer bottle, "here's to chance encounters, I guess." They sat down, clinked their drinks and wondered what to say next.

Olivia broke the tension. "I know what you're thinking, Mr. Watson. You're wondering what happened to the Olivia you're used to seeing in the office, all prim and proper. You're curious about why I'm sat in a hotel bar looking like I'm touting for business." Thomas spluttered and tried to assure her that he was thinking no such thing, but she interrupted him. "It's OK, Mr. Watson, I know I'm dressed like a tart, you can say it if you want because it's true."

Thomas was beginning to unscramble his brain. "Olivia, please call me Thomas, because we're not at work, are we? And look, I don't think you look anything like a sex worker, if that's what you're suggesting. Actually, I think you look......" He tailed off, wary of saying something too forward. "Well, you look lovely, and don't take this the wrong way, but you look really very attractive. Or, as my kids might say, you look hot. There, I've said it. You can throw your drink over me now."

She laughed, and they both started to relax. "OK, well thank you, Thomas. I'll take that as a compliment then. I suppose you're rather surprised to see that I do possess things like breasts and legs, since I keep them out of sight at work. I mean, they're hardly worth flaunting anyway, are they?"

The words were out of his mouth before he could consider their impact. "Seriously, Olivia? Your figure is gorgeous, and I never knew that you had long legs. I love your hair like that, too." Olivia normally had her hair scraped back and tied in a bun behind her head. Now, it tumbled over her shoulders, looking long and glossy. Thomas realised that his remarks were rather personal. "God, sorry, my dear, I must sound like a pervy old man. I apologise," he said.

Her reply was not something that he'd expected. "Thomas, there's no need to apologise," she said. "I don't think you're pervy, not one bit. I think, though, that you're maybe rather lonely these days. Sorry, but that's my impression from two years of working with you."

Thomas sat back on his chair as if he'd been slapped. Olivia had just said what he knew to be true but had pushed to the back of his mind. Lonely, she'd said. As a diagnosis it was spot on. Sure, he was popular with colleagues, clients and his golfing buddies. His children visited now and then, and he assumed he would become a grandparent before too long. And yet, he'd wandered into the bar because he didn't want to go back to an empty house. "Shall I get us a bottle of wine?" he suggested. "I'll pay for us to get taxis home."

"That sounds like a plan, Thomas," Olivia answered. He approached the bar and soon returned with two glasses and a bottle of Australian shiraz. As he filled each of their glasses, she said, "You're not the only one, you know. I'm the same, Thomas. I'm really, really lonely too, you see. That's why I'm here, dressed like a prostitute, hoping to snag some guy to spend the night with. I'll feel even worse afterwards, but at least I'll have a few hours of close contact with another human being."

Thomas nodded, trying to show her that he understood. "Well, except it looks like your date is a no-show," he reminded her. "Cheers. To shared loneliness."

Over the next two hours Thomas discovered a new person, one that he hadn't known before. He already knew that her name was Olivia, and that she worked for a great employer and a genuinely lovely boss in a firm of chartered accountants in Southampton. He also knew that she lived alone with her cat called Buster. What he didn't know was that she was politically right-leaning and voted Conservative, was a fan of most sports but especially football, listened to Iron Maiden and Rush, liked Chinese food or a really juicy steak and that her favourite colour was blue. Oh, and he now knew that she was very lonely.

Neither of them were properly drunk, but they'd reached that point where inhibitions are lowered and senses heightened. Things that might have seemed impossible suddenly became possible, even quite likely. Thomas looked down to see his p. a. stroking his hand, tracing one of her highly polished bright red nails over his wrist and along his shirt sleeve. "Can I interest you in a bit of mathematics?" she asked. He gave her a puzzled look, to which she said, "Loneliness is a negative, you see. Well, if you multiply two negatives, you get a positive, don't you? Why don't we make a positive together tonight, hmmm?"

In another situation, Thomas might have made his excuses and opened his Uber app to summon rides home. He might, perhaps, have told himself that getting involved with his p. a. was unwise, and possibly unprofessional. Then again, she was very clearly interested and was far from some giddy youngster being taken advantage of. Plus, he was ragingly horny and was with a hot woman who wanted sex with him. Go home to an empty house or book a room at the hotel and seize the moment? It was, he decided, an easy choice to make.

The girl at the hotel's front desk was most understanding. "Oh, don't worry, Mr. Watson, you're doing the right thing," she said. "It's much better to sleep it off than drive drunk. Anyway, your room is ready for you now; we're not too busy tonight. Just to confirm, a king sized bed, yes? Would you like a newspaper in the morning?"

The room's spring-loaded door had barely clunked shut behind them before Thomas had pinned Olivia to the wall, kissing her fiercely. She responded in kind, running her hands along his back and squeezing his buttocks. "Be rough with me, Thomas," she breathed. "I love it hard and rough. Pull my hair, choke me, all that. Tell me, don't ask me, yeah?"

Thomas could not believe what he was hearing. Polite, demure Olivia was unzipping his trouser fly, eager to feel his cock, while asking to be treated roughly. Thomas considered himself to be a dominant lover, even though he'd had very little opportunity recently. He enjoyed controlling his woman in bed, and even liked to inflict a little pain. He was no dominant BDSM master, but loved it when a woman made it clear that she wanted to submit to him.

He stood in the centre of the large bedroom, and ordered Olivia to pull down his trousers, remove his boxers, socks and shoes, and then suck his cock. Instantly, she complied, casting his shoes and clothes to one side before kneeling in front of him and reaching for his twitching, fully erect cock. "That big enough for you, young lady?" he asked. For now, Olivia remained fully clothed in her ankle boots, stockings, black leather skirt and low-cut lambswool sweater.

Olivia teased him by licking the pre-cum from the tip of his penis, tracing her tongue along his shaft, and sucking his balls. "Your cock is magnificent, Sir," she said. "I knew it would be." She hoped that Thomas recognised the submissive in her. It appeared that he did, which excited her beyond words. Olivia loved to be controlled and be ordered to comply, in the bedroom at least.

Thomas was thrilled that she'd instantly slipped into her submissive role and called him Sir. He groaned as she sucked, licked and masturbated his iron-hard dick. He was impressed that she could take him deep in her throat and hold him there, but even more delighted when he grabbed her hair and used her mouth, pulling her onto him then jerking her back again. Her throat made slurping, gargling noises and her whimpers of delight merely encouraged him.

After several minutes of oral pleasure, he picked her up, threw her face up onto the huge bed and stood over her, his cock twitching angrily. "Strip for me, bitch," he growled. "I've spent two years wondering what was under there. Now show me!" For a split second he worried that she would object to his use of crude language, but the wide smile on her face suggested otherwise.

Olivia removed her sweater and bra, revealing her top half. Thomas was astonished. His sweet, straight-laced p. a. was, it turned out, pierced and heavily tattooed, although she had no facial piercings at all. Both arms had colourful tattoos that reached from her shoulders to her elbows, depicting flowers, dragons and rainbows. On her front, roses ran from her pierced belly button and curled over her breasts, while a crucifix - or was it a dagger? - occupied the area between her boobs.

Thomas almost came on the spot as he observed the chunky surgical steel nipple rings that dangled from her breasts, pulling them down. She was, he estimated, at least a 'C' cup, and her rings looked exotic, heavy and very, very erotic, to him at least. "My tats aren't to everyone's taste," she said, "so I keep them hidden. Do you like them, Sir?" He nodded enthusiastically. "Wait until you see my back," she said, and lay face down on the bed. Thomas grinned as he saw that her entire back was a homage to the metal band Iron Maiden, complete with the band's famous and gruesome mascot, Eddie.

Olivia sat back up and sucked Thomas' cock for several more minutes, before removing her ankle boots and wriggling out of her leather skirt. She wore no panties, and left her hold-up stockings in place. She opened her legs, revealing yet more tattoos on her thighs, along with a clit piercing. It was a vertical bar, which she began to play with. Her clit immediately rose, and Thomas could see how the bead at the bar's base pressed against her clitoris. "I'm so fucking horny, Sir," she whimpered. "I'm begging you. Fuck me hard, please Sir. Make me yours."

Thomas eased off the remainder of his clothes, threw them to one side and pulled her to the edge of the bed. He lifted her legs so that they were draped over his shoulders, and used his erect cock to tease her pussy lips, butthole and clit. She was totally hairless, her slit glistening with her secretions. "How much do you want my cock inside you, slut?" he demanded.

"Oh Sir, so, so much," she replied. "Split me in two with your big, hard cock. Do whatever you want to me. I mean it, Sir, I'm your fuck toy." Thomas felt as if he was dreaming. Was this really the same Olivia that he'd worked with for two years, never suspecting that she was, in fact, a horny submissive slut? It was as if there were two Olivias, a sort of female Doctor Jekyll and Mister Hyde.

Olivia squealed as he drove his hard cock into her pussy, sinking it in all the way to his balls, which slapped against her thighs. "Take it, young lady!" he barked. "You've been wanting it for two years so here it is!" He commenced a rhythm of thrusts, burying himself inside her before easing out, making her plead for more. "You love it, don't you?" he growled.

"I do, Sir, I love it so much," she panted. "Please cum in me, Sir, please. Fill my cunt with your hot, creamy cum, Sir, I'm begging you. This pussy is yours, claim me!"

After several more minutes, Thomas flipped her over on all fours so that her bottom was in the air, facing him. He toyed with the idea of fucking her ass, but decided to leave that for another time. He couldn't, however, resist spanking her buttocks hard; they were so round and peachy. Olivia yelped as he smacked her, before urging him to do more. "Hit me harder, Sir, I love how it feels!" she cried. Again, Thomas decided to save that pleasure for another time.

He increased the depth and frequency of his penetration, before placing his hands around her neck and pulling her head backwards towards him. Using his strong arms as a brace, he pounded into her, choking her at the same time, which she seemed to love. Conscious of safety, he released his grip on her neck just as he climaxed. "I'm cumming, bitch!" he cried. "I'm going to fill your little pussy with every last drop of my spunk. Mmmm, so good, so...... fucking..... good..... Yes! Yes Olivia, yes! FFFFFFUUUUUCK!" He erupted inside her, his balls contracting as he splashed his seed deep inside her, making her moan and groan with delight.

He stayed inside her for several minutes, ensuring that her pussy was fully coated with his fluid. Eventually, he felt his cock start to soften and sensed her body relax beneath him. He toppled forwards, crushing her under him, and rolled sideways to avoid injury. He found himself face to face with her on the bed. "Hello you," she said, gazing at him with wide eyes. She began kissing him, over and over, playing with his tongue and peppering his neck and shoulders with tender little kisses. "That was incredible," she murmured. "Thank you, Thomas, thank you."

Thomas sat up, reached for the room service menu, and declared, "A tray of sandwiches and a bottle of Champagne, I think. Afterwards, we can fuck some more. We've got two lost years to make up for, have we not?"

Over the following six weeks, as spring turned in to early summer, Thomas and Olivia had more sex than either had enjoyed in the preceding two years. They took every single opportunity and not a few risks. From time to time, Thomas would walk to his office door, and call, "Olivia, would you come to my office please? I have something urgent which needs attending to."

Olivia would slide the 'Meeting in Progress' sign across the outside of the door, close it behind her, and crawl under his desk, where his throbbing and hard cock would be waiting for her. They jokingly called it 'milking time' because she would suck him to climax and swallow his cum. "I've milked you dry, Sir," she would say, opening her mouth to show him that it was empty. Whenever they had sex, which was often, she always called him Sir, complied with his wishes and never tried to assert control.

Another of his favourite things was to reserve the boardroom, ostensibly for a client meeting but in reality for sex with his p. a. Thomas would issue strict instructions that he and his client should not be disturbed, and would send Olivia to prepare the room, switch on the coffee machine and put out some biscuits. When he entered the room, she would be bent over the boardroom table, trousers and panties around her ankles, masturbating gently. Thomas would unzip his fly, drive his cock into her and cum within five minutes. Then he would sit her on the table, kneel in front of her and lick her pussy clean, always ensuring that she reached orgasm. Olivia invariably came when he ate her, partly because he was skilful but partly because she adored getting oral pleasure.

Once, when he had made her squirt all over the boardroom table, he asked her why she'd cum so spectacularly. "You don't normally squirt," he said, "why today? I mean, I loved it, but I'm curious."

Olivia's reply was out of her mouth before she'd even thought about it. "I imagined that I was being eaten by a girl," she said. "It's a fantasy of mine." As soon as she'd said it, her face flushed with embarrassment. She had just admitted her bi-curious feelings to her boss, and was anxious as to how he would react.

Much to her relief, Thomas was rather excited at the idea, and pressed her for more details. She told him that she'd had a six month relationship with a girl when at university early in the new millennium. "Her name was Charlotte, and she made me cum over and over when she pleasured me. I was a little bit in love with her, I think, but it didn't last. I've not had sex with a girl since then, but I fantasise about it a lot."

Thomas and Olivia agreed that she would maintain her dress sense in the office as before, reasoning that any change might arouse suspicion. However, they began to play a little game. For example, sometimes Olivia would sit across the desk from Thomas, wearing her usual long trousers, and say, "I've got fishnet stockings and a suspender belt underneath, with no panties. Want a peek, Sir?" Thomas would unzip his fly and begin masturbating behind his desk as Olivia opened her trousers, flashing her exposed pussy at him. Inevitably, she would slip two fingers inside her wet pussy, then they would watch each other masturbate to delicious mutual orgasms.

They both worried that they would be discovered, but no one seemed to notice. As a senior partner, it would be a brave soul who interrupted him when a meeting was in progress, and it was entirely normal for his p. a. to sit in on such meetings. For her part, Olivia had outwardly changed nothing about her appearance or behaviour. To all intents and purposes, it was business as usual.

One afternoon, Thomas told Olivia that he would love to take her to dinner at the hotel where they'd met a few weeks previously. He asked her to wear the same outfit as on that evening: ankle boots, stockings, leather skirt and tight top. He picked her up from her home and drove them both to the hotel. They enjoyed a nice meal together before retiring to the bar. Thomas had booked a room for the night, so they felt able to have a few drinks, which they took to a small couch in the corner of the bar.

After a few minutes, Thomas nudged Olivia's arm, pointed to the bar, and said, "Do you see that girl chatting to the barman? The one in the skin tight leather jeans? She's almost as hot as you are. Why don't you go and talk to her? You never know, she might be up for a bit of fun. I'll wait here."

It seemed a long shot, but Olivia decided to give it a try. She was feeling so randy that any sexual possibility was worth pursuing. She placed her glass of wine on the bar next to the girl and waited for her to notice the older lady in the short skirt perched alongside her. It didn't take long. "Oh, hello," the girl said. "Can I help you?"

"Oh, I just saw you and thought you might fancy some female company," Olivia replied. "Stop you getting hit on by some overweight sales guy from a company that makes cardboard boxes or something." The girl laughed and turned to face her. "My name's Olivia, what's yours?" she asked.

The girl replied that she was called Ellie, and that Olivia could most certainly buy her a drink. "Funny that you should say about overweight sales guys," she snickered. "I'm here on a course called 'How to Sell With Confidence' and there's a few guys who match your description. I'm the only girl, it appears, so a bit of female company would be nice. What brings you here, Olivia?"

Olivia took her time in replying, sizing up the young woman in front of her. Ellie looked to be in her early twenties and was very slender; her impossibly tight leather jeans accentuated her long legs. She wore a low cut silk blouse that revealed modest but pert breasts. Her blonde hair was cut in a short and fashionable bob. Flawless skin, perfect teeth and sparkling blue eyes made her look stunningly pretty. Olivia felt her pussy tingle as she answered. "Oh, I've just had dinner with my boss. He's gone to the bathroom, and I saw you and realised I just had to introduce myself. You look fabulous, by the way."

Ellie smiled, cocked her head to one side, and said, "Thank you. Umm, I'm not sure you're being completely honest with me, are you?" Her tone was flirtatious rather than accusatory. "In fact, I think you're hitting on me, which is fine, but what about your boss?"

Olivia had a dilemma. On the one hand, she didn't want to scare Ellie away by suggesting Thomas' inclusion, but on the other hand, she was reluctant to disappoint him by waltzing off with Ellie on her own. Eventually she said, "Actually, Ellie, he's just over there." She pointed to the table in the corner where Thomas sat, sipping his drink. "What do you think?"

Ellie looked surreptitiously over Olivia's shoulder. "You know, he's not bad looking," she commented. "Not bad at all. Look, don't freak out, but what if he joins us?" She traced her fingers over Olivia's leather skirt in a blatantly sensual way. "It's the kind of fun I was looking for when I signed up for this course." She leaned forwards, kissed Olivia full on the lips, and said, "I like men just as much as women. Both at the same time, ideally." Without Ellie noticing, Olivia directed a thumbs-up towards her boss.

Having spotted Olivia's signal, Thomas strolled across to the bar and introduced himself. "Hello, my dear," he said, facing Ellie. "I'm Thomas, and the lovely Olivia here is my personal assistant. Two questions for you, if I may: what's your name and are you interested in a little three way fun?" Thomas had clearly decided on the direct approach.

He had his answer immediately. Ellie slipped from her bar stool and kissed Olivia while simultaneously stroking her hand over the very obvious bulge in Thomas' trousers. "Good evening, Thomas," she purred. "I'm Ellie, and that sounds exactly like the sort of fun I enjoy." She smiled at each of them, before saying, "Shall we?" The three of them linked arms and headed for the elevators.

Olivia and Ellie were feeling so frisky that they could not keep their hands from one another as the elevator ascended to the fourth floor. Thomas watched approvingly as the girls locked lips and made out, their hands wandering over one another's bottoms, breasts and faces. Thomas resisted the temptation to release his cock from his boxers, even though there was no one else in the elevator.

As they approached his room, Olivia drew close to Ellie and whispered in her ear, "Thomas is quite the dominant, by the way, and will order you what to do. Just so you know, OK?"

"Don't worry," Ellie replied. "I'm a good girl, and adore being a bit submissive."

"Snap," Olivia responded. "This is going to be fun." As they entered the room, Olivia announced that she needed the bathroom, leaving Ellie and Thomas to make conversation while she peed. She finished and joined the others in the room proper. Thomas addressed the women, saying, "Clothes off, please girls, then on your knees, ready for some cock worship. Do it now, if you don't mind."

Olivia was impressed by how eagerly Ellie stripped off, and was awestruck by the young girl's lovely body. Ellie was flawless, with perfect pale skin, untainted by any piercings or tattoos. Mother Nature had given her modest but pert breasts, a flat tummy and slender, graceful limbs. A few freckles were dotted around her body, and she was completely smooth and hairless everywhere below her neck.

In return, Ellie was captivated by Olivia's body, despite the twenty year age gap between them. The older woman's body was very different from her own, being pierced and heavily tattooed. "God, I love your nipple rings," she enthused. "May I touch them?" Olivia encouraged her to do whatever she wished with them, urging her to suck her nipples and tug firmly on her rings. Ellie spotted Olivia's clitoral piercing and began to rub it, fascinated by how quickly it made Olivia swoon and close her eyes.

The girls were interrupted by a loud harrumph from Thomas, who stood naked, his cock jutting out towards them. "There'll be plenty of time for that shortly," he growled. "Before then, get on your knees and suck my cock like the whores you both are." The women giggled, then dropped to the floor in front of him and began to work on his cock and balls together. "That's better," he murmured. "Don't stop until my cum is spread all over your faces."

Olivia and Ellie worked together, swirling their tongues over the head of his penis, tracing their tongues and fingertips along his shaft and sucking on his hairless, heavy balls. All the while they made appreciative noises. For a while, the room was filled with slurping noises until each woman sank his cock down their throats, replacing the previous sounds with gargling and leaving strands of saliva dangling downwards. The girls stole kisses with each other now and then as they drove Thomas towards his climax.

Thomas took his time, relishing the joyous sensations that he was receiving. His plan was to watch the girls have sex once he was satisfied, but he was determined to cum before that. He couldn't last much longer, and began to encourage the women. "Suck that cock, sluts!" he barked. "Make me splash my seed on your pretty faces! Oh god that's good, really fucking good. Don't stop, please..... don't.... stop. Yes, yes girls, OH FFFFFUCCCKK!" he bellowed. Ropes of milky spunk shot from his dick, splashing onto the upturned faces of the two women, who knelt with their tongues out as if awaiting their reward.

On and on he gushed, producing remarkable quantities of cum and landing it on their faces, chins, necks and even in their hair. Some drops entered their mouths and they swallowed greedily, savouring the taste. Eventually he finished, pulled them closer once more, and instructed them to lick him clean before doing likewise to one another. "Give me a lesbian show, girls," he ordered.

Once Thomas was clean, he lay on the bed and watched the girls lick each other like cats grooming. Ellie was first, cleaning Olivia's face with her tongue and planting delicate kisses on the older woman's skin. Olivia returned the favour, before laying on the floor, legs open wide. "Eat me, baby, while I do you," she suggested. Ellie climbed on top of her and they began a slow, sensual sixty-nine, watched by a fascinated Thomas.

Olivia was immediately transported back to her student days at university. As she'd told Thomas, she'd had a relationship with a beautiful girl called Charlotte, who was much more experienced than Olivia, and convinced her that she was gay. The next twenty-four years somewhat disproved that, but now Olivia was rediscovering the joys of sex with another female, and was determined to make the most of it. The fact that Thomas was watching, a huge grin on his face, made it even sweeter. Submitting to his instructions while sixty-nining a hot young girl was about as good as it got.

For two hours solid the women made love. Sometimes urgently, with their fingers squelching in and out of their pussies, sometimes tenderly, kissing and playing with their breasts, and sometimes energetically, rubbing their vulvas together while scissoring. Each girl enjoyed multiple orgasms, until at last they were exhausted and could continue no longer. Thomas watched the whole thing, fully erect once more but aware that both women were now sore, swollen and entirely spent.

Olivia and Ellie climbed onto the bed and the three of them cuddled for a while, before Ellie announced that she was heading off to her own room. "I need my beauty sleep," she explained. "I've got to be alert for all those selling tips tomorrow. That was wonderful, thank you." She got dressed, kissed Thomas and Olivia, said goodnight and left.

Once she'd gone, Olivia snuggled into Thomas' arms. She felt an immense sense of calm and contentment. There were, she decided, three versions of Thomas. There was sexually dominant Thomas, issuing commands that she was delighted to follow. His masculinity and authority was something she'd craved from a man but never found until she met him. Then there was Thomas Watson, the accountant. He was technically adept, great with clients and thoroughly professional. Finally there was everyday Thomas, who was kind, funny and a true gentleman. Sure, the boundaries between the Thomases were a little blurred, but it didn't matter, since she liked them all.

Six weeks later

As a personal assistant, Olivia made very few mistakes, if any. She always checked anything that had Thomas' name attached to it, intercepted emails that he didn't need to see, and made sure that his tea, coffee and sweet treats were plentiful and as he liked them. She was not especially friendly with the other p. a.'s at the firm, but was highly respected nonetheless. "She's a bit of a prude, but she's bloody good at her job," colleagues would say, sometimes within earshot of Olivia. She would smile to herself. If only they knew, she'd think.

By the middle of the summer, England was enjoying - or was that enduring? - a sweltering hot spell. Olivia was starting to regret wearing long sleeved, high necked tops and full length trousers, but was reluctant to expose her piercings and tattoos to her colleagues. One effect of her wardrobe choices was that she was hot and bothered. She knew that she must concentrate extra hard to avoid errors caused by the heat, but made one when her guard was down.

She placed a tray of tea and custard cream biscuits, Thomas' favourites, on his desk. "Ah, lovely, thank you Olivia," he said. He picked up his mug and took a gulp of tea, before spitting it out all over his lovely oak desk. "Uuurgh!" he cried, "you left the bloody teabag in! I almost swallowed it! For pity's sake, Olivia!"

"Oh god, I'm so sorry Mr. Watson," Olivia replied, conscious that the office door was open and people could hear them. She grabbed some tissues and attempted to mop up, starting to perspire with the heat. She noticed Thomas chuckling gently to himself, before realising that he had that look on his face, the look he always had when he was horny.

"Are you all right, Olivia?" he said, loudly enough for others to hear. "You look rather hot. Do you need to go home?" Checking that no one was looking, he handed her his car keys. "Yes, I think that's best. I'll see you tomorrow," he said. "Go home and cool down. I'll clear up this mess." As she stood, he mouthed, "Give me five minutes."

Olivia waited in Thomas' Porsche in the car park, sitting low to avoid being noticed. She took the liberty of starting the car's engine and switching on the air conditioning. For a few minutes, she listened to the thrum of the car's flat six engine and enjoyed the cool air flowing inside the cabin. Soon enough, the driver's door opened and Thomas eased into his seat. "Right then," he said, "let's get you to my house where you can be properly punished."

As the car eased through the usual suburban traffic, Thomas peered at Olivia, and said, "You know, as murder attempts go, leaving a teabag in my mug, hoping to choke me, was rather lame."

"Ah, but what if I told you that the teabag contained arsenic?" Olivia countered. Thomas laughed out loud, telling himself that Olivia's sharp wit was another thing he had come to like about her, along with her open-minded sexuality. Still, enough musing. There was a game to be played.

"Well, trying to poison your boss, quite apart from being a criminal act, is behaviour that needs punishing, young lady," he replied. "But somehow, I get the feeling that you'd rather enjoy that. Does the prospect of correctional discipline turn you on, my dear?"

Olivia wriggled in her seat. "God, it does, Sir, very much so. In fact, I can feel myself getting wet just thinking about it."

"Well then, as a special treat I will allow you to open your trousers and finger yourself. Give yourself an orgasm if you feel the need, you horny girl," Thomas responded. Olivia needed no second invitation, and pulled down the fly of her sensible office trousers. As usual, she wore no panties, since they merely got in the way of any office naughtiness. With one hand she massaged her clit piercing, while plunging three fingers into her dripping pussy with the other.

For a while, the only sounds in the cabin were Olivia's low moans and whimpers and the squelching of her fingers as she masturbated vigorously. "Oh Sir, my fingers feel so nice in my cunt," she breathed. "Would you like a taste?" She offered her hand up to his mouth and he sucked them clean while keeping his eyes on the road ahead. He told her to imagine having her bottom caned while bent over his knees.

The image of such punishment was too much for Olivia to bear and she came spectacularly there and then. "Oh my god, Sir, I want that so much!" she blurted. "Discipline me like the bad girl I am! Oh god, I'm going to cum, so good. SO GOOOOD! Yes, uhuh, mmm..... FUUUUUCK!" she screamed, as she gave herself a delicious orgasm that bent her in half and made her body twist and shudder. It was probably just as well that her seatbelt restrained her movements as she thrashed around, lost in her climax. Eventually, her orgasm subsided and she became still, enjoying the wetness of her pussy, but knowing she wanted more. She stole a glance out of her window and realised they were now close to Thomas' home.

"Perfect timing, sweetheart," Thomas said, as he eased the car onto the driveway of his house. "Now, let's get you inside and give you the punishment you so obviously crave."

Not for the first time, Thomas gave thanks that he'd invested in reversible heat pumps that kept the house warm in winter but cool in summer. Although the afternoon was fiercely hot, it was pleasantly cool inside the house. The summers in England seemed to be getting hotter each year, and there was nothing more off-putting to carefree sex than rooms that were either stiflingly hot or bitterly cold. As he ordered Olivia to strip he reflected that, for the time being, she would be comfortable. Of course, the riding crop that he'd just picked up would probably change that.

To add a frisson of drama, Thomas opened a drawer in the living room's cabinet and retrieved a velvet blindfold. He instructed Olivia to stand in the centre of the room and fastened the blindfold around her eyes, securing it behind her head. He walked around her, admiring her body and commenting on her tattoos and piercings. Now and then, he flicked the riding crop against her tummy, breasts or buttocks. "If only the staff in the office could see you like this," he mused. "I wonder what they'd say." He snickered to himself at the thought, and lightly flicked the crop against one of Olivia's nipples, causing her to gasp with pleasure. "Oh, you like a bit of pain on your nipples, do you, slut?" he asked.

"Mmm, oh yes Sir, I do. Very much so, Sir," she replied. "It's part of my punishment, you see." Thomas chuckled to himself and returned to the cabinet from which he'd sourced the blindfold. This time, he selected a pair of nipple clamps. He stood behind Olivia, reached his hands in front of her, and rolled each nipple between his fingers, ensuring he gave a little tug of her rings. Her nipples grew hard and became elongated, resembling olives. Satisfied that they were fully aroused, he stood in front of her and gently pulled each nipple towards him, before attaching the clamp to each one. Olivia gasped as each one was attached. "Thank you, Sir," she said. "It hurts, in a delicious way."

Thomas moved a dining chair into the centre of the room, pulled her towards it, and sat down. "So," he said, "let your redemption begin. Show me how sorry you are by sucking my cock, like the horny bitch we both know you are."

Olivia sank to her knees and, still deprived of vision, felt for his large, hot and erect cock. Over the past few months, she had come to adore Thomas' penis. Not only was it large and impressively hard, it was also a reminder of his dominance over her. Here she was, blindfolded, on her knees, obeying a command to service her boss. Crucially, she loved it, her sopping pussy being clear evidence of how she enjoyed her submission.

For several minutes she stimulated him in every way possible. She held him, throbbing with desire, deep in her throat, before teasing his purple cock head with her tongue then sucking his large, heavy balls. Little by little, she ratcheted up his arousal, using her hands to masturbate him while sucking him at the same time.

Finally, the moment arrived that she loved best of all. Thomas stood, grabbed the back of her head and began to fuck her face and throat, forcing his dick again and again down her throat while holding her tight to his body with his strong arms. She was helpless and knew she was being used for his pleasure, which was precisely what she craved. Gurgling and slurping noises came from inside her as he approached his climax.

"Take my cock down your throat like the slut you are!" Thomas yelled. "You love it, don't you? Get ready to swallow my load, sweet whore!" He fell silent as he passed the point of no return. "Oh god, that's what I'm talking about. Oh yes, shit! Yes! Oooooh........... FFFUUCKKK!" he bellowed, his orgasm crashing through him like a tidal wave. Hot ropes of creamy cum spurted into her mouth and it was all she could do to swallow quickly enough. He continued to produce dollops of creamy cum for several more seconds, until his balls had fully emptied. "Oh, you beautiful baby, you are so good at that, so sexy," he mumbled. "Thank you, sweetheart, I really needed that."

As he began to soften inside her mouth, he removed the blindfold and allowed her to lick him clean, before slumping onto the dining chair, a big satisfied grin across his face. Olivia shuffled towards him, kissed him gently, and asked, "So, Sir, when do I get to feel the sting of the crop on my bottom?"

His answer surprised her a little. "Bend over with your bottom in the air, and hold the position. I have a couple of items I need." She did as instructed, wondering if he intended to strike her from behind. Instead, he dangled a bright pink vibrating egg in front of her. "This is going in your pussy, and is controlled by an app on my phone," he explained. "Every time I strike you, I will turn the vibe up a notch. Just as the pain becomes too much, I will order you to cum. It's punishment of a sort, but with a gloriously happy ending. Now, bend over my knees, you bad, horny girl."

Olivia swooned with lust. A dominant male lover making her buttocks sting from a riding crop, while a sex toy inside her stimulated her G-spot to orgasm was about as sexy as it got, for her at least. She eased herself over his thighs, allowing her arms to hang freely in front of her. Her pussy was swollen and still wet from her earlier orgasm, allowing him to slide the pink vibrator inside her with little resistance. God, it felt good to have something inside her. Her nipples were starting to throb from the clamps, but somehow it merely added to her arousal.

Thomas reached for the riding crop and instructed her to both count the blows and to thank him. The first impact was fairly gentle, but Thomas changed the vibe setting from zero to the first of ten. "One! Thank you Sir. Ooh, I can feel the toy. It's lovely," Olivia muttered. Thomas raised the setting to two and delivered a blow, harder this time, on her right buttock. "Ow! I mean, two. Sorry Sir, and thank you. More, please," she groaned.

The penultimate strike left an angry bruise on her left ass cheek. It was not quite enough to break the skin, and would not leave a permanent mark, but was painful for her to receive. However, the toy was buzzing furiously inside her and only had one more increment before maximum intensity. "Nine! I love it, Sir! The pain is exquisite! But the toy in my cunt means I need to cum. Please say I can, Sir, I need it so bad! Please let me cum, please!"

Thomas smiled to himself. This was turning out better than he could have imagined. Olivia was the perfect submissive, relishing everything he did to her and wriggling and twisting in his lap. "Very well, my sweet," he replied. "I'm going for full intensity now. You may cum on the tenth impact." He turned the toy to maximum, and struck Olivia as hard as he could manage immediately afterwards.

Four things combined to send Olivia flying into the stratosphere with an explosive, glorious orgasm. First, the searing erotic pain of his riding crop on her buttock, which sent a flash of agony fizzing though her. Second, the toy buried in her pussy which sent her G-spot into meltdown. Thirdly, the surge of blood and feelings as Thomas whipped off the nipple clamps. Fourthly and most importantly, however, was his permission. She was completely helpless and at his mercy. Her orgasm was his gift to her. I've been waiting for this moment for all my life, she thought.

Thomas had to admit that he was taken aback at the strength of her climax, not least the noises coming from somewhere inside of her. Olivia did not possess the strongest or deepest of voices, but now a guttural, animal howl emerged from her, quite unlike anything he'd heard from her before. She shuddered and convulsed before losing control of her insides. Fluid - which could have been urine - sprayed from her pussy with sufficient force to eject the toy across the room.

It was several minutes before she began to regain her composure. She sat upright, threw her arms around his neck, and kissed him over and over again, murmuring words of gratitude in his ears and hugging him forcefully. Thomas was becoming a little uncomfortable sat on the wooden dining chair, and decided that they should go somewhere a little more comfortable. "Why don't you go up to the bedroom, take a shower, and slip under the duvet?" he suggested. "I'll bring up a tray of cheeses, meats and crackers and a nice bottle of Champagne. If you like, I'll apply some aloe vera balm to your buttocks. Those impact marks are going to hurt in the morning, I'm afraid."

As Olivia showered, she reflected that she'd just experienced two of those three sides of Thomas that she liked so much. The dominant, controlling and sexually kinky side had been followed by the kind, considerate and loving side of him. Loving? Stop it, Livvie, she told herself. You're just his p. a. and whatever this thing is, it's not love. Don't be so silly.

Moments after she'd slid under the bed's lightweight summer duvet, Thomas appeared with a tray of treats and a properly chilled bottle of Champagne. He poured them each a glass and put the tray between them. "Help yourself," he said, before adding, "oh, and consider yourself forgiven for teabag gate." They both laughed, and for a while sat sipping their drinks and munching on the charcuterie between them. Suddenly, Thomas' expression became serious. "There's something I haven't told you," he said, his voice quiet and calm.

Thomas explained that Ellie, the girl they met and enjoyed a threesome with at the hotel, was not, in fact, there attending a sales training course at all. She was, he disclosed, a student at Portsmouth University who did some escort work as a side hustle to top up her finances. Her appearance at the bar and her willingness to join him and Olivia for some adult fun was all pre-arranged and paid for by Thomas. "You said you still fantasised about girl sex, so I thought I should make it happen," Thomas said. "I hope you don't feel deceived. I just didn't want to maintain the deception any longer."

Olivia picked up his hand, kissed it and smiled at him. "Well, if we're going for transparency, I have a confession for you too. That night when you bumped into me in the hotel bar? I wasn't on a date at all. I knew you would be there, because you'd put in your diary that you were having dinner with Tony. I called him and he let slip that he'd have to get away by eight o'clock. I gambled that you'd stay for a drink, and, well, here we are."

Thomas laughed with relief and surprise. "Oh my word, we're as dishonest as each other, it seems. Tell me, Olivia, when did you first start feeling attracted to me? Be honest now."

"Well, to get an answer to that question you'll have to do three things, Thomas. One, move the tray of food off the bed. Two, give me a good hard fucking, the sort that a submissive slut needs and deserves, and third, start calling me Livvie outside of the office. I only let a very few special people call me that."

Thomas stared at her, digesting her words. "Does that make me a very special person, may I ask?" he said. He lifted the tray from the bed and pulled her towards him.

"I think it probably does," she answered. "but first you need to use me like I'm your naughty little whore. Come on, Sir, you know what you need to do............."

As their limbs entwined, both of them banished any difficult questions to the back of their minds, and by the time their lust had taken over, the physical and the now had overwhelmed the romantic and the future. There was much that was uncertain, including their work relationship, whether Olivia might move in - bringing Buster with her, of course - and the biggest question of all: were they falling in love? Tomorrow morning, the sun would rise, as it always had and always would. The difficult questions could wait, since at that moment there was nowhere else either of them wanted to be.

The End