Lou Meets His Boss

It was approaching again, the annual summer work party. Matt had always had a great time there. His boss, John, knew how to throw a great party. His huge house was practically made for it, with its big open back garden. If the weather held, there would be a barbeque, with dozens of guests all having a great laugh.

Only this year was different. About six months ago he had started seeing Lou, and he’d fallen for her completely. She was invited to the party, and Matt was somewhat apprehensive about his work friends meeting her. She would create a good impression, of course; it wasn’t that. He was more worried about what they might tell her! They knew about her, but now it was time to face the music.

Of course, Lou, ever the social butterfly, was looking forward to the party. The opportunity to meet new people was always a big thing for her. As was creating a good impression, which meant she’d gone out and bought a whole new outfit for the occasion. Earlier that weekend, she’d modelled it for Matt in her bedroom. It was a gorgeous summer dress; blue with white flowers. It was low cut enough to show off a hint of her 34b boobs, and short enough to make one realise that she had a great pair of legs. Matt simply enjoyed the view as she paraded around in it, braless, and adding a pair of heeled sandals for good measure. The smile on his face had told her exactly what she needed to know. She looked spectacular.

The day arrived, and Lou was bursting at the seams to get to the party. She got ready and headed down the stairs where Matt was waiting for her. He greeted her with a smile, and pressed his lips to hers.

‘You look stunning’ he told her, which was greeted with a thank you and a twirl, causing her dress to ride up and show off the sheer blue thong she had donned for the evening. Matt laughed, saying…

‘Just be careful doing that later!’

She blushed, and giggled, and they made their way to the car, with Matt driving out of town and into the country where John lived on his estate. There were plenty of spare rooms at John’s, so Matt and Lou had taken up the offer of a bed for the night. Upon arrival, there was a guy waiting to take their bags up to their rooms. He opened the car door for Lou, his eyes dropping between her thighs as she stepped out. As she did, she noticed his gaze, and gave him a coy little smile as she realised that his eyes were taking in the thong that left little to the imagination. Matt was waiting for her by the door, taking her hand in his, and teasing…

‘Seems that dress has made you popular already’

She simply let out a little laugh, saying ‘Hey, I don’t see you complaining either. Besides, I didn’t have you down for the jealous type’

The weather had indeed held, and most of the hundred or so guests were out back making the most of the waning sun. A long table held all sorts of drinks, from champagne to beer to every sort of liquer imaginable, with attractive young ladies doing the serving. Close by was another table laden with food, and next to that, the huge grill; the smell of cooking meat was thick in the air.

Matt stepped out with Lou, who had heads turning with every step. Part intrigue and part leering, Matt mused, but it was something of a compliment to him. He waved over at a few familiar faces, and ordered himself a beer and a G&T for Lou.

‘So, what do you think?’ he asked her.

‘Oh I could definitely get used to this’ she announced, eyes wide, taking in the surroundings.

‘He has about seven cars you know. Incredible’

‘How can one person get so rich?’ she asked

‘He has the gift of the gab, and takes risks. And he got lucky! Fair play to him, he pays my bills!’

They walked over to a nearby ring of chairs, where two of Matt’s closer work friends were sat with their girlfriends. Matt introduced Lou to all of them. Mike & Sarah, and Paul & Mel. As ever, she created a great first impression, and was happily chatting away with the girls in no time, leaving the guys to get down to the serious business of talking about football.

The girls announced that they were going to top up their drinks supply and get some food. As they were helping themselves to the free champagne, Sarah nudged Lou, and pointed across the garden.

‘There’s the man himself. The boss man’ she said, as Lou followed the end of her finger, until her eyes came to rest on the guy in question. He looked just short of 50, in a well fitted suit, and held himself with a reassuring aura of self-confidence, and had a smile that made him instantly likeable. Lou could see why he was so successful.

‘You can put your tongue back in’ Sarah said with a chuckle.

‘Oh, I wasn’t….’ Lou said, trailing off dreamily

‘Leave her alone Sarah’ Mel chipped in ‘He is quite something isn’t he?’

Lou gave a little smile ‘He seems nice’

Sarah pressed on with her teasing ‘So you can join the two of us in agreeing you’d drop your knickers for him in a second!’

That drew joint gasps, and giggles from Lou and Mel, but there was certainly no arguments as to the accuracy of her statement. At that point, he looked up at them from across the garden, and fixed them all with a stare and a smile. More giggling, and plenty of blushing ensued.

Dusk came and went, and night time began to settle on the party, which was in full swing by now. The three couples were back in their ring of chairs now, all pleasantly drunk and having great time embarrassing one another, and themselves. The garden was nicely illuminated, creating a perfect party atmosphere.

At that point, John appeared with a friend, asking if we’d mind his company for a while. He was pretty well liked and no-one disagreed, so he and his friend pulled up a chair each and joined in the conversation, which was a little more guarded, for a while.

‘So it seemed pretty raucous over here’ John said ‘Sounded like I was missing out’

There was silence for a short time, before a tipsy Sarah blurted out ‘Mel was telling us all about her and Paul’s bedroom habits’, drawing laughs from everyone but a clearly embarrassed Mel.

‘Well don’t let Mark and I get in the way of a good story!’ laughed John, but Mel wasn’t so forthcoming all of a sudden, before to Matt’s surprise, Lou piped up…

‘We were talking about favourite sexual positions’

John’s piercing gaze settled on her ‘Is that so? And what is yours…. Oh you must be Lou’ he said, the penny dropping, and his eyes running up and down her body. She returned his smile, saying…

‘I like reverse cowgirl’, without looking away. Matt frowned at her, a little confused, seeing a new side to his girlfriend for the first time. John gave her a hint of a smile…

‘I’m not familiar with that one, do explain’

‘Well, I’m on top, but facing away from you, instead of facing towards you. It means you get a great view of my bum!’

Matt sat there, noticing the use of word ‘you’, and laid his hand on her thigh, almost protectively, as John sat there stroking his chin…

‘I’ll have to try that some time. It sounds like it could be a lot of fun’

‘You should’, replied Lou

At that point, Sarah suggested another trip to the bar, and John put in a request for a beer. Matt was a little annoyed at his boss for seemingly trying it on with Lou, but it wasn’t like he could really say anything, was it? Lou stood up, with John enjoying her cleavage as she did, ruffled Matt’s hair, and followed Sarah.

At the bar, Sarah turned to her excitedly…

‘Oh my god Lou, he so fancies you!’

‘Noooo, no way, he’s just joining in the conversation!’ she replied.

‘He is doing some serious flirting, and so are you!’

Lou laughed ‘Ok, maybe a little, but it’s all just a bit of fun!’

Upon their return, Lou handed John his beer and John slapped his knee for her to sit. She shot Matt a questioning look, and he simply shrugged, so she sat. From where Matt was sat, he could see a hint of Lou’s knickers, and he was sure he wasn’t the only one judging from the looks she was getting. Unknown to him, John’s hand came to rest on Lou’s hip, on Matt’s blindside. Lou didn’t give it much thought, it seemed like the obvious place for him to rest his hand.

The conversation continued, with the group finally coaxing out of Mel that she loved doggy style sex. Matt was again unaware of the soft circles that John’s hand was drawing on Lou’s hip, and that he was whispering into her ear…

‘What do you think of that one?’

Matt saw her answer even if he didn’t hear her say ‘Depends on the person doing it. But I need a hand around the front to be able to cum’

He wanted her to move off his knee, but he didn’t want to annoy the boss. What a terrible situation. One that was threatening to ruin his night. Lou looked at him occasionally. He couldn’t say for sure, but she looked like she wanted to be saved. Little did he know that John was slowly but surely turning her on. She was in control though. Enjoying it more than she should with her boyfriend sat yards away, sure, but in control. The light stroking on her hip was harmless, let John think he was getting away with it.

The conversation turned to Sarah, who was asked about the naughtiest thing she’d done, and as she was telling everyone about the threesome she’d had at university, Lou found herself becoming more and more turned on. John’s hand trailed slowly down, over her leg, to the hem of her dress, as he asked…

‘Have you ever had the pleasure?’

‘Nuh uh’ she replied, gently pushing his hand away with a wry smile.

‘You should’ he replied.

‘Oi! That’s bad!’ she hissed as he tried his luck once more.

‘I know’ he said, smiling confidently up at her, once again trying his luck.

She didn’t dare look over at Matt, but nor could she resist John any longer. She tried to look sincere and interested in Sarah’s story, as John’s hand slipped under the hem of her dress an upwards, ever slowly upwards. She stifled a moan as his fingertips found the warm, damp fabric of the crotch of her thong. His slow teasing was sending her over the edge. She glanced a look over at Matt, who was clearly oblivious.

She soon found herself ever so discreetly pressing back against John, and to her surprise, found him slowly growing beneath her. She thought he was fully hard, but then he carried on getting bigger, leaving her to speculate wildly about what he was hiding in his trousers. By the time he’d slipped his fingers inside her thong, she was covering up an orgasm within seconds. She exchanged looks with Paul on her direct right, who could see what was happening to a degree, and gave him a pleading look to remain quiet. She felt guilty, but this man was irresistible! All she wanted to do was please him.

John removed his hand and let it rest on her hip once more, whispering into her ear as Sarah was finishing up her account…

‘You know, we’re almost in that reverse cowgirl position you’re so fond of.’

She giggled in response, and wiggled her bum into him a little more, teasing him some…

‘Wouldn’t you like to know?’

‘I’d say that was a foregone conclusion,’ John replied, bouncing her up and down on his knee a couple of times.

Matt was keeping a watchful eye on them, and things were getting too comfortable for his liking. He was oblivious to the fact that John had just made Lou come, but to him it appeared as though she was getting into the harmless flirting thing a little bit too far. He strove for a way to break it up without upsetting either one of them. Alas, nothing came to him.

Lou was feeling really rather drunk now. Her head was partly spinning because of this, and partly with the lust she was feeling for John. She knew her restraint was weakening, that her inhibitions were getting lower by the second. The cock beneath her was full grown now, and she wanted it. Badly. She pushed her bum back into John’s crotch once more. Only this time, it wasn’t so well hidden, and as she looked around, her lust filled eyes met Matt’s. She should have been sorry. Some small part of her was, but that part was current being drowned out by the part that was aching to feel John inside her.

The eyes of the group were on her now, and as she looked directly at Matt still, she half closed her eyes, bit her lip, and rocked back into John once more. Her dress had ridden up by this point, and her blue thong was there for all to see.

Matt was furious, he watched on, helpless. He locked stares with John, who offered no apologies, but simply, rested his hands on Lou’s hips and aided her, until she was slowly, drunkenly gyrating into him. He knew he should stop this; he felt like walking over there and punching his boss square between the eyes, but he didn’t. He froze. Even as Lou spun to straddle John’s lap, his hands going under her dress to expose her bum to the group, and she locked lips with him.

At that point, John stood and said his goodnights, taking Lou by the hand and leading her away to the pool house. Matt sat there, aghast, pleading…

‘Lou, no. Not that, you can’t.’

‘We’ll talk later,’ she slurred back at him, before tottering away with his boss.

The party had died down somewhat by now, and there was an awkward silence in the group. Clearly nobody knew what to say to Matt, so almost as one, they upped and left, leaving him sat there by himself to reflect on what had just happened.

John pulled Lou into the pool house, then turned and pushed her up against the door, kissing her hard, letting his hands roam all over her body. As she smiled up at him, he growled…

‘I’ve had my eye on you all night.’

‘I noticed,’ she replied coyly.

‘Well you didn’t seem to mind.’

‘What is there to mind? Getting that sort of attention from a hot, successful older guy. Every girl’s dream.’

‘So those flashes of the knickers, they weren’t an accident huh?’

‘That sort of thing is never an accident,’ she grinned.

‘Does Matt have any idea you’re this filthy?’

‘It’s there for him if he wants it, he’s just never reached out and grabbed it.’

‘Like this?’ he said, reaching down between her thighs and cupping her pussy tightly in his strong hand. She squealed, arching her back against the door and moaning…

‘Exactly like that.’

His fingers expertly worked her once again, two of them pushing up into her moist cavern, before being pushed into her mouth, before she willingly sucked her own juices from them. She then dropped to her knees, smiling up at him, and undid his trousers. She knew it was going to be big, but as it sprung from his boxers, a full 9 inches, she couldn’t help but say…

‘Oh my god!’

Covering her mouth with her hand, with a bit of an excited giggle escaping.

‘I get that a lot,’ John said, smiling down at her.

Seconds later she was running her tongue along his shaft. So long, thick and smooth. She loved the way his head tasted on her lips. She struggled to fit it into her mouth, but she eventually managed, and started to suck his first few inches. Never had she gotten so much pleasure out of giving a blowjob. His moans told her he was enjoying himself, as his shaft became slick with her spit. The thickness meaning that some drops were falling down onto her chest, trickling between her boobs. She wanted to make him come. She wanted to please him so much. She sucked harder, until at last he pulled out her mouth, both of them gasping for air.

He picked her up and carried her to a nearby sofa, where he set her down, straddling him once more. Once there, he pulled the straps of her dress from her shoulders, her 34b boobs spilling out for him to suck and kiss, roughly. ‘This is how sex should always be,’ she thought to herself. She stood, and pulled the thong from her waist, downwards, feeling it stick to her pussy before coming free. She stepped out of it, and back onto John’s lap.

She could feel the head of his cock rubbing around her clit as they kissed. A brief thought entered her head. She still made Matt use condoms when they had sex, maybe she should…. But she was already reaching down and guiding John’s amazing, bare shaft into her wet hole.

Her mouth opened in a silent scream as she felt every muscle in her pussy resist his thickness. This was so much more than she was used to. Gradually they relaxed, and he was able to slide ever more of his dick into her, exploring parts of her pussy that had never been touched. She met his eyes as he filled her completely. He gave her a knowing smile. She returned it, as she slowly began to rock on his dick.

She felt so lucky to be here, now, fucking him. Almost like it was a privilege. How had he managed to have such an effect on her? She had no idea, but this was already the best sex of her life, as she increased the speed of her gyrating. His strong hands grasped her bum hard, squeezing and pulling apart her bum cheeks.

It came from nowhere, but suddenly she was coming, and moaning. Loudly…

‘Fuck…. Fuck… Oh my GOD! FUCK!’

And she was riding him for all she was worth, her tits bouncing up and down as she came all over his fantastic dick, her nails cutting trenches in his back as she held on for dear life.

Out in the garden, Matt could hear his girlfriend’s screams as he sat alone, unable to rouse himself to move. He’d never know her to do that before. God knows what John was doing to her in there, but she was clearly enjoying it. He was full of hate. Hate for her, for his boss, but mostly, hate for himself. He could have stopped it, yet he had realised something. He hadn’t wanted to, not deep down. It had only dawned on him as he gripped the stark reality of the situation. His girlfriend was fucking his boss. He repeated it over in his head, and he was shocked to find himself becoming erect. He… he liked it! He liked it and he hated himself for it.

In the pool house, Lou had assumed the reverse cowgirl position, and was riding John furiously. He sat there, watching his cock repeatedly disappear into this stunning girl that was half his age. He sucked his finger, and nonchalantly rubbed the wet tip around her exposed asshole. She answered with a moan and a look over her shoulder…

‘Do it,’ she begged. So he obliged, slowly slipping his digit into her tight bum. This triggered off another orgasm. He felt his own balls tighten as her pussy gripped his dick. He held on tight and groaned loudly, emptying himself into her as she milked every last drop from him. She then collapsed backwards onto his chest, catching her breath as she reflected on the fucking she just received.

He lifted her small frame off him, and re-dressed himself…

‘I need to say goodbye to a few people. Meet me in my room shortly, and we’ll go again.’

Her face lit up as he strode out, watching her straighten her dress. She was his, for as long as he wanted her.

Matt saw John walk out from the pool house. He put his head down and ignored him. Minutes later, the door opened again, and Lou stumbled out, her blonde hair in disarray. She spotted him and walked over, sitting opposite him…

‘Hey,’ she said.

‘Hey.’

‘Thought you’d be gone.’

‘What can I say? I couldn’t tear myself away!’ he said bitterly.

‘I…. I don’t know what happened…I just…’

‘Just decided to act like a total slut,’ he said interrupting.

‘He just has this way…’ she said. Her pussy was still tingling.

‘I noticed.’

‘What’s that supposed to mean?’

‘I heard you in there.’

‘You were listening?’ she said, frowning.

He leaned back in his chair, and looked away. It was then that she noticed the bulge in his trousers.

‘Matt… why… why are you….’ She said, looking down at his crotch.

‘I dunno, it just happened.’ he said through gritted teeth.

‘Don’t you think that’s a bit… strange?’

‘What, that you fucking my boss like a whore turns me on? Yeah, it’s a little weird!’

‘Well, it’s ok. I guess. Some people like that sort of thing, I heard.’

‘Yeah well I’m not one of those people. I’m not some sort of psycho that’s into swinging and all that shit,’ he said angrily.

‘How do you know?’ she asked, head tilted to one side.

‘I just do.’

‘So if I told you I just came three times and he has an amazing cock, you’d not be bothered?’ she asked.

The look on his face gave him away. He shook his head, but he was a terrible liar. She liked this game, so she asked him…

‘What if I showed you what he did?’

With that she leaned back in her chair and opened her legs, showing him the stream of thick cum leaking from her pussy, with a long trail half way down the inside of her thigh. He looked for all of two seconds, before he lifted her from her chair and he was on top of her on the grass. She felt his cock push up into her already used pussy and he was fucking her furiously. She put a hand on his chest…

‘Babe, hang on, stop… This, isn’t really doing anything for me. I’m a bit… stretched right now. Maybe give me a lick,’ she said with a devil of a smile.

He was as eager as she’d ever seen him, and she smiled up into the night sky as she felt him lick the excess semen off the inside of her thigh before burying his face in her pussy. He went for a few minutes. She didn’t come for him, but it was still the best sexual moment she’d had with him. Finally clean, she stood, and told him…

‘I have to go. John wants me for the night. I’ll see you in the morning.’

She leaned into him and kissed him…

‘And I’ll tell you all about it.’