A Legal Matter

by uksnowy

Copyright© 2018 by uksnowy

Erotica Sex Story: An intern propositons his mature boss

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Coercion   Fiction   Workplace   .

A found story, tailored and improved.

Pamela looked up from her computer screen, over the top of what her husband calls her librarian spectacles, precariously teetering on the end of her elegant long nose, where she had been compiling notes for his next court case – a divorce with messy settlement she was sure. She felt like she was being watched. Glancing around the office she saw Kevin O’Sullivan avert his gaze, pretending to be busy with work. Ever since the previous month, when the chambers HR had signed him on as an intern, she’d caught him ogling her openly on more than one occasion. In truth, she was sort of responsible for that state of affairs: she was the one who had recommended him for the internship, and thus far, no one had complained about him. This pleased her to an extent, as she had been somewhat reluctant to recommend her son Kris’ best friend for the job in the prestigious chambers.

Kevin had been her son’s best friend for years, ever since they had joined the rugby team when they were both twelve. Over time, he’d come over to her house on numerous occasions; most visits had centred on the fact that her house had a large swimming pool in the backyard. It was there that she’d first noticed him staring at her. He would only be early teens and Pamela mid 40s.The intensity of the stares had grown as he’d matured and of course she got older. Back in the day she had dismissed his stares as the stares of a normal, horny young boy, but here he was, much later, still staring at her. If anything, he’d grown bolder.

Since her concentration was broken, she used the opportunity to go for a cup of coffee, and get away from the concentrated and quite upsetting ... to a lady, nature of the work she was doing - mega rich, habitual womaniser East European man against a stunning, silicone enhanced, glamorous trophy wife, twenty years younger. Fresh cup of coffee in hand, Pamela paused for a second in front of a window to check out her reflection and straighten out her outfit. As she was complimenting herself over her new haircut, which had her steel grey hair cropped trendily close, as her hairdresser had advised, and which had cost quite a pretty penny, the thought of Kevin’s stares popped into her head. She caught herself thinking about him and his piercing brown eyes more and more often nowadays and not just in the work place. She rationalized that she exercised regularly, jogging three times per week, so why not relish the attention. She smiled to herself before dismissing his horny stares, they were there now, returning to work.

Of course, there had been the one time when, in the file room, she’d had to squeeze past him. She was very busy and in a hurry, so she hadn’t registered the event too well- her attention had been on the set of files she needed. But, could she have felt his erection that day, pressing against her? Was he that bold? Pamela snapped out of her day dream. She wanted to get done with work early so she could plan and prepare for the upcoming weekend’s pool party at her house.


Kevin had been waiting impatiently for the annual shin dig weekend to arrive ever since his best friend had told him about it, not long after he’d started his internship. For him the internship was one of the best things that could have happened - the company was a good one, this job would enhance his resume and, more importantly, he’d figured, he could hang around lush elderly and rich Pamela Ponsonby-Smythe more.

She had been his hot, wet dream for as long as he could recall being interested in girls. He’d always found her attractive, although he’d never quite understood why, because her allure remained to this day ... and what she must be nearly 70 now. Maybe it was that he’d seen her virtually naked all those summers, as she paraded around her pool in her assorted bikinis, letting the sun and whomever was present, lavish her with attention. Maybe it was a simple stereotypically cultural thing - Pamela was a MILF although actually a GILF, with three known grand children and he wanted to fuck her. Maybe it was the taboo of her being his best friend’s mum, almost like a second mum to himself, in a way.

Ah, his mum, dear sweet always there, shop assistant Betty, but not there after her untimely death when he was 12. One of his cousins had cheekily dared him to look at her knickers to see if there was cum on them. Cousin Edward had shown him his own mother’s knickers one day when visiting and Kevin didn’t do much more about it until the dare. He had found mysterious stains evident, not knowing what to look for until his cousin advised and explain what cum was and since then he had relished the discovery, then the delicious odours and scents therein, because of the porn his evil cousin had revealed ... The fact that Pamela was the same age as Betty and as equally attractive was the spur.

He found Pamela attractive and wanted to smell her knickers and have her, now he knew the pleasures of shagging. He’d dreamed of an opportunity to make a move, but, other than the one time when he’d legitimately had to squeeze past her in the file room. Her back had been towards him; she was looking for a folder and he’d made sure to press himself into her in accident. That, however, was as close as he’d ever got near to fulfilling his fantasy ... He’d engraved the memory of her firm, tight arse, as always in the office in a skinny black pencil skirt, pressed against his cock, but, he’d hoped for more by now. He wanted more. Pamela had occupied a central place in his mind ever since he’d first seen her wearing a small string bikini out by the pool. The way her fair greying pubes were sprouting at the side thrilled him. Starting that day, which had ended with him cumming three times to thoughts of her filling out that hot bikini she had been wearing, she had been on his mind on a daily basis, if only when he was jerking off. However, he knew himself to be an optimist and figured that this party might be the right time for him to really make a move.

He arrived at Pamela’s house just as her geriatric husband, Bernard Ponsonby-Smythe, the principle of the global law firm was offering cocktails and beer. It was a very hot day and the drinks, whatever, did look very appealing. Everybody seemed to be a little tipsy. Bernard appeared to have had a few too many already, which was understandable, since he was in charge of making the drinks. He found out to his great surprise, that his best friend Kris wasn’t present, apparently because he’d got a fresh date with a hot chick. This was news to Kevin, but he silently wished his friend the best of luck on his quest – he knew of the hottie. Would his friend have really been aware of the fact that Kevin wanted to bang his mum? Probably not. Well, what Kris didn’t know, wouldn’t hurt him, Kevin figured. Besides, they’d both lusted after mature women, even going so far as to make a pact to double team their university modern language teacher, Ms. Slivovitch. Nothing had ever come of that, but they’d talked a good game.

He smiled as he made his way towards Pamela to say hello. As he got closer he noticed that she seemed slightly tipsy. She’d just emerged from the pool and the figure hugging bikini looked vacuum-formed across her body. The chill rising from the manicured warm water affected her because her nipples were straining against the fabric and she sported a superb camel toe. The bikini was blindingly white and his eyes as he drank in the image of her cunt slit, searched for stray hair but there weren’t any ... She welcomed him with a hug ... which he ... and funnily she, thought lasted a bit too long. She apologised if his shirt and shorts were damp after the hug, then offered to get him a drink, as she was going to get one herself. Kevin had an Eureka moment right then: perhaps the key to Pamela lay in booze, she was very tottery and, as an ex-university graduate, he knew all about plying girls with booze. Severely denounced and punished if found ... but hey! He tried to make sure that her glass was never empty after that point.

The party progressed at a fast clip, the sole marker of the time’s passage being the flow of margaritas and real ale etc. A couple of hours later, Kevin realised that Pamela had disappeared from the party. Maybe she’d wanted to escape the heat, and had gone inside the house. He noticed that everyone was pretty drunk by that point, a result of the heat and the booze mixing, whereas he had been judicious for a change and on a mission. Most of the wealthy guests had drivers waiting, but he had to be careful. He took stock of the situation and decided that it was the time to act. He entered the house, catching a glimpse of his hostess as she headed up the stairs. Quickly he closed the gap, just as she was entering a spare bedroom.

“Can I help you with anything, Pamela?” he asked, barely managing to contain his trembling voice. His desire had taken hold of him, but perhaps he shouldn’t force things yet. It wasn’t the first time he’d used her first name, especially since they’d started working together. But this was different. He wanted to assert himself if he was going to make his move.

“Oh, Kevin, you caught me. Is the pool toilet occupied? There’s another through the ... oh never mind ... you know where things are. I was just trying to get out of the heat, and this room is the coolest one in the house, to change” she replied, wobbling and seeking the support of a door frame.

He continued. “No it was just that you looked a bit ... you know peaky ... you OK?”

He saw her gaze shift to the visible bulge in his shorts. A cheeky smile drifted across her face.

“Anything I can help you with, Kevin?” she said, with a hint of sarcasm, but he could see her staring at his growing crotch.

“No not peaky as you put it most nicely ... bit tipsy is the term, but hey!” she waved airily.

“Pamela, I’ve always been very attracted to you,” Kevin said as he stepped to within a foot of her, “And you know it.”

“Yyeees? but, I am old enough to be your mum, your grandmum. What ... what would ... Kris think? What would Bernard think ... the boss?”

His words had made her blush, even as she nodded her agreement. She caught herself mid-nod: Her protest, however, came with no energy. She wasn’t convinced, and she was not convincing him either. He had shuddered at the mention of the Crown judge’s name.

“Quite frankly, I want you. Here. And. Now. “ His tone was very commanding, but he could see it soothed her at the same time. He had to take charge of the situation, before she’d slip through his fingers. Besides, the more time he spent thinking about her, the more he wanted to dominate her - to make her submit to him. Circumstances were forcing him to take charge. He moved closer, until he was sure he filled her entire field of vision. She stepped back into the room. He followed and closed the door. Kevin’s hand was stroking the back of Pamela’s bikini bottoms. He could not believe his luck. His fantasy, what had become his damn near obsession, was about to become reality.

As his fingers found her concealed mons, he broke off the kiss just long enough to say “Pamela, I need to fuck you, right now.”

The words struck her like a bag of bricks, and hearing him say them raised the tension for her.

“But, Kevin, I’m married. I’m old III.I.I... !” she protested even as her hands were fondling his tight arse and his were probing inside the seam of her bikini.

He silenced her words with another kiss, while his fingers pushed aside the thin wedge of material covering her crotch. When he touched her fuzzy pussy, her core, Pamela’s desires reached a fever pitch. She had enough sense not to tell him to wear a rubber and to point out the night stand where she’d placed a packet of condoms. Her brother in law and wife were at the party and she’d prepared this room for them, knowing the old buffer, all of 41 years, but still a buffer, was so forgetful. Travel bags and one or two items of clothing were evidence of their occupation. She lay down on the edge of the bed and he joined her. There was little foreplay.

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