The Bad Young Boss

This is the long version of this story. As well as a non-consensual heterosexual sex story, it includes a lesbian humiliation side-story, which some readers have found a distraction. If the side story does not interest you, please see the short version.

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Day 1

Joanna hated her boss. He was an arrogant, selfish pig, with a big dick he was apt to put into whoever's hole was available. He was usually forcing unfortunate women clients of his father's real estate agency to have sex with him, but this week had been a slow week, and today he had made Joanna suck him off in his office. It had been so embarrassing. He had threatened to sack her, and employ someone younger. If she hadn't needed the job so much, she would have told him what she thought of him, and resigned to keep her dignity. But her husband had lost his steady job six months ago, and there weren't many jobs for women her age in this small town. Not that 44 was old, but most businesses prefer a pretty young thing on their front desks. Joanna was lucky to get this job, as her boss's father had taken a shine to her and given her the job a couple of years ago. Joanna felt it was probably only her big brown eyes combined with her shapely breasts the size of large grapefruit, and the tight blouse she wore to the interview that had got her the job, but she'd easily mastered all aspects of the work and enjoyed her work.

But now the father had started another business in the next town and Brent, his arrogant 25-year-old son was now in charge of Joanna's agency, and of Joanna. Brent was tall and flashy, and was able to impress women and men with his confident patter and easy charm. But he was self-centred in the manner of rich, spoilt kids. In spite of having a string of pretty girlfriends who dressed up for him and undressed for him, he was always flirting with the women clients. He'd managed to seduce several local women, both married and single, whom he'd take to one of his vacant houses for his pleasure. Joanna had been forced to take their desperate phone calls and make excuses for him when he callously dumped them after a few assignations.

So today when Brent called her into his office after a slow couple of days, she feared the worst. She was used to his right-wing rants about lazy, greedy workers trying to rip off their hard-working bosses. She was used to his slurs on her work and unjustified complaints against her when his arrogance drove their clients away. She was used to his ogling of her breasts and arse, even though she was almost old enough to be his mother. But she wasn't used to being taken advantage of sexually, and was therefore surprised at his ultimatum.

'You know I've been thinking we need someone younger at this agency, someone to attract the clients, someone pretty and flirty who'll make the clients feel good,' he started. Joanna felt a sinking feeling in her stomach. She thought he was about to fire her, and the family would be in trouble financially.

'But I'm very good with the clients,' she responded. 'And I always dress carefully,' she added, 'and wear attractive (meaning low-cut) tops like your father told me to.' Though Brent was sitting at his desk, he hadn't asked Joanna to sit and had left her standing in front of him. Brent glanced at her breasts, as he often did. She felt uncomfortable standing there in front of his desk while he sat behind it, brazenly checking out her curves, and left her shifting from one leg to the other nervously.

'So if you want to keep your job, I want you to come around here and show me what you're willing to do to keep it.' Joanna was initially confused about what Brent wanted. She gathered that he wasn't necessarily going to sack her, but she was unsure exactly what he wanted her to do. Brent impatiently gestured for her to come around the desk, so she tentatively walked around to Brent's side. As she approached Brent rolled his chair backwards, revealing his open fly from which was poking his throbbing erect cock. He must have been touching it while he talked to her, as it was hard and red and thick, standing fully ten inches out from his neatly pressed trousers.

Joanna's mouth fell open and she gasped, both at the size of the member in front of her, and the brazenness of the young man to whom it belonged.

'All you have to do is suck me off, and you can keep working for me,' Brent smirked, obviously happy at Joanna's shocked demeanour.

Joanna was aghast. She knew he was an arsehole, but how could he ask her to do such a thing. She was a married woman and much older than him. Did he want to humiliate her? Or was he just sex-crazy? Every part of her wanted to walk out and never come back. But her husband was doing part-time sales and was hardly making any money. Her two kids were still dependent on her - her daughter was in her final year of school, and her son was in the city at university, and could barely support himself with his part-time job.

'You can't be serious?' she asked. 'Please Mr Cunningham. Don't make me do this,' she begged the grinning man in front of her.

'I would have thought a married woman like you would jump at the chance to suck a hard young cock like this. How often does your husband give it to you? Once or twice a week? I'd give you ten hard inches twice a day if you were mine, a sexy bitch like you!'

More like once a month or less, Joanna thought. Her husband had become less interested in sex as he got older, whereas Joanna still often found herself in the mood and had to beg him to fuck her, or please herself with a quick dirty rub when she got a few minutes alone.

Had she heard right? Did Brent sort of complement her, by calling her a sexy bitch who he'd like to fuck twice a day? It was a filthy sort of complement, but it kind of indicated that he actually thought she was attractive and 'sexy', even though she was older and starting to sag a bit. Joanna had stopped feeling that she was attractive and assumed that young men like Brent did not see women her age as sexually-interesting.

'Don't just stand there like an idiot!' Brent barked at her. 'Get on your knees and suck me!'

Joanna decided that Brent was serious and would sack her in a second and get some young bimbo with no idea of customer service to replace her: someone young and desperate who would willingly suck her boss's cock to keep her job. Joanna decided that she'd have to suck this bastard's dick and swallow both his come and her pride to keep supporting her family, and so she took a deep breath and knelt down beside Brent's chair with as much dignity as she could muster. Now that she was face to face with this man's erect dick, she was even more impressed with his length and girth. She had never seen such a large cock. There was no way she could get more than a fraction of it in her mouth, Christ, she could barely get her fingers around it. She looked up at Brent above her, smirking as he took in the submissive older woman below him, with her big brown eyes pleading for a way out and deep cleavage showing her inviting breasts.

Joanna tentatively leant over and touched the bulbous head of the cock with her lips, and grasped it with her right hand. It was so hot and hard she got a shock. Her husband's dick was both smaller and softer these days. She gently poked out her tongue and licked the end of his dick, causing him to murmur approval. She put her hand around as much of his cock as she could (though her fingers did not meet on the other side) and pulled it gently towards her, at the same time opening her mouth and taking the tip inside her mouth. She hadn't had much practice giving head. She did it for her husband to encourage him to fuck her, but it was easy to fit his more slender cock into her mouth. Brent's dick was another challenge altogether. She opened her mouth wide and managed to take the cock tip inside her mouth. She heard Brent murmur encouragement. She started moving her mouth back and forward over the tip of his cock, although she had to open her mouth wide to take it. Then she felt Brent's hand on the back of her head, and he held her tight as he thrust his dick deep into her mouth until it hit the back of her throat. She started to choke, even though it was only halfway in, but Brent held her tight as he tried to force her to take him deeper. Her whole mouth was full of his thick hard dick, pushing and probing her throat. She'd never had this problem with her husband, and she struggled to free herself.

Eventually Brent relented and let her pull away, coughing and spluttering. 'How do you like it, Joanna?' Brent asked. 'How do you like a real dick in your mouth? I bet you'll want more, won't you?' he said as he tried to force his dick into her lips again.

'Please,' Joanna pleaded, 'Not so deep! It's so big! I can't take it so deep.'

Brent chuckled. 'You'll get used to it, baby. Hey, why don't you take your top off, so I can see those fabulous boobs of yours? Otherwise your blouse might get a bit messy when I blow.' Brent reached down and started to pull her blouse up.

Joanna let go of his dick and tried to push his hands away. 'No Brent, no!' she said. 'I don't want to. Stop it! Please.'

Brent laughed, as if getting her blouse off was a game. 'Come on Joanna. Show me your tits. You do want to keep your job don't you? Come on. Show me those fabulous tits you tease me with all with every day!' He kept on grabbing her blouse and pulling it up, getting it over her bra, but not over her shoulders as she struggled to stop him. Eventually he stopped trying to pull it off by force, and resorted to his usual practice of bullying.

'Stop fooling around Joanna! Take off your blouse now, or you're fired!' he barked at her.

Joanna was at a loss. She'd agreed to give him oral sex, which was humiliating enough, but now he wanted to see her breasts. What would he want next? But she still faced the problem that she needed the job so much at the moment and couldn't afford to get fired. Eventually she reluctantly nodded her head, and said meekly, 'OK, but nothing more!'

'That's better. Now take your top off for me, Joanna. Show me what a good worker you can be!'

Joanna slowly pulled her top over her head, revealing a lacy white bra which barely contained her shapely breasts. Brent smiled, taking in the pleasant view, and his cock, which had started to soften, stiffened again at the sight. Joanna reddened with the embarrassment of a man ogling her uncovered breasts so openly. But she was also aware of an excitement building in her and she could feel her nipples stiffening against the cotton material. Her nipples always hardened and became more sensitive when she became aroused, and she wondered why they felt like this way now, when this awful man was humiliating her, making her bare her breasts and suck his rampant cock. She should feel disgusted. Why then did she feel this excitement, she wondered? Her nipples were visibly pushing against her bra, making two little points. Her face reddened, and she noticed that her chest had reddened too. She hoped he didn't notice this and take it for a sign that she was excited by all this, because she wanted nothing more than to get away.

'Now the bra, baby!' Brent ordered. 'I want to see your hard, hot nipples that are pointing at my cock.'

Joanna blushed some more, knowing that he'd noticed their hardness, and hoping he didn't think she was excited by this ordeal. Furrowing her brow in a futile appeal to his mercy, she reached behind her and released her bra clip, then slowly pulled it off her shoulders so that her breasts flopped down and out a little, then hung like luscious ripe fruit for his greedy eyes. Her nipples were dark and hard and poked outwards at a slight angle from each other. When she had been younger her breasts had been higher and attracted much attention from both men and women, but even though gravity had made a slight impact, they were still stunning, especially without her bra like this.

'Not bad.' Brent grunted lasciviously, 'Not bad at all.' He reached down and stroked her hard nipple, then took it between his fingers and squeezed and pulled it a little till it hurt and she winced.

'That's more like it!' he said, and then thrust his cock into her mouth with renewed vigour.

'Yes Joanna, yes!' he muttered as he thrust his cock between her lips, deeper and deeper so that she struggled not to choke on his monster. 'I always thought you were a hot slut underneath your prim and proper manners,' he teased as he drove his cock into the O formed by her open lips. 'I'm sorry I made you wait so long. You must have been creaming your panties, hoping it was your turn. Isn't that right?' he asked as he pumped his hot cock into her little mouth. Joanna of course could not answer as her mouth was being stretched by Brent's big hard dick. There was no way she would be able to stop him now. He had stood in front of her and dropped his trousers and was holding the back of her head with one hand and her right breast and nipple with his other hand. Joanna was so glad no-one could see how he was using her. She had never had a man use her like this, like a plaything for his lust, like a warm wet hole for him to fuck furiously without thought of her feelings or satisfaction.

Brent continued to ramble as he pushed deeper into her mouth and down her throat: 'Yes, that's a good little slut. Open up for the boss's big dick! Yes you want it don't you! I bet your man doesn't give you anything like this. Open up you little slut. Oh yes! Oh fuck! Oooh!'

And then Joanna felt the hard pole inside her mouth tense and pulsate as Brent came and started to pump large amounts of sperm into her mouth and down her throat. She started to choke and tried to push him away, but he held her tight and another load filled her mouth, some escaping and running down her chin and neck and onto her boobs. She choked violently and freed herself to catch a breath, only to have another wad of sperm hit her on the forehead, splattering over her face and hair. Brent was groaning deliriously, trying to put his dick back into her mouth to catch the last drops of his massive orgasm. Eventually his dick stopped twitching and he stepped back to admire his mature secretary, kneeling topless in his office with his come caking her face and breasts and hair. He couldn't stop grinning at the conquest he had made. Now every day when he came to work, he would look at his secretary and know that she was his to have whenever he liked.

Joanna, on the other hand, was distraught and trying not to cry, not to give him the satisfaction. She gathered up her bra and blouse and quickly put them back on, then left his office without making eye contact again. She did however hear him calling after her, 'Thanks Joanna. I think we understand each other now, don't we?' Joanna only started sobbing quietly when she reached the bathroom and started cleaning Brent's gooey come off her face. It was in her eyebrows, down her cheek, around her mouth and down her chin and neck. There was some in her hair too, and she had to take her blouse off to clean the last of it from between her breasts where it had run.

It was so humiliating, and feelings of anger and helplessness washed over her. Could she get over this, and even let it add to her stock of sexual experiences, as limited as they were? She didn't know. She went back to her desk, still shaking with emotion. Fortunately the rest of the day passed uneventfully and she returned home to cook dinner for her husband and sulky daughter as if nothing unusual had happened. She couldn't tell them. Her daughter would explode in a feminist rage and call the police, and her husband would probably agree that she'd done the right thing for the family, but subconsciously think less of her for doing such a thing. She'd just have to try to hang on and keep her job until she found another one. She'd just have to suck it up, both figuratively and literally, for the sake of her family.

Day 2

The next day was Friday, and Joanna dithered about whether to wear a very low cut top, to encourage Brent to want to keep employing her, or a more modest one, to discourage Brent from thinking about her sexually. She eventually went for a moderately low cut one, and dashed off to work, wary of what the day would bring. Fortunately Brent was away during the morning, doing the books with his father, so Joanna did not see him until lunch-time when he had an appointment with a woman who was behind with her rent. The young woman, who was working a minimum-wage job, was renting a cheap flat with her spendthrift boyfriend, but was two weeks late with her rent payment and had agreed to come in to negotiate a payment plan with Brent. Brent usually arranged such appointments around lunch-time and would tell Joanna to go out for an hour for lunch and close the office while he finished the negotiations. Joanna had always been suspicious of this practice and suspected Brent of sexually harassing these women, but had turned a blind eye for the sake of her job. So today she showed the nervous, petite young woman of about 20 into Brent's office before gathering her things and closing the office. Outside however, the weather was terrible, with rain pouring down and wind blowing up the street. Joanna's husband had their car today, and she didn't feel like the 20 minute walk in this weather to the nearest shopping centre. So she quietly let herself back into her office, and decided to quietly eat her lunch there, rather than get soaked to the skin outside.

From her reception desk, she could hear the indistinct voices from the office, Brent's deep tones waffling on about responsibility, and the woman's high tones, pleading for further time. After some time the voices fell silent. Joanna tried to read her book, but couldn't help imagining the young woman inside being forced to suck Brent's large dick. She felt sorry for the girl, being humiliated by this smug bastard. Really Joanna should step in and defend the woman, but she didn't want to lose her job, so she sat still and listened. After a few minutes, she heard little cries and groans from the girl. These continued in a rhythmic fashion for a long time, becoming louder and punctuated by male groans as well. Joanna realised that they were having sex in the office, just a few metres from her. Moreover, it sounded like the woman was enjoying it, although she could, of course, have been faking it. It sounded so intimate to Joanna, who suddenly felt like an eavesdropper. The sounds of love-making soon started to excite something inside Joanna. It had been a long time since she'd had sex, especially sex with a new partner, and Joanna felt her nipples starting to tingle and her pussy growing moist, listening to the cries from the room and imagining what the couple were doing. How would such a small woman cope with Brent's large dick? How were they doing it? On the floor? On the desk? Standing up? Joanna's mind buzzed with questions.

Then she remembered that there was an old window she had discovered from the stationery room into the office, covered only by a tattered curtain. Joanna crept, heart racing into the stationery room and closed the door quietly. She moved carefully in the dark and found the window with her hands. She pulled the curtain a little and looked through. There she saw the woman, stripped naked on her back on top of Brent's desk, small breasts rocking back and forth with Brent's thrusts. Brent was also naked, and was holding the woman's legs in the air.

From Joanna's position, she could see the woman's open pink shaven pussy and Brent's thick cock plunging deep inside her slit. Joanna watched fascinated as Brent slowly pulled his cock out of the woman. It was so long, Joanna thought. How did it all fit in this small woman's cunt? Brent rammed it in hard, and the woman moaned, not in pain but in pleasure. She had her head raised and was watching Brent fuck her. Her mouth was open wide in a sort of ecstatic smile and it seemed she was full of desire for Brent's impressive dick. Her nipples were red and swollen and rocked back and forward in time with the thrusts. Brent withdrew his cock completely and started to rub it along the outside of the woman's wet swollen labia. This seemed to please the woman at first, but then she indicated that she wanted it back inside her, pointing and pleading, brow slightly furrowed. Joanna heard her pleading, 'Put it back in! Put it back!'