The Bad Young Boss

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Joanna watched fascinated by the intimacy, guilty about observing other people's sex and strangely excited herself by what she was seeing. Her own pussy was burning up as she watched this big cock stretching another woman's cunt. Her clitoris was hard and she could feel her sexual juices flowing into her knickers. Guiltily she reached under her skirt and inside her panties to stroke her hot little button. It felt so good, and so wicked at the same time, but she couldn't help herself. The couple had changed positions now. Brent was sitting in the chair and the woman had climbed onto his lap facing him and away from Joanna. Joanna watched transfixed as the young woman lowered herself onto the long, thick cock, taking it almost all inside her. Then she rose up slowly and the cock reappeared, all red and covered with her juice. 'My god,' thought Joanna. 'I've never done this with Harry!' It looked so good.

The woman was groaning as she ground her cunt up and down this big dick. Then she started to buck like crazy and scream with her head thrown back as she came, shouting 'Oh Fuck! Oh Yeah! Oh Fuck! Oh my god!' Joanna slipped her fingers inside the wetness of her pussy and thrust them deep inside herself, imagining they were the thick cock she was watching thrusting in and out of the young woman in front of her. Joanna couldn't contain herself, and an audible gasp escaped her as she started to come, but her gasp was masked by the noise in the office and no-one heard her. She felt the waves of pleasure sweep through her, up and down her spine and all through her tummy. Still she didn't stop and thrust her fingers deep in her sopping cunt, while rubbing her clitoris franticly with her other hand. She came again and again, until she sank to the floor and knelt there panting in the dark.

When she at last stood up again and looking through the window, she saw that Brent had bent the woman over his desk face down and was now fucking her hard from behind. Joanna knew that she should leave now before she got caught, but became fascinated by the scene in front of her: Brent holding the woman's hips, the big dick ramming into the woman and pulling out only to ram in again, the young woman holding on to the opposite side of the desk and groaning with pleasure at each thrust. Joanna knew she shouldn't, but her hand crept back inside her soaking pants and she started to rub her clitoris in time with Brent's thrusts. She quickly started to come again and closed her eyes to feel the pleasure of it. Then she heard Brent groan loudly and she knew he was coming inside the young woman's cunt.

Joanna opened her eyes and took one last look at their trembling bodies before carefully closing the curtain and tip-toeing out of the room. She managed to cross the reception area and opened the door. The rain had stopped temporarily. After looking outside, she loudly closed the door, as if she was returning from lunch. She then went to the toilet and straightened her skirt and blouse which had become quite dishevelled in the storeroom. Then she washed her come off her hands, after taking a few seconds to appreciate her own sex smell in which she took a secret, guilty pleasure.

As she returned to her reception desk, Brent's office door opened and Brent emerged looking inquisitively at her, before ushering out the young woman and saying loudly, 'So you have one more week to pay the rent in full, Tracey. Otherwise we may have to take legal measures.' The young woman looked up at him and nodded meekly, in a kind of post-coital vagueness, as if she didn't know if she'd been done a favour or taken advantage of. When she left, Joanna casually mentioned that she'd just got back from lunch a couple of seconds earlier, and Brent seemed reassured that his sexscapades had not been overheard. About 20 minutes, Joanna overheard him arranging a date with one of his girlfriends for that evening, and shortly after that he left for an early break before the weekend, leaving Joanna to deal with all the 'Friday specials', those difficult customers who come in just before the weekend, with some time-consuming request that meant a late departure home.

Day 3

Over the weekend, Joanna desperately searched for another job, but most jobs for women asked for school leavers, and those that didn't specify age in the advertisement soon made it clear on the phone that they were not looking for a 44-year old. The situation was even more dire than Joanna had imagined. When Harry asked why she was looking, she truthfully told him that Brent was a real bastard to work for, omitting the sexual side of things that was the immediate problem. So on Monday, Joanna returned to her job with a heavy heart, knowing that there were no real alternatives for her, and that, when Brent eventually demanded intercourse with her, as he surely would, the pig, she would be forced to give in, and she would have to open her legs to let his big cock to have its way with her.

But there were other thoughts in her mind as well. She couldn't get rid of the image of Brent and the woman fucking so furiously and luridly in front of her. She had thought of the details of their sex over the weekend, and had become aroused again. She was also shocked by the fact that she had been turned on by watching two people fucking and had actually masturbated herself to multiple orgasms while she watched. Why had she done that? It was something so completely out of character for her, and that she didn't understand herself. She knew she had a higher sex drive than her husband, but she had never taken such a risk before.

On Saturday night, she had become so aroused thinking about it, that she had sucked her sleeping husband's cock until he woke up agreed to fuck her. Moreover, she had done something else out of character when she turned him on his back, climbed on top of him and rode his cock to the biggest orgasm she had had with him for years. Afterwards they were both surprised by the strength of her orgasm. She told her husband it was probably the release of work-related stress, but she admitted to herself that she had been aroused watching others have sex, and that even sucking Brent's impressive cock had awakened a desire for sex in her. She could not admit it to herself yet, but something within her found the prospect of being fucked by a young man with a large cock arousing and a thing to be looked forward to, even though it conflicted with her general dislike of her boss and his arrogant disregard of others in general and her in particular.

So it was with all these conflicting feelings that Joanna arrived at work, nervous about what she would be called on to do, and how it would affect her. Brent arrived a little later, and was civil, even as he ogled her breasts on the way to his office. About an hour later, an attractive young brunette college student came in looking for a small flat to rent. As Joanna started to discuss the various properties, Brent appeared and convinced the girl to check out a lovely flat downtown. He left with girl, giving Joanna a complicit grin as he left. When they returned some 90 minutes later, Brent announced that he had approved the girl's application despite her lack of references. The girl had the same vague, uncertain look as Tracey the week before, and Joanna was convinced that Brent had talked her into sex as a condition of getting the apartment. 'He's such a slime!' Joanna thought.

The girl made an appointment to come back and pay the deposit the next day, and left. About 20 minutes later, Brent called Joanna into his office.

'Well that went well!' he announced. 'Another satisfied customer.' Joanna bit her tongue and didn't question his unprofessional behaviour. But worse was to come.

'Joanna,' Brent ordered. 'Come around here and clean me off!' Joanna was initially confused but as she came around the desk, Brent stood up and unzipped his trousers. Joanna's heart sank. It seemed as if blow-jobs might become a daily chore for her now. Brent opened his fly and pulled out his cock. Although it was not erect, it was still long and thick. Joanna sank to her knees in front of her boss.

'Take off your blouse and bra, Joanna!' Brent barked at her. 'Unless you're thinking of quitting?'

Joanna reluctantly but submissively pulled her blouse over her head, then took off her bra, and was rewarded with a grunt of approval or admiration from her filthy boss. She took hold of Brent's flaccid cock, which seemed to have grown somewhat since he took it out, and put her lips around the tip. She felt the cock stir and lengthen a little. She noticed that his cock looked a bit dirty with a gummy film of something on it. As she took a bit more of his hardening dick in her mouth, the smell of pussy hit her and she realised that Brent's cock was thickly covered with the young woman's juice. He had fucked that innocent young woman and now he was asking her to lick his cock clean, just to humiliate her. Waves of revulsion swept over her, both for Brent's callousness and for the dirty organ he wanted her to lick clean.

'Come on baby. Do your job. Lick my dick clean. Swallow it down like a good slut. Surely you've tasted pussy before, haven't you? I thought all schoolgirls were licking each other out from the time you got hair down there, like randy sluts waiting for a good hard dick to straighten you out.' While Brent said these dirty things, he held the back of Joanna's head and forced his dick deeper and deeper into her mouth. 'Oh yeah baby! That feels so good. Can you taste what a hot little bitch she was? She looked all sweet and innocent, but she dropped her panties soon enough when she saw the size of my dick. Oh yeah, take it deep Joanna. I know how much you like it! She lay back and spread her hairy cunt and I fucked her deep and long till she was screaming her head off. She was one hot bitch, like a younger version of you. Have you got a hairy cunt like her? Have you? When are you going to show me your little flower, eh Joanna? When are you going to spread it for me and beg me to fuck it?'

While he carried on his dirty talk, he thrust his now completely hard cock deeper and deeper into Joanna's mouth and she struggled to breathe, let alone give him pleasure. As her face was pushed up against his pubic hair, she was forced to smell the thick layer of cunt juice that coated the base of his cock and pubic hair. Tears ran down her face as she struggled to stop him degrading her like this, but he was used to women crying and thrust even farther, penetrating her throat and causing her to gag. The intense smell of cunt, the lack of control, the violence and the humiliation, all these things brought her past back to her, a past full of the shame she had buried deep within her.

Suddenly she was back at high school: a happy, studious, shy student in her final year, looking forward to going to university and making something of her life. But one day she fell into the path of Veronica O'Grady, and her life changed. Veronica was a year older and repeating the final year after failing the year before. Not that she wasn't smart, but she was more interested in sport and bullying. Veronica was tall, thin with hardly any tits, and tough. She was the captain of the Girls' Basketball team and the Girls' Hockey team. She was a keen and talented athlete who won most of the school races and other events. But she had her little gang of butch girls who liked to pick on other girls at random.

So one day while Joanna was hurrying down the hall to class, Veronica's foot tripped her and Joanna fell face-down in the corridor, books and pens everywhere.

'Well, who's this clumsy little slut then?' Veronica snarled at her. Joanna looked up at her disdainful face, trying to make sense of what had happened.

'I said, what's your name, slut? Veronica said in a low voice.

'I'm ... I'm Joanna, ... but ...' Joanna stammered, not wanting to be called a slut.

'Well Joanna the Slut. I'll be watching you, so be careful.' And with that, Veronica turned and sauntered off, laughing with her friends over what had happened. Joanna was puzzled and temporarily embarrassed but hurried off to class and back to her love of learning. It wasn't that she wasn't interested in sex, but it was something she was saving for later. She had had lost her virginity one night at a drive-in when her date cancelled and she drank too much and fucked a boy she hardly knew in the back of a van. It was highly unsatisfactory, being nasty, brutish and short, but at least the boy had pulled out of her before he came. At any rate it had been enough to put her off sex until after high school.

Her next encounter with Veronica was after the ten-mile run which all students had to complete. Veronica won the girls' race with ease, whereas Joanna came almost last. As a consequence, Joanna was last into the showers and lost track of time under the hot water, as she thought of the Jane Austen novel she was studying. Suddenly she realised that the buzz of girls' chatter had ceased and she was the only one in the shower area. She turned off the shower and stepped out into the main bathroom area, only to find Veronica, all dressed and sarcastic, waiting for her.

'Well look who's last! It's Joanna the Slut!' Veronica drawled. 'Too busy playing with yourself in the shower, eh? Can't leave your little cunt alone can you, slut?'

Joanna was suddenly aware of her nakedness, and tried to cover herself with her towel from this awful, threatening girl. But Veronica stepped forward and slapped her across the face, and grabbed her towel as she staggered backwards. Now she was naked with nothing to cover herself.

'Nice breasts, slut,' Veronica muttered. 'Bet you let all the boys chew on them, don't you? Nice little hairy cunt too. How many dirty cocks have been up you? Twenty? Thirty? I bet you've had fifty haven't you? Spreading your legs for everyone with a dirty cock. Well it's mine now slut! Your cunt is mine until I give it back to you.' Veronica pushed Joanna to the floor and thrust her hand between Joanna's legs. Joanna tried to push her away but Veronica was too strong. She held Joanna down with one hand on her shoulder and forced her way into Joanna's cunt with the other. She pushed two fingers into Joanna's dry slit, causing Joanna to cry out in pain.

'What's wrong slut? Do you only open up to cocks? I'll show you!' Veronica licked her fingers and forced them deeper inside Joanna's little cunt, and rubbed her clitoris with her thumb. She carried on like this for some time, grasping Joanna's delicate pussy while holding her down and insulting her in a filthy manner.

After some time, Veronica said, 'I bet you want to suck my cunt don't you, you slut?' Veronica stopped molesting Joanna's pussy and she pulled off her knickers, knelt over Joanna's head and lowered her cunt onto Joanna's mouth. 'Suck it, you little cunt! Lick my pussy! You know you want to!'

Joanna struggled but could not escape the girl or the cunt that was grinding itself in Joanna's face. Joanna could feel the girl's rough pussy hair and smell the strong pussy smell. She had never smelled anyone else's except her own before and it was overwhelming. Her face was soon covered with Veronica's juice as the stronger girl rocked and ground herself on her smaller, weaker opponent. Veronica kept up the insulting demeaning talk throughout and then began to pant and increase her pace, until suddenly she screamed, and Joanna's face was covered in warm liquid that smelled a lot like piss. 'Oh my god!' she thought. 'She's pissed all over me!'

Veronica fell forward onto her arms, panting and sighing with satisfaction. Joanna's head was still trapped, covered with cunt juice and piss. Eventually Veronica got up, and stood panty-less over Joanna. 'Now, aren't you a good little slut. I bet you enjoyed that didn't you?' And then she kicked Joanna in the ribs causing her to cry out in pain. 'Remember you're mine now bitch! Try to keep from fucking too many cocks from now on, or I'll bash you good and proper.' Then she spread her pussy lips, lewdly showing the pink within for Joanna to see and stepped off her and left the showers. Joanna was left alone and naked on the cold tiled floor, shocked at what had happened, and with a pain in her pussy and another in her ribs. She quickly showered again to wash off all the piss and pussy juice and arrived late for the next class, much to the teacher's surprise and disapproval.

Over the next few weeks, a pattern developed. Veronica would stop Joanna in the hall or playground and order her to be somewhere after school. After a few times, they would tend to meet at Veronica's house since Veronica's parents were usually out until late. If Joanna didn't turn up, Veronica would corner her the next day and punish her. The first time she didn't turn up, Veronica pushed her into a storeroom, and twisted her nipples until Joanna thought they would fall off. Then Veronica rammed her knee into Joanna's cunt causing her to collapse to the ground in crippling pain. The only other time, Veronica punched her so hard in the stomach that she couldn't breathe, and threatened to 'stick a beer bottle in your smelly cunt'. After that, Joanna didn't miss an appointment, no matter how awful it was.

At Veronica's house, Veronica would boss her around, torment her and use her sexually. At first, she would just order Joanna to strip naked in front of her and let Veronica finger her pussy. After the first time, Veronica started to use some lube she found in her parents' room, and her fingers slipped in easily even when Joanna was bone dry down there. She even managed to give Joanna an orgasm one day by thrusting her fingers in while twiddling with her clitoris. When Joanna came, shaking and quaking, Veronica felt even more smug, and called Joanna a 'dirty lesbian slut' for the first time. Joanna, naked and panting, was shocked that this violent bully who tormented her so much, could also cause her to experience something so powerful. It changed their relationship, but only slightly, as most of the time, Veronica still kept making her do unpleasant and often painful things. Besides her fingers, Veronica also fucked her pussy with other objects which often caused her more pain than pleasure: first with a toothbrush, then the handle of her hairbrush, then a tubular glass deodorant bottle, and then with various fruit: a banana, a big carrot, and then a long thick cucumber.

Joanna begged her not to put the cucumber in as it was as long and thick as her forearm, but Veronica laughed and coated the end of it with lube, before ramming it into Joanna's poor little cunt. Surprisingly over half of it fitted inside Joanna's cunt, and once it warmed up actually felt quite nice. Sensing this, Veronica started to rhythmically fuck Joanna's cunt, pulling the long object almost out of her then ramming it in, faster and faster while pinching Joanna's poor little clit hard until she made Joanna come again. It was so humiliating. She also made Joanna suck the cucumber like it was a giant penis, holding it against her own pussy so that it poked out like a giant cock, and forcing it in and out of Joanna's mouth and down her throat so far it made her gag. All the while she kept saying hurtful things like 'Suck my cock you little whore. Suck it like you suck your Daddy's big cock every night before he sticks it up your cunt. Suck it like you suck all the football team's dicks, one after the other, before they spray their come all over your big breasts, you little slut!' This 'cock-fucking' became a favourite of Veronica's and she bought larger and larger cucumbers just for this purpose.

Veronica was happiest when causing Joanna pain or discomfort. Veronica was obsessed with Joanna's lovely breasts and nipples, and was always pulling or slapping or biting them. Several times she tied Joanna's hands behind her back and put clothes-pegs on each of her nipples, causing Joanna to cry out with the intense pain. Another time she put a clothes peg on each of Joanna's labia, making her cry with the pain, while Veronica used the pegs to open and close her pussy lips and poke her fingers inside. After these occasions, Joanna's nipples and pussy were red and swollen for days, and drew further ridicule and punishment from Veronica the next time they met.