A Bad Penny Ch. 01

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Beauty gives her boss a real seeing-to.
3.9k words
3.95
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Part 1 of the 2 part series

Updated 10/17/2022
Created 08/20/2004
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TheDarkCloud
TheDarkCloud
4,487 Followers

John was pretty content with his life, he was 29 and office manager of a busy sales office. He was tall, dark and relatively handsome with a pretty easy going manner. All the people he worked with were hard working and got on really well and there was a good work atmosphere. In fact he got on really well with one of the ladies in the office. He and Julie were having a hot and sexy fling. Which was OK as neither was married or seeing anyone else, but they tended to keep it a secret as they worried what the gossips in the office would say and his bosses frowned on that sort of thing.

Things changed when Penny arrived in the office one fateful Monday morning. Penny had worked in one of the other departments and everyone had heard stories about her and were surprised when she showed up at John's desk and announced she had been transferred to the sales office. John was put out and checked with his boss who shiftily answered that it was correct and he would just have to deal with it. It wasn't a problem was it? There wasn't much John could do other than try to make the best of it.

The gossip that surrounded Penny was on the whole not that pleasant. She was a stunningly beautiful young woman, 27 with short dark brown hair and a terrific figure. It was how she flaunted that figure that got most of the men and women talking (in very different terms!). She tended to wear very tight tops and blouses, designed to display her ample cleavage to maximum effect, she also had a collection of the tiniest of skirts that more resembled belts than skirts. But it wasn't just her clothing, her attitude was completely selfish and she didn't make any female friends and the only men she gave time to were those above her that she could gain from being nice to. To those below her or on the same level she could barely disguise her disdain for and rarely gave them the time of day. She was very good at her work and was obviously very ambitious and had made a rapid ascension through the company but John couldn't understand how she had made it into the sales team.

It was a bigger shock to him when he learned her salary, which was not far below his own and was much more than the other girls doing her level of work in the sales office were on. Foolishly he let it slip to Julie as they lay together one night and she, not surprisingly, went on a verbal tirade.

"That Slut! I bet she slept her way to that."

Julie hated Penny with a passion from the first. She snubbed her and made no attempt to welcome her to the office– she saw her as a threat and a loner and someone who worked to her own agenda, but no-one could find out what that agenda was. The others in the office were hardly friendlier to Penny but it didn't seem to bother her and she did her work fine. It bothered John though why she had been put into his dept. and it bothered him even more when his boss instructed him to work with Penny on the implementation of a new computer system in the office. Julie was pissed off about that and let John know all about it, which annoyed John because there was little he could do about it.

Working so close with Penny John could hardly fail to realise how sexy and gorgeous she actually was. Not a trace of fat on her body, and how exquisitely she was always dressed– she obviously had plenty of money. She wasn't married though, John knew that much and as meeting grew into meeting John became inexorably attracted to Penny.

It was subtle stuff at first, licking of lip, leaving a hand lingering a second longer than it should, stuff like that. Penny had obviously done this before and within two weeks John was putty in her hands. Julie didn't realise but was not happy at the time they were spending together.

Then one morning Penny made the move.

"John, aah?"

"Yes, Penny?"

"I've seen the way you look at me, would you like to do more than just look, " she, very brazenly rubbed her breasts as she said this, sure he could not resist. And he couldn't, almost falling over himself to agree to invent a reason for him to go out that evening and visit Penny at her home.

John told Julie that he was going down to the pub with his mates that night and arrived at the address Penny had given him a full fifteen minutes early. Nervously, like a schoolboy, he approached the front door and rang the bell. It was large house with a big garden in the affluent area of town. He waited a full minute and was contemplating ringing it again when the black door swung inwards.

There stood Penny, wearing a cream dressing gown made of expensive silk. She smiled coquettishly at John and beckoned him in wordlessly by crooking her index finger and motioning him inside. He followed like a little puppy dog.

Once inside he took a turn into a large and lavishly decorated lounge and took a seat on a white leather sofa, Penny standing before him. Slinkily, she undid the belt of her gown and shrugged it off to reveal her trim figure covered only by a matching set of lacy bra and panties in orange. This showed up beautifully against her glowing, tanned skin. John was enraptured by the sight and positively drooled at the thought of fucking this woman.

"Like what you see John?" she purred.

"Oh yes, absolutely."

She turned her back and gave him a full view from behind and wiggled her way to a drinks table on the far side of the room. She poured two drinks and brought them back, giving John his alongside a kiss to his cheek. John was so intoxicated by her beauty, her scent, her voice that he drank the wine greedily. Penny smiled and shrugged her gown back on, John lay back and felt the rush to his head from the drink.

Suddenly he felt disorientated, his head spinning, the room spinning as well, three Penny's before him, laughing as he struggled on the sofa then fell to his side, his eyelids too heavy to keep up and then darkness.

He awoke ten minute later (though he didn't know that), his eyes springing open and being dazzled by light. Slowly he moved his head to take in his surroundings. He quickly realised that he couldn't move his limbs and soon felt the ropes binding him. He lay flat on a large double bed, he had been striped naked his clothes lying in a pile by the bedroom door. His ankles were bound by rope tightly knotted to them as were his wrists behind his back. Stopping him making any noise above grunts was a rubber ball gag shoved well into his mouth then attached by straps around his head. He had a black leather collar around his neck and from the metal ring at the front a leather leash connected to the bed frame preventing him moving other than rolling side to side.

He lay there helpless for a few minutes and Penny showed up at the door. She had changed considerably since he had seen her last, gone were the winsome smile and soft lingerie to be replaced by a hard sneer and an outfit all in black leather of tight basque, shorts and knee high boots. She looked every inch a Dominatrix from a porn magazine.

"Enjoy your sleep Bitch?" questioned Penny and John realised he had been drugged.

Penny stalked around the bed slowly, all the while sneering at John. She really looked nasty and totally changed from the woman he has fallen for in the office.

"Do you like giving me orders John? Do you like making me work?" her voice held a barely disguised hatred.

John could not answer, so Penny continued, "Well I've got something for you, something I don't think you'll like "with that Penny bent down and reached to the foot of the bed and stepped into something, John couldn't quite see what. His eyes opened in horror as she drew the item up her legs and it came within eyeshot – it was a long, thick, veined, black, plastic, strap-on dildo. Penny very deliberately tightened the harness around her crotch and goaded John with it by wiggling it against his distraught face.

She moved behind him and attached a spreader bar to one of his ankles then quickly undid the bonds around his legs and attached the other side so his legs were stretched nicely apart, a little lever in the bar that would allow her to further open the gap or reduce it at her will.

Penny moved around to John's upturned face again and spoke with a fake sweetness "Well lover you came here to fuck me but it looks like that's not going to happen, doesn't it. But you will get fucked. Ever been fucked in the ass before?"

John shook his head violently, a desperate action. Penny smiled "Don't fret too much Bitch, tell you what I'll even let you get the tip of my dildo nice and wet so it won't hurt quite as much." She eased off the ball gag and before he could say anything thrust the head of the plastic cock into John's mouth...

With little other option John tried his best to lubricate the thing in his mouth, terrified at the thought of it invading into him elsewhere. Penny held the back of his head to ensure he couldn't pull his mouth away and started to rock her hips backwards and forwards fucking his mouth and obviously getting very turned on while doing it.

"Yeah Bitch take it all, suck it like the slut you are!" and with that she thrust the dildo right down his throat and he unwillingly deep-throated the phallic object in his mouth. Having never done this before he quickly gagged but Penny allowed him no respite and held his head firmly in place. The unfortunate thing was that he was not wetting the tip very much and when she withdrew the cock from his mouth there were only a couple of saliva trails to lubricate it. Then Penny rammed the ball gag back into his mouth and moved to his ass.

She stopped saying she had forgotten something and knelt by the side of the bed. She came up holding two metal crocodile clips which she managed to attached to John's nipples, they bit into his flesh hard and he screamed into his gag, Penny smiled. She then produced a shoelace which she had tied a slipknot into and looped it around John's balls, pulling it nice and tight and leaving the end loose between his legs on the bed. Of course, by this time what wetness had existed on the plastic cock had all but gone, just as Penny had planned.

As Penny manoeuvred herself between John's legs she whispered forward into his ear "This is going to hurt you an awful lot more than me Bitch!" and with that she thrust forward brutally and right into his arsehole.

Penny thrust forward with all her strength, driving the dildo right into John's dry ass. He screamed in pain into his gag and this drove Penny on further as she got at least eight inches inside him. Then she started to develop a rhythm and began pounding into him relentlessly. She reached forward and in her left hand took as firm grip of John's black hair and pulled back so his body reared up and she levered her fake cock further into him, each millimetre causing further pain to him. With her right hand she reached down and took up the lace end and pulled with all her might, tightening the knot around John's aching balls to extreme degrees.

Penny showed no mercy to her victim fucking him and torturing him like that for nearly thirty minutes, obviously orgasming herself multiple times at the havoc she was wreaking on her boss.

When finally she pulled the strap-on from John's wrecked asshole he was a broken man. He was weeping at the pain he was in and his mind had lost focus (the remnant of the drug fogging it further). When Penny came round before him, her fake cock bobbing in front of her and removed the gag from his mouth he could say nothing. And when Penny ordered him to lick the messy dildo clean he obeyed immediately, his tongue moving over every groove on the object cleaning the mess left from his own backside.

Penny produced a video camera and captured John sucking this black, plastic cock around her waist, being careful that her features didn't show. When John had licked the dick clean and lay on his chest with a glazed look on his face, Penny paused the tape and spoke to him.

"Well done Bitch. You took that fucking like the Bitch you are and I think you'll be useful to me in the future, but I need to make sure. Come on, look into camera and tell me you like sucking this (waving the strap on before his eyes), tell me how much you enjoy sucking big cocks!"

John was a beaten man and he would do anything to escape this hell he had found himself in and he looked up and admitted into the camera that he "Liked to suck big dicks."

Penny smiled and paused the tape again as she called out "Boys! He's ready."

John's eyes moved around the room and he was stunned to see three well built, muscular, young men come into the bedroom. All were completely naked and had huge cocks – all over 9 inches. Penny smiled evilly again at John's consternation and spoke to him again.

"So you like to suck big cocks do you Bitch? Well in that case you'll really enjoy what I've got arranged for you now. This is Clyde, this is Eric and this is Manny and they just love gang-fucking a filthy man-bitch like you."

Penny stood back and prepared to film what was about to happen, the unnatural appendage still strapped around her. John lay desperately trying to escape his bonds, panic suddenly clearing his mind as he clearly realised what was about to happen. He pleaded with the men first and when they just smiled at him and continued to advance he pleaded with Penny, she just laughed and told him to 'enjoy' it.

The men actually undid all his bonds and once free John tried to escape but the three of them were each stronger than he and they easily forced him down onto the bed, their hands all over his body. They played roughly with the clips on his nipples and the lace around his balls, their gigantic penis's becoming more aroused with every second that passed.

The one called Clyde broke off and positioned himself in front of John and tauntingly bounced his firm dick off John's face a few times, before warning him of the severe consequences if he were to feel John use any of his teeth. He then shoved his big cock into John's waiting mouth, filling it with man-meat until Clyde's bristling pubic hair roamed over John's nostrils, the massive member buried deep in John's throat.

"Come on Bitch suck it off, I'm gonna paint your face white with my cum!"

From behind he heard one of the other guys laughing about his ass and felt a sharp sting as a hand descended onto his ass and spanked him.

"Yeah baby, shake that ass Bitch" was shouted to much laughter.

Penny zoomed in to fully capture the young man's balls bouncing off John's chin and the wide-eyed look on his face as this young stud mouth fucked him. John felt his arse cheeks being pulled apart and the two men behind him discuss the work the strap-on had done earlier. He then felt one of them slide the helmet of his dick inside his arsehole and slowly thrust up and inside him.

Penny moved back to capture the scene in it's full glory as her boss was being used like a spit roast between these two big, young guys while a third (with the biggest erection of the three awaited his turn).

John could hardly believe what was being done to him and he struggled as the two men invading him got rougher and rougher with their thrusts, one pushing him backwards while the other pushed forwards. The man in his mouth tensed up and John knew what was about to happen but was powerless to prevent it. He slipped his cock out of John's gasping mouth and for a split second the large dick pulsed before John's horrified eyes before pumping a wad of thick, creamy cum over his face. He pumped it five, six times and the cum got all over John's face, in his eyes, up his nose and in his hair and mouth. Penny zoomed in to capture John's cum-covered face.

Without allowing John time to get this breath back Manny now stepped forward and guided his 13 inch monster cock into John's coughing mouth, straight away deep throating him.

"Heh, heh Bitch you'll take it all" he sneered.

John was really struggling to breathe now and with an evil grin Manny reached down and pinched John's nose to make his plight even worse, especially as every half second or so his backside was being fucked forward with considerable force.

As John gasped and gagged on the thick cock that was raping his mouth and throat he became aware that Eric, who was in his ass was starting to jerk rapidly and sickeningly he realised that he was about to cum in his ass. He prayed that he would pull out but no luck and he felt the warm liquid shoot out and into his bum. Eric laughed and moved to the front again and as Manny continued his oral assault Eric mockingly wiped his spent dick clean with John's dark hair.

"You like that Bitch?" asked Eric, "You like having my thick cock up your ass?" Manny manipulated his long hard penis in John's mouth to nod it up nod down. That movement seemed to set Manny off and within seconds he exploded, sending a literal torrent of cum down John's throat, the salty taste raising the gorge in his throat.

With all three men having ejaculated Penny stopped filming. She kissed and congratulated them and then moved over to speak to John who was laying, in a daze on cum splattered bedcovers.

"Well John you came here for sex and you certainly got it didn't you? You now have two choices. You can either be taken by my three friends again, and this time all three get a chance to ride your arse, or you can put these on (she threw him a small pile of clothing), kneel in the centre of the floor and beg them to cum all over your face. Your choice. You have one minute to decide."

John looked at the garments; they were a pair of pink lacy knickers, pink bra and pink suspenders. John started to cry at the thought of having his poor, sore backside abused any more but........ "OK, I'll do it" he finally admitted.

Penny smiled and said "Well hurry up Bitch we haven't got all night."

So John pulled on the sexy woman's clothing and got down on his knees and looked pleadingly at the three men and begged them to spunk over his face, which they proceeded to do, three big, hard dicks bouncing over his face until one by one the came again coating his face a creamy white. Penny filmed this whole scene from one side.

Once finished Penny asked the men to leave the room but to be ready to come back if she needed them. She wouldn't though, John was a broken man.

"From now on John you will be my Bitch. You will do what I say and when I say it. Understand? (a faint nod in response). Good. I'll tell you now if you fail to comply in any way at all I will make sure that everyone at the office, your family and friends all get a nice, edited copy of this video. I'm sure they'll be surprised at you."

"What is it you want?"

"You'll find out soon enough. I have a lot of plans.First though I want to teach that stuck slut of a girlfriend of yours a lesson that she won't forget. And you're going to help me."

From that point on John was totally under Penny's control, it wasn't just the threat of showing the tape either (although John couldn't imagine his friends and colleagues reactions upon seeing it), it was something more than that. That day Penny had broken his spirit and weakened him as a person and in his eyes she had demonstrated her terrible power and in equal measures he feared and loathed her but he could not stand up to her or disobey her.

Of course Julie noticed the difference in her boyfriend and boss straight away but was at a loss to explain it. She thought perhaps that Penny was screwing one of John's superiors and he was exerting pressure on John. But he wouldn't say and avoided the subject like the plague. He did treat Penny differently than before in public, not massively so but he was more polite and always made sure she got included, even when everyone else didn't want her.

"Do you fancy her or something?" accused Julie on one evening.

In private things were much different, when Penny was alone with John she bossed him cruelly making him do embarrassing and humiliating things. More worrying than that Penny was starting to obsess on Julie, how she hated her and her plans to 'get' her. Anytime John tried to talk to her about it and try to calm her down he ended up being threatened and Penny made no secret that she had very powerful "friends "much more than just Eric, Clyde and Manny", which always shut John up quickly.

TheDarkCloud
TheDarkCloud
4,487 Followers
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