A Bad Penny

(Author's note: Like the first part of this story this chapter contains significant male on male reluctant sex so if that is not your thing please do not read on.)

*

John sat paralysed as the clock in his office ticked past five o'clock. His girlfriend Julie, who also worked in the office, had already gone home being fortunate enough to finish up at three on a Friday. Normally John would be desperate to get out and start the weekend himself but this Friday he had been dreading it and was finding himself almost unwilling to get up from behind his desk to retrieve his coat when the door to the office banged open and in came Penny. Penny, the sexy office slut who had finally, after weeks of trying, seduced John only to drug him and set him up to be ass and mouth fucked not only by herself with a strap on but by three guys, all filmed and used to keep him firmly under her thumb (see my first ever story on Literotica 'A Bad Penny').

She closed the door behind her and stared at John rather like how a cruel cat does to a terrified mouse that it has cornered. She looked too good to be so fiendish, sultry in her smart business jacket and loose cream blouse and a tiny business skirt that barely hid the tops of her expensive stocking tops. She was a stunningly beautiful young woman, 27 with short dark brown hair and a terrific figure. But for John she was hell on heels and he literally cowered behind his desk as she confidently crossed the floor and stood beside him. She looked down at her shoes and gave an almost imperceptible nod. John dropped obediently to his hands and knees and began to reluctantly clean the scuffed top of her patent leather shoes with his tongue, just how she liked.

"Good boy John, I see that bitch of a girlfriend of yours had headed home, I take it you have everything organised as I instructed for tonight?"

John broke off his grovelling duties to look up at her and plead once again not to do this, even though he knew by now Penny had no mercy and especially where her rival Julie was concerned.

"Please Penny, don't make me do this! I'm begging you, anything but this, I know she doesn't treat you like she should but she's not a bad person, she doesn't deserve whatever you've got planned, I do, It's my fault, take it out on me, not her. Please!"

Penny kicked out her right foot and sent John sprawling on his ass on the floor below her.

"Pathetic! You really are pathetic. You will make sure you and that cunt are exactly where I told you to be at exactly when I told you to be there or else, well you know what I'll do, don't you bitch?"

Indeed he did, though whether it was the thought of the film of him servicing three extremely well hung black guys while dressed in women's underwear or whether it was the ever present threat that Penny would unleash them on him again he was not quite sure. He blinked and twitched nervously and to all intents and purposes this six foot man cowered and nodded his understanding and apology to this much slighter woman.

"Good, I knew there wouldn't be a problem bitch. You seem nervous about tonight, I don't know why all I'm going to do is show Julie a good time, that's all -- give her a Friday night to remember. Anyway, forget her for just now, right now you look like you need to relax, get rid of some of that tension from your body."

John just lay there perplexed as Penny reached into her pocket and plugged a memory stick into his computer.

"Right, get up wimp and get undressed."

Her last few weeks of domination really showed as her boss stripped naked almost without protest and at her strict direction stood up beside her despite the horrible prospect of one of the cleaners or another late afternoon worker bursting in on them. Still for all his protestations it was clear from the hardness of his cock that on some level he found the situation arousing so Penny knew he was little more than putty in her calculating hands to play with.

"Take that pathetic thing in your hand and start masturbating, you are going to get rid of some of that pent up frustration right here in your office."

She clicked the mouse to open a file from the memory and suddenly the screen was filled with the action from Penny's house all those weeks ago. John was onscreen with a big, black cock deep in his mouth as the other two guys were slapping their dicks all over his face.

"Nice action, eh? Now get wanking bitch!"

What a bizarre situation John was in and he did the only thing he could do -- obey the woman who held such power over him. To begin with he looked at Penny and imagined it was her hand gripped along his rigid penis, slowly jerking his foreskin back and forward as some wetness came onto his hand but she soon put a stop to that and ordered him to keep his eyes on the screen, to watch his own rape at the hands of her and her friends as he got himself off. It was sick and humiliating but he did it and felt very aroused as he pumped himself harder and faster with every second that passed. He had to bite his own lip to make sure he did not give himself away to anyone in the outside offices as he grunted and moaned his way towards orgasm. And when he came it was in a rush and he fired his sticky seed in thick bursts all across his desk and even one splattered onto his keyboard.

Penny stood over him regarding him like he was a piece of shit on her shoe. She leered at the traces of his seed now splattered across his desk and her beautiful lips curled once more into a contemptuous sneer.

"What a mess you've made bitch, it wouldn't be fair to ask the cleaners to clean that up would it? No. So you can fucking lick it all up, and you won't get your clothes back until you do, and we'll leave that film running on your computer too."

John was a weak willed man at heart, he had found that out the hard way over the past few weeks and Penny had broken his pride. Part of him wanted to disobey and strike her down but he didn't, he just bent over his desk and began to lick his own cum off it and then from his keyboard, his cheeks burned with shame. He tasted the sour taste of his cum and swallowed it down, knowing his only option was to obey this bitch to the letter. Penny laughed lightly as John degraded himself like this and as she headed for the door she turned around to give one last humiliation to him.

"That's it bitch lick up your mess. Here I want you wearing these tonight, no arguing you just remember to be there at eleven and wear those, that's not hard, even a dickhead like you could manage that!"

As she exited his office leaving him to scramble for his clothes and to get dressed he only managed to catch the pair of bright pink frilly knickers she had thrown at him.

*

Wearing those self-same panties John had taken Julie out as planned for a slap up meal at an expensive restaurant across town. Partly he had gone there to give her a treat, his guilt over whatever it was he was delivering her into (and given what Penny had arranged for him and her hatred for Julie he genuinely did not want to think what it could be) and partly because it was the perfect place to go to and then 'accidentally' get lost on their way back to arrive where Penny had instructed him to be.

He risked a glance across at his beautiful girlfriend, and god she was looking beautiful tonight, like an absolute Princess. John had been struck by how glamorous she looked all night, obviously wanting to look her best for their date at this restaurant. Her honey-coloured hair was being worn up and John thought it was magnificent the way it was neatly piled and layered to great effect. She was wearing a strapless scarlet coloured dress that seemed to be held up by her breasts and nothing else and it was short too, showing a nice amount of her tanned, athletic thighs. Her high heeled designer shoes, handbag and expensive diamond jewellery completed her look and John had received some pretty envious looks from guys in the restaurant when he entered with this gorgeous babe on his arm.

Julie sensed John looking at her and gave a cute smile, she had so enjoyed this evening it was unreal. She reached her hand down and clasped it over his on the gear stick and gave it a squeeze.

"It's been wonderful darling, thank you so much. You must really love me to take me some place like that."

The words broke John's heart and he had to fight off the notion to take a turn up ahead and avoid where Penny was expecting them. But Penny's voice rose up in his head and the threat of exposure came with it and, as much as he hated himself for doing it, he kept on forward at the crossroad and into the darkness that lay ahead of them.

*

Five minutes later.

"Are you sure this is the right way. I could have sworn we should have taken a left turn some way back!"

"Yes I'm sure, do you think I don't know my way around town?"

"Of course not darling but, well, I don't recognise this place and it looks kind of creepy and sleazy."

Julie was right there, reflected John, this area that Penny had set him as a destination was right in the wrong end of town. They were passing some pretty dirty looking bars and barricaded up shops and as they went along his smart BMW and their dinner attire was looking more and more out of place amongst the pimps, hookers and sluts that were peppered on the pavements in the dark night. Then his stomach lurched as he spotted the "NIGHTSPOT" , the bar Penny had told him to come to. Initially she had told him to get Julie to go inside it but then she had altered the plan somewhat and told him just to be in his car outside the place at eleven. Very deliberately he stopped accelerating.

"What's wrong? Why are we slowing down!"

"I don't know babe. Calm down, I'll pull in here and have a look and if it's bad I can call for assistance."

That hardly re-assured Julie who was looking around at the rough types outside the nearby bars nervously. John carefully came to a halt right at the small alleyway to the right of the run down bar. Looking around he got out of the car and popped the hood to peer into the engine. As he did he felt a hard shape pressed into his spine, it may or may not have been the tip of a gun. A harsh, rasping male voice whispered at him.

"Right on time Mister, tell your slut to come up here to help you, quickly!"

What happened next took less than a minute. John shakily asked Julie to come and help him and reluctantly she came forward. Just then a black transit van screeched to a halt beside them and both John and Julie were easily forced into the back of the van at gunpoint and they went flying into the night. John pretended to struggle and argue but a gun in his face quietened him while Julie fought for a moment until a sack was placed over her head and shoulders and she was bundled to the ground.

Some five miles away in a long since abandoned warehouse Penny was sat in a leather chair in an impossibly tight black leather cat suit that clung to her sexy body like a second skin. She was surrounded by three more heavies (there were four in the van with Julie and John) and she knew well fine that these guys would like nothing more to take her, abuse her and fuck her every way imaginable. But they didn't. Much as they would like to wreck her asshole with their big cocks they knew she was in league with The Boss and messing with her while initially would no doubt be enjoyable would in the long term be a terrible mistake. Unbeknownst to all but a select few Penny was an extremely powerful, important young woman and when she said jump goons like these said how high. She licked her lips and twirled a pen in her fingers restlessly, she could not wait until her bitch and his whore arrived.

Penny drummed her fingers impatiently, she was eager to start her evenings entertainment. Then she heard the throb of a waiting engine outside the warehouse roll up door and dismissed one of the men to admit the van and turned to their leader to remind him of what she wanted from this night. He had been told before but was a careless man and prone to forget if he got carried away with his 'work', especially around pretty females.

"Boris. Remember not to hurt the girl. She must not be marked, not with what I've got lined up for her after. Ok"

The bearded ex-Soviet tried to smile at Penny and grunted his ascent but he was hopeless at concealing his true feelings and Penny just knew he really wanted to have his way with not just Julie but herself as well. Penny picked up a leather, bondage style hood and pulled it onto her head and warned him a final time.

"Just remember, or it'll be you in the crate next!"

The hooded Penny lingered at the back of the group of men as the ones in the warehouse welcomed their colleagues in the van. The large roller shutter door crashed down and the van back doors were opened and the two prisoners were ushered out of the van and onto the cold on the bare concrete floor. Both Julie and John were scared (although both for very different reasons) and the sight of them all dressed up so smartly was a source of great amusement to Penny, though she stayed back and let her men carry out her instructions. Initially the men concentrated their efforts on John, he was dragged to a pole that stood by the wall to the office that Penny had briefed the men in and had his handcuffs moved so that they were looped over a high hook on the pole, meaning he had to stand on tip toes to keep his feet touching the ground. He put up minimal resistance and once he was hung up there Penny crossed over to him and with her body covering what she was doing from Julie's eyes she grabbed his balls through the cloth of his trousers and gave them a hard squeeze and whispered.

"Fancy you hanging around here bitch!"

The attention was now fully on the damsel in distress now as Julie knelt surrounded by the men and Boris addressed her in accented English.

"Listen to me American slut."

"Please what do you want? Please we've done nothi..."

"Shut Up! You speak only when I say you can! You dress like slut so we think you can act like one too! You want to be released with you and your man in one piece then you do exactly what I say, understand?"

Julie nodded frantically.

"Good. You start by stripping off. You show me and the boys what you got. You show us your slutty body."

Julie was mortified, although an extremely sexy young woman she was quite shy about showing off her body and the prospect of being naked before this group of kidnappers was abhorrent, plus she could not help but imagine what may happen once she was naked. But she was a smart girl and even as Boris moved menacingly towards John (she registered the hooded figure in black but barely) she knew that she had no real choice but to do what they wanted if they were both to get out of there in one piece.

"Ok! Ok! I'll do it, just don't hurt him. I'll do it!"

Reluctantly Julie started to peel off her elegant dress, she had hoped to top off her and John's special night with a special strip just for him and the thought of doing it for all these bastards to ogle her was almost too much to bear. With her dress went her modesty as she had no bra and nothing to cover her sweet, pert breasts, indeed as she stepped carefully from the dress all she had left on was a tiny pink thong. She stood there, half covering her naked boobs with her arms but not wanting to antagonise the men and felt the warm, hungry gaze of them and could not help but feel incredibly vulnerable. Boris stepped up to her and pointed to her thong.

"That too slut, you do not need clothing where you are going."

A comment that troubled her greatly as she stepped from the thong and revealed her freshly shaven pussy to her audience. Immediately Boris's rough hands were all over her, groping her breasts, fingering between her legs and grunting appreciatively. Penny looked on half enjoying her rivals discomfort, half hoping the pig remembered not to go too far. Julie recoiled to his touch but forced herself to stand there and endure this humiliating experience in the full expectation that things would only get worse from here on. But if she was expecting an immediate assault she was to be surprised, rather after he had controlled his groping hands Boris gave her some unexpected instructions.

"You, slut. Go over there and remove your boyfriends clothing -- all of it, leave him as naked as you are!"

Well it beat 'pull your ass cheeks apart and prepare to be royally fucked' for Julie so, surprised she did just that. Much to John's agitation. As she pulled off his tie and opened his shirt and pulled it back but not off to reveal his bare chest he tried to plead with her to stop but it was useless and he knew one of his dirty secrets was about to be cruelly exposed to his girlfriend. He looked toward Penny but all he got in return was a hard stare from her cold blue eyes in the hood. He made one last appeal to Julie but she knew he was being stupid and they would have to do what their captors demanded to escape this place in one piece but when she undid his belt and pulled his trousers to his ankles she saw immediately why he had complained so much, rather than his usual dark boxer shorts he was wearing those girly pink panties!

Julie fell back in surprise as he tried to explain and the cavernous warehouse echoed to much laughing from the kidnappers.

"It looks like we have two little sluts, not just one boys!" called Boris who had not really believed Penny when she had told him what the male was wearing under his trousers.

If nothing else kneeling there and seeing her boyfriend standing there wearing those pink, frilly knickers had briefly distracted Julie from their plight. She stared at the pink underwear incredulously as Boris took them and roughly pushed them straight into John's mouth.

"There that should keep you quiet while I explain to your whore what we are going to do to begin with. You see whore, we are not here to hurt you, oh no, we want you to enjoy yourselves. To that end, as your boyfriend likes to dress as a slut me and my men will treat him like one -- we will line up and fuck him in his ass. While this is happening you will play with yourself."

"What? No, you're crazy, this is crazy! John, why..."

Julie's frantic please were cut off by the back of Boris's hand (that brought a smile to Penny's face, she had wanted to do that herself in the office so many times). The big Russian bellowed at her.

"Enough, we start now, you either play or you watch as your man is ass fucked by us all. And by the way, it is your mouth that will be cleaning our cocks when we are finished with him!"

He did not hesitate further, instead he barged behind the hanging John and used his hands to part John's thighs. With his hands stretched up there was little he could have done to prevent it but he didn't even struggle with his legs, which Julie noticed half heatedly John bit down on the sweaty fabric of the pink knickers as the big bull of a man unzipped his trousers and shoved himself up and into his asshole. Of course, he had felt it before at the set up by Penny last time, but he had forgotten how humiliating and demeaning having another mans cock in his ass was to him and he also concentrated desperately on not being in any way aroused. He pleaded with his eyes to Julie to start doing what they had demanded and play with herself but she was understandably a little shell shocked and made no immediate move to finger her pussy. This could be a real hard time for John.

The big man was enjoying ass fucking his prisoner in front of his woman and really got into it, to the extent that John's body was quickly rocking back and forth in the air with each firm thrust of the Russian's hips. This unnatural movement seemed, at last to break Julie's doleful reverie and she finally moved her fingers down to her own neatly shaven pussy. She was not in the least aroused but became increasingly aware that she had to get there both to save John further torment and to save herself the indignity of licking any of these beasts dicks. It was hard for her though, to get aroused, what with being surrounded by a gang of hairy, leering brutes while her boyfriend was fucked by one of them. She closed her eyes and tried to imagine another time and place something that would sexually excite her and flicked and rubbed furiously at her pussy lips and clit. Strangely enough, in this most stark of moments the image that seemed to turn her on more than any other at this point was one of wishing that it was not her who was here like this but her arch nemesis from the office Penny and that the smug bitch was servicing all these horrible men with her slutty body. She was appalled at herself but put it down to the extreme circumstances she was stuck in, little knowing it was Penny herself who had arranged this.