Undercover Stripper 05

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A couple go undercover to investigate a crime syndicate.
7.8k words
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Part 5 of the 10 part series

Updated 08/22/2023
Created 08/20/2022
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Chapter 9 - Going all the Way

As Jessica came out from behind the backstage curtain Markov made his way directly towards her, clearly ready to demand she go upstairs to his office with him.

Across the room Tom saw what was happening and making a decision he quickly went ahead of them. Heading up the stairs he found the club boss's office door was open and he went inside, looking around for somewhere to hide.

"You've got some time before your next performance so; shall we go upstairs and discuss things?" The seedy gangster suggested leeringly to Jessica, his tone making it sound much more like an order rather than a simple request.

"Oh I... err... I umm... I suppose so."

Jess looked around for her husband as she started to panic, her heart thudding hard against her ribs now the moment she had been dreading had finally arrived.

"Good girl, you go on up and wait for me in my office. I just want a quick word with Daryl."

She swallowed hard. She was going to get fucked and she had two choices; either she ran or she committed herself to their plan.

"Remember what I said girl." From behind her Clarice, Daryl's wife, winked at her, "You do what you have to and get through it. I've seen your man; he'll be waiting for you."

Pushing open the door marked private, Jess hoped the other girl was right as she hesitantly made her way up the stairs.

"What are you doing here. He's right behind me." Jess hissed as she walked into the office a few seconds later and saw her husband standing in the middle of the room.

"Err... I... I..." Tom didn't know what to say.

"You really want to watch this?" She held up her hands and gave him an exasperated look, "You actually want to watch him fuck me?"

Her husband nodded dumbly and, without answering, just stared back at her. That was when they heard Gregor Markov wheezing as he stomped laboriously up the stairs.

"Get behind that door." Jessica pushed her husband towards a large cupboard, "And keep quiet."

He just about made it inside pulling the door shut behind him, leaving a small gap, before the seedy gangster appeared. Purely by accident the opening gave him the perfect view of the office and Tom realised he would be able to see and hear everything that went on.

Shutting his office door behind him the loathsome club manager sneered at Jessica in a way that made her skin crawl as she stood in front of his large desk. Biting her bottom lip and twisting strands of her long blonde hair in her fingers she waited nervously.

She knew she was aroused, a shift spent stripping and being fondled during her lap dances always turned her on and now, in this situation, the flush on her cheeks gave it away even more. Even if he was ugly and repugnant, he had a cock and that's exactly what she craved right at that moment.

"So... err... Mister Markov... what did you... want to talk about?"

Advancing towards her he smirked and, ignoring her question, pulled her against him and tried to kiss her lips but she managed to turn her face aside so his lips brushed her cheek. He attempted another kiss, this time his mouth found hers, his tongue swirling between her lips as he slobbered over her.

Then, satisfied that she would be compliant he let go of her and stepped back.

"I have a proposal for you baby, if you want to earn good money that is?"

He continued to leer at her, his beady hawk like eyes roaming over her slender barely covered body as he spoke.

"Oh, what is it? I'm always interested in earning more money." Jess replied cautiously, wanting to tempt him in to telling her more.

"Why don't you take off your top while we talk." It was a clear instruction to her.

Jessica could hardly object, he had seen her enough times in the club, so she reached behind her back unfastening her bra and peeling it away to reveal her perky modest breasts.

"That's much better." The gangster grinned and licked his lips.

She shrugged trying to suppress the mixed feelings of revulsion and lust that filled her.

Despite the fact that she had spent the last few hours dancing naked, being topless in front of the strip club boss in his office made her shiver apprehensively. She knew what was going to happen and, despite her deep-seated loathing of him, he had what she needed.

Markov leant back into the desk and pulled Jess against him, so she was sideways on to him, one arm around her waist as the other hand groped her tits, his thick fingers pinching and rolling her already hard nipples.

"Aaahhhh... fuck, what are you... uhhhh... doing!" She gasped, her head falling back and her long hair tumbling loosely across her shoulders.

"You like that don't you?" He smirked victoriously, "Roughly mauling first one soft mound then the other."

Jessica didn't resist, she knew she couldn't if she wanted to get anything out of him, instead she just squirmed against him, the sensations emanating from her abused breasts arousing her even more than she was already.

"So, you interested in earning some really good money then sweetheart?"

His fingers dug into the yielding flesh of her tits as he spoke.

"Maybe. I guess it depends on what's involved?" She managed to gasp out, her body trembling with unexpected excitement as he played with her two girls.

Grinning, he clearly thought he had her interest, "You entertain one of my special clients every now and again. That's all."

Jess's breathing quickened, partly from what his hands were doing and partly from the fact she was hoping to get him to talk.

"This a lucrative side-line for you?" Her free hand dropped to the front of his trousers, cupping his bulge, keeping him focused on her, rather than the conversation.

"For both of us darling."

"So, I have to sleep with them I assume," She sought further clarification even though she knew what he meant, "and become a prostitute, working for you?"

He laughed, his hand sliding down across her flat belly and between her legs to stroke her pussy through the tiny thong she had on.

Inside the store cupboard Tom's own dick was rock-hard now, watching the sleazy club manager grope his wife and proposition her to become one of his working-girls.

"Let's face it. You're not much more than that now sweetheart. You're a stripper, that's all." His tone was completely demeaning, "Now be a good girl and get on your knees."

Unresisting she knelt before him, feelings of utter mortification filling her as her fingers fumbled at his belt and then his zipper, unfastening his pants. Dragging them partway down she freed his prick into her hand, the solid thick 6" length already semi-erect.

"Good girl. Now show me how you suck cock." Curtly issuing his orders he smirked lustfully down at her.

Looking back up at him Jess flicked her tongue around his bulbous, mushroom shaped, cockhead, the musky scent of his manhood filling her nostrils. Drooling her saliva onto it her hand lightly pumped along the thick shaft as she felt it harden quickly.

"That's it darling. You know you might as well whore for me. You'll only end up doing it for Frank anyway."

'Frank again! But what's his surname?'

The thought flashed through her mind as her lips opened and stretched over the swollen dome of his erection.

"Gurkkkkkkkkkk... Urrrkkkkkkkkkkkk... Gurgggggggggggggg!" Jessica's mouth slid down his shaft taking a couple of inches of his rigid length into her throat.

Sucking on his dick she let her eyes flick towards the partially open cupboard door every so often. She couldn't see her husband but she knew he was watching her as her head bobbed steadily, working her mouth up and down Gregor Markov's hard meat.

"Fuck, you know how to suck cock bitch." Groaning he reached for her head, fingers twisting in her long blonde locks.

"Gurgggggggggggggggggg... Urrrgggggggggggggg!" She slurped greedily, her red lips tightening around his thick girth, her humiliation completed by his unwanted compliment.

Staring mesmerised from his hiding place Tom desperately wanted to free his erection and stroke it but, he knew if he did, the moment he touched it he was likely to shoot his load within seconds.

"Murnnnngggggggggggggggggggggggg!" Jessica gagged as Markov pulled her head against him, forcing almost all of his manhood into her mouth and stretching her jaws wide.

The odious club manager sneered, looking down at her struggling to breathe, her hands slapping his thighs in a frantic but ineffective gesture of protest. Holding her in place for a few moments he watched her face redden before he allowed her to pull away from him, coughing and spluttering, drool running down her chin.

"So baby, how do you feel about my little proposition. You'll earn at least £500 for an hour or two, maybe more if your dirty enough. These punters are real high flyers."

She looked up, saliva plastered around her mouth, her chest heaving as her breathing recovered.

"That sounds like pretty good money for just laying on my back." Jess answered quietly, "I could go for that."

Leering he pulled her upright and roughly pushed her back against the desk so her backside rested on the edge. His next words filling her with some alarm.

"Then forget about that new security guy, Tom. I can see you two are interested in each other but no one fucks my girlfriend unless they pay. Understand?" He stood over her, his hands back on her tits mauling them unforgivingly.

'Girlfriend. Tom had been right.'

She realised she was getting in deeper than she really wanted but she had no choice other than to go on.

"OK baby, if I'm with the boss why would I want the hired help?" She murmured seductively leaning back onto her arms.

Grinning at her, his hands dropped to her hips, hooking in the waistband of her thong and easing it down.

Jess didn't move, instead she just lifted her bottom letting him drag her panties down until gravity took over and they fell around her feet. Biting her bottom lip coyly she kept her eyes fixed on his as she took one foot out of her discarded knickers and then the other, before Gregor lifted her onto the desk's large, varnished top.

Perched there something within her seemed to snap and with a hard, determined expression on her face, she leaned back on her elbows and slowly opened her long, slender legs.

With a completely naked and compliant woman before him, a look of triumph spread across Markov's cruel face. Moving between Jessica's open thighs, he prepared to mount her, raising and parting her legs even wider, giving him full, unobstructed access to her cunt and providing him with a clear view of her waiting, glistening sex.

"Does the big boss know about your little side line?" She asked him, batting her eyelashes, as she waited for him to enter her.

Markov laughed, "Frank Harwood, you must be joking. That tosser hasn't got a fucking clue what I'm up to, he's too busy running his own stable."

'Frank Harwood!'

Jess gave a silent whoop of success as she found out the name of the unknown gang boss.

From his hiding place Tom watched, his own erection throbbing painfully, as the club manager took his thick shaft in his right hand and began to rub the crown up and down his wife's slit until he had located the entrance to Jess's vagina.

A moment later his cockhead was lodged firmly between her inner lips.

The seedy older man paused, his erect cock poised, ready to slide it all the way into Jessica's wet pussy. She gasped and felt her chest tighten frighteningly, her heart thumping furiously at what was about to happen.

She was turned on and she needed to be fucked, the fact it wasn't her husband's manhood that was about to enter her was almost immaterial. The shame and humiliation that she felt only complimented the arousal that filled her.

"Tell me what you want?" Markov demanded, teasing her sex crack with the head of his dick.

An unbearable agony of anticipation flowed over her. She could feel her husband's eyes boring into her as she turned to stare straight at the cupboard.

"Put it in me." Jessica whispered hoarsely.

"Not good enough. I said tell me what you want!" The gangster snarled angrily, "Do as you're fucking told, whore."

Her deep blue eyes turned back towards him and she fixed him with her penetrating gaze and Markov's body tensed in readiness.

"Fuck me... I want you to fuck me!" Her voice was husky with lust as she told him what he wanted to hear.

Grinning he slowly but firmly, began to force his hard meaty pole into Jessica's moist, open crack.

"Oh... my... God!" Her head fell back, blonde hair cascading past her shoulder blades onto the desk as she gasped with unwanted pleasure.

The crown of Gregor Markov's thick, smooth prick was driven past her inner lips and plunged a short way into her tight wet passage.

"Aaahhh... fuck.... yesssssssssssss!" Jess moaned, partly in pleasure, as her quim tried to adjust to his thick girth.

Tom swallowed hard, his eyes fixed on the mating couple, his chest so tight he could hardly breathe. It was actually happening. Right there, right then, another man's erect penis was actually inside his beautiful, sexy wife's vagina.

"Oh God! Oh, my sweet Jesus!" Jessica's thighs pushed wider.

Markov had pulled himself back until just his mushroom shaped head was still between her lips, then thrusting forwards again, he plunged deeper, burying two thirds of his solid length inside her.

"Oh... my... fucking... God!" Jess cried aloud as a wave of overwhelming and completely unexpected pleasure surged through her newly penetrated form.

Her deep blue eyes opened wider, her body going rigid while her hands reached out towards him, as if trying to push him away, but not quite able or willing to do so.

"Oh god... please! Oh god fuck... fuck me... please fuck me!" She begged, her raised legs trembling, her feet waving in mid-air.

Smiling the overweight club manager drew his shaft back for a third time, then thrust himself slowly but inexorably all the way into her defenceless pussy once again. This time not stopping until his full length was completely sheathed inside her.

"Please." Jess whimpered giving herself to the pleasure he was creating in her, "Fuck me, just fuck me!"

"Shhhh baby, all in good time!" He smirked triumphantly, "You'll get it all sweetheart."

Tom could see a momentary look of disappointment on his wife's face as Gregor Markov pulled back one final time, leaving her empty before driving himself powerfully forward again. The force of his thrusting hips lifted her legs even higher and wider until his coarse pubic hair ground roughly against her shaven mound and he was finally there, his cock fully embedded in her wet sex.

"Christ! Oh Jesus Christ! Yessssssssssssssssssssss!" Jess wailed as Markov's hips smacked hard against the underside of her buttocks, driving her bodily up the desk, sending a pile of papers onto the floor above her head.

For a moment, the scene froze in front of him and Tom stared helplessly at the couple on the desk; the most beautiful woman in the world lying there, her newly violated frame impaled on another man's thick, pulsing shaft.

She was panting breathlessly as her pussy tried to adjust to the unfamiliar phallus that was invading her body, her eyes open wide in fear and anticipation.

Then he began to fuck her!

Slowly at first, so slowly Jessica could look down and see her lips stretched tightly around his wet, glistening manhood as he started to move in and out of her cunt.

Beginning with short strokes, his speed and power built slowly but relentlessly, his cock growing wetter; shining with her juices as his thrusts grew longer and deeper.

Helpless beneath him, Jess began moaning in time with his strokes, her long legs flailing wide, then curling around his back as if to hold him closer to her. She hadn't anticipated this happening; she had thought it would be over in seconds but the man screwing her was obviously an expert when it came to pleasuring a woman.

"Shit... Oh shit, yes, yes, oh yes oh fuckkkkkkkkkkkk!"

Her hands, which had at first appeared to be pushing him away now grabbed at his upper arms, her fingernails digging into his biceps as he fucked her harder and faster.

His tempo increased and her moans grew louder too until, to her watching husband's amazement, she came.

Her head jerked violently forwards while her back arched and her hips bucked as her whole body erupted in an orgasm so powerful and so completely unexpected that it frightened her.

"Aaaaaaaahhhh... fuck... I'm... cummmmmiiinnngggggggggggggggg!"

Tom couldn't believe his eyes or ears! In all their years of lovemaking, his wife had never responded this quickly before or had an orgasm as intense. And what made it worse for him was that the arrogant bastard had barely started fucking her!

"Good girl!" The club boss leered, as she spasmed beneath him, "You're gonna make me a lot of money."

"Please...please... just fuck meeeeeeeeeeeeeee." Her hands slapped at his forearms as she whimpered submissively.

Picking up his pace again his forceful strokes continued relentlessly and a dozen deep thrusts later, another wave of ecstasy rippled visibly through her body.

Even if he wanted to intervene, Tom was incapable of doing anything other than watch spellbound as his lovely wife was fucked hard and expertly before his helpless eyes.

As soon as the second wave of her orgasmic trembling began to fade, Markov resumed his slow deep thrusting. His cock glistening with the juices that now flowed freely and messily from Jessica's pussy. Pulling back until just the head of his shaft was at her entrance, he plunged powerfully into her again, and then again, continuing to fuck her brutally.

Jess was totally lost now and her response was immediate, deeper groans filled the room in time with each thrust as her arousal began to build rapidly again. The speed of his strokes increasing and a new sound began to make itself heard; that of two highly lubricated bodies colliding every time his rock-hard manhood bottomed out inside of her soaking fuck hole.

Slap!

"Oh shit... oh fuck."

Slap!

"Don't stop..."

Slap!

"Oh god... don't fucking..."

Slap!

"Oh... my... GoDDDDDDDDDDDDDDDDD!" Taking every inch of his prick in her stretched slit she squealed helplessly.

Climaxing yet again, Jessica's legs wrapped themselves around his waist, then rose high up his back before falling helplessly and grotesquely apart as the force of his thrusts drove her bodily across the desk's slippery surface.

Grabbing wildly at his arms, then at his shoulders, her deep blue eyes locked fully on her lover's as she lost control of her body and came closer and closer to a third and even more intense peak.

From the storage cupboard Tom stared at his wife's violated sex and the thick shaft that was plunging into it over and over again. A rim of white foam had formed around its base as her flowing juices were churned into a thick, strong smelling orgasmic cream.

Small, high-pitched yelps of pleasure escaped Jessica's lips each time his cock bottomed out in her, plumbing her deepest recesses and battering her cervix mercilessly until finally, she reached the massive, mind-numbing, all-consuming orgasm that had been building within her.

"Ooooooohhhhhhhh my fucking God... I'm gonna.... Fuckkkkk!" Her scream of pleasure reverberated around his office.

"That's it whore, cum for me!" Markov grunted, his voice low and harsh, his thrusts totally unremitting and completely merciless now.

"Ooooooowwwww.... Jeeesssussss... I'm cuuuummmiiinnnggggggggg!"

The sound that broke from her mouth as the first wave of her most powerful orgasm broke over her, was virtually unintelligible and incoherent. And when the next, even greater blast struck, depriving her of the power of speech entirely, there was no doubt in Tom's mind that his sweet wife was having the climax of her life.