A deepthroat-challenge

“Alright here's the deal,” Beretta began, guiding the detective up and down his length as he laid out his proposal, “Over there on the counter is poor little Keiko's make-up bag, which she left behind when you so rudely kicked her out. There is a lip-stick in there. I want you to apply it and then I want you to deepthroat my cock. If you can get a lip-stick mark around the base of my cock, cleanly, without smudging any of the shaft, I will tell you where Wesson is...”

Nancy let the dick pop out of her mouth audibly and gave Beretta a taxing look while slowly, absently stroking his spit-covered member with her hand. She had deepthroated Patrick a couple of times in the past, though her husband was a bit shorter and less thick than Beretta. She was certain she could do it, though she might need a few tries. Wiping the saliva off her lips and chin she stood. “Deal!”

She felt Beretta's greedy eyes on her ass as she walked over to the counter and found the make-up-bag. Ignoring him, she quickly rummaged through it and soon pulled out the lip-stick. Frowning, she inspected it closer, uncapping it and checking the color.

“Wow...” she muttered. It was a bright, glaring red, the kind of color that just screamed “slut”. She did not remember the Asian girl's lips wearing this distinct color.

“Yeah,” Beretta spoke up behind her and she could hear the grin in his voice, “I asked her not to put it on. I thought it looked too cheap and whore-ish. Then again, it seems like just the color for you, Detective...”

Nancy turned her head to glare at the man and found him staring at her butt for another two seconds before he finally looked her in the eyes with a mischievous smirk on his lips. “Come on now, Detective Dicklicker,” he chuckled, his tone daring her to do something that could potentially stop him from following through on their agreement, “A nice, thick coating of lip-stick and then come here and gobble this dick!”

Opening her mouth she found she had nothing to say, so instead she bit her cheek and walked over to the full-length mirror on the room's wall. Without any support from a bra, she was very aware of how her big tits jiggled slightly with every step, making her feel a little self-conscious.

Standing in front of the mirror she was shocked by the naked woman looking back at her. Her hair was disheveled, her eyes slightly bloodshot and wet and saliva was smeared all over her chin with several shiny streaks splattered over her bare tits. To her dismay, she could also see Beretta in his seat behind her, a wide, arrogant grin on his face as he had just witnessed her shock at her own reflection.

The corners of her mouth tightened as the experienced detective admonished herself to concentrate and focus. Rolling out the lipstick she puckered her lips and leaned in to apply a coating.

“Fuck yeah!” Vincent whispered to himself as the detective bent forward in front of the mirror to perform her task. Inadvertently, this caused her to push out her firm, round butt and his eyes zeroed in on the sleek slit of the woman's pretty little pussy that just barely peeked out between her athletic thighs. Admiring the soft set of lips, Vincent made a promise to himself that he would absolutely destroy this whore's cunt!

“What in the fuck, McKenna?!” the voice inside Nancy's head berated her as for the first time in minutes she had the time to think, “What in the hell do you think you are doing?”

The truth was: she did not know. She knew Wesson needed to get caught and that she did not see a way to get the information in time but to follow through with Beretta's lewd demands. Nonetheless, she did not know if this way, acting like a complete slut, was the only way or if she just had not looked hard enough for alternatives.

That last thought was so uncomfortable that Nancy found herself rejecting and blocking it immediately, instead putting the final touches of lip-stick to her Cupid's bow before stepping back and smacking her lips, admiring her handiwork.

She had been right. It made her look like a whore... “The right look for you!” that nasty voice in the back of her head nagged, “You're going to let some lowlife scum fuck your mouth in a cheap motel... What does that sound like to you?!”

Almost wincing at the harsh thought, Nancy turned around to face Vincent again.

Somehow, while naked, cuffed and bruised, the young gangster still was a picture of arrogant self-confidence, lounging in the armchair with a nerve-wrecking, relaxed ease and watching her with the smuggest, complacent look on his face that Nancy had ever seen.

Seeing him brazenly take in the sight of her nakedness, Nancy felt the urge to cover up for a split-second, but her discipline saved her from showing this weakness. Instead, she defiantly lifted her chin and pushed her shoulders back. Beretta seemed unimpressed by this however and deliberately took time to admire the sleek mound of her pussy as the self-pleased smirk on his face infuriated her.

“Satisfied?!” she asked impatiently and gestured towards her painted mouth, her eyebrows lifted.

“Not yet...” Beretta chuckled, grabbing the base of his thick cock and obscenely waving it at her, “So get on your knees and take care of that!”

The nude detective gave him another glare. Tossing the lip-stick onto the bed, she walked over towards her captive and unceremoniously dropped to her knees.

Amused by how demonstratively unenthusiastic she acted, Beretta spread his thighs a little further to offer her more room and presenting his wrinkly nutsack to her even more. “I think I'd like you to lick my balls again first though, detective!” he grinned, easily holding her gaze as he stared down at her, “Come on! Earn that info!”

Utterly conflicted between disgust and arousal and with the excuse of her need for intel, Nancy **** herself to press on. Shuffling forward on her knees bit by bit to get herself into the perfect position, she grabbed the young man's cock around the base and began to stroke it slowly as she took a moment to inspect the thug's scrotum a little closer.

The bastard certainly had a pair on him. Nancy could not help but feel impressed by the two fleshy, plum-sized orbs that hung heavy beneath his shaft. They stretched the leathery, wrinkled skin of his sack down with their weight and looked full to the brim with cum. In a primal, dominant way the sight was even quite appealing.

It also did not hurt that the young man was certainly well-groomed and trimmed and the musky scent that filled Nancy's nostrils from this up close inadvertently caused her to salivate.

Knowing that if she waited any longer she was sure to draw a snide comment from Beretta, Nancy got to work. Opening her mouth and extending her tongue as far as she could, just like she had been told to do, she leaned in and broadly lapped along the root of his cock, making her way across the swarthy, crinkly skin in between his balls.

Vincent's reaction at the sensation was immediate. “Fuuuuck yeah!” he grunted blissfully at the delicate sensations, closing his eyes and throwing his head back in enjoyment, but only for a second before he looked back down to watch the show.

The detective really had a gorgeous pair of eyes. Big and dark, very expressive, her current position – looking up at him from between his thighs – really brought them off, making the strong-minded detective look like the most submissive slut. Even if her tongue weren't covering his ballsack with broad swipes, the color of her lipstick would have made her look like a whore.

Beretta grinned, congratulating himself to his decision. The thick coating of bright red really robbed a woman of all her classy eroticism, taking away all the sensuality and made her look like a cheap slut. The same reason he had told Keiko not to put it on earlier was why he now loved the detective wearing it. She looked like a cheap whore!

Gently placing his hands on her head, he began guiding Nancy's movements up and down, making her coat every square inch of his scrotum with another layer of thick saliva. To the detective's utter dismay, she found that if she brushed her lips against his skin even in the slightest it left a red smudge of slutty color. That did not bode well for the task ahead...

“Alright, pig!” Beretta said after the room was filled with silence but for the wet, slurping sounds of Nancy worshiping his testicles. His fingers curled into her hair, grabbing it assertively and he pulled her off of his cock, “Time to get to it now! And remember: no smudging! I want a clean offprint of those lips of yours around the base!”

Nancy stared at him, not even looking for a witty reply. Instead she focused on quickening her breathing, almost hyperventilating to fill up on her oxygen reserves to buy a little more time to work with. She then shifted her jaw from side to side to loosen the joints, knowing she would have to open wide for this to work.

“Okay, let's do this!” she pep-talked herself mentally, then took a deep breath. Tightening her grip around Beretta's base for a firm hold she gaped her mouth as wide open as she could. Then she closed her eyes tightly and dived down.

As Beretta's bellend hit the roof of her mouth, Nancy gagged immediately. She had hoped to get a good start by lurching down, instead, all she succeeded in was to make herself retch violently.

“GARRGH!” she groaned, out of reflex trying to pull back, but found to her shock that she couldn't as Beretta's tight grip on her hair instead pushed her down, pressing the head of his cock against the clenching entrance of her throat. In the distance she heard the thug laugh like a maniac as he thrust his cock upwards into her mouth even harder, grinding his hips to intentionally worsen her situation.

“NNNNGGLLLMMBSH!” Nancy screamed in fury. A furious gagging fit caused an explosion of spit, bursting out of her mouth and along the shaft and snot shot from both her nostrils, which only caused the cruel gangster to laugh even harder as he attempted to hit that specific trigger again. He viciously shunted his thick cock into her mouth while Nancy, retching and spluttering, did her best to keep her lips wide apart. Her desperation not to leave any red streaks on the man's shaft, only allowed him to facefuck her even harder.

“AAAARGH!” Nancy finally managed to push herself off and free herself by digging her fingers painfully into the flesh of Vincent's thighs, making the young gangster gasp in pain and let go. Her face was a mess when she staggered back and fell on her bare ass with a grunt, her chin wet with her own spit and teary streaks marking her cheeks.

“Y... you fucking bastard!” she coughed furiously after she had gasped for air for a few seconds as Vincent laughed in her face. Her red-shot eyes blazed with fury as she raised her finger at him. “You touch my head again and I break your fucking fingers!”

The cold threat was enough to stifle the thug's laughter. “Alright...” he shrugged and folded his cuffed hands behind his head while spreading his thighs even further in a silent invitation, “I won't help then... Go for it!”

Still eyeing him suspiciously, Nancy crawled back into position between his knees again. She felt her stomach quiver with nervousness as her eyes then dropped down to his cock, standing big and hard and menacing. She needed to get all this flesh into her throat to reach the base. It seemed like a ridiculous ask.

Beretta watched with amused intrigue as the durable, sexy cop swallowed hard, her eyes fixed on his cock like she was hypnotized, then took several quick, short breaths, opened her mouth in a wide oval and dived in. She went a little bit slower this time, letting his cock slide across her tongue on its way to the back of her throat. His folded hands clenched just a tiny bit when his bell-shaped head pushed against the end of her oral cavity, eliciting another gag that caused another dribble of slimy spit. He had to admire her discipline as she kept her luscious, soft lips wide so they would not touch his shaft. Her nostrils flared in preparation and her felt his tip press against her wet, narrow esophagus for several seconds before Nancy grabbed a hold of both his thighs. He felt her relax and push deeper.

For a second, nothing was happening. He felt his dick press against her tonsils with no budging. Then, a moment later, her throat opened. Vincent's eyes widened. “Holy Fuck!” he gasped, his whole body bucking at the sensation of the gorgeous Latina woman allowing his cock to slide several inches into her throat and he had to exert some discipline so he would not grab her head on instinct. He did not want to push his luck at this very moment.

“GLLRGH!” Nancy gagged as she managed to slide two inches into her throat. Fresh, sparkling tears welled from the corners of her clenched eyes and rolled down her cheeks. Pausing, she did her best to relax for a second, trying to get accustomed to the wide, cylindrical shape stretching and bulging out her neck before she slowly opened her eyes.

Seeing the detective's red-shot, glistening eyes open and stare at his groin was a sight that Beretta would savor for a long time. The view caused a short spurt of pre-cum to erupt from his cock and straight down into McKenna's belly. From the way her eyes widened for a second he knew that she had realized this, but she did her best not to show it.

After a few moments to compose herself, her gaze focused on the gangster's neatly trimmed pubic hair in front of her, Nancy assessed the situation. By her estimation there were another four inches to go, another four inches of thick, veiny man meat to swallow, before she could wrap her lips around the base. With her mouth stuffed like this she could not breathe at all, so her oxygen reserves would have to do until she had completed her task. Feeling a bead of sweat run down from her hairline and trickle down her temple, the stunning naked woman **** herself to continue.

“Nnnnngh!” Nancy's moan was muffled as she pushed ahead, sliding another two inches of man-meat down her throat, almost triggering her own gag reflex. Her tongue thrashed against the sensitive underside of Beretta's cock as she fought the urge, eliciting another grunt and another hot spurt of his seed splattered into her belly.

His action sealed the end of her fight against her own impulse and Nancy succumbed.

“GGRRRRLLGH!” she retched viciously as she lost her composure, her entire throat rolling in protest and inadvertently giving the scumbag an extremely sensual massage. Spit, snot and tears erupted from her orifices and before Nancy realized what she had been doing her lips sealed closed around the hot rod between her jaws.

“Oh yeah, you fucking dirty little bitch!” Beretta groaned in bliss at her misery, having the time of his life.

Within the throes of her fit, Nancy realized that she had lost and pulled back, the gangster's fat shaft slipping out of her throat and mouth as she dropped back heavily onto her haunches, gasping for air.

“ARRGH!” she gagged, having to fight not to throw up as she knelt there, her tits heaving as she pumped oxygen back into her body. She felt a mess, her face smeared in all kinds of bodily fluids, which really sank in as she recovered with her eyes closed again. As she panted and spluttered heavily she felt drops of saliva spray from her mouth. Her nose was running heavily and tears ran down her cheeks in streams. In addition her entire body was covered in a gleam of sweat. “Ohgod...” she winced miserably, “Ohfuck...” She felt like she had bitten off a lot more than she could chew here!

Vincent snickered. The young gangster flexed, causing his hard, saliva-slick cock to sway. There was a distinct red mark, almost circular, about two inches of the base. There was no question: the cop bitch had failed. Watching with satisfaction as she gasped and rasped on the ground in front of him, he leaned forward and grabbed his member around the base. With her eyes closed and her focus on herself she did not sense him coming, so she was taken by complete surprise and flinched back when he smacked his wet meat heavily against her features.

“What the...” she hissed, darting back and her eyes flying open before she was silenced by the sight of her lipstick smeared onto his thick, heavy prick. He could see on her face how her heart sank. It made him happy!

“Come on, pig!” he chuckled, shaking his cock in her face, “Clean me up and let's go again! Don't pussy out on me now!”

He saw her open her mouth to say something, but she closed it again. She looked ****. Defeated.

“I...” she began before pausing a second, “What do you want me to do?” She half-hoped he would allow her to use some wipes to clean it off, but her other half enjoyed the suspicion that he would demand that she would use her tongue. She felt ashamed realizing this.