Cheater Cheater 2.0

Story Info
What is the price for trying to cuckold the wrong guy?
9.5k words
4.45
29.6k
56
33
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
Dyspneiic
Dyspneiic
300 Followers

Okay, here we go—Cheater Cheater take two. This was my first ever story published on this forum. It caused such an uproar that the Mods took it down after 2 days for not following guidelines. Okay it was a little dark (okay a lot dark). It was shocking and brutal, and I was called a number of unflattering terms for even thinking it up. I was criticized for having a MC martial artist who didn't use martial arts and a father willing let his daughter be punished harshly (Ya'll never knew my dad—ask my sister). Whatever.

So, I basically gutted the original and rewrote it minus all the gore and horror. My goal with this piece is to still throw a spin on the whole 'cuck gets revenge' theme and I think I did well. The last version had folks threatening to call the civil rights down on my head for cruelty to women, awful acts of sadistic mayhem, yada yada. Fine...Paul keeps his dick this time. Not that it'll do him any good. Enough spoilers.

You have been warned. I hope you enjoy it. If you don't, remember four little words: It's just a story.

-Dys

Cheater Cheater

The front door opened, and a tall figure entered the darkened house. There was a click and light flooded the room, revealing the man seated in the easy chair off to the side. The intruder gasped in surprise as he noticed him freezing in his tracks.

"Hello Paul." The seated man said pleasantly. His eyes betrayed the ominous underlying anger and hate. "Please come in." He waved to a chair across the room from his, Paul gulped when he saw the gun pointing the way.

"M—Mikey..." He stammered. "Wha—what..."

"You two weren't expecting me to be home, I guess." Michael Trent stated dryly. "Don't worry buddy. Char will be along shortly." He explained as he waved the pistol at the chair once more.

Paul Anderson, Charlotte's immediate supervisor at the accounting firm, swallowed nervously as he walked over to the chair and sat.

"She has no idea either." Mike winked at him. "It will be our surprise." He grinned and rose fluidly to his feet. He strode across the room like a predator, stepping on the balls of his feet and maintaining a low center of gravity, as if it were second nature.

It was—after a lifetime of street fights, hardship, and questionable life choices. Michael Trent was not a guy you wanted to fuck with. He moved as if he were in total control of everything around him. He stood over the nervous man and held up several thick black zip ties. "Go ahead and put your hands behind the back of the chair for me."

A moment later Paul was secured tightly to the chair, his hands bound to the seat behind him and each of his ankles to the front legs. With a final touch Mike slapped a wide strip of silver duct tape across his mouth. "I don't want you blowing the surprise." He said as he placed the weapon on a shelf nearby. He switched the light back off and returned to his seat. They waited quietly in the darkness.

***

It was 8 years before, that Michael had met Charlotte Milano, at the annual charity event held for the Mission Hills Fire & Police Departments. It was a huge event held at Columbia College where he pursued a career in architectural engineering. Char arrived in tow with her father Luca Milano, a powerful businessman with suspected ties to the underside of little Italy.

The Milano's were pure Sicilian, transplanted directly from the Palermo region of the island. They carried themselves with panache and swagger, exuding wealth, and power wherever they went, and they dressed the part. Their pure Mediterranean bloodline also imparted a special trait upon the women—unsurpassed beauty. 20-year-old Charlotte Milano was blessed with it in abundance. Her dark olive skin and ebony hair, paired with almond brown eyes, thin nose, and exquisite high cheek bones; lent her an exotic radiance that turned heads everywhere. She stood 5'6" but enjoyed an additional lift from her 3-inch heels. She wore an elegant pale lavender gown that floated about her like thin gossamer, barely concealing her elegant figure. She carried herself with an air of mystery and aloofness.

Michael Trent was not the most imposing person, standing only 5' 8" and carrying his 190 pounds on a slender frame that he usually concealed in baggy slacks and loose-fitting button-down shirts. He kept his light brown hair a bit long and rarely combed it, giving him a haggard unkept look that earned him bemused quips from students and faculty alike. At 22 years of age, he was older than most of the student body. Yet he carried himself with a quiet unassuming manner that made him easy to ignore. He preferred it that way. Only a discerning eye would note the posture and subtle behaviors that suggested a sense of readiness and explosive potential.

Growing up on the streets of southern California forged a hardness to Michael. He found himself often hanging with the wrong crowd as well as the juvenile justice system. Gangs, foster homes, shelters, and detention were his teachers in the game of survival. Until he was placed with a charitable older black man named Old John. John ran a youth center and took in a lot of lost causes, sheltering them, teaching them, and giving them outlets for their pent-up frustrations. Michael found himself in the boxing ring early and was subjected to more beat downs than he could remember before he began taking the lessons to heart and allowing himself to be molded into something other than an angry young man with little regard for anything but his own welfare. He not only learned to control his body but also his mind. Eventually he took less and less punishment in the ring and began delivering some of his own.

More, he developed a sense of confidence and pride and at Old John's urging, completed his high school education and began taking free classes offered to disadvantaged youths. He still ran the streets but did so earning his keep by delivering pizzas and sandwiches until landing his first job with a construction company. The foreman was a friend of Old Johns and quickly took up Michael's education and upbringing. He also worked him to the bone every day, 12 hours a day accept Sundays. When he began showing an aptitude for reading blueprints and CADs, the foreman began grooming him for other things than manual labor. Eventually through corporate community outreach programs, Michael was awarded a partial scholarship and tuition aid to pursue a higher education. He enrolled in college part-time and continued to work his butt off, eventually climbing his way up to assistance foreman.

It should not have happened. Not by any stretch of imagination—could one conceive Michael and Charlotte becoming an item. It was still a mystery to him what she ever saw in him in the first place. Despite the odds they ended up together, talking about unimportant things, as they toured the event side by side, never once imagining a budding relationship. Later, when they parted ways, it was with a brief handshake and warm smiles. Michael walked away whistling softly to himself, amazed by her captivating beauty, but knowing that she was well and truly out of his league. He was also aware of the quiet scrutiny he received for the bodyguards and her old man.

It was by pure chance that they met again. Once more outside the tight knit Italian community. She was shopping with two other women, both as elegant and beautiful as their companion. He recognized her first (how could he forget) and greeted her pleasantly. She wore a classy floral print skirt that rode well above her knees, exposing two very shapely legs as well as a distracting amount of cleavage. At first, she seemed cool to his approach but then her face lit up when she recognized him. She immediately embraced him and kissed his cheek like an old friend. "Michael!" She purred in her honey sweet voice. "It is so nice to see you again." She excitedly introduced him to her friends who scrutinized him dubiously. In her heels she stood over him, and his unremarkable appearance and personality seemed hardly in keeping with their standards. Char ignored their misgivings and promptly invited him to lunch. When he hesitated, she latched onto his arm and would accept no excuses.

***

As he waited quietly in the dark room, he found himself wondering if she had ever really loved him. Was it even love that he had ever felt for her—once upon a time, before he discovered the hidden, painful truth? Whatever 'it' once was, was now gone, in its place a blackened pile of smoldering ashes. He hated her now. It was a raw emotion he rarely, if ever felt in his lifetime. An intense anger fueled by betrayal, shame, and utter humiliation. It was only through iron resolve and discipline that he was able to contain it with no outward expression. Thanks to those early lessons in the ring, he was able to compartmentalize and bring to bear an intense focus, just like he did when preparing for a match with an equally driven opponent.

The gun was a prop. It was real enough and loaded. But he never intended to use it—he did not need to. He was well enough equipped to cause damage without a weapon. It was only a means to compel obedience, without resorting to physical means. He rubbed his red knuckles as he recalled his earlier confrontation with two enforcers. He smiled darkly, remembering the satisfaction of sending them back to their boss, bloodied and broken.

How did it all come to this? He wondered. The cheating was bad enough. But their intentions for him as a part of their twisted charade, that was just over the top. A willing, even subservient cuckold? No way in hell! They thought they knew about power and control but had no idea with whom they were dealing. He was about to turn the tables on them in a wholly unexpected manner. Charlotte would be arriving home soon. Then she would discover a side to him she could never have conceived of, even raised as she was, a scion of the old mafioso families predicated for violence.

***

They had several dates before she took him to meet her family. Her father Luca greeted him with a warmth and acceptance that did not reflect in his eyes. He was gruff but well-mannered and dressed impeccably in a custom-tailored Italian suit. He was surrounded by a group of silent, tough looking fellows in oversized jackets. Michael was well aware of their purpose and function but pretended otherwise. He was so taken by the attentions of the lovely girl that he overlooked a great deal just to be with her.

He found himself at the Milano mansion often. Several times he would find himself left to the company of the old man and his men while she took off for God knows what. He did not mind her absences or the cool looks and attitudes he found regarding him. At first he felt as if he were intruding but eventually he was welcomed, if grudgingly. His lowly status as a street bred student did not reflect well on him or his attentions for the daughter of a powerful man.

Several weeks after they first met, Luca pulled him aside and they walked around an elegant inner courtyard garden, bursting with botanical wonders. The head of the family spoke to him with a thickly accented voice that seemed at once soft and dangerous. "Michael, I think you are a good man." He said quietly. "Perhaps even a man worthy of my daughter—that remains to be seen."

They walked quietly for several minutes. Michael chose to be patient and wait for the older man to continue. Perhaps the father approved because he sighed and continued in a different tone, almost conciliatory. "Ah but that girl ages me." He complained. "She has been spoiled. Perhaps it remains to be seen if she is worthy of you." With that he laughed. "I have checked up on you." He winked. "You are not who you seem to be Michael."

Mike looked confused at the statement. "I don't understand, sir."

Luca laughed again. "Oh yes you do!" He barked, chopping his hands through the air. "You were a street rat! A gangster." His laughter continued. "I like it. You are a warrior and you have done well for yourself. I respect that. Hopefully, you will do well for my daughter." He grew quiet. "I hope so." He stopped and turned to the younger man.

"I do not speak to you as a father who suggests dire outcomes if you fail her." He confided solemnly. "Charlotte is my only daughter, this is true. But she is her mother's child." His face seemed saddened and angry. "Her behavior, growing up has been..." He seemed to search for the right words. "In the old world it would have been...unacceptable." He continued. "Disgraceful."

Michael wisely chose again to remain silent. He had never seen Char's mother and she was never brought up in any conversation.

"Only here," Luca growled, waving his arm about "in California—can a woman behave as such and still be thought of respectfully." He turned and continued walking. "I pray she does not bring shame onto this family." He reached out and gripped Michael's arm, instantly noting the powerful muscles that lay hidden beneath his cloths. "Like her mother did."

No more was said as they returned to the house. Michael thought deeply about her father's words as they went out on another date. He wondered again about her mother but did not bring it up.

***

He heard the garage door open and the purr of the Jaguar's engine as it pulled in and parked. The garage door closed, and he noted the click of her heels as she approached the door to his immediate left. It swung open and, once again, then room was flooded with light. She stood in the doorway holding her Prada handbag in her left hand and her keys in the other. She wore a sexy strapless gown that hung precariously from the swell of her 34DD breasts, barely covering her ass. She wore a wide brimmed hat and bright red FMP heels. A shelved partition blocked her view of her lover as her eyes swept the room, but they alighted upon her husband and grew wide with shock. Her bag fell from her fingers, and she gasped in fear. Then she recovered and put on a practiced smile.

"Mi—Michael! You startled me!" She stepped nervously into the room, removing her hat. "Why are you sitting here alone in the dark baby? And what happened to your trip?"

He did not speak as he glared angrily back at her. He watched her façade crack as she looked around the room nervously.

"Michael? Is everything okay?"

He laughed suddenly and she gazed at him fearfully. "Is everything okay?" He repeated, the amusement in his voice did not reach his eyes. "Why don't you come in 'dear' and ask our guest?" He gestured with his hand, and she stepped forward automatically to see around the partition.

Her scream echoed through the empty halls of the big house.

***

After dating for nearly 4 months, she begged him to take her to his place. She had finished off a second bottle of wine at dinner, to his half glass and was feeling very amorous. He eagerly took her home and led her into the apartment where she spun about joyfully and wrapped her arms around him. With a deep enthusiastic kiss, she pressed her body against his and purred.

"Michael, I want you to take me to bed and make mad love to me!" She demanded drunkenly.

Mike did not have to be told twice. He led her to his bedroom with her stumbling awkwardly trying to remove her shoes. In moments he had her stripped down to her lace panties and stood before her in his own boxers. She embraced him and they kissed deeply, exploring each other's mouths with their tongues. Then she broke it off and smiled coyly at him as she lowered herself to her knees. With a swift tug she pulled his briefs to his ankles and grabbed his raging hardon with her free hand.

"Oh God Michael!" She crooned. "I can't believe you've been keeping this monster hidden away from me!" She stroked it eagerly and promptly impaled her mouth on it, taking his entire length expertly down her throat. Her oral skills by far exceeded all of his previous sexual experiences combined. He groaned with pleasure and surrendered himself to the incredible sensations of her probing tongue, sucking mouth and tight throat.

"Oh fuck!" He exclaimed. "I can't take much more..."

Her response was a moan and then she gripped him even tighter and redoubled her efforts to suck his dick off. In a rare loss of control, he grabbed her head and pushed his hips into her face, burying his cock as deep as he could in her throat. The sensation caused a spasm to rock his body, starting in his balls and flashing through every pleasure center in his brain. With a loud grunt he began thrusting harder as his cum began shooting down her throat one burst after another. He erupted five times into her mouth, shoving deeper until the sensation faded and he regained control over his shaky body. The entire time she accepted his abuse with passionate moans of her own. Pulling his spent cock from her mouth she smacked her lips and grinned up at him. Some of his cum had leaked from her lips and spilled down her chin. She sat back and wiped it with her finger, licking it off. "Yummy." She gloated.

He helped her to her feet and then lay her on the bed, settling beside her. As they caressed each other and kissed, he explored her incredible body with his hands and lips. Her breasts were simply perfect, each barely fitting in two hands, with stiff nipples that were marvelous to suck on. Her dark olive toned skinned trembled as he softly traced lazy circles across her belly with his tongue. He slowly wandered lower, and her lacquered nails began digging into his scalp, as he crossed over the threshold of her smoothly waxed pubic mound.

The scent of her arousal was intoxicating. She smelled of spices and nectar. He licked around her mound, avoiding her labia as he tasted the sweat of her inner thighs. When he finally parted her lips, he found her dripping with moisture. Her hips bucked erratically against his face as he explored and she screamed the instant he pressed his tongue into her clitoral hood, her nails gripping his skull like a vice. When he started licking her clit with firm circling probes, she squeezed her thighs tightly against his head and erupted into an orgasmic seizure that sent her over the top with pleasure. She screamed continuously as the waves of passion shook her to her core.

Seconds later she collapsed beneath him, and her legs fell apart. Her hands released his head as she threw them over her head and shuddered in his grip. "Oh God! Please no more baby!" She cried. "I can't take it!" Her chest heaved as she fought to catch her breath. He moved over her leg and crawled up to lay beside her as she recovered.

She turned to face him, and he kissed her tenderly with a warm smile. She beamed back at him.

"Oh my God! That was incredible!" She gasped. "You are so amazing!"

He rubbed her breast and pressed his hardening cock against her thigh, enjoying the sensation of her skin against him. She reached over and held his growing erection, squeezing and stroking him to full hardness. "Take me now and make me yours my love!" She crooned as she pulled him onto her, spreading her legs invitingly.

She was so wet that he was able to enter her tight vaginal channel smoothly. He tried to push into her gently, but she bucked her hips eagerly and promptly seated him completely inside her. Her mouth flew open, and a long moaning gasp escaped her lips, as if he had pushed the air from her chest with one thrust. He drew back, withdrawing most of his 7-inch length, before shoving himself back into her with more force. Her legs wrapped around his hips, and she grabbed him under his shoulders, as she threw her head back and grunted out in pleasure. He repeated the move even harder, and she cried out again.

He looked into her face, but her eyes were tightly closed. He began pumping into her quickly and her pelvis responded keeping perfect harmony with each thrust. He felt the head of his penis hitting the wall of her cervix with every penetration. Her vaginal walls clamped against his shaft, trying to hold him inside her as another orgasm suddenly claimed her. He felt her nails dig painfully across his back and sides. The pain spurred him onto to even greater efforts and he began slamming into her violently. Her cries became short grunting yelps as he fucked her with abandon. The bed shook beneath them and anyone in the adjacent apartment could feel the shocking thuds of their sexual frenzy.

Dyspneiic
Dyspneiic
300 Followers