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
"Another, please," he said to the bartender, handing him the empty beer bottle he had just finished. The bartender opened a fresh bottle and placed it front of Jason on a beverage napkin. "Thanks," Jason said, slipping a five dollar bill in the bartender's tip jar.
"Thankyou, Mr. Ritt!" the bartender replied.
Just then, Cecilia came up smiling at her son. Her eyes were glazed over, showing the effects of a strong buzz. In front of the bartender, Cecilia spoke. "Jason, honey, I promised your dad's colleague, John whats his name, a bottle of the San Greggorio wine I love so much," she said. "I want to show that wine snob that the southern Italians can make good wine, too!" she continued, nearly slurring her words. Then she added, "Won't you be a dear and come help your mother find it, please?"
Jason glanced briefly at the bartender who was listening and gazing lustfully at Cecilia. The bartender noticed Jason's stare and turned immediately away. Jason looked at his mother, who was still gazing lustfully into her son's eyes. Well, at least Jason knew her stare was lustful! "Sure, mom," he said just above a whisper, "lead the way!"
Jason and his mom exited the main party room and made their way down to the basement, which led to the two thousand bottle, temperature-controlled, oak wine cellar that Jake had custom installed soon after they purchased the hundred year old home. Jason thought it odd that his mother was turning off each light behind them as he turned on each new light ahead of her. At the cellar door, Jason walked into the pitch-black room ahead of his mom. He turned on the light, thinking this one would remain on. But behind him, his mother turned the light off, as Jason turned toward her, confused. Checking to make sure it was unlocked first, Jason's mother then shut the door to the cellar, throwing it into complete darkness save for a sliver of light coming from the basement stair well and into the cellar through a small window built into the cellar and which looked out into the rest of the vast basement. Jake had installed the window for emergencies, in case anyone ever locked themselves in the room accidentally. Cecilia sauntered up to her son and kissed him hotly. Her tongue danced in his mouth as she rubbed her body shamelessly against him. Breaking the kiss, she said hoarsely, "I'm so horny, Jae-jae. I can't get your juicy cock out of my mind! Mommy needs to feel it inside her, again!" She turned, raised her dress to her waist and bent over, supporting herself against a wine rack. "Hurry, baby! We can't be gone long!!" She had flipped her hair and turned to stare back at him, running her fingers through her pussy lips. "Please!!!" she begged.
Jason hurriedly unzipped his pants and fished out his hardening cock. His mother licked her lips and groaned as she felt the head of his cock along her slit. "Mmmm," his mother moaned, adding, "don't tease me baby! Please!! Stick your cock inside mommy's pussy!!"
Just as Jason's cock had fully hardened, and he was about to drive it into his mother, they heard laughter from the basement stares. Instinctually, mother and son froze. Even though the lights in the wine cellar were off and the door was shut, Cecilia's heart was suddenly beating wildly. To anyone's eyes, there was no one present in the cellar, but nevertheless and with bated breath, Jason and his mother gazed at the basement stares through the window of the wine cellar. Leaning slightly away from the window, so that their bodies were mostly out of sight, they peered through the sparkling clean glass. Jason was still behind his mom, with his arms around her waist, as his half hardening cock nudged her backside.
"Shhhh!" whispered Cecilia to her son, upon feeling his cock against her asscheek. Jason was momentarily amused, as if his cock touching her would announce their presence! Suddenly, through the bottom of the basement stairs, Jake Ritt and his secretary, Cindy, appeared, giggling and laughing as Jake nuzzled her neck and felt her breasts.
Jake and Cindy remained in the dark, letting the light from the basement stair well light their way. "Over here!" Jake slurred, as he led Cindy to a huge, commercial-style, stainless steel table the Ritts often used to make traditional Italian delicacies like homemade sausage, bread and other delights. While they certainly had the money to afford buying such things, the nostalgic tradition of making them from scratch pleased Cecilia, reminding her of home. And so, once or twice a year, she would invite her Italian friends over and open up the basement for the festivity of making these homemade delights. Now, the spotless table held Cindy as she laid back upon its cold metal and squealed at the sudden feeling!
"Shhhh!" Jake said, laughing, "or my wife will catch me!!" he said slurring his words. "She'll make fucking sausage out of me!" He said, sarcastically. He struggled to maintain his balance, as he unzipped his fly, watching Cindy pull her dress up and release her tits from the restraint of her push-up bra. Panting, she ripped her frilly panties clean off to reveal a clean-shaven pussy, except for a tiny patch just above her clit. Jake stroked his cock as he watched Cindy massage a breast with one hand and run her other hand through her pussy as she gazed lustfully at her boss and spoke.
"Hurry, baby! I'm so fucking horny!" she whispered.
"You know what I like to hear, don't ya! C'mon! Say it!!" Jake said, roughly grabbing his secretary by the thighs and slamming his hard cock into her pussy.
"Ah!!!!" Cindy groaned from the impact, before coquettishly accommodating his request. "Yeah, daddy! That's it!! Fuck me with your big cock!!! Fuck your little girl hard daddy!!"
"Daddy?" thought Jason, as his cock began to harden from the action he was witnessing and hearing.
"Mmmm," Jake groaned, "you know the game I like, don't you?"
Jason couldn't believe his ears, as his father drove his cock into his secretary's wet pussy.
"Yeah, daddy! Yeah! Fuck me, Daddy! Fuck me hard!!" Cindy gasped, trying to keep her voice down, as she played with her fake but plump tits.
Jason glanced at his mom. In the sliver of light, he could see her face. Her eyes were moist as she quietly and secretly watched her husband fuck his secretary.
"Mom?" Jason whispered, concerned.
"Shhhh!" Cecilia whispered back, moving her hand back to his cock and stroking it. Jason's semi-hard cock quickly hardened, and Cecilia rubbed it against her juicy pussy, signaling to her son to continue what they had started.
Jason loved the idea of fucking his mom just a few feet away from his dad. He unzipped his mother's dress and freed her braless breasts. Wrapping his arm around her and massaging a breast with one hand, he used his other hand to sink his huge cock slowly into his mother.
"Mmmmph!" Cecilia groaned quietly, closing her eyes momentarily before opening them to continue watching her husband and Cindy.
"Yeah, daddy! Fuck me! Fuck your daughter!!! Slam your big daddy cock into me!!!" Cindy gasped, urging her boss on as he pounded his cock inside her.
"Ugh!!" Jake groaned, growing fatigued but continuing his efforts. "Fuck, you're tight tonight. Been a while, huh?" Jake grunted between gasps.
"You're...the...only...man...for...me...daddy!" Cindy gasped, continuing the game.
In the cellar, Jason was now slowly but rhythmically driving his cock in and out of his mother's pussy from behind, as she grunted with each thrust, continuing to support herself against the rack. Both watched Jake and Cindy fucking through the window, as Jason pinched his mother's nipples from behind.
"Ah!!! That's it, baby!!! Pinch mommy's nipple!!! Fuck me, honey!! Fuck me like your bastard father is fucking his secretary!!!" Cecilia mumbled a whisper, her eyes riveted to her husband and his secretary.
"Fuck! I'm close!!!" Jason whispered, his cock flexed as his orgasm approached. "I'm getting close, mom!!"
In the basement, Cindy strummed her clit as she continued uttering obscenities and encouragement to her boss. "Fuck me, Daddy!!! C'mon, Daddy! Fuck me, hard!! I'm gonna cum, daddy!! I'm gonna cum all over my daddy's cock!!" she hissed quietly, arching her back, as her orgasm approached.
"Fuck, I'm cumming, mom!!!" Jason uttered in the cellar.
"Mmmph!!!" Cecilia groaned, feeling her son's cock twitch and going over the edge herself. "Me too, honey!! Me too!! Ah!!!!!" She gasped, as Jason drove into his mother one last time and held his cock deep inside her. "Mmmm!!!!" she gasped, biting her bottom lip to stifle a scream.
"I'm cumming, daddy!!! Yes! Yes!! I'm cumming!!!"
"Ugh!!!" Jake groaned one last time as he drove into his secretary and shot rope after rope of salty cum into her womb. "Fuck!!!! I'm cum-ming!!!!"
"Yes, daddy!!! Cum inside your daughter!!!" Cindy continued with the game, as her orgasm peaked. "Ugh!!! Fuck!!! I'm cumming!!!" She gasped, as Jake covered her mouth with his to quiet her.
In the wine cellar, Jason slumped over his mother, as his cum-covered cock grew flaccid inside her. Both continued staring at the action beyond the window, where Jake Ritt slowly and reluctantly withdrew his cock from his secretary's pussy and pulled up his underwear and pants. Cindy used her torn panties to wipe her pussy before lowering her dress and placing the sticky undergarment in her clutch, which she carried everywhere.
Mother and son watched as Jake and Cindy cleaned themselves up, before Cindy walked up the stairs and back to the party. Jake hung around, checking his watch repeatedly until, after about ten minutes, he, too, made his way up the stairs and back to the party. Cecilia broke free from her son and straightened out. Jason did the same. Once they were both tidy, Cecilia turned on the light and, without hesitation, grabbed the wine bottle promised to their friend.
"I thought you needed help finding that?" Jason quipped.
"I lied," Cecilia said, walking toward the door, but stopping first next to her son and adding, "I just needed a good fuck from my son!" She smiled and kissed him lightly before heading out the door. Jason could tell her mood had changed to one of annoyance and anger that would be directed at her husband. She looked back at him through the window and smiled before heading up the stairs. Jason waited a few minutes and then retreated back to the party, which was coming to an end.
The final guest left the party at around one in the morning, and the staff began their clean-up efforts. Cecilia was making her rounds to each vendor to make sure payment terms were finalized, while Jake sat slumped in a recliner, continuing to drink. Inspired by the orchestra in attendance that evening, he had put some classical music on the stereo and was, now, conducting a phantom orchestra from his seat, an imaginary wand in his hand, as he waved his arm wildly, mimicking a conductor.
Jason watched his father with disgust. One hour earlier, Cindy had slipped Jason the tongue when she innocently hugged and kissed him goodbye, whispering "call me sometime" before walking out the front door. Jason couldn't believe the slut, who had just fucked his father, was now hitting on him! He had said nothing to her in response, and now he sat in a dining room table chair, silently nursing another beer, as his gaze shifted from his father to his mother. He was amazed at how quickly she had sobered up to take control of directing the end of the party. He watched as one-by-one, each vendor left: The valet, the orchestra, and finally the caterer, bartender and wait staff. Satisfied that payments were all taken care of, Cecilia walked passed her husband heading toward the kitchen, throwing him a disgusted look of contempt.
"Go to bed, you drunk!" She said in her pleasant accent. Jake continued conducting his phantom orchestra and just stared at her annoyingly, as she walked past. Cecilia walked past her son and grinned, tussling his hair and adding, "Want to help your mother clean up?"
"Isn't that what cleaning services are for?" Jason said sarcastically.
"Yes. I'm not doing much. I'm not tired yet, so I just want to pick up a bit. C'mon, it's therapeutic. It gets my mind off of things," she said, reaching the kitchen sink and shooting a grin back at her son. "You can start by helping the drunk bastard over there to bed!!" She added loud enough for her husband to hear.
"Go to hell!" Jake slurred loudly. "I'm conducting..." he added before losing his train of thought and waving his imaginary wand.
"C'mon dad," Jason said, reaching his father and helping him up.
"You did an excellent job with the music, tonight Jae-jae! Excellento!!!" Jake mumbled as his son helped him up the stairs and to the master bedroom.
Jason couldn't help recall this same scenario a week or so earlier at the wedding reception, when he used his father's intoxicated state to help him seduce his mother. Jason grinned to himself, before replying, "Thanks." Upon reaching the master bedroom that his mother and father shared, Jake turned and slapped his son lightly on the cheek before mumbling, "Your mother says you're a good boy. I don't see it, but if she's happy, then I'm happy!!" he said laughing at himself. Jason just stood staring at the man making a fool of himself. "So go be a good boy and help your mother!!" Jake slurred, gesturing with his hand toward the kitchen; fighting to maintain his balance.
"Go to bed, Dad," Jason simply replied. Jake turned and stumbled toward the bed. He attempted to remove his tie before losing his balance and collapsing on the bed. He was out within seconds.
Back in the kitchen, Jason began helping his mother, as she asked, "How is he?"
"Out cold. A fucking earthquake won't wake him!"
"Good," Cecilia said matter-of-factly, as she wiped her hands and moved into her son's arms. The house was now empty save for the three family members. Cecilia kissed her son hotly first, before whispering seductively, "mommy wants you to do her a favor."
"Oh yeah?" Jason grunted, returning his mother's kisses and adding, "What's that?"
Cecilia's voice dropped to a whisper as she said, "I want you to fuck mommy up the ass!" And with that, she nibbled on her son's earlobe before rubbing his cock through his pants.
"What? Right now? Here?" Jason said, his cock hardening as his mother turned and raised her hair, signaling for him to help her with her zipper.
"Yes," she simply replied, shimmying out of her dress and standing only in heels, hose and garter belt. Her naked breasts hung perfectly, as their nipple hardened at her son's stare after she turned back.
"What brought this on?" Jason asked, watching his mother kneel, unbuckle and shed his pants and underwear in one fell swoop.
"Your father did," she replied, adding venomously, "that no good son of a bitch! I'll show him!!" She rose and stroked her son's cock. "What better way to get back at him than to let his son fuck his wife up the ass?" She hissed. "Besides, isn't that what you've been wanting to do to mommy?"
Jason's cock was fully hard now as his mother helped him remove the rest of his clothes. "Well....yeah....but....are you sure? Now?"
"Yes!" His mother replied curtly!
"Okay, okay!" Jason responded, holding back an amused laugh at his mother's insistence.
Once naked, Cecilia retreated to the dining room table and laid back. "Eat me, first, honey! Make mommy's pussy nice and wet first!" she said, as Jason knelt and dove into his mother's moist pussy, which she now kept shaved for her son. Cecilia made no effort to keep her voice down, as she groaned and moaned in delight of her son's actions. After a few moments, she grabbed a handful of her son's hair and gasped, "Lick my asshole, honey. Mommy's nice and clean down there. Lick it and get it ready for your hard cock!!" Cecilia pulled her legs back and spread them impossibly wide, opening up her puckered nether region to her son's delight.
"Ugh, fuck!" Jason mumbled, thinking his cock would explode upon hearing his mother's words, while he trailed his tongue from her slit to her rosebud, licking the wrinkled edge before stabbing it repeatedly.
"Oh, fuck!!" Cecilia gasped, running one hand through her hair and another over her breast. "Yeah, baby!! That's it!! Lick momma's asshole!!! Get it nice and moist for your big cock!!! Mommy can't wait to feel her baby boy's cock up her ass!!"
"Mmmmph!!!" Jake mumbled as he stabbed his tongue deep into his mother's rectum before spotting the butter dish just next to her on the table. Reaching over, he sunk two fingers into it and brought them to her pink hole. He smothered her rectum with the quickly melting fat as he licked and sucked her clit.
"Oh!! Fuck, baby!!! What are you doing to mommy? Yes, I like that!!! Mmmmm," Cecilia moaned, unaware of the butter being spread across her hole.
Once the area was lubricated and his fingers were coated, Jason easily slipped his index finger into his mother's asshole, stopping at the second knuckle, while licking and sucking her pussy frenetically!
"Ah!!!! Fuck!!! Yes!!!!! That's it, Jae-Jae!!! That's it!!! Finger mommy's asshole!!!! Slide your finger in and out!!!! Oh, fuck!!!!"
Up the stairs and in the master bedroom, Jake Ritt snored loudly, passed out from his love of highballs. His wife's echoes urging their son to finger her asshole carried into the bedroom, but he was oblivious to them.
Jason continued eating his mom's pussy as he slowly slid a second finger into her asshole, opening her up in preparation for his cock!
"Oh my god!!! Ugh!!! Fuck!!!!" Cecilia screamed, as she grasped a handful of her son's hair and hissed at him!!! "Yes! Yes!! You fucking bastard!! You fucking mother fucker!!! Fuck mommy's asshole harder!! Harder!! I want you to fuck my ass hard!!!! Ugh!!!!!" She screamed again, biting her lip and nearly passing out from the overwhelming feeling of fullness and desire! When she couldn't stand it any longer, she rose and turned, bending over against the edge of the table and laying face down on it. She reached back and spread her cheeks apart with her hands, as she gave a slutty look at her son and hissed, "C'mon, sweetheart!!! It's time!!! Fuck your mother's ass!! I want it hard and fast!!!!"
Across town, in an elegant one-bedroom apartment, located among rolling hills smattered with trees, Cindy panicked. The wet panties she had torn off were nowhere to be found! She was rummaging through her purse and retracing her steps in the apartment since coming home, but it was no use. They were gone! Her heart beat wildly as she thought about where they might be and what to do. Perhaps, Jake had secretly retrieved them for keepsake? Or maybe, they had fallen out, which on one hand would be bad, but then again, no one would know to whom they belonged, except maybe Jake. And he sure as hell wouldn't talk. Cindy exhaled deeply and began to undress, deciding it wasn't worth worrying about. She cleansed her face and slipped into bed, glad she could sleep in the next morning.
"Oh, fuck, yeah baby!!! Fuck mommy's ass!!! Fuck it hard!!! That's it!! That's it!!! Fuck me, Jae-Jae!!! Fuck mommy's ass harder!!"
Jason slammed into his mother, as his cock pulled tightly against her sphincter wall with every retreat. The alcohol and the events she'd witnessed earlier in the evening had turned her into a woman possessed, as she begged her son to cum deep inside her asshole.
"Cum for mommy, baby!!! Cum inside my ass!!! I wanna feel you cumming deep inside me!!!!"
"Fuck!!" Jason gasped. "I'm gonna cum!!! I'm gonna....fuck!!! I'm cumming mom!!!!" Jason screamed, as his cock tried desperately to flex inside her tight anal opening. The sensation overwhelmed Cecilia, who had been strumming her clit, and it sent her over the edge too.
Mother and son screamed, as load after load of copious semen filled Cecilia's anal cavity. Her son dripped with sweat as he tightly gripped his mother's hips. Cecilia herself shook uncontrollably as shivers ran through her body, causing her rectum to contract and her son's cock to flex yet again and again in response. The contracting rectum and flexing cock tagged teamed off of each other, resulting in one of the most intense and longest orgasm mother and son had ever experienced, with anyone!
