A Night on the Town

Jessica and Caleb have a unique mother/son relationship. They are loving son, doting mother and longtime kinky lovers.

WARNING! This story contains incest, anal sex, lesbianism, bisexuality and probably a few other kinks and perversions. If ANY of these offend you, move on!

*****

The strident sound of the doorbell pulled 30 year old Caleb Moore from a sound sleep. Groggy, he sat up in bed and wiped the sleep from his eyes. He fumbled in the darkness for his cell phone. The display said it was 2:30 am. "Who the fuck is that," he grumbled?

The bell rang again as he sat up on the side of the bed. "Okay! Okay! I'm coming," he yelled at the door. Since he usually slept naked, he grabbed his mid thigh silk robe from the back of the overstuffed chair in his large bedroom and tied it loosely.

He stretched, his hands above his head, as he made his way from his bedroom with its waist high walls, through the open plan living area of his lakefront home to the front door. He half expected who it was. Still, he sighed with resignation when he opened the door. His mother was leaning on the door sill preparing to ring the bell again.

"Mom! What the hell? It's 2:30 am!"

Forty eight year old Jessica Adams swayed drunkenly as she blearily eyed her tall muscular son. His skin had a light permanent tan, the result of having a White father. She pushed past him in a miasma of Creed Royal Mayfair perfume, gin and the faint odor of marijuana. Her Oscar De La Renta classic sheath cocktail dress in a gradient ombré hugged her full hips. It was sleeveless with the hem stopping fashionably just above the knee. Her matching strappy 4" CFM heels clicked unevenly as she stumbled across his hardwood floor. Her carefully manicured toe and finger nails were painted a pearlescent pink.

Ruefully, Caleb shook his head as he watched the soft sway of his mother's hips as she moved past him and into his living room. He marveled at the miracles a Brazilian butt lift, breast augmentation and other surgical nips and tucks did for his mother's body and face.

Her D cup breasts and round sensual ass were proportional at 38". Her 28" waist gave her an overall hourglass figure. Her triangular face was smooth and unlined with wide set eyes, and fashionable bee stung lips. Typical of her Creole heritage, her complexion was coffee latte... with lots of latte!

"I just left him! He just doesn't understand me darling."

"Who doesn't understand you?' Caleb followed his mother as she walked over to his bar.

"Sergio! Who else! I need a drink!"

Jessica, never Jessie, had a penchant for young men with foreign sound names. She collected them like she had her three husbands. They were like accessories to finish off a designer dress as she made the rounds of the cocktail parties, charity events, and the other activities of the idle rich. Her wealth was the result of generous settlements with her ex-husbands.

"Mom, you don't need anything else to drink!" He leaned over and inhaled. "Or smoke! Where is Sergio?"

She sat at the bar and crossed her legs unladylike with one ankle on her knee. She wore black patterned nylons. He caught a glimpse of mauve lace panties. Around her son she dropped her sophisticated airs. She became what she was: a bayou urchin with a huge sexual appetite and a magnet for wealthy men.

"Sergio? OH! Sergio! I left him at a cocktail party! He just doesn't understand me! Fix me a dry martini! Nobody makes them like you do!"

"Mom, the last thing you need is...!"

"Please, baby, please!" Jessica pouted using her little girl voice. She scooted forward on the stool, her arms extended. Her dress road up, barely covering her nether regions.

Caleb sighed, stepped between her outstretched arms and embraced his inebriated mother.

"I'm going to call you an Uber and send you home!" He broke the embrace, stepped back, and pulled his cell phone from the pocket of his robe.

Jessica slid off the stool. Her dress slid up around her waist. Caleb paused dialing. He could see her lace sheer panties covered a bald pussy.

"When did you get rid of the landing strip?"

"Do you like my pussy bald?" She held the hem of her dress up with one hand and pulled the gusset of her panties to the side. Her butterfly labia gleamed wetly. "I decided to get a bikini wax!"

Caleb stopped dialing and walked over to where his mother stood leaning against the barstool. He cupped pussy, his index finger slipped between her folds. He wriggled it around then took it out, stuck it in his mouth, sucked her juices off his fingers then offered his finger to her to finish. With a lopsided drunken grin, Jessica took her son's finger in her mouth and sensuously sucked it. Their eyes were locked on each other.

"Mom, you know I just love your pussy!"

"Mmm! You naughty boy!" She leaned forward and cupped her son's cock through his robe, running her open palm over it. "Now fix me that drink!"

He sighed and walked behind the bar. He poured gin into the shaker along with ice. Caleb looked at his mother leaning on the end of the bar. Her dress was still up around her waist, her butterfly pussy lips gleaming wetly. He smiled at her, whispered vermouth over the shaker, stirred it and poured her drink.

"While you drink that, I'll call an Uber for you."

Jessica took a sip of her drink. "Aww pooh! You're no fun! Why can't I stay here tonight?"

"Mom, that would be the fourth time this month. You're practically living here."

She looked at him and smiled. "Would that be so bad?"

"Yes, it would! We agreed years ago to live our separate lives. Lately, I've become your booty call! Every time you get drunk, or break up with a boyfriend or both, you come here and we fuck."

Jessica walked behind the bar. She sat her glass on the bar, stood on her tiptoes and wrapped her arms around her son's neck. She was barely 5' 2", fully a foot shorter than her 200 pound son. "You don't like fucking your mother," she simpered.

"Mom, you're an incredibly fuck! I love everything about sex with you. But you can't just wander in here, fuck me and go back to the flavor of the moment. I'm tired of being a stand in for your boyfriends."

Her hand slid between them. She pushed aside his robe and took his cock in her hand. She stroked it slowly. Jessica stood on her toes and kissed him passionately, her tongue outlining his lips. Caleb gently pushed her away.

"You know you're the most important person in my life." Jessica tried to kiss her son again.

"Mom! Stop it! You know you know where this always leads."

"I won't mind! I love the way you pound my pussy!"

Jessica sank to her knees. She smiled up at her son as she pushed aside his robe and took his cock in her hand. Using both of her hands, one just above the other, she stroked it slowly, her fingers unable to touch around it. Still looking up at her son, she pushed back the foreskin. Slowly, with exquisite patience, she licked the length of Caleb's cock from his balls to his glans and back again. Her tongue was almost prehensile, grasping and turning around its girth as she made love to his tool. She treated it like a large chocolate all day sucker, running the flat of her tongue up and down its length. She savored its familiar taste and feel. Each time she reached his glans she puckered her lips and lavished it with kisses, tonguing the slit. She sat back on her heels, still stroking his tool.

"Do you like it when mommy makes love to your cock?"

He grabbed a handful of her hair and roughly pulled her head back. "You know you're the best cocksucker ever." His cock was streaked with her bright red lipstick. Her lips glistened wetly with her saliva and his pre-cum.

Shocks of pain and pleasure coursed through her body. Her cunt pulsed. "Better than that red headed White bitch you've been dating?"

He released her hair. Jessica swayed drunkenly nearly keeling over as she knelt on the floor in front of him. Her large chest heaved. A sheen of perspiration covered her face giving her a wanton look. There was no doubt he loved her and she loved him.

However, he decided their on again off again affair had to end. It prevented both of them from moving on with their lives. Tonight was as good as any to tell her.

Jessica leaned in and blew her warm breath lightly on his wet shiny cock, sending shivers up Caleb's spine. And then there was that! The sex was incredible! It always had been.

She took the first two sensitive inches of her son's cock in her mouth. She bobbed slowly, her lips, applying light pressure to the nerve packed area around his glans. His moans and the tremors of his body told her she was pleasing him.

His hand resting on her head, Caleb looked down at his mother's head bobbing slowly on his tool. Her eyes were up cast, watching him, her lips puckered around his dick. Her cocksucking skills were incredible. Long ago, she taught him how to suck cock. Back in the day they often they shared cocks and pussy.

He recalled a few years back when they took a life style Caribbean cruise. They met the Kranes, Amelia and John. They hit it off immediately. John and his wife were bisexual like Jessica and Caleb. For most of the cruise they swapped partners. He still had incredible memories of 69ing with John, his mouth full of his amazingly large cock, while it spewed a seemingly endless stream of cum into his mouth. On the same bed his mother and Amelia noisily ate each other out. The contrast of his mother's coffee with cream complexion on Amelia's pale freckled skin was astounding.

He looked down at his mother lavishing his dick. He was not sure what he enjoyed most, fucking her or watching her being fucked. He remembered holding his mother's hand as he fucked Amelia while John fucked Jessica next to him. After he and John came, they swapped. Caleb licked Jessica's pussy clean while John did the same to his wife. The taste of another man's cum in his mother's pussy was a heady nectar he never got tired of drinking. Long ago, he realized in addition to being mother and son, they were sybarites. They loved the hedonism of unrestricted sex.

"Fuck! You had better stop before I cum!"

Jessica pulled his cock from her mouth. She stroked it slowly as she looked up at her son. Her eyes were at half mast, her lips moist and shiny. Saliva bubbled at the corners of her mouth and ran down her chin. "Isn't that the idea," she said, smiling wickedly.

"We need to talk," he said brusquely. Caleb grasped her under her arms and pulled her to her feet. "First, Calista is a nice girl. You shouldn't call her names." He paused. He planned to tell her about his engagement. Now was as good a time as any. "As a matter of fact, we're going to get married!"

"You're what," Jessica exclaimed! Her eyes widened in shock, her mouth gaped open.

"I'm getting married," he said quietly.

"You can't do that to me!" She began crying softly, her hands beating lightly on his bare chest. "I love you!"

"And I love you also! But I want something more...traditional...and I want kids!"

She pushed away from him and walked around and sat on a barstool. She hung her head, staring at the bar. "So, you still hold it against me because I aborted our baby?"

Caleb moved quickly around the bar. He wrapped his arms around her from behind, cupping her large breasts. He caressed them gently as he spoke. "I do not!" He said vehemently. "You were right. I was just out of high school with my life in front of me."

"I was scared! Not of having your baby! I wanted that more than I wanted life itself. Back then I was worried it would change what we had."

Caleb squeezed his mother's soft breasts and kissed the side of her neck. When he was younger, their relationship confused him. His small circle of friends chased the local skirts and crowed about their conquests. So did he! He got more than his share of stray pussy. The word around school was that he was an excellent lover. However, most nights he slept in his mother's bed. Most nights they made loud passionate love.

The only time they did not sleep together was when she found a new husband or boyfriend. Initially he was jealous. However, no matter who else was in her life only the frequency of their lovemaking decreased, not the passion. They loved each other as only a mother and son could.

However, this was the first time he would not be available to her. Now she was jealous and possessive. Like any mother, she was sure no woman was good enough for her baby.

"Maybe, we could have worked something out." She covered his hands on her breasts with her own, and leaned back, laying her head on his bare chest, tears streaming down her face.

"Stop it! You did the right thing! Now stop crying!"

"I want your baby! As I get older, now more than ever. I'm just scared...scared," she wailed.

"Mom, we don't need to start a family. You've been a great mother." Caleb spun her around. He kissed her forehead, her nose, making her giggle. He moved down, planting kisses on her lips, chin and neck. He continued down, sucking gently on each nipple, then tonguing her navel.

He knelt between her legs, pushed her dress up and kissed the moist gusset of her panties. He looked up at her "How many mothers taught their sons how to eat pussy?"

"Do you still like licking your mommy's pussy," she asked huskily?

Caleb pulled the gusset of her panties aside with his teeth. He looked up into his mother's luminous eyes, still wet with her tears. He leaned forward, puckered his lips and French kissed her moist pussy lips.

"The question is: Do you still enjoy having me lick you?"

Jessica took her son's head in her hands as he leaned forward and kissed her labia. She loved the familiar intimacy of their foreplay. The alcohol/reefer fog had lessened. However, she still felt out of body. Her son didn't just lick her pussy, he worshipped it! No other man understood that. No other man did that! The way he used his the flat of his tongue to spread his saliva over her labia drove her wild.

"You know I do, momma!"

He took her engorged labia in his teeth and pulled gently on it. His mother's sibilant hiss told him she was enjoying it. Unlike her many lovers, he knew her erogenous zones intimately and all of her kinks.

She taught him what she needed. He recalled laying between her thighs while she instructed him in the mysteries of vaginal anatomy. It was not all work. She teased him that practice made perfect. They practiced a lot!

Caleb slipped his tongue between her pulsating cunt lips. He French kissed her pussy, pressing his face tightly into her wetness, forcing his tongue deep in her hole.

"OH! Baby you making your momma feel so good!"

Her wetness covered his face nose and chin as he pushed his tongue between her engorged pussy lips. He tongued her pussy long and hard, wriggling his tongue in her hole. When she began to whimper, he pulled back.

"Does Sergio kiss your love hole like that?" Caleb stood. His cock poked rigidly through his robe.

"Mmm! Baby, no body kisses your mommy's pussy like you do?' She wrapped her arms around his neck, pulling his head down. Jessica lovingly licked her son's cheeks, savoring the taste of her pussy and the roughness of his unshaven face. She pulled back and looked into his eyes.

"You're right! I do taste good," she tittered. "Are you going to fuck me now?"

Caleb smiled wickedly. He pushed her panties aside. It always came to this. They could not get enough of each other. He positioned his cock at her entrance. "Who are you," he asked huskily?

"Aren't you going to let me get undressed, to take me to bed?"

Caleb slapped her bare thigh. The sound resounded through the room. "NO! I'm going to treat you like whore you are! Now who are you?"

"OUCH! You're so mean to your mother," Jessica smiled. She felt the head of his cock pressed against her pussy lips. She knew what she needed to say. They were going to play their D/s game. She shivered. She loved it when he dominated her, made her do nasty things. "I'm your slut, your mommy slut!"

He pressed forward, his glans parting her swollen cunt lips. "Go on!" His cock sank slowly into her moist, quivering love hole. The sensation of his cock sliding into his mother's pussy sent chills through his body. He had fucked lots of women. None was better than his mother's pussy.

"I'm your mommy whore! I'll do whatever you say, do whatever you want!"

Jessica shivered. It was always like this when she felt him entered her. The sensations coursing through her body were almost other worldly. She felt the head of his cock press through her pussy, opening her up.

Caleb fully into his mother's pussy. He felt his balls slapped against her ass. Still fully dressed, her expensive dress rucked up around her waist, her panties pushed to the side, Jessica wrapped her legs around her son's waist.

She relished the times he took her like this. She felt exposed and controlled. She recalled the times they walked in the park at night. She wore only her dress, stockings and heels. They would choose a bench under a street light. There they would fuck. Sometimes people walked by. Some giggled and walked on. Others stopped and watched. One woman actually leaned in and kissed her nipple! Then hurried on! None knew they watched a mother and son.

A strong woman, she loved it when her son dominated her. No other man could. She was her son's whore and she loved it. She leaned back, her back resting against the bar, her panty covered ass on the edge of the bar stool.

He maintained a slow even stroke in and out of her pussy. "Do you remember Carlos?"

"Yes! Yes! I remember him! You walked in on us at my house. You pretended to be my boyfriend. You made him suck you off before you let him get dressed and leave."

"He was good at it! I think he did it before!"

The squishy sounds of her arousal competed with their harsh breathing. "Did you like watching another man suck my cock?"

"I was jealous," she cried, "especially when you came in his mouth! I like it better when we share a woman! Please baby! Take me to bed!"

They both hissed as he pulled back. His cock exited her pussy wet and gleaming. Caleb grasped her waist and lifted her to the floor. "Turn around."

Caleb grasped her zipper, pulling it down. He pushed the dress off her shoulders. Jessica wriggled her substantial behind and it fell in a silken puddle at her feet. Caleb stopped her when she started to turn to face him.

"Lean on the stool!"

"Have I been a bad girl? Are you going to spank me?" Her son's large powerful hands smacked her ass. Jessica bit her lip suppressing a cry of pain. She resisted the instinct to reach back and rub her stinging ass. It was not permitted. She was bad and she was going to be punished. She groaned as he spanked her again.

"Take off your panties and go to the bedroom! Just your panties! Keep your stockings, heels and bra on!"

Jessica hooked her thumbs into the elastic of her sheer mauve panties. She leaned forward slightly and slipped them down over her hips and legs. She stepped out of them and tossed them to the floor.

"Go into the bathroom and get the Astroglide!"

She shivered and her anus clenched at the import of those words. He was going to fuck her ass! It was not unusual for her son to want her ass. They did it often. However, combined with the spanking her and making her keep her bra, nylons and heels on, she knew he was expressing his dominance.

It was like when he was in his second year of college. He and two of his frat brothers shared an apartment. She missed him terribly! It was November and she had not seen him since August.

It was mostly her fault. She and husband number two spent the Fall touring Europe. When they returned, she called him to ask if she could come visit. He told her if she did, she would have to fuck him and his roommates all weekend. It was incredible to have three horny virile young men use her like a two dollar whore. She undressed at the door of the apartment on Friday afternoon and did not put any clothes on until she left that Monday morning. Most of that time she had a cock in one of her holes. A few times she was airtight, all holes filled by a youthful dick.