Pleasing Mama

This story focuses on the theme of incest. If this doesn't interest you, please do not read further. Thanks for your time.

Vincent sat in first class, sipping on a beer, pondering how he had gotten to this point in his life. He was finally going home for the first time in over five years. He knew it would not be a joyous return full of hugs and smiles. Nobody outside of his family would even notice nor care if he was back. He had been a nobody in a small town, a nerd, a skinny weakling. He expected a lukewarm reception from his older sister and believed that his mother would actually shun him completely. The last time he spoke to his mother was right after his father had passed away.

She had called him a coward for leaving his family in a lurch to go to college on the west coast. His relationship with his mother had often been contentious, especially as he entered his teen years.

Vincent was the youngest child of a poor family and grew up in a small row home in northeastern Pennsylvania near Scranton. His mother was loving enough when he was a boy but she grew angry and bitter over time. She hated her life and blamed Vincent's father for their financial situation. She would often call her husband a loser and a failure within earshot of the kids. She would say things to needle her husband and try to make him angry. She'd call Vincent a weakling and tell him he would grow up to be a loser like his father.

By contrast, his mother would dote on his sister, Maria. Maria could do no wrong in her mother's eyes. She was the spitting image of her mother with dark hair, green eyes, short and petite, with large breasts. Maria was four years older than Vincent and had two children. She married right after high school and moved into a run down rowhouse across the street. Her husband was a popular jock in high school, one of the cool kids. He worked in construction after he married Vincent's sister but he seemed to spend more time talking about his next job than actually working.

Vincent's father was a true man's man. He was tall and strong, a football player in high school, and a mechanic for over twenty years before he passed away from a heart attack. Vincent, on the other hand, had always been skinny, didn't play sports, and liked reading comics and coding. Vincent didn't need the constant reminding from his mother that he was a weakling. He was a nerd in school, never liked working out, and often got so lost in his books or working on the school computers that he forgot to eat. Vincent was also a late bloomer and didn't start hitting puberty until his junior year of high school. As a result, he was pale and looked sickly. The jocks in school would sometimes bully him but most of the time he was simply ignored and had no friends. His sister had tried to help him by telling him the things he needed to do to be cool and fit in but Vincent simply didn't think it was worth the effort.

Vincent's awkward teenage years were made even more confusing by his mother's treatment. She would insult him on a daily basis but then would occasionally give him a hug and cook him his favorite meal. His father would rarely respond when his mother became angry but would be very defensive when she insulted Vincent.

This would typically result in more insults like, "Why don't you get out of the house and take your weakling son?" or "I didn't think it was possible, but your son is going to grow up to be even less of a man than you are."

Vincent's dad would pull him aside after her outbursts and tell Vincent how proud he was of him. He would tell him to follow his dreams and do what makes him happy. Vincent often thought his dad died because he simply couldn't stand living with his mother anymore. Vincent had just graduated high school when his father passed and his mother told him he needed to be a man for once and get a job to help support the family. She told him it was his duty to care for his mother. Vincent didn't have the courage to tell his mother he had gotten a full scholarship to college. Instead he worked all summer, kept the money for himself, and then just up and left for college in California, leaving his mother a short note explaining that he needed to follow his dreams.

That was over five years ago and he had not spoken to his mother or sister since that day. College had been the right choice for Vincent in all aspects except for women. Vincent had lost his virginity in his sophomore year of college to a chubby girl named Susan he met in one of his classes. He thought they were in serious relationship, Vincent even thought he was in love, and they dated for over a year before she dumped him for being too focused on his academics. She was condescending and cruel about the breakup. She told Vincent he was boring and he would probably never find a wife, she also told him the only reason she stuck with him so long was because he had a really big dick. Vincent was extremely hurt and confused after the breakup. Vincent promised himself that he wouldn't get hurt like that again, he doubled his focus on his academics, and gave up on looking for love.

The next semester one of Susan's roommates, who had a serious boyfriend, approached him at the library and offered to walk him home. They had sex later that night. When Vincent asked why she was cheating on her boyfriend with him, she said Susan had told her how big his dick was and she just had to see it for herself. Weeks later, a second friend of Susan's, who also had a steady boyfriend, conveniently bumped into him on campus and he had sex with her as well. She told Vincent a similar story about just wanting to try out his dick after hearing Susan talk about it so often. Both girls told Vincent he could fuck them anytime he wanted and Vincent would call them on occasion to blow off steam. Vincent knew he was being used but relished the fact he was cuckolding their boyfriends.

Vincent's highlight of college was when he met Andre, a Russian immigrant with a passion for coding and comics. They hit it off immediately and had been best friends ever since. Together they had created a software that was able to crack certain viruses almost twice as fast as anything else on the market. They formed a company and had already gone through one round of angel investing. Vincent sold a small portion of his equity for over twenty million dollars in the first round and they were planning a second raise later in the year.

Over the last year, Andre and Vincent had taken a portion of their proceeds and used it to hire over ten engineers who worked around the clock to improve their product. In preparation for the second round of equity raise, they decided that Andre would handle the west coast and Vincent would work the east coast private equity firms. Vincent bought over ten acres on a mountain about 30 minutes from his hometown and less than two hours from where much of his fundraising would occur in New York City.

The house he had built was finally complete. It was over twelve thousand square feet, had a large pool, and gated grounds. He originally planned to go back to his hometown in a limo with tons of fanfare but later decided he would savor the moment. He devised a different, more grandiose, and devious plan. After his flight landed, Vincent drove through his hometown. It looked the same to him; dreary, poor, and drab. He pulled up to his childhood home in a late model Jeep and parked on the tight street. Despite it being almost 6pm, the temperature was still well above 90 degrees and he wiped the sweat forming on his brow. He barely recognized his childhood home, it had obviously been freshly painted and there was a new rocking chair on the small porch, the air conditioner in the window hummed softly. He knocked on the door nervously.

A strange woman answered the door, "Hi, can I help you?"

Vincent stammered, "Oh sorry, I was looking for my mother. She lives here, I mean used to live here."

At the mention of Vincent's mother the woman frowned, "Oh, we bought this house off her a few years ago. She lives across the street with her daughter."

Vincent thanked her and walked over to his sister's house. The paint was peeling and the house needed new windows. Her husband was a poor excuse for a contractor, Vincent thought idly. He walked up the steps and nervously knocked on the door. Moments later, the door opened and he was greeted by his sister's shocked face. She stood wordlessly for a moment, sweat beading on her head, as he looked her over. She had her black hair pulled back in a ponytail, she wore a white low cut tank top with a black bra underneath, and tight yoga shorts. Vincent thought she looked amazing and simply said, "Hi, Maria."

"Vincent!", she yelled finally and threw her arms around his head. He held her for a few moments enjoying her curves pressed against him when he heard his mothers voice, "Who is it Maria? Get back to the dinner table."

Vincent stepped into the small dining room and saw his mother, Tony, and Maria's two children seated around the table with a large pot of spaghetti in the middle. It was boiling hot in the room and they were all sweating. The air conditioner either didn't work or they never turned it on.

"Hi mother," Vincent said cautiously.

"Oh it's you, I was wondering when you would come crawling back," she said venomously.

Tony looked him over and said laughingly, "Hey Skinny Vinny, did you find a boyfriend out in California or what?"

Vincent hated being called skinny, he was still skinny but worked out a few days a week and ate much better now. He thought of himself as athletically thin.

"No boyfriends in California, Tony. Look Mother, I didn't come here to fight. I have an offer for you, sorry to interrupt your dinner. I will be outside when you are finished."

"Stay Vin, have some food," his sister pleaded.

"Thank you Maria, but I will wait outside."

Vincent sat in an old chair on the porch for almost an hour before his mother casually walked outside turning to close the door. Vincent thought she looked great despite being 44 years old. She resembled Raquel Welch or an older Camilla Belle. She was still fit, had large full breasts and what looked to be a firm ass. She didn't have any makeup on but she was a natural beauty even with the resting bitch face look. She wore a loose fitting t-shirt and capri pants.

She crossed her arms under her large breasts and said, "Well spit out, I haven't got all night."

"I made a friend in college who started a company and owns a mansion in the area from which he is raising money. I am in charge of keeping it in order and assisting with the capital raise. I am authorized to hire someone to care for the place and do some cooking. I would like to offer that position to you, Mama."

Vincent's mother was about to speak but Vincent cut her off, "Before you answer, it pays $100k a year."

Her face dropped and she forgot whatever she was about to say. "A hundred thousand dollars to cook and clean?" she asked skeptically.

"Yes, he is a wealthy individual. Two weeks pay in advance as well," Vincent added.

His mother stood there pondering, but Vincent was confident his mother's greed would kick in. Vincent didn't know but Mama had a part-time job at the dentist office and she hated it. The dentist often tried to ask her out but she ignored his advances. She considered him a loser like everyone else in town. She spent most of her free time reading romance novels and imagining she was anywhere else but this terrible town.

"I will do this thing," she said begrudgingly.

"Ok, you can start tomorrow, I have uniforms in the car that must be worn as well as written job instructions and directions. Do you have a car?"

"I can't afford a car, since you left us all alone. Couldn't afford to pay the mortgage either," She said accusingly.

"The company will pay for a rental. It will be here tomorrow morning at 9am. I will see you at the mansion."

Vincent smiled all the way home, thinking that his plan just might work.

The following morning, Vincent watched his mother walk up the long pathway from the lot to the house. He had watched her pull in on one of the security cameras. She wore the outfit that Vincent had provided and she was obviously uncomfortable. The top was an extremely low cut v-neck that exposed her ample cleavage. The leggings were tight yoga pants and left little to the imagination. His mother was very traditional and Vincent could count on one hand the number of times he had seen her wear clothing that revealed her cleavage.

"I see the uniform fits well," Vincent said slyly.

"This outfit is ridiculous, just show me what needs to be done," his mother barked.

Vincent could see the awe in his mothers face as he gave her a tour of the facility. Huge vaulted ceilings, deep dark hardwoods, and marble stairs. Vincent took his time showing her his massive bedroom on the top floor with an expansive balcony overlooking the grounds.

"Where are all the other people? You actually live here?" she asked.

"It is just me for now, the living arrangement is part of my compensation. There will be meetings on occasion but most of the time it will just be me and you here."

"So I am just cooking and cleaning for you?" she said angrily.

"No, for the company. We must keep up appearances for when visitor's come."

For the next three weeks, Vincent took pleasure in his mother resentfully bringing him meals and cleaning rooms that were already spotless. He would often watch her on the security cameras polishing the tables, her large breasts swaying back and forth as she worked the polish in circles. It was time to unleash the next phase of his plan but he had doubts that it would work. His mother had still not acknowledged what he had done for her by giving her this opportunity nor had she said thank you. In fact, she had barely spoken to him at all.

"Mother," Vincent said as she dropped his lunch on his desk, "Do you know any girls in town who could use a job? Preferably a pretty girl? We have a new job opening for an assistant that pays very very well."

"Your sister, give your sister the job. She hasn't forgotten you left the family either," she said.

"No Mother. You don't understand this job requires some, umm, discretion and a special skill set. That's why it pays double your position."

"Double? What skills?" she said excitedly.

"Well, my boss is a very unique person and has some new and extremely progressive beliefs on how to succeed. You see Mother, he believes I am not living up to my full potential because my mind is not clear. I need an assistant to help me a few times a week to release thoughts that are not conducive to success."

Vincent had concocted the guru boss story one night while laying in bed. He needed to place some distance from the wealth of his company and himself. If his family knew he had millions in the bank they would just want handouts.

"You are making no sense, speak plainly," she said.

"I need a woman to release, you know," Vincent said while making a jerking motion with his hand in his groin area.

Vincent's mothers eyes grew wide in astonishment and she muttered something in Italian.

"So you see," Vincent continued, "It should not be Maria."

"Why not do this thing yourself? I am sure you are an expert," she said while laughing at her joke.

"My boss believes it needs to be performed by a woman, to do it alone is to create more unwanted thoughts."

Mama stared at her son, deep in thought. Of course, she thought, he has become a pervert, being a loner and a weakling has led to him paying for women to get him off. It was her dead husband's fault for not making him a real man. Her loser husband was still tormenting her from the grave with his mistakes. However, Mama pondered, the amount of money being offered was probably too much to pass up. Could she jerk off her perverted son if it meant getting out of debt and that sorry town?

His mother stared at him for a few moments and finally said, "I will do this thing, if you give your sister my position."

Vincent was shocked his mother agreed so quickly, he expected it would take much longer.

"I couldn't let you do it Mother. It's not right. My boss will know if I don't do this, I cannot lie to him."

"I do this for the family, unlike you and your selfish ways when you abandoned us. Give your sister the job and I will do this for her and my grandchildren," she said sternly.

"Ok, Mother. I will drive to town now and talk to Maria."

Vincent excitedly sped his way down to town and knocked on his sister's door. It was midday and he expected Maria would be home with the kids. He was surprised when Tony answered the door, holding a beer, wearing a white tank top and gym shorts.

"Skinny Vinny, what drags you into town? Heard you were running a big mansion up in the hills."

"Is Maria here?" Vinny asked, pointedly ignoring his question.

"Maria!" Tony screamed and walked back inside to sit on the couch.

The room was sweltering despite the box fan blowing noisily in the corner. Maria bounced down the steps wearing a loose fitting t-shirt and plaid pajama pants. Her hair was pulled back in a ponytail, accentuating her slim face and full red lips. Vincent could tell by the way her breasts bounced she was not wearing a bra. He tried to avoid staring at her nipples poking through the shirt.

"Hey Maria."

"Hi Vin, where's Mama?" she asked.

"Oh she is still at the office. I actually stopped by to ask you a question." Vincent said.

"Ok, what?"

Vincent didn't plan on doing this in front of Tony but proceeded to say, "Well another position, an assistant job, has become available and mama is going to take the job. So I need to backfill her position. I figured I would offer it to you first, you know, to make amends for bailing after Dad died."

Tony took a slug of his beer and said, "My woman doesn't need to work. I provide."

Maria almost laughed at that comment but she remained quiet and fiddled with her hands nervously not wanting to go against her husband. She loved her husband but he provided very little.

"Tony, it's a very high paying job. It pays $100k per year salary as well as benefits."

Judging by the astonished look on Tony's face, Mama hadn't told them how much she was making at the mansion cooking and cleaning.

"Oh, in that case, get to work honey," Tony said laughingly.

Maria agreed wholeheartedly after her husband consented. Vincent brought in some uniforms for his sister, gave her the written details of the position, and drove back to the mansion.

The next day, Vincent gave his sister a tour of the facility. Like he did with his mother, he took his time to show her the top floor, which contained his large bedroom, a working office, massive bathroom, and an expansive balcony providing 360 degree views of the grounds. He also showed her the security office, which he unlocked with a key. The monitors inside displayed video camera views of all the rooms and the pool area. He told Maria he kept the room locked but would occasionally open it for her to clean. Maria's work uniform accentuated her curves, she looked slim and fit, and was thrilled to be away from the kids performing light work in a beautiful air conditioned mansion. The job had seemed to revive her spirit and she gleefully bounced around the mansion dusting and cleaning windows.

After the tour, Vincent made a show of calling to his mother. "Mama, I need your assistance in the penthouse office please."

His mother wordlessly followed him up to the top floor. Vincent went into the bathroom, leaving his mother standing nervously in the bedroom area. Vincent took his time in the shower, savoring his mother's anxiety. Vincent finally exited the shower and observed his mother still standing in the same spot as before. He wore nothing except for a towel around his waist. He calmly walked to the bed and laid with his back against the backboard.