Pleasing Mama

"Come, Mama, take a seat," he said as he patted the bed.

Mama complied and walked over slowly, sitting next to her son. She sported an angry look on her face and finally met his her son's gaze. "So you intend to actually go forward with this?"

"Remember Mama, you offered and we made an arrangement."

With that, Vincent opened the towel revealing his cock and balls to his mother.

Mama couldn't hide her shock at what she saw. Her son's cock was soft, yet it was five inches long, veiny, and laid heavily over the largest set of balls she had ever seen. Vincent reveled in her silence and stunned look.

Finally she mumbled, "Perhaps a man after all."

"Let's go Mama, I am ready."

His mother took a deep breath and defiantly stared him in the eyes as she wrapped her small hand around his dick and stroked his shaft slowly. Vincent hardened in her hand and she adjusted her grip as his cock grew and grew until it was a full ten inches in length. Mama's eyes widened in dismay as the cock in her hand seemed like it would never stop growing. The length and thickness were difficult for her to comprehend. She never imagined a cock could be so large, that it belonged to her cowardly son was even more amazing.

She pulled and pulled on his length, all the while she stared at Vincent until he finally broke eye contact and laid his head back closing his eyes. He let out a soft moan. He wouldn't hold out long, his mother firmly stroking his cock while his sister cleaned two floors below was just too much for him to handle. He ogled his mom's cleavage and the rhythmic way it moved in concert with her pulls. Mama was focusing her strokes on the top of his cock, stimulating his shaft and head at the same time. He finally felt that familiar stirring in his balls and he released ribbons of cum skyward as his mother smiled at how quickly he had erupted. Vincent moaned as she continued to pull on his cock until every last drop was deposited on the bed, his stomach, and her fingers.

"Easiest money I ever made. I will go read by the pool then go home and check on the grandchildren," his mother said as she got up, grabbed some tissue from the nightstand, and walked from the room, laughing to herself.

The next two sessions went in a similar fashion, but by the third session Vincent had become used to the touch of his mother's hand on his cock. His mother pulled and pulled until her arm grew tired. She alternated hands as the minutes passed and Vincent still had not shot his load. She tried a twisting motion using both hands and then another where she massaged his balls while stroking his length to no avail. She was visibly tired and looked frustrated.

"Take off your shirt, Mama, I think that would help," Vincent said confidently.

Mama was growing weary. Despite how good her son's large cock felt in her hands, she knew it was wrong. She knew he was trying to get back at her for some perceived wrong from his childhood. What son wanted to see his mother's tits? It was perverse.

"Fine, I need to get back to my reading," Mama said defiantly as she reached her hands into the deep v-neck of her shirt and pulled out her D-cup breasts.

Vincent's heart beat faster at the sight of his mother's tits. He had only seen the breasts of the few girls he had met in college but Mama's were by far the nicest tits he had ever seen in person. They were perfectly symmetrical, with large dark areolas. He imagined how her hard nipples would feel in his mouth. His mother pulled on his shaft, twisting softly on his mushroom head with each pump. Within seconds he was shooting his load in the air, his mother careful to keep his cum angled away from her tits and face. Mama quickly put her tits back in her shirt and went back down to the pool to continue her reading.

Maria was still clueless, yet curious, as to what the assistant job duties were and was jealous that her mother sat around reading all day by the pool while Maria prepared food, cleaned, watered plants, and performed other menial tasks. When she asked her mother what she did in those meetings, she told her, "Just some paperwork and other stuff."

Vincent came down the stairs a few minutes later and sat on the couch with his laptop.

"Vin, why does Mama get to sit around all day while I work. Can you get me one of these assistant jobs? I wouldn't mind getting paid to lay by the pool all day."

Vincent was joyous that his sister had brought up the topic, it would make the next phase of his plan easier.

"Oh, Maria, Mama is performing some very important tasks. You see my boss is a new age guru and has unconventional methods on relieving stress and maximizing potential. I am not sure you would be interested but I will reach out to my boss and see if it is in the budget. Things are progressing well lately, so he may go for it."

Maria smiled broadly at his answer, "Thank you, let me know. Mama mentioned it even pays more."

"Yes, it pays significantly more, like I said, I will ask," Vincent said with a devious smile.

A few days later, Vincent brought Mama upstairs for another session. Mama pulled her tits from her shirt again before she even touched Vincent's cock. She figured they would end up out anyway and she could save some time. Vincent wanted to push his mother to do more, so he had jerked off that morning thinking of her breasts. Mama would have her work cut out for her trying to make him cum again. To Mama's surprise and Vincent's chagrin, no matter how Mama jerked him off, she could not make Vincent cum. Vincent once again offered a solution.

"Mama, use your mouth please, I don't have all day," Vincent said coyly.

Mama looked at her son's massive veiny cock and wondered how she would even get that in her mouth. Her dead husband's cock wasn't nearly this size and she had stopped giving him blowjobs over 15 years ago. She was actually beginning to enjoy the sessions with her son. Having someone look at her as a sex object, even if it was her son, brought her back to her youth and made her feel like a woman again. The mansion, the pool, and the luxurious bedroom also made her feel like she was finally out of that stupid town and living in one of her romance novels.

Her anger at her son leaving her in a lurch was also subsiding. It was turning out that he was not a loser like his father and he had returned to help the family, even if his methods were odd and perverted. She decided then and there that she would suck the big cock in her hands and try to enjoy it. She would pretend it was the cock of one of the heroes in her romance novels.

Vincent watched in dismay as his mother dipped her head and began licking the head of his cock. She wrapped her red lips around his dick, engulfing the head of his cock and an inch of shaft into her mouth. Vincent pulled her hair up and held it in a bunch with one hand. He guided her head gently up and down. Her tits hung enticingly and Vincent hesitantly reached out and squeezed them with his free hand. Mama gave him a sideways look from the corner of her eye but quickly returned to sucking her son.

Mama sucked and pulled until she felt Vincent lift his hips off the bed. She pulled her face away despite Vincent softly trying to push her back down. Vincent came in spurts, shooting high into the air and back down onto his stomach and chest, while moaning and squeezing his mother's breast roughly. Mama continued to pull on Vincent's cock until he softened and the last bits of cum dribbled out onto her fingers. Mama then fixed herself up and went back to the pool while Vincent showered and made his way to the ground floor where Maria once again asked about the assistant position.

"I have reached out for budget approval, I expect an answer next week," Vincent replied cheerfully.

Things were going swimmingly and Vincent was in a great mood. His plan was working and the following week he would unleash the next phase. He planned to accelerate things with Mama and enlighten his sister on the true duties of an assistant.

Monday came and Mama idled by the pool while Maria labored inside. Vincent unlocked the security room and asked Maria to dust, mop, and clean the area as well as the twelve security screens which hung on the wall displaying the live cameras. Vincent then went to the pool and summoned Mama for another session.

Mama joined Vincent in the penthouse bedroom and sat next to a toweled Vincent on the bed, pulling out her breasts. Mama jerked her son vigorously until he was fully erect and then went straight to sucking his cock. She would never tell Vincent, but she had enjoyed the last session tremendously. She looked forward to having his big cock in her hands and mouth again. Vincent stayed cognizant of the hidden camera positions in the room and maneuvered himself appropriately for the best view. One camera was positioned on the ceiling behind him, the other from the balcony entrance on the left. He was confident both would provide a great view if his sister was watching as he hoped and suspected. He was happy that his mother had blissfully started sucking his cock without encouragement but Vincent wanted much more than that today.

"Mama, I need you to lay down."

Mama looked at him with a mouthful of cock but didn't respond. She continued sucking.

"Mama. please. I need you to lay down," Vincent said as he scooted over on the bed giving his mother room to lay down.

Mama was confused and worried as to what he was up to, but complied. She laid flat on the bed with her head up on the pillows. Her tits were propped up nicely and framed by her bra and shirt. Vincent straddled his mother, placing his long heavy cock between her breasts. He roughly pushed her tits together and pumped his cock in between her soft skin. For the first time during their sessions, Mama didn't feel in control. Vincent seemed determined to take what he wanted today and she was both nervous and excited as to what would happen next.

Vincent abruptly stopped fucking his mother's breasts, knelt between her legs, and grabbed the lip of her yoga pants with both hands to pull them down. Mama reflexively grabbed his hands and stopped him.

"Mama, I want to see your pussy. I need to, if I am going to cum," Vincent pleaded.

Mama released her grip, turning her head and biting her lip as Vincent pulled off her pants and her underwear. Vincent gazed in lust at his mother's hairy pussy. She had not shaved in ages and it grew wildly. Her labia looked small and enticing to Vincent. He ran his finger across her slit and felt her slickness. His mother may be looking away from him but her body wanted his cock. Vincent spread his knees wide between Mama's thighs, swiped the head of his cock up and down her wet clit, and pushed his mushroom head against the entrance to her pussy. Mama continued to look away, the back of her hand over her mouth as if fainting.

Vincent pushed and pushed until he finally slid a few inches of cock into his mother. Mama gasped. Vincent reared back and pushed further into his gasping mother, he repeated this over and over until he was buried inside her, his hips touching hers. Mama couldn't believe her son was all the way inside her, fucking her. His cock felt massive and he was stretching her like never before. Vincent could only think of one word as he drove his cock as hard as he could into his mother: 'weakling'. Did his mother still think he was a weakling as she writhed beneath him, struggling to take his big dick? Did a weakling fuck like this?

His mother grunted at the bottom of each downstroke. A guttural sound that was a mix of pleasure and pain. Vincent The Weakling pumped away at his mother's tight pussy as her breasts bounced wildly up and down; occasionally bumping her chin.

Her body tightened beneath him and she grabbed her son's arms which were planted on the mattress on either side of her chest, pleasure had overtaken the pain and she was cumming intensely all over her son's cock. Mama moaned and moaned as her face flushed during her orgasm. Vincent did not lessen his pace, he needed to focus on the feelings of misery and self doubt his mother had instilled in him over the years. He would fuck her into oblivion, whenever she thought of her son, he wanted her to think of his sexual prowess and stamina.

Mama still held onto her son's arms, she had tilted her head up to watch his big cock slide in and out of her hairy pussy. Her orgasm had been mind blowing. She honestly thought she might pass out. Her son was hammering away at her pussy like a machine, she never imagined she could be fucked so thoroughly and filled so completely. Vincent hadn't slowed after she came, he was still fucking her forcefully, his big dick touching parts of her she didn't know existed. She thought Vincent's fathers cock was large but it was nothing compared to the monster dick plowing inside her now. His length felt so good in her after the initial pain had subsided, so amazing, that she knew she would fuck Vincent any time he asked, money or not.

Vincent was sweating, his arms felt shaky from holding his weight above his mother's mostly naked body. He felt like he had been going for hours but knew it could only be ten minutes or so. He tried not to think of his sister who was hopefully watching the video in the security room below. If he thought too much about that, he would surely cum. He needed to focus on his anger and prove to his mother he was strong, not a weakling. His abs strained, his arms were wavering, yet he thrust into his mother over and over again until she succumbed again to her pleasure.

Mama muttered in Italian and then moaned loudly, "Oh lord, oh lord, oh lord, such a big dick. Oh my lord, Vincent!."

Vincent could hold it no longer, he pulled his cock from his mother's pussy and shot streams of hot cum across her belly and into her pubic hair. He sprayed it liberally across her wet pussy as well. He savored the sight of his mother covered in sweat and cum, completely worn out from his fucking. He climbed off of her wordlessly and headed to the shower.

Maria sat stunned in front of the security monitors. Her mind raced. Mama's assistant duties apparently included fucking Vincent. Is this what she did all those times they were going to meetings? It was very disturbing, possibly the most disturbing thing she had ever witnessed. However, it had also been one of the hottest things she had ever seen. Her little brother's cock was absolutely massive and he had fucked Mama until she had cum. Twice! Mama looked like she was in heaven. Maria couldn't help but think what it would be liked to get fucked like that. Her husband's cock was half the size of Vin's and he rarely lasted long enough for Maria to cum even once.

Maria suddenly felt a wave of panic as she remembered she had asked Vin for the same job as Mama. She couldn't fuck her brother, could she? She promised herself she wouldn't bring the job up again to Vin. She quickly closed the door and went to the kitchen, pretending to look busy. Vincent stepped from the shower and grabbed his phone. He swiftly loaded his cameras from the cloud and looked at the video from the hidden camera in the security room. Yes, his sister had watched the whole thing. Her expression was a mix of horror and intrigue. He decided he would wait, give her time to think about what she had seen, and approach her tomorrow.

Maria barely slept that night. Visions of Mama writhing in ecstasy under her brother crept into her brain every time she closed her eyes. His giant dick, the way he came all over her, it was so wrong and so erotic. Eventually she slept fitfully still not sure if she was turned on or disgusted.

The following day, Vincent approached Maria while she was cleaning windows in the dayroom.

"I have spoken to my boss, he is exceedingly happy with my results and has authorized a second assistant."

Maria didn't look at her brother and quickly said, "I think I will keep this job. I am enjoying the work."

Vincent stepped closer and said, "I haven't told you the best part, the pay has more than tripled. Ten thousand dollars per week with a three month signing bonus, but you don't have to answer now. The stress relief duties only occur a couple of times a week so the rest of the time is yours to do as you wish. Please talk to Tony first and let me know. He must be made aware of what the job entails and also approve. I wouldn't want any problems. As a matter of fact, have Tony and the kids come up to the mansion tomorrow. I'll have it catered, it will be fun."

Maria avoided looking at her brother and responded, "Sounds fun, the kids will love it. Thank you."

Maria juggled her thoughts as she drove home. Did she dare approach her husband with this offer? She hadn't said anything to him or Mama about what she witnessed. Mama seemed to be happy last night at dinner, humming to herself as she helped set out the plates for dinner. A far cry from her normal angry and overbearing personality. Could she do sexual things with her own brother? Many women did a lot more with strangers for far less money and the amount of money Vin was proposing was life changing. She could pay off her mortgage in only a few months time and start getting her family's financial position in order, but what would she tell Tony? He would lose his mind and probably want to hurt Vincent. She was worried that Vincent would say something to Tony tomorrow so she must broach the topic tonight.

After dinner, Maria finally had some time alone with Tony as they went for a walk down to the Lackawana River, a spot they used to sit as teenagers and talk about how great their future would be and all the amazing things they would do together. Most things hadn't panned out as they hoped. Tony had taken to drinking after the union jobs dried up in the area. He now worked as an independent contractor but rarely worked and when he did seemed to underbid the jobs so there was little profit. A cool wind blew across the river, lights twinkled in the darkness, frogs and cicadas buzzed. Tony cracked one of the beers he had brought and settled down on a log.

Maria broke the silence, "So Vin said there is an opening for a very special job at the mansion, it pays a crazy amount of money, and Vin has offered it to me first."

"Nice, about time that loser did something that benefits the family. How much dough are we talking about here?" Tony asked.

"Ten thousand a week plus a hundred and twenty thousand signing bonus," Maria said meekly.

Tony choked on his beer and lurched to his feet, "What? Are you fucking kidding? Take it. Think of all the things we could do. Holy shit, that is nuts. Hurry up and take it before it's gone."

Maria threw up her hands, "It's not a simple job. It requires doing certain things."

"Who cares? You'll figure it out, fake it till you make it, right?" Tony said excitedly.

Maria dropped her head and whispered, "Sexual type things."

"Wait what? What does that even mean?" Tony questioned.

"It means doing things with my brother to relieve his stress, apparently his boss is some new age weirdo that believes a man can only perform in his job if his mind is clear of impure thoughts, or something. I don't know."

"So your brother wants you to be his whore for money?" Tony asked incredulously.

"I guess, in simple terms. A couple of times a week, I would assist with his release of impure thoughts," Maria said quietly.

"Hold on, is this what your Mother is doing right now?"

"No no, Mama is doing office work," she lied, "This job pays much more than that."

Tony was pacing, "Holy shit, Skinny Vinny. That little prick is using our financial position to try and get in his sister's pants. I always knew that little freak wanted you to be more than his sister."

"It's so much money, Tony. What do we do?"

Tony was still pacing rapidly back and forth. Finally he said, "You take the job, we get the bonus. You put him off for as long as possible. Tell him you have a headache, period, whatever. You keep away from the perv and we collect as many paychecks as possible until he fires you."