A Gamble for Mom

Introduction: Let the Games Begin

Eleven months separated Marc from his older brother Richard. As they grew older, the eleven-month difference became invisible. Maybe Richard was a little stronger and maybe Marc was a little smarter but that didn’t mean that Richard won all the battles of fists nor did Marc win all the battle of wits. That’s what made the competition between them interesting; neither knew who would win on any particular day.

And compete they did, about anything and everything. When viewed in hindsight, all the races, wrestling, boxing, and bets were a preparation for the contest that would alter one of their lives, the one for Annette.

Girls and then women became the focus when they were finishing high school. All they had to do was see a good-looking girl in the hall and one would say “Good to go?” and the response that followed only had to be a nod of the head. They both knew that the game was afoot. Which one would have her first?

“Good to go” was a sacred trust between the brothers. They could and did mislead, misrepresent, and mishandle, anyone and everyone else but once those words were uttered between them, the unspoken ground-rules went into effect.

Most of their lives had been spent with Annette and Joe, their mother and stepfather. At the time their real competition began, that relationship was about to end. “Fuck you” were the last words Annette had said directly to her second husband Joe. They weren’t entirely inappropriate.

Their marriage had taken place soon after the boy’s father died and in hindsight may have been a mistake, but it was the easier way out at the time. And although he never said it, Joe had left Annette for another woman. He was also trying to take all the assets with him as well. That part was still in the courts and Annette and Joe only spoke through intervening lawyers.

Annette had asked Lady Pauline about Joe a long time before the pain began to outweigh the pleasure. Lady Pauline, a neighbor who read the cards for Annette, had told her that the man in her life was going to give her nothing but trouble and that was the way Annette ended up feeling. Meanwhile, she worked to keep the boys in school, keep up her job, and keep up their home.

Annette was a sweet looking dark-haired woman with a good body that unlike most women her age, looked better out of her clothes than in them. She carried the few extra pounds that men like and women don’t, in the right places. Even though all the studies show that the opposite sex finds us more attractive than we do ourselves, Annette like most people, found it hard to believe.

She felt anything but attractive after Joe left. It didn’t matter how many people told her or much she knew in her head, that feeling that if only she was prettier or sexier…bothered her - along with the money problems and disintegrated marriage. Lady Pauline told her that her life was going to change. She wanted to believe in Lady Pauline…most of the time, that’s enough.

So call it synchronicity, confluence of events, or fate, but when the boys made their bet, their mother was at her most vulnerable. It started in the guise of a joke. Marc and Richard were bragging about how each could ‘make’ any girl of the other’s choosing. When Marc said, “I know someone you couldn’t even get to first with…she’s not with anybody and I know you say that she’s nice looking.”

Richard took the bait and said, “Twenty says I can.”

Marc laughed and said, “Okay Rich, good to go”

“Good to go” Richard said as he defiantly hit his brother’s fist with his own. “Who is it?”

“Mom”

“What?” After getting over his startle response, Richard started to laugh hard enough for the soda he was drinking to almost come out of his nose. “You crazy fuck.”

When Marc also stopped laughing he said, “Well you got to admit, that’s someone even pussy hound ‘Richard Don Juan’ can’t make…so pay up bud.”

The older brother hesitated for a moment and stared, “Who says I can’t…and you only said ‘get to first’ didn’t you?”

Marc couldn’t believe that his brother was serious until he looked at his wild eyes. Finally he said, “Get real…are you’re really going to try to…?”

“Damn right…and I’ll tell you what bro; fifty says I can get more than you can.”

Marc was almost jack lighted but by the time he regained his composure, his practically involuntary response was to stick out his fist and say, “Oh man…okay…good to go.” This was the first outward expression of a long undercurrent between them. They both found their mother attractive. They had talked about it when they were younger and at the stage where ‘catching a peek’ of their mother would lead to weeklong discussions of what one or both of them had seen.

Stories and Lotion

The plotting and planning began, and as with all of their bets, it had nothing to do with what would be won or the consequences; it was only about the winning. It never mattered how long it took or how much effort they had to exert, as long as they won.

Before the bet, what went on between Annette and her sons could best be characterized as ordinary. The usual familial squabbling and yelling mixed with generous doses of warmth and affection. After the bet, both boys started paying much more attention to their mother. They were more considerate, more attentive and more complimentary. Annette thought it was because her husband had left her and she was grateful for the kindness…she was hungry for it.

Richard was physical with her. He looked for any excuse to touch her. He hugged her more, he held her arms as he kissed her in greetings and then there was the lotion. Annette always took care of her skin and it seemed like she kept a bottle of lotion in every room. So one day as they were sitting in the kitchen Richard said, “Let me do that for you mom.” Annette was a bit surprised but she handed the bottle to her oldest son. He did her arms and legs and they both enjoyed the satiny stroking.

He only did it up to his mother’s knees and after a short time he handed her back the bottle. She thanked her son without noticing the beginnings of his hard-on as he rose and left the room. Without overdoing it, Richard found more and more opportunities to do it for longer and longer. Annette would put her legs on him as they sat on the couch and she would drowsily close her eyes as her son rubbed her. She took some notice when he moved up to her thighs with his gentle slippery fingers, but it felt too good to give it serious attention.

Richard’s hand on his mother didn’t escape Marc’s attention. He was thinking about telling Richard that the whole thing was crazy and they should give it up but he knew he would have to listen to Richard’s bragging and calling him a ‘pussy’ for months. He figured one of them would maybe get a feel and that would be the end of it. So he took a deep breath and let his compulsion to beat Richard overpower his reluctance. He set his mind on his mother and came up with his first plan, never thinking about the maze he was about to enter.

Knowing that his mother didn’t sleep well and often stayed up watching television late into the night, Marc thought of using it to his advantage. He also knew how much she enjoyed conversation. She could listen for hours to her sons telling her stories about the details of their day. She even enjoyed their competition because they were funny and good-natured even in their name-calling.

Marc started getting up in the middle of the night to sit with his mother. He told her that he also couldn’t sleep and at one point he asked her if she would like him to read her. Annette had always talked and joked openly about sex so when some of the stories her son read had erotic passages, she didn’t think much about it. After a few nights the stories he had printed pout from the Net got harder. Marc read to her about cousins who fell in love and had to fight their families to stay together; he read one about a brother and sister who survived together in war-torn Croatia and ultimately became lovers. She found the stories as stimulating as their talks about how far people will go when they’re in love.

Most nights Annette was as glad to be up as asleep because she knew Marc would read to her. He had a quiet gentle voice that lulled her while paradoxically the content stimulated her. At one point he suggested he read in her bedroom so that if she fell asleep she wouldn’t be troubled to get up. The first night in her bedroom he read her a story about a mother and son. It was graphic and Marc figured if he could get her to listen to a story about a mother having sex with her son he could win on that. He hadn’t even fantasized how far it would get.

Annette had her hands resting lightly between her legs under the sheet. As her son described the part where the mother first opens her legs and willingly accepts her son inside her, she became excited. As the story progressed the mother and son fell in love and in a scene where they lost control, her husband was in the next room. Annette was totally absorbed inside the story as the young man had sex with his mother.

With hardly a move she eased and pressed her fingers over her hooded clit. Her breathing changed and Marc began whispering. He began fitting in things that could have been from Annette’s life. She got hotter and started to moan. Her mind raced and she was lost in emotion and flowing juices. She whispered, “What’s her name…what’s her name?”

Marc brought his lips to his mother’s ear and said, “Annette.” His mother came. She came with a long moan that she tried to control when her awareness flashed but it was too late. When she returned her arched hips to the bed and realized that there was no way to cover up what had happened, she covered her face with her hands and started crying.

“Oh Marc…I’m so ashamed…I don’t know how I let that happen…God what you must think of me…”

“Mom, it was beautiful…beautiful to watch you come…all you did was feel good and that’s why I’m here with you…please don’t cry.” She stopped and looked up giving him a warm smile. He was moved.

“Thank you sweetheart,” she said before kissing him…too short to be a lover’s kiss and too long to be a mother’s. “Please don’t tell your brother what happened.”

“Of course not” he had said and of course the first thing he told Richard the next day was “I made mom come.”

Richard was stunned at his brother’s description but not enough not to say, “Well you know bro, it was mom who made herself come and not really you that did it…but I guess you do have a leg up on me…for the moment.”

That night Richard was determined to make something happen. His timing was perfect. Annette had a bad day at work and was still shook up from the incident with Marc. Shaken and stimulated, she could think of nothing but sex all day…her pent-up emotions ached for release.

Richards’s leg rub that evening reached Annette’s inner thigh before she knew it. Richard talked as he massaged making up a story about how lonely he was and how he could never find someone to be with…someone as sweet as she was. In her rational head Annette knew better but her son was appealing to the motherly part of her…the part that wanted to protect and take care of him. So when he ended his sob story with a plaintive kiss, her lips parted at the insistence of her son’s lips and her legs parted at the insistence of her son’s hands.

He asked her just to let him kiss her and she let him. She let him kiss her lips her neck and her breasts. She let him kiss her belly and when he raised her skirt she let her son kiss her pussy over her panties. All the while she wrestled with her confusion. Assuming it was all her doing with both of them, she wondered why she was seducing her own sons.

She wondered as he kissed, she wondered as his mouth found her clit and then she wondered no more. She came. She came with his lips and tongue pressing and easing on the nub over her panties much as she had done with her fingers in the presence of her younger son. There were two distinct wet spots on the filmy material: one where his mouth had been and the other where her pussy had been. Richard also told her that he wouldn’t tell Marc.

Lady Pauline had told Annette that her life would change. It sure was changing but could this have been what she meant? Annette went for a reading and without revealing what was going on, was glad when Pauline told her that she was on the path that would bring her and her family happiness. Annette felt her money was well spent.

Competition Stiffens

The first one to gain entry into his mother’s pussy was Richard. Only a few days later he played up his loneliness card. He went into her room deep into the night. He said, “Mom, I didn’t want to bother you but I needed to talk to someone.”

Her instincts kicked in. “Honey, you can always talk to me; you know that…don’t you?”

“I do mom but it’s hard to say…can I hold you for just for a while…I’m going crazy…do you know what that’s like…just to need someone… so badly…?” She knew and he knew that she did. So Annette opened her arms to her son and after affectionate kisses on her neck led to hungry ones on her lips, she could feel the hard length of her son’s cock on her thigh.

Her oldest did the all the things he had learned to induce women to yield to him. The fingers and hands, the lips and mouth did the convincing. He didn’t have to go far because his mother was ready to give in.

Mother and son were soon naked with flesh upon flesh. The first entry of her son’s full cock into her wet opening caused an explosive “OH God…” to release from Annette’s lips. It was filled with anxiety, relief and unique excitement. The wall in front of the ultimate taboo had been breached. Her son’s cock was moving inside her pussy…pleasuring him…pleasuring her. She felt the length of him going in and out as she practically creamed all over the long shaft.

His hands were all over her, pushing up at her breasts and reaching under for her ass. She could hardly breathe as her son fucked her. Neither of them could hold on for long as the fervor of the mother-son union increased. He gave it to her steadily without varying the pace and without a word. It wasn’t that long after Richard started sending semen into his mother’s pussy that she thought she was about to come, but he finished before she could. It had felt good and she didn’t want him to feel bad so she held him and didn’t betray the fact that she hadn’t come.

When Richard told Marc that he had, as he put it, “Dipped his candle,” Marc didn’t want to believe it. He was stupefied. His brother had actually had sex with their mother? She had spread her legs…and he had been in her pussy…? The thoughts ran around his head for days until they settled in a place where he finally came to believe them. He was in a way glad of his brother’s success because it meant that maybe he could have her too.

One week later Marc made love to his mother. She hadn’t come to terms with the sexual encounter with Richard, and Marc was the one she talked to. Without actually telling him what happened, Annette tried to sort out her feelings with him. She went on about how people had responsibility not to always give in to their urges. She said, “I don’t know what kind of mother…or person I am…I do things I shouldn’t…I…”

“Mom…” He knew exactly what she had done because Richard had given him the blow by blow. “You’re a wonderful mother…and a special person…” He was jealous, angry, desirous and too many words to contain in his head. “You’re full of love and you do things out of kindness…and I love you for it.” Whatever else he was feeling, he meant every word. The game was starting to bother him. “You don’t have anything to feel guilty about…maybe other’s do.”

Annette thought that Marc was talking about reading the erotic stories to her and said, “No, no baby…you didn’t do anything.” She kissed his downcast face and he gently kissed her forehead and eyes. He wanted his mother and it had nothing to do with any bet. He wanted his mother.

They kissed for a long time and as each kiss became more passionate they both began anticipating the same moment…the moment of penetration...when a son would be inside his mother. Marc began taking Annette’s clothes off and even though she was offering no resistance he hesitated. “Can I mom?” He asked.

“Yes baby.” She was beyond contemplating that she was about to make love to the second of her sons. She only knew that she wanted to. When mother and son were naked they held each other in a loving embrace. They did what only humans do…waited for the moment of entry to make it sweeter... put it off until they ached…kissing…touching. They stood and explored each other.

What first got Marc’s attention were his mother’s nipples. They were a dark hue of reddish brown and quite large. He took one of the full cones in his hand and sucked on the end; his tongue circled the hardening tip. His mother reached down and massaged the cock that seemed alive in her hands. She was not expecting the pre-cum that wet her palm as she caressed over the crown.

Annette hesitated when she realized how far they had gone but when her son put his finger in her pussy and her own wetness appeared she let it carry her. They kissed again and Marc’s hand rested for a moment below the small of her back and then roamed over the globe of her ass. One of his fingers played at her pucker without penetrating but it sent a shiver through her belly and an urge she hadn’t experienced before.

Marc took her hand and led her to the bed. He sat cross-legged and patted the spot where she could sit facing him. He wanted to slow it down because he had almost come in her hand as she stroked and massaged him. He told his mother that he loved her breasts and showed her by fondling and sucking until the nipples swelled and became engorged. He put his hand on his mother’s pussy and gently massaged over the lips and clit until she moaned and could no longer stand the anticipation.

Annette mounted her son easing the big cock into her wet center. When she had it all in her, she hugged him and smiled a long “Ahhhh…” pressing her breasts into his chest and wrapping her legs around his back. She began a circular motion with her hips as she held him and spoke in his ear. “It’s so good to have you in me like this baby…making love to your momma…”

“Yes mom, that’s what I want to do…love you and make love to you.” They kissed as the grinding continued. Marc put his hands under the meaty globes of his mother’s ass as she started to rise and fall on the thick pole that filled her pussy. Her nerve endings fired as she felt the engorged cock of her son satisfying the emptiness, satisfying the ache she had felt for too long. The passion she felt for her son at that moment was unexpected.

Marc knew from experience that he would have to turn her and mount her if he wanted to control when he came but he had let her go on for too long. She was rapidly raising and lowering herself on him and it felt too good to stop. He was lost in the feelings when he told her, “Mom I’m gonna come…I’m gonna come.” He didn’t have to tell her.

Annette felt the first eruption of her son into her pussy before he said anything. She answered his releases with her own and got louder with each “Yes” and she clenched her pussy with each motion, using her son’s cock to bring herself off. She liked the thought and feeling of having Marc’s cum inside her. She put her hand where they joined to feel their wet union. When they finished she held his face and put her nose on his and said with a smile, “Oh God that was good, wasn’t it baby?”

Marc’s answer was a long kiss filled with, “Mmmmm…”

Richard and Marc ‘Do a Number’ on Annette

Having sex with their mother became the focus for the two brothers but Annette still limited it. Had it been left to them, she never would have gotten out of bed. But the inability to assess what was really going on, not only with herself, but any two sides of the triangle, led her to try and keep the sexual encounters at a minimum. She didn’t always succeed. Lady Pauline wasn’t much help. When Annette asked her advisor if she should feel guilty about what she was doing, Lady Pauline had said, “Well…yes and no." But if you follow my instructions, everything is going to work out.”