Matchmaking Trap
Chapter 1

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Ma/Ma, Consensual, Reluctant, Rape, BiSexual, Heterosexual, TransGender, Cheating, Incest, Mother, Son, InLaws, BDSM, DomSub, MaleDom, FemaleDom, Spanking, Rough, Humiliation, Sadistic, Torture, Swinging, Group Sex, Harem, Interracial, Oral Sex, Anal Sex, Sex Toys, Exhibitionism, Voyeurism, Size, Violent,

Desc: Incest Sex Story: Chapter 1 - Roberta and her son Chad make an interesting wager. When he loses the bet, he must pay with his body. Don't be sad for him, though; he's in for a very good time!

Roberta was a 43 year old bartender, working weekends to make enough to keep her house, after her husband's death. She was also incredibly gorgeous, with soft, sensual skin, that cried out for a massage. She kept her hair cut fairly short, but it was still a beautiful jet-black, and she managed to seem quite feminine, despite her tomboyish exterior.

She had loved being married, because, unlike many wives, she wanted sex every day, and made sure that she got it from her late hubby. She also knew about his affairs, as she had been his mistress during his first marriage, and she had simply not been able to give up his 9 inch cock. His sexual freedom was something that she had learned to accept as a necessary consequence of his higher libido.

Roberta had a grown-up son, named Chad, who was engaged to a woman named Deanna, a tall, slender brunette with a tendency to wear up-scale clothes. Chad and Deanna seemed your typical, run of the mill engaged couple, busy planning their wedding and working their jobs, while trying to fight off "cold feet".

What Roberta didn't tell her son and his bride-to-be was that she had trouble finding anyone new, because her deceased husband's cock had been so large, that it simply raised the bar for other guys, so to speak. She would fuck them, to try them out, but if they had small dicks, she would let them off easy, without much comment.

Chad and Deanna had made some attempts to set her up in the recent past, but their tastes were more conservative, all involving PC, pussy-whipped "Mama's boys". They tended to have small cocks, and were often reluctant to take the initiative in bed. None of them would have made the grade, and she hated to hurt her son's feelings about it.

One day, on a Monday night, as she sat with her son, talking about her loneliness, he kept insisting that she could find someone, if she just kept trying, and didn't give up. Roberta, however, kept noticing that he had potential to be tougher, like his Dad, if he could just break free of his college indoctrination.

They had filled his head with politically correct claptrap about sensitivity, until he was a hyper-sensitive pansy, as far as she was concerned. She also noticed his penis, which was about the same length and width of his father's phallus.

Gradually, as she continued to stare at his groin, she began realizing that this was her solution. She had the ideal lover right there in front of her, carrying his father's genes and, most importantly, his father's dick. She was willing to swing, but she only wanted to be permanent with a well-endowed, dominant sort of guy. This gave her an idea, and she immediately began to carry it out.

"Chad, if you are so sure that I can find a steady boyfriend, I challenge you to prove it! Try to make a match for me, and let me judge your success or failure, according to my standards! You'll have 6 months, or I get my prize! If you win, I will marry the man, but if I win, I get to use the largest cock that I know about, daily!"

"Alright, but whose cock is that, and what does that have to do with me?"

"I'm your Mom, so I've seen your dick a few times, and I wager that it's as long as your father's by now, making it the largest of which I am aware. That's your cock I was talking about, and you just agreed to bet it!"

"Mom, that's disgusting- incest? Besides, I'm committed to Deanna, and I won't cheat on her."

"You're also committed to this bet, which is more explicit a deal, and, therefore, more binding. If you really think you're right, it shouldn't be a problem, should it?"

"I guess not. You're dead serious about fucking me if I lose?"

"Yeah, because you need to loosen up a little, and I can help you there."

"Ok. Well, you have a deal, as I said."

Chad didn't really worry, except for the slim chance that he might lose, but he expected to win the bet, so he decided not to tell Deanna. He did seek her help trying to arrange dates for his Mom, but he didn't give her an idea as to the reason for his urgency.

They began planning in earnest, still clueless to the fact that his Mom knew for almost a certainty that she would win. Few men had cocks as large as her son's, and few, if any, of those men would be on her son's list. He was undermining his own side, and he didn't even know it.

Roberta was getting everything for her moment of seduction. The schedule had to be right, since she had to be making her move when Deanna was unlikely to catch them red-handed. She knew that her son would never tell his fiancee about something as "scandalous" as incest, so he would be there alone, ready to fall into her clutches when the time came to act.

Date followed date, sometimes ending in sex, sometimes not, depending on how PC the fool was, but, Roberta thought, the lucky ones at least got a lay out of it. The poor dupes who wanted to "wait" wouldn't even get that much, since she wouldn't give a 2nd date to a guy who didn't put out. Roberta, as she expected, found all of them lacking in the "dealbreaker" category- the size of their cocks. No man was equal to her son's penis, and she was hardly surprised about that.

Chad's confidence began to sink as the months wore on, and he was starting to have anxiety about the growing probability that he would be trapped into committing incest with his Mom, thereby cheating on Deanna. What choice would he have? He couldn't renege, because she was giving every a man a chance, even to the point of acting like a slut, which both disturbed, and surprisingly, on one level, aroused him. Could she really be that picky? What was wrong with her, if she didn't want these respectable men?

Deanna noticed his nervous behavior, but she passed it off as pre-wedding jitters. She thought that increasing the frequency of sex would solve it, but it didn't, and she was beginning to wonder if he was no longer sure about his interest in their upcoming marriage.

Even so, she made every effort to convince him that his sex life was not going to be over if they wed. He, of course, knew it wouldn't, but couldn't tell her that, and definitely couldn't tell her why.

Finally, just 2 months before the wedding, Roberta's time limit had elapsed, and Chad went to her house to find out if her last date had achieved a relationship. He was extremely scared as he rang the doorbell, and his Mom answered the door in a rather surprisingly conservative dress, not indicating what she had in mind yet.

"Well, Chad, it's been 6 months, and you know the deal. This last guy was nice, but, sorry, no dice! You haven't helped your cause, picking out these weak, groveling kind of fellows.

I'm sorry, but your tastes and mine are different, and that has cost you the bet. I have won, and I expect you to honor our agreement. I get your big manhood inside me every day, and you'll just to live with the fact that you're having an affair with your Mom."

"Mom, how can you do this? I am your son, and you are thinking about me in a sexual manner, as an object for your lust?"

"Chad, how can you seriously try to wiggle out of your promise? Besides, we are all objects of some kind to everyone. No chance, son, that I will let you out of this one! You need to keep your agreements, like your Dad and I taught you!"

"But, incest? Seriously, why do you want to fuck me?"

"I want your big cock, plain and simple, and I'm gonna get it, so just accept that fact! No one made you bet your cock on my love life, but you did, so live with it, son!"

"Alright, when and how are we doing to this? Deanna can't know, Mom, because it would crush her."

"Nice of you to care about your fiancee like that, but she'd survive that, I suspect. Anyway, I want you here and now! Take off your clothes!"

Chad quickly complied, as he was afraid that his Mom would divulge the bet to Deanna if he didn't. Once he was buck naked, Roberta looked at him lustfully, seeing that marvelous male sex organ free from his pants and underwear.

"Oh, wow, to think that I helped make this hot, young stud, who's about to fuck me! That thought really pleases me! I carried you in my womb, and now part of you is about to inseminate me. I love the irony of that fact!"

Roberta then dropped her dress, to reveal that she was not wearing any undies. She leered at him suggestively, motioning with her fingers for him to join her in the master bedroom. As she led her son into the bedroom, she took out some hand-cuffs, grabbed his hands, and slapped them on him. He was stunned, and looked at her to ask why she had bound him.

"I've got to keep you from escaping and breaking your contract, my boy! You're far too hesitant for me to trust you, aren't you?"

"Will this always be the case?"

"No, because you'll get used to fucking your mother, I'll make sure that you like it, and you'll soon be taking control in our sessions. I want that, you know? I want you to dominate me. Otherwise, however, I will dominate you, until you learn to accept my new dual role as your mother and your mistress! Now, lean over the bed!"

He did as she ordered, and she realized with some disappointment that he took after her in submissiveness. Okay, she thought, I'll have to dominate him, but I will just go out and find bossy men elsewhere. If Chad is getting it on with 2 or more ladies, and he is actually accepting my control over him, he will have to share me, too.

Roberta took out her late husband's belt, which she still kept to hurt herself, and started striking Chad with it, which caused him to welt and flinch in response.

She was angry at him for disappointing her with his submissive nature, but also smart enough to know that she had won him, and this came with the territory. Casual encounters with domineering men would have to suffice. Perhaps she could fuck them in front of him, and that would excite him a bit. Then, of course, she would give him sloppy seconds. He could then go running home to his "faithful" fiancee and her boring, Victorian morality.

She kept spanking him as she thought about this, and she could tell that he was enjoying it, which only confirmed his masochistic nature. Oh, why couldn't he have been a dom, just like his dad? she thought.

At last, when he was hard enough, she turned him over on his back, and swiftly mounted him, getting his cock deep inside her pussy for the 1st time. He was groaning with considerable pleasure, as he felt the confines of her cunt on his dick. She tightened up a bit for him, flexing her vaginal muscles to stiffen him further, and thereby increased the strain on his scrotum, until he just had to cum inside his mother's warm pussy.

"Oh, that's right, Chad, my son! Yes, cum for me, now! You can do that right, can't you? You may be a pathetic submissive, but at least your cock is great, and you have plenty of semen!

Oh, God, I'm very glad that I won this bet! Your ass is mine, and I'm going to use it! I own you, since you clearly want it that way, and I'm determined to keep you in compliance with our deal. Understand? You wanna be a slave, fine, but be Mommy's slave!"

"Yes, you own me- keep fucking me, Mom! I never knew this was so great! Thank you, Mom, I'm glad that I lost!"

"You're so great, I want to fuck you twice a day! Report to me during your lunch break, every day, and right after you clock out- is that clear? Whatever is left goes to your fiancee!"

At that, she grabbed a butt-plug, and without lubricating it, she shoved it up his rectum, making him squeal with the pain. She looked at him sternly, and then snickered as she thought of something.

"I'm going to have you keep that up your ass during the work days, and then you'll return it to me for washing at nights. You'll be getting your ass fucked alot, by all of my other sex partners, all of whom are men. That way, you'll be excited when I ride you, as your prostate will be stimulated by the cocks and the butt-plug. I will have the plug kept in your ass as I ride you, so you'll be under constant pressure, and will eventually have to cum inside me."

"Mom, I can't do guys! Ow, this hurts!"

"You will do guys, and if you want to stop hurting, seize the initiative and take control of me! Act like a man, and I'll treat you like one, with respect, but otherwise you're my boy-toy, for me to use as I wish! I am only dominating you, because you are willing to let me, so you have only yourself to blame here!

Oh, and as I implied, we'll always do it cowgirl-style, because you're a passive weakling instead of a real man, despite your manly cock. I'll even fuck your ass with a strap-on, now and then, if I wish it. By the way, masturbation is strictly forbidden in my house, so don't even think of touching yourself while you're here!"

"Ok, Mom, but please pull it out of me!"

"No! You're taking it, and I'm going to keep fucking you, while you take it, so get used to it!"

She rode him for what seemed like days, making him cum repeatedly, and draining his balls in the process. He was evidently loving it, so she knew that her decision to assume permanent control was a wise one, since he'd make a poor excuse for a master!

Finally, however, she released him, and made it clear to him that his duties would be specified to the letter the nights before, so he'd better pay attention. If he failed her, she would tell Deanna about the wager, and he knew what that would mean- the end of the engagement.

She had him by the balls, literally, but was partly so hard on him because she had really craved his dominance, and found him sadly lacking in it. Oh, well, maybe he'd give her another son, who would dominate her. She certainly hoped so.

For the rest of this story, you need to Log In or Register