Matchmaking Trap

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.

See part 2 for the rest of his enslavement by his Mom...