Dillon's Mommy Ch. 04

Note from the Author:

This is a story of female domination and harsh humiliation from a mother to her submissive sissy son. I put it in the fetish section because the incest crowd is pretty harsh when it's not just family members fucking each other. This is fantasy, so please no comments about what a fucking cunt the main character is, or what a fucking pathetic pussy her son is. I wrote this chapter for a reader who begged me to give him more of Grace. I hope he and you that like that kind of thing enjoy it. If humiliation and Femdom are not your thing, please move on. You have been warned.

Goamz86

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It had been almost two weeks that Grace had been manipulating both Kendal and Levi. She was keeping them apart by blackmailing Levi with her pussy to deny Kendal, and counseling Kendal on how to deal with Levi's behavior. She had Kendal convinced that Levi was fucking someone else and she had degraded her confidence while doing it by subtly suggesting that the woman Levi was fucking was somehow superior to Kendal.

She repeatedly suggested that Kendal needed a confidence boost, and she knew just how to do it. Grace reminded Kendal all the time how much Dillon worshiped the ground Kendal walked on and how, given the chance, he would do anything to get another chance with her. Grace told her she just needed to confide in him a little and he would reciprocate with an abundance of affection. This would serve another purpose for Grace as well, keeping Kendal's attention off Levi, leaving him to Grace's grip. Kendal continued to rebuff Grace's ideas about Dillon. Grace assured her that she would not have to harbor any real feelings for him, it was just a way to boost her confidence. Grace promised that when she was feeling better about herself, the two of them would have a great time one night crushing Dillon's hope by humiliating the shit out of him. It would be a winning proposition for all. Grace really was becoming a sadistic bitch where Dillon was concerned.

Kendal agreed and the two of them set out on their separate paths. Of course, Kendal didn't understand Grace's path was to fuck the balls off her boyfriend while her attention was focused somewhere else.

For another two weeks, Grace fucked Levi silly behind Kendal's back, while Kendal lead Dillon on, like a love-struck teen. She gave him just enough hope to make him willing to do anything and everything for her, and she didn't even have to ask. One day she came home from work to find all her laundry done and folded on her bed, another day he detailed her car as she slept 'til noon after working late the night before. He even polished all her heels and boots after she only hinted one night that her "nice" shoes were looking pretty "scuffed" while they sat on her bed talking about how she was still hurting from Levi's treatment of her. Dillon was a pathetic lost cause according to Kendal, but it did really feel good to have someone dote over her. Levi would never do any of the things Dillon was willing to do, let alone just for a little of Kendal's attention. She never even gave Dillon a kiss. She did drop tiny little hints that she missed being treated nicely like Dillon had when they were dating.

Soon Kendal grew bored with Dillon, and she was so very curious what Grace's plan was to humiliate him. She had absolutely no respect for him and felt that if he was this pathetic, he deserved whatever Grace had planned. She was looking forward to it now and she was ready for it to happen. She queried Grace about her intentions, but Grace wouldn't give her the details, only saying she would have to fuck Dillon as part of the game. Kendal balked at that, but Grace assured her that his little wee wee would be covered with a condom and that he would get absolutely no enjoyment from it. Confused, Kendal finally relented, thinking Grace must surely have a great plan and that she would enjoy every second of it.

The day came and Grace told Kendal to be ready that night. At dinner, Grace secretly put Viagra in Dillon's drink. After Dillon cleaned the dishes, Grace invited him to the bedroom for some fun. She told him she wanted to play a game which involved tying him to a chair. She told him if he cooperated, she would make sure this would be the night he got to fuck Kendal. With that incentive, he of course gave no resistance.

Grace was dressed in her normal evening clothes. A pair of silk panties, with matching silk camisole and a long silk robe. As she tied Dillon to the chair, his cock filled rapidly with blood as he thought of all the possibilities this night could bring, especially fucking Kendal. It also helped that Grace mercilessly teased him by rubbing his thighs as she tied his legs to the chair. She brushed over his nipples as she tied his hands behind the back of the chair. Then, as she nibbled his earlobe, she told him how she was going to enjoy watching him fuck Kendal tonight.

By this time, Dillon was so hard that there was no keeping his throbbing penis from pressing hard against the spikes in his cage. The pain, combined with his extreme arousal, was almost too much to take. Then Grace straddled him, while facing him. She teased him even more, by grinding on his caged penis and shaking her massive tits an inch from his face. Her scent, and her dominance, only aroused him more.

"Would you like Mommy to take off this cruel, cruel cock cage buttercup?"

Dillon silently, but frantically nodded his head. She walked over to the nightstand and retrieved the key. She unlocked his cock and as she pulled it off, the blood rushed in even more. His youth, along with the Viagra, had his cock as rigid as a lead pipe.

"Oh my, someone is very, very aroused. Is mommy making you hard like that, or is it the thought of fucking your dear sweet Kendal, Dilly?" She teased, knowing what his answer would be, while grinding on his lap, with his penis sticking up between his belly and her panty covered pussy.

"You, Mommy, you!" He replied desperately.

"Would you like mommy to make you come with her hands?" she asked, pressing his face between her silk covered tits.

"YES, PLEEEEEEEEEEASE, MOMMY?" came his muffled plea.

Now, here is where the cruel, sadistic Grace took over. She grabbed a pair of rubber gloves she has stashed away, and put them on. Then she squeezed some cream from a tube into her hands and began to slowly stroke Dillon's throbbing penis.

"Oh my goodness that feels good." Dillon thought to himself. The lube and her hands, even with the gloves on felt soooooo good. He tried desperately to keep from coming. He was sure he was going to blow. Grace just kept slowly stroking and stroking and stroking, never speeding up, keeping him on the edge. After a bit, Dillon's cock began to feel very very odd. He could still feel him mom tugging on it, but the sliding feel against his sensitive skin seemed to have disappeared. Within a few minutes after noticing this, he couldn't feel her hands on his still throbbing member at all, just the feel of his mom tugging his little cock. He didn't know what to think when his mom enlightened him that what he thought was lube, was really numbing cream. She rubbed and rubbed for quite a while ensuring that it would not wear off anytime soon. She removed the gloves and discarded them in the bathroom trash. Then, she peeled open two condoms and rolled them one over the other onto his still rock hard penis. Just as Grace was finishing with the condoms, the sound of the front door closing was heard.

"Grace?" called Kendal

"In here."

Dillon was mortified. He didn't want Kendal to see him like this. His mom told him he was going to fuck Kendal tonight. She would never do that if she saw him like this. It didn't take long to confirm Dillon's fears.

A moment later Kendal appeared in the master bedroom. She immediately giggled at Dillon's situation. "You were right. He is the most pathetic little fuck I have ever met. He will do anything you tell him to do, won't he?" Kendal asked Grace.

"Oh sweetheart you have no idea." Grace retorted. "Now, go get ready like we discussed."

Kendal hurried off, giggling all the way.

Grace straddled Dillon, facing him, nestled up tightly to him and whispered villainously into Dillon's ear, "Now be a good boy, and mommy's promise to fuck Kendal will come true." Then she rubbed her massive tits in his face and slowly moved down his body until she was kneeling in front of him. She pulled her tits out of her cami and squeezed them around Dillon's throbbing little penis and fucked her cleavage with his cock for a few seconds. His cock was so fucking hard he could feel each beat of his heart pulsing the blood through it. Grace pulled it down with one finger between his thighs until it was touching the seat of the chair and let it go. Like a catapult that had been wound and then released, Dillon's cock sprang back and smacked his stomach. He winced a bit out of instinct, since there was no feeling in it, as it came to rest sticking straight up to the sky.

Kendal returned wearing the sexiest ensemble of lingerie Dillon had ever seen on her. A royal purple spaghetti strap teddy with black lace trim that hugged her body and displayed her breast. It had garter straps that were holding up black seamed silk stockings and she had a pair of black spiked "fuck me" heels on. There were no panties and her freshly waxed pussy was on display. Dillon's cock swelled even more, if that was possible. The combo of not coming for quite some time, his young hormones and the Viagra was almost too much for his cock to handle.

"You look fantastic, honey." Grace told her.

"Well thank you." Kendal replied.

"Doesn't she look so sexy Dilly?"

"Yes Mommy." Dillon replied.

"Mommy, that kills me every time." Kendal chuckled. "You truly are the most pitiful fuck I have ever met."

"Climb on." Grace told Kendal. "Show my snookums here what he will never get to have after this night."

Kendal mounted Dillon's raging reed by straddling him facing away from him and toward Grace who was now on the bed lying against some pillows propped on the headboard.

"This is the most pitiful cock I've ever felt." Kendal told Grace. "Now I know for sure I didn't miss anything when I didn't fuck him while we were dating........Well, if you want to call it dating."

The humiliation only turned Dillon on more. Grace joined the humiliation party.

"Kendal, honey, Dilly has been reporting to me the last couple weeks that you two have been close and he thought you might be considering getting back together with him. Is that true?" She asked, now rubbing her mature pussy through her silk panties.

"Me........, date this fuck.........., with this penis? Are you fuckin kidding me? Not in a million years. I can't even feel this thing in my pussy and I haven't gotten any dick in a month." She scoffed.

Dillon was crushed. Humiliating him about his cock size was one thing, but this kind, was different. His cock even began to soften a bit. He couldn't feel a thing from the fucking and his emotions kept him from being turned on.

Kendal could feel him getting soft and said something to Grace.

"His little thing is even starting to get soft now. He's fucking a hot bitch like me and he can't even keep that tiny little thing hard. What a worthless piece of shit! We can't have that now can we Grace?"

"How can we use his little wee wee if it's getting soft?" Grace teased, "Dilly, Look at mommy."

Dillon craned his neck to the side so he could see around Kendal. Grace slowly peeled her panties off, exposing her juicy, mature pussy. She rubbed the thick loose lips, then inserted two fingers inside. She methodically fingered herself for a few moments, then spread her opening wide.

"That works." Kendal informed Grace as she felt him stiffening up, and the teasing continued.

Dillon immediately forgot his shame as the two sexy vixens continued to tease him and humiliate him for the next two hours. They would switch off climbing aboard his numb stiff cock riding it as they told him how useless it was and that a real man would never let two women take advantage of him like this. He was so turned on, that his cock stayed hard the whole time. Regardless of the fact that he could feel nothing from the friction from the fucking.

Grace teased him with her tits, standing and leaning over so he could suck them as Kendal abused his little penis, riding it roughly. Grace also relentlessly teased his nipples as she and Kendal rode him. The stimulation kept him rock hard and on edge the whole time, but didn't allow him to reach the ultimate goal of coming. Dillon was in heaven and hell at the same time. He was fucking the two sexiest women he knew, but he could not feel a thing, consequently, could not reach the final pleasure. The women abused him verbally and he loved it, but no matter how much they tried to stimulate his little pecker with their hands or their pussies, or even their mouths, he could feel nothing.

Finally the women got bored. They peeled off the condoms, washed his penis with a warm cloth and left the room. Dillon was left to wonder when they would come back. He sat there restlessly for a long while. His cock throbbing and bouncing from the Viagra. He couldn't understand how his cock was still hard after so much time with the women gone. He could hear the sounds of sex down the hall and figured it must be from hearing that. It was another hour before the two women came back. His pecker had finally relented, it was merely a semi by this time.

The numbing cream had worn off by now for the most part and the Viagra cycle was done as well. Still, being young and horny it didn't take but three or four strokes of his little cock to get it hard again. Grace told Kendal to watch as she brought Dillon to the edge at least ten times, telling him about how for the last hour she and Kendal had been in the living room eating each other's pussies and making each other come. Dillon was so aroused again, he didn't know what to do. Grace kept him like this for some time, finally asking him if he wanted to come.

"Yes Mommy, so badly." He told her.

"Now, watch this." Grace told Kendal. "This is the best thing ever."

"Beg me!" She commanded Dillon.

"Pleeeeeeeeeease, Mommy, Pleeeeeeeeeeease."

"Isn't that grand?" she asked Kendal.

"Oh my gawd, yesssssssss!" Kendal mused.

"More!" Grace demanded of Dillon.

"Oh Mommy, please. Please, please, pleeeeeeeeeeease, let me come, Pleeease, I need it sooooo baaaaaaaaad." Dillon pleaded.

Both women laugh hysterically.

"Have you ever seen anything so pitiful?" Grace quipped.

"Holy fuck, no." Kendal replied, "No real man would ever beg like that to come. Are you going to let him?"

"I have to, or we won't get him back in his cage for hours, besides, I haven't let him in some time and it's unhealthy not to drain his puny little testicles at least occasionally. But watch, this, this is the best part."

With that, Grace stroked Dillon vigorously and watched as he rapidly approached orgasm. He huffed and puffed and eventually let out a huge grunt and cum shot out of his penis like a missile. Just as it left his cock, Grace let go. His cock vibrated uncontrollably and cum continued to spurt several times, as his cock bounced up and down.

"Nooooooooooooooooooo!" Dillon screamed as his mother ruined his orgasm. "pleeeeeeeeease, mommy, nooooooooooo! Touch it again touch it! Touch it, pleeeeeeeeeeease?"

The spurts stopped after three and cum was rapidly now flowing out of his spasming penis and down over his recessed ball sack, puddling on the seat like lava running from out of the top and down the side of a volcano. Dillon was almost whimpering now, begging his mother to help him.

"What was that?" Kendal implored, "That was the hottest thing I have ever seen."

"That my dear, is called a ruined orgasm. All the benefits of coming for the body's health, but none of the pleasure for the mind. It's a cruel little reminder to my Dilly of who is in charge."

Kendal let out a croak of laughter, "You are fucking unreal." She told Grace.

Grace untied Dillon and then said to Kendal, "...and this is another reminder."

"What's the rule when mommy lets you come?" She asked Dillon.

"I have to clean up my mess." He replied dejectedly, not wanting Kendal to see this humiliation. He knelt on the floor and slurped up the puddle of cum from the chair and then the remains of the spurts that had landed on the floor. Kendal laughed uncontrollably the whole time. Dillon was crushed, lowering his self-esteem even more, thus making him even more reliant and subservient to his sexy domineering mother. It was a vicious cycle, but one Dillon craved deeply inside, even if his conscious mind didn't know it.

A few days after this, Grace decided she was done with Kendal and Levi, leaving them to work things out on their own, or not.

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The next step in the humiliation of Dillon would come from Grace reading more femdom forums. Everyone had so many ideas for her and they were oh so helpful when she asked questions. Many of them informed her that the ultimate submission for a male sub to a female domme was to be on his knees like a slut, sucking her strap on, or even better yet, being bent over like a bitch taking that same strap-on up his pretty little asshole. They also suggested feminizing him. Grace wasn't sure she wanted to dress Dillon up like a girl with a wig and make up and dresses for the outside world to see as some of the posts suggested, but making him wear some lingerie in the privacy of their own home as she performed these acts might be fun.

Grace had been planning this next humiliation for a while, buying everything she needed and trying to figuring out how she could manipulate Dillon to make this scenario happen, when finally, she just decided, Dillon will do as he is told and she marked a day in her mental calendar to turn her submissive little son into a cock sucking taking it up the ass sissy.

It was a Saturday and Grace had Dillon running all over doing chores around the house as she lounged around from her long week at work. She kept hinting that tonight might be a special night for both of them. This of course just made Dillon try harder to please his mother the whole day. After dinner, Grace sent Dillon to shower and told him she would leave somethings on his bed to put on when he was finished. She told him he was to do this without question and to meet her in her room when he had complied. If he failed to do as he was told, there would be consequences.

With a stern look she said, "And, we both know you do not want to face those, right Dilly"

"No Mommy." He replied.

"Besides, Buttercup, Mommy thinks you might like what I have in store."

The whole time he was in the shower he was excited, but at the same time anxious about what she had planned for him. He knew that every time they did something new, it was always humiliating, but then again it was usually the most exciting sexual adventure of his short life. So he resolved to have an open mind. That open mind slammed shut the moment he walked into his room.

On his bed laid out perfectly, all made of pink silk, were an "A" cup bra, garter belt, g string panties, seamed stockings, 3 inch close toed stiletto heels and of course a new pink plastic chastity cage. Dillon stopped dead in his tracks when he saw it all. He was not going to wear this stuff. This was for girls and he was not a girl. He immediately turned around and began to call for his mom. However, after beckoning his mother just once he recalled her ultimatum. He did not want to suffer his mother's consequences. He remembered his pledge in the shower to have an open mind, and he called back instantly to his mother, "Never mind."