Dillon's Mommy Ch. 04

Grace was in her room preparing for her son's arrival when she heard the first call. She ignored it, knowing her son would not take long to re-asses his position. When his second call came almost as quickly as his first, she smiled to herself, knowing full well her son was completely under her thumb and would put up very little resistance to anything she ever expected of him.

Even though he knew he was going to eventually put all this stuff on, Dillon was still filled with consternation the whole time. Starting with the chastity cage, it took him almost a half hour to finally get it all on. On the other hand, as he did put it all on, something happened. As the silky material of each item touched his skin, it began to transform his feelings about dressing like this. He began to enjoy the feel of them against his skin. The juxtaposition between apprehension in his mind and the stimulation of his skin as he pulled each item on, was mind boggling to him. The garments actually kind of felt sexy, and progressively made his little wee wee quite hard. By the time he was done, and contrary to his anxious mind, his body was quite turned on and ready for whatever his mother had in store for him. It would not be long before his mind followed suit and melded with his stimulated body and gave in completely.

Grace had waited patiently for Dillon, knowing how hard it must be for him to accept this and do as he was told. However, the moment she saw him finally walk into her room, she could see by the twinkle in his eye, and the way his caged penis pushed the small triangle of material of his g-string away from his lithe body, that he was, as always, hers to command.

"Oh my sweet little Dillon, you look adorable. Come give mommy a hug."

Dillon gladly obeyed, loving the feel of him mother's body against his. The two of them slid about as the silk material of both their outfits rubbed against each other. Dillon nestled his head between Grace's massive breasts and moaned his approval.

"Ok sweetums, Mommy has some fun planned for tonight." She told him as she broke the embrace and stepped back a couple paces. "Tonight, we ae going to switch rolls. You, my dear, are going to be the girl, and mommy......" she grabbed the lapels of her full length silk robe and pulled it wide open, "......is going to be the man." Protruding from her thick pelvic area was a thin 5 inch strap on Dildo.

Dillon gasped with fear, "but mommy" he began to protest.

"Eh, eh, eh!" Grace warned him, wagging her finger back and forth at him.

"Dillon knew not to continue, "Yes, Mommy." He replied dejectedly.

"Now, now Dilly, don't be that way. It will be fun, I promise. And, if you are a good boy, er, girl, Mommy will let you cum, and not one of those mean ole ruined ones she likes to give you." She assured him.

Dillon immediately perked up.

"That's my good boy. Damnit, I mean girl." Grace corrected herself again.

"Now come here and get down on your knees like a good girl and suck mommy's cock!" Grace commanded, immediately switching to the dominant woman she was with her son.

Dillon moved toward her slowly but gave no resistance as he did what he was told. Melting to his knees directly in front of grace, he reached up and grasped the skinny dildo and directed it to his mouth, tentatively sliding in a few inches.

"Now, mommy knows you have never had a real blow job. Well, not one you could feel, but you have seen Kendal and me administer many of them. Think about what you have seen and listen to me." Grace instructed Dillon.

He was petrified of what this said about him and he was reluctant to perform with any kind of enthusiasm. His motions were rigid and hesitant. He did what he remembered seeing, but would not do it eagerly.

"Real men like the tongue, Sweetie." Grace told him. "Lick the tip like it was a lollipop."

Dillon did as he was told.

"Good girl!" Grace mocked him.

Once again, to his surprise, the new form of humiliation sparked something in him, arousing him.

"Now. Lick the entire length, darlin'"

Dillon obliged, but this, he implemented with a bit of enthusiasm, as Grace had anticipated.

"Oh yes, what a dirty little girl you are Dilly, just like that slut ex-girlfriend of your, Kendal."

Dillon's pace increased and he was soon licking it enthusiastically. Grace noticed and pushed him further.

"OK buttercup, time to really be a slut. Open up and slide mommy's cock into your mouth."

Dillon didn't hesitate one bit. He opened up and sucked the small thin phallus into his mouth and began eagerly bobbing on it like an obedient submissive.

"Mmmmm, yes, Sweetheart, that's mommy's nasty little cock sucker. You can take it all. It's not too big, kind of like your little penis."

Dillon did as he was told and engulfed the entire fake cock. He looked up at his mom for approval and she gave it to him in spades.

"Oh Dilly, Mommy is so proud. Look at you swallowing her cock like a good little cock sucking slut. I'm not even sure Kendal does it as well as you do."

The degradation had the same effect on him it always did. It aroused him and he aimed to please his mother even more. He bobbed faster and deeper with each word. Soon there was saliva running down his chin and dripping off the rubber cock. Grace continued to encourage him and Dillon ate it up. This continued for quite some time until Grace finally stopped him. His lips and throat were turning red and raw by this time, his neck muscled were sore as well.

"Well baby, now that you have mastered cock sucking, we will work later on performing it on much larger cocks, it's time for you to prove what a good little girl you are for mommy's cock."

She stood him up and walked him to the bed. She bent him over the bed so his elbows were resting on it.

"Remember, not a word or mommy will be very upset. You don't want mommy upset do you?"

"No mommy." He replied, fearful of where this was going. It didn't take a genius to figure out what Grace had in mind.

There was a few moments of silence as Grace walked to the night stand and grabbed the lube and a condom Dillon had not noticed sitting there. First he heard her open the condom before she rolled it onto her fake cock. Then Dillon heard the top pop open on the tube and the distinct sound of gel squirting out of that tube. The next thing he felt was his g string being moved to the side and that cold gel being applied to his exposed asshole by his mother's finger. He let out a meager sound of protest before his mother shut that down instantly.

Once his ass was thoroughly lubed, Grace applied a generous amount to the dildo and without saying another word, unceremoniously slid the thin fake dick slowly into Dillon's ass. He instinctively resisted, tightening his asshole before Grace advised him to relax, rubbing his back to calm his struggle. Her soothing touch and out of character comforting words soon had Dillon taking that cock up his ass quite effortlessly. Once it was slid all the way in, Grace leaned over and pressed her mammoth jugs against Dillon's back and praised him for his acceptance.

"See Dilly, you are such a good little girl, taking mommy's cock so nicely."

Dillon never heard a word Grace said, he just relished the feel of his mother's tits against his back. Then grace reached around him and cupped his bra covered breasts, pulling the bra down and teasing his nipples. Dillon moaned his approval and Grace began to slide the dildo in and out as she pleasured his sensitive nubs.

It was definitely not pleasurable at first, but the breasts against his back and the teasing of his nipples made it more bearable. This went on for a few moments and Dillon finally relaxed. Grace could feel his resistance waning and soon she stood back up and grabbed hold of Dillon's hips and began fucking his ass with a bit more forcible rhythm. And her dominance returned.

"Who's mommy's little slut?" She said. Driving the cock in a little harder and a little deeper.

"I am." Dillon grunted.

He was not happy to reply that answer, but he knew it was the only acceptable one. Conversely, as Grace continued to assault his ass and verbally assault his manhood, he noticed a tingling in his ass and his caged cock. Suddenly he noticed that his cock was pressing hard against its confinement. He realized he was enjoying what he would learn later was prostate stimulation. He would research it and find out that there was such a thing as prostate stimulated orgasms for a man. However, at the moment he didn't know how to process this sudden arousal and acceptance of this situation.

Grace could almost feel Dillon's resistance fading. Of course, the gradual shift from painful grunts to pleasurable moans were quite a giveaway to her. She turned up the humiliation and picked up the pace.

"Dilly, tell mommy who is a dirty, little, slutty girl for her mommy's cock." She demanded.

"I am Mommy. I am!" he proclaimed.

Grace wickedly laughed at her submissive son, and fucked him even harder.

"Again! Tell mommy again, what a slutty little girl you are." She commanded

"I'm a slutty little girl. I am your slutty little girl!" Dillon declared.

"I love it! Again!" she cackled.

"I am your slutty little girl, Mommy. I am your slutty little girl." Dillon screamed. His proclamation and the humiliation was too much. He couldn't believe how much all this turned him on.

"Tell me who's a cock sucking, take it in the ass whore for mommy's cock!"

"I am! I am! I am!" Dillon shrieked, and as he did, suddenly his body began to convulse and he had one of the most intense orgasm he could remember. His body quaked, his spine tingled and his cock exploded all at once. As Grace laughed and laughed, she fucked him silly and his cock spewed jet after jet of cum from the pee slot of his pink plastic cock cage all over the side of the bed and the ground.

When his orgasm final subsided, he collapsed on the bed in exhaustion. Grace pulled the dildo from his ass and he melted down the side of the bed until he was sitting on the floor next to his puddle of cum. Barely coherent, Dillon didn't notice Grace peel the condom off and throw it in the toilet. She returned, stuffing her cock in his face.

"Good little girls always clean the cock that just made them come." She told him.

Still in a daze, Dillon opened his mouth and Grace fucked it for a few minutes, before she pulled out, unstrapped it from her body, threw it on the bed and walked toward the door.

"Oh, and Dilly?"

"Yes mommy?"

"Clean up that mess on the floor." She demanded.

"Yes Mommy." He replied, leaning over and licking up all the cum still sitting on top of the carpet.

Over the next few weeks, Grace trained Dillon even more with many dildos, each one gradually being bigger than the last. Soon Dillon was deep throating her biggest one, a full 10" long 6" around monster, and taking it up the ass like a champ. He not only didn't resist now, he actually looked forward to his mother domming him and taking him in the ass. Grace was so delighted with the speed of his progress that she implemented the next phase of her plan sooner than expected.

Grace had really enjoying her new role as the dominant one in all her recent relationships, but she missed being the one dominated as well. Her boss and her had not "seen each other" outside of work in a long time, and there really had been limited opportunities during the work days for him to give her the fucking she so desperately needed. She devised a plan to meld her two roles into one. She informed Dillon that her boss would be taking her out for dinner this weekend and that of course he would be bringing her home to give her a good fucking. She told Dillon if he wanted to watch again, like before, he could hide in the closet and observe. However, there was one condition. That was, that he had to dress in his sexy girl underwear when he was in there. Of course Dillon agreed, and looked forward to the weekend with great anticipation. Dillon had no idea of his mother's clandestine plan.

Saturday evening Dillon did his duty and prepared his mother for her date with her boss Jerry. She looked so sexy and Dillon wished he was the one for whom she was getting ready. Unfortunately, he was not. Grace patted him on the head and told him what a good job he had done getting her ready. She reminded him of the condition she had set for him to be able to watch Jerry fuck her like a real man. Dillon replied that he understood and Grace was off.

Dillon laid out the clothes he would be wearing when he was in the closet later and went to the watch some TV until his mother texted to let him know she was on her way. However, as he thought about his sexy girl lingerie lying on his bed throughout the evening, his little pee pee became hard in his cage. He was happy that his mother had put his pink plastic cage on tonight instead of his metal spiked cage. Otherwise he would be in great pain right now. The more he thought about his sexy intimates the more aroused he became. Eventually he could hold out no longer. He hurried to his room and put everything on, even though he didn't expect his mother's text for some time.

As he put it all on, he relished the feel of the silky pink teddy on his skin. How he so wished his penis wasn't caged. That way he would be able to feel the cool soft material against it. His pee pee twitched even more as he pulled the silk stockings, also pink, up each leg. He snapped the garter straps attached to the teddy to his stockings and he giggle inside as he caught a glimpse of himself in the mirrored closet doors. He felt so naughty and so sexy in his girlie undergarments. He slipped his high heeled shoes on and practiced his sexy walk. He couldn't believe how much he really loved dressing up like this. He went to his mother's room and lied on her bed. The silky bedspread made that swishing noise he loved so much when his teddy rubbed on it. He began to try and masturbate, but with the cage on it was no use. He remembered the stuff he read on prostate orgasms and within moments he had his finger lubed and was shoving it up his ass trying to stimulate the sensitive gland, but his inexperienced failure with this only frustrated him more. He tried for quite some time until finally giving up, lying unsatisfied until he dozed off. He was awakened by the sound of the front door opening and the drunken jovial banter between his mother and Jerry. Shaking the sleep from his mind, he realized he had left his phone in the TV room and must have missed his mother's text. He rushed to get up and get to his hiding space in the closet, but in his haste, he tripped on his high heels and crumpled to the floor in a heap. Before he could get up his mother and Jerry loudly stumbled into the room, stopped dead in their tracks and stared down at Dillon.

"What do we have here?" Jerry stammered.

Without missing a beat, Grace replied, "This was supposed to be a surprise for a bit later in the evening, but no time like the present."

She let go of Jerry and moved toward her son who was trying to get up off the ground. She put her hands on his shoulders and stopped his progress, leaving him on his knees.

"Remember that conversation we had several weeks ago at lunch about how you loved to have little Craig's List faggots come to your home and blow you as you tell them what a sissy they are?" She quizzed Jerry

"Uh Huh." Jerry replied with a devilish grin.

"Well,...." Grace continued. "......I have been training my little sissy son here for just that purpose."

Dillon's eyes popped out of his skull and his jaw dropped to the floor. At the same time, Jerry didn't hesitate one moment before pulling his zipper down, unbuckling his pants and dropping them to his ankles, along with his silk boxers. His cock was rock hard and Dillon was quite impressed. He had never seen it this close. Dillon just stared at it, wondering what it would be like to have a cock like that.

"Go ahead Dilly. Give it a try." Grace suggested.

Dillon looked up at her with uneasiness, hoping his mom was not serious.

"It's no different than when you suck mommy's cock." She assured him.

Dillon didn't want to do it. He looked at his mom with pleading eyes.

"Go on my dear sweet sissy son, show Jerry here what a good little cock sucking sissy you are." Grace urged a bit harder.

Dillon began to plead, "Please, Mommy....."

"Stop it!" Grace cut him off. "Do as you are told my little sissy bitch! Or would you like to face the consequences?"

"yes mommy.!" Dillon whimpered, hearing the magic word, "consequences". He opened his mouth and slid Jerry's throbbing cock inside. The feel of the warm stiff unit in his mouth was very odd, unlike the cold inanimate strap-ons his mother had fed him before. It was somewhat erotic, and when Jerry moaned approvingly, it actually gave Dillon a sense of control that he didn't expect. That didn't last long, as almost immediately, Jerry grabbed the back of his head and shoved his cock down his throat without warning.

'That's it you little sissy faggot, suck that cock like a fuckin whore!" Jerry snapped.

Dillon's training from his mother was put to use very quickly. Just before he began to gag, he relaxed his throat and the hot hard meat missile slid right down. The feel of the warm meat in his gullet and the words from Jerry had Dillon very aroused. His penis sprang to life immediately and he took to sucking real cock like he was made to do it.

"Oh Gracey, my sweet, you have taught this little homo well. Look at him deep throat my cock. He is a natural." Jerry praised her.

"I completely agree Jerry. It took some doing, but my little sissy has learned." Grace replied.

This made Dillon proud and he doubled his efforts, grabbing the man meat with one hand and the accompanying ball sack with his other and massaged them both as he continued his expert cock sucking at the same time.

Grace and Jerry admonished the boy mercilessly for the next 15 minutes, calling his every name in the book from cock sucker to faggot, referring to him as a "she". The more they piled on, the harder Dillon's penis got and his effort increased. Jerry announced he was going to come, and Grace instantly grabbed a handful of Dillon's hair, pulling him away from his duty.

"Oh no you don't my little sissy cock sucker. You only get to taste Jerry's cum after it has been deposited into Mommy's cunt!" she scolded. "Mommy didn't bring Jerry here for you. She brought him here to fuck the living daylights out of Mommy while you watch and play with your useless little dingy."

Dillon rested on his haunches, disappointedly. He really wanted to be the reason Jerry orgasmed, and his mother had seen to that not happening.

"Thank you for getting that magnificent cock ready for your dear mother, Babycakes, but it's time for her to get what she deserves. A good hard fucking." There was a pause before she told him, "And Mommy has a surprise for her little man, well, little girl." she giggled. Pulling the key to his cage out, she handed it to him. You can let your useless little clit out and since you were suck a good little cock sucker, Mommy gives you permission to come as much as you want until Jerry does."

Dillon snatched the key from his mother's hand and couldn't unlock his penis fast enough. It sprang to full throttle as soon as the plastic sheath was slid off. He grab hold of it and immediately stroked feverishly, loving the feel and control he had over his own orgasm.

"You greedy little fuck." Grace chided him, before she just bent over the bed and allowed Jerry to stuff his man sized cock up her needy pussy.

Dillon came almost immediately, and as he watched his mother being taken by her dominating boss in every position possible, including in her ass, for the next half hour or so, he came three more times. The first time Grace reminded him he was obligated to clean his own mess before proceeding. Not wanting to miss any chance to have more real orgasms, he hastily licked every drop before proceeding with the next stroke session and impending orgasm. His pecker was literally raw and almost hurt more than it felt good while trying for his fifth orgasm when Jerry finally let out a throaty moan and deposited his load deep inside Grace's pussy.