Dangerousangleofadream - Femdom

Nana's Retribution

Note to the reader: This is Part seven of my Mikey series.

Nana’s Retribution

Mikey sat sullenly in the child’s car seat of his wife’s Lexus SUV as they made their way across town. Brad, her hunky boyfriend, was driving and occasionally Kendra would stop fondling his crotch long enough to look back with a smug smile to check on Mikey. Grumpily sucking his cock pacifier, the sissy wondered what his sexy wife had in mind for him. She had dressed him in a dainty, satin pink and white baby dress, pink plastic panties over his big, bulging diapers, knee-high school girl socks and his shiny black Mary Janes.

   By the standards of sissy fashion--he looked absolutely adorable.

   Still, as they made their way across town, Mikey shifted uncomfortably in the snug child’s seat. The fat, punishment butt plug that had been stuffed inside him at home was starting to make his back hole ache and he couldn’t get comfortable.

   As the car pulled off the main highway, he soon recognized the route they were taking to Nana’s house and it filled him with dread. Without realizing it, his diapers suddenly grew wet and warm and he let out a little whimper, even as he sucked desperately on the fat rubber cock filling his mouth. No good ever came of his visits to his Nana to be babysat by her, and more often than not, they resulted in a hard, bare-bottom spanking over her firm lap.

   Pulling into the driveway, it was apparent that Nana was outside talking to her next-door neighbor. This did not bode well for the diapered sissy, as it almost certainly meant spending some time outside, publicly exposed before everyone. He winced as Brad shut the car off and the two of them got out. Coming around to the back door, Kendra opened it and beamed down at her sissified husband.

   “We’re here, sweetie!” she said eagerly as she unbuckled his seat belt and helped him out of the car. Mikey blushed a bright red as Nana and her neighbor came over to look down at the sissy.

   What a cute little dress you’re wearing,” she said in her voice intended for toddlers, “Did you make it over without wetting your diapers?”

   He could only imagine what this stranger must think of him—dressed as a prissy diapered toddler girl while his wife is about to go on a trip with her hot boyfriend.

   Mikey blushed again and stared at the ground. Just then, a light breeze came by, lifting the delicate, lacy hem of his dress and he squealed as he fought to pull it back down.

   Nana’s attractive neighbor stepped forward and rubbed his smooth upper thigh appreciatively.

   “My, you have such baby-soft legs—perfect for a sissy in pampers.”

   Slipping a couple of fingers inside the elastic leg holes of his pink plastic panties, she felt the warm wetness of his diapers.

   “Looks like this little sissy is going to need a diaper change,” she announced.

   Mikey looked away as Nana shook her head in disdain.

   “Come along, bedwetter boi,” she said as she grasped his wrist, “We’ve got some business to take care of.”

   “Thanks for babysitting, mom,” Kendra said as she gave her a brief hug before returning to the car, “We’ll be back tomorrow."

   After saying goodbye to her neighbor, Nana led the humiliated sissy into her house. It was when he spied the wooden Spencer paddle laying out that Mikey shivered with fear.

   “We’re going to have a little discussion,” Nana announced ominously as she took a seat on the armless chair in the center of the room, positioning Mikey at her side. He couldn’t help but stare down at the yawning cleavage of her big, maternal breasts, proudly stretching the low-cut top she had chosen to wear. Were he not about to get paddled, his tiny little penis would almost certainly be throbbing with need inside his steel chastity device.

   Nana regarded him severely.

   “I’m told that your babysitter, Tiffany, allowed you to have an orgasm. Is that right?”

   Mikey’s knees trembled and he felt another flow of warm pee escape, to seep into the thick seat of his diapers. He knew his mother-in-law’s strict views on chastity, and he tried desperately to think of an excuse for his unauthorized release.

   Slurping noisily on his cock pacifier, he reflected that ironically, just the next morning after it had happened, he had awoken to his usual soaking wet diapers and a fierce need for another orgasm.

   How fleeting that brief pleasure had been!

   Nana grasped the pacifier and pulled it out of his mouth, leaving a string of drool between it and his mouth.

   “What do you have to say for yourself?” she demanded sternly.

   “It-it wasn’t my fault!” Mikey cried, “Sh-she made me do it.”

   “She made you have an orgasm?”

   Mikey nodded his head. “Uh-huh, she unlocked my device and made me rub up against Francis.”

   Nana barely stifled a smirk as she imagined the scene. Of course, Kendra had told her all about it and even showed her the pictures that Tiffany had shared with everyone, but it was still amusing to hear about it from the trembling pantywaist before her.

   “You know that sissy bedwetters don’t deserve to cum, don’t you,” she said as more of a statement than a question.

   Mikey nodded sadly.

   “—And yet, you still went along with it.”

   “Sh-she made me!” he wailed even as tears began to mist his eyes.

   “Well, your behavior has earned you a good, hard spanking. I hope your little ejaculation was worth it, because now your bottom is going to pay the price.”

   “No-no-no!!” he cried in his pouty voice as he frantically danced before her like a petulant child.

   Reaching under the frilly hem of his baby dress, she yanked his dripping pink plastic panties down past his knees, revealing his soggy, pungent diapers underneath. Snatching his wrist, she threw him over her lap, positioning him so his feet barely touched the ground. Off balance like he was, it would be impossible to get up without her help.

   “I’m going to teach you a lesson, you little weakling!”

   Mikey squealed with fear and panic as Nana bent over to pick up the paddle. At the same time, his bladder released the last of his pee, completely soaking the Birdseye cotton cloth underneath him. Unpinning his wet diapers, she pulled them back to expose his soft, bare bottom for his well-deserved punishment.

   Raising the paddle high over her head, she brought it down with a terrific wallop, impacting both of his cheeks with an angry, blistering swat.

   Mikey wailed at the top of his lungs as hot, salty tears tumbled down his face.

   “I made sure to open all the windows, so cry your little heart out,” Nana remarked with a sneer as she smacked his damp cheeks harshly, one at a time. Stinging, crimson red patterns quickly formed over his tender backside as Nana peppered it with her wooden paddle. Mikey cried like the baby he was dressed as and he kicked his Mary Janes wildly behind him, helpless to stop his mother-in-law’s fierce retribution. Although his back hole had been aching when he arrived, the fat, imposing buttplug was the now the least of his concerns. Each scalding slap of the paddle seemed harder than the one previous, and Mikey howled in agony as the painful, humiliating spanking continued. The unforgiving oak bit into his soft, tender bottom cruelly, and Mikey sobbed with bitter indignation.

   Part of him was conscious of the fact that the next-door neighbor who had gleefully checked his diapers ten minutes ago could now clearly hear the childish punishment he was receiving. The sharp, crisp smacks of the paddle echoed loudly in the room, to be easily heard by anyone outside. Nevertheless, he cried and sobbed at the top of his lungs, knowing he was only confirming her opinion that he was nothing but a diaper-wetting sissy cuck.

   Nana shifted her attention to the still pink sides of his cheeks, and she delivered cruel, biting swats until his entire bottom was a dark, blistering, painful red.

   Just as Mikey was certain the spanking would never end, Nana set the paddle down with a clatter and lifted him up on his shaky legs. Grasping his wrist, she pulled him stumbling along down the hallway and into the nursery where he spent the majority of his time when his mother-in-law was babysitting him. The smell of plastic and rubber panties that had been repeatedly peed in assaulted their senses as they entered the room but of course, by now, both were quite accustomed to the odor.

   “I’ve got a special surprise in store for you today,” Nana eagerly explained to the still crying sissy. His wet diapers were dragging along the floor, carried along by his lacy plastic panties gathered around at his ankles.

   Holding a massive dildo in her hands she showed it to Mikey as he wiped his arm across his wet, red face. The dildo was attached to a stout harness and Mikey could see that a white hose led from its base, up to a red rubber enema bag, nearly bursting with what he assumed was warm, soapy water.

   “It’s called the Sissy Tamer,” she said excitedly, “The clever people at Sissies-R-Us came up with a clever addition to a regular strap-on dildo; the balls at the base are actually a one-way pump. When I squeeze them, they deliver about a half cup of liquid. They even sell a special ‘semen fluid’, that looks and tastes just like a real man’s cum.

   “Here—I’ll show you,” she said enthusiastically as she forcefully pushed him to his knees and began strapping the gargantuan dildo around her hips.

   Mikey whimpered with anxiety, but with his bottom still throbbing painfully, he knew better than to stand up to her.

   Without another word, Nana pushed the fat rubbery head of the dildo into Mikey’s protesting mouth, making him squeal in anguish and helpless frustration. Grasping the back of his head, Nana forced him to deep-throat the dildo, his cheeks stretching to capacity as he struggled and gagged.

   “Get ready sissy—mama’s going to cum,” she giggled with glee.

   With her right hand, she reached down and held the big, over-sized ball sack of the life-like dildo before squeezing it firmly.

   Mikey’s eyes went wide as a massive load of the faux semen suddenly erupted in his mouth, nearly choking him. He swallowed again and again, the warm, creamy load reminding him of the thick ropes of Brad’s cum when he was forced to satisfy the big man with his mouth.

   Pulling the dildo out of his mouth, Nana placed her hands on her hips as she beamed down at her sissy cuck-in-law.

   “What do you think? Does it taste like real cum?”

   Mikey nodded reluctantly as he licked his lips of some of the residual goo.

   “Okay sissy—time now for a nice, creamy enema!”

   “No-no-no!” he cried desperately as she bent him over the crib mattress and pushed his legs apart. Lubing the fat head of the dildo, she was careful to leave the 3/8” hole at the tip unobstructed.

   Grasping his punishment plug with her fingers, she pulled until it finally popped out of his anus, making him squeal loudly. Without warning, she positioned the imposing head of the dildo at his hole and began applying strong pressure. Mikey slapped the mattress as he wailed in anguish but all his efforts were for naught. The slippery dildo was rammed past his defeated sphincter and Nana pushed it forcefully deep into his rectum.

   “AAIEEE!!” he cried as his back passage was stretched painfully wide.

   As soon as Nana felt the giant phallus bottom out inside him, she squeezed the balls, delivering a warm batch of creamy goo deep into the squirming sissy.

   Pulling the cock out a few inches, she plunged it back in to the hilt and squeezed the latex sack once more. Mikey could feel the warm liquid getting ejaculated deep inside him and he moaned like a helpless little girl.

   Nana’s raping of Mikey went on and on. She settled into a rhythm of sorts, plunging the big, slippery cock in and out of him and squeezing the ball sack about every tenth thrust. Mikey wailed and moaned, his bowels growing fuller and fuller as each squeeze of the dildo’s sack forced another punishing batch of the liquid inside him.

   “When I’m done here, I’m going to pin you back in your wet diapers, sissy boi. The bathroom is off limits to you,” she told him in her firm, unrelenting voice.

   Mikey squealed again, and he wondered idly if his diapers would be able to contain all the liquid that was quickly becoming very uncomfortable inside him.

  Ramming her cock in deep, she held it there just to make Mikey wail in anguish. Grasping the balls, she squeezed them once, and then once more, delivering another emasculating load of goo to the sissy’s bowels. He slapped the mattress in frustration and kicked his Mary Janes behind him.

   “You were never good enough for my daughter,” she snarled as she plunged it back in and held it there, “A sissy bedwetter all your life—if only she’d known about your shameful past…”

   She emphasized her point with another hard ram of the dildo.

   “And if I ever find out you’ve had another unauthorized orgasm—I’ll paddle your bottom for a week straight!”

   Mikey cried out as the fat dildo was rammed to the hilt and another batch of faux semen squirted inside him.

   “Take it, you sissy bedwetter,” she growled.

   She slapped his right ass cheek hard, making him cry out plaintively. Mikey was getting his just rewards, and then some, today!

   The titanic dildo was slick and slippery with the cream Nana was using and she plunged it in and out freely, even as Mikey’s sissy hole was being stretched to absolute capacity.

   “The next time your babysitter offers to let you cum—you are to tell her no, under any circumstances, are you allowed to cum—do you understand me?” she demanded as she slapped his red, stinging ass again.

   “Y-yes mama,” he bleated as still more of the cum was pumped inside him.

   Finally, at long last, the red rubber enema bag hung flat from its tall stand. Nana slowly withdrew the punishing dildo as Mikey wheezed with relief. Still, as he gripped his teddy bear, his face inches from the pee-scented crib mattress, he felt bloated, weak, and totally defeated. There could be absolutely no question who the boss was in this relationship.

   Ever so gently, Nana lifted him up and set him down on the changing table where she’d arranged his wet, pee-soaked diapers from before. As Mikey whimpered, she pulled the sides up and pinned the thick, soggy cloth around his hips.

   “No point in giving you fresh diapers,” she remarked, “We both know these will be getting filled in a minute.”

   Sure enough, as Nana began snaking his plastic panties up his legs, he felt the enema liquid squirting out of his rear and filling the gap between his cheeks.

  “OH!!!” he cried, as Nana smirked down at him knowingly.

  Bringing him to his feet, Mikey glanced around nervously, just as he felt another sudden rush of more of the cream empty into his diapers.

   He moaned and blushed a bright red, the babyish sensation feeling very humiliating to him.

   “Come along now, we’re going to go next door so we can give the key to your chastity device to Denise,” Nana explained.

   Mikey stumbled along in a daze as more of the warm, creamy goo erupted from his hole and filled the back of his fat diapers.

   They walked outside and went over to her next-door neighbor’s door, ringing the doorbell as Mikey whimpered and squealed with each unstoppable release of his enema. By now, he felt like he was practically floating in his diapers!

   Opening up the door, the attractive, fortyish looking woman beamed down at Mikey’s crestfallen face. Nana took the small key from her pocket and placed it in Mikey’s trembling hand.

   “Hello Denise, little Mikey here earned himself a trip over my lap—I hope the noise didn’t disturb you.”

   Denise held her slim hand up to her mouth as she giggled with amusement.

   “Oh, not at all. And what did mommy’s little sissy boy do to earn a spanking?”

   “He had an unauthorized orgasm, which he knows very well is strictly forbidden,” Nana explained firmly.

   “Oh!” Mikey squeaked, as he helplessly felt another surge of cream erupt into his heavy, sodden diapers.

   “And now, Mikey has something he’d like to ask of you.”

   Bending down to the short sissy’s level, Nana whispered into his ear for several moments.

   Mikey blushed red with humiliation and he shuffled his Mary Jane-clad feet as the rest of his enema finally seeped out of his weakened, stretched anus.

   “Um, w-will you p-please take the key to my ch-chastity device…so no one will--will ever be able to unlock it again?” he stuttered, “I-I-I’m a sissy bedwetter and I’m--I’m not allowed to have orgasms like a real man.”

   Denise giggled and took the key from him, just in time for him to grip the sides of his heavy wet diapers before they fell down from the added weight.

   “I’ll be happy to take it, you sweet little sissy,” she grinned, “This will make sure your tiny little pee-pee stays nice and soft, with no more of those yucky orgasms. You leave the orgasms to real men, and they’ll leave the wet diapers and baby panties to you.”

   She giggled again as she gazed down upon his red, blushing face.

   “But it looks like those diapers have taken all they can. You better get your nana to take you home for a change.”

   He nodded sadly as he stared at the ground, unable to look the beautiful woman in the eye.

   Mikey was devastated to willingly give up the key to his chastity device but the reality was, deep down, he knew that he would always be a diaper-dependent sissy cuckold, and things like orgasms—something that every other male took for granted, were inappropriate for him. He would just have to get used to a life without cumming, feeling the ever-present gnaw of sexual frustration that is the daily lot for every chaste sissy in diapers.

THE END

Yep!

Gag testing

Memories... I did something similar when Seth and I first met (no leather dress though). His face was the same 🥰

When you agreed to look after the Boss’s daughter, nobody could prepare you for the enormity of the task.

She’s going to run you ragged, sunshine.