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Nana Comes to Babysit
Note to the reader:this is the fourth installment in the ‘Mikey’ series. They are, in order: 1. Penis Reduction Therapy for Sissies, 2. Milking My Sissy on Date Night, 3. Taking Control From a Sissy, and 4. Nana Comes to Babysit.

Nana Comes to Babysit
Mikey stood at the threshold of the master bedroom’s bathroom, aware his wife was just inside, putting her makeup on and getting ready for her date with her boyfriend. As he stood there uncertainly in his diapers, sissy top, and Mary Janes, he was trying to marshal his best arguments, hoping against hope to persuade her to unlock his chastity device and allow him to have an orgasm.
  Stepping slowly into the bathroom, his eyes roamed over his wife’s curvy form, marveling at her long, sexy legs and pert bottom in the form-fitting short skirt she was wearing. She hadn’t put her top on yet and Mikey stared hungrily at her big breasts, barely contained in her silky black push-up bra. Of course, Kendra would never allow Mikey a look at her nipples anymore, so this was as undressed as he would ever see her.

   Horny beyond words, his tiny penis throbbed madly inside its even tinier steel chastity device, completely unable to get hard. Without thinking, his hand reached down to rub the fat front of his shiny diapers, although it was an entirely futile gesture.
  “M-Mommy?” he began in a quivering voice.
   Kendra was applying a wine colored lipstick to her full, luscious lips and she continued what she was doing without turning around. 
  “Yes, sissy?”
  “Um, there any way you might, um, know, unlocking my chastity device tonight?” he asked meekly, “I really need to cum.”
  His sexy wife chuckled to herself as she turned to face him.
  “Aww, is Mommy’s little masturbator horny?” she asked in her syrupy voice meant for toddlers.
  Mikey blushed but nodded his head, hoping his act of humility would somehow convince her to be generous with him.
  “But you got to cum in your prissy diapers just a week ago, remember honey?”
  Mikey did indeed remember the event, as the humiliation of it still caused him to blush hotly with shame.

   The day had finally arrived after having waited two agonizingly long months for his one cherished orgasm. But instead of unlocking his little penis and letting him pleasure himself in his nursery to an eye crossing climax, Kendra had instead marched him out to the living room, where four of her girlfriends were waiting. After pulling his wet diapers down, she unlocked his steel device and slowly pulled the cage off, revealing to his curious onlookers the flexible urethra insert that went inside him by about two and a half inches. Mikey sighed with relief as she pulled it away and then removed the cuff ring behind his diminutive package. He thought she’d pull his diapers back up but instead, she paraded him before each of her guests, just to let them see how truly tiny he was. Although he had already been ridiculously small when Kendra had met him, after six months of her penis reduction therapy, his little nub had been shortened down to one inch, even when fully erect. As a consequence, even when he wasn’t aroused, just the tip of his penis head protruded from his groin, like a tiny mushroom cap.
   The girls had laughed and giggled at his baby-sized wiener, which made him look practically sexless, causing the poor sissy to nearly cry with shame.
   Finally, she pulled his clammy wet diapers back up and sat him down in front of everyone, telling him to do his dirty deed now or never. Faced with the prospect of another two months without relief, Mikey began rubbing the front of his soft, fluffy diapers as the women laughed and mocked him with their jeering comments.
   As he frantically rubbed himself like a desperate, horny teenager, he tried without success to shut out their biting remarks about how absolutely pathetic he was. Finally, after a minute of furious rubbing, he sighed and his shoulders slumped as he dribbled his little load into his wet diapers. It was so anticlimactic that the girls weren’t sure he had actually cum.
   “All done, sweetie?” Kendra asked, bending over her humiliated charge.
   His cheeks scarlet with shame, he nodded shamefully and let her stand him up so she could pull his diapers back down. Having carefully washed his urethra insert, she pulled his little genitals through the cuff ring and then aligned the tip of the insert with his pee hole.
   “Here you go honey, two more months of sweet chastity for my little sissy masturbator,” she said as she slowly guided the insert inside and carefully mated the steel cage with the cuff ring behind his sack. Mikey bit his lip in angst as he watched his beautiful wife lock the device with a smug grin, knowing that after his humiliation had finally faded, his libido would eventually return but there would be absolutely nothing he could do about it.
   “Yes Mommy, but I’m horny again,” Mikey whined, stamping his feet in frustration as his barely clad wife stood smiling before him. With her finely manicured hands resting on her curvy hips, the light shone off the succulent tops of the twin mounds of her magnificent bosom, making Mikey’s mouth water.
   “Aww, you poor little sissy,” she replied with puckered lips, although her tone suggested she was anything but sympathetic, “But don’t worry, you only have seven more weeks and you’ll get to cum again.”
   Her smile did nothing to assuage his need and he shifted his Mary Jane-clad feet, trying to think of his next line of appeal. Seeing that he wasn’t ready to concede, Kendra reached forward and taking his cock-shaped pacifier, worked it between his trembling lips until the fat, phallic rubber completely filled his mouth, silencing any further comments.
   “Now sissy—Ariel called and said she can’t make it tonight so instead, Nana will be babysitting you,” his wife explained as she turned back to the mirror to brush her lustrous long hair.
   “N-Nana?” Mikey quaked as his pacifier tumbled out of his mouth. He gulped in fear as a strong flow of warm pee abruptly began flooding his big, bulging diapers. Unfortunately, by now, he had lost all control over his bladder and he often wet himself without even thinking about it.
   “Yes sissy,” she said as she pushed his pacifier back into his mouth, “So I would suggest you be on your best behavior. She told me she bought a new lexan paddle and she’s anxious to try it out on your bare bottom,” Kendra explained with a twinkle in her eye.
   Another strong flow of panic-induced pee saturated the thick cloth between Mikey’s inner thighs, before seeping back into the fat seat of his diapers as he considered the possibility of another blistering hard spanking over his stern mother-in-law’s lap. Gone, now, was any thought of an orgasm. Now, his priority was laser-focused on avoiding getting his bottom paddled by his strict Nana.
   Just then, they heard her voice coming down the hall, apparently having let herself into the house.
   “Hi Kendra,” she sang out cheerfully as she flowed gracefully into the bedroom. In her hands was a delicate baby dress, although clearly, it looked large enough to fit a small adult.
   “Hello sissykins!” she greeted her pantywaist son-in-law.
   Mikey never knew exactly what to expect from his unpredictable Nana; sometimes she made no attempt to hide her resentment and disdain for him, while other times, she seemed to be in a good mood, happy just to subject him to some new, creative humiliation. Without a doubt, she held absolutely no respect for the bedwetting sissy and she was only too happy to make her feelings known whenever she happened to come over.
   Coming over to him, she threw her arms around him, hugging him close to her big, cushiony bosom. Reflexively, her hands dropped down to squeeze the fat but now warmed seat of his padded bottom.
    “Looks like Mommy’s little baby wet his pampers,” she announced in her maternal tone. 
   Mikey blushed as his childish wetting was revealed openly. Of course, the imposing rubber cock filling his mouth prevented any sort of coherent response.
   “I’ll change your diapers and then look what I brought over for you to wear tonight,” she said excitedly as she held up the dress for them to see. It was multilayered, with several frilly white lace petticoats that flared the short hem of the dress out at an angle. It had short, puffy sleeves, and a Peter Pan bodice over the white and pink accented dress. Lemon yellow building blocks were prominently sewn onto the chest, giving it a decidedly babyish look.
   Mikey sucked and slurped on his cock pacifier in frustration; while his wife had chosen ever more sissyish outfits for him to wear, Nana preferred much more infantile ones to go with his omni-present diapers which he was forbidden to cover.
   Kendra was pulling a stretchy top over her head and as the thin fabric slid over her huge breasts, Mikey gulped and held his breath, his horny feelings returning with a vengeance.
   As if reading his mind, she addressed Nana;
   “Mom, can you give Mikey a nice, soapy enema this evening and an early bedtime?”
   “Done and done,” she said with finality, “Looks like you’ll be taking a trip over my lap, bedwetter boy,” she said with a firm, superior look.
    Mikey wilted as he reflected on the huge rubber dildo nozzle that was used to administer his daily enemas and his ill-considered appeal to his wife for relief from his strict chastity schedule.
   “Come along babykins,” she said condescendingly, slapping his diapered bottom dismissively, “Let your mommy finish getting ready for her date with a real man while we change your wet pampers.”
   Taking him by the hand as she would a child, she led him waddling down the hallway and into his still relatively new nursery where his crib, playpen, and diaper changing area awaited him.
   “Okay sissy, let’s get you into some nice fresh diapers—I’m anxious to see how your new dress fits,” she told him eagerly.
   Tugging down his clinging plastic panties, the soggy, pungent cotton of his diapers sagged heavily, surrounding them with the humiliating smell of his incontinence.
   “You really are just a big baby, aren’t you?” she asked rhetorically.
   Mikey whimpered with shame. It was still fairly recent that he had lost control over his wetting during the daytime, a shameful development that his mother-in-law never failed to point out.
   Removing the pins from either side of his hips, Nana dropped the smelly wet diapers into his bin and sat him down on the changing table.
   “Your mommy is going out on a date with her boyfriend tonight,” she told him as she busied herself preparing a fresh set of diapers for her sissy son-in-law, “He’s a real man with a real cock—not a little bump like you have,” she said disparagingly, “I knew you’d never be able to satisfy Kendra and I am so, so happy she decided to lock your little sissy stick in steel chastity. Sissies don’t need orgasms like real men do.”
   Mikey slurped on the fat rubber cock in his mouth, unable to contradict his Nana without risking a spanking.
   Raising his glossy pink Mary Janes over his head, Nana smeared diaper rash cream across his bottom, giving it a nice, sticky white coating.
   “No, this evening, while you’re asleep and peeing your diapers like the sissy bedwetter that you are, Kendra will be getting satisfied by a hunky stud, one who I’m sure will be pumping her full of his thick, manly semen. Just think—imagine if her gets her pregnant? Wouldn’t that be wonderful?” she asked breathlessly.
   Unfortunately, Mikey could imagine it all too clearly and he cringed at the thought. He reflected on the contrast she was painting; Kendra’s masculine boyfriend would be coming over before long while all he could look forward to, was a long, humiliating enema over Nana’s lap and an early bedtime like any diapered toddler. Perhaps worst, was the knowledge that while everyone else was up and having a good time, he’d be alone in his crib with only his teddy bear and pacifier to keep him company. Just like every night.
   Powdering generously with fragrant baby powder, Nana pulled up the fluffy thick cotton cloth, pinning it tightly and securely on either side of his waist.
   “There, that should protect Mommy’s little baby in his crib,” she said as she sorted through the stacks of plastic panties, trying to find the best match for the dress she had brought over. After a moment, she selected a white pair with a pattern of pretty pink bunnies. Fitting them over his Mary Janes, she pulled them up his smooth legs and thighs, working them over the fat, bulky Birdseye cotton of his diapers.
   “You know, if someone had told me a year ago I would be pinning my daughter’s hubbie into his nighttime diapers so Kendra could go out on a date, I would have said they were insane. But then, I didn’t know she had married a sissy bedwetter and it’s clear you belong in diapers like a little baby.”
   Mikey’s face flushed hotly at her humiliating words and he sucked miserably on his pacifier as she powered between his inner thighs.
   “Okay sissykins, sit up so we can try out your new dress,” she commanded him.
   Doing as he was told, Nana pulled off his fuzzy fleece Strawberry Shortcake diaper shirt and lowered the frilly confection she had brought over. Turning him around, she did up the long row of small buttons that secured the dress up the back and also prevented its removal by the diapered pantywaist. Standing him up, she pulled the hem out and adjusted the petticoats, a smile coming to her face.
   “What a perfect fit!” she gushed happily, “And look at how your pretty panties are still easily visible.”
   Mikey gazed at his prissy reflection in the wall mirror opposite, his cheeks blazing red at his humiliating appearance.
   “Let’s go out and show Mommy before she leaves,” Nana said as she took his hand and led him out of the nursery. They soon heard Kendra’s voice, and then the deeper sound of that of a man coming from the living room. Mikey winced in fear and tried to wrench his hand from Nana’s but she held on tightly and firmly led him in to face the humiliation he knew was coming.
   As soon as Mikey came into view of Kendra’s boyfriend, the man burst out laughing, almost doubling over as he took in the sissy in his babyish dress and fat, prissy diapers.
   “Oh-my-god, I can sure see why your wife locked up your penis,” he said as soon as he could talk again.
   If Mikey hadn’t wet himself just a half hour before, he would have flooded his diapers now in anxious panic. Nevertheless, his breathing became erratic and rapid as he sucked feverishly on his cock pacifier, his eyes darting nervously around the room.
   “What a lovely dress!” Kendra exclaimed, “Mikey, did you thank her for her wonderful gift?”
     Mikey stood there, looking absolutely ridiculous as Nana squeezed the thickly padded seat of his diapers, making him squeal in surprise. Everyone laughed when they saw the distressed look on his red face.
   “Get over here sissy boy,” the man ordered him in his gruff voice.
   Comparing the two side by side, their differences couldn’t be any more pronounced. Kendra’s boyfriend stood over six feet, with broad shoulders, and a chest like a barrel. Mikey, by comparison, was a good foot shorter, slight of frame and looking more like a scared little girl, than an adult man. With his smooth, shaved legs, fat, shiny diapers and his prissy new baby dress, he looked like a toddler in need of his mommy.
    Waddling uncertainly over to the man, he looked fearfully up into his strong face with its solid jaw and his imposing stature.
    Roughly turning Mikey around, he ordered him to raise the back of his dress. Fearing a hard spanking in front of these two, Mikey meekly did as he was told.
   Standing there as the other two watched him, he heard the man unzip his fly and his panic level only increased. Suddenly, he felt the elastic waistband of his plastic panties and the back of his diaper being pulled back. Before he could make sense of what was happening, he felt a hot stream of pee splashing forcefully on the crack of his ass as Kendra’s boyfriend began using his diaper as a urinal. Mikey whimpered with shame, bunching his fists and slurping noisily on his cock pacifier in bitter, humiliated frustration. The women giggled at him and Mikey’s eyes misted with tears of embarrassment. He knew he should have stood up for himself and put a stop to this but he was too spineless to do anything. He felt like he was being marked like the branding of a steer and yet, he stood there and did nothing, blushing furiously as the hot pee pooled up between the glistening white globes of his bottom, before finally soaking into the seat of his diapers and between his legs. In no time, the warm pee seeped up to surround his tiny caged genitals.
   Kendra had the wherewithal to take out her cell phone and snap several shots of the spectacle while Mikey squirmed in helpless, sissy submission. 
   At long last, and after what seemed like an eternity to Mikey, the man finished his business and he slapped the sissy’s soaking wet bottom with a condescending swat. Mikey squealed, his mouth still filled with fat rubber cock as his diapers sagged heavily with warm pee.
   “Okay baby, time to say goodbye to Mommy and then it’s enema time for you,” Nana told him.
   Mikey whimpered as Nana pulled his pacifier out of his mouth and turned him to face the other two.
   “Nite-nite, sissy,” Kendra giggled merrily.
   “N-night, Mommy,” Mikey mumbled under his breath.
   Nana swatted his diapered bottom again.
   “You can do better than that. And make sure you thank her boyfriend for satisfying her like you never could. Better make it good, or you’ll be getting your bottom paddled after they leave,” she warned ominously.
   As if getting his diapers peed in wasn’t punishment enough, she had to threaten him with a spanking too!
   Mikey gulped and cleared his throat.
   “Th-thank you, Sir. F-for satisfying Kendra like I never could. I have a tiny little penis that can’t stay hard or satisfy a woman and so Mommy quite rightly locked it up permanently. Mommy says that s-sissies like me that wet the bed need diapers, not orgasms, and I know deep down, sh-she’s right.”
    The shameful statement made him blush anew and Kendra giggled at his submissive admission.
   “Enjoy your soapy enema and your wet diapers tonight, sweetie—I’ll be enjoying a real man and his nice, hard cock inside me,” she said with a mischievous, but ravishing smile.
   Pushing his cock pacifier back into his mouth, Nana led him waddling out of the room as the amused couple said their goodbyes and left the house.

What a story. If he’s learned anything here I suspect it’s that the treatment he receives from mommy isn’t actually quite so bad when compared with the treatment he has received here.  Wink 

The nappy being used as a urinal was a particularly interesting twist and reminds me very much of when I once had to wear my sister’s used nappy.
A great story indeed. Nanna and Kendra are lovely but I hope her boyfriend doesn’t move in or things would be much worse for Mikey. The dress Nanny bought Mikey is beautiful.
Very good! Like Girlygirl, I was particularly taken by the man using Mickey's nappy as a urinal. So humiliiating.
Know thy self, sissy.  Don't whine, don't pine, learn to expand your mind.   
Thanks Bobby, I always look forward to reading your stories and now there are two in a row.
Thanks again, Jiff
That’s a lovely story, Bobby, thank you.

How almost unbearably humiliating being dressed as a baby in front of your wife’s boyfriend, and then having to meekly stand there while he wees into your nappy. Maybe next time he will be made to turn around and take the boyfriend’s cock into his mouth to show his truly submissive nature.
He won’t thank you for giving them ideas.  Wink

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