Nanny’s Notes: 7 Ways to Punish a Dirty Diaper Ma*sturbator (Part 6)

The following post contains adult content and is intended only for adult readers over the age of 18. It is entirely fictional and all fictional characters described are roleplaying, consenting adults over the age of 18. As a friendly reminder, all non-fictional BDSM fantasy role-play should always and only be performed safely in the context of fully informed and consenting adults.

Punishment Method #6: The ‘Finish the Whole Pack’ Method

Despite it’s innocent enough sounding name, I firmly believe this to be one of the most severe methods of diaper punishment out of all of the above.

My father once caught me smoking a cigarette in the back yard when I was a young teenager.

The punishment he imposed on me for it was an oft-used one by his generation back in the day for that specific infraction.

He said that since I wanted to smoke so bad, I would sit down in front of him and finish smoking the whole pack at once.

Of course, it didn’t take more than a few more cigarettes for me to start coughing up a lung, vomiting, and earnestly swearing that I would never touch one of the awful things again. And it was true, too. I never smoked again.

So, how do we impose such a similar, delicious punishment on an unsuspecting diaper-submissive? Particularly in reference to the dirty sin of diapered self-fornication?

I’ll tell you how I did it.

* * *

“Alright, Daniel, the jig is up,” I said to the boy, an adult little one sent by his Mommy to spend the summer with me, in order to better learn obedience and submission to maternal authority. “It’s crystal clear now what filthy, perverted behavior you’ve been up to in your diapers the second I turn my back. You ought to be ashamed of yourself. It’s time to put you over my knee for a nice long session with the hairbrush.”

Daniel bowed his head, looked away in embarrassment. But he had the slightest of smirks on his face. And I could tell that deep down, he still felt like his perverted, soggy diaper masturbation session the night before was ultimately worth the blistering spanking he suspected he was about to receive.

This confirmed for me what I had suspected of this particular little one since he first walked through the door of my visitor’s nursery…

Daniel was almost surely a secret diaper fetishist—a filthy little pervert who conned his way into getting his domineering Mommy-figure to diaper him, so that he might regularly indulge his filthy, perverse diaper-lust desires behind her back, regularly callously stroking himself with filthy pleasure in his squishy diaper messes, making a mockery of the diaper-discipline imposed on him by his new Mommy, the woman in his life to whom he now owed only the strictest of submission, obedience and reverence.

I could have simply spanked him all the harder for the deed. I could have just seriously amplified his public humiliation and consistent shaming. I even could have just restrained him to the point that committing such a deed again would now be impossible going forward.

But no, I felt like none of this would be enough. None of this would achieve the desired level of long-lasting diapered submission that I wished to return him to his Mommy with at the end of the summer. After all, he might only endure such punishment measures with the same, secret, perverse fetish pleasure, no matter how severe those punishments were.

This meant I had to change tact. I had to impose a punishment that went deeper. One that transformed his very pleasure… into pain.

I had to teach this naughty little one a lesson he truly would never forget.

With Daniel over my lap, his naked bottom exposed, my hairbrush raised and just about to strike… I asked him a question.

“Daniel… do you like wearing your soggy and stinky diapers?”

He went silent for a second, clearly not sure what the ‘correct’ answer was. He finally squeaked…“I dunno.”

“You don’t know?” I asked. “That’s very interesting. Because most little ones do accept that they need to wear diapers now. But most don’t express hesitation about whether they like being in a stinky diaper. In fact, most littles would prefer to be changed out of their diaper by their Mommy relatively quickly, as they don’t necessarily enjoy sloshing about with a mushy bottom. They certainly don’t like rubbing their weewees till they make spurties in a dirty diaper, like you did last night. Especially when they know making spurties like that is very, very naughty. So I wonder, why don’t you feel the same way as other little ones about your soiled pampers?”

I sensed him blushing red hot. “Well… I dunno…” he said again, clearly feeling strangely trapped by my sudden line of questioning.

“Alright, little boy,” I said, putting my hairbrush down and standing him up before me in the nude. “I’m going to ask you a question. And if you answer honestly, I won’t give you a spanking, after all.”

He gave a nervous nod.

“Now, remember to answer honestly,” I emphasized. “Do you like the feeling of playing with yourself in your diapers, even if they’re soggy or soiled? Do you in fact enjoy playing with your little soldier even more than if you weren’t diapered at all?”

Again, he hesitated in terror.

“It’s okay, you can tell Nanny,” I said, gently rubbing his back. “I know that I’ve made it very clear to you that playing with your peepee and making cummies is a very naughty thing to do. But right now, you can just tell me the truth. I promise I won’t be mad. I just want to understand how you really feel about your diapees. Just tell me, do you like wearing diapers, using diapers, and playing with your peepee in your diapers, all even more than you’d enjoy not wearing diapers at all?”

Finally, he burst into tears. “Yes, Nanny!” he sobbed. “I just love my diapers! I love the way they crinkle! I love the way they feel puffy on my tush and between my legs. I really love the way they feel when they’re warm and wet and mushy. And most of all, I just love the way it feels to rub my little weewee in my diaper till it spurts in my already soggy mess! I wouldn’t want to ever do it any other way again!”

“Do you even like it when your diaper is poopy? Does that make your little soldier stand up even taller?” I asked.

He blushed deeply from head to toe. But finally, he nodded his head yes. “Please, Nanny, don’t be mad,” he immediately added with a squeak.

“Aww, there, there, little one,” I said, holding his naked body close. “It’s okay, Nanny’s not mad. In fact, I’m so proud of you for just being honest, like I asked. Which means I’m not even going to spank you anymore, just like I promised. In fact, I’m glad I now know you like wearing your diapers so much, even when they’re wet or stinky, just like a good little baby should.”

He looked up with hopeful eyes. “Really?”

“Yes, really,” I assured him. “In fact, because you were so honest, I’m actually now going to reward you with a very special gift.”

His eyes widened even further in surprise.

“Now that I know just how much you love and enjoy your soggy and messy diapers,” I explained with a warm smile, “from now on, I’m going to make sure you enjoy every single one of them to the fullest. Therefore, you won’t be receiving diaper changes anymore, until I watch you make cummies in the dirty diaper that needs to be changed.”

Daniel cocked an eyebrow, clearly taken off guard and not sure what to make of this ‘gift’ I was giving him. “Oh. Okay, thank you, Nanny,” he finally said, letting his guard down more as he processed it.

“You’re welcome, dear. Now come on, since you made cummies in your soggy diapee last night like a good boy, it’s time to get you changed into a new one. Oh, and now that I know you like crinkles so much, I’ll pick out a diaper that’s extra-crinkly,” I said, giving him a gentle pat on his naked butt and making him giggle.

* * *

If it dawned on Daniel then what the possible downsides of this new policy might be, he showed no sign of it at first.

In fact, it was clear that he was pretty quickly over the moon about his newly imposed ‘cummy’ requirement, despite being too embarrassed to admit it out loud.

In the first couple of days after our conversation, it seemed that Daniel was eagerly jerking his tiny peepee in his extra-large disposable diapers every chance he could get, arrogantly ‘cumming for a changie’ the first moment his diapers were only slightly damp with his pee.

He would run to me from the other room, grab the hem of my dress, and say with red cheeks, “I’m ready for a diaper change, Nanny!”

Then, I would smile and watch as he laid backward on the floor, shoved his hand into the front of his slightly soggy diaper, and furiously jerked himself until exploding with stickies.

He would collapse back onto the floor, sweaty and red-faced in his damp diaper and post-orgasmic shame-filled bliss. And true to my word, I would promptly then take him for a change into a fresh diaper.

In those first few days, it was clear that Daniel’s little baby brain was on a runaway fornication train, totally consumed with immediately satisfying his every horny diaper urge as quickly as possible.

But as you might have guessed… Daniel’s debaucherous spree of unrestrained self-gratification in his diapers quickly caught up with him.

It only took to the third day until it happened.

That morning, as he laid in his crib with his hand in his diaper, furiously stroking himself for his much-needed morning change… his over-beaten little pecker was finally just too exhausted to even stand at attention anymore.

Despite how badly he wanted a change out of his sopping wet overnight diaper—indicated by the impotent fury with which he stroked himself before me for 20 minutes—he still couldn’t do it.

Which meant he then ate breakfast… and lunch… in his ultra-soggy, pee-soaked, overnight diaper.

Several times between breakfast and lunch, little Daniel asked me for another chance to ‘make cummies for a changie’.

But I told him no. He had had enough time to do it that morning, and he couldn’t. Therefore, he was going to have to wait till after lunch to try to ‘make cummies for Nanny’ again.

After lunch, when I told him he was allowed to try again, he laid back on the floor and began once again attempting to successfully abuse himself in his diaper. But this time, it was clear he was far more nervous than he was before. It was apparent that the pleasure in the deed was already fading. And this time… I only gave him ten minutes to successfully ‘perform’.

Again… he failed.

A few hours later, Daniel’s thoroughly saturated diaper started heavily leaking, as could be predicted.

I suppose the smug, self-absorbed little masturbator assumed that this would mean I would finally change his diaper anyway, regardless of his little soldier’s failure to ‘stand at attention’ any longer. Especially since I responded to his leaky diaper by taking his hand and walking him back to his nursery.

But hah! He was in for quite a surprise when I put him on the changing table, and instead of taking his soggy wet diaper off… I merely wrapped a fresh, double-sized new disposable over the top of his soggy diaper, added another thick terrycloth diaper over that, and topped it all off with extra thick rubber pants.

I believe that was when the reality of his situation finally dawned on the naughty little diaper pervert.

He realized that he wasn’t able to cum nearly as often as he thought he could.

He realized I was equipped to have him wearing the same soggy, even soiled, diaper for a long, long time.

And he finally realized that what I had given him over my lap wasn’t a present, after all. It was a most sinister punishment.

* * *

It was later that same evening, just after dinner, that Daniel also discovered that the more desperate he was for a diaper change, the even more difficult his poor, tired little weewee found it to perform under the pressure.

“Aww, what’s wrong little guy? You seemed so excited to make cummies in your soggy diapees yesterday. Is my little boy’s little toy having some performance anxiety?” I gleefully mocked him right before bed, as he furiously yanked on himself harder than ever in his extra-thick, soggy diapers. But it was still to no avail.

“Aw, that’s okay. We can try again tomorrow,” I said with a satisfied smirk, patting him on the crotch of his mushy nappy, as he finally collapsed in exhaustion and burst into tears of frustration and regret at his inability to make cummies again.

“After all,” I continued, “Remember how much you said you loved making cummies in your dirty diapers? Even though you knew making cummies was a very, very naughty thing to do? I’m just giving you what you wanted, little guy. Just making sure you really enjoy your messy, squishy, stinky diaper to the fullest. Aren’t I such a good Nanny?” I quietly taunted him as I tucked him into his crib for the night.

I even gave his now absurdly squishy diaper crotch a firm, suggestive squeeze, making him whimper even louder with sexual humiliation and impotence, before I finally shut the door of his nursery for the night.

The next morning, Daniel did manage to finally eke out a few sad droplets of cummies before breakfast. And again, true to my word, I rewarded him by finally changing him out of his now filthy, sopping wet, mega-diaper that he’d been wearing, wetting, waddling and impotently stroking himself in, for more than the last 24 hours.

But despite little Daniel’s piddling success that morning, unfortunately for him, he was not to be so lucky for the rest of that day.

Which was extra-unfortunate, because the fiber supplements I slipped in his dinner that night meant he had quite the large, poopy load in his pants just before bed.

Daniel was tucked into his crib that night with a diaper firmly packed with his mushy poopoo. Just like the mushy poopoo diapers he secretly used to love toddling around in. But as you can imagine, he no longer felt even the slightest bit of fondness for his soiled disposable. Instead, he felt only discomfort, disgust… and utter humiliation.

The next morning, Daniel did manage to finally painfully squeeze a few more drops of cummies out of his peepee. He had been forced to do it while now wearing one of the poopiest, yuckiest, stinkiest diapers of his naughty diaper-stroking life.

And unlike every time he had ever cum in his diapers before… the mushy mess sloshing around his bottom and balls as he stroked himself, now only filled him with utter humiliation, disgust and revulsion at his shameful mess.

* * *

In the weeks that followed, the once hyper-eager diaper-humper began to loathe his stiff little pecker and the miserable few drops of sticky semen he could manage to produce only twice at most per day—and that was on a good day.

He began visibly resenting his sexual desires (or lack thereof) with audible moaning and self-disgust every time he was due to ‘try for a changie.’

Many a night Daniel spent rolling back and forth in his crib in his hot, heavy, mushy, poopy-loaded diapers, because he couldn’t manage to bring himself to orgasm yet again in his stinky diapers before bed.

And every minute he was forced to endure wearing his mushy, poopy, diaper mess, he would mentally self-flagellate, mortified with sheer disgust that he ever could have possibly found his disgusting, stinky, poopy, mushy diapers sexually arousing in any way at all.

(Thinking back, I suppose I didn’t help him any by only setting a five minute timer for him to do his ‘sticky deed’, as I sternly folded my arms and impatiently watched him pathetically stroke his sore, flaccid cock in his soggy, poopy mess in what had become his new nightly routine.

Or, in the times he did manage to make himself ‘get there’ against all odds, I would often, just at the last second, get a phone call and leave the room. And when I returned, just after he had finally managed to still shoot his dried up, pitiful load, I would merely tell him that I didn’t believe he’d made cummies at all.

But what can I say? I’m the Nanny. Aren’t I allowed to have a little fun with the naughty little diaper boy under my care? 😈)

* * *

By the end of the summer, Daniel’s perverse, sexual gratification with the diapers he was forced to wear had been all but obliterated.

His very orgasms had become a chore. An act performed only for someone else’s benefit. A monotonous, humiliating task he was forced to suffer day after day, hoping that he could at least manage to get two diaper changes that day, rather than the sometimes none at all.

And the diapers themselves, instead of being the source of fun, naughty, erotic escape, had become items of his filthy, humiliating, stinky imprisonment at the hands of a woman who now obliterated his any remaining dignity on a daily basis—exactly as diapers should be!

“Aw, what’s wrong Danny pumpkin?” I asked him one time as I changed his poopy diaper and wiped the mess off his flaccid, utterly beaten peepee. “You used to always have the biggest, naughty smile on your face when I changed your poopy diapers and wiped your little peepee with cool wet wipes. What changed?”

The little adult baby stared back up at me, mumbled incoherently for a moment like the drooling baby he was, and finally burst into pathetic, utterly humiliated tears.

That’s when I knew I had won. Little Daniel had finally smoked his ‘last cigarette’, so to speak.

It was time for the naughty little diaper pervert to finally get what was really coming to him.

It was time for his Mommy to finally return and take him back home.

* * *

The morning Daniel’s Mommy was due to arrive to pick him up and take him back home, I sat Daniel down and had a little conversation with him.

I explained that when he and his Mommy returned home for him to resume his care as her adult baby, his Mommy was more than prepared to maintain the same rule that I had implemented for him over the whole summer—the No Changies without Cummies rule.

He visibly shook in terror, mortified by the idea of never escaping his grueling, dirty-diaper-milking fate.

“However,” I explained, “Your Mommy is potentially willing to instead completely drop the no cummies without changies policy, and you will never have to masturbate in your diapers again. All it requires is that you agree to one small thing.”

Daniel’s eyes lit up. At this point, he was undoubtedly willing to do anything to end his grueling ordeal of required dirty diaper masturbation. He eagerly nodded his head.

That’s when his Mommy arrived.

As little baby Daniel sat on the floor before us in his puffy diapee, his Mommy and I presented the one small thing Daniel would have to agree to…

A chastity cage.

A bright pink, ultra-tiny, locking chastity cage.

A chastity cage, we explained, that once he agreed to let us put it on him, it would never, ever come off.

Daniel’s eyes widened. His heart pounded. It was clear the little device terrified him. He had never seen such a thing up close. He looked away, trying to put the device and the decision about it out of his mind. It all just seemed too overwhelming.

And yet… that’s when the laxatives I had slipped into his bottom that morning just happened to kick in. His tummy painfully rumbled. And out of unconscious reflex, Daniel climbed to his knees, squatted, grunted loudly, and much to his Mommy’s secret delight, he immediately soiled his diaper with a massive poopy load, right in front of us.

When he finally finished his stinky deed, he slowly turned around to see his Mommy giving him a stern look.

“Uh-oh. Danny!” his Mommy scolded. “Did you really just make a big stinky mess in your diadee right before we’re about to go home? Well, I suppose we’d better change you before we go, huh?”

Daniel looked up at us with suddenly expectant eyes… hoping against hope that one of us was about to walk him down the hall to his changing table.

But we didn’t budge. There was only a long silence as we stared back down at him with our arms crossed, all of us quietly suffering the growing stench of his poopy diaper.

Finally, his Mommy cleared her throat. “Well, hon? Are you going to lay back and make your cummies for us in your poopy diaper so we can change you, or not? After all, it’s going to be a long drive back home, and I doubt you want to be stuck sitting in your big poopy mess the whole way home.”

And that was when Daniel finally broke down. He suddenly burst into tears and began frantically agreeing to wear the chastity cage, after all.

He just couldn’t imagine suffering the humiliation of trying to ‘make cummies’ in one more poopy diaper. He couldn’t bear to suffer the humiliation and misery of even one more day of sitting in his poopy mess, pathetically attempting to stroke himself to completion, only to fail again and again. He was positively desperate to finally be free from the grueling, humiliating, painful regimen of endless self-milkings he had been forced to endure in his dirty diapers for countless weeks on end. He was finally ready to do literally anything.

His Mommy was secretly delighted at her little one’s sudden newfound eagerness for the cage. But she still didn’t want to let this unique opportunity go to waste.

So she made her little diaper boy get on his knees, kneel before her in his poopy pamper, and beg. Beg her to lock up his tiny weewee in a permanent cage. Beg her to make it impossible for him to ever masturbate in his diapers again. Beg her to keep his naughty little doodle locked away for forever and ever and ever.

After a long, humiliating pause, where his Mommy feigned the process of still deciding while her little one continued crying and begging in his poopy diaper at her knees…

She finally agreed. Daniel’s Mommy would lock him up in his new, little pink chastity cage, after all. Just as he had requested.

We walked the teary-eyed Daniel back to his nursery, changed him out of his poopy diaper, and together, we locked his little red doodle up tight in his brand new sissy cage.

He was then freshly powdered, diapered and taken home—his chastity cage now permanently locked beneath his long-beloved crinkly diapers.

* * *

Looking back, I can’t help but smile at such a job well done.

With his Mommy’s help, I had successfully turned an unrepentant, shameless, dirty diaper masturbator, into a sissy eagerly begging his Mommy to lock up his weewee and throw away the key, just so he never had to touch his naughty peepee ever again…

From what I hear, upon returning home, Daniel’s Mommy immediately set to transforming her previous little boy into the new, diapered sissy that she always wanted.

She changed his name to Danielle. She transformed his wardrobe into that of the pink and pastels properly befitting a sissy diaper girl. She grew his hair out, painted his nails, and did everything else appropriate for a sissy little one.

And most importantly of all, Danielle’s new ‘sissy clitty’ is still tightly and permanently locked up beneath his diapers to this very day.

Returning to the topic of this guide, Danielle’s filthy, shameful diaper-masturbation habit is now thoroughly and permanently done with. To the little sissy, memories of such behavior are now just long ago memories of the past.

Of course, that being said, I imagine the naughty sissy diaper pervert still suffers bouts of intense, private sexual misery and longing, as he still occasionally remembers the intense pleasure he once achieved when he was still able to play with himself beneath his soggy diapers…

But that’s what makes this particular method of punishment one of the most delicious punishments of all. Because the little sissy will always be forced to remember, with painful, humiliating irony…

He was the one who begged his Mommy to permanently lock up his peepee, not the other way around!

I suppose the old adage is true. Be careful what you wish for, my naughty little diaper babies. You just might get it!

Closing Thoughts

As you can see, the above example demonstrates the profound effectiveness of this unique type of punishment. I can’t recommend it enough! I hope you enjoyed reading about it as much as I enjoyed every second of implementing it.

But on another note, in the story above, I happened to mention something that I haven’t yet touched on elsewhere in this guide. That something just happens to be the very topic of my next and final chapter in this series…

The Chastity Cage. Or as I like to call it, the Holy Grail of diaper masturbation punishment.

See you then!

Nanny