From Private School to Daycare (PRIVATE)

[dontyouloveyourmommy]

Fiona sighs as she hangs up the phone. She thought it'd be good to be the dean of the school her son attended, until he started acting up. He had started to get into trouble, making fun of kids and acting like he was tough shit because his mom was the dean of the school. The latest issue had come with a student who had to wear diapers for incontience issues. Fiona knew about this kid and made sure he was well protected. Little did she know, her son James had been bullying him over it for weeks. Fiona had enough. Her son wanted to be a jerk and mean to kids with differences? She'd make sure he learned his lesson.

 

A quick dial of her phone got her to her son's classroom. "Hi, I'd like Jamie to please come to his mommy's office," she said over the loudspeaker. "I need to check his diapey."

 

It was enough humilation to get the ball moving. She went to her closet and removed a package of diapers, some changing stuff and a baby version of the girl's school uniform. It was a short pink dress with a smocked front and the school's logo on the breast. 

[Kaylaindiapers]

James was a cool kid in school he craved attention so he always told jokes and did things to impress people.. He was short for a guy 5’4 120 he had long blond hair, he liked to think of himself a rebel or a rock roller! He and his friends had made fun of this kid cause he wanted to hang with them and play basketball... James was jealous cause he always seemed to get the good looking girls to hang out with him and laugh at his jokes.. One of the girls was Britney that was the kids sister and James had a crush on her... For whatever reason he could never get her attention so he picked on her little brother... He sat there in class blowing it off after all his mom was the dean! 
 

“Go away loser I heard you wear diapers like a baby why don’t you go over in the corner and see if they will get you some building blocks!”
He and his friend laughed..

James smiled as he replayed that in his head... 

He turned bright red and felt the heat wash over his body he wanted to be an ostrich and bury his head in the sand.. 

“Wh— what what the hell!” He said when he heard the announcement... He tried to play it off..

”She’s just joking.” He left the class and was going to his moms office..

”I’m going to tell her like it is!” 

James was confident cause he pretty much did what he wanted as his mom was a single parent cause his dad died in a plane crash.. 

He barged into his mom’s office 

“What the hell was that about!” 

[dontyouloveyourmommy]

Fiona was over 6 feet tall, with piercing green eyes and blonde hair. She smirks at James' outburst. "Oh, Jamie, that's big boy language and you're far too young for that." She crossed the office to him. "Mrs. Trench told me that you've been bullying that poor boy, all because he wears diapers. I thought I raised you better than that." She popped his bottom. "You used to be such a sweet little boy, Mommy's sweet little prince. And now you're becoming a big brat. You have more hormones than a teen girl, for fuck's sake!"

She grabbed the diaper from her desk and holds it up for him. "This is where you'll be going to the bathroom for the next year at least. You'll wear it and I'll make no secret about it. And since you want to tease people, clearly you need to learn to be a better friend. The daycare center will be happy to have you back, to teach you everything you need to know."

Fiona smiles. "Now, drop your pants, Gumdrop. It's time for your new diapeys."

[Kaylaindiapers]

James was taken back normally his mom lets him have his way and this wasn’t the first time he cussed at her! 

“Wh- what no you have it all wrong!” He said stuttering nervously 

“Owe!” He yelped more out of shock then pain... His mom never spanked him since he was five and now he had a quick reminder that it did hurt it hurt his bottom and his male pride. 
 

He looked at what she was holding it was a diaper and it was pink! 

“What no please you can’t be serious I’m sorry I’ll do better!” He begged and pleaded as he knew he was in for it now! 

“Daycare center no you can’t do that the girls will know!” He began crying as this was too much! What if Britney saw him like this or her friends! He couldn’t let this happen.. 

He was going to call her bluff..

”I’m not wearing that damn thing I’m not a stupid baby!”
 

 

 

[dontyouloveyourmommy]

"You've promised to do better before, Jamie, and you never get better. You just continue to act out and bully others. Is that very nice? I don't think so. Obviously I raised a spoiled brat. So, let's get this over with." She laughed as he began to cry. "Aww, you're afraid of your special Britney knowing? Let me tell you something, I told Britney that you were Mommy's little baby, showed her the teddy bear you sleep with. That's why she doesn't want to date you, because you're just Mommy's big baby, aren't you?"

 

When James cursed, she's tsked. "Oh, but I'm afraid you are, Jamie-Boo. And no cursing." She walked over and pulled down his pants, followed by his underwear. She popped his bottom 5 times in quick succesion. "Look at that dinky little penis you have, it's like you're a baby girl! Are you Mommy's little princess? Who's Mommy's little princess?" She pinched his bottom. "Now you lay down on the floor, or do you need more spankies?" 

[Kaylaindiapers]

“My names James!” He said angrily as Jamie was a girls name and he hated it! James was crying as this was too much and he knew his life was about to change..

“You did what you know I don’t sleep with a damn teddy bear!” He was furious how everything was coming at him so fast he had no time to think! 
 

“No I’m not a baby how dare you ruin things with her!” He was thinking now maybe he could explain things to her and she would now give him a chance.. 

James thoughts were quickly interrupted as his mom made her move..

”Qu— quit you can’t do this!” He yelled as she began taking his pants off... She was bigger and stronger and he really couldn’t fight her off.. 

“Owe owe owe!” He cried dancing around trying to avoid the hard smacks..

He blushed bright red as she made fun of his manhood... 

“I’m not a girl!” He was crying and rubbing his bottom as it stung..

”Please mom I’ll be good please!” He cried.. 

“No.” he cried some more.. 

At the threat of a spanking he laid down..

 

[dontyouloveyourmommy]

"You will be good or Mommy will spank her little Princess," Fiona cooed. She grabbed hold of some lotion and rubbed it over his bottom and privates. "I remember doing this until you were 5 years old. You couldn't be potty trained, you were just so precious. What happened to that? Oh, such a cute little tushie." She gave it a pinch before sliding the diaper under it. She taped it up nice and tight. It spread apart his thighs.

"Now let's get you out of these big boy clothes." She untied his tie and unbuttoned his shirt, taking them off along with the jacket. "Aww, you're so small. Mommy will fatten you up, yes I will, yes I will." She grabbed the dress, which was pink and had a smocked front. "Since you didn't work out as a good boy, maybe you'll be Mommy's good girl, Jamie." She slid the dress over his head. It barely covered his pampers, leaving nothing to the imagination. "You look so cute!" She gave him a kiss on the mouth as if he were a baby and pinched his cheeks.

Next came off his socks and loafers. She replaced them with white socks that had pink bows and a pair of bright pink Mary Janes. "I should do your hair. You insisted on growing it out, after all." She got up and went to her desk to look for ribbons.

[Kaylaindiapers]

James bottom was still stinging he didn’t want a spanking especially when he was in such a vulnerable position what could he say or do! 
 

“Please can’t we talk about this!” He cried as he was humiliated as he got an erection as she rubbed him with lotion touching his special place.. 

“I don’t know but I can do better please everyone will laugh and Britney will never go out with me!” “Owe!” He squealed sounding  like a little girl..

He watched in horror as she unfolded the diaper and in one quick motion slid it underneath him the pulling it tight between his legs and taping the sides..  

“B— but why a pink diaper can’t I at least have a white one!” He was already resigned to the fact that this was happening... 

Once he was undressed down to his diaper he looked at what she had planned.. 

“A dress I- I can’t wear that please I’m a man I’ll be good!”
He cried as his mom began dressing him.. 

“Quit quit I can’t do this!” He felt stupid as his mom was treating him like a real baby even giving him baby kisses.. 

James felt like a paper doll or a baby doll as his mom finished dressing him..

”No no I’ll get a haircut please I’ll cut it off!” He cried as now he knew keeping his hair long against her wishes was really about to bite him right in the ass.. 

As she was digging through the drawer he had a chance to look at himself he looked just like a toddler baby girl... He was really embarrassed he quickly noticed with each movement his diaper crinkled and it was loud sounded like a shotgun going off! It felt like the diaper was mocking him.. 

[dontyouloveyourmommy]

"No, the chance to talk is gone. it went out the window when you acted like a bad, bad baby. You don't want everyone laughing at you? Then maybe you shouldn't have made fun of that poor boy. He's a real man, he has to wear a diaper but he's kind and sweet. Unlike the little brat boy that I raised."

She grabbed the ribbons and brush, coming back over to him. Fiona began brushing out his long locks. "You look like Rapunzel with this ridiculous hair. I always wanted to style it, put it in some nice pig tails." She sectioned it out and tied it with a hair tie, followed by some pink ribbons. "Oh, Jamie, you're going to be such a happy baby girl. You're going to go to daycare and be with some other naugthy kids who couldn't get their act together. You'll get to see Miss Janine, you remember Miss Janine, don't you? She was your babysitter for years, she'll be so excited to see your chubby wittle face."

Fiona put the other half of his hair into the other half of the pig tails. "Awww, look at Mommy's baby princess. Now, here are new rules."

"One, you are going to be like this for at least a year. If you don't turn your act around, there will be no college for you. Two, you will wear your diapers and not play with them. No playing with yourself either. Three, I choose your outfits. Four, you will address me as Mommy or Mama. Five, you will crawl or I'll carry you. Six, your bedtime is 7 PM. Seven, you will be breast fed and fed baby food. Eight, no more going out with friends, unless Mommy is with you."

[Kaylaindiapers]

James sat there as she scolded him and brushed out his hair.. “Fine but how long do I have to do this!”
He wanted a time table so he could count down the time.. 

“Everyone’s going to laugh at me!” 
James wanted to stomp his feet as she continued doing his hair and telling him what his future is going to be like..

”I can’t go to daycare no not her she’s strict and her daughters used to tease me when they watched me cause I was still In diapers at five they made me take naps and drink a bottle they were mean!” 
 

“Have you lost your mind breastfed!”

james turned as pink as his diaper at the thought of that!  All the rules were bad but baby food and breast fed!! 
 

[dontyouloveyourmommy]

“It’s going to be for a year. Yes, people will laugh because you’re a mean baby who’s getting what she deserves.” Fiona pats his cheek. “Now, now, Miss Janine isn’t mean. She just made sure you were behaved. I am not crazy, you are a baby and must be breast fed.”

 

Fiona stood him up and attached a pink harness to him. “Let’s go to class you can say you’re sorry.” She put a bright pink pacifier with a stuffed unicorn attached m in his mouth and lead him down the hall, walking slowly so everyone could see him walking.

 

“After this, you can go to daycare. But you will apologize or mommy will spank you in front of everyone.”

[Kaylaindiapers]

“A year b— b but then I’ll really need diapers!” He wanted to cry so bad and throw a fit.. I don’t want a spanking but this is too much! Since she’s my mom I’m going to be a baby at home too! He thought this to himself as his mind was racing! 
 

“I’m a man not a girl!” He whined as she attached a harness to him.. 

James felt like he was on display as he noticed his dress didn’t even cover his diaper very good that meant everyone can see it and he knew it too! 

“I’m sorry.” He said behind his pacifier with tears in his eyes... He apologized to anyone and everyone he saw.. Then he saw her down the hall approaching them.. “Please mom can I go to daycare now!” He whined trying to pull so he could get away and not have to talk to Britney! 
 

 

[dontyouloveyourmommy]

"A man wouldn't be asking to go to daycare, now would she?" Fiona cooed, pinching his bottom. She saw Britney coming down and the hall and grinned. "Oh, why are you wiggling so much? Does Mommy need to hold her little Princess Pop?" She scooped him up and cuddled him close as Britney approached them.

 

"Is this James?" She asked, a smirk falling on her lips.

 

"I told you Britney, she's just a big baby girl named Jamie."

"Aww," Britney cooed. She pinched his cheeks. "Look at this cute baby girl! I just wanna eat you up." She patted his bottom. "Look at that big diapey bottom. Can I babysit Mrs. Jensen?"
 

"Of course you can, Britney! I'll need your help. You can look after Jamie and clean her bottom and feed her babas. Oh and then you can tuck her into her crib in her bubblegum pink nursery."

[Kaylaindiapers]

“N- no but please I don’t want her seeing me like this!”
He whined but it was too late it seemed his mommy was out to embarrass him.. 

“P- put me down put me do- down!” He said struggling for all he was worth of course it made him look even more babyish.. 

James checked her out damn she’s so gorgeous he tried to picture her without her uniform he was guessing black bra with black thong panties... The thought alone got him excited! 
 

“What no she can’t I won’t let her!” He yelled as the girl he was crushing on was now going to babysit him... It was a fantasy to be alone with this beautiful creature but not like this.. 

“Crib nursery what are you talking about!” James hadn’t been home to see his new room! 
 

Great she’s going to make fun of my small package and probably talk about her boyfriend or other guys and say how they’re real men and not sissies like me... James knew things were only going to get worse! 

[dontyouloveyourmommy]

"Awww, she's fussy. I think she needs a nap. Say bye bye to Britney," Fiona made him wave to Britney and carried him down the hall. "You see, Jamie? No one will ever take you seriously again. You're just a wittle baby!" She patted her head and then fished through her bag, popping a bright pink paci that read "Mommy's Poopy Girl" in his mouth. She tied it around his head so he couldn't spit it out.

 

Soon, they were at the teen nursery. They had a nursery school for actual babies, but this was for the bullies who acted high and mighty to go. Most in there were already regressed, reading board books and being bottle fed in their adorable uniforms. There were several large cribs in a circle, three changing tables and an assortment of toys in the playpen. And of course, the punishment corner. An array of spanking tools hung from the wall: paddle, belt, spoon, ruler, etc. There were hard time out stools. Fiona's favorite was the oversized stroller. If a baby was too bad, they were brought to the  home ec class to be cared for by the pretty girls.

 

Janine, a tall woman like Fiona, approached them. She wore a white button down and a short brown skirt, a pair of black glasses framing her piercing brown eyes. Her dark hair was tied up so it couldn't be pulled.

 

"Janine, do you remember Jamie?" Fiona asked.

"Of course I do. Always such a naughty little boy, but I see now she's a cute little girl," Janine wiggled his chin. "Aww, look at those diddums." She stuck her hand down his diaper and tugged on his penis. "We need to get this in a chastity so she can't play with herself like a bad girl."

"I totally forgot."

"That's why I'm here, Fiona." She tapped James' nose. "Say bye bye to Mommy. It's time to come with Miss Janine."

[Kaylaindiapers]

“I’m not being fussy both of your suck!” James hated how she held his hand making him wave bye just like a mommy would do with her baby.. 

“What do you mean by a crib!” He was really dreading if he wanted to know the answer but certainly she couldn’t mean a real crib! He thought to himself checking out Britney’s sweet little ass... 

“Answer me!” He whined behind the pacifier as obviously his mommy had enough of his talk... 

Once they got to the nursery James jaw dropped when he stepped in the room it looked just like a real nursery school with pastel colors and letters spelling out baby in blocks elephants and giraffes on the wall and he saw the cribs.

”Please I’ll be good I promise!” 
 

James was scared of this place as he saw the paddles they could choose from This was awful and of course him being dressed like a baby girl made things worse! 
 

When the instructor or the nursery school attendant came by he remembered her right she was still pretty she really hadn’t changed a whole time had been good to her.. 

“I’m not a girl awe!” He squealed as she pinched his checks..

”H- hey what the hell awe!!” he yelped when she grabbed his manhood..

”Chasity what is that?” 

He wanted to hit her when she bopped his nose like he was an infant! She probably expects me to laugh.. 

“Please mommy please don’t live me here!” He cried like a real sissy baby who’s mommy was dropping him off at daycare... 

“I hate this place I’m not a baby!” He yelled stomping his foot as his pigtails flopped around.. 
 

 

[dontyouloveyourmommy]

"Swearing, Jamie? I think you know better than that. It's time for a spanking, young lady," Janine told him.

"If you weren't a baby, you wouldn't be throwing such a tantrum," Fiona pointed out. She kissed his cheek. "Be good or Miss Janine or you'll get a spanking at home too." She walked out of the nursery, smiling.

Janine carried James over to the punishment corner and sat in a chair. "Since you're new at this, I will spank you with my hand. If you keep this up, you get the paddle." She pulled him over her lap and flipped up his dress, pulling down his diaper. She smacked his behind once, then twice.

"We do not swear here, little girl, and we don't even use our big kid words. From now on, when you're here, you talk like a baby or you are spanked. We need to start you from the beginning." She smacked his bottom hard, turning it from pale white to nice and pink, like the ribbons in his hair. "You are a bad, bad baby girl and I'm going to make sure you become the good girl your mommy wants."

[Kaylaindiapers]

“I’m not a girl!” He yelled as the teacher easily picked him up...

“P- put me down now!” He yelled kicking his feet trying to get away! 
 

“N- no please please!” He cried and begged as the tapes of his diaper was undone and he felt the cool air hit his bottom then the whack after a few smacks his ass was on fire.. 

“No no please quit please i’ll be good!” He cried kicking his feet..

As his nursery teacher didn’t let up..

”I’ll be good I’ll be good!” He cried 

[dontyouloveyourmommy]

“Damn straight you’ll be good,” Janine told him. “If you misbehave again, I’ll let your little crush spank you.”

 

She smacked his penis. “How pathetic. You’re a pathetic little girl.”

 

Janine spanked him for a few more minutes before dragging him by the ear to the changing table. She put him on top and grabbed hold of a chastity belt.

 

”This is for sissy little babies who can’t be trusted.” She slid the belt around his waist and clicked the tube into place. “Now you can’t play with yourself, you little baby girl.”

[Kaylaindiapers]

James was really nervous and scared thinking Britney would probably love to get him back for picking on her brother.. 

“Owe owe!” He yelled as he never had his manhood smacked.. 

“My ear owe owe!” He tried to slow down but that only made her squeeze harder on his ear.. 

James laid there as she put him in a pink chastity..,

”Wh- what no pl— please no you can’t do this!” He cried 

As like most guys he enjoyed pleasuring himself often to the image of Britney in her lingerie going down on him!  Now his good times was over! 

[dontyouloveyourmommy]

"Oh, I can do this. You see, you're just a sissy baby girl, you can't call the shots." Janine smirked down at him, stroking his chasity belt. "This is much better, this shows just what a sissy baby you are." She taped his diaper back on and then grabbed a pair of bright pink plastic diaper panties. She slid them up his legs and locked them into place. "That way you don't get any funny ideas about playing with your diapers."

 

She lifted him back up from the table and pinched his cheek. "You've had quite the morning. I think it's naptime." She carried him over to the rows of cribs and found one decked out in the most girl stuff. It had pink sheets, lots of stuffed animals and a ballerina mobile. She lowered him into it and pressed a button on the wall, causing a barred top to go over it. Through the bars, she stuck his pacifier back in and patted his diapered rump, causing the diaper to crinkle. A sound machine was flicked on.

"Night night, Jamie. See you when you wake up."

[Kaylaindiapers]

James didn’t know what to say or do! He hated that stupid chastity thing he accidentally stumbled on a video online where this guy was dressed in a white dress and a woman was pounding him with her strap on! He watched for a few minutes and he saw the same thing he now has on his dick! 
 

“Please don’t do this I can do better!” 
 

“owe!l he squealed like a little girl as his checks were pinched... He was finding out quick this woman enjoyed teasing and torturing him! 
 

“nap time B— but I’m not tired!” James was quickly finding out it didn’t matter what he wanted or what he said he had no say in anything... 

Once he was in the crib he looked around he wanted to hurl with the overload of pink!!!

James didn’t want a spanking so he laid there watching the ballerinas go round and round and soon he was asleep. 

[dontyouloveyourmommy]

While James slept, everything was changed for him. His room at home was transformed into a bubble gum pink nursery with lots of pretty dresses and onesies for him to wear. A diaper delivery service was scheduled and his mom began taking lactating pills so he could breastfeed.

 

After a couple of hours, Janine went back around to the crib. "Wakey wakey, Jamie, she cooed. "You've taken a long nap." She lifted him from the crib and sniffed his bottom, grabbing the front. "Someone needs a change! Oh well, that can wait until after your num num time!" She tapped him on the nose and carried him over to the kitchen area. She took out a bottle and fixed him one with their special formula. It would keep him full for a bit, but would weaken his arms and legs so he couldn't run away. She tied a frilly pink bib to his neck that read "Mommy's Girl".

 

She sat down in a rocking chair and removed his pacifier. "Open wide, here comes your baba."

[Kaylaindiapers]

“Wh- what?” He said trying to wake up then he felt her check his diaper now everything came back to him... 

“Please please I thought this was all a nightmare!” 
Shit this is really happening he thinks to himself as he watches he make a bottle he knew that was for him! 
 

“I’ll be good I’m not a baby and especially not a girl!” He squealed as his sissy side was coming out.. 

“No no I’m not hungry!l he cried as she held him then the bottle silenced his cries as he had no choice but to start drinking.. 

[dontyouloveyourmommy]

"You must be hungry, you slept all through lunch," Janine cooed. "Aww, aren't you just precious? I remember when you were 5 years old and still in the other nursery. You kicked up such a fuss about getting out of diapeys, and your mommy had to come in to breast feed you. You'd cry and cry unless she did. Such a wittle mama's boy. But now you're mommy's baby girl and she'll do anything for you. She'd come breast feed you now but her milky hasn't come in yet. Maybe tonight! Won't that be fun!"

 

Janine held him until he finished his bottle. "There we go, all done! You're going to get nice and chubby, I can tell. You were such a chubby little kid, should be that way the second time around." She adjusted him on her lap so he would give her a nice big burp. "Good girl! Who's my good girl? I think Jamie is!" She pinched his cheek. 

 

"Now, you have two options so choose wisely. Do you want to go in the baby swing and hang out or do you want to place on the floor with the other babies?"