From Private School to Daycare (PRIVATE)

[Kaylaindiapers]

James blushed as she reminded him how things were growing up as he was in diapers until 5 or 6 cause he stopped wearing them during the day but it was a little longer at night!  She was right they always thought he was acting like a baby for attention so his mom began breastfeeding him again... It was so embarrassing and now here he is again..

He kept drinking as he didn’t have much to say and he was afraid what might happen! 

He squirmed a little but nothing besides that as he finished his feeding.. Second time around he wanted to spit the milk out cause he never thought about this but he was about to start his second babyhood but this time as a baby girl!! 
 

“No please I’ll be good I’ll do anything!” He cried as she began patting him she was burping him. 
 

“Owe quit pinching me I’m not a baby!” He whined...

“I’ll stay here..” figuring he really didn’t answer her question but he wasn’t going to play their game! 

[dontyouloveyourmommy]

"Oh, you want Miss Janine to hold you? Are you Miss Janine's special little helper? That is so sweet!" Janine pinched his cheeks again, just to annoy him. "Unfortanately, I have to tend to the other babies, so you will have to go on the floor and play."

 

She lowered him onto the playmat with some of the other babies and gave him some of the rubber blocks. "Stack-ah, stack-ah," she cooed. She grabbed his pacifier and put it back in his mouth.

 

Janine went back to tend to another "baby" who was misbehaving. She began spanking him with the paddle, showing Jamie just what his future could be if he misbehaved.

 

After 15 minutes, the door opened and Britney walked in. One of the other teachers stepped forward. "Hey Britney! I thought you were doing your work in the other nursery."

"The dean said I could do it in here." She smiled at James. "Awww, there's my Jamie-girl! Come on, crawl to Britney, crawl to Britney!"

[Kaylaindiapers]

“Ow ow!” He yelped as it hurt when his cheeks were pinched as she wasn’t easy seemed like she liked to tease him and even cause him a little pain.. 

James didn’t wanna play on the floor! He had no choice about doing anything anymore! 
 

Once he was on the floor he sucked his pacifier and out of boardom he began stacking some blocks.. The crying got his attention it was one of the other boys that was being punished James watched in jealousy as the boy was still a boy and not a sissy girl like him... 

James went back to building blocks then he heard her name..

He turned around and they made eye contact... Damn she’s looking good today he noticed she looked like a babysitter with her hair up in a ponytail and a nice white blouse with a short skirt... 

“No no I’m not!” He said definitely he wasn’t going to let them embarrass him especially his crush!! 

[dontyouloveyourmommy]

"Awww, does someone not want to crawl to Miss Britney?" Britney cooed. She took a few steps forward. "You look so cute, Jamie-Jame. You're wearing such pretty pink diapeys and a cute wittle dress! Oh, I just want to pinch those cheekies!" She fake pouted. "But how can I when you're so far away? Are you being a bad girl, Jamie? I would hate to have to tell your mommy how bad you're being." She started bouncing in place so her boobs bounced up and down, she was wearing a red and black bra beneath her white shirt. "Do I have to give you an insentive to come to Miss Britney? Hmmm, what'll make this sissy baby girl come to her new babysitter?"

She looked around and found a bottle of water that had been left out. She took a long sip of it, letting out an "ahhhh" when she was done. She then let some drip down her shirt. "Oh no, looks like I'm all wet." She started unbuttoning her top, fanning herself and rubbing her breast. "You sure you don't want to come to Miss Britney?"

[Kaylaindiapers]

James blushed bright red to a shade of pink when she his crush awed and cooed at him... She was so sexy even when she didn’t try to be it was just who she was! He wanted to kiss her so bad when she gave him the fake pouty face.. He sat there entertained by her then something happened that he never thought would happen! A MTV video broke out right on front of him!  His jaw dropped his eyes got big as she teased him! OMG he thought as she showed him her bra! He continued to watch the show as she bit her lip and leaned her head back winking at him rubbing her breast.. 

James crawled in record time to her he wanted to be a part of this show!!! 
 

“Britney Britney!” He cried crawling to her! 

[dontyouloveyourmommy]

"Awww, look at this little girl," Britney cooed. She lifted him up into her arms and pressed a kiss to his cheek. "Such a sissy baby, aren't you? Look at this pretty dress and your pink diapeys!" She stuck her hand down his pants and smirked at the chastity belt. "This is just what a sissy baby like you needs, isn't it?" She bounced him up and down, her own boobs bouncing along side him. "Oh, I bet you'd do anything to get these titties, wouldn't you?" She cooed. "But you're just a little baby, yes you are. And in fact, you've been a naughty baby." She squeezed his penis within the belt, hard, not in a way to cause arousal. "I really should rip this off and make you the sissy baby that you deserve. But instead..."

 

She carried him to the punishment corner and showed him the impliments. "You pick out what Brit-Brit will spank you with."

[Kaylaindiapers]

He was so excited when she kissed him as he smelt her perfume and her body lotion and the hair spray and he couldn’t help but admire her body as when she bounced him so did her tits. 
 

James blushed bright red as she discovered what they did to him.. 

“No I don’t deserve this please help me out!” He whined.. 

james thought foolishly she might help him but that changed real quick! 
 

“owe ow!” He yelped as Britney had her fun! 
 

“Wh- what no please I don’t need a spanking!” He cried begging her not To make him pick out his own punishment device.. 

[dontyouloveyourmommy]

"Oh, but you do deserve this, Jamie," Britney cooed. "You were such a big boy, making fun of my baby brother. You called him all sorts of names and now look at you." She pulled up his dress, then dropped his diaper to his knees. She took a portion of his ass into her hands and squeezed. "But now look at you. Pissing and shitting your diapers like a real baby girl. Wearing a dress. At least Benjamin is a nice, good friend. You're a terrible person, a bad, bad boy." She smacked his caged penis, then his bottom. 

 

"Now, I'm going to ask you again, Betsy Wetsy. What do you think you deserve? The strap? The paddle? Maybe a belt? Or maybe we can go outside and you can pick a switch off the tree. That's what my dad when I was a naughty little girl. And of course if I picked the smallest branch, I got beat with the bigger one, twice as hard. But that'd be nice, it's beautiful weather. I could spank this little hiney," she smacked his bottom again. "In the quad."

[Kaylaindiapers]

James covered himself up feeling totally exposed as she untapped his diaper.. He truly felt like a sissy as she degraded him and spanked him she manhandled him... “Owe please!” He whined as he danced around as it hurt when she smacked his manhood.. 

“N- no please the paddle!” He began crying as it was so humiliated to have to pick out the own device that is going to hurt you! 

[dontyouloveyourmommy]

Britney smiled. "That's a good girl." She pinched his cheek and grabbed the paddle. It had deep red letters imprinted onto it that read "Naughty Baby", so it'd leave them behind on his ass. 

She walked over to the overstuffed recliner and sat down, pulling him over her lap. "You're going to get 50, you naughty,  naughty baby. And I want you to thank me for this, because you deserve it."

Britney thwapped his bottom with the paddle five times in quick succession. 

[Kaylaindiapers]

“Ow!” James yelped as she didn’t pinch him Lightly... James stood there and in one quick motion she pulled him over her lap and he hated being scolded.. 

“Please please ow owe- n— no no!” He cried yelling and kicking as the spanking was deadly accurate.. James was crying and kicking his legs! As the spankings continued.. He was determined he would be a perfect baby girl... “Please I’ll be good i’ll be good!” He cried between sobs 

[dontyouloveyourmommy]

"Damn straight you'll be good, or your mommy and I will spank you silly." She thwapped his bottom repeatedly, accenting her words with the paddle. "Did you know she made me your personal babysitter? So if she needs to go out, I can come over. And maybe I'll wear my tight mini skirt, the one I wore to that party where you kept trying to grind on me." She laid down five more smacks. "And I'll bring Jason. My boyfriend. He's looking forward to see you as the sissy little baby you are."

 

She dropped the paddle and pulled out her phone, taking a picture of his bright red ass.

[Kaylaindiapers]

James cried and cried as the girl who he wanted to be his girlfriend whipped him like there was no tomorrow! “Please please I— I- I’ll be good!” He cried some more.. He hated being scolded as she whipped him it was like insult to injury! 
 

“Your boyfriend I— I wanted to go out with you.” He cried and begged..

”Please don’t b- bring your b- b— boyfriend over.”
He whined between sobs stuttering nervously.. 

[dontyouloveyourmommy]

"Why would I go out with a big bully turned sissy baby?" Britney mocked. She finished taking pictures and pulled his diaper back up. "There, that's all done." She flipped him over and cuddled him like he was a real big baby. "Now, who wants to make their mommy a nice picture to say you're sorry for being such a bad baby?" She pinched his cheek and carried him to the craft table. Britney strapped his back to the chair and pulled out some finger paint, along with some paper. "And if you get any on your uniform, I pick out a new outfit for you!"

[Kaylaindiapers]

“I- I don’t know I’m not a real baby!” He stuttered in his defense hoping she might believe him.. In reality it was the last of his male ego being shattered! 
 

“Me.” He said he hated how she knew just how to hold touch and talk to him.. He felt so close to her as she cuddled him close.. He would do anything for her! 
 

He sat there and ready to start painting..

”You’re not really going to bring your boyfriend over right?” He was very nervous about that so much so he wet his diaper at the thought..